Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Long Haul Ch. 03

by AwkwardMD on Sep 21, 2020
Sci-Fi & Fantasy

//Author's Note: Huge thanks to my good friends KatieTay and SkullTitti for their help in translations and tone! This story could not have been possible without their patience and assistance! All characters are 18 or older.// "Here we go," Wren whispered, as the timer counted down and the Daedalus dropped out of t-space. The disorientation passed quickly,...

A Boiled Frog Pt. 03

by noobdude on Sep 18, 2017
Transsexuals & Crossdressers

Welcome to 'A Boiled Frog'. If you haven't read Parts 1-2 I suggest you read those first as the characters and situations won't make much sense otherwise. Please vote, I especially like feedback and comments, both good and bad, as this is my first storytelling experience and any help I get is appreciated. Special thanks go to Anjali and Sterenn for editing...

Damsel in Distress

by luk77 on Oct 31, 2018
Transgender & Crossdressers

Edward Marston was tired. It had been a long few days. It was Friday and he was looking forward to an easy weekend. He had nothing planned. He had stood in line at the cellphone provider and managed to change his contract. He needed to remove Lisa, his ex-wife, from all his bank accounts, credit cards and mobile phone contract. This took more time than he an...

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Julia, Ben and Lisa Ch. 09

by chloejacobs83 on Mar 10, 2020
Transgender & Crossdressers

Ch 09: Wednesday A few quick notes: 1. this is the ninth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned We were both quiet and shy the next morning. How do you start after...

Married at First Sight

by komrad1156 on Oct 15, 2017
Fetish

*Note to readers: This story is about the fetish of attractive women who smoke. If you hate smoking, please move on to another story. Don't bother telling me about your poor Aunt Millie who died of lung cancer or your Uncle Joe who has emphysema from smoking as it won't change the way I feel one iota. We all die from something. **Intro: My girlfriend, Kay,...

A Boiled Frog Pt. 01

by noobdude on Sep 25, 2017
Transsexuals & Crossdressers

Author's Note: After three months of trying to find an editor or get some feedback, I'm giving up and will just post my story and see if I can get any feedback to help it out. It's my first attempt at writing a story and I know it needs work, so please be kind. Any helpful feedback is appreciated. ***** Chapter 1 With the last pass over my lips with a...

Kinky Virgins: Feminization

by SubtleDeviance on Apr 18, 2018
Transsexuals & Crossdressers

Characters are at least 18. The title is kind of a misnomer at this point. Probably should have thought that through. Also, mind the tags. This story has cross dressing, feminization, snowballing, and pegging. If that's not your thing you might want to skip this one. ***** "Good morning, cupcake," Renee whispered as she awoke and gave Chris a sweet littl...

Black Cock Worship: A Woman’s Fall

by silkstockingslover on Jun 19, 2018
Interracial Love

Summary: White wife is drawn into world of kinky submission. This is not really a sequel, but a slightly dove-tailed story of how, in the wake of her husband's fall, the wife also falls and ends up addicted to black cock. If you want to read the husband's fall read: Black Cock Worship: A Man's Fall. Dedicated to the real Christine and Ken, as this is based...