Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

Summer's Surprise-Encounters

by onwardbob on Sep 12, 2017
Group Sex

Bolting for the stairs, the girls reminded me of a couple of squealing kids headed for the pile of presents waiting under the tree on Christmas morning. With tantalizing images of that pair of saucy vixens sharing a shower rampaging around in my head, I shrugged and headed off for a lonely shower. Thanking whatever Gods may be for the afternoon's spectacular...

I Stop Losing

by FD45 on Sep 13, 2017
Loving Wives

This is a conclusion to a story written by TQM called "Lost Her to the Ex". It was the most popular story on another erotica site, so of course I had to read it. And I found I rather enjoyed it on some level. But it was just the start of the story, and not the end. Melanie felt that life was beautiful. She was fucking the cock of her life AND had a husband...

The New Boss Ch. 02

by iraussieguy on Sep 12, 2017
BDSM

The New Boss Part 2:A Weekend Away (This story is a follow on from my story entitled The New Boss. It can be read separately or as a continuation from part one.) I sat at my work desk, finished checking my hand written note, then re-read it again one last time. ‘Pick me up as soon as you can after work on Friday, we will stop for dinner on the drive down....

Pitbull

by panther1282 on Sep 13, 2017
Sci-Fi & Fantasy

"Jamika girl I can't wait to get inside this party. When I get in here, I'm going to get my first drink, get drunk, and dance my ass off. Hell I deserve it!" Tamara Dee said standing in line with her best friend, Jamika Debarge. Jamika rolled her eyes. "You mean get drunk and get raped?" Tamara gave Jamika a playful shove. "You know what? You need to rela...

Cuckolded

by H piltdown on Sep 14, 2017
Interracial Love

We were driving home from our mountain vacation spot after celebrating our tenth anniversary. As usual, boredom was quickly overcoming us. So, to pass time, we took out the pocket tape recorder, and recanted the story of one of our recent rendezvous'. The following is a transcript of that tale, and you can believe us, that trip passed very quickly. We hope t...

Consequences - Ellen

by thecelt on Sep 14, 2017
Loving Wives

This is the third in this series. For those of you who wanted to see a conclusion to Consequences – Erin, one is in the works. Thanks to Angel Love for her editing and her suggestions. Any mistakes that you find are mine since I can't leave anything alone. * My name is Spencer Christian and I am a 48-year-old construction engineer. I'm the guy that se...

NTRPG - Fallen Heroines

by BlueMuffin on Oct 15, 2018
Sci-Fi & Fantasy

Warning: This story contains elements of Cuckoldry (NTR) and Non-Consent. If those aren't your jam, this is your chance to leave. *** A brisk morning breeze whistled through the bare branches of the forest that surrounded the small village of Eversdale. The hardy inhabitants of the frontier village, normally up and working as soon as the sun's rays touched...

Debbie

by Excalibur_1949 on Sep 15, 2017
BDSM

Debbie wasn't the best looking girl in the office. In fact, the waste bin looked more attractive. But there was something about her that I couldn't put my finger on. She was hard working. She often stayed behind when everyone else left. Never did I have to chase her up over a project. Her dead lines were always met easily. In truth, she was about five, fiv...

Dangerous Games

by Many Feathers on Sep 16, 2017
Exhibitionist & Voyeur

At forty-two years of age, Jackie Anderson was an attractive looking brunette that looked more like a woman in her early thirties. She still wore her hair long, usually in a ponytail that helped to make her look younger as well, which probably helped to contribute to her being mistaken for a much younger woman. She worked out, though not as often as she woul...

The Meeting Ch. 02

by SoNaughty on Aug 30, 2017
Group Sex

Robin It has been a few days since Sherye and I shared that wonderful night together. I have been wanting to call her, but was not sure if I should. I have never been with a married woman before and I think that is what has been the cause of my reluctance to call her. The problem is that I can not seem to get her out of my mind. I keep thinking of the marve...