Shemale Pegging Stories

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Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

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Brazilian Shemale

by Thorsten007 on Dec 30, 2017
Transsexual

Rules: Needs to be a brazilian shemale with big tits, a fat cock and a nice round bubble butt! Feel free to continue and create new storylines.What's next? James Kingston Pablo What's next? James Kingston Pablo...

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Some Girls are Different

by TransKat on Sep 25, 2017
Transsexuals & Crossdressers

"Mister Jones, will a king size bed be ok?" said the woman at the hotel's front desk. "Yes, that's fine" Jim said as he put his credit card back into his wallet. "Thank you..." as he looked at her name tag, "..Amy. Do you have any recommendations for fun places to visit around here?" "Hmmm...that depends on what type of fun you are looking for. There are...

Mistaken Identity

by kcwilder69 on Mar 25, 2019
Erotic Couplings

It was my first week at the new job, and I was drained from learning new protocols and procedures. And how would I remember the names of all the people I'd met? I parked the SUV in the driveway, looking forward to a warm dinner and a quiet evening. Approaching the house, I see it's dark. Why isn't Laurie home? She's always home by this time. I open the door...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Shemale Shopping Spree

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye a...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

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...

Grace Under Fire Star Does Blacks

by Samuelx on Sep 17, 2017
Celebrities & Fan Fiction

Brett Butler looked at herself in the mirror. At the age of fifty three, she still looked good. Blonde-haired, blue-eyed and curvy. Blessed with Irish good looks that simply refused to fade. Unlike her star in the upside down world of Hollywood. That one faded so damn fast she went from being a household name to a nobody in no time. It had been so long since...

Black On Black Pegging: True Love

by Samuelx on Sep 11, 2017
Fetish

I don't know why he thought I wouldn't be able to handle it. I really hope he'll stop hiding stuff from me after this experience. Female on male strap-on domination, Afro-Caribbean style. Seriously. I honestly wish he told me about this really hot fetish of his sooner. My name is Malinda Lexington and I'm a short-haired, green-eyed and kind of chubby young B...