Sissy Anal Captions Stories

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Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Exploring My Fetish

by fetishguy81 on Jan 7, 2018
Anal

Note: This story plays off of my previous 2, taking place after both of them. You won't miss too much but you can get more of the backstory by reading my other 2 stories first. ***** I developed to rather uncommon fetish's in pretty uncommon ways through out my life. My first was a fetish around salon capes and haircuts in general. When I was younger I dre...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

Cuckold in Training

by BBCXXX on Sep 24, 2018
Interracial Love

I was a stunned by my discovery! My husband Tony was out of town for a few days on business and I needed a tool from his workroom. While digging through one of the tool drawers I found a small, portable hard drive. "Why would this be in here?" I thought, but then the little voice inside my head started to scream, "Put it back you fool! Don't look inside; you...

Cuck Ch. 01

by putmeinpink on Sep 14, 2020
Fetish

When the front door finally opened, I lay motionless. Of course I had heard the car pull up and the door as it shut. I waited, bristling with anxiety, as I hung on every stray sound, any slight indication of what she was doing as she entered the house. 5:13 in the morning the clock said in stark red lines. My brain screamed as I recognized each sound, catalo...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

Boredom and Therapy

by oldhippie1949 on Aug 31, 2017
Group Sex

The following is a true story. Naturally, all the names have been changed but all the events described took place just as I have written. If a bi-sexual threesome is not to your tastes then move on. If you are too young to be reading this, then move on. ***** I was so bored. Even my dog couldn't shake me out of it and. believe me, he tried. I didn't care t...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Loosening Up Bk. 01 Ch. 01-10

by SteveWallace on May 14, 2018
Group Sex

Book 1 -- Loosening Up: Initial Journey Chapter 1 -- A Crack In The Façade Alice sedately drove her seven-year old silver Honda Civic into the parking lot of the company she worked for -- Knightsbridge Manufacturing. She looked around, but only a few cars were present. Along the back side of the lot four cars were already parked in the spaces under the tre...