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Tranny Stories

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Caught Wearing A Bra By Mother-In-Law
I have been wearing women's clothes since I was 15, having acquired a bra from the girls locker room,which I loved to wrap around my cock then wanking, shooting into the cup,and since then I progressed to owning my own selections of lingerie,skirts,dresses etc. so today I have a fair few items from bras to dresses to a wig & make-up. Recently my wife & I moved in with Stella,my mother-in-law after Harry,(my father-in-law),passed away so we could care for her & make sure she took her meds correctly. One side effect of the drugs she took was insomnia which meant I had to be very... Read full Story
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Humiliation & full outing
I'd been meeting 2 older men regularly for a few months when we started to talk of more 'humiliating use of me'. They soon arranged to meet me in a hotel in the next city across from where I was living at the time & I made my way across one night to meet up with them. When I arrived they where soon desperate for me to get dressed so they could start. As i got out of the bathroom transformed they where both quickly all over me, fingers searching out every hole I had, spanking and grabbing my ass. I was soon pushed to my knees and started alternating between coc... Read full Story
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Shemale Ride Along Part 2
Note: This is a sequel to my previous story, "Riding in Cars with Shemales." If you would like some back story into how Terra and Matt met, please read it. If not, you can probably still enjoy this one by itself. * It was a wonderful day in May. The sun was shining. The sky was clear. Birds were chirping everywhere and everyone was spending their Friday after class outside. That is, except for me and my shemale friend Terra. I decided to spend my afternoon inside my dorm room, and Terra and her big dick decided to spend the afternoon inside my ass. It was only about four o&... Read full Story
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My life as a crossdresser (chapter 1)
Hi all you wonderful people this is the story of the start of my crossdressing adventure, this is chapter one of many It all started 35 odd years ago when I had my first bi experience my father passed away when I was quite young and my mum used to walk about at home in her undies, always stockings suspenders and bra and I loved the look of the undies, I had seen plenty of porn pics at work and most of the women were wearing stockings, I decided to try one of my mums suspender belts and a pair of stockings as I put the stockings on my cock got so hard it hurt, I stood looking in the mirror I pu... Read full Story
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Sissy for the boss
Id started a new job & kept my sissy life quiet there, there was a night out arranged, but I had other plans already, a sissy night out with friends, so made the excuses needed & said I would be the one to stay later so they could leave early, which also let me get dressed there alone to save so much time rather than going home to do it all. After they left & my shift finished I went off to the bathrooms & turned sissy, a little pink lace dress, thong and heels, with a blonde wig & full make up. I went to take my 'normal' clothes back to leave at my desk whe... Read full Story
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How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor button front jeans and high heels. When she wasn't around I would try them on and get very excited. One time my sister walked in on me and I had on her sailor jeans and hi heels and i was curling my hair. I got in big trouble from my mom. When my brother heard about it. I guess it kind of made h... Read full Story
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Gloryhole
It wasnt long after arriving before a cock slide through the glory hole for me to suck on, and what a cock, big thick & so suckable. I didnt need asking and was soon parting my lips and taking as much as i could in my mouth. The moans from the next cubicle seemed to indicate that it was more than welcome. He was soon calling me as many names as you can think as I sucked away at this hot cock. After blowing his cock a little longer, he pulled it away & I heard the cubicle door open & a bang on mine. I undid the latch so the door opened and the guy whose cock id been sucking ... Read full Story
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Short and Sweet First TS Encounter
My 1st TS encounter took place back in the early 80s. When people still picked up Hitchhikers and Transgenders were not as out in the open as they are now. It wasn’t a grand adventure or planned out and executed with precision. It was a complete accident and it could have gone differently if I weren’t such a Pervert and wanting all kinds of sexual experiences. I finished a job late on Friday and was driving home. A few miles from home I see a good looking woman hitchhiking . She was going the wrong way but I figured I might get a blow job out of it if nothing else, so I swung around an... Read full Story
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Lay Report #4
Real TS Encounters Lay Report #4 6/27/2016 Hey there, Welcome to “Lay Report #4” So this is yet another Craigslist hookup. I would love to make my next report show a different way to meet a girl other than Craigslist. It just so happens that my last four hookups have been from Craigslist. It’s unusual but possible. If you’re familiar with my website then you know most of my hookups come from TS Dating. So anyway, it was about 11 pm on a Sunday night. I went on Craigslist, replied to a few ads. I saw an ad of this one girl who I had spoken to a few times already. She was very ... Read full Story
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Jasons dream of becoming a woman comes true
Once upon a time, there was a boy called Jason. Bored with his every day life, he found himself drinking in the pub most nights with his friends. He would come home and sit down in front of the television and flick through the channels. Satellite TV was ok, showing 10 minutes of free view here and there but it wasn’t quite what Jason liked. He went to the fridge and cracked open another bottle of beer and returned to the TV. He flicked the DVD player on and up came one of his favourite TS films. So bored with the life he led and wishing for more excitement, his head would often work overtime... Read full Story
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