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Tranny Stories

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
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
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
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
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
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
The Dark Backwards Ends !
These three ladies kind of cornered me. I'm looking down at a semi erect cock dangling from a miniskirt. The transsexual saw my reaction to her beige colored dick and asked " Do you want to taste it ? " Just as I was about to answer, a sharp knock at the bathroom door and a shrill voice followed " No soliciting ! Take that shit outside !" The ladies quickly turned and made some quick tucks and adjustments and headed for the door. The prettiest of the trio tuned to me and said "Meet us outside." I nodded in agreement and waited a couple of minutes before exist... Read full Story
How Nina's fuckhole was broken in.
I wrote this story a while ago and saved it. It isnt tranny related at all, it is just a short story about when i lost my anal virginity. If it isnt very relevant to this site, tell me, and ill remove it. It is entitled 'Giving my anal cherry away'. I am no stranger to gay sex. I have sucked a hell of a lot of cocks. Saunas,dogging spots, toilet gloryholes, you name it. But I have always been scared of being fucked for the first time. Scared but intrigued.. I remember being fingered properly for the first time and it hurt. Then once at the cruising spot I go to in the forest, a nice old ma... Read full Story
Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now, I know what you're thinking. You're thinking that I'm just some gay guy that doesn't want to come out of the closet and is overcompensating. I honestly don't care what you call me. Up until freshman year, I considered myself one hundred percent straight. However, I quickly... Read full Story
When the Boss found out
Id been working in a new office job for a few months, keeping my secret life just that from the others who worked there. Before going out one night to a cd and gay bar in the city I was working late, knowing I wouldn't have the time to be back home, dressed and back into the city I decided to take everything to work, knowing I would be the last one there. As the others left for the night & my shift finished being the only one there I slipped off to the bathroom to transform into my sissy side. Taking the suit off and changing into my femme clothes, this time a little pink l... Read full Story
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