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A while back, after a breakup, I had been using phone sex services regularly. I usually used Femdom providers.
One woman I called kept telling me I needed to get peach colored lipstick to give blowjobs. She figured had a slutty alter ego.
After using her regularly, I got a notification for registered mail waiting at the post office. I got the parcel and opened it up in the car. It was a pair of silky panties and a note from the provider. I called her later that day and she made me put on the panties and lipstick and promise I’d suck cock.
That started my secret fetish. I dress up in stockings, 4”heels, and lingerie and act as a cock hungry sissy slut.
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 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.
Recently made an onlyfans so I can descretly post my crossdressing photos. I love wearing cute panties.
I used to ride motorcycles alot and I always wore these tight black leather pants with boots. Usually I was out late nights barhopping. Some nights I scored pussy. Some nights I scored none. One night in particular I was out late. The time was about 4a.m. I had not gotten lucky that night. I noticed sitting at the bar was a thick redhead woman. The stool next to her was empty. I sat on that stool and continued my beer. Said hi to her and as natural began the small talk. We sat and talked a few minutes. Now I am a tall slender guy of pretty good looks. She was not bad looking at all.I guessed her to be mid to late 40s. I was late 20s. She had on a short black skirt with nice thick legs. Her makeup was impecable. She offered to buy me a beer and I accepted. As small talk continued I noticed her hand on my thigh. By this time my dick was aroused. Her hand rubbed towards the inside of my thigh and not too far from my bulge. She then proceeded to tell me she was a boy. Well now, what do ya do? Excellent tactic; look just like a woman, buy a guy a drink and then get his cock all worked up. She knew what she wanted. Now in this town it was not unusual for sissies and drag queens to frequent the bar scene. There were quite a few clubs that featured drag queen lip-syncing shows and contests. So I was not shocked. In fact I felt complimented. Well one thing led to another I wasnt getting any pussy that night but I was curious as hell. On my other side sitting was an aquaintence of mine. He leaned to me and asked what her story was. I told him she says she is a boy. He was like," Really? " Well she looks over at me and tells me is heading out. I told my buddy that I wanted to go see what this was all about.
So I left with her and followed her to where she lived. She shared a house with a few other people; one of whom I knew but he did not know I was there. W went up to her room. All feminine. Nothing boyish at all. Well I was nervous in a sense. My cock was raging hard. I had no idea what I was gonna do. She wasted no time removing her blouse and bra. She had really nice big tits. She laid on her bed leaning on her right elbow. I just paced. She told me in her raspy voice,"I wish I could get you out of those leather pants." I acted as if I did not really hear that. We exchanged more chit chat and she rubbed the bed next to her and said it again. Finally I had enough. I caved. I walked up to her bed.
"I know what you want" I said to her.
"Oh?" she says.
I proceed to unfasten my belt and unsnap my pants. I pull down on my zipper. She begins to start gazing at my crotch. Now I am no small boy. Not John Holmes but larger than average. I pushed my pants to my knees and my cock appeared.
"Ooooh! Nice." she says as I sit down next to her and lean back. My cock was stiff against my abdomen. She reached forward and wrapped her hand around it. She then began to lean her face forward as she slid the head in between her lips. She began the up and down movement that comes with a gurl sucking a big hard dick. All I know is this was THE BEST blow job I had ever received. She continuef about 10 minutes licking the head, kissing the head and running that tongue up and down the shaft while massaging my balls. I was amazed at how good she looked and how good it felt. I soon felt it coming. She sensed it as she raised up and let the cum shoot onto her face. Another shot went on my shirt. As it shoots out she again goes, "Oooooooh!" The deed was done. My first drag queen blow job. I saw her again a few weeks later. We barhopped together one night. She was my date. People in the bar scene knew I was not gay and if you were out with her you were considered lucky because you were getting sucked off. The night ended. It was morning. She drove me home. We sat in her car and talked. I couldnt stand it. I looked at her, "You wanna get me off?"
"Oh yes."
I raised my hips and lowered my pants. She sucked me to orgasm. It was exciting because of the daytime risk of being seen by neighbors. As she sucked she paused once and she looked at me and said, "You are rather large." Then continued. I soon felt it and this time she did not let it shoot out.................she swallowed.
Over the years we got together on a few occasions and it was always a great cock sucking.
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.
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.
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 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 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 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 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?
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
As a kid, I loved to call a taxi or order a pizza and tell them the address of one of my neighbours or of someone I don't like.
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.
Too often I find myself creating slideshows of women and girls wearing short skirts/dresses and masturbate to them. In real life, I'm just so turned on by short skirts that I often can't help myself whenever I see one. On top of that, if I happen to witness or find an image of a female curtsying in a skirt/dress or a panty upskirt shot, I get even more horny. And the weirdest part is that, for some silly reason, I enjoy jerking off to these pictures most when I replace the female's heads with an elephant's head. As someone who believes in Jesus Christ, I am easily able to recognize this as a habitual sin that I need to break because it often damages the way I look at the opposite sex when I see them wearing such attire.
#fetish #weirdness #pictures #masturbation #girls #skirt #dress #panties #elephant #habit #sin
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
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.
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
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