Shemale Girlfriend Stories

56,648 results
Orientation
Length
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Infinite Scroll

Amanda and Me Ch. 02

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. As I lay there thinking about the night before I was surpris...

futanari girls going commando

by brain66 on Feb 14, 2019
Exhibitionist & Voyeur

introduction various futanari girls go about their daily lives. out of fear of ridicule (though to some perhaps there is no reason to fear and they are just being paranoid) they hope to keep their futanari selves a secret. one day however events occur that result in them going commando these events can voluntary or forced upon them. however without the prote...

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The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Riding in Cars with Shemales Ch. 03

by lfullback on Sep 25, 2017
Transsexuals & Crossdressers

It was the last day of classes. All of the finals were finished, and everyone was celebrating. My finals had been particularly rough. It was the last semester of my freshman year and I didn't study as much as I should have. The problem was that I lived next door to a girl that I had been having sex with for most of the semester. Terra could be quite the dist...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

Pool Party

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

Happy to share this story with you. This one is a bit odder than the usual fare and I warn you going in that this story involves well hung celebrity shemales. I kind of wanted to save it as a surprise twist, but that seemed a bit unfair to have the story seem like a typical lesbian celebrity story and then have it be about girls with hot cocks instead of cun...

Date a celebrity

by pipster2927 on Sep 24, 2019
Amateur

Please add to this story. This story takes place in an alternate universe and therefore all main characters are 18 years or older. You are John Smith. You have just received an email from Celebrity Services congratulating you on winning a date with a celebrity The email reads: Dear John Doe We are happy to announce that you have won a date with a star of you...

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We Have Ways Of Making You Stay

by yano on Sep 13, 2017
Transsexuals & Crossdressers

Firstly a few words from Miss Anne. The Kinky Brides Group was formed some twenty eight years ago and we have had hundreds of gorgeous brides and studs pass through Tulle Towers in that time. My name is Miss Anne and, when my personal stud Yano decided he was leaving us, we had to employ drastic measures to keep him. Yano has been with the KBG for over twe...

Shemale Beauty: 1st Female Conquest

by silkstockingslover on Sep 13, 2017
Transsexuals & Crossdressers

Summary: 18-year-old discovers her powerful sexual persona. Note 1: This is the first of potentially many shemale stories starring the beautiful seductress Kara... Note 2: Thanks to... Tex Beethoven, Robert, and David for editing this story. Shemale Beauty: 1st Female Conquest Everyone has hobbies. For most people, hobbies can be activities like trav...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....