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I like to crossdress very much and wish to have sex with males and have fun like a woman.
When I was younger (I won't say how old) I used to talk with older gay guys online. I eventually started taking pics and even taking requests for what they wanted to see. A few wanted to see me in panties so I would swipe from my sister's dresser and put them on. I guess they looked good because more and more guys wanted to see it. Eventually it led me to buying a wig and putting on my sisters clothes & makeup for them. It then went from pics to vids of me stripping and masturbating for them. Thinking back now about it turns me on so much. I often times wish I was a girl.
Recently made an onlyfans so I can descretly post my crossdressing photos. I love wearing cute panties.
I was an 18 year old, discrete crossdresser. I stole my aunts high heels and my cousins gymnastics leotard and gave head to another man. I felt sexy as fuck.
I was 15 when an older cousin told me we could go to this older mans house and he'd blow us and give us each $10. I refused several times, but once after 3 beers I was ready. I'd only masturbated before other than at age 8 through 10 played with my cousins pussy. I was very apprehensive going into this place and didn't want anyone to see me. We got there and this long haired guy of about 40 years or so gave us some beer, some pot, and my cousin dropped his pants and sat in a chair across the room from me and the man got on the floor between his legs and gave him a blowjob. After my cousin said that it was my first time, so the man told my cousin to leave and he'd get me home.
"You a virgin" he asked me and I told him the truth. "Stay here I have something special for you, will you wait for a few minutes?" I said yes, and I think he didn't believe me he said he just wanted a taste and made me take off my clothes and sit down and put my cock in his mouth. It felt great but he stopped. He took my clothes in his bedroom and told me to wait.
When he came out SHE was totally dressed sexy as hell. She had on make up, a sexy nightie, stockings and styled long natural hair. "I'm going to take all those nasty little virginities away today." he/she said in the most feminine voice you could imagine. She turned down the lights, drew the drapes, and took me naked to the bedroom.
While there she first blew me, then kept playing with me until I got hard again, and I was rubbing his/her ass, and found out that she had small little titties. They actually filled out her A cup bra. They were nice and natural, very soft, with puffy nipples. "Hormones" she said, "You like?" I told her yes and my cock was hard again as I was sucking on "her" titties. I was playing with her panties sticking my hand down them like there would be a pussy, and she had a tiny little cock which she made me call her clit. It was pulled between her legs and her perfectly trimmed pubic hair really made her look like she had a pussy. I was rock hard now and she pulled me on top of her while she was on her back and spread her legs. "Look at me baby" she said as her hand slipped my hard 8" cock into her soft, willing ass. "When we're like this it's my pussy, when I'm on my belly it's my ass" she explained. "You like my pussy baby?" I replied it was wonderful and she started rocking back and forth and I picked up on the movement. I was sucking her tits, squeezing them and when I was about to cum I couldn't help it I kissed him/her. Her tongue danced inside my mouth and I rammed it into her and shot a mega load of cum (at least 10 to 12 ropes) up into her manpussy. Kissing me in her afterglow like a woman would, I kept my cock inside until it grew soft and slipped out. With that I rolled over next to her. We kissed, I played with her clit and those really nice soft titties.
She pushed my had down to her clit and I didn't want to be a "faggot" and suck cock and told her so. But she told me that she'd done everything for me, and now it was her turn, and I needed to learn to let the girl cum too. I made her promise that she wouldn't tell my cousin that I'd done this, and she promised. I went down on her and started sucking her cock. She blasted a tiny load in my mouth and I swallowed it all.
After that we both relaxed in the living room a bit, with another beer for me and some pot for us both. It was really strong pot, and I was lying down on the couch with her kind of behind me and I felt her finger rubbing something wet on my butthole. She was lubing me up, stuck two fingers in and it actually didn't hurt too much. In my stoned state it was pretty good. I didn't say a word and she whispered that no one would ever know but I had to lose all my virginities and this was the last one. She fucked me with her tiny little clit (about the size of my middle finger) and came in my butt. I got up to go to the bathroom to get it out of me and when I came back she was lying on the bed on her hands and knees, with her panties down her leg with her ass up in the air asking me to fuck her in her ass. I did, I came, and she gave me my clothes along with $100. She said I could come back anytime, and I did. I must have gone to him/her at least 150 times in the next year or two. Maybe more. Some weekends I'd fuck her all day long. I actually let three (1 at a time) guys who were over to see her fuck me, and I sucked at least 10 cocks for her. She paid me each time, but I think she charged them, I was never sure and didn't care. I got to fuck all I wanted and she was a gorgeous woman when dressed and made up. It was 4 years before I managed to get a real woman to allow me to fuck her.
