Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Enter Jenny

by Bivet on Sep 14, 2017
Romance

When my wife died, I was devastated. Married less than 10 years, and taken from me suddenly. More than just my wife, she was my best friend. We would laugh together, cry together. We had amazing adventures all over the country, and our intimacy was stuff of legend. At times it was all I could do just to get out of bed in the morning. I knew that I had to get...

To Reign in Hell Ch. 01-06

by SEVERUSMAX on Oct 31, 2017
Erotic Horror

Chapter 1 I felt an incredible pain all over my body as I awoke, thinking to myself that this was the hangover from Hell. I didn't know just how accurate that statement was, however, until I noticed the heat all around me and smelled the Sulphur smell ... and then heard the screams of agony from everywhere, in every direction. I looked around and saw people...

Maria the Closer

by joefelton on Aug 17, 2017
Fetish

Chapter One Maria Williams checked the time on her iPhone... three o'clock... time for her weekly call to Angela. She and Angela are best friends, and have known each other since attending kindergarten together at Mariposa Elementary School. Their relationship could be described more like sisters, than best friends. They confide in each other about everythi...

The Medb Wine Club Pt. 01

by tdallyn on Sep 19, 2017
Group Sex

Barbara's text message came across my cell phone just as I was getting ready to leave work. It said, "Don't forget about the wine tasting tonight." "Damn," I said out loud. I had indeed completely forgotten about it. I'd learned about it a few weeks earlier when we were both in our kitchen at home on our computers. I was in the middle of doing something...

Khel and Brom

by Dudebulge on Sep 15, 2017
Sci-Fi & Fantasy

CHAPTER 1 Let me begin by describing myself and a little about my life. My name is Khel, and I am an elf. I'm fairly young for my race, I suppose I'd be about the equivalent of early twenties if I was a human. I was raised from infancy in a theatre troupe and have come to fancy myself as something of an accomplished actor. The company consists of about thi...

Inescapable Pt. 01 of 02

by optimizer888 on Jan 13, 2018
Transsexuals & Crossdressers

I'd only been here a few minutes, and I could tell their reputation was entirely deserved. It's not like I was a stranger to strip clubs. And, here in Nevada, legal brothels. You follow cheating spouses around for a living, you're going to clock in the hours there. "Gerry's Place" had more variety than most, and I hadn't seen a dud yet. All the women were t...

Curse of the Trickster God

by PastPresentFuture on Mar 7, 2018
Erotic Couplings

Part One: God of Travelers From the tip to the bottom of the shaft, the cock was at least four feet tall. "Evidence for the argument," I said to Theo, "that size does matter." Theo laughed, shaking crumbs off the blanket where we'd had our picnic. "Pop quiz, Cass. What's the Greek term for the big weiner there?" Of course I knew the term for it, I'd just...

Love on a Desert Island

by bravebombadier on Sep 25, 2018
Romance

I had seen the sails of the ship as she approached and I had made my way through the forest to the headland, the same headland overlooking where the mutineers had been sunk on the rocks that were hidden just below the surface a few hundred yards offshore. I knew with certainty that this ship would hit those same rocks. They were sharp steep pinnacles that...

Loosening Up Bk. 01 Ch. 16-20

by SteveWallace on May 14, 2018
Group Sex

Chapter 16 -- Trying New Things and a New Flash Dave started to move in and out, sawing well over eight inches of man meat in and out of her sex. As he moved, so did Sean in her ass, but without the long strokes that Dave could muster because of position and size. Kat's eyes closed as she savored the rapture of the double penetration. Alice reached in with...

Prince Gyllen Ch. 16.2

by MythMaker on Aug 20, 2019
Sci-Fi & Fantasy

As the sun peeked over the eastern horizon and beamed its first rays of dawnlight over Caliga, the prince of Platina regained consciousness from the depths of dreamland. Despite having almost every ounce of his energy reserves dried up the previous night, Gyllen's few hours of sleep were anything but sound, having been stuck in the exact same position on his...