Shemale Surprise Stories

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Shemale Surprise

by luckybaldrik on Sep 12, 2017
Transsexuals & Crossdressers

It was a Saturday night and I was chatting up this girl at my favorite bar. Her name was Heather and she had short light brown hair. She was cute, big in general, big boobs and a big ass, but she wasn’t pudgy, and in fact she had a very athletic body. She wore a short white miniskirt with a dark tank top and pink fishnet type top over it. We had really hit...

Shemale Surprise!

by BigAndy922 on Sep 14, 2017
Transsexuals & Crossdressers

I'm a country boy. About a year ago I left my small town and moved to the city so I could attend university. Initially, I had nowhere to stay so I was going to move into my cousin Mike's flat for a few days with him and his roommate, Sandy till I found somewhere of my own. Mike and Sandy worked together at a law firm in the city. Mike had a fiancée` but he...

Shemale Surprise.

by ceb35 on Sep 16, 2017
Sci-Fi & Fantasy

As a single woman I do spend quite a bit of time enjoying porn flicks on my Kindle Fire. But I never imagined that anything I watched would ever happen to me. But it did! My girlfriends and I often go out to one of several bars nearby my home. We go as a group just to hand out and talk and occasionally meet new people. Some are nice and some are just compan...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

Shemale Surprise Ch. 02

by luckybaldrik on Sep 16, 2017
Transsexuals & Crossdressers

I woke up to find myself staring at a nice ass hanging over my head. That ass belonged to heather, an extremely attractive shemale who tricked me into letting myself get gangbanged by a group of shemales. She then let me stay in her apartment, as my clothes had been stolen a long time ago. I then realized that I was being sucked off by heather. She had gotte...

Girlfriend's Shemale Surprise

by Artvan1 on Sep 24, 2020
Transsexual

As Carter finished unpacking after dinner, he couldn't help but smile. His last summer before having responsibilities would be spent in the beautiful home belonging to his girlfriend's parents. Carter and Chloe had only been dating for a few months but were both entirely consumed in the early parts of their relationship. From hand holding to mini-golf the yo...

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"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Agents of SHIELD (parody)

by Deckard6969 on Mar 2, 2020
Celebrities & Fan Fiction

Starring: Racquel Darrian as herself Lily Cade as Madame Sin Chloe Bennet as Daisy Johnson Ming-Na Wei as Melinda May Wendy as Madame's butch bodyguard Scene 1: Daisy and Melinda are at the SHEILD command center looking at a set of images displayed on several large monitors. Following a brief, awkward discussion, it becomes apparent that a wealthy hei...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...