#crossdresser #mm #virgin #anal #oral
I am a boy, late teens. I am not too big, not a jock, and girls never notice me. I finally got a girlfriend who is great for me. She is a bit of a fatty, not too big but about 5ft. 8in and weighs about 185. She was quite experienced in sex already, in fact very very experienced but I don't mind. I get to have sex in all ways, places and do everything I wanted and even more. She has red hair, and is 3 years older than me. She is pretty kinky in sex and I do whatever she wants so I can keep having sex. I rather like some of the kinky stuff. She has made me be the submissive one in our relations, she is definitely dominant. She has even taken me to a public beach wearing a girls bikini bottom and a collar with a leash. When we were walking back to the parking lot she moved me behind some trees and bushes and we had great sex then left. She even did it with another girl and let me be in bed with them, then insisted I do it to the girl too. The other girl was really totally lesbian and didn't want a guy at all, but my girlfriend made her do it, and made me do it to her.
About 4 days ago, she took me over her lap while I was naked and started spanking me, she spanked with her hand and then a hair brush for about 20 minutes I was in a lot of pain, my butt was red as a Crayola crayon. She then rubbed some lotion on my butt to soothe it a bit, and started sticking her fingers in my hole. After three fingers were in, she started fucking me with her fingers, I objected and she pushed me down and told me if I ever want to feel her ass, mouth or pussy again I'll just lay there and take it. She fucked me with three fingers for about 10 minutes all the while talking nasty and calling me names, saying I was gay and liked getting it up the butt. Then she stuck in one of her vibrators, and turned it on. Then she called me all kinds of names because my cock got hard. She fucked me with that vibe for about 30 minutes, then let me up, made me clean up "my" vibe, and put it in a special drawer. About two hours later she let me fuck her and I again had to lay across her lap endure an endless spanking, and a 30 minute fuck with the vibe. She then stuck in a plug. I had to go home, and she told me to leave it in until I came back, to take it out only when I had to sit on the toilet. I did it and the next day didn't see her until about 5 or 6 o'clock, by then the vibe was quite loose in my backside. We sat on the couch and were kissing, I was playing with her very big titties and sucking her nipples. As I reached under her skirt I felt something strange. I pulled up her skirt and there was a cock in her pants, she also was wearing a pair of my underpants. She stood up, pulled off her dress and then the bra and had me pull down the male underpants. She had a strapon cock and was wearing it. "Start sucking bitch" she almost snarled, "or get a real spanking not just one of those love paddles I've been giving you".
I was on my knees and started sucking the very large artificial cock. She made me suck for a while, then we went to the bedroom and she had some stockings and lingerie for me to wear. I didn't want to, but she kept reminding me of how much I liked sticking my "little wussy cock" into her pussy, mouth and asshole. As I got on all fours on the bed after dressing for her, she pulled out my plug and stuck the very lubed, very large strapon up my shithole. She didn't give me anytime to get used to it, just started fucking me, very rough, very hard.
This has become our normal sex now, she fucked me dressed up like a girl, and I jack off while she does it. She even had that lesbian girl who she made me fuck, come to watch, and she was wearing her own cock and fucked me too. The lesbian also took me home to clean her house, all the while, even riding in the car I had on the lingerie and just a robe to cover but it didn't cover my stocking'd legs and high heels. While there she spanked me and tied up my cock and balls very painfully because she said I raped her. My girlfriend says next week we're going to the beach with me wearing both halves of the tiny girls bikini.
