Shemale Surprise Stories

136,276 results
Orientation
Length
Source
Infinite Scroll

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

Pam's Shemale Experience Ch. 05

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

"Take it, slut, right down your throat!" "That's right, take it, fuck yes, choke on it!" "Fuck yes, babe, that feels so fucking good!" Pam swooned, kneeling subserviently as her temporary owner took her pleasure. "Fuck, Pam, your throat feels so good!" The lustful shemale was as usual in total control. One hand had a fistful of Pam's hair, while the oth...

All the Way

by NearMiss on Sep 18, 2017
Transsexuals & Crossdressers

A different spin on the typical 'I got caught dressing up' story. I've always been fond of large women, not obese necessarily but you know, big. Like Amazonian big. Tall, big curvy hips and a chest to match with broad shoulders, but not in a masculine way mind you, but kind of proportionate for a girl. Let me tell you they aren't really that easy to come...

Accommodating Neighbors Ch. 04

by gentlegem on Sep 14, 2017
Mature

Chapter 4 Our Visit to the Adult Toy Store (Authors Note. This is the 4th story in a series. For those of you who haven't read the first 3, it is based on the relationship of a 44 year old red haired lady and a 63 year old man who live in the same apartment complex. Much of it is based on true characters and events.) * Becca and I didn't see each other f...

T-Girl Van Sex

by available269 on Sep 12, 2017
Transsexuals & Crossdressers

Pulling up to the curb near the bookstore one recent night, I happened to notice a nice looking custom van drive by very slowly. Looking intently at the driver as it passed by, I noticed that the driver was a very sexy looking woman, and she gazed at me intently as she passed by. The van pulled up to the curb in front of my car and parked. Shortly afterwar...

Punished in Paris

by maia24 on Sep 16, 2017
Transsexuals & Crossdressers

Maria the very pretty Irish transvestite had arranged to meet the men in Paris. She had agreed to be taken to a house in the suburbs to be punished, abused and sexually defiled by a number of men. She was dressed in a purple mini dress and wore very expensive lingerie. She was totally smooth and as she walked to the avenue to meet one of the men she was full...

Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

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Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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Brazillian Punsihment

by Ravenarioch on Feb 7, 2018
Transsexuals & Crossdressers

Frank Shepard a private detective who is trying to find his luck in Rio de Janeiro awakes in his bed during the day of Carnival, the sun's rays hitting his eyelids he turns himself over in bed and looks at the sky on this lovely day. His sky blue eyes thinking about what a horrible day to be a private investigator, his case was to find the little brother of...

Jenna & Stephen Ch. 01

by Naf_Noparts on Sep 12, 2017
Fetish

(Author's Note: This is a true story, one that tells of my hot experience with a friend who fucked me with a strapon. If you are bothered by the idea of women ass-fucking men with toys, then this story will not be to your liking. Thanks in advance for all constructive feedback!) * Jenna and I have been friends for nearly 15 years. We dated ever so briefly...