Pegging Boy Stories

105,661 results
Orientation
Length
Source
Infinite Scroll

Belinda

by PaulSandarac on Sep 16, 2017
First Time

This story is inspired by, and dedicated to, a gifted young writer who posts under the tag "blin18". I would encourage my readers to take some time to enjoy her wonderfully creative, entertaining and sexy stories; and especially, (although not exclusively!), The Headmaster's Office 01, which gave me the idea for this particular tale, which is a tiny bit edgi...

Transformed Into A Shemale

by girlboybootsie on Sep 13, 2017
Fetish

I was 18 when I first had sex with a man. This is the story.... I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have be...

Steam Ch. 02

by axmanjack on Sep 13, 2017
Sci-Fi & Fantasy

Steam | Chapter Two | Departures Snow drifted in fat flakes from the sky, gathering into soft, cold piles that they marched through in lines. A geomagus led the procession slowly through the hip high drifts, holding his metal gloved hand out before him to feel for fissures beneath the endless field of white. The falling powder built up atop the shoulde...

Sweet Julie Birth of a Shemale

by tawnysuede on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions ce...

To Protect and Serve Ch. 05

by Evil Alpaca on Sep 26, 2017
Sci-Fi & Fantasy

Proofread by FernieLyn * This story is a bit wordy and fairly long, so if you are looking for immediate gratification, you might want to look elsewhere. The following story is a work of fiction. Any resemblance between these character and events and any real person or events is strictly coincidental . . . and pretty darn impressive seeing as it is a scien...

Happy Place Pt. 04

by Miguel59 on Sep 24, 2019
Loving Wives

Barbara's story. My gown has nothing to do with what I'm about to tell you. I'll save that story for another time. Those cotton panties, however, have everything to do with my story. Remember how I wore cotton panties when we first started dating and then one day I switched to sexy panties, the kind women wear. I'm getting ahead of myself. You've heard the...

Zydeco Coffee

by JimBob44 on Mar 25, 2019
Transgender & Crossdressers

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story has been edited by myself, utilizing Microsoft Spell-check. You have been forewarned; expect to find mistakes. *.* Martina 'Marty' Reffels parked her car in the students' parking lot of Hattie Caraway High School. The Myndee, Ark...

Being a Sissy for Viv Ch. 05

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

Mistress Viv wondered around the bed, filled with the most feminine and sissy items from my wardrobe. Her fingers stroking and examining various items in turn. The first things she picked up were some nylon panties. They were one of my earlier eBay purchases. A double layer of nylon ensured they always gave that nylon sliding on nylon feel even when worn on...

A Boy and His Genie Ch. 09

by DragoTime on Sep 25, 2017
Sci-Fi & Fantasy

Sophie woke up the next morning alone, which was something she'd long since decided she didn't like. She generally preferred to wake up cuddling with someone, whether it was Matt, Alexis, or someone else she'd commanded into bed with her. But this morning, she was alone. Matt was mad at her, she'd commanded Alexis to go back into her lamp, and she wasn't in...

Overseer of the Harem Ch. 03

by SexyGeek on Sep 19, 2017
Erotic Couplings

CHAPTER 3 --LESSONS Bagoas was a person of power. Physically powerful from exercise, which some of his peers neglected; mentally powerful from hard experience and long discipline; financially powerful, as shown by the gold coins jingling from his belt; and powerful in this place where he served the Governor of Ouarzazate in a high capacity. Bagoas was Over...