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This is another in a long of line of true stories about my crossdressing experiences. This encounter happened back in the 90s. It was Saturday night and I was on the road to the Queen Mary in Studio City. For those of you who were into the scene back then, you know what a happening place the Mary was. I was completely made up and was dressed in my favorite black, form-fitting dress. Underneath I had black panties and pantyhose. I had on great pair of 4 inch black hi heels. It was a long drive and just about 25 miles from my exit off the freeway, one of my tires had a blowout. So here I was on… Read more

This is not my story I am just reposting it. Many years ago I was a young crossdresser, in private, limited to panties and sometimes skirts I 'borrowed' from my mother. One evening I spotted some lovely panties on my neighbour's washing line. Unable to resist i sneaked over the fence and took them down, and was about to slip back to my own house when a voice stopped me, "What the hell are you doing stealing my daughter's underwear?" It was my neighbour's father, a big man, coming out of their back door. I was caught red-handed, and rooted to the spot. He told me to get inside his house quic… Read more

My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a k**, terrible at sports, threw like a girl, did very few real boy things. My best friend and I discovered porn and masturbation together. My mom didn’t watch what we were doing too closely, so we used to jerk off down my basement like all the time. We would get a Playboy or some other skin mg and just go to town. He would catch his load in his hand and dump it down the sink (what a waste) but I would usually shoot my load on the floor(anoth… Read more

Mine was when I was in the military. I was stationed overseas and went on a recreation center sponsored tour. Since I was alone recovering from a breakup with a girlfriend, I was assigned a roommate in the hotel we stayed. He was a 60 something Red Cross psychologist and I was 25. That evening in the room, I didn't really feel like talking, but he did. He offered me a glass of Johnny Walker Black and soon was paying me really nice compliments on my looks, my physique, and even my voice. I had played around with guys in school, but that went no further than jerking off together. However, I f… Read more

Nearly 4 years after my last discipline session, an old friend came back and gave my a blistering butt whipping. We'd had a scenario worked out, where when he came over, he'd go to the bathroom to pee. I watched from the outside and when he had finished, went in, grabbed his cock and offered to help. I was soon on my knees sucking his nice hard uncut cock. As per our role play, he became infuriate at such rude behavior, and took me into the living room for an OTK spanking. I thought he'd start with just a hand, but he began with a hairbrush and even though it was over my pants, it stung ser… Read more

(Part 2 / when the guests are gone) Uncle Frank and Yicky came back hand in hand and took me in the middle to go inside the house with me. Vicky felt the need to take a quick shower after the warm, tiring day. But we all three? She may have recognized in my view that Uncle Frank was not my type despite his imposing cock, because she said that Uncle Frank in their 3some adventures usually remain passive anyway or served himself as before. „Ok Deal!“ I said with a wink to Uncle Frank, whose view I… Read more

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I was around tw***e years of age when I started my real sexual experiences the first was wit my El***n year old cousin Julie her mum and my mum where always round each others houses, so I and Julie used to play up stairs we always ended up touching and playing with each other sexually we could never keep our hands off each other. Eventually this led to us fucking in her bedroom and I had my first orgasm. I was always horny and one day came across a black and white gay magazine in a field it must of been about 1972 I took it home and hid it behind my wardrobe , I used to look at it at nights i… Read more

"Hi mum," I said as I entered the living room. "Hi Steve," my mum smiled. She was sitting on the sofa in the spacious living room, which was at the back of the single-storey house she and I lived. "How was school?" she asked. "The usual, boring," I replied, dumping my schoolbag on the floor and kicking my trainers off. I didn't do too badly at school, and was an ace at sports, but like most fifteen-year-old boys I didn't exactly find it terribly thrilling. It was nice to be home. My mum, Helen, was thirty-eight-years-old, and had been divorced from my dad for a decade now. She had… Read more

Well..wow..what a feeling,looking down at my grandmother,as she swallowed my sperm! Mum removed the strapon and bid one of us to lick her to orgasm..i did and she flooded my face.Then she put it back on..and told her mum to bend over the end of the bed! She fucked her pussy,as she pushed a finger,and then a dildo up her bum! Nan was moaning and groaning..as mum fucked her silly! Then nan yelled she was cumming...and bucked against both toys.She flopped onto the bed,emotionally drained.Mum crooked her finger at me,and i went over and knelt before her.She pointed to the strapon,so i sucked my na… Read more

http://24.media.tumblr.com/858e448da6b878fd078d05e996bd6009/tumblr_mi99jmVTkc1rps7uqo8_400.g… Read more

We were in our early thirties. Jill (my wife) and I were at a small party with six other couples... the kind where you drank and talked. We all had young k**s upstairs. The times of all night parties, discos and getting crazy were over. We were adults now, upright members of the community. We had responsibilities. The women of the group knew each other through the Junior Wives Club. I was tuned out on whatever they were discussing, and checking out one of the other wives, a good-looking redhead named Debbie who was a little on the thin side but had nice tits, a great ass and a pretty face.… Read more

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