First Time Pegging Stories

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Pequeñas y Humillantes Historias

by 57 on Jun 7, 2020
Miscellaneous

Primero que nada me presento. Soy Guillermo, y tengo 25 años de edad. Además, como descubrirán en las historias que les voy a contar a continuación, tengo el pene pequeño. 10 cm flácido, 12 cm erecto. Es así. Ya lo acepté. Que lo haya aceptado, no quiere decir que no me avergüenza el hecho de ser objeto de burlas por parte de otras personas. Pero creo que ha...

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A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

A New Beginning

by DutchAlex on Oct 30, 2018
Fetish

Carla sat in her car in the parking lot of the sex shop. Staring at the front door and working up the courage to go inside. The Fantasy Adult Fun store had just opened a week ago, but she had been thinking about this moment for a long time. Ever since she found out Jim had been cheating, through the divorce, and the year between then and now. It hit her ha...

Creampies, Pegging & Intimacy

by Here4u2get on Nov 18, 2019
Erotic Couplings

I had to laugh when I heard the music playing and the shower running behind the door of the master bathroom. Dana, my wife, apparently had the same plan as I did about getting ready early that Saturday evening before we met her girlfriend and husband for dinner. Yes, she wanted to see as much of the football game as she could before we had to leave. Though...

Israeli Femdom 4 Muslim Slaves

by Samuelx on Sep 11, 2017
Interracial Love

You've been a naughty guy, I told Rahim Abdullah as I spread his dark butt cheeks and eased my strap-on dildo into his asshole. Immediately the young Somali man went stiff, as something I call the shock of penetration came over him. It happens with every new submissive who experiences the joys of pegging for the first time. Gripping his narrow hips tightly,...

Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Biracial Somali Dominatrix

by Samuelx on Sep 17, 2017
BDSM

Muslim women are supposed to be boring, dull and repressed, that's what a lot of otherwise intelligent people believe. My name is Mariam Jabari and I'm here to refute these absolutely false claims. I was born in the City of Ottawa, Ontario, to a Somali immigrant father, Ahmed Jabari, and a white Canadian mother, Marilyn Samson. I am the daughter of two very...

Interracial Pegging: Female Giant

by Samuelx on Sep 11, 2017
Interracial Love

Why is everyone so damn afraid of interracial pegging? That's what I want to know! My name is Beatrice Levin. A six-foot-eight, red-haired and green-eyed French Canadian woman living in the City of Ottawa, Province of Ontario. Folks, I am a big woman. And I know it. I'm damn near seven feet tall and weigh two hundred and eighty pounds. I was afflicted with g...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...