>>45120085
Last week’s thread was amazing, hopefully these can become a weekly thing like they used to be

>>45120085
bump because these are amazing
>>45120265
literally

>>45120085
During last week’s thread I really wanted to share the story about the time I posed as a girl and me and my cousin catfished some boys she knew, but I can’t figure out how to turn it into a greentext that isn’t so absurdly long no one will even read it

>>45120569
I'll read it.

>>45120085
>be hs freshman
>obviously gay but still in the closet
>very skinny on purpose, wear girls t-shirts, shave my body hair, etc
>go to big party
>meet girl who goes to an all-girls catholic school
>there’s like a dozen of those in my city so not unusual
>we hit it off, spend whole night talking
>talk every night that week
>go out with she and her friends the following weekend
>she’s extremely persistent and quickly becomes my gf
>we meet up 2-3 times a week, sometimes more
>she has a high libido and is frustrated that I won’t go any further than making out
>would tell me that all her friends think I’m gay
>yeah no shit
>one day she asks me to put on one of her dresses and I say ok
>put it on and she does my makeup
>looks really cute
>she’s REALLY into it and admits she’s been wanting to dress me up for a while but was afraid to ask
>this becomes our new routine
>go to her house, get dressed up, make out on her bed
>eventually her mom even knows about this but is strangely cool about the whole thing
>she’d text me every day about it
>once confessed that her biggest fantasy was to see me in a wedding dress lol
>everyone at my school thinks it’s weird as hell that I have a gf
>start to feel guilty about being a closeted gay and decide to tell her
>she says she knew the whole time but didn’t care
>the fact I was gay made me more attractive to her
>she still wants to be my gf but I tell her that’s just not going to work
>feel awful about it
>we stay good friends though
>I officially come out to everyone
>nbd since everyone already knew
>few months later she starts dating some jacked hockey player guy

>>45120761
Maybe I’ll post it later after getting home, I just don’t want to spend like an hour typing it up and then everyone scrolls past it

>>45120911
Awe sweet story

>>45121172
Thank you :), guess I should add that I did continue to let her dress me up after we broke up, but it was no longer a secret thing and soon basically everyone knew I was a crossdresser lol

>>45120265
I still think about one of these threads from 2019 where someone posted like a 10 part greentext explaining how they once managed to spend an entire summer dressed as a girl out of the house without their parents ever finding out

>>45121584
i think i remember something liek this

>>45121599
I remember it was posted over Christmas break by someone in college. Problem is people in their early 20s don’t have crazy stories like that from their teen years anymore which is probably the main reason why crossdressing threads basically disappeared from this board

>>45121365
Its really nice you are each others bestie

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>mom caught me wearing her bra and panties
>I refused to talk about it when pressed
>later found a bag in my room with new panties and a note saying she's not mad and I can talk about it If I want but even if I don't she bought me some so I wouldn't have to steal hers

>get first job
>have money to spend on random shit
>buy makeup and womens clothing to try on "as a joke"
>put in on one day
>look in mirror and instatly break down in tears because im really pretty and realize that im a tranny and not going to be able to stave off the feelings by occaisonally putting on womans clothing anymore
>walk into living room
>cats dont recognize me, run away and hiss

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>be dumb straggot teenager
>the thought of wearing women's clothes icks me out
>occasionally dress up in this bizarre genderfuck way with a suit and headband and bracelets and flowers in my hair
>fast forward a few years
>rogd
>tell parents, they send me to a psych
>think this is taking too long and get on diy
>become more and more miserable
>spend hours lying on the floor
>mom knocks on my door
>WHAT.mp3
>brought a weird tight-fitting shiny black shirt thing
>try it on
>looks horrible with my conetits
>stuff it in the back of the closet
>a few weeks pass
>mom comes back
>brought headbands/comb things that go in your hair
>stammer "I don't want those" and slam the door
>cry

