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I attended a military style boarding school from the seventh grade thru graduation. The junior classmen were enjoyed by senior classmen. By the time I was far enough along to have my own junior classman I as solidly a sissy with a well developed desire to please. Finding a well developed junior top was difficult but not impossible. My junior was nicknamed Gato, a native of Colombia. In no time he had me making his bed, polishing his boots, sucking his cock and bending over to tie my shoes.
As a full grown adult I recognize that a bottom is born a bottom, and a top is born a top. Thank God I was born a bottom.
I have cross dressed since the age of ten. I still do in privet, now days. I have always wished I had transitioned to female when I got out of high school or by the age of thirty. Then find a hansom Man with a large Cock to marry me for life. I would be his wife and service his every need. CK
I look back at the pictures and feel like such a sissy. My totally hot young neighbor girl stopped by a few times. She got naked in my pool, she let me eat her pussy but wouldn't let me fuck her unless I wore her panties. I gladly did and she has pics of it but I never got to fuck her. This happened more then once too.
I really want to wear girls panties but im a boy they make me so horny i dream every night about being a girl that can wear gorgeous lingerie everyday
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.
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.
I wish my best friend impregnates my wife. I would love to raise the child as my own. I just want my child to have better genes than mine. My friend is triple the size of me, you know i dont deserve to have a child.
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 female friend of mine always asks me to give her money and I usually do. She wanted twenty bucks the other day and I said she had to show me her tits. She laughed and said I wasn't going to see her tits for twenty bucks. She said to give her the twenty bucks and take all of my clothes off in front of her. That's what I did. Not sure how that got turned around but it was fun.
#sissy #exhibitionist #voyeur #nude
I am a 24 year old male and I absolutely love to wear women's clothing, lingerie, panties,bras, skirts, etc. I love to wear Hello Kitty, Disney Princess and Victoria's Secret Pink panties. I am completely obsessed with wearing girl's clothing and have done it since I was 16. I love women's clothing and I wish I was born a girl. I am jealous of women for getting to wear those clothes all the time.
I have been dating a girl for 5 years total and there was a break in the middle, in the break I found a taking to bbc porn, the more I watched the more I craved I got a small dildo in that time, about 6 inches and I quickly loved it, after I bought it and used it often I got back together with the same girl a few months later, but I never told her about my exploration, since we’ve been back together I’ve gotten 4 more dildos all black of course. Smallest being 8 inches and Biggest in size being 12 inches and as thick as a beer can, I fuck my self daily dreaming of big black cocks absolutely rearranging my guts while I’m sucking a load down my throat from another. She still doesn’t know and if she finds out I’m curious if she’s going to leave me or fuck me harder than anything on this planet, hopefully it’s option two :)
So I'm straight but I enjoy anal play...so one day I found an object (dildo like) and whilst showering fucked my ass.
It was the best orgasm I ever had, when it goes to the second sphincter the feeling is amazing...
I got married and found out I married a sissy male, so I decided he will become my sissy girlfriend. Without his knowledge I have been feeding him female hormones and getting him to dress like me in the bedroom.
i am a closeted faggot and i love looking like a female, with lingerie, skirt, jewelery, makeup, high heels shoes and wig.and i love fat over 50s men to fuck me and take pictures, telling me they will show to my family.
my wife dresses me in sexy lingerie when ever she wants me to go down on her and I love it. she has bought me the sexiest babydoll nighties over the years and all she has to do is lay one out for me and I am between her legs. She wont let me put it on, she dresses me, playing with my nipples and growing cock the whole time. I cant touch myself until after she has cum at least three times
I get high on meth every day and when I get high, I rage with the desire to dress up as a woman (I'm a guy) and have sex with straight men who love to abuse sissies. I like being bullied, mistreated, and fucked, anything the guy wants to do I'll let him, the more humiliating the better.
#meth #sissy #cumdump #humiliation
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.
I wore a sissy baby dress and red very shiny and bright panties when I answered the door when my wife's boyfriend came to pick her up for their date. My wife didn't know I was going to do that. When she stood at the top of the stairs she was just wide eyed staring at me. Her boyfriend kept his cool and was talking to me on our couch. My wife came down the stairs and started appoligizing to her boyfriend about me but he stopped her and said he understands why she and I both needed a real man in this household. I said if he would like to move in our home he would be considered the only man in the house. He said he would like to talk with my wife about it and let us know when he made a decision. Needless to say he moved in about two days later. I and my wife have worn nothing but dresses ever since. He moved in to their bedroom . I have moved in one of the other bedroom s on the first floor. My wife tried to embarrass me once after that by inviting several of my friends over for a party one night what she learned was all my friends thought I was a woman they always saw me in nothing but a dress. None of them had any idea that I was married. And certainly not to another woman she was glad she didn't tell them she was my wife.
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