Sup, fags. Let's share some gay stories. What's the gayest thing you've done? What's the best gay experience you've ever had?I have plenty but they all revolve around me dressing like a girl and letting guys fuck me.Gayest I've done: Blow three guys at once. One dick in the mouth and two in each hand
>>955789566Post my sissy dressup on 4chan
>>955790439wanna share it again? I'm a sissy too
>>955790493
>>955790579sexy. I like wearing panties like these when I meet up with guys
>>955789566>What's the best gay experience you've ever had?Spent a few days as a live in naked petboy for an old man while his wife was away. I was 18.
>>955790849What was it like?
>>955790717Haven't had a lingerie meetup with a guy. They always flake or send me a thousand texts/DMs to creep me out.
>>955790985Honestly incredible. Within a few minutes I was naked in his living room. He had me wear a tail plug and mitts and I spent most of my time on all fours. He put a bell collar on me too. He tried to put a bell on my dick but since I naturally got hard or soft throughout the day it kept slipping off so he put it on my tail instead.
>>955791097I'm lucky. I have a current guy I'm hooking up with who's the best. I dress up for him and he treats me like a princess whenever we get intimate. I'm thinking of wearing this for him next time I see him
>>955791104That's too extreme for me but the tail but plug and mittens sound hot. Furthest I've gone with animal stuff was a maid outfit I have that has cat ears
>>955791234Very cute! It wasn't all that extreme. Though I did have my food out of pet bowls lol. He let me sleep in his bed but otherwise he set up cushions all over for me to roll around on. I think he really just liked seeing a naked boy crawl around his house lol
>>955789566>What's the gayest thing you've doneI cum from riding dildos lolWorn thigh-highs, hotpants, a skirt, a girly top and arm sleeves with thumb holes. I tried the whole femboy thing and i felt nice in the clothes but femboying about isn't for me.Aside from that i recently put up a post on a local meet-n-fuck website looking for women and twinks/femboys.I never touched another dick or another guy sexually but i now for a fact i want to try it at least once before i get older. I think it's mostly curiosity and i can't say for sure yet whether i'm truly bi because i'm into pussy most days and then just have a random day where all i can think about is sucking dick and being sucked off by cute twinks, but it might be fetishism from almost three decades of porn consumption.
came inside a twink's ass
>>955789566>What's the gayest thing you've doneNever in person but I dress up on those random camsites a lot. I try to get as many men to cum for me as possible. And if i find someone really lewd i cum for them :3
>>955791456I'm bi too but I also get that craving for cock lolI'm the opposite in that being girly and wearing cute clothes is the only way I'd feel comfortable sleeping with guys
>>955791195Cute outfit, I'm jealous of your heels. I would love to do some cosplay dressup with a guy where he picks out one of his favorite characters and make his weekend.
>>955791565I like dick but i usually really am not into manly men. Ideally i want to try it with a femboy, problem is they all want to just get fucked in the ass and some don't even really want you to satisfy them, they just want to be buttsluts. Or so i heard.
MMM threesome with an older couple as a birthday present for one of them.
>>955791651NTA but I had a friend I lost contact with who wanted us both to dress as shimakaze. Shame we never did it but we were inspired by that famous doujin that I'm certain made us both gay
>>955791651thanks! I love those shoes too. I'd love to just dedicate a day to the guy I'm currently seeing and be his little snowbunny femboy for him. I'm a bit of a size queen and his bbc reached deeper in me than any other guy before so he sorta makes me swoon lol
Gayest thing would probably be sharing a room with my older brother and him showing me porn and telling me how to jerk off. Having bunkbeds, We started watching porn together in his bed and started jerking each other and eventually blow jobs…..i gave lots of blowjobs in that bedroom.
>>955791767That sounds cute. How did it go?
>>955791781fuck that's hot. I've always wanted those stockings that character has
>>955789566Met a tranny off craigslist, invited them over, fucked them and came all over their face. Sent them out the door without giving them a towel.Fucked a CD in a WeHo hotel. Came down his throat.
>>955791668>>955791651I want a man to play with chest more than my butt. Straddling my chest and playing with me, touching my lips and face.
>>955791847I think those stockings are the first girl clothes i ever bought lol. That and a microskirt
>>955791955I had one micro skirt. Only wore it once for a guy who's dick was as big as mine. I sent a pic of the skirt to a female cousin and she replied "so slutty i love it"
>>955791781That feels like a real missed opportunity. Though Shimikaze sex sound like fun.>>955791803Make the day happen, anon. He'll like that.
