Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

The Futa next door

by Abusedbyfuta on Jan 11, 2019
BDSM

You have lived in the same l cul de sacyour entire life. It's not a bad place to life, very much a part of suburban America. It's just not very exciting. You live in a large White House that looks the same as all the others on the street, probably a ploy by the developer to keep costs down. Every day you see the same boring neighbors, have the same boring ro...

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A strange night

by latexdoll on Oct 19, 2006
Science Fiction

Sitting home for another boring night of surfing the internet, you are about to give up on finding anything new when an odd link pops up at the bottom right of your screen. "Click here for the night of your life." Assuming it has to be some sort of virus or spyware you go to delete it. But something makes you pause, be it boredom, or simply the kno...

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Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

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Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Dungeon of Bad Ends

by Hacksource on Dec 12, 2020
Fantasy

Introduction. All great stories must start with an introduction. Welcome to the Dungeon of Bad Ends! Here, the harrowing main characters will do everything in their power to escape from the dungeon unscathed, fighting through many, many, wrong turns on the way out! The dungeon is a massive structure, existing in its own time period as it lays right under the...

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Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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AC: lost in the animus

by Damos on May 17, 2019
Fantasy

“David; nice of you to come!” a voice spoke and looking over there I saw the dark haired woman standing there greeting me, “This is the team, Lucy!” I looked over and seeing the blonde nervous woman she whispered, “Hi!” I looked over to Rebecca who whispered, “She fancied a man who died saving the world!” I nodded before saying, “Desmond!” she nodded before...

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Integration Ch. 01: Discovery

by takingitupthechutney on Apr 21, 2020
BDSM

Gavin grabbed a wet wipe. He went to pass it to Donna, but at the last second decided to wipe her crotch for her. "Thanks," she said with a grin on her face. "No one wants to lie in a wet patch after sex. Well I mean some people are probably into that, but that really doesn't do it for me. Either way it helps keep the sheets clean." Gavin giggled. "So what...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...

That Sleepover with Sam

by hannah_xox on Jun 19, 2018
Transsexuals & Crossdressers

"How long will you be?" Sam text me, eager to get the first pint down. We had arranged to meet in a pub after work. Our girlfriends were away together for the weekend so we planned some time together. Drinks in the local on Friday night, followed by a walk around London on the Saturday and then a house party on the Saturday night. Sam had to run some errands...