Pegging Stories

1,124 results
Orientation
Length
Source
Infinite Scroll

Learning The Ropes Ch. 03

by TheKinkyIndianGuy on Jul 10, 2018
BDSM

This is a fictional story; any resemblance is just coincidental and uncanny. I highly recommend reading previous chapters first, to understand the characters and plot better. Fair warning: this is a BDSM story involving Female domination, spanking, humiliation, and other fetishes. If this does not interest you, then please find something suitable to your i...

Blowback

by dreadknots on Jun 18, 2018
Transsexuals & Crossdressers

Another story! This one is a sorta reversal of a typical mind control scenario, where the slighted nerd ensnares the stuck up bitch. What happens when it backfires and turns a horny guy into a sissy sextoy? Lewd shit, obviously. *** Chloe flicked through the tabs on her laptop's browser, skipping between links and trying to polish up her history paper. Thi...

Bottoms and Buttered Buns

by SEVERUSMAX on Sep 14, 2017
Interracial Love

Kelly's ass was certainly tempting, but I had already committed myself to fucking Shannon next, not to mention that I needed to rest my cock for a little bit. After fucking Sally, Kelly, and Belle that morning, my dick was a little sore, if still semi-hard. Even so, I wanted Kelly's ass fucked...she was perfectly positioned for it and properly lubed as well....

Born to Be Ch. 05

by DamienDeath20 on Feb 10, 2020
Transgender & Crossdressers

A.N. Back for some black on white! :D If you want more stories by me look at my profile! All you need to know is there :) JUST A FUN FACT also, this is not the final chapter, not at aaaaaaaaaaaaall, there's maaaaaany more to come. You'll see why I say that at the end lol, just again letting you know ahead of time, no reason to worry. The Following Co...

The Price

by jackie_em on Mar 2, 2020
Transgender & Crossdressers

This story includes cross dressing, feminization and sex between a male and female, including pegging. ************************************ I had been dating Sherrie for a few months. It was summer vacation, so we had time to spend together. We had made out and she let me touch her but only over her clothes. I was 18, as she was and I was a virgin, almost...

The Portrait

by CindysBob on May 4, 2020
Loving Wives

This is a work of erotic fiction. It involves themes of voyeurism and husband/wife infidelity. There are scenes of rough sex. If this offends you, don't bother reading it. Please vote and I appreciate comments. This is a reworking of an earlier story I posted. XXXXXXXXXXXXXXXXX "Anything," Leanne answered with a wry grin, her green eyes widening with misc...

Born to Be Ch. 04

by DamienDeath20 on Dec 9, 2019
Transgender & Crossdressers

A.N. Back at it again with the interracial pegging!! Thank you all as always for your patience while these chapters come out! And thank you a huuuge amount to my supporters! :3333 you guys make it so I have food on the table and can keep doing what I love! The Following Contains: Black Amazon Woman on little girly white boy who is progressively becoming...

The Camp Ch. 02: Letters

by saddletramp1956 on Jan 27, 2020
Loving Wives

The Camp 02: Letters The following was mostly inspired by Andrew1968's story, "The Birthday Boy." The characters are different, as is the outcome, but most of the original premise remains the same. I won't go into all the details about what happens at the camp, as that is covered in my previous story, "The Camp Ch. 01:Mike and Sandy." Instead, much o...

'Jenny' & 'Mike': Fantasy Sunday

by hfernandez1983 on Sep 25, 2017
Transsexuals & Crossdressers

This is the third chapter in the 'Jenny' & 'Mike' series. If you haven't read the first two chapters 'Jenny' & 'Mike': Date Night and 'Jenny' & 'Mike': A Day Out, then please do check them out. As already stated, my interest in pegging was the starting point of this series. It has since developed into more of an exploration of 'Gender Play' with...

Femdom Between Friends Ch. 01

by jack562004 on Sep 11, 2017
BDSM

Karen and I had worked together for a number of years and had developed a close office friendship, frequently lunching together and even traveling together to the half dozen yearly trade shows requiring a company presence. She was very pretty in that "girl next door" kind of way, with long strawberry blonde hair and a softly freckled face. I admired her sha...