>>955791836I walked funny for a bit afterwards lol. It was mostly just me and the top/birthday boy.I can go into more details if you care.
>>955791907That's quite romantic, actually. I like when sex gets sensual like that and focuses on the wider sensations rather than JUST pumping. Hence my frustration about "those" twinks/femboys just wanting anal cause i have a huge oral fixation and typically crave cum on face/in mouth, whether i deal it or take it, whatever sex my partner is, doesn't matter. The thought makes me feral and the act itself makes me feel calm and gratified after. But before then i'm all about careful touches, intense kissing, dryhumping and soft verbal teasing.I'm sure i'd be a pretty good partner after a couple of experiences (with men that is, i already had a couple of pussies)
Had a long term substitute teaching position for a while at a high school. Became really good friends with another young male teacher. He confessed to taking creepshots of the pretty girls in his class. I asked him to show them to me. I got horny. I admitted it. We smoked some weed and just scrolled through his pictures. He fucked me in the ass while calling me his girls names. Did this for a while until he suddenly quits one day. Turns out he'd been flirting with one of the girls over text and got caught. The school told him to quit or they'd report him.
>>955792032i'd love to do something to make him happy. during our first time, he poured us wine and kissed me, complimented my looks and the dress i was wearing. He's also buff and hung like a horse so I have a bit of a crush on him. I told him I felt like a princess when we smashed and told me I am one. My butt and mouth are his for the time being lol
>>955792024That's incredible anon. I wish I had someone that close who i could share that with. It's hard keeping these feelings inside, you know? A confidant would be so nice. >>955792032It's one of my biggest regrets. Impossible for this to happen again. >>955792062Yes please!
>>955792220one cousin i have is the reason i learned to love sucking cock lolShe told me it was a mentality thing. Then I might a guy, blew him, enjoyed it and I texted her that it worked lol
>>955792367That's really cool. It can't be understated that I think a big thing guys lack is someone they can rely on as a friend who encourages them to be themselves. Guys always have to have a shield up. It sucks
>>955791828Bump
>>955792154>But before then i'm all about careful touches, intense kissing, dryhumping and soft verbal teasing.It just dawned on my that i'm one of those mythical dom bottoms. Probably. But only with men.>>955792367I mean it probably is, i'd still have to try sucking myself but when my ex initiated oral but was really shy about it cause it was her first time, i took her by the hand and walked her through it and she told me she sort of "slipped into a cozy headspace" a little bit into it, to paraphrase, and then didn't need me to keep guiding her. And that happened like a minute or so into her full-on sucking. I think it's just the initial "am i really doing this?" feeling. Seems understandable.
>>955792591"just put you back into it" is what I was told. She said a sorority sister told her that and she felt like it made a difference for her. What also may have helped me is that the first guy I blew with that mindset was very muscular and had a hot body
>>955792154I get a ton of messages from chasers telling me they want my body or how I'm the most beautiful cross dressing woman they've ever seen. But if I ask them what our date will be like they just mention sex. I want someone to look in my eyes, touch my lips and really tell me what is beautiful about it. Probably why I haven't had sex in a few years X.X
>>955792813Better to not have any sex than have it not feel fulfilling because they don't want to treat you well.>But if I ask them what our date will be like they just mention sexLmao come on man, the least i'd do is take someone out for a coffee. That's very standard and probably boring but it's something. That or shopping, maybe a faire if one's in town. No need to reinvent the wheel, it's about courtesy. Personally if my first time with a guy went along with my fantasy of how it'd ideally be, i'd wanna stay a night with him, get home, relax in front of the TV or movies and maybe share a drink or two, then start seeing how he reacts to me coming onto him. And ideally i kiss and touch and caress him so much he starts begging for it to get sexual by himself.
>>955792813Same boat. Crossdresser. I don't date guys, but the one i'm sleeping with is absolutely giving me that kind of treatment you're seeking so I don't mind just going straight to sex since I know we'll kiss, he'll call me pretty, and I know I'll get a kiss goodnight even after the dress is off and the makeup gone. He said he'd give me a lap dance next time since he used to be a male stripper
>>955789566>posted before, butMale cousin and I kept each other satisfied at an age way to young to post here.
