Pegging Sissy Stories

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Orientation
Length
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Infinite Scroll

The Guestroom Session 01

by EyesNotOpen on Sep 25, 2017
Fetish

I heard the door open, and I knew who it had to be. "Aww, look at you honey! You're doing so well tonight!" Her voice was soothing, slightly mocking of me, but exactly what I needed to hear. "How long so far?" she asked. I of course could not answer her. Nor could I see her. I was on all fours, blindfolded, with a cock-shaped gag strapped into my mouth. "...

Venus Trader

by skinnysailor on Oct 24, 2018
Transgender & Crossdressers

It's Oh Five Thirty aboard the seven hundred foot container ship 'Venus Trader' Twelve days out of New Orleans towards the Suez. It'll soon be time to get out of bed and fetch the Captain's breakfast. I'll lie in for a bit longer. I hear the door for the head open and close. I feel the bunk as Captain crawls in beside me. I pretend to be asleep. Our little m...

Black on Black Pegging is Okay

by Samuelx on Sep 11, 2017
Erotic Couplings

Romulus Stephen sat in his bedroom in the small apartment overlooking The Park in Vanier, around the eastern bend of metropolitan Ottawa, Province of Ontario. The big and tall young Black man sat at the computer with his pants down, and furiously stroked his dick. On screen, a sexy Black woman was banging a slim White guy in the ass with her strap-on dildo....

Cissy's Pegging Parlour

by Pinkmanties on Mar 18, 2020
Fetish

Fella's are you looking for a little backdoor action? Maybe you want those cheeks to feel the sting of a riding crop, or you want your boipussy filled with a firm supple dildo, or maybe you're just looking for a girl who will put your manclitty in a cage and tell you what a bad boy you've been! Come on down to Cissy's Pegging Parlour where your dreams become...

Afrocentric Femdom for Black Men

by Samuelx on May 30, 2018
BDSM

You are tantalized by my presence, a curvy Black woman with a thick Afro and a big beautiful Black ass, standing decked out in shiny Black leather in front of you. I've been told I have quite the presence. What's my name? You are mystified by me. No names. Does it matter? Not at all. I am your Black Mistress, and I've come to fuck the hell out of you and dom...

Assuming Ownership

by uwillsqueel4me on Sep 28, 2020
Fetish

My Domme has instructed me to write this brief story about how she (formerly my wife and legally still) decided she had had enough of being in a traditional marriage with a "normal" guy and decided that she was going to take over - once and for all and absolutely. I can personally vouch for the effectiveness of this approach and although it may not work for...

Bill Meets Jessica Ch. 05

by lateknew on Mar 2, 2020
Fetish

I woke up, Jess had showered, dressed and having a coffee, she looked nice, cute, sexy. "Alexa, did you sleep well?" Jess asked. "Yes Jess." and joined her with a coffee. "Have to run some errands, you?" Jess asked. "I've got some work to do from home, a meeting and then I'm free and maybe for the remainder of the week." I said. "Would you like to have...

Discovering Mistress Sarah's World Pt. 08

by oneguy4fun on Sep 14, 2017
Transsexuals & Crossdressers

Part 8 -- Complete Surrender Chapter 21 Leaving Behind Joe's Life Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs. "I'm sending May with you Josie," announced Mistr...

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...