First Time Pegging Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Black On Black Pegging: True Love

by Samuelx on Sep 11, 2017
Fetish

I don't know why he thought I wouldn't be able to handle it. I really hope he'll stop hiding stuff from me after this experience. Female on male strap-on domination, Afro-Caribbean style. Seriously. I honestly wish he told me about this really hot fetish of his sooner. My name is Malinda Lexington and I'm a short-haired, green-eyed and kind of chubby young B...

The Best Present: Pegging my Man

by silkstockingslover on Sep 25, 2017
Fetish

Summary: A wife discovers her husband is curious about pegging and.... Note 1: This is a Holiday 2016 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, Dave and goamz86 for editing this story. The Best Present Ever: Pegging my Man I was working from home, stuck with a sick child, when my whole world changed. My work laptop died and...

My Shy Neighbour

by Ozgal on Sep 14, 2017
BDSM

Marty was such a sweet guy, but so painfully shy. He’d moved in next-door 3 months ago and in all that time had uttered no more than a couple of words and only when I spoke to him first. He had this cute little way of dipping his head into his shoulder and never making eye contact. Marty was quite a handsome man. He was about 6’ tall, with dark blonde hair...

My Shy Neighbor

by Ozgal2 on Sep 17, 2017
BDSM

Marty was such a sweet guy, but so painfully shy. He’d moved in next-door 3 months ago and in all that time had uttered no more than a couple of words and only when I spoke to him first. He had this cute little way of dipping his head into his shoulder and never making eye contact. Marty was quite a handsome man. He was about 6’ tall, with dark blonde hair...

Expanding Horizons

by JacobGoody on Sep 16, 2017
Fetish

Adam was cute from the minute I laid eyes on him at a friends party. Skinny and bearded he was a plaid wearing hipster kid holding his beer and listening to friends tell ridiculous stories about art school. He kept a smile on his face, and whenever there was a pause to drink, his eyes scanned the room, sometimes making contact with mine. Eventually that eve...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Dominatrix Gets Gang Banged!

by Samuelx on Sep 16, 2017
Interracial Love

Everyone's got that one fantasy that both excites and scares them. As a dominatrix, I make a lot of men and women's fantasies of dominance and submission come true. You name it, I've done it. Still, at the age of fifty one, I'd like to think that there are still quite a few things that I long to experience. I'm as human as you are, you know. I think even por...

I Want to Peg You

by pwlrstr on Sep 25, 2017
Fetish

I slip my hand around your waist and pull you into me, into a tight embrace. I'm wearing four inch heels, but you still stand a couple of inches taller than me, looking down into my gaze, an excited sparkle in your eyes. You run your hands through my hair, pushing it away from my face so you can see me better before coming in for a kiss. My hands run from yo...

All Girl's School: A Cunt Fest

by silkstockingslover on Jul 8, 2019
Illustrated

Editor's note: this story contains scenes of incest or incest content. Summary: A teacher's lez side is awakened by a hot teen. All characters in sexual situations are 18 years of age or older. Note 1: This is a Nude Day 2019 Contest story. Note 2: This story was inspired by this caption photo by @Mistressr3: At the top was the following text: Ever si...

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...