Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

Allison's Adventures in Wonderland

by BlueManticore on Oct 6, 2020
Sci-Fi & Fantasy

Chapter 1. Allison's Adventure Begins Allison sat on the grass, leaning against a tree on her college's campus, taking a break, when she got her first surprise of the day. From seemingly out of nowhere, up walked one of the most beautiful women she had ever seen. She looked to be a college student like Allison, and she had long-shoulder length hair like All...

Helping Wendy

by Lynda68 on Oct 5, 2020
Group Sex

Melissa and me have been married for just over fifteen years. We were together five years before that. We have a lovely house, in a semi rural area. Mel works from home, and I work in a warehouse, four shifts on and four off. With having no children, we have took on a bit of a nudist lifestyle around home. The sight of Mel naked in the garden still gets me...

The Road to Darker Desires Pt. 03

by nekkid_handyman on Oct 6, 2020
Exhibitionist & Voyeur

The Road to Darker Desires -- Part 3 Donna and Tom Simpson were lying in bed holding each other close. They had just finished a quick and frenzied lovemaking session after confessing and detailing the sensual events of each other's day. Tom had exposed himself and masturbated in front of his sultry co-worker at her request. Donna had experienced oral pass...

Fortunate Confluence of Events Ch. 02

by Twelfthmonkey on Nov 16, 2020
Fetish

Fortunate Confluence of Events, Chapter 2. Dear readers: This story seems to be writing itself faster than I had anticipated. If you have not read Chapter 1, I strongly urge you to do so before reading this one; it's not long and will give you the needed context to truly appreciate the story line and characters. This one runs a little longer, and deeper int...

Three Square Meals Ch. 74

by Tefler on Sep 25, 2017
Sci-Fi & Fantasy

"We have been sssuppresssing all newsss of the losss of our forcesss in the Regulusss sssyssstem, jussst asss you ordered, your Imperial Majesssty," Grand Prelate Melkadian said, glancing up at the vast draconic behemoth with no small amount of apprehension. "The Imperial Information Bureau hasss kept all talk of the battle from newsss feedsss, and any queri...

The Sketch

by spaldan on Jul 24, 2018
Exhibitionist & Voyeur

Introduction Bill was burned out at 28 years old. He hated to admit it, but he was totally fried. He detested when friends and coworkers grumbled about working late nights or being exhausted from a day at the office, because Bill knew they were really bragging about their jobs and their work. Besides, they were rich men's problems, not gritty blue collar wo...

Halloween Party Surprise

by m_storyman_x on Sep 25, 2017
Group Sex

I have always loved parties, even though I never seem to get invited to too many. I also love holidays, and one of my favorites has become Halloween. When I was a bit younger and raising a family it was always fun to dress up and take the kids out trick-or-treating. We usually made interesting costumes for them and tried to be innovative in ours as well. One...

Three Square Meals Ch. 73

by Tefler on Sep 25, 2017
Sci-Fi & Fantasy

Matriarch Tsarra Perfaren nibbled apprehensively on her thumbnail as she stared at the holo-map projection of House Perfaren territory. Biting her nails was an unfortunate new nervous habit she'd acquired, but considering the stress she was under, such weakness was understandable. She had bags under her eyes from lack of sleep, and her exhausted dark green o...

Mommy's Special Boy

by Shelly7 on Aug 25, 2018
Transsexual

Ever since I can remember my mom loved me very much, she was always saying its so much more of a worry having boys than girls. When my father died of a heart attack when I was ten years old, mom was there even more in my life, I believe it was then that she directed me on a specific path in life, of course I could not see that all through my childhood, but n...

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Mom's Punishment

by embarrassedboi29 on Dec 2, 2020
Exhibitionist & Voyeur

**Public** Here I am again, sitting in the principals office for the 3rd time this month. My mom is going to kill me but I don't really care. What's the worst she can do? Yell at me? My teacher was being a bitch and so I told her so. "Hello, Mrs. Michael? Yes this is the school principal. I am calling because we have your son, Jared, in our office again...

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