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/lgbt/ - Lesbian, Gay, Bisexual, & Transgender

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Post your crossdressing stories!

>times you were caught
>narrow escapes
>the clothes you liked best
>adventures you had while CDing
>discovering you were into it
>getting your first clothes
>being dressed up by others
>coming out

Former thread >>9126016
I wore my mothers lipstick when my parents weren't home after waiting for about 2 weeks for them to go out when I was 5.
idk why I remember it, maybe cause my father screamed at me?
That image is beyond creepy and putrid
>be me
>3 years old
>sisters 6th birthday party
>refused to go unless I got to wear a pink ballerina outfit with fluffly tiara
>parents actually give in and let me
>seeing the photos to this day make me cringe

I'm not even trans, just a straight acting faggot. Although sometimes I wonder whether I'm repressing so well I don't realise since 3 years old is pretty early to start wanting to dress like a girl.

Try not to think about it since I loom very many nowadays, have a big roman nose chad jaw.
That image is a caption based on someone else's drawing,

But I used to read the original artists stuff all the time when I was a kid, he had a full story called 'Lipstick discipline' about a mom making her kid crossdress that was my first time hearing anything about feminization fetish stuff

I was 12ish when I first found it and read it every now and again till I was 19 and decided it was a bit weird to be jacking off to a 13 year old being forced to crossdress by his mom (even if it was imaginary).

Still to this day I'd pay for feminization stuff that's illustrated and not so massively sexualized (sissy stuff makes me want to barf)but there's no quality stuff that I can find
>not sure if typical child whim or proof Blanchard was right about HSTSes
Probably just kids being kids
>be me
>come out to your mother
>she doesn't support you
>months pass
>you suddenly have a female pajama in the closet

last week
How unsupportive is she and how old are you?

Just how female is your new garment?
Wore cousins one piece swimsuit when I was visiting Korea at 5.

Wore babysitter’s panties tied back because I got my clothes wet at 6.

Wore friend’s lacy socks when I was 7.

Wore mom’s clothes while she was at work on and off throughout elementary school.

Wore mom’s panties under clothes during a field trip in 5th grade.

Used Grandma’s lipstick and nail polish in middle school.

Used stepmom’s nail polish and tampons (ugh) in high school.

Bought own female clothing and makeup in college and cross dress regularly while alone at home to this day. Own more dresses and heels than guy clothes and shoes.

This fetish is a curse, but I manage somehow.
More detail on the first five! The first two in particular sound interesting.

>This fetish is a curse,
Take that back!
>tfw you'll never come home early one day to find your until-then closeted femboy roommate vacuuming the apartment fully dressed in a french maid outfit with stockings, panties, and heels, and a nice fat plug in his bp.
>tfw you'll never see the terror and shame in his eyes turn to relief and understanding as you casually make your way towards him while undoing your belt and drop your pants to reveal your fully engorged dick before which he instinctively descends to his knees
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I have quite a few crossdressing stories. I eventually started doing drag while in college, and this is pretty much how it all started.

>8th grade, am pretty skinny and moderately effeminate, friends with a lot of girls
>Not openly gay but pretty much everyone knows that I am
>Late October
>Good friend tells me that her parents are going out of town and her older sister (17) is having a Halloween party
>Her sister says that she can invite a few girlfriends to the party, but I can come because her sister likes me
>Day before the party, friend tells me that she and her sister really want to dress me up like a girl, think I would look cute
>Never really thought about crossdressing before
>Reluctantly agree
>Day of party, she calls and asks me if I can come to her house a couple hours early so they can get me ready
>Tell parents I'm going to spend the night at a guy friend's house
>Walk over to her house, am actually kind of looking forward to dressing up, curious to see what I look like
>It's just my friend, another girl from my grade, and her older sister and her friend there
>They're all very excited
>Take me upstairs to her sister's room
>House is huge, her sister's room is the size of a small apartment
>They have five or six dresses laid out on the bed, tell me to pick one
>Choose a mid-length green dress, looks very similar to the attached pic
>They have to show me how to put it on because I have no idea
>They give me a padded bra and I go into the bathroom to change
>Come out, they laugh and point out that they can all see my bulge because I'm wearing boxers
>Friend runs to her room and gets me a pair of panties, the girls are actually being really nice and promise they won't tell anyone I'm wearing them and not to be embarrassed
>Put on a pair of green heels, honestly starting to feel pretty sexy at this point
>Sit down at the vanity and they spend at least an hour doing my makeup, they even pluck my eyebrows

>Not openly gay but pretty much everyone knows that I am
why do gays get to live the dream agp life
Because they’re courageous enough to live at least that honestly to themselves. They deserve it for being so strong.

Most AGP are cowards.
I got one.

>Be me
>9 years old
>Just began repressing feminine feelings a year before
>Practically fueled by video games
>Brother has flashy brand new PS2
>Brother is very protective of his stuff
>I want to play it
>Brother challenges me to do ridiculous, normally humiliating stuff to do so
>One of these was watching 15 straight episodes of Barney the Dinosaur
>Challenge accepted
>Challenge succeeded
>Next challenge: wear sister’s clothes for the day
>Oh Christ, I’m about to wear girls clothes
>Wear sister’s Barbie-themed nightgown
>First time I’ve ever worn girls clothes on my own accord
>So this is what wearing a dress feels like
>Wear that, later a two piece PJ set (also sister’s) for the remainder of the day
>”Yeah I was just joking the whole time”
>Dad comes home, questions me and my brother
>Repressed this up until this year
Is anyone else crossing dressing at this moment?
>>First time I’ve ever worn girls clothes on my own accord
>on my own accord

You got me.

>The only wig they have is a cheap pink one, but they style it and it looks decent enough
>They paint my nails bright pink
>At this point I am SHOCKED at how good I look
>100% look like a hot girl, can't stop checking myself out in the mirror
>Go downstairs, they give me a vodka tonic
>Only been drunk once before, decide I'm going to get hammered tonight, kind of nervous because everyone at the party is going to be 3 years older than me
>Get drunk in like 20 minutes
>Spend the next hour or so dancing with the girls in the living room, they're taking a million pictures of me
>Lose all my inhibitions, am legitimately having the most fun I've had in my life
>People start trickling into the house, party starts to get pretty big
>Older sister starts dragging me around and introducing me to all her friends
>All the high school girls fawn over me, keep telling me how pretty I am, I'm honestly loving all the attention
>Some of the high school guys give me dirty looks, some seem slightly amused
>Play some drinking games, act girlier and girlier the drunker I get
>Older sister and a few of her friends ask me if I want to smoke weed with them upstairs
>Say yes, never smoked weed before
>Go up to her room with four or five other girls
>I take a few hits, I'm very fucked up at this point
>They ask me a ton of questions, ask me if I'm gay, if I've ever crossdressed before, etc., don't even remember what I said but I remember telling them that I love wearing dresses
>Rest of the night is a blur, eventually I pass out in my friend's bed with her, at some point she gave me pajamas to wear
>Wake up the next day, she helps me take off the makeup and I help clean up the house
>Go home and tell my parents that I just played videogames all night
I’ll admit I didn’t word that correctly. But it was both exciting and humiliating at the same time.
Yeah, waiting for my friends to go home so I can change into a comfier shirt and bra and leggings.
>didn’t fuck any of the girls
A hype as fuck story with the worst ending I’ve ever seen.
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Haha sorry to disappoint you, but nothing sexual happened the whole night. I'm also not into girls, that's kind of why I was invited to the party in the first place.
You’re super lucky. I wish I were confident enough growing up to be as open femme as you. You’re a strong person.
Where do you think you are?
>One of these was watching 15 straight episodes of Barney the Dinosaur

That's child abuse.
This is my first time here, I don’t know the vibe
>tfw agp and coward

why does it hurt so much
When I was in 9th grade (CONFUSING time) my at the time gf gave me an old dress of hers, and I was soooo happy wearing it, like, I felt so beautiful for the first time ever
>tfw no good stories because no privacy and too paranoid to ever wear more than panties
I really need to get my own place.
>tfw this anon lived the dream
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>be turbo AGP, but managing to keep the facade of a normal human bean
>stay over at girlfriend's one night, she goes to shower
>notice her dresser open
>"Awww yiss"
>never crossdressed before but dick is already erect
>pic out a pair of her panties and bra, go to the mirror
>see a pathetic, curveless fridgebod guy staring back
>experience related

I'm now a believer when people say AGP fetishism has the uncanny ability to mutate it genuine dysphoria
>5 years old
>have nightmares of being lost without my parents while dressed as a girl, would always subconsciously attempt to try on my moms boots whenever I went in her room
>wore mom's and younger sisters clothes whenever i was home alone between the ages of 9-18
>started puberty at 13, was too ashamed to fap while crossdressing until 15
>by that time my legs where already hairy and I felt disgusted
>huge period of represssion
>fast forward to me being 18
>start shaving and have a FWB who's comfortable with me dressing up, since i'm pretty fem looking and she's bi
>sexy stuff ensues
>have amassed a collection of girly clothes by this point
>current day, 3 years later
>finally accept who I am
>discover internet porn
>gain a fetish for clothes and satin
>mother wears plain brief satin panties, same style and color
>wouldn't notice if one pair went missing
>parents go out and I'm left all alone in the house for a few hours
>it's time.jpg
>open her drawer and take a picture of it
>take a pair of her panties from the back of the drawer
>spend an autistic amount of time making sure her drawer looked exactly as I found it
>delete picture
>fap with the panties, being careful not to get them dirty to preserve their lifespan
>finish, then clean up and hide them in my room
>later on decide to try wearing the panties late at night while everyone is asleep
>very oversized on me, elastic barely grabbed onto my hips
>planned on fapping, but something clicks when they're on
>figure out I love wearing panties in a non-sexual way
>it just feels right, and as I looked into the mirror I became very disappointed at how ill-fitting they were
>since they were still clean and free from cum, ended up wearing them a few times during the day underneath my normal underwear
>if I didn't wear my normal underwear, the loose fabric would have come out of my pants
>parents went out again at a later date, so I went drawer diving again
>found some unopened black nylon stockings shoved in the back of a dusty drawer
>never seen mother wearing or even owning anything that would need stockings for an outfit
>they also seemed old
>take those, and wear them with the panties at night
>they fit better, but were still too big
>felt great anyways
>this went on for a bit, but eventually fapped in/on all of my stash a few times like an animal
>couldn't come up with a way to clean them that wouldn't get me caught
>snuck them into the trash
>repress everything
>tfw still living at home and haven't gone any further with my crossdressing after all these years due to shame
I need to move out and buy some pretty outfits before I lose my mind from repressing.

Honestly, I don't really think I was being brave or anything. It was Halloween, after all. I was really surprised at how much I enjoyed it. Plus I was super drunk.
told this before
>be twinkish 20 year old
>see ad on craigslist from older divorced guy looking to hook up
>figure why not
>go over to his house and talk
>he has college aged kids who are away at school
>invites me upstairs to fool around
>go into his daughter's room and he ends up fucking me in there
>weeks go by and the routine is the same, always end up fucking in his daughter's room
>one night after sex we start talking about fantasies
>he admits that the reason we fuck in his daughter's room is because his fantasy is to fuck his daughter
>says he obviously would never do that but he can smell her on the sheets when he fucks me and he likes it
>now that he's broached the subject he asks that next time I come over I wear her underwear when we fool around
>never did something like this but why not?
>next time over end up wearing her thong and he fucks me harder than ever
>this goes on for a few weeks
>daughter comes home one weekend and leaves a load of clothes to be washed (took her spring stuff and left winter stuff)
>next time I come over guy says he left some clothes for me to wear on her bed
>skirt, blouse, panties, bra, pantyhose
>get dressed up and he goes out of his mind
>says he can smell her on her clothes and fucks the shit out of me
>gets to a point whenever I go over I immediately have t go to her room and change into her clothes before sitting and talking to him and having a drink before sex
>he bought me a wig that from what I see in pictures looks just like her hair
>got into a crossdressing fetish becasue of him
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>always fantasize about wearing women's clothing or being "forced" to wear women's clothing
>one day in hs my sister is at uni so I go into her room
>pick out some casual clothes, mid-sized cut-offs, baggy shirt, plain bra/panties
>feel really happy putting them on, everything fits because I am lanky af
>feel comfortable with myself for the first time in my life
>catch my reflection in the window walking back to my room
>looks like fucking buffalo bill staring back at me
>throw everything off and cry myself to sleep
>never cross-dress in private again but always fantasize
there was actually one other time I cross-dressed but that was for a senior-year pageant contest, where me and a friend were asked to be show girls as a joke. I got to wear a beautiful pink dress, and I had trouble getting it over my hips and all the women helping me were empathizing and almost treating me like a woman and I got a lot of compliments afterwards. I would never admit it but that was one of my favorite moments of hs.
Would be hot if not for the creepy incest fetish.

I should add he was a psychologist.
And the amazing thing is, neither of you were AGP!

>implying that doesn't make it hotter

It's not like there was even any real incest.

>be me, 6, putting on moms clothes
>pantyhose, a dress, some shoes
>dad catches me
>loses it
>yells for an hour
>gives me a buzz cut (had hair about an inch passed my shoulders at the time
>sells my piano, cause apparently that's gay
>drives 600 miles and turns me over to my mom (they recently separated)
>nobody talked about it, but I immediately started therapy where it was never talked about
>pointless therapy went on for 6 years, i hate shrinks now
>still repressing to this day, now in my 30s

What a life.
/r9k is six boards down pal.
I think I’ve read this in another thread.
Jesus Christ, your dad’s an asshole. I’m sorry.
im so sorry that happened to you
>tfw no crossdressing sex slave to lovingly abuse

It's not far. I want something beautiful to corrupt
Oh shit me too.
Here because I put on some stockings today for the first time and they were super comfy(but not as comfy as some of the stories here) and now I'm starting question myself. Figured this was the best board to see.
>tfw didn't have girl friends who dressed me up in cute clothes
fuck everything

I'll post some more stories later tonight if anyone's interested. Might not have time but I definitely will if I can.
>raping your roomate
>decided it was a bit weird to be jacking off to a 13 year old being forced to crossdress by his mom
why tho??
Please do. I want to live vicariously through your greentexts.
>tfw your roommate will never come home early one day while you're vacuuming the apartment fully dressed in a french maid outfit with stockings, panties, and heels, and a nice fat plug in your bp.
>tfw he will never comfort you when you shy away out of shame
>tfw you will never suck his benis
>maybe cause my father screamed at me?
It's sad how many of these stories there are.
>be me
>its halloween
>too late to order the halloween costume I wanted
>plan B is to wear my sister's old catholic high school uniform
>sister helps with makeup
>she thinks its a joke to me and tries to give me oversized balloon tits
>going to a small halloween party
>about 8 people there, only 3 of us dressed up
>a bit nervous at first but I get over it
>go out trick or treating way later than we should have
>i get a few compliments on my costume
>feel kawaii as fuck
>we go back to the friends house, party's coming to an end
>one of my girl friend's parents mistake me for a girl
>I dont tell my parents its over because i want to stay dressed up longer
>most genuine happiness ive felt in a while thinking im a cute girl
Havent had a chance to crossdress since that night ;-;

Read these two posts first:


So typing up all that last night brought back a flood of memories. I've never actually written out any of this stuff before. I honestly have dozens of similar stories, so I'm just going to go over my whole history of dressing in drag. It’s something I’ve done pretty frequently from the ages of 13-25. I should also clarify that I'm not trans or AGP, I'm just a gay dude who thinks it's fun to dress up and be pretty. I've never really hidden or "repressed" anything (except from my parents, to this day they still don’t know about any of this stuff). I’ve only ever had one sexual encounter while fully dressed up, but that story doesn’t come in until way later. I’ve never suffered any serious negative repercussions from crossdressing. I’ve always had a lot of female friends, and all of them have always really enjoyed the fact that I’m so open about my love of drag. Also I should add that the only reason I even continued crossdressing after that first Halloween when I was 13 is the fact that I looked really, really good. If I would have looked stupid, I probably never would have done it again. I’m just fortunate that I can easily pass as a girl when I want to. I don’t have broad shoulders, I’m naturally slender, and I have a pretty androgynous face. Honestly I do feel bad for you guys that can’t pull off drag (if it’s something that you wish you could do).