>be a faggy little 7th grader
>let some girls dress me up as a prom queen for Halloween
>look gorgeous
>get lots of attention all night
>immediately want to dress up again
>couple weeks pass
>have the house to myself for an entire Saturday until late at night
>work up the nerve to walk to this hipstery vintage women’s clothing store a few blocks away
>flip through racks of dresses
>have no idea what I’m doing
>owner of the store asks if I need help
>very pretty woman in her 30s
>say I want to buy a dress for my sister as a gift
>she clearly knows I’m lying
>asks what size I need
>say I don’t know
>she asks if my sister is about the same size as me
>say yes
>she starts pulling out dresses and holding them up to me
>she asks which ones I like and I pick out a few
>she asks if I want to try them on
>get super embarrassed but she talks me into it
>go in dressing room and try on first dress
>she asks me to come out and helps zips me up
>she’s being so nice that I’ve stopped pretending the dress isn’t for me
>try on a few other dresses and she helps me decide which one is best
>don’t have enough money for it but she gives me a discount
>walk home and spend the whole day in my new dress

>>45121712
Also a lot of millennial gays grew up before gender hysteria really kicked in so they were free to crossdress and engage in other GNC behavior without people making too big of a deal about it

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>>45120085
picrel

>browse early /lgbt/ since i was interested
>crossdress for a party
>pass except for the face and voice
>dissapointed so didnt troon

>>45122253
That’s like the perfect age to walk into a store and buy a dress for yourself because the saleswomen will think it’s adorable and bend over backwards for you

>>45122903
I bought my first bra and panties set at Macy’s when I was 14. I was terrified but the woman at the register didn’t even flinch

>>45121042
Have (You) posted yet?

>>45122002
Were they cute ones?

>>45122024
>cats dont recognize me, run away and hiss
Foreshadowing for your social life?

>>45122094
>looks horrible with my conetits
Did they ever fill out?

>>45122253
>try on a few other dresses and she helps me decide which one is best
What did it look like?

in the last of these threads i wrote something to the effect of:
>these stories make me sad cuz my memories of being a teenage crossie are all lonely, melancholy ones, and even though i've been transitioning for years at this point, i'm still not comfortable dressing feminine, nor do i feel like i'm free to or like it's a particularly good idea for me to do so
and someone else responded like:
>don't let your dreams die, nona. you should dress feminine.
and the thread died before i could think of anything to say in response and i've been thinking about it all week

>be 5
>get caught wearing a girl's dress in daycare
>humiliated
>parents had to change daycare
>emotional neglect
>develop agp as teen

>>45123873
>Did they ever fill out?
no, this was a couple months ago. idk if they ever will

>be boymoder
>go to club in the city
>change and do makeup with a hand mirror in a toilet stall
>sit on the sidelines scrolling on my phone and watching the people
>girl comes up and asks what the song playing is
>she hears one syllable out of my mouth and immediately walks away
>stumble out of the club overcome with shame
>catch a bus home without bothering to change my clothes
>guys on the bus giggling about how much of a faggot I am

>be me
>4/5 years ago
>just about to start HRT
>decide to go out with my friends for pride
>they encourage me to dress femininely so I can get comfortable with it
>wear a cute top and some baggy jeans to try and fit in with what my female friends wear
>put my hair in a ponytail
>put on makeup (concealer, eyeshadow, mascara)
>go out
>have a really good time, lots of people gender me female which was crazy to me at the time
>gets to midnight-ish
>decide to leave the club for some fresh air
>walk round the corner to the alley behind the club to smoke a cigarette
>hear voices behind me and a man’s voice saying ‘are you alright darling’ to me
>haven’t voice-trained yet so terrified to answer but do my best fag voice
>they get closer
>one of them says how pretty I am
>the first guy comes up close and starts to touch my arm
>not sure what to do and I’m kind of frozen at this point out of fear and confusion
>guy asks if he can kiss me
>say ‘I don’t think so sorry’
>pushes me up against a wall and starts to grope me and kiss my neck
>all his friends just standing behind him watching and smiling
>really panicking because I don’t know if they know I’m a tranny and don’t care or if they think I’m female
>guy moves his hand down to my crotch and tries to pull my jeans off
>at this point I finally snap out of my frozen state and push him off
>run back up the alley to the club holding back tears
>get back to my friends and just break down crying because I was so scared
It was a bad experience but it ultimately didn’t stop me transitioning. I just realised that there are lots of dangers that come with being perceived as feminine.

