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Tranny Stories

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Sophomore with my roommate
Sophomore year my roommate caught me dressing up in our room. I was pretty drunk and he came back from parties earlier than I thought he would. He laughed as I tried to hide, but I could see a HUGE bulge in his pants. He told me to come over to him and show off my “new look”, so I did. He sat down on his bed and pulled out one of the largest cocks I’d ever seen and started stroking it. He told me that if I wanted to look the part, I needed to act the part and to come get on my knees and suck him.. so I of course obliged! It was such a wonderful taste, and he quickly grabbed my head and face-fu... Read full Story
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Lay Report #5
Lay Report #5 8/10/2016 Craigslist Style Meet-up from TS Dating Hey, It’s been a few weeks, but finally hooked up again and therefore I am presenting to you “Lay Report #5.” So I was in Manhattan at around 12:30 am on a Wednesday. I was in my car about to go back to Long Island when I decided to go on TS Dating to see if anybody was online. There were a couple girls who I had not seen before so I decided to message the ones in NYC. I did this in case I could get a quick meet up before going back to Long Island. Typically, this is the kind of thing Craigslist is good for, how... Read full Story
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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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Uncles Ranch
Its late May and school is getting out for summer break finally next year marks the start of college but who cares about that. I’m excited to do the basic summer fun like hangout with my friends go to movies and of course get in touch with my shemale side. When I get home my parents right away tell me how my father’s friend’s wife and daughter are going to Europe for the summer and how he would love to have me up there to keep company. Now I’ve known and grown up to view him like an uncle but COME ON I don’t want to waste my whole break at some stupid ranch. So I pouted and complained making ... 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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