Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Swipe Right Ch. 03

by amb_anonymous on Jul 30, 2018
Transsexuals & Crossdressers

This story contains interracial, dom/sub, t-girls, crossdressing/sissification, impregnation and bondage. This story is fantasy. I like to stretch the limits of what's possible, so don't expect pure realism. For clarity: In my story, a t-girl is someone with a completely female appearance, but with male sex organs (so no hermaphrodites in the story). In...

Revenge!

by tawnysuede on Sep 14, 2017
Transsexuals & Crossdressers

Revenge! Or I Never Wanted This, but... Wow! By Mistress Tawny Suede ***** Chapter 1 Bobby Bradley knelt by the side of the road. He was mildly drunk and high from the first joint he had ever smoked. The cop leaned back against Elizabeth's sports car and took firm hold of Bobby's head. Bobby was afraid his blonde wig would come loose so he let his head...

Cracked Gemstones Ch. 01

by Artifal on Jul 13, 2020
Novels and Novellas

Sapphire was unpacking in her room, waiting to see what lesser being she would be stuck with for the duration of her time here. She was more than intelligent enough to do what she wished, but due to the systems in this country, she would have to have a 'degree' in order to be legally recognized at all. Sapphire soon heard the clicking of her door unlocking...

Dawg Origins: Chocolate Lavender

by mondotoken on Jul 31, 2018
First Time

Disclaimer: *All teen characters are eighteen years old, over the age of consent.* *** It all started out so innocently as my girl Edna and I were in the midst of some ill- advised sexual experimentation when we'd been caught by one of the church elders and outed to Pastor Grey. We were kissing, no tongue or anything when Sister Jacobs popped up in front o...

Filled with Joy

by BuckyDuckman on Sep 13, 2017
Fetish

Welcome to my Nude Day 2015 entry. It's a long one, so grab a beverage and maybe a sandwich before diving into it. This story includes graphic depictions of man-on-man sex as the hero wrestles with being a straight guy who enjoys sucking off other guys. There's lots of cumplay, a bit of humiliation, pegging by his girlfriend, and a very big piece of CFNM. If...

A Weekend Away

by amyredek on Sep 1, 2017
Group Sex

Along the High Street of Norwich there is a small book shop, not one such as W.H.Smith or Waterstone's, but more of the kind that they used to be when they first started out. It only has a small frontage and caters for the more astute connoisseur of first editions and those hard to find tomes of obscure writers as well as providing the service of finding out...

Blue Bloods Meet Castle Pt. 20

by baranbrat on Oct 15, 2018
Celebrities & Fan Fiction

One of my readers requested adding pictures of the new characters, but this is not allowed by Literotica. When a new character is introduced, I will put in parenthesis the character's real name so you can look them up on the internet. ***** Eric's head was spinning. He never, ever thought what Kate was suggesting would fall in his lap. This all along was...

The Corner Table at Mickey's Pt. 04

by chasten on Sep 28, 2020
Romance

This is the finale of the story. I apologize, but this part is longer than the first three. I had originally intended to split the story into five parts, but I couldn't find a good point where the events had a natural divide and the last two sections would be roughly of equal length. Rather than pick an artificial split and leave everyone off-balance, I dec...

The Craziest Sexy Love Story Ever

by silkstockingslover on Sep 13, 2017
Anal

Summary: Straight white, black stud, cheerleader, nerd & submission Note 1: Although a rather unorthodox love story...this is a Valentine's Day 2014 Contest Entry because I wanted to try something different and because I believe love can occur in so many ways. Note 2: Choosing a category for this story was a struggle as the more I wrote the more the st...

A Lost Lover, Changes for Melissa Pt. 01-02

by MadQuill on Feb 6, 2018
Transsexuals & Crossdressers

Please remember this is a copyrighted work and all legal disclaimers apply. I appreciate the editing assistance of Santacruzman. There is an inspiration for this tale and the character Thom in the film directed by Jean Negulesco: "How to Marry a Millionaire". I love the three women characters, Shatze, Pola and Loco and their manipulations. This tale does NO...