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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.
Recently made an onlyfans so I can descretly post my crossdressing photos. I love wearing cute panties.
So, I'm a 13 year old (straight) male and I like to cross-dress. Today, I went in to my mom's room and cross-dressed in her pantyhose, panties, bra, tank top, skirt, shirt. It made me feel so, so sexy and powerful. I love it. I also secretly use her dildos while she's at work, and I love the feeling it inside of me, it make me grin silently with happiness when that fake orgasmic penis vibrates in my anus. In addition, I have sexual fantasies about my 9 year old (female) neighbor and try on her panties and bras when she's not there. I also have sexual fantasies with my crush, who has a nice tight body and big boobs. I want to one day be inside of her body and have amazing shower sex with her.
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 like to crossdress very much and wish to have sex with males and have fun like a woman.
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 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 about 13 I sneaked into my younger sister's room and looked through her wardrobe. I found this blouse that I didn't remember ever seeing her wear, it was a pink satin slip on with a round peter pan collar placket and short frilly sleeves. It was so ultra girly that she'd probably never be seen dead in it. I'm not sure why but I sort of dared myself to put it on even though it was far too small. I had to put my arms really close together inside it and put my hands into the arm holes. Gradually I pulled it down until finally I had it on. Then I did up the buttons one by one, right up to the top. I couldn't believe how sissy I looked in the mirror, or how hard my cock was getting. Looking through her drawer, I found a pair of short pink nylon pyjama panties with flowers on them. Trembling, I put them on over my hard cock. The feel of them hugging my ass was amazing. Finally I put a pink skirt on to complete the outfit. Seeing myself dressed as a little girl in the mirror was too much, I masturbated like crazy and came half way across the room.
I admit that i enjoy wearing women's lingerie and clothing,call me what you want but until you have dressed up in sexy lingerie and clothing then don't judge people,i wear lingerie under my work clothing. Panties bras suspenders stockings and when I get home i get rid of the male clothing and slip into something lacey silky smooth and sexy
I 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
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 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.
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.
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've always had a panty fetish but last year I developed a new one. My sister was getting married and I found her wedding dress and lingerie at our parent's house. A month later I was at my sister's house babysitting and after the kids were put to bed I started searching and found her wedding dress hanging in the closet. I remembered it being so soft and decided.
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 am a sissy male and enjoy it immensely. I dream of finding a tall dark and handsome Man and he loves me for the sissy I am. He asks me to marry him and I say YES. I am his wife and lay curled up next to my Man every night playing with his Big Man Cock.. I m his wife and take care of him doing what I wife needs to do for her man. He treats me like the sissy cock slut I am and keeps me dressed like a whore. This is the life I want to live.
Sissy Boy C.
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 was so horny yesterday and hadn't had sex in a long time. I found a twink online, went by his apartment and was fully intending to fuck him with a rubber on, but instead ended up with my dick in his mouth, then bending him over and giving his asshole a creampie. As I pulled out, it was leaking out of him, I'm normally not a big cummer but this was probably the biggest load I've ever shot. I hurried up and wanted to leave, he talked me into staying for a bit, I got a beer and we talked while he had some straight porn on the TV in his bedroom. His ass was pointed up and his hole was gaping open with my cum leaking out. I fucked him again, he tried to jack off his little dick but I wouldn't let him. I kept pulling his hand away, rubbed his pubic bush, and his nipples like I would a girl if I was fucking her in the ass.
I hate the fact that I did it to another guy. He was dressed in stockings, garter, a camisole which was like a small bra up top, he had very long sexy hair too and was in full make up. But still I fucked a guy and let him suck my dick. I shouldn't have done it, but I needed to come so badly.
#mm #crossdress #homo
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
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