So I’m just going to continue where I left off, right after Halloween in 8th grade. To make it easier, I’ll start using the girl’s names. My 8th grade friend’s name is Laura, and her older sister’s name is Jennifer.

>A few days pass, can’t stop thinking about how much fun I had on Halloween, really want to dress up again
>Have a sister who just left for her freshman year in college, she left behind two closets full of clothes
>Start trying on her dresses when I’m home alone


>Tell Laura that I tried on some of my sister’s dresses, she thinks it’s awesome and asks me to text her some pictures
>Come home from school, put on one of my sister’s homecoming dresses and a casual H&M dress, text the pics to Laura
>A week or so later, go over to Laura’s house to hangout and watch movies
>Jennifer is there, calls me “Party Girl” and tells me that Laura showed her the pictures, says it made her really happy
>Asks me if I want a makeover, I say no because their parents are home and I don’t want them to see
>Let them paint my nails though
>A couple months pass, don’t dress up again because I’ve already tried on all of my sister’s dresses already, plus it’s not that fun because I don’t own any makeup
>Laura calls me on a Friday night, tells me her parents are going to be out of town on Saturday and Sunday, they didn’t tell the girls in advance because they found out about the Halloween party from neighbors and didn’t want them to plan anything
>Parents said the neighbors would be watching the house and they would be in a lot of trouble if they saw any cars outside
>Laura says she’s just going to have a few friends over for a sleepover and Jennifer isn’t telling anyone their parents are gone
>Can hardly sleep that night because I’m so excited

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>Next day, Laura texts me right after her parents leave
>Once again, lie and tell my parents I’m going over to a dude’s house for the night
>Head over
>It’s just Laura and Jennifer there, a few more girls are coming over later
>After like 20 minutes, they ask me if I wanna play dress up
>Of course I do
>Jennifer says she bought a bunch of clip-on hair extensions that I can use
>No fucking way
>I tell them I’ve started getting visible leg hair, ask if I can use one of their razors and shave my legs
>They laugh and say of course
>Get in the shower and shave my legs, arms, and pits, doesn’t take very long because I don’t have much body hair
>Come out of the bathroom, both girls have put on 1980s-era party dresses, apparently Jennifer buys them online all the time and never gets a chance to wear them, has like 10 of them
>Pick one out, looks just like the pic attached except it’s blue
>Put it on, both girls take turns putting on my makeup, show me what they’re doing in case I ever want to do it myself
>Jennifer asks me if I want long or short hair
>Say long
>She puts the clip on extensions on me, I know look like I have long brown hair
>Not exaggerating at all, I look absolutely gorgeous

>Another girl from my class rings the doorbell, Laura goes and lets her in
>She cracks up when she sees what we’re doing, she was at the Halloween party so she’s seen me dressed before
>She takes a bunch of pictures of me, Laura, and Jennifer together
>We look just like a group of 80s girls going to a dance
>Wish I still had some of those pictures
>Try on a few other dresses, two other girls show up and we spend the next couple hours dressing up, drinking, listening to dance music
>They do my makeup a few different times in different styles
>Jennifer eventually leaves and goes out for the night
>Spend the rest of the night in drag,
>We just hang out, gossip, watch TV, until we all pass out around 4:00
>Next day, go home, worry that my parents will notice I shaved my arms and legs
>They never notice

Alright, I’m going to bed now, I’ll post more tomorrow night if I have the chance
>I've never really hidden or "repressed" anything
Repression is only for AGPs.
Do you have any other pics?

Your friends sound cool.
This all sounds so nice.
>tfw you will never have female friends who give you makeovers and treat you just like you're one of the girls

No sorry I don't, this was like 12 years ago so they were physical pictures. In high school Laura gave me a photo album that had a bunch of pictures of us dressed up together. I kept it hidden in my room, but I ended up throwing it away because I was so paranoid that my mom would find it while snooping through my stuff. Laura literally had hundreds of pictures of me dressed up, that would be cool if she still had them.
repression is for the kids that noticed people treat your weird or poorly when you act different
>be 14
>with cousins at sleepover
>for fun dress me up as girl
>remember looking in mirror in bathroom and feeling so happy
>at friend of friends party
>friend brings up last story
>they make me dress up as girl
>i am all nooo stop its embarrassing (lovin it)
>look kind nice, get to wear hot bra for first time
>drunk mother of girl thinks i am trans and says how cute i am
>sister has moved out but all her clothes are still at home
>find her 'sexy nurse' Halloween costume
>look really sexy in it
>see hairy legs and all enjoyment is sucked out of me like a vacuum
>continue wearing her clothes on and off till they are picked up
>be now 19
>friends are very chill with me being trans (still not transitioned)
>i will wear out a skirt and thigh high socks with suspenders and sometimes shitty makeup
>when people ask if i am trans we just say its a meme and we are just fucking around
side note, got my leg touched by a ice head tonight who was saying how pretty i am, so some free goon and some cigs out of it
>been crossdressing as long as I can remember
>don't know why. couldn't remember being exposed to it in the past
>started early with me using towels as a skirt
>move to dressing in my mother's clothes when she was out
>crossdressed for guys as part of sex
>one day talking to my mother
>she tells me she really wanted a girl when I was born (she already had a son)
>so, she used to dress me as a girl all the time when I was in the house but had to stop when I started school

tldr: my mother turned me into a transvestite

Continued from these posts, read them first:


>Winter passes, don’t get a single chance to dress up
>Keep hoping that Laura’s parents will go out of town again, but they don’t
>One day after school Laura tells me that Jennifer’s friend got a job at Sephora, says they want to take me there to get a makeover and go shopping
>Say I’d love to but I’m way too paranoid about being spotted by someone who knows me
>That night Jennifer calls and begs me to go, says she promises that no one will recognize me and she’ll even buy me some clothes at the mall
>Say no again, but sad about it because it sounds really fun
>She says she’s disappointed in me, thought for sure I would say yes


>Summer comes, haven’t done any sort of crossdressing beyond letting Laura paint my nails occasionally
>Laura goes to stay at her parent’s vacation house for a whole month
>It sucks, I like hanging out with her more than anyone else
>She comes back in early July, resume hanging out every day
>Following week, parents tell me they’re going to a wedding a few hours away and are going to stay overnight, will let me stay home alone
>Fuck yes, it’s just for one day but I’ll take it
>Tell Laura, she says Jennifer has a bunch of weed and will give her some, asks if I want to play dress up too
>Fuck yeah
>She comes over shortly after my parents leave, brings four joints, a bunch of makeup and some hair extensions
>We sit out on my back patio, get unbelievably high
>Only my second time smoking, it’s her fourth
>Go inside, go to my sister’s room
>Both put on shiny cocktail dresses
>Breaks out the makeup, says she wants to see if I can do it myself
>I try but am terrible at it, plus I’m stoned out of my mind
>She laughs, does it for me
>Put on the hair extensions, she styles it for me
>She brought over a digital camera, sets it on timer and we take a bunch of pictures
>Go to the living room, watch Clueless while she paints my nails
>Go to the garage and smoke another joint, don’t want to go outside because neighbors might see me
>Spend the rest of the day hanging out, high out of our minds, talk about how crazy it is that we start high school next month, promise to stay friends even though we’re going to different schools
>She starts to cry a little, says she’s going to miss being able to see me every day
>Really sweet and heartfelt moment
>She goes home around 10PM, can’t stay the night because my parents will be back in the morning

I really wish I had been caught when I used to do it when I was 12 because it might have forced the issue. Instead I stopped and repressed for another 10 years. Fuck
>tfw repressed flawlessly for 10 years
>tfw still repressing out of shame, but the feelings are leaking out now
I don't even know if I can be cute anymore.
My male best friend. Married. I came out as bi and cd. It got his imagination after initial heistation. He asked loads of qs and I told him I swallow the whole nut. He got hard and I started sucking his cock, he came with 15 seconds. We pretended like it never happened.

A few months later we went on holiday with the boys, me and him had our own apartment, first night before we all went out I smiled at him and it was like we were both dying for it. I told him I want to dress up and for him to fuck me like a girl. We made out and I got dressed up. He fucked me like a girl and came within 5 seconds.

Went out same night, I went home early. He came home an hour later. We made love all night and came everywhere. Told him I love him he told me the same. I broke contact. Havnt seen him in a year.
I travelled halfway across the country for the chance of sex (it was very turbulent times) and the guy seemed to be trying really hard to feminise me. I'd never thought about doing it really before, but for some reason, when he bought me female clothing I just sort of.. did it. Even shaved myself completely too. And yeah, I liked it. It was only like, wearing panties and stockings, though, not full-on crossdressing I guess.

After that I wore them to work a couple times for a little thrill, which was nice. Masturbated while wearing them a few times and took pictures and stuff, but this was years ago, and as time has gone on i've done it less and less. Maybe it was just a one-off thing, I dunno.
i know this feel all too well

>Summer ends, start high school
>Laura and I go to different schools
>She goes to a super expensive co-ed school, tuition is something like $25K a year, same school Jennifer goes to
>I go to a Catholic all-boy prep school
>Not sure what to expect, figure I’m going to need to tone down my gay mannerisms, be less “swishy”
>Only people I’ve openly acknowledged my gayness to is Laura, Jennifer, and a few other girls from junior high
>Turns out most guys in my grade are pretty chill, quickly become friends with a group of stoners
>They probably wouldn’t care if they knew I was gay, but I really don’t want to potentially be the only openly gay guy in school
>Decide to join the cross country team, figure it’s a good way to stay skinny, determined to keep a twinkish body
>Read on a running website that some runners shave their legs
>Sweet, now I have an excuse to do that
>Go a couple weeks without seeing Laura but we still text daily, she tells me she joined the freshman cheerleading squad and is making friends
>Go over to her house one Saturday afternoon and hangout, it’s great to see her, it’s like nothing’s changed


>A month passes, only see each other once, can’t ever meet up after school because I have cross country practice and she does cheerleader stuff, plus we both have new social groups
>Halloween approaches, she invites me to go to a party with her at some sophomore’s house, says she really wants me to meet her friends
>Wants me to dress up like a cheerleader from her school, thinks it will be funny
>Agree to it, I’m still trying to act as straight as possible at my school but don’t really care about putting on the act for people at her school
>Halloween comes, shave my legs, they look really good from running everyday
>>Go over to her house
>Her mom and Jennifer are there, dad is out of town
>Pretty sure the girls have told their mom I’m gay because she’s totally fine with me getting dressed with them
>Put on Laura’s cheerleader uniform, looks like the pic attached except it’s black, red, and white
>She gives me some nylon dance underwear to wear under the skirt and a padded bra
>She does my makeup, uses glittery lipgloss and eyeshadow
>She bought me new hair extensions, ties it up with ribbons in her school colors
>Look pretty fucking cute DESU, plus my stomach is ultra flat because I’m getting so much exercise


>Laura wears a french maid costume, it’s way sluttier than anything she usually wears, looks really pretty
>>Jennifer dresses up like the Bride of Chucky, wears a frilly white dress with fake blood on it and a leather jacket, looks really awesome
>Tell her I’m jealous of her costume
>Jennifer’s friend comes and picks us up, they’re heading to a senior party and are going to drop us off on the way
>Stop at a liquor store where the creepy cashier never cards hot teenage girls
>Jennifer buys Laura and I a bottle of vodka and some Sprite
>Drop us off at the party, it’s in the backyard of a huge house, apparently no one is allowed inside even though it’s like 40 degrees out
>We walk around to the backyard, find her cheerleader friends and Laura introduces us
>They’re really nice, seem pretty cool, tell me they thought I was a girl when they first saw us
>Group of guys come up to talk to us, a few of them seem embarrassed when they realize I’m a dude but they’re not rude or anything
>Pretty obvious that a lot of guys want to fuck Laura
>We both get pretty drunk
>Cops come about an hour later and break up the party
>Everyone starts scattering
>Laura lives only about a mile away so we decide to just walk back to her house
>Creep back in so her mom doesn’t wake up and see how drunk we are
>Go to her room, lie in bed and watch some shitty horror movie
>Change back into my regular clothes and walk home around midnight
Should have given it to her instead of throwing it away.

Take more?

>Told him I love him he told me the same. I broke contact.

y u do dat? ;_;

Cause hes married
Oh, I thought you were the married one. Still, too bad. Maybe you'll find someone else.

