Tranny Surprise Stories

136,341 results
Orientation
Length
Source
Infinite Scroll

Sammi's Gloved Threesome

by JSF79 on Apr 4, 2018
Transsexuals & Crossdressers

This story follows on from Sammi's Gloved Surprise and is response to some kind readers who wanted to know what happened next. ***** George sat in the dimly lit bar talking to Sammi, trying to make out as much of her strong, gorgeous features as he could and watching her bring her glass to her exquisitely painted lips to take a sip of her drink. Although o...

The Path to Happiness Pt. 09

by brendachaplin2000 on Sep 28, 2020
Transgender & Crossdressers

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman". On a positive note David had started a relationship with Adam, and...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

The Benefit of Plasma Television

by Kitkat103 on Sep 12, 2017
Toys & Masturbation

MaloMarz6969 -- Lol what a freaking idiot. So what are you up to? Sbarron85 -- Just waiting for Matt at his place. He is supposed to be working late. MaloMarz6969 -- Aha. I did not know that office drones had to work so late, honey its 11pm! Sbarron85 -- I know that, what are you implying? MaloMarz6969- Well I think he is out too late to just be desk joc...

The Virgin Tranny & the Bride Ch. 02

by yano on Sep 25, 2017
Transsexuals & Crossdressers

This is part two of a confession related to me by my transvestite friend Roberta, and like the first part, is so sexy without any further elaboration by me. Having seen some of the photographs, I can only say that she strays very little from the truth. Meantime I am trying to convince her to let me publish a few on the Internet. Watch this space. Exactly tw...

Always Read Before You Sign Ch. 09

by Reaver90 on May 12, 2020
Transgender & Crossdressers

Paula was in the living room, having some toast as she watched the news on TV. She was waiting for Samantha to appear so she could launch her secret surprise on her slave. Samantha was in the kitchen, making herself a cup of tea. Samantha always enjoyed a cuppa in the morning. As she waited for the kettle to boil her mind drifted back to a few days ago wher...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Tranny Fantasy World

by panopticind on Sep 15, 2017
Transsexuals & Crossdressers

If I were not afraid of shame and assuming practicality is no issue, I'd turn myself into a piece of fuck-meat for well-hung trannies. I'd have an army of the world's most beautiful and well-hung chicks with dicks living in my mansion. I suppose they'd receive a salary as an employee of mine and not be slaves or something. But I'd say I'd need about 500 tran...

There's Something about Sarah Ch. 07

by MicheleNylons on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Seven -- A Conclusion of Sorts Tina flatly refused to attend the reading of Amanda's will and to be honest I didn't blame her. "Sarah; it's between you and Sloane and it's legal shit. I don't think having a former prostitute and current transgendered porn star is in any way going to serve you well. Besides; you need to stand on your own two feet. I...