Pegging Sissy Stories

7,509 results
Orientation
Length
Source
Infinite Scroll

Shooting The Moon Ch. 04

by SEVERUSMAX on Nov 8, 2017
BDSM

"So, that's it. The new contract for Robert and me in our new life of bondage to you. I rather like it, in fact. It's making me wet, just thinking of how much we're both your sluts now. My hubby and I. We belong to you for life, by our own agreement. We will gladly serve you, as this contract stipulates, Master," Lindsay assured me, her silky hands caressing...

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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Your Adventures in Mixed Wrestling

by EugPad21 on Nov 20, 2020
Fetish

You walk through the doors. Excited to begin your first day as part of the Mixed Wrestling Federation. You walk up to the desk where a receptionist is waiting for you. "Hello, How can I help?" She asks "Hi my name is (Insert your name). I'm here for to sign up for the Mixed Wrestling Federation" "Ahhh yes" she said, "We got...

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Pegging Fantasies

by the_shires on Sep 25, 2017
Fetish

Alan looked over at Jill. As usual her face was buried deep in a stack of books. Not one book, or even two. At least four. She was studying for her exams, and her face showed intense concentration. He sighed. They had a matter of weeks left before they were out of college and working full-time jobs. There was a lot of anxiety written around them and he knew...

A Whole Lotta Domme

by MsTrina on Sep 18, 2017
BDSM

Confessions of a Dominant BBW... Being a 'big' girl in today's street parlance usually refers to the bra size one looks for in Marks and Spencer. But I've always been a 'big girl' -- since even before my mammaries started developing into the super-size jugs they are now. It wasn't that I ate too much -- it just seemed that was how I was meant to be. My gra...

Somali Queen In Ottawa Ch. 05

by Samuelx on Sep 12, 2017
Fetish

The things I do for love never cease to amaze me, ladies and gentlemen. The other day, after a night of passion, I tossed my girlfriend Yasmin Hussein my house keys, mainly because I wanted more access to her pussy, and the sexy Somali chick got it into her Hijab-wrapped head that I wanted her to move in with me. I was terrified of Yasmin moving in with me b...

Interracial Pegging : Amen!

by Samuelx on Sep 11, 2017
Interracial Love

Hey, there. My name is Barry Etienne. A big and tall young Black man of Haitian descent living in the City of Nepean, Province of Ontario. And for the longest time, I've been desperately lonely. Almost to the point of wishing my existence would end. My life seemed that dull, man. I felt like I had nothing real going on. From my classes at Carleton University...

White Women Got Big Dicks Too

by Samuelx on Sep 17, 2017
BDSM

My name is Susan Edgar. I'm a six-foot-tall, blonde-haired, green-eyed, forty-something Irishwoman living in Boston. I'm happily married to Stuart Lemond, a tall and good-looking, red-haired gentleman of French-Canadian descent. Lately, our relationship has been rocky. Partly because the passion is gone. So, we decided to spice things up. Bringing new people...

Be Careful What You Wish For

by ChainedToAKeyboard on May 12, 2020
Fetish

Author's note: This short story was inspired by Vitalis' amazing hentai artwork: "Bimbo Catalog: Bianca." * It was date night in the Whitley household and things were just starting to get exciting. Alice and Richard had enjoyed a lovely meal at a five star restaurant, a wonderful performance at the theater and a couple glasses of fine wine upon returning h...

Cucked Up Pt. 01

by DandJ69 on Jun 1, 2020
Fetish

"I've been fucking your wife for the last three months, and she fucking loves it!" Came the shocking confession from one of my oldest friends, Steve. "Fuck you... You're lying." I replied. "Oh yeah... Then whats this?" He snarled, showing me his phone. I looked down to see several messages between him and my wife. I only read the last couple, which wer...