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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'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.
When I was teenager home by myself I used to put on my sisters dress and wear my mothers lipstick. Later on I worked at a library wearing panties and nail polish. Now my wife has stopped wearing bras so I want to wear them, but don’t want her to know but I’m not worried if my daughter sees me in a dress for some reason. She’s just bought some bras and I wish I could bought some too.
I admit that i enjoy wearing women's lingerie and clothing,call me what you want but until you have dressed up in sexy lingerie and clothing then don't judge people,i wear lingerie under my work clothing. Panties bras suspenders stockings and when I get home i get rid of the male clothing and slip into something lacey silky smooth and sexy
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
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 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.
Yesterday, I was shopping at JC Penny's and went into a fitting room to try on some jeans. Someone before me had left a bra hanging there.
I couldn't help myself and I put it on and wore it home. I'm a guy.
I am a thirty five year old man who by day seems like a pretty typical guy. But, I am closet gay and cross dresser. No one knows. I dress in panties, bras, stockings, high heels at home. When I dress, I become effeminate -- prancing, swishing, the whole bit like a silly little girl. I find it completely liberating and relaxing at the same time. Once a month, for fun but to keep anonymous, I get a hotel room and seek guys online. I dress up and host men -- it turns me on to host as many as I can in one night. Current record is 6. While there is no money exchange, I do feel like the scene is very much a prostitute (me, dressed like a dirty whore) and Johns. When I service them to completion (mainly blow jobs but I do enjoy penetration), they simply leave. I am usually on the floor in my panties/bra, covered in cum, but still horny for another man's penis.
I am obsessed with female clothing. Yes, I am a closet cross dresser. My girlfriend knows nothing about my cross dressing. We had an argument so I left and went into the city which is fours away. Taking one of my slutty cross dressing outfits with me. I had a room and decided to finally go out in public like the sissy slut I have always wanted to be. I went to a bar and was hit on right away. I hooked up with the guy and ended up back at his place. When he took his close off he had the biggest cock I had ever seen. I felt a strong sensation to suck it. He walked over to me and stood with his big cock inches from my face. I picked the semi erect mammoth and with out hesitation started sucking on it as if my life depended upon it.
When he had me straddle his cock so he could take my virginity. He also stroked my little sissy cock at the same time as I humped his cock. When he climaxed so did I in the most mind shattering orgasm I ever have had. I spent the night with him and found it hard to leave the next day. I want to be with him more than my girlfriend so I broke up with her. Looking forward to visiting my new lover and his wonderful cock.
I'm a crossdresser, and have been for over 20 years. A few weeks ago, I met another crossdresser and we sucked each other off, the first time I ever sucked a dick. Since then, I've sucked two more, and I want more. I love it.
I'm a 25 year old male and I once paid a girl to dress me up in her panties, bra, miniskirt, high heels, and a blonde wig and then laugh at me and taunt me. It was so humiliating but soooo hot.
I confess that I'm kinda fashion freak. The first thing I notice about another person is their style, what they wear, how they dress. I literally hate people who set no great store by dressing good.
I'm a sissy crossdresser obsessed with wearing women's lingerie and clothing. One time, I was over at my friends house who was having a small party. The girl who was throwing the party was this sexy asian girl with tan skin and beautiful body. While everyone was in the living room, I slipped away down the hallway to her room pretending to go the bathroom. I looked on the floor and found two pairs of used panties and a pair of stockings. I took them into the bathroom and I stripped down. I wore one of them, a blue hipster cotton panties and then I put the stockings over them. Then I started masturbating while I brought the other pair of used panties up to my face and started inhaling the sweet perfume of her pussy. I could hear everyone having still drinking and having fun and nobody knew what I was doing. As I was about to cum, I took the sweet smelling panties I had up to my face and brought it down and came into them. Because I made a mess, I decided to clean it up by licking my cum off her panties. Once I was done, I put my clothes back on again and put everything back where they belonged and went back to the party.
I was house watching my old aunts house for two weeks while she was on holiday. I had her whole house to myself and all her clothes to dress up in. I love getting strapped up in her corselets and barely black tights and put on one of her wigs. One morning I did this when her window cleaner came. I put on a show for the old window cleaner pretending not to see him looking in as I was pulling up my tights. He quickly moved away from the window and the next thing was I heard him coming in the room. He had his cock out and ordered me to suck it. When he realised I was a bloke he said he was going to take it out on my backside and made me bend over pulled down my tights and unhooked the corselet gusset. The thing is that when he shot his load in my bum it made me cum. We both ended up in a 69 shooting in each others mouth.
