Shemale Dating Stories

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Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

Hooking up with a shemale

by Gliorna on Apr 29, 2025

You are Blake Tallbrook, a semi wealthy man living alone for the moment after a break up a year ago. You have been working hard for the last year just focusing on your job. Your Sexual life has been normal one night stands with random girls from bars late at night. But you have become interested in something else. A girl with something special. You have look...

Sally: His Perfect Shemale Partner Ch. 1

by PunkFan on Sep 16, 2017
Fetish

I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy who has had a few sexual experiences before this chapter in my...

My Girlfriend - A Shemale

by ARandomGuy on Apr 22, 2025

(hello everyone, who is reading this. so first thing, first. I'm not a first-time writer but my other account is gone. so this is my first story from this account. 2nd thing, I'm not the kind of guy who loves to jump on straight to fucking. so yeah, the story is gonna take some build-up but is not that long that you'll feel sleeping is better than this story...

Pam's Gangbang Experience

by majicman21 on Oct 14, 2017
Group Sex

Author's Note #1: This is a continuation of 'Pam's Shemale Experience' from the Transsexuals/Crossdressers category. Although reading those stories is not necessary to appreciate this one, it will enhance the experience. Either way, enjoy. ***** The splashing in the hotel pool provided an aural backdrop as John read his Kindle, learning about the history...

Mark's Surprise Ch. 1

by Kip Carson on Sep 13, 2017
Fetish

Mark had just broken up with his steady girl, Diana 2 weeks before. He was finding it really hard to get over her. They had been dating for almost 2 years, and he was devastated when he caught her in "The Act" with 2 guys from the football team. He saw her car at the hotel, and pulled in to see what she was doing. He stood outside the motel room door, and co...

When Sara Met Bob Ch. 03

by yellowfrog on Sep 14, 2017
Fetish

It is a standing joke at all nail salons. A woman that has nine long fingernails and one trimmed short is for-sure into prostate massaging her husband. I decided to go one step further. I went and enrolled Bob at the local community college in a six-week course for manicure and pedicure. from that day on, Bob and only Bob manicured my nails. After peeing in...

Genie Chronicles - Make a Wish 03

by BebopJet on Sep 19, 2017
Sci-Fi & Fantasy

A big thanks goes to Joe Brolly for the original Genie Chronicles. As many people have done, I'm simply taking his original story format and giving it a twist. Fair warning, lesbian and futa (shemale) sex will feature heavily in this storyline. Thanks to Ultrafem, Stickymon, NinjaKitty, and Anasheya for drawing pictures that inspired these stories. Milla Jov...

Willing Submission to a Dickgirl Ch. 02

by ArthurSummer2 on Apr 4, 2018
Fetish

Note to the reader: This story takes place in a futuristic world where body modifications and high technology are common place. Because of this, there are a subset of women who choose to have male genitalia attached to their bodies. These cocks and balls can be, and often are, much larger than natural male genitalia. So if you are not interested in futanari/...

Ghosts of The DMV

by RaistlinMajere on Jan 16, 2019
NonHuman

CHAPTER 1 - GHOSTS OF THE DMV Amelia yawned and sat up. Her long, fluffy brown hair was a mess about her head and her plain white pajamas were messy. She kicked the covers off and didn't pay any attention to the fact that a ghostly woman stood naked at the foot of her bed. Her bare feet were chilly on the wood floors of her quiet little home and she walked...