Pegging Sissy Stories

7,509 results
Orientation
Length
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Infinite Scroll

Sam's Story Pt. 09

by Shadykingcolor on Jul 6, 2020
Fetish

As I sat in the basement...the dungeon, contemplating my new life as "Trisha." Mel's anger. She knows about Cassie. How my life is forever changed, I ask myself "was it worth it?" The door creaks open. Someone begins to descend down the stairs. It's Cassie, holding a cup and saucer. "Tut tut tut, Pet. Who's been a naughty little sissyboi." She purrs while...

A Big Surprise!

by rj1774 on Jul 6, 2020
Transgender & Crossdressers

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy! **************** My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get a...

Getting to Know Me

by TheOriginalAnonymous on Sep 16, 2017
Reviews & Essays

My thoughts on sexuality, porn, and what makes a man **************************************** Some people subscribe to the belief that women are degraded in porn; these people think porn is sexist. In my opinion this is bullshit.* Some people enjoy being used when it comes to sex; I don't think there's anything wrong with that. Being submissive sexually, b...

How I Experienced Her Strap On

by LeashedMale on Sep 13, 2017
BDSM

She was teasing me constantly for over a month. I was already experiencing other forms of female dominance, such as being smothered on a regular bases and being required to give her oral sex all the time. With my cock under lock and key, anything and everthing she said and did was making me feel extremely submissive to her, and extremely frustrated. She cal...

A Small Problem

by Rbhy2 on Mar 2, 2019
Cheating Spouses

"Hey baby I'm home" you said as you walked into you apartment. The building wasnt much, just an old converted motel that you and your girlfriend Kay had scraped enough money together from your menial, part time jobs to afford. "Hey babe I'm in the shower" you hear coming from the bathroom on the back. "I'll be out in a sec" You...

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The Captive Prince

by PrinceCai on Apr 3, 2020
Fantasy

Marcus was reading in bed when his kingdom fell. It was over an hour past his bedtime, but the young prince wanted to stay up and finish his book by candelight. It was way too exciting a story to put down, all about a brave and noble lady knight who saved a peasant boy from the clutches of an evil sorceress. He had his heart in his mouth at the thrilling act...

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Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...