Yeah I know, I felt really bad about it afterward. My parents had just caught me smoking weed, so I was super paranoid that they would start searching my room. I never told her that I got rid of it. It was a small photo album, had like 20 pictures in it. She seriously had like 300 pictures of me in drag, though.
Damn, what a loss.
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Oops, forgot to attach the picture of the cheerleader uniform

For some reason I only want my male friends, I love them though


>Don’t see Laura for about a month, still text a lot though
>She starts dating a guy a year older than us, so she goes out with his friends a lot, plus he can drive and has a car
>Cross country season ends, I start smoking weed almost everyday after school with my new friends
>Some of them have girlfriends from other schools so we meet up with them a lot, they’re pretty cool, kind of hippie-ish though and not the type of girls I usually hang out with
>Laura has some of her new friends over one Saturday night, invites me over
>There’s about a dozen people there, meet her new boyfriend
>He’s nice enough, super preppy and jockish, not really that talkative
>I get along great with her girlfriends though, especially a girl named Lauren
>She’s not a cheerleader, just befriended Laura through class
>She’s really cool, very girly and into fashion, straight up asks me if I’m gay after like 10 minutes, I just laugh and say yes but I’m kind of on the DL so don’t broadcast it
>We end up exchanging numbers, make plans to meet up again in the future
>Laura calls me the next day and says Lauren really wants just us three to hang out sometime
>Jokes that Lauren might have a crush on me even though I’m gay, says she’s into skinny androgynous guys and has complained that there isn’t anyone like that in their grade
>Christmas break comes, Laura invites me and Lauren over to hang out at her house
>Her parents are gone for the day, so we smoke some weed on her back patio then go chill out in her room
>Lauren’s really high, asks me a ton of questions about being gay, say she’s never had a gay friend so she’s just curious
>Tell her I’ve never kissed a guy before, and never even met any other gay guys, besides I’ve only come out to a handful of people
>Laura starts telling Lauren how cute I look in drag, opens a drawer and pulls out a bunch of pictures
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>Lauren LOVES this, goes on and and on about how pretty I look, asks me if I wish I was a girl
>Say not really, I just think it’s fun to dress up
>She asks if they can dress me up now, I say sure
>Laura’s parents are going to be gone for a few more hours, but at this point I don’t even care if they do see me in drag, I mean they know I’m gay and Laura’s mom already saw me dressed like a cheerleader anyway
>Put on a long pink maxi dress, looks just like the one in attached pic (might actually be the same one)
>Lauren does my makeup, she’s really, really good at it
>She says that makeup is basically her favorite thing, spends hours trying out makeup combinations when she has nothing else to do
>Laura does my hair while Lauren paints my nails
>It’s the most convincing I’ve ever looked, I mean I would confidently go anywhere in public looking like that, even in broad daylight
>Jennifer comes home, walks into the room, shrieks when she sees me, walks over and gives me a big hug
>Now that I think of it, she might have thought I was secretly transgender at the time
>We hang out for another hour before I change back to boymode
>Lauren’s still really high, gives me a hug before I leave and tells me she’s so glad that we’ve met and we need to hang out again soon

I'm done posting for the night, will continue the story tomorrow night if I can.
This shit's fake, you've been writing these all day. None of this shit ever happened. "Oh yeah we took like 33282 pictures and all of them disappeared", "Hot cheerleaders made me their secret dress up doll".
Don't listen to that other anon. I'm enjoying this, and no I don't mean fapping. I feel like something adorable is around the corner. At this point I don't even care if it is a fake story, I just want you to continue.
>wearing the other genders clothes
Im sorry, but mens clothing is usually regarded as gender neutral and women's clothing usually has the feminine connotation
>need a warm jacket for the winter
>literally every mens jacket is cut in a way that makes your shoulders look huge
please tell me how this is gender neutral and not masc?
what part of >"usually" do you not understand faglord?
Looking forward to more, these are great.

Fuck off.
Mens clothing is always made to make the wearer look more masc. Your retarded gender neutral argument is just bullshit.
>tfw it's almost that time when I need to break out my warm, but heavy and bulky jacket
I almost want to freeze.
Just go into the womens section and buy a nice warm winter coat instead of the mens trash.
But what if somebody notices I'm wearing a woman's coat? I don't want people to think less of me.
Just don't buy anything flashy and most people won't even notice.
I don't think I'm brave enough to take that chance.
Woman up.
Your loss.
Bitch, fucking, please. a chick can wear my shirt and jacket and nobody would bat an eye
I want to, but I'm living with family and I wouldn't want to complicate things. One of them bought me my current jacket for Christmas a year or two back and they'd ask why I was replacing a perfectly good jacket.
I'm sorry I've failed you.
Are you actually this fucking dense? People would still notice that it's male clothing.
>read thread
>feel sad that I haven't done much crossdressing
I know a quick way to raise my mood would be to order a cute dress with an amazon locker, but that just isn't feasible right now. How do I cope during the long time periods in which I can't get dressed up?
There are tons dress up games online to soothe your mind a little.
I used to do this with mmorpg's, but lately those have lost their appeal. Do you recommend any particular dress up games?
It's been a while but I vividly remember this Kisekae game everyone on /a/ loved so much. You can make a character, pose them, put tons of clothes on them and even import new stuff to get exactly what you want. Not sure if it's still around or if there's something even better now.
Not that anon, but wow, KISS sets. I remember those.
Well that gives me some kind of starting point to go off of. Thanks anon.

Arma 3
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130 KB JPG
>tfw have had a 42'' underbust since i was 15
>tfw will never be able to wear what i want with out looking like a drag queen.
gotta say, the adult man and girl type of incest in the only kind that still skeeves me out
must be some strange internalized preconceived feelings I still have left
I was 4 or 5 when I first started wearing my sisters skirts because my mom thought it was fun and so did my sister and by default so did I

Im 21 now and and the crossdressing thing never went away. In fact it only got stronger.

t-thanks mom and sis
I want to die...

>mother calls sister saying she thinks im acting weird
>she gets home
>comes to my room
>"we need to talk"
>at this point i have literally no idea what she means
>"about this crossdressing thing"
>wish the world would open and just swallow me up

Her knowing sucks so much less than the fact that this clearly hurt her, she had tears in her eyes and was sobbing, its not her fault or anything, its so much more complex than that...i mean, i was just having fun, im not trans, im playing dress up...

i feel so shit right now. Like...i haven't felt this bad in years.
how did she find out anon?
There's no reason you should feel bad, and neither should she.

Ask her why it's such a big deal. How would she feel if her mom freaked out about her wearing pants?
I am still currently trying to figure that out...

That sort of logic isnt going to work here. I dont think she has a moral or ethical objection to it, i think she sees it more like she failed me somehow, its an abnormal behaviour, i think its more of a guilt thing for her.

Theres...history there...absent father, no real male rolemodel, a history of depression in my teens (mine not hers) that she had trouble dealing with as a single mother, i have always been a troublesome child.

Im not sure if i can approach the issue again right now, maybe at some stage we'll talk about it again. I mean...i owned it, i explained i wasnt trans, that i just do it for fun, i think that put her mind at ease a lot, i got the impression she was very worried that i would want to transition...or something.

I didn't say all the pictures disappeared, for all I know Laura still has them all. I feel like you haven't even read most of what I've written. I really don't see what's so unbelievable about anything I've written either. Don't care if you think it's fake anyway, I'm mostly just writing all this out for my own sake and I figure people on here would enjoy reading about my experiences.

Glad you're enjoying it, I'm kind of just writing this all out as a diary. I promise you that everything I've written is true, still have a lot of stories left.
Alrighty, time to tell you about my history of crossdressing from a while ago.
>Be me, 16 year old
>Leave school cause mental health issues, go to psych ward for a bit
>Have been crossdressing for a bit, mostly do it just cause I like looking cute and wanna be a grill
>Only ever do it in private
>Anyway, chill in psych ward for a week
>Meet cool dude in there, 18 years old
>In there for drug problems and family abuse
>Get close to him, seems like a nice guy
>One night we're really tired and there are no staff around
>Decide to tell each other a secret, just cause we'd probably never see each other again
>Count of three, we share secrets
>"I crossdress."
>"I'm gay."
>Laugh it off and he asks me some questions about why I do it
>Tell him I do it to look cute, and cause the idea of being a girl seems nice I guess
>He finds it cute
>We end up talking once we get out of the ward
>One day he asks me what the most annoying thing is with crossdressing
>"Shaving, shit sucks"
>"Oh, I know how to shave real good! I should come over and show you!!!!"
>Wtf is that line
>"Sure whatever"
>He comes over to show me how to 'shave good'
>Actually shows me how to shave properly
>Just sort of sits on the couch for a bit
>Hang out with him for a while, before he suddenly leans towards me
>"Hey, anon...Can you dress up for me..?"
>Hesitate a bit but decide 'why not?'
>Go into room
>Come out wearing long, knitted grey cardigan, pink skirt and black stockings
>Makeup is just basic highlighting and shit with black lipstick
>He's sort of quiet for a bit and just continues watching tv
>Get surprisingly frustrated
>Bully him a bit for wanting me to dress up
>"C'mon man! You get me to embarrass myself like this and you won't even do anything?"
>Ten minutes later he's railing me against the couch
More or..?

Yes, more!
>Ten mins later he's pounding me against the arm of the couch
>Keeps calling me his "Button"
>End up going at it for a good 30 mins, he finishes inside and everything is dandy
>Resting a bit, when suddenly he picks me up
>"Which way is your room anon?
>"Oh, it's the one on the right, that one"
>Takes me to my own room and fucks me for another hour
>Found out things I didn't know about myself
>1, I want to be a girl a lot more than I thought
>2, Cuddling after sex is pretty great
>and 3, you can ahegao irl (Thought it was some kind of hentai meme thing up until he made me pull that face naturally)
>Lie in bed for a bit
>"That was fun, Button"
>Smile at him and just let my fingers wrap around his
>Hear car tires scratching against gravel
>"Oh..that's my Mum"
>Forgot they were coming home earlier than usual
>Guy sprints out to the backyard suddenly, left lying there under the covers
>Two mins later get a message
>"I'll catch you later, Button <3"
>Hug phone for some reason then go about normal daily life after cleaning up and hiding the 'fun times' from my family
>Two days later find out on news and facebook he died to a drug overdose
>Sad that I'll never be called a Button by him again, but whatever.
>Do more crossdressing in private
>Year later, I end up getting into another fun situation in the city
I have a couple more stories, I'll start pre-writing and if you want more just ask.

super hot, def would like to

sounds like the best first time ever desu!
It was alright for my first time, though he'd never tell me when he was cumming, which was annoying.
>Be me, 17 now
>Start an art's course
>Have to start travelling to the city
>Hour by train, so spend two hours on public transport everyday
>Spend almost more time on train than in arts course
>Train is also expensive as fuck for someone who doesn't have a job
>Have to rely on pocket money, and walking past McDonalds and not buying anything makes me sad
>Get a brain blast, jimmy neutron style
>"Oh, I'll just give bj's in the public restrooms or something. People will give me a couple of bucks for that."
>And they do.
>Start off with just a glory hole, but end up enjoying it a lot more than I thought
>Take train an hour earlier to have some spare time before class
>Start trapping up and beckoning dudes into the stalls
>Start getting shit tons of money, more money than I could ever dream of
>Made more money sucking dick than my bro's made working legit jobs
>'Customers' sometimes pay me extra to let them fuck my ass
>Having the best time of my life
>Dressing up as a girl has made me money, let me feel good and be cute
One day though, I stop thinking that.
This story is kind of like the ending to my adventures I guess. I did plenty of other fun things in those bathrooms, but this is what I finished up with. You can ask for those other stories if you want.
>Get one customer
>Give him blowjob, he cums, yada yada yada
>Cleaning up in the mirror a bit when he suddenly gropes my ass
>”Yo…I have a place not far from here..Wanna make a couple’ extra dosh?”
>Shrug shoulders
>May as well right?
>Wrap my arms around his and step out of the bathroom in my trap clothes for the first time
>Leads me from alley to alley
>Get to abandoned office building
>”Welcome to my home!”
>It’s just a bunch of desks with a mattress on top, beer bottles and food cans scattered everywhere
>Cringe a bit but whatever
>Money is money
>Pleasure is pleasure
>Dude and I do the deed
>He, quite frankly, sucks at sex
>Ends up making me cum numerous time though, ended up skipping class without realising
>Have sudden weird thought
>As I’m lying in a pool of my own and some random stranger’s cum, I realise I’ll never be a real girl, no matter how much I crossdress or have surgery
>I’ll never be the girl I pretend to dress up as
>Get really depressed, dude doesn’t care though
>”I’ll catch you later, sluuuuuut!”
>Throws wad of cash on me and walks out of his home
>Clean self up and go back home
>Stop doing crossdressing, haven’t done it to this day
I’ve been fucked numerous guys and lived that fantasy I’ve always wanted, but sadly, I’ll never actually be a girl. Dressing up just feels wrong now. Sorry to end it on a sad note.

I believe you'll get there. <3

Just aim for 300pg/ml estadiol.

Thanks for sharing your stories.
Oh, looking like a girl isn't a problem, it's more the fact of...well, I was born a guy.

No matter how hard I wanna try to change my body, or pretend I'm what I want, the end of the day facts say that I'm not. I CAN chop my dick off and pretend that the giant, gaping wound is a vagina, but that isn't good enough for me. I CAN take heaps of estadiol that will make me seem more feminine, but I'll still be a guy.

Whether I like it or not, I'm a guy. No amount of change can really do anything about that. Though this isn't the thread for that kind of discussion.

Anyway, thanks for the nice words though, and I'm glad you enjoyed my stories <3

Sincerely, Button, I guess?

'One is not born a woman, but becomes one', as that old saying goes...

Laters, Button!

But you are a girl, you just haven't adjusted your body. As a girl, though, I hope you gain a little more self-respect. Dress up again, take your hormones, and look for dates instead of clients.

Yeah....On the one hand you seem very resigned, yet on the other I'm pretty sure if this was as settled as you present it then you wouldn't have told us your tales on /lgbt/....Wish you all the best!
You replied to the wrong person.

Didn't want to reply to her in the third person when she could read it, did I?
you did hours of buttfucking on your first time? nice fantasy but this is totally made up

Lived with single mother, so it was easy to find time alone.
I was about 3-5 when I got caught wearing her earrings, shoes and dress, and she banned me from her closet.

Pretty sure she blocked that memory herself.

OK, time for me to continue the story. I first just want to clarify one thing for those of you who think this is all fiction- none of my experiences as a teenager are unusual. I have several gay friends who say used to dress up with their girlfriends all the time in high school, too. Earlier I mentioned that Laura and Jennifer wanted to take me to Sephora to get a makeover, but I was too afraid to do it- well, I have a friend who says he actually did that at least a dozen times. If you’re a twinkish young gay guy who wants to dress up like a girl, just mention it to any of your female friends and I promise you that over 90% of them will be happy to help you out. You know that teenage girls are obsessed with drag queens, right? They’re like the top demographic for Ru Paul’s Drag Race.

I went to a Lady Gaga concert a couple years ago, and I saw a TON of teenage gay boys dressed in drag, dancing with their girlfriends. Girls LOVE this stuff. Seriously, if you’re a young gay guy who wants to have the same type of experiences I had as a teen, just grow a backbone and tell some female friends that you want to do it. I guess the only exception would be if you live in a super conservative Christian area, then yeah I could see it maybe not going over so well.


I guess I’m just writing this to inspire some of you. You’re just denying yourself some awesome experiences and memories if you keep your desires all bottled up. I literally get teary-eyed looking back at my high school years, because I know I’m never going to have those same experiences again. Laura, Lauren, and I are all 26 now, and both of them recently got married and we each live 1000 miles apart. We’re never going to have back those times we spent together as teenagers. Some of the most fun times I ever had in my life were getting drunk with them and dressing up in fun outfits, dancing around and acting stupid. When I hit my 20s I would dress in drag, take MDMA, and go to raves, and I can honestly say even doing that wasn’t as fun as some of the stuff I did with my two best friends in high school.

Now back to my story...

