Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

The New Lodger Ch. 02

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

For some weeks Marc and me constantly headed up the town on the pull for guys mostly but to my surprise Marc had been interested in my Trans partner and how we met and of course my other Trans friends that were always out and about in the pubs and clubs of our home town. It wasn't until late one night after a drinking session with friends and no sign of a s...

The Ballad of Barry

by AngelaK on Sep 16, 2017
Transsexuals & Crossdressers

Part 1 - The young man Barry was in his early fifties. He stood about 6ft-1, and weighed nearly 300 pounds. He had brown hair going to gray, and green eyes. In his youth, he'd been considered handsome. Barry was also very lonely. He was struggling to cope after the loss of his wife nearly five years ago. His wife of 25 years was a companion he sorely misse...

A College Sissy Ch. 03

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

There was the time I was playing hide and seek at my friend's house. I was hiding. I ran upstairs, looking for some place to sneak into so I wouldn't be found. I felt my time slipping, but before it was too late, my friend's sister caught onto the game we were playing and waved me into her room. Her name was Stephanie. I was a shy kid, and my face turned r...

Biker Bitch Ch. 02

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter Two: Caught With Consequences Cameron Rivers' first memory of feeling different to everyone else was when he was eight years old. The other boys liked to play with bikes and toy trucks and toy cars but he much preferred his younger sister's Barbie. But even then he was smart enough not to say so. He used the excuse that he had to play with her becau...

Dream Shapes Ch. 01

by Selbryth on Dec 24, 2019
Sci-Fi & Fantasy

It was a dream, or at least I think it was. For four nights in a row, about two months ago, I dreamt that I was abducted by aliens - you know, the ones you always see drawings and illustrations of in those shows about alien abductions. But for me it was a little different. The aliens were tall, almost like the elves you see in the LOTR movies; tall and re...

Recruiting of a Sissy Maid Ch. 06

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Six: Pornography Anyone? Master Reggie knocks at Chantel's room door. Chantel replies, "Come in." Reggie comes in and says, "You packed and ready to go Chantel?" Chantel says, "Yes Master Reggie. I have a suitcase packed with outfits for the movie and a change of clothes besides what I am wearing." Chantel wears a pink t-shirt, black skinny jeans...

Hot Massage

by william125 on Sep 26, 2017
Transsexual

It's been a busy day at the spa. You decided to stay on working at the spa in your university town over the summer break rather than move back in with your parents. The spa offered an excellent training program for new starters and you found you were a natural. You quickly went from collecting used towels to massaging regular clients. As you wash the oil fro...

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A Tranny in Training

by dirtyjoe69 on Sep 15, 2017
Transsexuals & Crossdressers

I was always considered a pretty boy growing up and had a sense of confusion inside me. I knew I was gay from an early age but it wasn't just my sexual preference that was upsetting it was the fact I hated everything about being a boy. I didn't like the clothes or how they felt on me and I really hated boy things. All my life I would sneak into my mother's...

The Third Clearwater

by Damos on Jan 5, 2019
Fantasy

The Arrival It was a rainy day in Forks and looking out the window was met by Sue, my Aunt staring at me through her mirror at me, "It's Okay Damian, Charlie will take care of it all!" "I just can't believe she is gone! it was only yesterday when I was sat there watching the game with her and now she is gone!" she nodded before smiling sp...

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She Thong

by mrstanley on Sep 16, 2017
Transsexuals & Crossdressers

Her name was Cindy and she had been born a male. Cindy was a beautiful woman is every way except one. She didn't like the term tranny and preferred being referred to as a shemale. She was truly happy living as a woman. She began taking light doses of hormones at 19 she had stopped hormones because she had difficulty maintaining a full erection. Cindy was bru...