Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Interracial Pegging: Revenge

by Samuelx on Sep 11, 2017
Interracial Love

Bad company. That's what everybody says about me behind my back. And to be honest, I don't give a flying fuck. My name is Julianna McCain. A six-foot-tall, slender and athletic, red-haired and green-eyed young woman of English descent living in the City of Ottawa, Province of Ontario. And I am a Canadian porn star with a unique specialty. I am really into In...

Domestic Goddess Ch. 01

by mstqfox on Sep 13, 2017
BDSM

Jack stood naked in the bathroom doorway. It was 7 a.m. Saturday morning, and he had just finished depilating his body from the waist down, as I had instructed him. "Looking good, honey. Nice and smooth," I said. I motioned him towards the bed. We had a rustic king-size bed, the legs of which were made of polished 8-inch thick logs. The headboard consisted...

Coffee

by Wes7 on Sep 12, 2017
Fetish

My sweetie is an Internet wiz. She finds the best shopping coupons and bargains, books and movies we'll both enjoy and once in awhile, something a little different. For instance. This is about "pegging." How many of you know what that is? I'm an experienced man and I thought I knew everything there was to know about sex. I was so wrong. We're a normal coup...

Journal Beginning

by Tripx713 on Jan 22, 2020
Reviews & Essays

My previous blogging on unnamed sites has been of several types of posts. As this title suggests, I've created journal entries which have been quite popular. I've also written many fictional stories across a range of erotic genres: sci-fi, coercion, polyamorous relationships, cheating, human furniture, gender modification (by magical, chemical or alien means...

Jason's Secrets Exposed Ch. 09

by jlenil on Sep 14, 2017
BDSM

I suggest that the reader check out the first parts of this story before reading. Comments are appreciated. ***** The following morning, I awoke at 6 AM with a raging clitoral erection, having been dreaming about pegging Jason with other people watching. I summoned Jason from his spot at the bedside and told him to lick me. He did so, much to my satisfacti...

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

Open in Reader

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Interracial Pegging Chronicles

by Samuelx on Mar 6, 2018
Interracial Love

Donna Baker, better known by her porn moniker Silver Thorne, carefully looked at the young African American man who sat less than a meter from her. Conducting interviews with new talent in her small, Spartan office was one of Donna Baker's many duties as the CEO of a major adult film company. Sure, the human resources department could have taken care of that...

Made to Obey Ch. 09

by madetoobey on Jul 30, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a daily event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shemale...