Trans Pegging Story Stories

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Orientation
Length
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Infinite Scroll

Femdom Scenarios

by unknown156 on Apr 29, 2025

Live through your wildest femdom fantasies as these sexy girls dominate and humiliate you to orgasm. Anyone can feel free to add their own storylines but they must abide by the following simple rules: Every character involved with the JOI or any other sexual activity MUST BE 18+. You can have characters who are under 18 but they can not be in any way involv...

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Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

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My Trans Girlfriend and My Sister

by ArkansASS on Oct 6, 2020
Transgender & Crossdressers

Warning: This story involves sex with a trans woman and my sister. If either transgender stories or incest are not to your liking; unfortunately, this story will not be for you. I have given my trans girlfriend in the story feminine pronouns (eg. "She" and "her") For the sake of creative convenience. I started dating Michelle about 3 months ago. She is my t...

The Last Frontier - I Hope Ch. 01

by massageguy64 on Jun 19, 2019
Erotic Couplings

So if you have read my work you know that I mostly write about my experiences getting massages, mostly Happy Ending massages. These are all true stories, and I hope my writing reflects that. While a lot of these happen while I travel for business, they also happen at home in Texas. Sometimes they are basic hand job happy endings and sometimes they are full o...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Start the Revolution without Me

by SevMax2 on Sep 24, 2019
Sci-Fi & Fantasy

Inspired by the New Order universe created by Freddie Clegg. *** "Bloody bollocks, they've completely gone off their rockers!" I remarked as I watched the election results being televised. "Tell me about it. We've seen how much hysteria this 'Me, too' crap started here, to where Al Franken had to resign for some stupid photos. Why in the world would anyon...

Spider + Cat + Redhead Ch. 01

by Zev95 on Sep 12, 2017
Celebrities & Fan Fiction

A/N: I feel I should explain. This is one of the series, like Marry The Knight, that I simply get a lot of requests to continue. However, unlike MtK, its story is tangled up in Ultimacy, which is sadly slow-going. I apologize. However, people keep asking, and this did end on a cliffhanger, and I know how people appreciate having just a nice story about Peter...

Search for a Great Prostate Massage

by massageguy64 on May 29, 2018
Fetish

This story meanders a bit, through a number of experiences, but the end is a bit shocking. At least for me. This story, like all my stories comes from my personal experiences. Including the final one which was just this afternoon. All of the names and locations have been modified. ***** My first submission started with me standing outside an asian massage...

Lynn has a Thing for Peter Ch. 01

by lateknew on Sep 14, 2020
Transgender & Crossdressers

This story involves two consenting adults. One is an experienced transvestite. The other is open minded, but has to still experience a bisexual encounter. I thank Nance for the help given to edit this story. ************* I finished work and joined the others rushing out the building towards the parking lot. I caught sight of her, walking towards her c...

Fucking Frank

by jakftx on Jun 25, 2019
Exhibitionist & Voyeur

In preparation for a trip abroad and back when they existed, I was cruising a particular set of online personal ads, hoping that I might find something of interest when there it was. He was gay, but looking for a female bodied person who was into pegging. OMG, my dream ad. I sent him a note, asking how he'd feel about being pegged by a trans gut, and we star...