>About a month passes, start texting with Lauren regularly
>Laura is busy doing stuff with her boyfriend, but tells me that she’s not sure she likes him that much anymore, says he and his friends are kind of boring and they don’t really have much in common
>Lauren invites me over to her house a couple times, but she lives all the way on the other side of the city and it’s like a 35 minute drive, parents won’t drive me that far just so I can hang out with a girl


>Spend most of my free time with friends from school, they’ve noticed that I never talk about being attracted to any girls, don’t make too big a deal about it though
>One of my friend’s girlfriends (Danielle) says she wants to set me up with her friend (Susan)
>Shit, how am I going to get out of this
>Danielle invites a bunch of people over to her house one night, Susan is there
>Cute girl, she seems into me, I enjoy talking to her but try not to lead her on
>Later that week, friend at school tells me that Susan likes me a lot
>I just say yeah she’s cool, then change the subject
>Few days later, Danielle texts me and asks what I think of Susan
>Consider maybe dating her for a bit just so no one gets suspicious of me, but seems like it would be more trouble than it’s worth
>Text Danielle back that Susan seems nice but I’m not really looking to date anyone right now
>Few days pass, my friend tells me that Danielle thinks I might be gay
>I pretend to be offended and just say I’m not really into Susan
>“But dude she’s hot” he says
>I change the subject
>A couple weeks later Laura calls and tells me she dumped her boyfriend
>Thank God, now we can start hanging out more
>She says that a girl from her grade is having a party that weekend, asks if I want to go, says it’s only like a 20 minute walk from her house, plus her parents are going out that night so we can drink at her place beforehand, Lauren’s coming over too


>Saturday comes, I head over to her house
>We hang out in Laura’s room while the girls get ready, just waiting for her parents to leave so we can start drinking
>Lauren’s wearing a really cool, expensive-looking black mini dress, tell her how much I like it
>She asks if I want to try it on later
>Of course I do
>Laura’s parents finally leave
>We get drunk, blast pop music, dance around, act stupid
>Don’t leave until a couple hours later
>We get to the party, there’s probably 200 people there, parents must be out of town because the house is getting trashed, I don’t know anybody except for a few of Laura’s friends from cheerleading
>Laura goes off and mingles, she’s clearly pretty popular at her school
>Few guys start hitting on Lauren, she’s nice to them but obviously not interested
>Tells me she doesn’t really like most guys in her grade, asks if I have any hot friends at school she could date
>I tell her that all my friends are scruffy stoners who listen to Phish
>She laughs and says no thanks
>We go out on the balcony, talk to some people she knows
>Most people I meet are pretty nice, all the dudes are super preppy though, the type of guys who play a lot of golf, they’re all really drunk
>Cops show up, everyone starts clearing out, see a few people being put into handcuffs
>I have weed and a pipe on me, need to get the fuck out there
>Laura comes outside and finds us, we head back to her house

was never "caught" because my mom did basically what's in your picture, just not to that extent, I only do it very rarely now, I still pass except my voice, so I just don't talk

>Thankfully her parents are asleep
>It’s only 11, my curfew isn’t until 1 so I can hang out for a bit
>We go out on her back porch and smoke a bowl
>Go up to Laura’s room, it’s on the other side of the house so her parents can’t hear us, good thing because we’re all drunk and blazed
>Lauren asks if I want to try on her dress now, I say sure
>She takes it off, gives it to me and changes into some other clothes she brought
>I put the dress on, it fits perfectly, feels really sexy
>Lauren asks if she can put makeup on me too, Laura laughs and says you don’t even need to ask, he’ll always let you
>She’s right
>She spends the next hour or so doing the makeup, makes it look really smoky and elegant, totally different look than I’ve ever had before
>Laura breaks out the hair extensions, we talk about how we need to get me a really nice wig someday
>Lauren says she has a few at her house I can have
>We pose for a few pictures
>Shortly after she’s totally done with the makeup I have to leave to make curfew, take the dress and makeup off, put my clothes back on
>Walk home, kind of sad that I’m not able to dress up more often, but feel really lucky that I have such cool friends


>A few weeks pass, sitting in a park after school on a Friday, getting high with some friends
>Danielle is there, is acting kind of bitchy, obviously mad that I rejected her friend
>Laura calls my cell phone, says she’s over at Lauren’s house and they want me to come over
>Says they’ve been telling Lauren’s mom about me and she really wants to meet me
>Say I can’t, don’t have a ride
>Lauren yells in the background, “Tell him we have wigs he can try on!”
>Everyone at the park looks at me weird, I think they heard her say that, the volume on my phone was too high
>Laura says she’s going to spend the night at Lauren’s, says she’ll call me tomorrow
>Hang up the phone, someone asks what was that about wigs, I say I don’t know what you’re talking about, you must have misheard
>Next day, go over to Laura’s house in the afternoon
>She tells me that Lauren has the coolest mom ever
>Says she’s just like Regina George’s mom in Mean Girls but not annoying, doesn’t act like a typical mom at all, is super nice and you can talk to her about anything
>Says she’ll let us drink as long as we don’t drive anywhere
>Just Lauren and her mom live in a really nice house, she has an older sister too but she’s a freshman in college, Lauren says she’s a huge bitch
>Fun fact: her sister later went on to pose nude in Playboy
>Apparently Lauren’s dad worked in finance, made a ton of money and retired in his 40s
>Lauren’s mom was basically a trophy wife, got married when she was 24, is 12 years younger than her dad


>Dad got caught having an affair, Lauren’s mom divorced him and she got millions of dollars in the divorce and the house
>Dad moved to South Florida and married his mistress, some woman in her mid-30s
>Lauren hates her dad, but he gives her a huge monthly allowance because he feels guilty about everything
>Lauren’s mom works just a couple days a week at her friend’s art gallery
>Basically has an amazing life, just works out and goes shopping most days
>Laura says when she gets her driver’s license we’re going to start hanging out at Lauren’s house all the time, we can swim in her pool too when the weather gets warmer
>Another month passes, Lauren has started dating some sophomore guy from school, loses her virginity to him
>Laura and Lauren go out with his friends every weekend, they invite me to come with them but I never want to tag along
>Hang out with school friends, pretty sure they’ve started suspecting I’m gay but no one gives me any shit
>Usually go over to Laura’s house on Sunday afternoons and we watch movies in her room
>Don’t do much dressing up, sometimes when Laura gets new clothes I’ll try them on if they look particularly cute
>Sometimes I practice doing makeup when I’m there, still pretty bad at it but I’m slowly getting better
>Lauren eventually dumps her boyfriend, few days later Laura gets her license and her parents buy her a car

>Lauren invites us to come over one Saturday and swim in her pool
>Says her mom will let us drink if we spend the night, but Laura has to go home that night because her aunt is coming in town or something so we can’t
>Laura picks me up around noon, we drive over
>Lauren’s house is amazing, it’s a huge, modern ranch-style place sitting on a hilltop
>Ring the doorbell, her mom answers the door
>She’s absolutely gorgeous, is 44 but looks 34, looks A LOT like Jenny McCarthy, including the breast implants
>She’s excited to see us, says she’s heard a lot about me, is super friendly
>Goes to tell Lauren we’re there
>Look around the house, everything is ultra-modern and there’s really cool artwork everywhere
>Lauren comes out, we hang out with her mom in the living room for a half hour or so, she’s very talkative and asks me a lot of questions about myself, seems genuinely interested in my answers
>Compliments me for being so skinny, she’s the first adult to actually do that, normally I get a lot of shit for it
>Says she has to go run some errands but to help ourselves to anything
>We change into our swimsuits and go out to the pool
>Swim around a bit, then just hang out in deck chairs, feels pretty luxurious
>I ask Lauren if we can smoke weed out there, she says her mom doesn’t care and will just look the other way
>I roll a couple joints and we lay in the pool on inner tubes and smoke them, Laura doesn’t smoke though because she doesn’t want to drive high
>Have a nice afternoon, Lauren’s mom comes home right as we’re about to leave, gives us both hugs and says we’re welcome anytime
>Summer break starts a couple weeks later, Lauren texts me and says she’s going to host a girl’s night at her house and I’m invited, just going to be a couple girls from her high school and a couple girls from her old school, says everyone’s spending the night


>Tell my parents I’m spending the night at a dude’s house
>Walk over to Laura’s around 6 and we drive over
>Laura’s mom (I’m just going to use her name, Natalie, from now on) answers the door, she’s wearing a robe and her is wet, has a fresh face of makeup on
>She hugs us, apologizes for being in a robe and says she has to go to some charity party at some museum tonight and is getting ready
>Asks us if we’re spending the night, we say we are
>She says good, tells us there’s plenty of booze in the kitchen, just please don’t get alcohol poisoning otherwise she’ll get in trouble
>We mix up a couple drinks and go outside
>Lauren and three other girls I’ve never met before are sitting around a table, Laura knows one girl from school
>They’re all really cool and nice
>We sit around and drink, they mostly gossip about boys at their school
>Lauren tells us in graphic detail about what it was like to fuck her ex-boyfriend, it’s pretty hilarious
>About an hour later I’m a little drunk, go inside to pee
>Natalie’s in the kitchen talking on the phone, she’s wearing a long silver sequined gown and diamond jewelry, her hair all done up
>She hangs up the phone, I tell her she looks gorgeous
>She asks me if I want to have a glass of wine with her while she waits for her friend to pick her up, I say sure


>We go and sit on a couch in the living room, I ask her about the art she owns, she tells me a little about it
>Says she’s really glad that Lauren has a gay friend, she normally can’t stand teenage boys but she likes me a lot
>Asks me if I ever met Lauren’s ex-boyfriend, I say no
>She says she told Lauren he was an idiot, but of course she went ahead and fucked him anyway
>I burst out laughing, say wow I’m surprised she told you about that
>She says she’s just glad that Lauren made him wear a condom
>Asks me if I’ve ever had a boyfriend, I say no
>She tells me not to worry, she knows a bunch of rich gay guys she can introduce me to when I’m older, I laugh
>Says she has a ton of gay friends, the owner of the gallery she works at is gay
>Starting to feel pretty drunk from the glass of wine, I start to open up and tell her about how I’m kind of living a double life, how my parents don’t know I’m gay but they probably suspect it, how I don’t want anyone from my school to find out, etc.
>She’s being really sweet and supporting, actually holds my hand
>I tell her how cool she is, that Lauren is lucky to have such a cool mom
>She seems really flattered, I ask her about her dating life
>Says that it sucks, thinks a lot of guys her age are boring, she usually just goes out with her girlfriends and gay friends
>Tells me she doesn’t want to go to the charity party tonight but has to because her friend is hosting it, says she’d rather just stay here and hang out with us
>Her friend’s car pulls up in the driveway, says she has to go, asks me to tell Lauren she’s leaving
>reminder that this is a crossdressing thread, if you're a mtf tranny post boymode stories
Lauren’s mom sounds awesome

She really is an amazing person, by far the coolest adult I knew as a teenager. We became really close, she would even call me when I was in college sometimes to check up on me. But I'll get into more detail about that later, I'm typing up the rest of the story now
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you guys are gay

>I go back outside to sit with the girls, decide to take a little break from drinking because it’s still early and I don’t want to pass out
>Wait about an hour to sober up a little, go out to Laura’s car and grab the pipe and weed I left in there
>Join the girls again, we smoke a few bowls
>Two of the girls have never smoked before, they get extremely high and start saying ridiculous shit, it’s really funny
>About another hour passes, we’re all pretty fucked up at this point
>Natalie’s’ friend’s car pulls into the driveway, Natalie gets out and opens the gate, she’s obviously drunk, wobbling in her stilettos
>She sits down with us, sees the pipe and asks if she can hit it
>We all laugh, Lauren seems pretty shocked, didn’t even know her mom smoked weed
>She takes a couple hits, we ask her how was the party
>Says it sucked, she and her friend left after an hour and went to a hotel bar
>She hangs out with us for a bit, then gets up and says she really needs to pee
>Goes inside, about 10 minutes later opens the door and yells to Lauren to come inside for a second
>Lauren goes inside for a few minutes, comes out laughing, says that her mom wants to talk to me


>I walk inside, Natalie says that she heard I like to dress up like a girl
>Say yeah I do it sometimes, kind of embarrassed in the moment
>She tells me not to be embarrassed, she thinks it’s great
>Tells me to follow her, she has a surprise for me
>Takes me to her bedroom, go into one of her two huge walk- in closets
>She grabs a few boxes, takes out three mannequin heads with wigs on them
>Says Natalie told her I needed a nice wig, says I can have one of these, they’re made out of real human hair
>I’m blown away, these probably cost a few grand each
>I ask if she’s sure, she says she wants me to have it, I’d get way more use out of it than she ever will
>Says she bought them for costume parties but they haven’t been used since
>I give her a hug, say thank you
>I pick a long brown one
>She asks me if I want to get dressed up and try out the wig, surprise the girls
>I say OK


>She takes me over to her other walk-in closet, she has like 100 dresses in there
>Asks me what my dress size is, say I’m not sure but I know I fit in a size 4
>She starts flipping through the dresses, says I can wear one of her expensive gowns
>Tells me to pick one out
>Takes me a while to look through them all, pick a blue one-shoulder Armani gown
>Says she’ll go grab me one of Lauren’s bras, since obviously hers won’t fit me (breast implants)
>Comes back with a strapless bra and a couple silicone inserts, she says they’ll make me look like I have real boobs
>Goes to her other closet, pulls out some black panties with the tag still on, says I can just keep them, she’s never worn them
>This whole situation is so surreal, but I love it
>Thank her again, she says no problem, this is a lot of fun for her
>Tells me she used to be friends with a couple drag queens before she got married
>She leaves the room, asks me if she can smoke some more pot, I tell her to help herself

>She grabs the wig and says she’ll have Lauren brush it for me
>I get undressed, put on the bra and panties, put in the inserts, slip on the dress
>Check myself out in the mirror, the dress is so pretty, think that this is probably the most expensive thing I’ll ever wear
>She comes back in the room, says she told the girls they can’t see me until we’re finished
>Says I have great legs, she loves that I shave them
>I sit down at her vanity, she has sooo much makeup it’s insane
>She tells me she’s way better at makeup than Lauren, by the time she’s finished I’ll be breathtaking, I laugh
>Says this is going to take a while, jokes that the girls might be passed out by the time she’s done
>She really is talented, uses a bunch of products I’ve never even seen before
>Hear the girls come inside, they go in the living room and start blasting music, some of them come over to take a peek, Natalie tells them to get the fuck out and slams the door
>She gets me a glass of wine, tells me a ton of funny stories about her party girl days
>I’m having so much fun I can barely stand it
>Whole process takes about an hour, she then goes out and gets the wig
>Gives me a cap to pull over my head, puts the wig on
>Oh my God I look beautiful

>She styles it into an elegant-looking updo, puts a ton of pins in it
>Tells me I look like Audrey Hepburn
>Goes to the closet and gets me some heels, not sure if they’ll fit me but they do
>My God I look so hot
>She opens the door, tells me to go show the girls, they all love it
>Natalie grabs a camera, takes a picture of us all together
>I hug her and tell her thank you so much
>We spend the next hour or so hanging out in the living room, smoke more weed
>One by one the girls start passing out
>I’m so amped up I couldn’t even sleep if I wanted to
>Natalie stays up with me, she asks if I brought anything to sleep in, I say no
>She brings me some white silk pajamas to wear
>I go in her closet to change into them, hand her back the dress
>The pajamas feel amazing on my skin
>She helps me take the makeup off
>I go lay on the bed in their spare bedroom
>Natalie brings me some water, kisses me on the cheek and says goodnight
>My God, this woman is so amazing
>I fall asleep

[to be continued]
is it bad or off topic to say that as a big burly man i still like wearing cute panties when i fuck crossdressers? it just turns me on but i have no illusions about looking sexy on me, i just like the feeling
i've come across chasers who look for cd's and it seems like they'd cd too, but just too masc to girlmode/trap in public
hmm interesting, well at least i'm not super weird
so have you met any passable trans or cds irl?
one that went by Samantha (I think their old name was Sammy since they had a birthday card in their room addressed to them when they were a kid) that I dated for a year. She was hot as fuck even if a little flat in the ass area, wore lots of sexy stuff and loved to get stuffed
These stories are amazing.

