Read the best #dress confession stories
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'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 am a guy I like dressing up in woman’s clothes and like cock a lot but I am married and she knows and likes it when I dress up. And talks dirty to me until I cum.
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'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 am a secret crossdresser and when girlfriend is out I go to my garage and bring out my bag of lingerie.
I have a satin fetish and love the way it makes me feel. I get dressed up in black satin bra and thong, suspender belt, stockings and a black satin chemise. I then have webcam chats with men admitting I am gay and they tell me what a sissy I am.
Once I am finished I always feel a bit of shame and consider telling my girlfriend the truth but always end up putting the bag back and wait until the next time I am alone.
I'm a 50 year old divorced crossdresser almost my whole life. I love being feminine and am rather pretty. I love being a black c*** slut and have been since I was a teenager. My wife divorced me when she caught me in bed with two black men while dressed in her wedding gown and having sex. It's Sunday afternoon and 11 black men had sex with me this weekend and I love it the sex, shame and humiliation makes me the slut I am.
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 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.
I'm a girl and I have a fetish for dressing up like a little girl and being fucked by an older man. I've always looked younger than I actually am and I really love the cute Japanese style (like Hello kitty, Totoro, Pokemon etc). I'd love to dress in all pastel pink and put a pacifier in my mouth and be a helpless little girl being raped by an older man.
Me and my boyfriend use to roleplay this alot. I'm a little girl who is lost in the dark, creepy streets. Then a man (my boyfriend) approaches me to come to his home, where its warm and safe. So we lay in bed and my boyfriend grabs my arms, pulls my hair, spits on me, bites my neck and fucks my roughly while I try to fight back and run away.
#daddy #rape #bdsm #roleplay #dom #dominant #sub #submissive
When I was a teenager way back in the early eighties, I was taunted by some of the other boys at school for being overweight. I was a little, but in my mind at the time I was convinced it was a lot. It got to me so much that a few days before the start of the new school year I went into town with some money I'd been saving and (I can still barely believe it even after all these years) I went into a department store, went into the lingerie department and, with a bright red face, bought myself a panty girdle. Even though I dreaded the thought of wearing it, I thought a girdle would reduce my belly, tighten up my backside and get the bullies off my back. As I was excused gym class on medical grounds, there would be no problem there. And surely I'd get used to it? The assistant was initially astonished and thought I was joking at first, but when she realised I was serious, I guess she figured my money was as good as anyone else's.
So, on that first day, I headed off to school as if everything was normal, went into some derelict buildings along the way, took off my trousers, quickly tugged on my long-leg Playtex "I Can't Believe It's A Girdle!", got dressed again, and headed off to school, wide-eyed and stiff legged. My "weight loss" since the start of the summer break was noticed, but I was still bullied. And now I had to get used to wearing a tight girdle every day to maintain the weight loss illusion - I could hardly get paunchy again overnight!
Have you ever had that terrified sinking feeling in the pit of your stomach when you realise you've really screwed up? That's how I felt when it dawned on me what I'd done and that there was no going back. The whole idea was dumb from the start, had failed totally in its objective, my initial overconfident attitude about getting used to it had died the moment I'd put it on and realised as it compressed my belly, backside and thighs exactly what it was I was going to have to get used to...and now I had no way out! I felt sick as I realised I was going to have to wear a girdle - a Playtex panty girdle! - every day from now on. For no good reason. And it was all my own damn fault.
By the end of that first day of being firmly held in, I could definitely believe it was a girdle! I'd fidget around in my seat trying to get comfortable - sit forward, sit back, legs apart, legs together - but I could get no relief. It was a girdle, and it did what a girdle was supposed to do. I'd catch myself gasping as I stood up or sat down, and walking up or down stairs was...an experience. By lunchtime I felt like I just wanted to scream, but I had a long afternoon in front of me before I could take it off.
After school, I hurried back to the derelict buildings (as quickly as I could manage!) to get out of my tight new panty girdle. I was almost crying with frustration as I fumbled frantically with my belt buckle in the rush to get my trousers off and get the bloody thing off me. The relief I felt as I peeled it off was incredible. But I just had to get used to it being part of my uniform from that day on. I'm not ashamed to say that, as I tugged it on the next morning, I was actually crying. I did eventually come to terms with the situation and get used to it, but it did take a very long time.
I guess that was about the only notable thing I achieved at school, though being the only boy to have his underwear made by Playtex is something I was quite happy to keep secret!
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.
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'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.
