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Back when i was 14 i would crossdress for older men through kik. I once found my teacher on there and i never told him anything but he was my biggest fan.
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
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 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 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 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'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 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.
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 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 have a long straight hair fetish. Whenever I encounter a younger woman (the younger the better with long straight hair, I get aroused sexually. This usually ends in my going home and masturbating while thinking of the girl.
Over the years of having this fetish, I have attempted to satisfy it by buying several wigs of various styles. At first, I only played with them but this resulted in me trying them on and masturbating in front of a mirror. Eventually it led to cross dressing but only as a younger woman. I would purchase younger clothes and mimic the young girls I often saw in public places.
Now, I am taking this CD thing to the next level and going out to CD friendly public bars. I dress as a young woman in very conservative clothes and try to fit in. But in the end, it is all about the hair. Long straight hair falling around my face and down my back. Bangs are a plus with me and if I can style them with a deep sidepart, all the better. I cant get enough of this fetish and often wonder what will become of it. The only positive thing is that I am not hurting anyone and am keeping it totally to myself. My biggest worry is getting caught.
I guess I asked for it sort of. She ordered me to make a video last night. I was told to set up my video camera in her room. Go in and strip right in front of the camera and start jerking off. Then pretend to steal the panties that she just took off. I had to put them on and jerk off. Just before I blew my load she came in a "caught" me. Now she's telling everyone she actually caught me in her room and is GIVING copies to our friends.
I have been married a long time, and when my Wife goes out, I dress up in her lingerie and clothing and go out to local adult video shop to have sex with other men. Most of the time I just give blowjobs, however on a few occasions I let them have intercourse with me and not use a condom. I enjoy being seen after having been used that way, and have their cum running out of me into my Wife's panties.
#gay #homosexual #crossdress #suck #swallow #fucked
I 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'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?
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.
Well a lot of my ‘sins’ began back when I was 14, I am 16 now. Then I would post a lot of pictures of me online on reddit claiming to be 18. I loved the attention from the guys and girls I got because I didn’t feel comfortable with myself and they actually liked me for me. They loved my body and made me confident in myself. I loved wearing girls clothing and began stealing cloths from my sister and aunt, trying on anything that I liked. I would show pictures of me masturbating, or ones of me twerking, trying new things, everything, I loved being a little slut like that. But eventually I calmed down on the whole posting thing as life took its toll on me and I couldn’t keep up with it. But that didn’t me from getting kinkier. I went deeper and deeper into the web, finding all the craziest of shit.
But one thing I did that I really loved was when my aunt and uncle were out of town, they had my house and dog sitting so I had free rain of their house. I went into their room and began looking around for toys, but wasn’t able to find anything. I did find some dirty underwear I played with and eventually came in. But also I went through their closet and tried on a bunch of her cloths as I loved them. At one point I was dressed in a pair of sexy thong panties, a lacy matching bra, silk teddy and silk robe. I’m not crazy chubby, but my chest area kind of looks like I have boobs even though I’m a boy so they fit her cloths perfectly. I took one of their dog collars and put it around my throat and painted my lips and put lipstick on. I jerked off everywhere and came in a bottle of her lotion. I then also used random things I found around the house as dildos as I’m pretty brave. But also, I wanted to try something out, so I took one of the male dogs to the bathroom and I began jerking him off. I then also began to suck him off, but when it tried to get him to fuck me he was too small and didn’t seem interested. That’s definitely a dream of mine, to be fucked by a big hung dog…
But that was my confession, hope I’m not too much of a weirdo for here…thanks for reading if you’ve gotten this far
#femboy #confession #young #teen #beast #posting #crossdressing #incest #sneaky
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 love shopping for 2nd hand dresses especially vintage modest ones. Crossdressing in a dress with very naughty underwear or none at all is amazing. I love thinking about the women who owned the dress first and wonder if they wore the dress with out panties too and if they enjoyed being sexy in it too. I love contacting the and telling them how much I love the dress. It’s fun to make a story of me wearing their dress to a Burlesque show and stripping full nude on state. Many women have loved when they hear of me stripping in their old dress.
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