#bd #nc #crossdress #strapon
I was so horny yesterday and hadn't had sex in a long time. I found a twink online, went by his apartment and was fully intending to fuck him with a rubber on, but instead ended up with my dick in his mouth, then bending him over and giving his asshole a creampie. As I pulled out, it was leaking out of him, I'm normally not a big cummer but this was probably the biggest load I've ever shot. I hurried up and wanted to leave, he talked me into staying for a bit, I got a beer and we talked while he had some straight porn on the TV in his bedroom. His ass was pointed up and his hole was gaping open with my cum leaking out. I fucked him again, he tried to jack off his little dick but I wouldn't let him. I kept pulling his hand away, rubbed his pubic bush, and his nipples like I would a girl if I was fucking her in the ass.
I hate the fact that I did it to another guy. He was dressed in stockings, garter, a camisole which was like a small bra up top, he had very long sexy hair too and was in full make up. But still I fucked a guy and let him suck my dick. I shouldn't have done it, but I needed to come so badly.
#mm #crossdress #homo
She loved to embarrass me and dominate me. On one particular night, I went to the bar with her and her gorgeous room mate. At the bar I was playing pool when she decided to distract me by grabbing my balls when I bent down. Suddenly I realized she was letting other girls do it too and I had no say in it. I was groped by every girl there nearly. When we got back to her place, her room mate went to bed but left her clothes in the bathroom. I had to wear them and risk being seen by her room mate. I managed to avoid being seen but had to pose for pictures dressed like that and completely nude, which she left where her room mate would find them and take them. What a night.
#crossdressing #femdom #embarrassed #cfnm #bra #flash #panties #public
I started dating this really skinny girl in a city I was working in for 6 months. She was skinny, with short black hair, a nice looking face, somewhat of a tomboy I thought. She was living in the city full time as opposed to me. After about 4 dates she finally admitted she wanted to have sex but had no boobs whatsoever, and knew most guys were really into big boobs. She also said that since she was young, and even before she ever had sex, she'd had guys and girls tease her constantly. Some guys wouldn't even go ahead and have sex with her because she had a totally flat chest. She also said she was a little kinky about sex and liked normal things, but only if she could have it lead to some other stuff she really liked. I told her I was very amenable to trying new things and simply would say if I didn't like it. She then asked me about her lack of chest and I told her that I didn't think it would be a problem. She told me to stop where we were going, to order in some pizza and go back to my apartment.
She made me order, then had me strip, and went to the bathroom and came out totally naked. She did indeed look like a boy. Small frame, no hips, very little take-in at her waist, nice roundish little butt though, and this big patch of very thick hair on her pussy. I didn't say anything, just pulled her over to the bed and she asked me not to mess with her nipples as it made her feel bad. So I kissed her, and she reluctantly kissed me back, I reached to feel her pussy and found a 2" clit that looked just like a small uncut penis. As I rubbed her it grew to three inches. I'd never encountered that before and I loved it. I finger fucked her and she had me roll over on my belly and got on top of me and ground her clit into my ass crack. She started kissing me in earnest, as I craned my neck to her lips while she was lying on top of my backside pumping for all she was worth. She was bucking back and forth and I told her to stop a second and reached back, spread my legs and my buttcheeks and told her to put it in my butt. She used her pussy juice as lube and got her clit about 2 inches up my hole. She fucked me like crazy and even came twice. The doorbell rang and she jumps up I thought to go to the bathroom and hide, but instead she put on one of my tee shirts and a pair of my underwear, my tennis shoes and answered the door. She looked just like a guy.
She came back, got pulled off the underwear and said "I guess you should have a turn before we eat" and let me fuck her pussy in missionary position, again her kisses were very shallow. We ate with her wearing the tee and my underwear and me wearing nothing. When we went back to the bedroom she kept on the underwear and shirt, and had me kneel on the floor while she stood up with her clit in my mouth, sticking out of that super thick black pussy hair. She came again, and then she did the same to me. I loved it she sucked really good. Then she bent over with her arms on the bed, standing next to it, pulled down the boys underwear just below her ass and inserted my cock into her ass. She and I both loved it. It was my first time fucking an ass.