I almost never crossdressed prior to starting hrt. probably this is part of why these threads aren't big anymore, I've been on here since I was thirteen & developed a severe shame complex around being a tranny that I've only really started to unravel now in my twenties. I'm stealth now but still mostly wear masculine clothes. never worn a skirt. some relevant tidbits though:
>dressed up as a woman for Halloween when I was... ten? nine, maybe? around then. my stepbrother did too but he was less into it & about halfway through the night I got so embarrassed that I had to quit trick-or-treating
>older stepsister used to do my makeup sometimes. pretended to be ambivalent but secretly adored it
>after coming out around 15ish years old my stepmother bought me a training bra & some tucking panties & gave me the clothes that my stepsister had left behind when she left to live with her dad. I never wore any of it, the former two for shame reasons & the latter a combination of it all being tweenager apparel & not my style &not wanting to wear my stepsister's clothes. I have no idea why my stepmom did this for me, we don't get along now & had an awful awful awful relationship then. a couple years later she'd throw out everything I owned
thinking about this kind of stuff makes me really melancholy. I don't really regret my life but my childhood could have been so beautiful if I had been less weird & autistic & ashamed. there were so many girls in my life that would've loved to help me selfactualize wrt sexuality & gender. my actual transition (the parts other than hrt) was slow & miserable & now woman stuff is just very mundane. I cheated myself out of something meaningful

>>45124243
dumb & irrelevant recent anecdote involving dad & mentioned stepfamily:
>visiting dad & introducing him to my bf
>stepsiblings over too, haven't seen stepsister since pretransition because she doesn't get along with her mom
>first bf so everybody getting their first real glimpse of the depth of my gayness
>playing some party game where you have to ask questions to figure out a number everyone but you knows
>stepbrother's turn; has a high number; asks if he could father kids at that age
>I say "yeah but they'd have genetic problems & probably be gay & retarded. that's what happened to me" (my dad had me at 40)
>stepmom bursts into hysterics
>dad completely silent & stoic

i saw, i skinwalked, i came

>>45124275
brvtal
I love it

>Living with grandparents
>they don't force themselves into my room so I can dress up in peace
>getting too comfortable
>the bathroom was right in front of their room
>they must be asleep
>feel comfortable enough that I think I am making zero noise
>tho there's some obvious clacking
>hear some murmuring
>No , don't come out, it's not him
>Who else could it be?
>ran off to my room and grabbed some container
Didn't come out the next day, it not like it wasn't obvious but that was scary

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>>45124100
Rough

>>45124151
Did you get out of fagmoder stage?

>>45124191
>get back to my friends and just break down crying because I was so scared
What did they think?

>>45124275
>I say "yeah but they'd have genetic problems & probably be gay & retarded. that's what happened to me" (my dad had me at 40)
How much do you hate your dad? Because that was coldblooded.

>>45124572
>Did you get out of fagmoder stage?
I haven't girlmoded since if that's what you're asking

>>45120085
The only ‘interesting’ ones I have are just sex stories. The rest are just regular uneventful days.

>>45124828
tell us the sex stories!!!!

>>45124828
We're listening.

>>45124842
>>45125005
They’re really pretty much the same as rhe ones from last time

>>45124572
My friends were very supportive and nice, but the girls were keen to make me aware that going out like I did was stupid and that I needed to become more aware of how dangerous it can be. It was good advice and needed.

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>>45123035
Based

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>mid 2010s
>mom was travelling a lot
>yolo'd and spent several late nights dressing in her stuff and using her makeup
>would jerk off and whore myself on /b/
>compiled everything in a rar file with a password that I would show to a lesbian friend (never did and the rar file is long lost)
>almost got caught and stopped with a few relapses afterwards
>though I've been open about dating a boy once and she always knew I was a little faggy
>been living on my own since 2021
>never considered buying stuff and dressing up again
>what little time I have is spent playing vidya and doing chores
>I also got fat and ugly
the smell of those nylon stockings still lingers in my mind

>>45125033
when was last time

>>45125260
this is exactly what made f1nn troon out

>>45125425
get on hrt already

>>45123873
>What did it look like?
It was a very cute blue party dress from the 90s

Here’s the beginning of my catfishing story that I wanted to post last week. Have to leave now but I’ll try to finish it later tonight or tomorrow if the thread’s still going. Warning in advance it’s kind of an anticlimactic story though.

