Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Brittany's Strapon Hell Week 04

by humbleslave on Sep 14, 2017
Celebrities & Fan Fiction

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! After the week I'd had so far, including my most recent ordeal at the softball fields, I didn't figure it could get much worse. Today I had be...

Isabella's Reversion Pt. 06

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

Caught and Used

by rayd9 on Sep 18, 2017
Transsexuals & Crossdressers

I am a secret, heterosexual panty boy, that loves to dress up in my wife's lingerie when she is not around. My wife and I have two mutual friends named Mike and Mandy. Mike and Mandy had things stored in our garage while they moved. Well my wife had to go away for a day seminar for her company, and I had the day off. I have been looking forward to this day f...

Kinky Neighbors

by fun4all6969 on Sep 11, 2017
Loving Wives

I have lived next door to Nick and Sheri for several years now. I have secretly lusted over Sheri since the day we met. Every time we talk and chat, we flirt endlessly back and forth and I use any excuse to touch her. I decided to invite them over for a friendly barbecue and swimming in my pool. There were 7 other people there besides us and Sheri showed u...

Nailed In My Office

by humbleslave on Sep 17, 2017
Celebrities & Fan Fiction

This is a continuation of "Being Brittany's Bitch" and "Chantz and Brittany's Toy" Brittany had just gotten done fucking my ass in front of all of my coworkers, and was leading me to my office by the leash to which I had grown so accustomed. "You thought we were rough on you, you better brace yourself bitch boy, because you're about to be gang-banged," she...

The School Slut Ch. 03

by cherrybubblebutt on Sep 12, 2017
Transsexuals & Crossdressers

Over the next few weeks I was working for George he would continue to give me my 'jabs' and we would pretend that I was an honest maid, well in front of his wife anyway, when we were alone (which was most days) I would insert a butt plug and go around doing my chores until waiting in one of the many rooms George would be waiting naked, maybe with a whip or c...

Cross-Dresser Fucked by Hot Sissy

by kinkibiboi on Sep 16, 2017
Transsexuals & Crossdressers

Today I was feeling particularly horny and decided it was time to get some action again...! I jumped online and setup an online account with adult friend finder! With my online account setup under my assumed identity I tentatively chose some revealing photos to upload... It didn't take more than a couple of hours before my pictures were up for all to see a...

My New Neighbours Ch. 03

by csm1967 on Feb 25, 2019
Transgender & Crossdressers

I closed the bathroom door and looked at Katie. 'So, how was it?' I asked. She looked at me and smiled. 'It was great my love. I am a bit sore to be honest, but I can understand why you are so captivated by Angie and Tilly - they are amazing girls.' I nodded. 'They certainly are. I hope you weren't shocked by some of the things they said. Or I said for th...

Discovering Amber Ch. 03

by Ms_Allison on Sep 25, 2017
Transsexuals & Crossdressers

Ms. Allison's note: Again thank you to all those who have had such wonderful things to say about amber's story. Yes, these are true and yes amber is a very lucky girl. Those of you following these stories will notice that amber refers to her body parts in female terms, her penis is now called a clitty, her testicles are tessies and her ass is now her pussy....