>>955792220I was like 19 or 20 at the time and bicurious, but wanted to be discreet so had turned to Craigslist circa 2010.Replied to an ad looking for a twink bottom and learned it was a couple in their late thirties that had agreed to add a third wheel, but the dom, top guy didn't know his partner was actively looking. They went out for a birthday dinner and wanted me to meet at the bar, but since I was too young it kinda ruined the plan and I waited for them in the parking lot. We chatted super briefly and then drove back to their apartment. Birthday boy disappeared into their bedroom, but the other guy makes me a drink and starts sucking my cock. We move to the bedroom and there's a full array of lubes and condoms being spread out.We suck the birthday boy together and when he's ready I lay back on the bed and let him slip it in. Other guy at this point is just watching and occasionally sucking on my nipples. We switch to doggy and I cum almost instantly into their sheets but don't tell anyone. This causes me to tense up a bit and that apparently makes the guy lose it and he shoots ropes all over me. Bottom guy helps me clean up and I waddle out.
>>955793216Not reading all that attention span is the least of my time.
>>955793258Fuck off retard
>>955793216>We switch to doggy and I cum almost instantly into their sheetsi have to wonder if i'm doing something wrong or real dick is that different but if i ride my dildo i go soft unless i put on cockrings. But WITH cockrings on when i ride it i'm on edge quickly and stay there really long and start leaking like a slut, whole cumloads' worth without actually cumming, and then when i actually cum it's another load the same size. But like someone actually fucking you probably just gives different sensations, plus the psychological aspect of it.
>>955793216That's awesome! Sounds like it was fun :3
>>955792999You sound like a nice guy with your heart in the right place. You should try your approach, even on an ass up twink. You'll probably make hers or my day :)>>955793002CD too, you're very lucky to have it but you're probably adorable.
>>955793432Thanks. When I first met him, we wore grey sweats when he let me in his place and it was the biggest bulge i've ever seen in my life. I remember thinking "that 9 incher is somehow going in my mouth and my ass tonight" lol>>955791195This is a pic of me and I think i'm wearing this next time for him. He said I looked hot in it :3
>>955793582You do look good there.
>>955793404It was both the physiological aspect as well as the physical. I had played with toys before but having someone else grabbing my hips and bouncing me on their dick was crazy. Add in the sounds and feeling of our bodies slapping together and I couldn't hold out to save my life.
>>955793432Thanks for the compliment. Yeah i could probably land a cute guy, but as i said, if i do i want try the whole nine yards, including cuddling and oral, not just in-out. I don't want that shit to be clinical, i want it to be warm and human so i can figure myself out.
>>955793678He has a nice little bench in front of his bed and I love sitting on it because it means it's blowjob time. I feel like a queen sitting on it, glass of wine in one hand and his yummy BBC in my mouth. If it weren't so risky i'd let him creampie me. Don't want to date him, but whenever I think of him, i long for his body and the ways he's fucked me
>>955793683>Add in the sounds and feeling of our bodies slapping together and I couldn't hold out to save my life.cue that one time i was riding my dildo and having a hard time cumming, then switched to a smaller one cause it started hurting, bouncing on it for a little bit, feeling and hearing my ass slap against the floor wetly from all the lube and not even taking another 15 seconds to dribble like a faucet then another 15 to shoot ropes everywhere. That shit adds more than i thought.
>>955793905Try straddling a body pillow while you do it. Have that bit of resistance keeping your thighs spread and you close your eyes feels amazing while your ride.
>>955793432One time, I was so horny for him and it had been a few months since we made love that I pulled up our old grindr chats just so I could look at the dick pics he sent me
Met up with a dad once when I was 17 and sucked him off and he sucked me off
>>955795723did you like sucking or being sucked better?
one time i went to an adult movie theater and had a circle of guys watching as i gave someone else a blowjob
>>955789566Started rolling in ass roll threads on this board
>>955796780did it lead to you letting a guy fuck you?
69 with an old guy in prius outside of my gym
>>955796863Nah not yet still a bit shyI do want to go to a glory hole booth in an adult theater to fix that issue
>>955797032I like adult theaters if my guy isn't available. I rarely go. I do live near one that's know as a spot for crossdressers and it's chill because I go there and use the ladie's room to change and do my makeup. It's good if you just want to suck a cock. But if you already have a sexy man, it's not as fun. It's enjoyable but you do feel like a whore after
>>955797212I agree with all of that but im pretty shy, it is a shame because anons do like my butt and I would like whatever guy is in it to see it
>>955789566i got raped repeatedly in foster care. Wasnt fun.
>>955797367why do you feel shy?
>>955789566>What's the gayest thing you've doneOpening this thread
>>955797558just a shy person in general
>>955797561guilty as charged. I'm OP and i'd be lying if I said i didn't like giving blowjobs
>>955789566A guy on grindr blew me until I nutted. Then I sucked him off until he came. Then he blew me and swallowed again and then I left