So after a few weeks she now dresses 90% of the time as a boy, and we spend equal amounts of time getting buttfucked. She likes to keep on boy clothes and be a "gay guy" and get buttfucked. Even when I fuck her pussy it's mostly from behind. She fucks my ass too.
I started dating a girl, and ended up in a gay relationship with her. . . him.
But I still like it. It's not normal that's for sure. I don't know what I'm going to do when I have to leave. I really like this situation
I am a 25 year old male and I fantasize about being dressed up like a little girl. I would give anything for someone to feminize me.
When I was about 13 I sneaked into my younger sister's room and looked through her wardrobe. I found this blouse that I didn't remember ever seeing her wear, it was a pink satin slip on with a round peter pan collar placket and short frilly sleeves. It was so ultra girly that she'd probably never be seen dead in it. I'm not sure why but I sort of dared myself to put it on even though it was far too small. I had to put my arms really close together inside it and put my hands into the arm holes. Gradually I pulled it down until finally I had it on. Then I did up the buttons one by one, right up to the top. I couldn't believe how sissy I looked in the mirror, or how hard my cock was getting. Looking through her drawer, I found a pair of short pink nylon pyjama panties with flowers on them. Trembling, I put them on over my hard cock. The feel of them hugging my ass was amazing. Finally I put a pink skirt on to complete the outfit. Seeing myself dressed as a little girl in the mirror was too much, I masturbated like crazy and came half way across the room.
I'm a married man. Love my wife. Also have a guy who is bisexual just like me. He loves me and i love him too. We have crazy sex when ever we meet. He considers me top but I'm more of bottom slave. I like to be roughed up. He makes me feel good. Lovely person.
#gay #married #bottom #slave #crossdress
I have been married a long time, and when my Wife goes out, I dress up in her lingerie and clothing and go out to local adult video shop to have sex with other men. Most of the time I just give blowjobs, however on a few occasions I let them have intercourse with me and not use a condom. I enjoy being seen after having been used that way, and have their cum running out of me into my Wife's panties.
#gay #homosexual #crossdress #suck #swallow #fucked
I want to dress up in pretty lingerie and go to a party with other guys wearing pretty lingerie. I'm straight but want to touch a hard, panty covered cock. I want to make him cum.
#panty #crossdress #sex #confession
I'm a 31 year old married man with 2 kids. I crossdress, and meet men to give them blowjobs often. I also go to the adult bookstore for orgies and random gay sex.
I have been a closet cross dresser since age 11. 30 yrs later I still love to dress up as a girl (preteen to late teen styles) As I have gotten older I have only grown to love dressing up more and more..staying fully dressed as a girl for a week which I find myself acting like a young girl. I am always buying hosiery dresses,skirts as my girl wardrobe has surpassed my male wardrobe by far.
I'm a 16 year old male (for real; I'm not trying to bait anyone, or anything). I've always looked somewhat feminine, taking a lot more after my mom than my dad. When I was younger, I was even occasionally mistaken for a girl. That said, I'm a junior at a fairly progressive high school, and in my Drama class before Winter Break, I played the role of Juliet in Shakespeare's Romeo and Juliet. My Drama teacher is sort of weird. He's also VERY particular about the craft, so I was fully costumed and wore makeup the day of. To top it all off: it was a kiss scene! Now for the confession: my partner, playing Romeo, wanted to do the "thumb trick", where I would end up kissing his thumbs instead of his lips. I said okay, but when the kiss happened at the climax of the scene...I moved his thumbs away! He was really embarrassed, and so was I, but in the moment I felt really compelled to do it. I tried to apologize afterwards, but he just dismissed it...I'm not sure what to do now...
#juliet #shakespeare #drama #highschool #romance #crossdressing #embarrassed #dress #makeup
Several months ago I met this guy online. We are both males, both married and in our late 40's. He put feelers out there as a feminine guy, wanted someone to meet while crossdressed and he wanted to be sub to a dom man. I'd not had any strange pussy or ass in over 20 years but was interested. We talked exchanged pictures and he started showing me pictures of his fat wife with huge titties and ass. He would even write my name on her while she was nude and take pictures to send me. I had some old pics of my wife and showed them to him.