>tfw no pretty gayboy to dress up like your own living doll
For a while I was exchanging pictures with a guy who was kind of big. He liked dressing in panties and so did I. We exchanged all sorts of pictures from just wearing panties to fucking ourselves in the ass while dressed up.

There's plenty of guys like you and me out there.
Pretty neat, it does make me feel a lot more secure in my dastardly fetishes
Yeah, knowing there are other guys like you out there is nice.
What the fuck
It should skeeve you out you fucking lemon
Stop LARPing faggot
Was unbelievable to begin and then you went for the ultimate tranny fiction memes of 'runners shave their legs' and 'friend joined cheerleading squad'
Sometimes I like to dress up in drag or full on brolita, go to bars on karaoke nights, and do full on ghetto rap. That makes for a lot of fun.
Fuck off. Just because you haven't lead an interesting life doesn't mean everyone's is boring.
If you genuinely believe that load of tripe I've got a bridge to sell you
No one cares.

If they're fake stories, at least they're entertaining. Go whine elsewhere.
Well then he can tell them without about fifty posts of 'Oh I promise they're true!!!!' and having retards fawn at them
You just sound like a boring, whiny cunt. I have a few friends that have been into all kinds of crazy shit that I'm sure you'd say sounds fake too, but since you're just a retard on a Vietnamese pixel exchange market, you wouldn't know, would you?
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Oh look, here's that bridge I was telling you about
>/poltard/ jealous that no milf feminized him
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K bye
>desperately want to get dicked
>moved into my own place
>start wearing girl clothes at home exclusively
>find guys online to hook up with
>fantasize about them hiking up my skirt and ravaging my boypussy
>go to the meet up place
>get nervous and chicken out
>rinse and repeat

reeee how do I get over the hump?
drugs and alcohol
Invite them over I guess. Harder to chicken out if you're already dressed, a bit drunk and he's knocking on your door.
>give random dude his home address
>chicken out again
>dude is banging on the door
>breaks in

Good job, you just got that guy raped
That's a good incentive to not chicken out though.

I'm guessing that you're a frustrated straight guy with a crossdressing fetish who is completely ignorant about gay male/straight female relationships. Also what the fuck is so unbelievable about an attractive girl joining a cheerleading team? Do you really not realize how common that is?

I think you're just jealous that gay guys can get away with doing thing that you can only fantasize about.
>just grow a backbone and tell some female friends that you want to do it
>tfw 23
>tfw missed my window to be a happy femboy, having with with girlfriends

Thanks for sharing your stories, I love hearing about your experiences!
>be freshman college
>living with couple off campus
>work two jobs
>one day just get let go from one of them
>barely enough money to make rent now
>end up having to borrow money from roommates
>feel really bad
>apologize to the girl one day
>she super friendly but says we could work something out
>says boyfriend really really wants to have a three some
>I'm totally surprised, didn't see anything that would imply he liked me
>be into crossdressing and traps but never actually considered it
>tell her I'm really not sure
>she offers to cover half the rent
>agree cause holy shit that'd be so nice not to have to pay that
>ask when, she says on friday
>friday comes
>crazy nervous
>watching TV on the couch with them and they start making out
>she suddenly grabs my hand and then leans over to kiss me
>he tells her to stop
>my heart stops cause he sounded upset and the guys was jacked and could easily kill me
>tells her to take me into their room and get me dressed in her cloths
>we do, I get put on her old high school prep uniform, fits cause we're almost same height
>she calls him in, we start making out on the bed, her on top and kind of gentle femdoming, him watching
>first time for me kissing, absolutely loving it cause I had a crush on her
>flip over so on top, think nothing of it
>suddenly she moans really hard
>look back and see that him naked and off her pants and panties off and was now pushing inside her
>heart starts to race and start to feel uncomfortable
>she probably saw this cause she wrapped her arms around my neck and pulled me into a deep kiss
>making out with her while he fucks her
>easily hottest thing in my life
>can't even think, just experience emotions
>her tongue is all over mine
>feel hands on my ass as he pulls her skirt up me
>I hadn't put any underwear on
>feel pressure on my cheeks
>realize he wants to fuck me
>was still really nervous and hoping he just wanted me there to watch (naive as fuck)
>break the kiss and look worried at her, just say I don't think I can
>she says please just try
>he tells me it'll feel good
>bite my lip and say okay
>he starts to push in
>feels like a massive baseball bat going inside
>hear him say damn you're tight
>chicken out and pull forward and say I can't do it
>try to get up and she grabs me and says wait
>see her stare at him for a few seconds before asking me if I'm a virgin
>think they ask because I'm scared and chickening out, learn later they both have a huge cherry popping fetish
>she offers to pay all of my rent if I let them fuck me
>I'm quiet for a few seconds before saying asking if she promises she will
>they both answers yes like immediately
>I say okay
>they both thank me, she kisses me hard
>lay back down again before they pull me up on hands and knees
>she pulls my skirt down and tells him to take it off
>she widens her legs tells me to wait
>feel him pushing in hard again
>both of them are saying sweet things like "it's okay baby" he sounds like how he usually talks to her
>gets really far in and tells her I'm ready
>she lines up my cocks with her pussylips, I'm barely inside
>she counts down from 3
>gets to one and then says go
>both of them push inside
>I let out a really loud cry/whimper/moan
>both my cherries broken at the same time
>he starts to slowly rock inside me while she just takes me all the way in
>wraps her legs around me and just keeps saying encouraging things
>my face is scrunched up cause he's huge and barely moving inside me
>after what feels like literally forever I feel his balls against mine
>she's fucking me hard at this point and tells him, "Come on baby!"
>he says I'm so tight he's trying not to come
>swear I can feel my stomach bulging as he's just waiting there
>she asks really and he says yes
>she tells him to wait and starts to go faster, says we'll come at the same time
>I'm starting to feel really fucking horny now that he's not moving
>feel my own orgasm approaching
>she grabs my face and kisses me before telling me to cum
>say almost and a few seconds later feel it hit me like a truck
>don't remember what happened at this point, just blank out as they both cum
>cum to laying on her with him on me kind of supporting himself
>he pulls out and I shudder hard, making them laugh
>go to try to get up and she tells me to squeeze tight and run to the bathroom and sit on the toilet
>still act like a fucking virgin and not realize why just do it
>hear them laugh and feel myself blush as I wobble to the bathroom
>sit down and relax and feel a huge amount of cum fall out of my ass
>tfw also 23
>tfw I had repressed everything for years
>tfw still living at home with little privacy and too ashamed to buy girl clothes
>they ask if I'm okay and I call back yes
>get up and look in the mirror
>kind of surprised at how much like a girl I look
>actually feel really fucking happy suddenly
>walk back out there and both of them ask how I am
>they are being really sweet and I said fine
>they said they are going to have sex again
>ask if they want me to again too
>they say no that I'm probably too sore and to go shower and get some good sleep
>say it kind of like they were doting on me and I go to leave and girl suddenly tells me to weight
>goes to her closet and comes back some old pajamas
>tells me to sleep in these
>thank them both and go clean up
>fall asleep to the sound of them going fucking crazy in the bedroom
can continue if you guys are interested
yes this is hot desu
>wake up next morning and feel amazing
>see myself in the mirror in pajamas again and smile big, loving this
>go out to eat breakfast, they come out soon after
>she's sweet and wraps her around around me, asking how I am and calling me "sweetie"
>I tell her good and she says I look cute in the pajamas
>he tells me I felt amazing last night
>ask "really?" and he says absolutely, like a real girl
>blushed like crazy, they exchange a look and she tells me they had an idea
>said that his job was going really well and they are really doing good financially
>they exchange another look and she says they would pay for all of my rent every single month
>but in exchange I have to sleep with them
>ask how often
>he goes to say something but she blurts out, "Whenever we want,"
>he says her name implying it was going to be much less than that but she shushes him
>she continues and says that I wouldn't have to look for another job and could just focus my extra time on school
>bite my lip and think about it
>like a dream come true financially but felt really slutty
>say okay
>she claps and gets really happy, kisses me big
>tells me to eat up and get ready for class, acting maternal again
>shower, go to class, after class have work, come home exhausted
>heart is now racing constantly while I'm home thinking they'll want to do something
>he says absolutely, like a real girl
Things That Actually Happened!
>watching TV that night while she was working and tell him that I'm honestly surprised they didn't ask me to do anything
>he laughed a little and said they wanted to but I came home looking exhausted
>felt oddly sweet
>he gets up to make some food
>watching TV still and he calls me and says he made something for me
>it's a salad but actually looks good
>ask why
>says they just wanted to get me some good food to keep my body looking nice
>blushed and eat
>ask him what exactly I am in all of... this
>he thinks for a minute and then says it's like a weird mix of being kind of like a girlfriend, kind of like their maid, and kind of like their pet
>still eating and he asks if he can ask me something
>did that stupid, "You just did," line
>he scoffs and says that the "sex whenever" was her idea and that he didn't really get anything
>say I kind of figured but what did he want
>says he wants me to always dress up like a girl around the house and grow out my hair
>sounds perfect to me cause I figured I'd get to borrow her cloths
>was right, he went and got me an outfit, said they'd buy me better stuff later, that she would "love that"
>eat, chat a bit more, then go to bed
to be fair he said it knowing it sounded cheesy and winked at me jokingly
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ITT old hons fantasize about being young and desirable

OMG you haven't missed any opportunity, I had female roommates from 21-24 and dressed up constantly
>sleeping in cause sunday
>wake up and take shower like normal
>jitters of our arrangement had settled down
>suddenly hear my door open
>it's him and he's naked
>ask him what he's doing there
>he said she's too tired so he's going to use me
>steps into the shower
>my heart is racing like fucking crazy and I'm covering myself and blushing like mad
>he's said come on we had a deal, plus I promise it'll feel good
>feeling really embarrassed but comply and walk closer
>he grabs my waist and kisses me
>actually surprised at how much I felt with it
>wrapped my arms around his neck
>he starts nibbling my lips, causing me to moan
>uses that to push his tongue inside
>says stuff like "you are so hot"
>make out again longer than I can remember before he starts nibbling my neck
>reaches down and pulls up a lube bottle
>ask when that got there
>he says they put it there when I was gone
>starts rubbing it on my ass and playing with me
>fingers go between my cheeks and prod my hole
>whimper when he pushes his finger inside
>does it actually pretty quickly
>keeps lubing up my asshole
>actually have the thought that he might be using all the bottle
>he starts nibbling and sucking on my nipples
>drives me up the fucking wall
>then he grabs me gently before hosting me up onto the wall
>tells me to hook my legs around him
>only get one so he just holds the other one
>I'm braised against the wall, feet not touching the ground
>his cock is erect and massive
>he slowly lowers me on it
>still really fucking tight
>gets it in though
>just continues to let gravity do the work while occasionally thrusting
>soon all the way in
>starts to fuck me
>feeling of his cock sliding in and out is amazing
>moaning like crazy
>end up orgasming pretty fucking quickly cause he was playing with my cock
>doesn't stop fucking me
>actually ends up being a little uncomfortable after cumming
>finally he grunts and pulls me all the way down
>let out a small eep as he shudders and comes inside me
>I'm not trans but I'm trans
>we stay like that for a bit before he pulls out
>feel the cum slowly leak out and go down my leg
>he thanks me and leaves
>I'm standing there catching my breath
>legs shaking a bit
>take my time until the hot water runs out and turn it off
>drying off and here the door open again
>it's her and she doesn't even say anything, just grins like the Cheshire cat and leaves some cloths on the counter
>I get out and check and it's a really, really fucking short pink skirt and a red thong with just a plain white camisole
>walk out to the the family room, she calls me sexy and laughs at the slight wobble I have
>sore as fuck, she says I'll get used to that
>he comes out dressed for work and kisses her goodbye
>say bye and get surprised when he stops and kisses me goodbye too
>she says cmon I'll make you breakfast with that same giant smile
that's pretty much it, everything else it just a collection of random shit until I transferred to another school. We met a few times, they surprised me once on my birthday and fucked the shit out of me

Also you're welcome, I just got home from work and am going out to dinner with some friends shortly but I'm probably not staying out too late, I'll post more stories tonight if I have the energy. Next story is a fun one
I feel like I just read a Netflix Original series.
That's fucking hot.
Is it rude to ask a crossdresser to keep on most of their outfit during sex? the idea of keeping their lingerie on is so arousing.
An AGP might well want to keep it on if she's having sex with a guy so she doesn't feel gay.
do 3 year olds even have a concept of gender/sex yet?
i dont think you can be a tranny if you dont even know what gender is
Post more stories, bb.

OK, time for more stories.

