Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

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...

Forced Strapon

by trypewyre on Sep 12, 2017
Fetish

One weekend while sitting back in my chair, I was watching a movie. My mind started to wonder when I drifted off to sleep. I awoke a couple hours later to a touch on my shoulder. Knowing it was my kinky redhead girlfriend, I thought nothing of it when I drifted back asleep. A few seconds later I felt a hand slowly move down my chest and stopped on my flaccid...

Moving to the Sexworld

by Shendude on Dec 19, 2010
Science Fiction

Imagine an alternate universe where casual & free sex, sexuality, & nudity are everywhere, where all people are at least bi, where there are almost no sexual taboos, where everyone's a nympho or satyriac, and where almost all interpersonal interactions have some form of sexual content, and it has ALWAYS been this way. Now, imagine that this world com...

Open in Reader

Brittany's Strapon Hell Week 03

by humbleslave on Sep 11, 2017
Celebrities & Fan Fiction

Brittany's Strapon Hell Week 3: "Fear with Jenna and Vanessa" I am attempting to make these stories stand-alone as well as make sense in a series. If you like this, make sure to read my other stories. Think of your votes and comments as your contribution to my stories! Thanks! * It had been a long week for me, and I had a feeling there was still a long w...

Happy Shavesgiving

by 9volt on Dec 24, 2019
Fetish

I woke up, to the most wonderful feeling in the world, as Brandi's lips were wrapped around my cock. She smiled and winked at me as I opened my eyes. She released my cock and caressed my balls with her talented tongue before returning to the head of my cock and slowly, teasingly, gently engulfing the head of my cock. I was close and she knew it. Suddenly s...

Night With Chantz Fortune Ch. 09

by lilguy on Sep 16, 2017
Celebrities & Fan Fiction

I sat there naked with my pig tails on. A chain was around my neck and I was on the bed. Chantz had put a cock ring on me and I could hear the sounds of Chantz having sex with 3 men upstairs. She had told me I wasn’t man enough for her and she needed a man. She was tired of my sissy body. She been up there for hours. “Fuck me…fuck me hard. Right in the ass....

Charlie and the Chocolate Factory

by AfroerotiK on Jul 27, 2020
BDSM

One of the real joys of the holiday season is how the kink community comes together to celebrate. It seems that everyone is allowed to let their hair down that much more, to party like pagans, and to lose him or herself to pure hedonistic pleasure. This holiday season, the Houston kink community was coming together not only to celebrate in grand style, to sa...

Seven Lessons Ch. 02

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

Previously... Bryan is an arrogant biggot. This Halloween season, someone has decided to teach him a series of 7 lessons. Yesterday the lesson was acceptance, but as he chose not to accept the lesson, he ended up with no body hair, wearing a bodystocking and being fitted with a chastity device. Will he learn his remaining lessons? That night he had many...

The Matriarch Ch. 01

by AMurphyWriting on Jan 8, 2019
BDSM

*This chapter deals with much of the administration that new pets at The Matriarch must undergo. As a result, it doesn't contain as much of the good stuff as the introduction did. Rather, it lays more solid groundwork for future chapters.* ***** *When last we left off, our young protagonist had just been hired on as a pet by the notorious Violet, owner of...

Sissy's Shopping Trip Pt. 02

by SissyFaye on Jul 6, 2020
Transgender & Crossdressers

Hearing my beautiful mistress say that she needs to cum before continuing gets me excited. I have an idea of what she has in mind, but I'm not sure because this trip is different than any before. Mistress walks to the back passenger door and opens it, "Get in here on your back with your head on the edge of the seat," commands Mistress. As I comply, I not...