#crossdress #cum #mouth
I had been out of town for a month and getting desperate. I was in New Orleans, and walked past a tiny little bar and decided to go have a beer. As I sipped my beer I noticed a small, rather shy looking girl at a table all alone next to the dance floor. I kept watching her, she had a yellow sun dress on, and small boobs which I like, and very nice, shapely legs which I LOVE. I didn't see her butt, though all in all, she was looking pretty good. I saw some guys come out of a door at the back of the place, then a couple of what could only be crossdressers. Oh well, New Orleans, and live and let live. Then I noticed a butch patron and the bartender were a guy in drag, and a super butch lesbian. I figured it was a safe bet that the object of my immediate lust was a CD. I bought her a drink, sent it over, and then asked if I could join her and she said yes. She was definitely a He. Not being gay, but very desperate to have someone to have sex with other than my hand or a paid masseuse, and her being actually very pretty with a very feminine petite body, I started talking. She didn't want to talk much as her voice gave her away, but she was still pretty femmie sounding. After several hours, and a burger each for us, I made her stand up and start slow dancing. She was shorter than me, about 5ft. 8in, with a very thin body. I put both arms around her waist and as we danced, I went towards the corner and with her back to the corner and no one seeing, I pulled up her dress in the back and stuck my hands in her panties. She protested, and I wouldn't stop. Finally she said "Back Room" , I didn't know what that meant, but she advanced to that door at the back showing everyone my hands were on her bare ass. It was a totally dark room. "We can do whatever we want here" he/she said. So I pulled up the dress and pulled off the panties and started groping her ass. Kissing and licking, and rubbing, she asked if I wanted to do it there. I said no, I wanted her in my hotel room. Instead she said to go to her apartment which was only a block away. So I put the panties in my pocket and saw her moving what must be her cock between her legs, and we walked out, paid the tab and left, with the patrons wishing us a very sexy and good night.
At her place in subdued light I could imagine myself with a girl not a guy. I like buttfucking girls, so this should be no different. I got the dress off, kept her bra on, and with no panties saw her little cock a little bigger than my thumb, that was all. . . and it was fully hard. I pushed her down on her knees and she began sucking my cock, I told her to suck my cum so I could last longer when I fucked her. She was excellent and I was cumming in about 10 minutes. She the laid me down, got some oil and gave me a great massage for about 20 minutes ending up with her using the oil and getting my cock hard again. I pushed her on her back and got between her legs and kissing her, stuck my cock in her cumhole. It was very loose with all that oil, and I'm sure because she'd been fucked by a LOT of cocks in her time. I fucked her for about 30 minutes very rough and hard it felt like I was fucking a pussy, not at all like the girls butts I'd fucked. I rammed my cock up into this little cum bucket and flooded her with my cum. Adding to my 8inches I'm guessing I shot hard enough that it went over a foot up her poop chute. Exhausted I rolled off her and lain next to her. She moved my hand to her little cock which we called a clit and asked me to suck her. I told her I didn't suck, actually had never done it with a guy. She gave me the oil and told me to use my hand and help her out, and in her most feminine manner said "A good lover makes sure the girl cums too!". So I did. I actually gave a cock a hand job. When she was shooting I had moved my face close to watch, I did lick just a couple of drops off my hand. With that done I stuck around and fucked her ass one more time this time her on her belly and I left.
We met a few times in the next couple of weeks, and she finally got me sucking her little thumb sized clit, till she'd cum in my mouth. I don't mind so much. Last night we went out as two guys, and I fucked her all night at her place, stayed over and woke up to a smooth, girl in lingerie for my morning fuck. Then she rolled me over on my belly and got on top of me.
It's amazing what being desperate can do for what I used to think was the straightest guy on the planet.
I'm a straight guy but I have to confess that since I was 14 I took a interest in sexy lingerie and began secretly dressing in it. My wife thinks she got me into it 9yrs ago so I let her think that. So I have really been wearing women's clothing for nearly 20yrs..I feel comfatable and relax in female clothing.I wear lingerie every day under my work clothes. At home I get around wearing either a nice dress or a nice skirt and blouse
I was shopping the other day looking for some cute shoes for my new dress. I even found some shoes, brown ones with closers on the right sight. Like you can imagine those shoes were SO EXPENSIVE, I could never ever in my life afford them. I just put them on, left my old sneakers behind and walked out of the store. 2 policemen were standing in front of the building, I nicely said hello and went on.
#shopping #dress #shoes #closer #sneaker #thief #police #confess
I confess that my fetish is dressing as a sissy, I have so many outfits, wigs, breast forms, etc. I love to fish and know many places where I can fish without too many people around, but am always cautious. I love fishing in only panties and bra, so as I can get my tan lines set. Last year caught a few nice fish and poised for selfies dressed and holding fish and even put them online in a few places.
One day as I was waiting for it to get light, staying at motel along the highway, where the speed limit is reduced to 35 mph, was dressed slutty and was un-tarping boat, many truckers drove by and this sissy was in plain view for them to see. It was very exciting. I also dressed wearing a long fishnet pink dress, pink bra and pink panties with wig on, filled the truck up full of gas and drove home and on the way, stopped for an espresso, another thrill.
This sissy has been online searching for new outfits for this years journey. So looking forward to playing dressup in cabin and being displayed outside for all the truckers and fishing, looking like a sissy. Deep down, have always wished I were a female
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