>Wake up the next morning, Laura is sleeping next to me
>Still amped up from the night before, luckily I’m a teenager and don’t really get hangovers
>Have to pee really bad, walk to the bathroom
>Lauren, Natalie and the two other girls are talking in the kitchen
>Natalie is making everyone smoothies and coffee
>Tell Natalie that was really fun, thank her again for the wig and letting me wear her outrageously expensive gown
>She says you’re welcome and I can try on her clothes anytime I want
>I tell her I’m just going to leave the wig here, don’t really have anyplace to put it at my house
>Laura wakes up and joins us
>Hang out for a bit, Laura and I get ready to leave
>Natalie pulls me aside and gives me her cell number, says she wants me to call her if I need to talk to an adult about anything difficult or end up in a bad situation and don’t want to tell my parents
>Realize much later that she was talking about gay sex
>She gives me a hug and we leave
>I get home, realize I’m still wearing the panties Natalie gave me, hide them under my mattress
>Next day, Laura starts a new job working part time at a hair salon answering phones
>My parents leave the following day to go to Hawaii for 10 days, they fly my sister in to stay with me while they’re gone
>My sister and I aren’t particularly close but we got along alright, plus she really couldn’t care less about what I do, will be nice to not have to be all sneaky about where I go for a while
>Lauren’s birthday is in a few weeks, that night she texts Laura and I, says her mom will buy us tickets to to the Gwen Stefani concert in a few days as an early birthday present, she knows someone who can get us good seats
>Fuck yeah, I love Gwen Stefani

>About an hour later I realize that I could easily go to the concert in drag
>Would be the perfect place to be dressed up at, place will be packed and the crowd will probably be 90 percent female
>I text the girls and ask them what they think
>Lauren loves the idea, says we should all wear sparkly mini dresses, she has a ton of them
>Laura says for sure
>Awesome, I’m excited
>Next day, Lauren calls and asks me if I want to go to Nordstrom to get new heels for the concert
>Tell her I doubt I can afford shoes from there
>She says she’ll buy me some
>Girl no, your mom just gave me a $2500 wig, I can get heels someplace cheaper
>She says shut up, her mom was never going to wear that wig again anyway, besides she’s probably smoked $200 worth of my weed by now anyway, she and her mom are going to come pick me up
>Fuck yeah, I’m getting heels from Nordstrom, plus the odds of me bumping into someone I know in the women’s shoe department there are basically zero so I’m not worried about it
>Remember that Lauren’s dad gives her like $1000 a month allowance so this is nothing to her
>Natalie picks me up about an hour later, she’s going to drop us off at Nordstrom then go to a yoga class

>On the way Lauren says she’s planned out our outfits for the concert
>I’m going to wear a silver dress, she’s going to wear a gold one, and Laura’s wearing green, already has a pair of heels picked out for her
>Natalie tells me she’s going to do my makeup and they’re going to run a curling iron through my wig, says I’m going to look so cute
>We get dropped off, head to the shoe department
>We check out the silver heels, Lauren says I should go for three inches, any bigger and it will be hard to dance in them
>Salesgirl asks if she can help us, Lauren says my friend is a drag queen and needs heels
>Salesgirl laughs, tells me to take off my shoes and she’ll measure my feet, she’s really cool about it
>Lauren picks out three different pairs for me try on
>They’re all between $180 and $220, I ask her if she’s sure, she tells me to shut up about the price, it’s no big deal (Lauren says “shut up” A LOT, it’s like her signature phrase)
>I try them on, walk around the store
>A couple women walking by see me and laugh, I don’t care
>We pick out a pair for me, then Lauren tries on some gold heels
>She picks out a $300 pair for herself
>Damn, money really is no object for her
>She then says we should get me some new underwear too, the dresses are pretty skimpy and I should wear extra tight panties to hide my bulge
>She buys me a couple pairs of panties and a bra, I offer to pay for some of it and she says no
>Natalie picks us up, drives me back to my house, I ask Lauren to hold onto my stuff for me
>She says I should keep the heels and practice walking around in them, I need to get good at it if I want to pass as a girl at the concert, Natalie says she’s right and I need to remember to take small steps and walk with one foot in front of the other
>I say OK, good thing my parents are out of town

>My sister is out visiting friends so I have the place to myself, spend the next couple hours walking around in the heels, eventually feel like I have the hang of it
>Spend the next day smoking weed and watching movies, tomorrow is a big day, first time going out in public as a girl besides Halloween (and that doesn’t really count)
>Whenever my sister leaves the house I practice walking in the heels
>Wake up the next day, I’m giddy with excitement and a little nervous
>Wait until a couple hours before Laura picks me up to get in the shower, shave pretty much my whole body
>Rub some of my sister’s lotion all over myself, use some of her moisturizer on my face, pluck my eyebrows
>Text my sister, tell her I’ll be gone all night, won’t be back until tomorrow
>Laura pulls up, I grab my heels and get in the car
>Get to Lauren’s house, Natalie gives me a big hug, says she’s really excited for me
>Lauren and Laura go to her room to get ready, Natalie takes me to her room
>Tells me to go into her closet, hands me the bra and panties Lauren bought me, tells me to put them on, closes the door and asks me if I want a drink, I say yeah
>She says she left me a robe on the bed and to put it on when I’m done with the underwear
>Walk out of the closet, put the robe on and sit at the vanity
>She comes back, hands me a vodka tonic with a straw in it
>Says that Lauren wants us to all have glittery makeup that matches our dresses
>She really takes her time, takes like an hour and a half, says she wants to make it perfect

>She hands me the silicone bra inserts, tells me to put them in
>Lauren and Laura come into the room, they’re wearing their dresses and have fresh makeup on, they look gorgeous, are already kind of drunk
>Lauren hands me the silver dress, asks if I like it, I tell her I love it, it’s so pretty
>Looks like pic attached
>I start to walk to the closet to put it on, Laura laughs and says you’ve seen us in our underwear, why can’t we see you? We’re all girlfriends here
>Guess she has a point
>I take the robe off, they all cheer
>I turn around and wiggle my butt at them, they laugh
>Natalie tells me I have amazing legs, I blush a little, love it when she compliments me, she’s so beautiful and I’m kind of in awe of her
>I put the dress on, Natalie gets the wig cap and wig out of her closet, I put them on
>Lauren gets a curling iron out, says she wants to do my hair
>Laura brings me another drink, starts painting my nails with silver glittery nail polish
>Lauren runs the curling iron through the wig, smoothes it out with her hair then brushes it, takes about 30 minutes
>All done, oh my God I look so good
>I put the heels on, Lauren asks me if I’ve been practicing, I say I have
>Natalie tells us to have another drink if we want one, we need to leave soon
>Go out to the living room, Lauren puts some Gwen Stefani on the stereo, we dance around, they give me pointers on how to walk girly

>Natalie says we need to leave, Lauren pours some vodka into a water bottle
>Get in the car and drive off, on the way Natalie tells us we need to stick together, tells the girls to be sure they don’t lose me since I won’t have my phone
>We take turns taking sips out of the water bottle
>Get to the venue, it’s a big outdoor amphitheater
>Exit the car, can hear the opening act performing, it’s some rapper
>Wait in line to get in, it’s mostly teenage girls and young women there
>I try not to talk too loudly, hope no one can tell I’m a boy
>The girls say to stop worrying, no one can tell
>We get in, we hold hands and weave our way through the crowd
>Find our seats, we’re next to a group of four drunk college girls
>Girl nexts to Laura starts talking to us, she’s WASTED, tells us how cute we all look, says she misses being a teenager
>Laura asks her if she notices anything about me
>She says no, what is it
>Laura tells her I’m a boy, the girl screams, tells her friends
>They all say they had no idea, I look so pretty
>Lauren says see, we told you no can tell
>Feels really good to hear, I stop being nervous about it
>We ask the girls if they’ll buy us some vodka tonics if we give them money
>They say sure, two of them leave to get them
>These girls are so nice and cool
>They ask me if I’ve done this before and if my friends had to talk me into it
>I tell them I dress up a lot when I’m alone with the girls, this is my first time going out in public, and it was my idea to come to the concert in drag
>The two girls come back with our drinks, we talk to them some more
>Soon the lights dim and Gwen comes out on stage
>We all cheer, Gwen starts singing, we start dancing
>I’m having so much fun
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Oops, forgot to attach the picture of the dress

>After a few songs we all need to pee, hold hands again so we don’t lose each other
>Walk towards the women’s restroom, I ask if I should go in there, the girls say don’t worry about it, just don’t say anything when you’re inside
>I go in and pee in the stall, it’s no big deal
>We go back to our seats, the college girls bought us more drinks
>We all get trashed, dance our asses off
>The show ends about an hour later
>We hold hands again and make our way through the crowd, I’m wobbling around a lot, it’s hard to walk in heels when you’re wasted
>Lauren calls Natalie and tells her we’re on our way out, she’s already there and says she’ll pick us up out front
>Natalie pulls up, she tells me to sit in the front seat with her, wants to hear all about it
>I gush and tell her about how much fun it was, everyone thought I was a real girl
>Get back to the house, Natalie makes us smoothies, says we need to get something in our stomachs since we’re so drunk
>We go out on the porch and smoke some weed, Natalie smokes with us
>We’re all extremely fucked up at this point, I’m going to pass out soon
>The girls go to Lauren’s room to change
>Natalie takes me to her room, helps me take off the makeup and gives me the same pajamas I wore before
>Lauren walks in asks me if I want to lay in her bed and watch a movie with her and Laura, I say sure
>We climb into her huge bed, climb under the covers and watch Jawbreakers
>I fall asleep about 20 minutes later

[to be continued]
Been following this since it started. Keep up the good story, anon. Got much more to tell?

I have soooo much more to tell. I'm basically just chronicling my life from 13-25 (well, I was a month away from being 14 in the first story). Drag has been a big part of my life. I never planned on writing all this out, but after telling the first story I started feeling super nostalgic.
The whole thing is obviously fiction.
I love the fact that you keep insisting it's not!
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I've posted this before but I'll share it again.

>It’s summer break from school.
>The first time I crossdressed was when one of my older cousins won a bet when I was 5 or 6 and the loser had to do what the other person says.
>Our parents were usually busy at work they would have us hang out at my aunt’s house so we weren’t alone and kept each other company.
>I think the bet was to see who would win on some fighting game.
>I lost.
>The older of my other two cousins won.
>He said I have to go into his sister’s room and dress up like a girl so they could laugh at me.
>I can’t remember where his sister was that day but she wasn’t home either.
>Force me to look in her closet and eventually pick yellow sundress, pink panties and white pantyhose and some heels.
>I had long hair down to my shoulders when I was little and they laughed at me and said how much I look like a real girl.
>They stop calling me by my real name now call me Tina.
>Badly apply makeup and lipstick but even though my cousins are making fun of me I get a weird feeling in my stomach as I’m being forced to parade around as a girl for their amusement.
>Actually like dressing as a girl.
>Find out years later that I’m gay.
>Cousin says I can wash make up off because we’re worried it’ll stain my face and we’ll get in trouble with our parents.
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>After playing some video games we still have at least half a day until our parents get home.
>One of my cousins mentions we should go to the high school nearby and go swimming.
>The high school lets the public come in and use their pool to swim in during the summer.
>My cousin only has 2 swim suits and both of my older cousins want to swim.
>Complain that I can’t go because I don’t have a swimsuit.
>Older cousin begins to laugh.
>”Yeah you do. Hold on a sec while I go get it.”
>Leaves room and comes back with a girly purple one piece swim suit which has a frilly skirt similar to pic related.
>Get scared because I’m afraid I’ll get caught and don’t want to go.
>Cousin reminds me about the bet and says I have to go and nobody will know since I look like a girl anyway.
>Put swim suit on under yellow sundress and they give me his sister’s Barbie beach towel.
>Walk a few blocks toward school wearing nothing but yellow sundress, purple swim suit and some black flats because the heels were too hard to walk in.
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>Once we get there the person working the desk reminds me that girls need to go through the women’s changing room and I can see my friends at the pool.
>Cousin laughs. “Yeah Tina. No girls allowed.”
>Have to go through woman’s changing room.
>See women changing naked into their swim suits but I’m too young to enjoy it and too terrified of getting caught to make eye contact.
>Feel the same weird feeling in my belly and start hyperventilating due to the risk of getting caught.
>One woman sees I’m in distress and asks me where my mommy is.
>I tell her she’s at work but I came with my older cousins but they’re in the next room.
>She says “it’s alright sweetie. Don’t be scared. It’s just us girls in here and your cousins are waiting for you on the other side of the door.”
>Take off sundress and flats and fold them on the Barbie towel.
>Luckily the swim suit’s skirt covered my crotch I don’t know what would have happened if I was caught but she didn’t notice or at least didn’t let me know she noticed.
>The moment I exit the room I run towards my cousins immediately because I’m afraid of being found out.
>She thinks it’s adorable and goes on with her own business.
>Swim with cousins but barely say a word.
>Terrified of the other kids finding out or one of my cousins being a dick and outing me in public.
>All the other kids we play with don’t notice and just think I’m shy.
>Manage to get home without anyone finding out and my cousin says I better change back before our parents get home.
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>The rush of crossdressing and not getting caught made me love it and I would secretly crossdress in my mom’s and my cousin’s sister’s clothes because we were close to the same size.
>Even though I was scared my first time out en femme I would lose bets on purpose with my cousin secretly hoping he would make me do it again but he never did. Eventually while playing video games remind him about the time he forced me do crossdress and he remembered
>“Yeah that was really bad”. He said it was just too mean and he felt bad about what he made me do so he didn’t feel right forcing me to do that again after the first time.
>Secretly disappointed.
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>Continue to crossdress in secret for years until mom catches me in her clothes at home and she got really angry.
>I was caught because I finally wanted to try painting my nails and when clean up time came around I didn’t know how to scrub them clean.
>I was focused on getting rid of the paint on my nails I didn’t bother first removing the pink silk nightie, black pantyhose and lacy black panties.
>So Mom caught me scrubbing my hands in the kitchen sink fully dressed as a girl still wearing my red lipstick and eye shadow.
>Mom gets furious and calls me a faggot.
>Pulls kitchen knife out of a drawer and points her finger at me and shouts.
>”Are you some kind of faggot!?”
>”You wanna be a girl!?”
>”If you really want to be a girl I’ll chop that pecker off right now!”
>I’m absolutely terrified and say no.
>Mom makes me clean up and change.
>Then she throws away any of her clothes are remotely my size that she no longer can wear.
>She throws dildo away in disgust but I didn’t learn what that was until years later.

I wish it was as acceptable to be raised trans as it is now. I wish I could have transitioned as a teenager but now if I bother to try I’ll just look like an ugly hun. Chances are I probably wouldn’t have been able to anyway with how angry my mom reacted.

Thanks for triggering the entire board, asshole. My eyes are getting wet, what is this shit?
Even though this anon's stories are triggering and make me cry, I think it's beautiful. Sure I'm sad that I didn't have these rich experiences or such good friends in my youth and I'm just now trying to embrace myself in my early 20's rather than repress, but I get a sense of hope like maybe things aren't so bad and maybe I'm not a bad person for wanting a life like that.
>inb4 it's all fake
Honestly I don't even care if it is at this point.
Just fuck off already.
This kind of thinking put off hrt for 10 yrs. Sure, neither of us get to be girls, but at least we can live as women in time.

> plz2notmentionkidstho
>Used stepmom’s nail polish and tampons (ugh) in high school.
Can we get some real stories? These long ass stories that guy is posting are so obviously fake it's ruined this thread. The last thread was so much better, but I already told my best stories there.
These are incredible, please keep posting them

I've cried a bit while writing these stories. It really makes me feel good to think that they may have a positive effect on some of you guys reading them. And like I told someone yesterday, it really isn't too late for you if you're in your early 20s. I had female roommates from 21-24 and dressed up all the time. I owned more girl clothes than guy clothes during that period. I'll get to those stories eventually, but they're a long way off.
It's never too late to try friend, I transitioned when I was 22 and I came out super passable and cute. You have no idea how amazing it feels to finally be yourself after hiding your feelings for so long. Trust me when I say that you need to trust your feelings and start living as your authentic self. It'll be hard and shitty but at the end of all of it is the most amazing happy feelings that just make you smile all the time. Life is too short to not be yourself <3
>it really isn't too late for you
I'm 23, and it's just that I've repressed my interest in this sort of thing for so long that now I'm trying to figure life out and pick up the pieces long after you did. Other than my shitty part time job I'm basically a neet living at home, and I just don't have the privacy to do anything without being discovered. My entire life has been trying to make sure my family wasn't disappointed in me, but disappointing them seems unavoidable at this point.
Thank you for this. I had really been fighting my feelings over the past year or two, but I think I'm finally starting to accept myself. The first step is asking my trans friend for support, but I've never confided in anyone about anything before. I just can't help but think about what if I'm wrong and these aren't genuine thoughts or feelings.
You're anonymous, if you want to you can talk to me about this stuff. I know what it's like to know what to do but have no idea how to do it. I went into it alone and I know it's a really shitty situation and wouldn't wish it on anyone. I can probably give you some advice of you need it
I didn't start indulging in my crossdressing until my twenties. I still lived at home and had to keep it secret from my family.