>beginning of summer before 8th grade
>be an openly gay little twink
>live with mom
>mom buys a condo
>we move out of our apartment
>can’t move into new place for six weeks
>temporarily move in with my fairly rich divorced aunt and two girl cousins
>one cousin is a year older than me, the other is a year younger
>we’re very close and my aunt is a big fag hag so it’s a lot of fun
>mom takes the spare bedroom but stays at her bf’s house most days so is barely there
>I stay in older cousin’s bedroom
>stay up late queening out and doing stupid teenage girl stuff with her
>we decide it would be funny if I posed as a girl and catfished various boys she knows
>not to brag but I could pass as a girl very well at the time
>we make an insta account for my new fake identity and name her Natalie
>tell aunt about the Natalie insta account but don’t mention the catfishing part
>she loves the idea of our little project and wants to help
>goes to her closet and digs out a long brunette wig that I can use
>need to get some good pics for the initial posts and pfp
>go to cousin’s room
>put on knee length pink dress and silver heels
>yes I wore a bra and panties too
>they do my makeup
>put on the wig
>aunt runs curling iron through it
>go outside and pose for pics
>aunt is way more excited about this than expected
>change into a couple other dresses, tweak the hair and makeup, take more pics
>that night cousin and I upload pics to the insta account
>she handles following people and getting followers to make it look real
>really this is all just so we can trick some boys later
>plan is to tell them I’m her cousin from out of town

>>45123873
>Foreshadowing for your social life?
Foreshadowing me passing and looking like a completely different person I guess. The only friends I kept around in adulthood were the ones who would accept me when I came out anyway.

>>45126056
>next day decide we need to get some pics of me out in public
>get dressed up again
>casual sundress, ballet flats, hair in a loose ponytail, sunglasses
>aunt drops us off at big outdoor shopping center
>younger cousin tags along
>roam around getting pics at Starbucks, in various stores, trying on clothes
>felt exhilarating going out stealth like this
>get back to the house
>upload pics to the insta account
>change back into boy clothes
>go to her friend’s house and hang out with a couple other girls
>don’t mention our little project to them
>we all leave to go see The Bling Ring
>meet up with three boys at the theater
>one of them has a massive crush on my cousin
>cousin randomly mentions a girl cousin who will be visiting (who doesn’t exist) in front of them
>next day cousin says we should get some sexier pics to keep ready to send guys
>she does my makeup in a more whorish style
>put on push-up bra and slip skirt
>watch a YouTube video about how to simulate cleavage with makeup
>looks pretty real
>take pics, swap out the bra for variety
>attempt some pics wearing a bikini top and wrap skirt but the boobs don’t work

We didn’t actually start catfishing anyone until like a week later. There was a lot more dressing up in the meantime so I can maybe include that if people want to read it or just jump ahead to when we started the catfishing.

>>45120085
My crossdressing "career" is mostly over. When I say it like that it really does sound like I'm John 50 or an old prostitute, but I am 35 and I will never be the young girl in cute clothes I always wanted to be. One chance at life. Yay

I got to do some things I wanted but mostly missed out on things I wanted.
>went to college crossdressed a few times
>socialized, played games or sports a few times crossdressed
but on the other hand
>never had sex crossdressed
>never got femmed by girls
>never went bra shopping with girls

>>45126235
Same, but without the first 2. At least i have tits now.

old man with aviator sunglasses and a motorcycle helmet that looked like those police ones from the 60s was riding a wide tired bicycle and assaulted me on the street by inching towards me with it after he stared at me.

>>45126235
>never got femmed by girls
Were you gay or straight? Because this one really only ever happens to gay boys

>>45126098
Pretty good so far. If you want to include it.

>>45126394
Bi. In the sex fantasies it's always been me as a girl with a male partner, fwiw

>>45126300
Having boobs would mean little to me if I was home alone. The excitement would be in socializing with people while keeping the boobs hidden

>>45126394
>>45126452
*Closeted bi
I guess being openly gay would be pretty necessary

>>45126472
you mean boymoding?

