Pegging Sissy Stories

7,509 results
Orientation
Length
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Infinite Scroll

Appointment by Card Only Ch. 01

by Sputnik57 on Sep 17, 2017
BDSM

She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The...

The Making of a Mistress Pt. 04

by EiryCGar on Jul 13, 2020
BDSM

Author's note: The saga of Mistress-in-Training Marie and her sissy Charles has reached the point of their marriage. After the ceremony, Marie achieves her ambition and becomes a hotwife, making Charles a cuckold in the process As in all my fictional stories, all characters are over the age of eighteen, and all sexual practices described are performed conse...

Down Under Dee

by SEVERUSMAX on Sep 17, 2017
Loving Wives

I sat down at my usual stool at Kieran's, an Irish style pub in my neighborhood, and I naturally expected to order my usual Harp's or Guinness, from my usual bartender, Kevin Murtaugh, a gruff, but otherwise likeable fellow always willing to lend an ear. That was not what happened, of course, or there wouldn't be a story to tell. At any rate, there I was, wa...

His First Taste of the Real Thing

by 2easy2 on Sep 19, 2017
Fetish

My girlfriend, Angie, has been dressing me in women's lingerie and pegging me with her strap on dildo for a couple years now. It started with an occasional pair of satin panties and quickly moved to sexy little nighties, stockings and painted toenails. As bad as I hate to admit it, I absolutely love it. It's all I think about anymore. I love the submissive...

Futa: The Emergence

by Smithjohnsonian on Dec 13, 2018
Fantasy

Earth witnessed a massive meteor shower in 1950 which brought along with it extraterrestrial life, albeit as unicellular organisms, several of which crashed as meteorites in Central Asian, East Asian and South Asian countries with a few of them landing in the North and the South Americas. These single-celled organisms had a lot of similarities with viruses o...

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Discovering Mistress Sarah's World

by oneguy4fun on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 1: Meeting Mistress Sarah Joe's heart pounded fiercely as he stood at the door to his Mistress's house. He did not expect to be so nervous at his first meeting with her. After all he had known her for over a year. Mistress Sarah had been gracious enough to allow him into her world. He was fortunate to fall under the control of such a beautiful domin...

Becoming CD Mistress Raven's Slut

by Vodka_Jim on Nov 19, 2018
Transgender & Crossdressers

**Author's Note: This story is very kinky. It has a lot of BDSM and is about a straight guy having an encounter with a cross-dressing dominatrix. It's definitely not for everyone. Hell, it might not be for anyone. But hopefully a couple of you will enjoy it. All comments are welcomed. VJ** ***** Kevin looked at me and just shook his head. "You gotta snap o...

Mistress Wahidat Of Somalia

by Samuelx on Sep 17, 2017
BDSM

Sliding my strap-on dildo into Malik Clarkson's ass, I smiled with utmost satisfaction. I had him right where I wanted him. Face down and ass up, that's the way I like to fuck my men. In case you're wondering who this is, my name is Wahidat Suleiman and I'm a young Black woman of Somali descent living in the City of Toronto, Ontario. I'm five-foot-six, slim...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Black on Black Pegging in Canada

by Samuelx on Sep 11, 2017
Fetish

Hello, there. My name is Linda Lasalle. I'm a young Black woman of Haitian descent living in the City of Ottawa, Province of Ontario. I was born and raised in the City of Cap-Haitien, Northern Haiti. I've been living in the Confederation of Canada since 2010. Ladies, I got a wickedly interesting story to share with you. It took place during the fall of 2011....