Pegging Sissy Stories

7,509 results
Orientation
Length
Source
Infinite Scroll

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

Open in Reader

Long Road Pt. 02 - Self-care

by Henriette7 on Mar 30, 2020
BDSM

It has been two days since my first real play-session with my girlfriend. And oh my, was it two very long days since then. My hope that living my fantasy would reduce my horniness and leave me free to think about other stuff was absolutely crushed. I couldn't stop thinking about it, about her. About her thighs, the change of her tone when she commanded me, t...

Discovering Mistress Sarah's World Pt. 02

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!" "I think someone is excited to see you," laughed Mistres...

Mistress Tanya Ch. 01

by Palancar on Sep 18, 2017
Fetish

This is the first chapter and is a little tedious without any actual sexual situations. Please bear with it. I needed this to set the stage for following chapters. I promise it will get much better. Also please remember it is only a work of fiction. I welcome critiques both good and bad but if the storyline isn't your cup of tea then don't read it. I see s...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

Open in Reader

Black Lady Cuckolding Black Guys

by Samuelx on Sep 17, 2017
BDSM

Salutations, sluts, bitches and pigs. This is Mistress Yasmina Hussein, a happily divorced Somali-Canadian woman living in the City of Ottawa, Ontario. I've been dabbling in the realm of BDSM for a while and I've gotten quite good at it. What can I say? I like to dominate both men and women, especially people of color. Black on Black BDSM and Kink are suprem...

After Flowers

by ilovebananas on Mar 30, 2020
Transgender & Crossdressers

It was springtime in the garden of Eden. Garrett and I never had a perfect relationship. It was awkward at the start before the curve flattened. The honesty came later with middle age. Ever since we attended a birthday party celebrating my best friend's birthday, our love life had gone through the roof. I am not one to gloat, but it proved many people wrong....

Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

Open in Reader

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

The Researcher Ch. 07

by MadQuill on Feb 12, 2019
Transgender & Crossdressers

This is a story I began in January, three years ago. The plot evolved as I finished the third chapter and the scenes and details of each chapter have required more time than I anticipated. The curve of the plot shifted towards the couple, Maris and Jon (aka serge). This chapter was posted in Erotic Couplings, but due to the plot progression it is posted as T...