Shemale Pegging Stories

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Orientation
Length
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Infinite Scroll

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...

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...

Awakening: 7 Slutty Blackmail Tasks

by silkstockingslover on Mar 20, 2018
Illustrated

Summary: MILF's sexual awakening by being forced to do 7 slutty tasks. Note 1: This is an April Fool's Day 2018 Contest Story so please vote. Note 2: Thanks to DARKBREEZLY for collaborating with me and creating all the illustrations that bring this story to life. Note 3: Thanks to: Tex Beethoven, thor_p, Robert, and Wayne for editing. Note 4: A warning:...

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...

Born to Be Ch. 02

by DamienDeath20 on Apr 23, 2019
Transgender & Crossdressers

A.N. A CHAPTAH TWOOOOO Fun times up ahead :3 the world has been kicking my ass with trying to keep up with my projects, but I'm powering through as best I can. The Following Contains: Femboy with tall black babe fucking him up the butt with a strap-on. *cries it's not futa* Lol, also in this chapter, we begin the process of feminizing our pretty protagon...