Pegging Sissy Stories

7,509 results
Orientation
Length
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Infinite Scroll

I Put on A Cock

by ndeavour on Jan 6, 2020
Erotic Couplings

Hi, my name's Liz. I'm not about to tell you how old I am -- but I have a 25 year old son, so that should give you a sense. I've only just stopped coloring my hair and begun letting a whole lot of silver to emerge. I no longer have the slim figure I did before having my son; I gained nicely in the boob department, but picked up some extra padding all over. I...

Rubber Femdom World

by Rubberfoot on Oct 15, 2020
BDSM

Something strange was happening in the small college town of Little Gadsden. None could say what was causing it, but the one thing that was certain was that it started after the comet crashed near the town. Little Gadsden was a small place, of no more than a few hundred inhabitants, so the event was the most talked about thing for weeks, even though nothing...

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Moving to the Sexworld

by Shendude on Dec 19, 2010
Science Fiction

Imagine an alternate universe where casual & free sex, sexuality, & nudity are everywhere, where all people are at least bi, where there are almost no sexual taboos, where everyone's a nympho or satyriac, and where almost all interpersonal interactions have some form of sexual content, and it has ALWAYS been this way. Now, imagine that this world com...

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Sexy Black Boots

by latexdoll on Apr 8, 2007
Fantasy

While walking through the local mall you suddenly notice one of your fellow coworkers coming toward you and not wanting to deal with this obnoxious jerk you find yourself quickly ducking into the next store you see to get out of sight. With out even paying attention to the store you find yourself walking all the way to the back of the store to get out of sig...

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Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

Blackbone Crossing

by DonSwami on Dec 4, 2020
Fantasy

AUTHORS NOTE: This story is still a work in progress, I’ve got a lot of idea’s on where I want to take it and what different chapters are going to be. I decided to publish Blackbone Crossing because I really wanted some feedback/ideas. The story is open to other writers, so feel free to submit your addition! Some chapters I’m still working on and I haven’t p...

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Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

Let the Games Begin! (JOI Idea)

by JMR85 on Mar 25, 2019
Toys & Masturbation

Alright, let's skip the long intro. Forget "setting the scene", forget about what I'm pretending to wear. I know you usually just fast-forward all that stuff anyway. You're mine, tonight. I'm going to give you your tasks, and you're going to follow my orders as close as possible. And, the tasks you achieve successfully are going to score you points. Points...