We met, and started a fem/masculine get together in which he would dress and I would fuck him and dom him. He wouldn't suck cock though. I finally made him do it and he got mad and I finally got him back to meeting me. He had been fucked by 4 guys before me, I'd parade him around and call him slut, cunt, and other names. I would even open the drapes in the hotel/motel rooms so that people would see this chubby older woman getting banged in her butt through the window. They didn't know I was fucking a guys ass. I always started the session by making him stand up and stick my finger up his butt and make him walk around the suite, opening drapes, windows anything I wanted. He got really sub and I even more dom and I would make him do things to his wife, and take pictures to send me. She dommed him in real life (not sex life) even making him wear cotton panties all the time usually in pink, pastels, and white. So he wouldn't mess them up she made him wear a panty liner or a full pad, just as she did everyday. Sometimes she would make him wear a bra as he had cubby manboobs. Even when they first started fucking she refused to let him stick his cock in her mouth, or in her ass. So I told him he should take his wife and force the bitch to take cum up her ass or mouth. His cock had gotten to where he could barely get it up (usually with injections) so I wrote a story about her being passed out and my fucking her.
He started experimenting with her drinking and slipping in a sleeping pill. She would pass out and he took pics of him dildoing her cunt and sticking his limp cock on her lips. At his suggestion I waited till I got word from him that she was passed out and went to his house. I played with her for a while, ate her pussy out, let him play with my nipples, then I laid on top of her and she automatically spread her legs. Instead of fucking her then I just put my cock into her sopping pussy and got it really wet, then laid him down in his girly clothes next to his wife and fucked him right next to her, in the bed the two of them shared.
After that I made him do some kinky shit, and got my cock hard again, then fucked his wife while he placed my cock at her entrance. I shot a load up her slit all the while sucking, mashing and bruising her tits. I kissed hickies on her neck, and stuck the business end of a wine bottle up her loose cunt after I was done. I made him make me dinner, while dressed in his nightie with stockings and heels. Then told him it was time her virgin asshole got fucked by a real man. We went up to the bedroom and rolled her fat ass over, I made him grease her up with some lube she had and I got on top of her while she was lying face down on the bed. I put my cock into her, and reminded him that this was the position in which I first fucked him. After having shot two loads already, it took me about 45 minutes to cum up her virgin ass. It was certainly tight, I think she was indeed a virgin, but after a 45 minute reaming with a pretty thick 7 inch cock, and her being passed out, it was gaping open bigger than a quarter.
He started to panic wondering how he was going to explain the cum in her cunt and ass. I didn't give a shit and instead jacked him off all over her face and tits. I then told him that her cunt was way too loose for her to only be fucked by his scrawny little cock. She was having an affair. I then told him the best way for him to not be accused of fucking her while she was asleep would be to suck all my cum from her cunt and her ass, and lick his off her face and tits. Then I left. I don't know what he did, but it worked out.
I fucked her about 12 times that way, and finally he told her that he liked being fucked and dressing up and she liked the idea of him being a "woman" too. So he had permission to get dressed and fucked in front of her. I went and fucked him several times, then going off with her to the store, or out to eat (using his credit card each time) then I'd go back and get off again. She made him start sucking my cock to orgasm many times, and eventually she let me fuck her in front of him. She took my cock up her cunt, her mouth, her ass, she even did ass2mouth in front of her husband. I even made him clean my shitty cock with his mouth after it was in his wifes ass.
It's a very rewarding relationship, but we still like to get her drunk and passed out so I can abuse her cunt and ass and bruise those big tits of hers. She just laughs about it now.
I love shopping for 2nd hand dresses especially vintage modest ones. Crossdressing in a dress with very naughty underwear or none at all is amazing. I love thinking about the women who owned the dress first and wonder if they wore the dress with out panties too and if they enjoyed being sexy in it too. I love contacting the and telling them how much I love the dress. It’s fun to make a story of me wearing their dress to a Burlesque show and stripping full nude on state. Many women have loved when they hear of me stripping in their old dress.
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