>faggy kid, closeted, always made fun of for looking gay, have a feminine voice (though not a fagcent)
>crossdress here and there in my mom's or sister's clothes but eventually try to repress and be "straight"
>somehow find a gf
>we have cute dates together, we share our deepest darkest secrets, cry on each other's shoulders
>feel so relieved i can be free from the AGP-faggot-virus
>still give in to the crossdressing urges one day when alone, feel terrible about it
>pray to God to not punish me over this
>YHWH doesn't listen, so she eventually starts growing distant
>very subtle at first and reason that all relations wax and wane in some way
>eventually can't rationalise it anymore
>terrified of losing her however, so do nothing about it at all
>starts being kind of antagonistic rather than just distant, so try to confront her *calmly*
>she flies into a red dark rage, genuinely the most mad i have ever seen anyone
>break up
>eventually find out she's been cheating on me since at least the latter half of relationship
>guy she cheated on me with is so conventionally masculine, feel so heartbroken and inferior
>genuinely spiral into breaking down every night, being sick all the time, cutting myself, want to kms
>give in to being a faggot tranny because the Fates just don't want me to live normally
>start crossdressing again, but with my own discretely purchased clothes this time
>ex then spreads the rumour/my secret that i'm a CD faggot
>bullied everyday, even my parents find out about the rumour and ask me if it's true in a roundabout way
>deny it, unsure if they actually believe me
>troon out at 20 and essentially decide to live a new life after that, completely cut off from the old

don't really care all that much anymore about this, i accept what i am unconditionally, and i'm genuinely happy and fulfilled with my sexual orientation, career, life, etc. now, but it was really traumatic for me to go through this so early in my life

>>45128126
lol fag

>>45122881
>they were free to crossdress and engage in other GNC behavior without people making too big of a deal about it
What world are you in? Hippie liberal areas still allow this, Christian areas always despised this and called it satanic.

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Here's one from when I was pre transition but trying out crossdressimg irl
>be me 22 with gf at the time
>twink
>can semi-pass with right clothes and make up with my hair straightened.
>she is helping me explore my feminine side knows about trans feelings
>first time out we went to dinner it was successful no hate just a nice dinner
>this time decide to go to hooka lounge/bar
>get there
>very hood atmosphere
>only white people there
>go to order
>some girl comes up to me
>"what is your doin?"
>freeze
>partner covers for me "its her first time out" implying I dont go to bars
>"get her some water or something"
>after she leaves we gtfo
>try another place vibe is immediately off and leave
That was such a weird experience.

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>>45122903
>shadman
Its a shame he couldn't just keep doing stuff like this and meme comics and had to turn out to be a pedophile. I loved his stuff before he started doing Loli and I had to distance myself from ever having liked him at all. Sucks.

>>45128204
I believe the point is that adolescent/childhood crossdressing used to be considered pretty standard behavior for gay youths and nowadays a lot of people use it to question gender identity

>>45127761
Well, think about how young men and young women dress. The girls do wear a lot of outfits that would be really "gay" for a guy to wear, but the rest of the time, they dress as casually as young guys do in a t shirt and athletic shorts or joggers. For a foid going to class on a Tuesday morning, her outfit is externally indistinguishable from the outfit of the dude sitting next to her. I went for that feeling when I crossdressed. My exciting secret was I was wearing a fucking sports bra and boyshorts underneath my outer clothes. I fucking loved feeling like a comfy zoomette.

Girls wear bras to cover their breasts. Something so mundane in the female experience made me unbelievably horny when I imitated it.

>>45128324
It's still allowed in liberal areas, especially ones with people who chant "clothes have no gender" and the like
Just because some people mistake you for a tranny rather than a faggot doesn't mean society has become le bad suddely

