Trans Surprise Stories

136,543 results
Orientation
Length
Source
Infinite Scroll

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Slow Descent into Sissy-Hood... Ch. 01

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

Beta boy beginnings. It started when I was online, lonely and drunk. I'd been at University for maybe three months at that point, struggling along with a Masters degree in Economics. Unlike my undergraduate years, I had decided to live alone in a one bedroom flat - I thought that with more privacy would come more focus. What I hadn't counted on was that wi...

A Master PC Tale

by radiedwa on Dec 31, 2010
Science Fiction

Welcome John Doe to the Master PC Universe. Don't know what that is well you are in for a wonderful treat. To get started just select your sex below. Or if you wish to read more for background and history... I suggest a word from JR Parz himself... http://www.asstr.org/~JR_Parz/MasterPCUniverseWriters.htm Also, all the stories he found to his liking, along...

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Why I Prefer Sex Work to Dating

by ShyTammy on Sep 17, 2017
Non-Erotic

First off I want to apologize for not posting anything. Emily and I are working on the next chapter of her story and I still have it on my desk to finish the "Our Secrets" series. So hopefully you'll have something new to read soon. In the mean time I wanted to get this out there. So it is the morning after Christmas when I started this and I am feeling so...

Roommate's Surprise

by Eroreader55 on May 21, 2019
Transgender & Crossdressers

My name is Tom and I recently moved to a new city after graduating from college. I'm 24 and I didn't know anyone in my new city so I was looking online for roommates. I tried to find a guy roommate but had no luck finding someone who was clean and fit the bill for what I wanted. I work in the medical field so I am on 12 hour shifts and I needed someone to ac...

The Trade Show Pt. 07: Conditioner

by GeorgiaD on Sep 23, 2019
Transgender & Crossdressers

Sorry for the long delay in writing this but Georgia's life has been a bit of a roller-coaster ride recently. xxx ***** The weather was glorious. A perfect English summer's day. Cindy drove us with hood down to Totnes, a lovely and quite alternative town not far from Plymouth. On the way, we talked about everything imaginable. Politics, fashion, hairstyl...

In Sheep's Clothing

by Cyberweasel89 on Oct 24, 2020
BDSM

Clarabelle "Clara" Bullock was 24 years old and a professor of art at Florida University. Living in an apartment in the suburban college town, she'd only had a few lovers, never had sex, and had few friends outside of some of her fellow faculty at the college. She had one secret, though... Clara had always dreamed of BDSM. She'd read novels, done r...

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Best of Both Worlds

by TransChick on Sep 16, 2017
Transsexuals & Crossdressers

This is the first chapter in a multi-chapter story. There's no sex or anything in this chapter, so patience is encouraged. ;) ~~~~~~~~~~~~~~~~ So I want to tell you about a pretty crazy period of my life. Like a lot of fun, exciting things it ultimately couldn't last forever, but I definitely look back on the time with a big smile, and I appreciate it both...

A Long Cool Woman in a Black Skirt

by DreadWriter6969 on Mar 26, 2019
Transgender & Crossdressers

I first saw her in the lobby of the hotel in which I was staying for my conference. I'm the national sales manager for a large manufacturing company. We hold a national sales meeting every year to which all of the regional managers are gathered for education on new products, sales techniques, etc. She was a tall woman, actually taller than I, but I noticed...

Lets Say - An Orgy.....

by sexual_indian on Sep 13, 2017
Group Sex

Another of my narrations, you might notice most of my stories are incest, but this one is a little different. I am 28 year old, regular guy. The encounter i want to talk to you about now happened when i was just 18 years old and just joined college to do my degree first year. I was not a virgin by then. But this is much different and unique in my life as I...