Sissy Sex 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...

A Deal Offered

by LockedSissySubmissive on Sep 25, 2017
Fetish

I was sitting in the kitchen drinking coffee wearing my dressing gown when Emma left for work. We'd had a pleasant morning chatting about the various inconsequential matters that married people chat about but she had to leave for a meeting and looked fabulous in a smart dress suit and jacket. Even after almost two years of marriage I was still totally smitte...

Mistress Monique

by bleedndkn on Sep 25, 2017
Fetish

I met Monique at a show. She wore a tight black dress, dark eyeshadow and was by far the hottest girl at the venue. I didn't have a chance. A mutual friend introduced us and I became immediately enraptured with her and in the days to come would constantly think about how to spend more time with her. Then, after an evening with Monique and mutual friends at...

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...

Indoctrination - Potluck

by cuck4Traci on Sep 25, 2017
Fetish

"Mmmmmm," I stretched as I woke happily naked in bed. The sun was just peeking over the mountains and the soft light shone through the bedroom window, bathing the room with a summer glow. I love this time of year when nights are warm enough that we can sleep with the windows open and smell the crispness of the early morning. Somewhere out there a lone meadow...

The Conditioning

by wifeownseverything on Sep 17, 2017
BDSM

This story contains female domination, verbal degradation and humiliation, and perceived exploitation. Both characters are consensual adults. Please skip if these subjects offend you. ***** This is the fourth story I've written about my wife and myself. It is the only story that isn't mostly true. While fantasy in the sense that it hasn't happened, I thin...

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...

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...

Mitzi Seduces Mrs. Robinson

by Tcs1956 on Sep 13, 2017
Exhibitionist & Voyeur

***** I think it must have been some kind of temporary insanity. What other way is there to explain where I found myself that day? Driving in my car, naked from the waist down, not knowing exactly what was going to happen when I reached the address that was written on the paper lying on the seat between my bare legs. One thing I was sure about—the arousal...