Sissy Butt Plug Stories

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Orientation
Length
Source
Infinite Scroll

A New Adventure... Ch. 02

by johnjinglez1 on Jun 6, 2018
Transsexuals & Crossdressers

This is a continuation of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. *** After my first three encounters with TS and CD's left me feeling unfulfilled I gave it up for a few months and figured it just wasn't for me; I went back to having sex with...

True Desires Unleashed Pt. 03

by CuckedbyBBC on Jul 18, 2018
Interracial Love

When Robert left I wanted to talk to Alice. That had been the most exhilarating experience of my life but I wanted to make sure she was okay. I mean Jamaican gangsters are on their way to possibly take her anal virginity and she just her insides torn apart by Robert's huge cock. We had so much to talk about but she was smiling and seemed okay, and all she sa...

Kasey's Confession Ch. 08

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

I woke up the next morning feeling incredibly sore all over. I was lying on the couch in Mr. Smith's living room, covered up with a blanket, with only vague memories of what had happened after Mr. Smith finished fucking me. I knew Pedro and Jake had taken turns with me as I had flashes of memory, almost like photographs, of them putting me in different posit...

CFnm Adventure - 2nd Visit

by lovelicker99 on Sep 13, 2017
Fetish

Note: This is the second story involving encounters between me as a submissive male and a Dominant BBW who responded to an ad I ran online. These stories are fantasies, but some of the specific acts are things I have done and enjoy doing. If you are a woman or a couple that enjoys doing any of these things I would like to hear from you regardless of where yo...

Spice

by AfroerotiK on Sep 17, 2017
BDSM

It was with some frequency that James Hartman returned to his old stomping grounds in the ATL for job related responsibilities. Atlanta held many memories for James, good times, pleasant reflections and melancholy longings. It was a trip he always took with much anticipation because it presented itself with the hope of exploring his deepest, darkest, most pe...

Big Black Bike Club Ch. 02

by ThePiperRai on Jan 29, 2020
Interracial Love

"You doing alright?" Flint asked with a harsh laugh. He ashed off the cigarette and walked over to me. I was still laying on in the dirt and leaves, playing absentmindedly with the cum pooling on my body. "Yeah..." I managed, still basking in the afterglow. I was trying to remain there. Remain in the moment. I knew that when it faded, when I returned to...

The Audition

by bitomah33 on May 7, 2019
BDSM

His heart was beating so hard inside of his chest that he could no longer think clearly. He just realized they really did not plan out this scene ahead of time. He was so drawn to her energy that most of his rules regarding safety were ignored. For some strange reason he trusted this stranger, as if they were intimately involved in a former life. He was begi...

Freyja Inc. Ch. 05

by Texas_law_man on Sep 15, 2017
Anal

Chapter Five Elimination Over the last week Shea's day was very structured with little deviation. At six thirty every morning Wesley would wake her and allow her to remove the plug from her ass in private. By now Shea had moved to a larger plug so it was slightly more uncomfortable walking early in the morning. After a quick shower breakfast was served then...

What's in my ass?

by alternatereality08 on Jan 1, 2018
Fetish

A/N: This is a fun/dumb story that shouldn't really be taken too seriously. Edit: I made some edits to the story in order to make it make a little more sense. Edit 2: I made some changes to the premise to allow for more options and interesting plotlines. In a world similar to ours, a strange law has been passed: women can't wear anything on their lower half,...

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The Virgin Tranny & the Bride Ch. 03

by yano on Sep 25, 2017
Transsexuals & Crossdressers

My transvestite friend Roberta continues her true tale of transformation and dominance from her bisexual neighbours' as she becomes a form of sex slave both in the privacy of their home and also on the streets. Initially attracted to Margaret and her sexy underwear Roberts' secret was discovered by sex starved Margaret. She dressed in her bridal gown for hi...