>be me, 23 KHHV neet buff manlet
>been gooning to Chinese trap cosplayers for years
>spends most of my time shitposting on 4chan and playing games
>popular on /fit/ for my pictures, some are turned into memes
>femboys are becoming really popular
>ok I wanna try too
>takes few slutty pictures and posts them on /soc/, /fit/ and /LGBT/
>people like them, ask for more
>takes tummy picture with good angle from my bed
>posts on twitter
>instantly retweeted by the biggest person in the industry back then
>starts buying some agp clothes and swimming into attention
>never got so much attention before, my brain is melting, I cannot think about anything else, wants more
>ends up with femboy stuff, a corset, stockings, leather harness, fetish things
>shit I look good in these...
>making a few bucks off onlyfans
>this lasted for about a year
>managed to pull a trans girlfriend off dating app, deleted all my shit (she knew), threw all my stuff
>been together for 5 years, left 4chan for 5 years, only lurking to see people posting my pictures from time to time
>broke up in July 2025, haven't met anyone since, lonely and depressed
>back to 4chan to get attention
>now impossible to take off on twitter, there's no attention for me anymore
>29 years old, depressed buff manlet, pretty much living like a neet again, haven't crossdressed again because cringe and don't want to spend any money, becoming KHHV again

>>45120085

I’m 100 percent convinced I once encountered a ghost while dressing up

>be 13 years old
>parents know I’m gay but keep my crossdressing a secret
>have big stash of girls clothes and makeup that my friend and her sister gave me
>live in 100+ year old house
>mom thinks it’s haunted but I’ve never seen anything
>parents are at a wedding all day
>time to get dressed up
>put on dress and heels
>sit at my desk putting on makeup
>using my laptop camera as a mirror
>listening to music
>hear what sounds like footsteps behind me
>wtf
>turn off music
>listen for a bit but don’t hear anything
>keep the music off
>finish doing my makeup
>walk over to floor length mirror and check myself out
>suddenly hear “you look really pretty” in a loud female voice
>sounded like a teenage girl standing right next to me
>completely flip out
>this happened at like 11AM which somehow made it even scarier
>eventually calm down and accept there was a ghost in my room but it’s probably a nice one
>stay dressed up for next few hours
>never encounter the ghost again

>>45129162
>eventually calm down and accept there was a ghost in my room but it’s probably a nice one
I wouldn't sleep for the rest of the night.

>>45125448
I posted one like a few days ago on the last thread

>>45130476
I think part of me was just glad it thought I was pretty

>crossdress my whole life since childhood
>agp, agamp I don’t know
>try being straight guy for most of my life
>never works
>decide I’ll actually go to club with my CD friend
>it was great time
>felt happy for days after
>start talking to man online
>he’s a doctor who likes troons and crossdressers
>get dolled up
>meet up with him for drinks
>he starts getting handsy and it’s turning me on so much
>go to his hotel
>this is the first man I’ve ever been with
>immediately start passionately kissing
>my tuck has come undone at this point because he was groping me the ride over here
>I pull down his pants and start going to town
>he pushes me on the bed and starts giving me head
>I have to make him stop because i want to have actual sex and not cum right away
>I start riding him cowgirl
>omg this is real
>I can feel myself about to cum
>omg it’s nothing like I’ve ever experienced before
>it just keeps shooting
>whole body feels orgasm as I feel him cum inside
>no going back

>>45123962
still here, still thinking

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As promised.

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>>45133221

For comparison, my AI rendering of it lol.

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>>45120085
Been doing this for decade so I have a lot of stories. I've posted on a few CD threads here before... I wonder If I've told this one before? Can't remember.

>Be me
>Asian guy, bullied in growing up bc I was short and weak.
>enter high school, i'm 90lbs and 4'10.
>gym teacher tells me I'll grow
>graduate now 95lbs and 5'0
>gym teacher tells me I forgot to grow
>go through early adulthood with a major inferiority complex
>discover crossdressing through anime and cosplay
>realize I've been genetically gifted by god with the ultimate crossdressing stats
>I'm short, petite, and have a naturally androgynous face midface is short, nose is small, jawline is not very masculine.
>start buying girls clothes in secret, I still live with my parents and don't want them to know
>On a family trip to NYC I go to uniqlo and buy the cutest panties with bears on them
>One day I come home from crossdressing and take everything off except those panties bc I want tow ear them a little longer.
>wear them all day then when I'm gonna take a bath I put them in the hamper with the other used clothes
>mom finds it and grills me, I tell her I like crossdressing
>I thought she'd be mad but she'd very accepting
>on halloween she helps me with my makeup when I dress up as Megumin
>dad accepts me too
>tfw I have awesome parents who gave me amazing crossdressing genetics
>pic rel is me on a trip to Hawaii where I got my hair cut.

>>45120085
Is there a good crossdressing guide?