I would rent a hotel room on a night I planned to dress up and go there to change. At the time it was difficult to find places to go. Now I just go to gay clubs and hang out.

In my favor was the fact that I lived in a city and while my family didn't know, they still respected my privacy. They would see me going in and out with a bag on certain nights but didn't bother me too much as long as they knew I was acting cautious and responsible.
Please write more

There's a lot more coming, but I just got home and need to get some sleep. I'll post more stories tomorrow if I have time.
Please do, these are all so beautiful
Oh wow, your mom is an absolutely horrible person. You should get away from her ASAP.

You should still give transitioning a try. Everyone cries about being a "hon" now if they don't get started by like 18, but even just 5-10 years ago, there wasn't much trans acceptance and people transitioned a lot later in life. Not all of them became hons and technology wasn't as good as it is now.
I'm sorry I had to leave anon. I'm very quiet and shy outside of 4chan when it comes to anything personal, but I would've loved talking with you more. This is the time I would usually dump a personal blog about my feelings and shit, but I don't think this is quite the thread for that sort of thing.
Thank you for sharing your story with me. I've entertained the idea of doing that exact thing before, but I live in the suburbs and my family would play 20 questions with me looking for the who, what, when, where, and why if I started going out for a mile walk down to the bus stop to go into the city every now and then. Even if I did get out, pickup my clothes from an amazon locker, and get changed at a hotel room I don't even know where I would go next.
Keep them coming. Fuck cares if it's real or not, it's a good read.
Anon, we REALLY need to see pics of you dressed up now. No excuses. Post that frilly ass.
Please keep writing more
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OK since you asked nicely here are some pictures of me from a rave last year, dressed like a fairy and wearing a cheap wig LOL. I cropped out my face but at least you can enjoy enjoy seeing my body
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Here's me from the side
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And here's a closeup of my sweet tits
>cold night and had no clean/dry pajama
>my gf suggests me to wear her yoga pants
>it felt very nice
>i couldn't stop waking up in the middle of the night to see me wearing those pants in the mirror
>>I have a nice ass
>since that day, I cross-dress whenever I can

>I feel sexually aroused by my feminine side
>and wearing feminine clothes
>>that's a problem, it's hard to wear panties when having an erection...

Yeah, living in a city is really good for crossdressers. I lucked out on that.

We have a part of town with a large gay population, so it's not weird to see the occasional drag performer walking outside.

I purposely get out of the cab a small distance from wherever I'm going so I could walk down the street dressed. I love to just be in a leggy leotard feeling the night air all over me. It's one of my favorite parts of the experience.
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Oh boy is this the climax of the story?

Also really happy you showed off. I'm (we are) craving for more tales

Thanks sweetie

I have a ton more stories. Hopefully I'll be able to post some tonight.
Good gracious. I came to this thread with no expectations and read some wild consentual crossdressing stories. Its been awesome. Kudos especially to
>>9257301(hot, thoroughly enjoyed the sex couple, unf. Interested in more stories? When u changed schools was it weird saying bye?)
>>9241111 (nice figure, cute stories, so wholesome, very fun)
After a few quick googles it's starting to look like the closest clubs to me might be better attended by taking a day to travel and staying in the city overnight so I don't feel rushed trying to get back home that night.

I'm concerned about cameras though. I'm sure you can tell by now that I'm in the closet and nobody irl knows the way I feel, and I'm concerned about running into someone I know while all dressed up or being outed by being in the background of a picture on social media.

OK, just got back from seeing Lady Bird (it's really good, you should see it), need to crash soon so this will probably be kind of short.

-We sleep in pretty late, Laura wakes me up and says we need to get going because she has to be at the hair salon in a few hours
>Wake up Lauren, tell her we’re leaving
>Look for Natalie to say bye and thank her for the concert tickets but she’s not home
>Laura drops me off at my house
>Few days later, go over to Laura’s house for Jennifer’s graduation party
>Jennifer tells me she’s heard about all the dressing up I’ve done lately, says she feels responsible because it was initially her idea to dress me up on Halloween
>I laugh, thank her for introducing me to my new hobby
>She says she’s going to miss me while she’s at college, hopes I find a cute boyfriend soon
>Tell her that’s very unlikely to happen anytime soon
>She gives me a hug and tells me to hang in there, things will get better when I’m older
>Next day, walk over to my school friend’s house to buy weed from his older brother
>Friend asks me about these girls I hang out with all the time, wants to know if I’m hooking up with either of them
>I say no, we’re just friends
>He asks me if they’re hot, I say yeah they’re pretty cute
>Asks if he can meet them, I say I don’t think you’d like them that much, change the subject
>Following week, Lauren gets her license and a car

>Start a daily routine where she picks me up and we go running at a park near my house, sometimes Laura joins us if she’s not working even though she hates running
>Always drive around around afterward and smoke a bowl, getting high after working out feels amazing
>One day we decide to see a movie instead of running
>Get there early, go into the parking garage and hotbox her car
>Some guy from her school keeps texting her, she says she’s not into him and he won’t get the hint
>I say at least there are guys who are into you, I mean you’ve already had sex and I haven’t even made out with anyone before
>She says she’ll make out with me if I want, I laugh, she says she’s serious
>I say OK why not
>We make out for a few minutes, it’s pretty fun
>Go watch the movie, afterwards we go to the Gap because I want to get some new jeans
>While I’m looking at jeans Lauren walks up holding two sundresses, says we should get them, we can wear them while sitting by her pool next time I’m at her house
>I laugh and say OK
>I pick out some jeans, she drives me home
>Few days later, Laura has the day off so we go over to Lauren’s house in the early afternoon
>Natalie lets us in, gives us hugs, says she heard that Lauren and I made out in her car, asks how I liked it
>I laugh and say it was great
>She says she washed my underwear and wig for me, they’re in Lauren’s room if I need them

>Lauren comes out, says let’s go hang out by the pool, come to my room and put on your new dress
>Go to her room, change into my panties, put on the dress, don’t bother with a bra
>Dress is long and flowing and has a slit, floral print, it’s really comfortable
>Looks like pic attached, but not as fancy
>Lauren puts her dress on, puts some light makeup on me
>Ask if I should bother with the wig since we’re not going anywhere, she says put it on, it will make her mom happy
>She gives me a pair of oversized sunglasses to wear, grabs a stack of magazines
>We go to the kitchen where Natalie and Laura are hanging out, Natalie asks if we were making out again, we all laugh
>Natalie asks if we’re spending the night, I say sure, Laura can’t because she has to be at the hair salon at 10 tomorrow
>Natalie asks Lauren and I if we want margaritas, we say yeah, she says she’ll make them then come out and join us
>We hang out by the pool for a few hours and talk, read magazines, smoke some weed
>Go inside when it starts getting dark, Natalie orders sushi for us, we drink wine and watch TV
>Laura leaves around 11, Natalie says she’s going to bed, asks me if I want to borrow a nightgown instead of pajamas this time
>I say I’ll try the nightgown
>Go to her room, she gets a nightgown out of her closet, looks like pic attached
>Put it on, it’s comfy as fuck, she says goodnight
>Go back to the living room, Lauren asks if I want to watch Bring It On, I say sure, never seen it before
>It’s actually really funny
>Movie ends, we’re ready to go to bed
>Go to Lauren’s room, we take off our makeup and wash our faces
>I go to the guest bedroom and fall asleep
>Wake up the next morning, Natalie makes us smoothies (she loves making smoothies)
>Lauren drives me home, asks if I want to go for a run later, I say sure
>Go running later that day, we drive around and smoke a bowl
>She drives me home, I watch movies the rest of the night

[to be continued]

Forgot to attach picture of the dress
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Here's the nightgown pic
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>>She says she’ll make out with me if I want, I laugh, she says she’s serious
>>I say OK why not
>>We make out for a few minutes, it’s pretty fun
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This is one of my biggest fantasies...

Thank you very much for the green-text! <3
glad you like it! It was easily one of the most fun times of my life, I'll continue it
>after breakfast I clean the dishes and watch TV
>she comes out and we just chat about random stuff, she asks some personal questions
>why I like to cd, etc.
>say I just really like feeling like a girl
>asks how I liked the sex
>said it was amazing, causing her to laugh
>run out of things to talk about so just watching boring as shit sunday tv
>suddenly she says she's bored
>turn to ask her what she wants to do
>she leans in and kisses me deep, pushing her tongue into my mouth
>pushes me down on the couch and just goes at it, she's really rough and pulling my head into the kiss
>we make out for again what seems like ages before she stops and acts like nothing happens
>day goes by with nothing else happening
>microwaving some dinner that night
>she walks by
>turns to me and pushes me against the wall
>starts making out with me again, trying to surprise me
>works and then she walks to the fridge like nothing happened
>realize she might be trying to condition me
>kind of like it
>he comes home finally
>heart races as soon as he enters the room
>they chat, she kisses him, he doesn't kiss me but asks me about my day
>I tell him nothing much but notice him carrying a pink bag
>ask what he got her
>he says it's for me
>he pulls it out
>it's a buttplug
>says I have to wear it all the time so I can be ready if they need me
>or more specifically, "If they want to use my body,"
>blush hard and thank him
>he goes to shower and asks her to get it in me
>she puts it on the counter and goes to get some lube
>thing looks pretty big but mostly long
>she comes out and tells me to bend over
>lube up my crack before sliding her fingers inside
>makes a comment about how I'm already lose from him
>she lines it up and starts to push
>feels massive
>eventually works it in all the way
>feel really weird when I walk around with it
>normal for the rest of the day, go to bed
>few days pass and nothing else happens
>she went home to visit family for a few days
>get woken up that night, think it was like thursday
>it's him
>super sleepy and confused but he just pets my hair before picking me up and taking me to their room
>heart is racing because I know exactly what this probably is
>he tosses me on the bed before stripping
>starts to take off mine
>reaches between my legs and pulls out the plug
>I cover my mouth and let out a whimper cause it kind of hurt
>he starts lubing up his fingers before pushing them inside me
>says he wants to do it missionary style like a couple
>my heart jumps
>he spreads my legs around his back and lines up his cock
>pushes it inside me
>still kind of tight despite the toy
>but he's soon all the way in
>he starts to fuck me hard
>cums really fucking quickly inside me, swear I can feel a warm sensation
>he then grabs the buttplug and pushes it in
>gives me a kiss before telling me good night and rolling me onto my side and spooning me
>don't realize until later that I didn't cum
>wake up with his arms around me
>really have to pee
>walk to the bathroom and pull out the plug
>again a ton of cum falls out
>ass feels kind of sore
>hear him get up and come to the bathroom
>tells me I can leave it out tonight
>I thank him and get up, he pulls me in close and gives me a slow, passionate kiss
>I go back to bed and wait for him
>I go to the spoon position but he pulls me on top to lay on him
>falls asleep to his heartbeat (also he was way too fucking hot)
>have a weird dream I can't remember
>wake up and feel him fucking me
>I'm still on him and he's plowing me
>have an earth shattering orgasm and we both fall back asleep in all the mess
>wake up next morning and wonder if I imagined that
>he kisses me good morning and grabs my hand
>holds it while leading me to the shower
>I'm expecting sex again but he just washes me
>washes my hair, scrubs my body
>is really caring
>gives me another kiss and tells me he is going to make breakfest
>we talk and chat and flit a bit
>feels like I'm an actual girl dating a guy
>on cloud 9
>she comes home that day, I go back to sleeping in my bed
Fuckin' hot.
i don't care if this story is fake just please more
>yfw girls can't crossdress because there are literally no social consequences for an afab to wear full male outfit
b-but fake stories aren't true!
But we can dream anon we can dream
Fuck off
sure thing<3
>wake up the next morning
>feel really sore, legs are kind of wobbly
>go out to the kitchen
>she's up, says good morning
>gives me a hug and thanks me for taking care of him while she was gone
>tell her I feel like I should be thanking her
>she giggles
>he's sleeping in so don't see him
>go to class, come home, no work
>drop my book bag and go to the fridge to grab a drink
>hear him say hi
>ask where she is
>he says at work
>comes over and starts kissing me
>simply ask, "Again?"
>he says yes, the guy is like a greek god of stamina
>starts playing with my ass but I'm still sore
>tell him
>can tell he's a little disappointed
>grabs my hand anyway and leads me to their room, don't really argue
>makes me lay down on the bed, feel kind of like his personal sex object
>starting to get a fetish for that so wouldn't mind but still sore
>ask him to go slowly at least, plus I didn't wear the plug to school
>he says not to worry, we're not having sex
>confused cause he took me to the bed
>he tells me to get on my back and lay down
>grabs my shoulders and pulls me to the edge of the bed so my head is hanging off
>realize what he wants
>for some reason this makes me blush like crazy, never had a dick in my mouth
>he undresses and soon is standing with his cock towards my mouth
>hands are being really gently and opens my lips
>no foreplay, his cock just goes in
>not as bad as I thought it would be, also not particularly sexy
>suck on it, lick the bottom, all normal
>he starts to thrust in an out
>be still naive and not realize what's coming
>feel the cock press against the back of my throat
>gag a little and go to move my head and apologize
>he just grabs my jaw and does it again, this time pushes hard
>realize he wants to fuck my throat
>cock starts pushing into my mouth
>surprised hear him just shhing me and telling me I'm doing great
>feels absolutely massive, swear it's going into my stomach
>start tapping his leg to let him know I need air
>he pulls out quickly and I gasp
>only get a few breaths before he pushes back in
>I'm gagging pretty hard but he's still going
>soon he's in to the hilt and my lips are against him
>just holds it there and twitches, I can feel it strain against my throat
>he grabs my hands and brings it to my throat
>I can feel the bulge
>he starts to fuck me and I can feel his cock under my skin
>close my ears and hope he comes soon
>vision starts to go a little fuzzy as he goes faster
>start tapping his leg but he's close so ignoring me
>actually get a little scared
>he bottoms out and orgasms hard
>pushes really hard into me
>feel him pulsing all throughout my throat
>few seconds later he finally pulls out and I'm coughing like crazy
>feel really nausea and try to get off the bed
>fall to the floor and he's there asking if I'm okay
>cover my mouth and point to the bathroom
>he carries me there quickly and I puke into the toilet
>I can see all the cum he shot into my stomach in there
>he holds my head and rubs my back
>says sorry, doesn't know what came over him
>I say it's fine
>catching my breath and he's just sitting there rubbing me
>asks what he can do to make it up to me
>think for a bit and ask if he can wash me again
>we both laugh and get in the shower
>he spends a long time cleaning me, being sweet
>I tell him that it felt kind of hot to be used like that
>suddenly he says he gets an idea and tell me to wait there
>gets out of the shower and slips a bit, I laugh
>he comes back with a toy clearly for my ass
>tells me I didn't get to cum
>remind him that I'm still sore
>he says trust me
>he blocks the drain and starts making it a bath with even bubbles
>then lays down and pulls me down to
>I'm on my back in his arms and he's just kissing my neck
>hands are rubbing my thighs
>grabs the lube (cause of course they have a second bottle in the shower)
>really gently starts to push his fingers in and lube my ass
>asks me to spread my legs
>I trust him and do so
>he very slowly and gently pushes it into me
>not really far at all
>if I knew anything about sex toys I would have realized what he was planning
>suddenly feel vibrations inside
>moan loudly, it's a prostate massager
>he holds me and keeps kissing my neck and running his hands up and down my tummy, like with the finger nails gently, and playing with my nipples
>moans turn to whimpers
>time seems to stop as I'm just sitting there with my eyes rolling back and twitching
>tells me to let him know when I'm going to cum
>can only nod my head
>barely let out a small "now" when it happens
>he bites my ear
>massive orgasm
>water everywhere cause I couldn't help but flail a bit
>we lay there for a few minutes as I cool down
>he then kisses me once before slowly pulling it out and helping me up
>gets out of the shower and grabs a towel to dry himself off
>starts to dry me off too
>then picks me up and carries me out of the bathroom
>i'm insanely tired and really happy I don't have class tomorrow
>he lays me in their bed and tucks me in
>tells me to sleep well and he'll wake me up for dinner later
>kisses me once before closing the door
>I fall asleep naked in their bed
What do you think the "ugh" was for?
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Here’s a real quick one before I head out the door, I’ll post more tonight if I have time.