As a 15 year old virgin male who'd been masturbating since entering puberty, I was more than a little interested in seeing a naked female or one partially dressed; to be honest any female in her underwear or less. While on holiday at my grandmothers. After spending a few hours in the local cafe, I was walking home (she lived in the country in a small group of houses) on what was a pitch black moonless night and I knew that a 50+ year old lady lived in a house nearby lived on her own and seldom had any visitors. As I walked along the very dark path, I could see the lights of her house and as I could easily hide under the cover of darkness I decided that maybe I could peek at her through her curtains. I slowly made my way into her garden and moved as quietly as I could towards the light shining out through the bottom of the window. To my great surprise and delight, the curtains were short and there was a one inch gap at the bottom where the hem was above the window sill. She was watching TV. After about 20 minutes with nothing happening, she turned off the TV and it seemed that she was going to bed. She turned off the lights in the room and a few seconds later a light came on in what was a nearby room on my right. My heart was racing and I was praying that this was her bedroom and that her curtains would have the same gap, which in fact turned out to be the case. I lowered my eyes to sill level and there she was in front of me, less than ten feet away and totally unaware of my presence. She was wearing a floral dress that unbuttoned down the front. My cock was instantly hard when she started undoing them and stepped out of the dress. She stood before me wearing a white bra, a tan coloured girdle and tan coloured stocking; she wore no panties and her hairy pussy hairs stuck out under the bottom of the girdle. With cock in hand I stroked for all I was worth as the unclipped her bra and dropped it on top of her dress. She rubbed her free tits and I could see her nipples getting hard. Next came her stockings and girdle and as she stood naked before me I came. It was clear she had no idea she was being peeped at and appreciated though once naked she left the room and I guessed that when she left the bedroom she went to the bathroom. That was over forty years ago and I have never forgotten that experience or that night. I had seen my first mature naked female in all her glory and I was horny and excited enough to want to see more.
#peeping #stripping #naked #girdle #dress #bra #stockings #unbuttoned
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'm a 65 year old bisexual male who loves to cross-dress. I've been doing this now for seven years. Wearing women's clothing just feels so good to me. When I get up in the morning, I can't wait to get my entire body shaved completely smooth, put on makeup and do my nails. Next comes my thong, corset, push-up bra, hip and butt pads, garter belt and nylons. Since I've been taking phytoestrogen supplements the whole time, my boobs have grown to fit snugly into a 42C bra. My boobs are really nice. Guys go crazy for them. I began using breast forms to augment my appearance, but I don't need them anymore to get a nice effect. I really love my boobs and fondle them as often as possible. Next comes a silky slip to drape over my torso, followed by a sexy dress with its hemline falling just above my knees. The neckline of my dress must plunge low enough to expose my cleavage. My legs have received many compliments on their shape, so I always wear a fashionable pair of heels to bolster their appearance. Earrings, necklace, bracelet and a nice wig complete the look.
My wardrobe is extensive. I have dozens of dresses, skirts, blouses, shoes. outerwear and accessories. Wigs of all shades and lengths are available to me as well. No matter how much I have, I can't resist the urge to buy more. Its definitely an obsession. When I'm fully dressed and see myself in the mirror, I nearly come to climax. OMG, how I wish I could be a woman. I'm so jealous of those who are.
Being bisexual, I crave having sex other men. As a younger man, it was relatively easy to hook up for same sex experiences. However, as I aged, it became harder to arrange such trysts. Becoming a crossdresser definitely increased my chances for success. I discovered that many men love "chicks with dicks". It opened up a whole new world for me. As soon as I began appearing in drag, I became much more desirable. My date requests grew immensely. I could pick and choose which ones to accept.
One thing I've always fantasized about was being a prostitute. How lucky women are that they can do this. I could never understand why more ladies don't participate in that occupation. I fantasized about it so much, I decided to try my luck as a crossdressing escort. Websites for escort service advertising are all over the internet. I offered my services on as many of them as I could. I really didn't know if I'd get any responses. To my surprise, the replies were overwhelming.
It was so easy to find men who wanted to have sex with me. There were several women as well. I've lost count of how many men I've sold my body to, but it has to be at least several hundred. Age range also surprised me. The youngest man I did told me he was 18, and I'm not sure if he really was . He looked no more than 16 and didn't have a car. I asked to see his ID, but he declined to show me anything. I probably shouldn't have had sex with him, but the opportunity was too irresistible. The oldest guy was in his 70's and the rest were part of every age group in between.
So far, I've made tens of thousands of dollars over the years as a part-time prostitute. I know its not the right thing to do, but I just can't stop. I've tried to quit many times. I love the work so much the idea of quitting is to depressing. I can't keep doing this forever. What am I going to do?
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 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.
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