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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
Like Confession #1445, i, too, have a fetish for long, straight, hair. Our confessions aren't just similar-they are copies.
When I was a young teen, my older sister (8 yrs older) briefly moved back home. When no one was home, I used to crossdress in my Mom's clothes. With my sister home, I started sneaking into her room and started wearing her more modern, stylish clothes. Think late 1960's-mini-skirts, tube tops, hoop earrings, etc.. She was a brunette and had two hairpieces. One was a beautiful, full, chocolate brown, shoulder length, page-boy wig with full bangs. The other was a nice fall, about 18", curled upward ala MTM. During the summer, when school was out, I was allowed to be home alone, sorta like latch key. Sometimes I would take a day home alone and dress up in make up, padded bras, panties, nylons, get into my my sister's clothes and her wig and then masturbate. My favorite was to dress up with the full wig and then jack off with the fall. The feel of the hair on my dick was/is just indescribable both physically and sexually. Intoxicating. And so it is to this day. I.m in my early sixties and still have a long, straight hair fetish. By happy (or perhaps, unhappy) coincidence to my hair fetish, during my life I was married to a certain woman for 25 years. It was dysfunctional the whole time in one way or another and we ultimately had no intercourse during the last ten years until divorce. That was 8 years ago. BUT... in that last 10 year time period, my sexual needs were meet EXCLUSIVELY with hairjobs. Ok, maybe a blow job or two. Anything but intercourse. She was glad to be let off the hook and I was now able to tune into a fetish I'd only dreamed about and so the bargain was struck. It was a match made in heaven (sort of). and lasted for about 8 or 9 years. I could and did get them whenever I wanted. And Sunday mornings were set in stone. Otherwise, I could either jack myself off with my wife accommodating me in various positions to put her hair on me or she would jack me off with her hair while I kicked back. .I am single now and retired and have a few "girls" who service me regularly. I have a small walk-closet with some wig heads positioned. I like to get stoned (I live in a cannabis legal state) and do some dressing up and retire to my fun room. I put on my favorite wig for the day and then jack off with my next favorite hairpiece.
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 am 29, male, married. I'm 5ft. 9in tall, weigh 145lbs, with a 30" waist. Though married I and my wife have both had homosexual experiences in our pasts. I just finished the first week of a three week trip out of town without my wife. I only have about 5 hours a day of work the rest of the time I'm free in a temporary corporate apartment.
I don't know why, but I went to a gay bar and let two guys pick me up and fuck me. First in the parking lot bent over the trunk of the car, then they came back here and fucked me several times. I guess I got a renewed feel for having sex with men, and liked it. The next day I went out and bought some girl underwear, very sexy stuff, along with some lingerie and nighties. I started wearing the stockings/garter, panties and even a bra to the bar and felt so feminine amongst all the hunks there. I let a man take me back to my place and he was very gentle and his huge cock got so hard when he saw me in my undies. I slid my panties down and then lubed up, and laid on the bed. After sucking him for a while he entered me and we both enjoyed about 20 minutes of fucking. After that I went to the toilet to clean up, put on some makeup and sexy lingerie and went back out to the living room where he was watching TV. I sat next to him and he began kissing me, moving my bra to suck my erect nipples. He actually reached down and got my small cock hard and sat astride my lap and guided it into him. I came like never before then he got up, picked me up in his arms and took me to the bedroom where we went for round two. I have been dressing for the whole week, and even bought a couple of mini skirts, and blouses, and hit the bar. I'm really enjoying crossdressing and actual like getting fucked way more than I used to. I know it's dangerous, but I'm allowing myself to become a cum dump for men. I feel like a real woman, letting men use my body for their pleasure. Right now, I am going out to a clothing store, dressed in thigh high stockings, panties, bra, a black mini skirt and white blouse, fully made up, and hair fluffed, blown out and ready. My date from last night is taking me shopping, then to lunch. I guess I'll have to repay him somehow after we get back before he goes back to his wife.
#bi #crossdress #gay
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
I am a married man in my 50s and have been crossdressing since my teens in secret. Last year my wife caught me and ended our sex, exiling me to the guest bedroom. Late at night now I surf porn and craigslist. I recently hooked up with another married guy in his 50s, dressed in a slip and bra and sucked his cock. It was my first time but OMG I loved it. When he held my head and shot his load on my mouth I got so excited I leaked a little cum. He just texted me to come by and wants me to wear his wife's clothes. I am so excited.
I have to say that I have been a long time cross dresser since age ten or so. My wife of ten years does not know. I also enjoy looking at sissies with erections. I become very aroused with both of these obsessions I have.
I am a long time crossdresser who now fantasizes about having sex with an older man. I would love to dress up in a slutty skirt and top along with a sexy bra, panties, stockings and high heels. I would be completely made up as a woman and try to be as sexy as I could. I would then like to meet an older married man in his sixties who would take me home to his place. Perhaps his wife was on a trip and he had the place to himself. We could have a drink and then and then engage in some long lasting foreplay so he would get really turned on. I would let him take me to bed and I would suck his cock for a little while until I got on my back and opened my legs to fuck. It would feel wonderful to feel his cock in me and have the weight of him on me. I would wrap my legs around him and wiggle my ass to the rythym of his cock going in and out. When he came it would be an explosion of hot cum in me and would feel so good. If his wife was going to be gone for a while I would try to stay there and fuck him as much as I could. It would be our little secret and his wife would never know about the hot fucking that took place in her bed.
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 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 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
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'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 like to crossdress very much and wish to have sex with males and have fun like a woman.
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!
I'm a straight guy who sometimes likes girly stuff: I'm completely shaved on all my body, my toenails are painted and I like certain articles of women's clothes. I usually mix and match male/female clothing. For example, right now I'm wearing jeans, a hoodie, panty hose and panties.
I also love having sex with prostitutes, especially when I wear a skirt or a dress to the whore house. For some reason or another, that's my sex fetish. I live in a country where there is no stigma concerning prostitution, so I'm at the whorehouse twice a week on average.
I know that no woman in her right mind would ever understand this fetish, so I've given up the idea of ever being in a relationship with any woman who isn't a sex worker.
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 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 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'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.
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