>Couple weeks pass, we go running most days, the girls go to a few parties but I don’t join them
>Lauren leaves to go visit her dad in Florida for 12 days, says she’s dreading it because her dad is a sleazy prick, hasn’t forgiven him for cheating on her mom
>What kind of person would cheat on Natalie, the woman is an angel
>Also her older sister is flying to Florida too and she’s kind of a bitch
>Laura’s parents go out of town for a few days, I go over there one afternoon to hang out with her and Jennifer
>Go out on their patio to smoke some weed, Jennifer has weed too so we smoke a ton and get incredibly high
>Jennifer is hilarious when she’s stoned, says completely ridiculous shit
>Go sit in the living room and watch TV, Jennifer asks if she can put makeup on me, says it might be be the last time she ever has the chance since she leaves for college soon
>She goes to her room and brings back a bunch of makeup, we watch TV while she puts it on me
>She tells me a funny story about her prom, about how some guy threw up all over the dancefloor and caused a huge scene, got thrown out
>She asks if I’ve seen her prom dress, I say no
>Go to her room and she shows it to me, I tell her it’s really pretty
>Looks kind of like attached pic
>She asks me if I want to try it on, I say sure
>I put the dress on, she says she’ll be right back
>Comes back with the same pink wig I wore on Halloween almost two years ago, I put it on
>She pulls out a stack of pictures from that day and we look at them, she says I’m slowly changing from a girl into a young woman, we laugh

[to be continued]
Well if you just want to ask me things I here I would be more than happy to help you
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Omahgod YES!
I don't want to start crying in the thread about my life or anything, but I do have some questions if you don't mind.

Any tips on clearing or covering up blemishes (some relatively minor scars) on arms/legs?

What are some excuses I could use when I shave my face rather than trimming my beard down like I usually do? I've had it for years and I feel as if I need a rational excuse or else someone will think something is up.

When I do get an outfit I like and become confident enough to show my face in public, what are some things I should try doing or places I should try visiting if they're in my area?
>at best friend's apartment
>just got dumped by his gf
>just having a few beers together as normal
>he finds some lingerie he bought for her and is about to throw it out
>ask him if I can have it
>he acts a little bewildered, but says sure
>go into the bathroom and put on cami corset thing and thigh high stockings
>fits perfectly
>come out of bathroom, sit down on couch, continue drinking and talking for a couple more hours
>he's surprisingly cool with this
>put my clothes back on over it and go home
>show it off to my roommates when I get back
>they seem slightly weirded out, but amused
>continue wearing her clothes in private til they wear out
Not who you asked but thought I'd chime in. Can't offer advice on the blemishes/scars.

I shaved my beard off. Just told people I wanted a change. No one questioned it.

When I first ventured outside dressed I did it at night. It gave me a little more confidence. I also went to places not around where I lived. Then I started going out during the day and around my neighborhood. I have that skater girl look that is closer to being androgynous than feminine but it helps me gain more confidence gradually.
Just use concealer/foundation to cover up all that stuff.
Just say that you got tired of trimming it or that you just wanted a new look. Guys shave their beards all the time, it's no big deal
I used to take walks around my neighborhood in a dress when I was pre her, it was nice to just be able to walk around and not really have to worry about being seen. If you look like a guy than there aren't really any places you can feel really confident in, but with decent enough makeup you might be able to make it work.
Thanks for the answers anons. I feel awful for asking questions in this thread because it's supposed to be for stories and not a support group.

What about arm hair? I can't imagine enough guys just casually shave their arms that nobody would question it.

[spoiler]Will I ever stop feeling ashamed for wanting to dress up as a woman?[/spoiler]
>snuck into my little sister and mums rooms while home alone and stole a bunch of shit (i only stole clean stuff) my sister had some frilly thongs and some fishnet stockings i stole, my mum has lots and lots and lots of clothes, so many and so unorganized that i could easliy take stuff and she would never notice it gone, sadly her taste is horrible and all she had that i liked was a pair oh high heals.
my sisters clothes actually fit me pretty well even though shes 17 and im 20.

i shaved and put on a dress, thong, stockings and shoes and was walking around the house just chillin and enjoying feeling cute, ive always heard girls complain about high heals being hard but i guess im a natural (they were 6 inchishidk platforms aswell)
and then nothing happened, i havnt been caught yet.
i have a favorite thong made of frilly transparent lace that i like to wear to college sometimes and pray i dont whale tail while bending down to pick up my bag.

i dont really have any exiting stories yet im still fairly new to this but im sure one day my family is going to come home sooner than i expected why im learning how my sisters makup works.
never stop
keep going with this i dont care if its real or not im loving it

im getting super sad tho im almost 21 and i only became gay when i was 19 and ive only started unrepressing my transness since i was 19 as well, ive never had any girls to hang out with ive only ever hung out with boys and have no idea what so ever how to talk to girls even as friends, ive been wishing to find some girls to help me with gay shit and i can be their gay friend and talk about boys and stuff.
you said most girls would be ok with this stuff but i can hardly just go up to some random girls and say "hey want a dress up doll?"

how do i get cool girlfreinds?
and how do i talk to girls? ive only talked to a gril as a freind once and she was basically a lezbionic who acted like a boy.

>pray i dont whale tail
What the ever-living fuck is this?
Not that anon, but it's when your thong is visible above your pants.
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Just shave. I get lazy for a few months, don't shave and put on a few extra pounds. Usually during the winter. Come springtime I shave, get my brows done, and eat normal human food again. If anyone questions me I just tell them to blow me. Or "Fuck you, I wanted to." Then again, most friends know I'm a crossdressing faggot so it's usually a non-issue. They're more concerned when I'm not pretty than when I am.
I honestly doubt people would notice you shaving your arm hair. I walked around with shaved legs as a guy and no one said anything.

And yes you will if you get on her soon enough and start becoming a qt grill
yeah i was paranoid too when i first started shaving but een wearing t shirts and shit nobody has ever noticed as far as i know, my mum and sister have even seen me walking from the shower to my room with just a towel round my waist and dont seem to have noticed my shaved legs.

nobody really cares, and if anyone does mention it just say cos it feels nice or somthing
I'm glad everything is working well for you. On the topic of friends, how should I approach this topic if I decide to come out to them? I'm really close with someone who is trans, and while she would be the first person I would tell about any of this, I'm really concerned that she might think I'm mocking her or something.
I think I'm going to take things slow and just shave my legs at first. I just don't see how nobody would notice that my arms were no longer hairy when I wear t shirts all the time.
>And yes you will if you get on her soon enough and start becoming a qt grill
I don't know if that's something I really want. Like I think I want to go all the way, but I'm hesitant to accept it. I'm not sure if I could pass, and I don't want to turn my life upside down just to become a hon. Also I'm still undecided on how I feel about the sterility issue.
I think my problem is that I feel the need to justify anything I do, especially things that deviate from my norms, with an explanation that's more than "because I felt like it".
You can always bank sperm. And trust me these feelings are never going to go away, you have to try at some point if you ever want any chance of actual happiness. The longer you put it off the less your chances are. Hons get a lot of crap but at least they live their lives the way the want too. Plus you might even turn out to be a qt, and trust me that's the best feeling in the world. If after 2 years you don't pass than you can always start looking at surgery. Don't listen to the doubt in your mind, you know what you need to do to have a good life
I almost lashed out like an abused dog and posted a hostile wall of text, and I'm sorry for that. You're just trying to help and you don't deserve that.

I do envy hons for their ability to live how they want, but I'm simply not brave enough to do the same. A "chance" at happiness just doesn't seem worth potentially losing family relationships and more. I used to be numb to everything, but I got stressed and careless in college and now I can't stop feeling things. I'm even scared of feeling something like happiness and seal it away, because it just opens the door to more sadness. I don't want to listen to the doubt in my mind, but I have to because that's all there is.

I'm sorry, but I just can't do it. I'm so afraid of becoming a hon and the uncertainty about my quality of life that I feel like I'm stuck between a rock and a hard place. I feel as if I have to try to grit my teeth and try to be a man. I'm probably already a sad excuse of a man in the eyes of my family, but at least I can try to find a wife and have a kid or two. I couldn't be dominant if I tried and I push everyone away, so I'd probably just end up living a "life" full of missed opportunities before dying alone.

My head feels like a garbled mess of thoughts and emotions right now and I'm definitely going to be crying at some point later. You've done nothing wrong, I know this is all self inflicted (which makes it worse because I can't blame anyone but myself).
You'll only be a "hon" if you keep waiting. I swear, some of you damn kids think not transitioning by the time you're 20 automatically = hon. Finding a wife and having kids when you're like this is even worse, because you're just inevitably setting them up for turmoil later in life when you finally have a breakdown from repressing too much.
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This is a 65 year old man who transitioned, ignore the transition before your 20s meme. I was 32 when I transitioned and I turned out pretty cute. I know what it feels like to be numb to everything, that's what I was like before I transitioned. But as soon as I started I slowly regained my personality and became a much better person for it. Trust me, it'll be long hard and shitty and they'll be times where you'll feel like you're wasting your effort, but it will all pay off in the end
I dunno. We were just hanging out one day in high school and a hot girl walked by. A couple guys said how hot she was and I said something like "That's a real cute top. I want it." I mean, I'll bring it up if the conversation goes that way. If you feel you need to "come out" then I'd suggest talking to someone in private. Just be like "Hey bro, I like dressing like a girl. It's why I'm always shaved and stuff. Anyways, we playing Halo 2 or what?" I mean, you do you. I was just born without fucks to give. You've just gotta live your life unrepentantly.
She looks pretty good for that age.
Just found out there's a store in my small town in bufu nowhere that caters primarily to plus sized women and all sized crossdressers and trans women. Neat. Guess I'm blowing a paycheck there this weekend.
>You'll only be a "hon" if you keep waiting
I'm sorry, but I feel like I have to try and weather the storm because this might just be some kind of depressed phase. I hate myself so much over the fact I'm too scared to make a decision so I opt to just do nothing. I just need to figure out if transition would be a mistake that I would regret, but I don't think I will ever be convinced.
>it'll be long hard and shitty and they'll be times where you'll feel like you're wasting your effort, but it will all pay off in the end
I want to believe you anon, I really do. I don't think I would be strong enough for such an endeavor though. I'd probably just fuck it up like I do everything else.
Thank you anon. It always seems so easy when it's written down. I don't necessarily want to come out, but I feel as if I need to confide in somebody about how I feel for support and maybe even validation that it is okay to feel these things. I just really do not want to disappoint anybody so I bottle everything up.
>I was just born without fucks to give. You've just gotta live your life unrepentantly.
I wish I could be like that. I give way too many fucks and I am way too caring about others while not nearly caring enough about myself.
Eh, just get drunk and yell it at someone. That's what I do if I need to get something off my chest. Or draw a shitty picture in ms paint explaining your feelings.
I don't drink, but I'm no artist so maybe I should just take up drinking.
Dude just talk to a therapist and try, these feelings will never go away and they'll just get worse with time. The longer you wait the worse you'll feel and the harder it'll be to transition
I know I need to talk to a therapist, but it just seems out of reach. I'm on my parents insurance and I don't need them to find out I started seeing a therapist through some bill from the insurance company. Now that I think about it, I don't even know if our insurance covers that sort of thing. I doubt my job pays enough to allow me to see a therapist out of pocket, and I just don't know what to do.
Maybe you could take blockers until you feel ready to get on HRT? Not trans, so maybe someone who knows more about this can give you better suggestions. And maybe you could start crossdressing and/or taking hormones, but not get bottom surgery, and if it still doesn't help or feels wrong to you, you can de-transition, but if it does feel right, you'll have taken steps to prevent any perceived "hon-ness". Again, these are the suggestions of a cis person, so you transpeople get in here and help me.
First off I want to apologize for derailing this crossdressing story thread. Thank you for offering suggestions anon.
>maybe you could start crossdressing
desu I first came into this thread to read stories and learn more about crossdressing. I have no intentions of removing my dick since it doesn't bother me too much and the results don't seem desirable to me, but I figured that maybe if I started crossdressing my problems might be at least somewhat soothed. If I saw myself all dressed up maybe I would realize this whole thing isn't for me and this desire would go away.
saw some leggings and a dress my mom bought for some event she was going to

>hey mom could i try that on?
>sure anon

that's it. happened when i was a freshman in high school.
Your mom sounds pretty cool. Any other stories?
yeah she's pretty chill and i do not sorry anon.
Thread is kill, need a new one.
That's the point. Just something real bad. add random text in to explain whay things are. Examples:
>kind of a girl
>my brain is full of fuck
>rainbow socks uwu~
>I don't always dress like a girl, but sometimes I do
>love me plis
I'll give it a shot, but I have a busy day ahead. The thread will probably be dead before I get around to it. Thanks.
>page 10
New thread when?
Waiting for that one anon who said he would do it.

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