Sissy Stories

6,529 results
Orientation
Length
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Infinite Scroll

Put It In Writing!

by maninconn on Sep 14, 2017
Loving Wives

"But honey, trust me. It's going to be so fun, so sexy, I know you're going to love it. Do this one thing for me just because you love me. You do love me, right?" There it was. The "if you love me you'll_________" trap. Fill in that blank as you see fit. Do the ridiculous honey-do list on what should be a restful Saturday afternoon. Learn to waltz. Spend th...

My Life as a Cuckold

by CuckoldGuy on Sep 16, 2017
Reviews & Essays

A True Story After the first year of marriage, my wife began an affair with her manager. He was the first of many men over the years. Some of them I knew about and I may have even encouraged them but most were done behind my back, in secret. Because she has these secrets, not a day goes by that it doesn't play on my mind. One day in my angst, I typed the wo...

Entertaining is Hard Work!

by Jemina004 on Apr 10, 2018
Transsexuals & Crossdressers

Dani had placed the large bowl of tortilla chips in the middle of the table and stepped back to admire the effect. The bowls of pretzels, chips and various dips were artfully arranged to his eyes, but Dani knew he was wasting his time. Between the NBA game on Keyshawn's huge TV and what Dani was wearing, the soon-to-arrive guests wouldn't care too much about...

Ægir's Wife Ch. 09

by Tara_Neale on Sep 18, 2017
BDSM

Kirsty stared out over the relatively smooth waters of the North Sea. Even though it was after ten, the sun had still not fully set this far north. Was it prophetic somehow? When she had left all those months ago, it had been dark almost all day and night. Now at the height of summer it was just the opposite. Almost constant sunlight. It certainly felt lik...

Queen of Paradise Ch. 03

by ptpl_guy on Nov 2, 2017
Transsexuals & Crossdressers

This is a work of fiction. Names, characters, businesses, places, events, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. ***** Michele stepped off the elevator and headed down the hall toward his and his wife's suit...

Weekend Two

by TJones28 on Oct 14, 2017
Erotic Couplings

Second Weekend This is Part 2. You may read this as a stand-alone piece, or you may read Weekend One First. * I sat in front of a monitor watching a film about a kid about to burn his house down. The camera crew set up the shot of him lighting a match and staring at it, wide-eyed. I had a script in front of me with marks all over it and scribbled notes on...

Anthony's Descent Ch. 01: Truth or Dare

by SissyKaty on Aug 21, 2018
Transsexuals & Crossdressers

I was hanging out with my girlfriend Katie in the basement of my parents' house. We had been dating for about 2 years, we were both currently 18 years old and seniors in high school. I was 5'6" tall with olive skin, I'm skinny with a little lean muscle built from playing various sports in high school. I had a 3.5" inch cock fully hard that I was extremely em...

I Hit a Grand Slam in Seattle!

by TheBusinessMan on Aug 22, 2018
Erotic Couplings

This is an adult sex story; all the characters are of the age of consent or older. Please read my previous story "Why I Eat a Lot of Pussy" for background. Thanks for your views and votes. **** It was Friday night in Seattle. January. We had flown up the evening before from Los Angeles, first landing to drop off Catherine's daughters in Vancouver so t...

The Massage Away Ch. 02 Pt. 03-04

by formyqueenspleasure on Aug 20, 2018
Fetish

Fair Warning 1 - I am a first time writer Fair Warning 2 - this story involves Femdom, a wife, cross dressing, sissy husband, interracial, group sex and obviously may not be everyone's cup of tea (but I hope it is appealing to some comfortable fetishists!) This chapter moves into the themes. Fair Warning #3 - If you don't like a sick depraved story, don'...

Ms. Rhonda's Finishing School Ch. 01

by hollygurl29 on Aug 21, 2018
Transsexuals & Crossdressers

DISCLAIMER: All characters in this and any additional parts of this story are all over the age of 21. This tale involved crossdressing and BDSM. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. If you choose to read this tale then I thank you in advance for doing so. When you have finish...