Crossdressing Pegging Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

She Subdued Me with Sweaters Pt. 03

by Woolmohair on Mar 3, 2020
Fetish

I spent a fair amount of Thursday distracted with thoughts of the coming weekend. My mind couldn't get around this feeling of anticipation, my desire to be with her. I was feeling anxious. I was thinking that I would do anything to be in her company. It was almost overwhelming. An associate and I were working on a project. He asked me why I was so crazy ab...

My Metaphor

by hyperpress on Dec 24, 2018
Fetish

The audience drops into a continuing story written in first person POV (mostly). The following based on a true story. Given enough time, any question that occurs to the reader shall be answered, eventually. * I woke the next day, showered, put on a comfortable chemise, a microfiber and nylon blend thong and open toed sandals, made some coffee and sat down...

Quiet Servitude Pt. 04

by AmandaMI on Sep 12, 2017
Transsexuals & Crossdressers

Author’s Notes Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions. To make the action flow more freely and the stories light-hearted, I have taken a socially n...

Trevor

by sub_nancy_cd on Sep 16, 2017
Transsexuals & Crossdressers

The phone must have rang about five times till my wife Kathy finally picked it up. I was busy finishing up the painting of the spare room and really couldn’t hear who she was talking too. I climbed back down the ladder when she came into the room. “I think I rented out the room” she said all smiles. “That’s great.” I smiled back as I put the paint brush do...

Beetlesmith's Ch. 25

by dresbach on Feb 5, 2018
Sci-Fi & Fantasy

Lost in a Roman...wilderness of pain, and all the children are insane. —The End by The Doors ******** I woke to the murmur of voices. The devotees and pain aficionados were starting to filter back into the Caligula Grotto. Stopping abruptly in her tracks, a pretty and voluptuous young blonde with shapely legs—and rump to match—caught sight of Gloria and...

One Night on Hedo Island

by silkstockingslover on May 15, 2019
Group Sex

Summary: Couple accidentally visits sex island and lets loose. Note 1: This is for a one-day author-themed event called ONE NIGHT IN.... Note 2: Thanks to Tex Beethoven, Robert & Wayne for editing. One Night on Hedo Island Fate is a funny thing. I mean before fate intervened in my life... I had no idea such places existed, and even if I had I wou...

Quiet Servitude Pt. 03

by AmandaMI on Sep 14, 2017
Transsexuals & Crossdressers

Author’s Notes Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions. To make the action flow more freely and the stories light-hearted, I have taken a socially n...

Click on Chat

by eightballbum on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: "Click on Chat" is an erotic thriller that touches on bondage, smoking fetish, cross dressing and other adult themes. As such it is intended only for mature readers. It is a total work of fiction and any similarities between the characters and actually persons living or dead is only by chance. Laws differ between states about what constitutes "ju...

The Looking Glass

by Son_of_Battles on Jun 15, 2020
Transgender & Crossdressers

This story contains Crossdressing, themes of Gender Fluidity, Exhibitionism, and Voyeurism. If any of this sounds unappealing to you, I welcome you to leave and find something more to your liking. This story is a submission for the 'Love The One You're With' Quarantine Story Event. Please take a second to rate after you finish reading. Thank you to Skye4Lif...

The Recovery Plan

by Purple_Raihne on Sep 16, 2017
Romance

Warning; This erotica has a lot of build-up, character development, and is an emotional roller-coaster based loosely on my own life. It contains themes and such that could be triggering to victims of physical and emotional trauma, and the sex is not til the end. Reader discretion advised. Hopefully, the wait is worth the ride. ************************* PRO...