Tranny Surprise Stories

136,341 results
Orientation
Length
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Infinite Scroll

There's Something about Sarah Ch. 06

by MicheleNylons on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Six - Tina Tina drove me back to the Holiday Inn and we kicked off our shoes, put up our feet on my bed and lit cigarettes. I had poured us both a tumbler of Jack. We sat upright with our backs against the cheap headboard. "That wasn't so bad," Tina said. "Sloane looks fat," I replied. "Ouch! Bitch!" Tina laughed. "'You're the celebrity around...

My Babysitter Ch. 03

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a wo...

After Church

by alien_freak_nugget on Jan 15, 2019
Transgender & Crossdressers

I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they weren't very interested in me. I guess. It didn't seem like anyo...

Tranny G's all Tranny Gang Bang

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

Chris had finally returned after a year overseas. During his leave he flew out to Phoenix and we would spend a few days in Las Vegas. We drove four hours and checked into the hotel. A year apart and we ripped our clothes off and fucked hard. We took a short nap and went for an early dinner. I told Chris I was taking Tranny G out for the evening, a surprise t...

A Black Businessman in Ottawa

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

What's up everybody? My name is Alain Joseph, and my friends call me A.J. I was born on January 30, 1987 in the town of Cap-Haitien, in the north coast of the island of Haiti, and my family moved to the City of Montreal, province of Quebec, in the summer of 1997. I recently graduated from McGill University with a Master's degree in Business Administration an...

Six Hours of Heaven

by diablofire on Sep 15, 2017
Transsexuals & Crossdressers

Authors Notes: This is the story of my first visit to an anything goes swingers club in Las Vegas. The night of the story I was one of the first arrive and one of the last to leave. ***** I finally sat down with my wife yesterday afternoon and had a talk with her about my desires to take my sexual desires to the next level and I was surprised what her resp...

A Very Special Club

by LorenzoAbajos on Aug 31, 2017
Group Sex

We met at a different house every time the club met. We might meet only once a month with all the members, but some members would meet in smaller groups more often if they cared too. We were young and old, male and female, beautiful and average, gay and straight, and we all loved masturbating. It had all began slowly, of course. I was the instigator. I love...

The Virgin Tranny & the Bride Ch. 03A

by yano on Sep 25, 2017
Transsexuals & Crossdressers

I’m still awaiting the next instalment from Roberta which seems to be as eagerly awaited by many of you too. May I thank you all for your interest, and also for your votes. In the meantime I have decided to write, in her absence, what I think Roberta, Margaret and John did. Here is chapter 3A of the The Virgin Tranny and the Bride. Hope you like it. By...

Recruiting of a Sissy Maid Ch. 13

by Sissy_Chantel on Nov 28, 2017
Transsexuals & Crossdressers

Chapter Thirteen: A Business Trip to an Adult Movie Convention, Carl and Chantel Consummate a True Loving Relationship. Carl says, "Chantel make sure you pack well but not slutty ok. I will have you travel with me as my girl friend and secretary. Dress nice but casual for our flight but of course still be an eye catcher ok?" Chantel replies, "Ok hun, I fig...

A Love of My Very Own

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

In the eyes of the world, I am many things. She-male. Tranny. Chick with dick. Those are the names they've got for me. What do I call myself? I call myself Angela Shay. Anyone looking at me would see a five-foot-nine, curvy Black woman in her mid-thirties with a nice rack, wide hips and a big round ass. I hate the terms she-male, tranny and chick with dick,...