Strapon Sissy Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

Chastised, Feminized, Sodomized

by Stefani on Sep 25, 2017
BDSM

My name is Kim Lee. I am half Korean and half Chinese. My first name got me teased quite a bit when I was in school. Nor did it help that I am a bit small and slender. Consequently I grew up rather shy and reserved. I never really had many girlfriends, as most women that I ever met seemed to prefer bigger, more macho guys. So I was not prepared at all when I...

The Ex's New Toy Pt. 02

by Urtoy2be on Sep 15, 2017
Fetish

Dearest Dana, I am writing to talk to you about things that I am unable to say to you face to face. I want to go back to when we were still married and come all the way up to current date. Maybe you will, hopefully, like what I have to say. Maybe we can come to an agreement/arrangement that could be mutually beneficial and satisfying to everyone involved....

Steph and Giulia Ch. 05: Short Shorts

by BigHand32 on Sep 16, 2017
Fetish

It was dark. Giulia looked at the clock. 7 AM. She had explicitly told Stephen to come to her room after he took a bath, and "Come fuck me like a man". This wasn't for her. In fact, the thought didn't really appeal to her that much... his tiny body and tiny cock working inside her until he had a pathetic orgasm. She just wondered if he would if he was not j...

Becoming the Sissy Slut

by HappyCouple74 on Oct 6, 2020
Transgender & Crossdressers

Story 5 "You are going to have to go, I don't see a choice here." My boss said to me. I didn't want to go on this trip. It was a routine check of one of our automated sites. That meant about 10 days of living in a hotel and checking in to the control room once a day just to see how the automated diagnostics were going. Normally, we send Gary, the junior st...

Busted Wearing Panties Ch. 04

by tonyl65 on Sep 18, 2017
Transsexuals & Crossdressers

I want to thank the readers for hanging in there with this story line. I also want to thank you for the wonderful comments. I appreciate you all for taking the time to send me an email or comment, I will respond to you all. Chris and Jessica had to leave for a dinner engagement which they could not get out of. Emily and I we wanted to be alone anyway so...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Neighbourhood Terror to Sissy Pt. 17

by Fibaro on Feb 3, 2020
Transgender & Crossdressers

Chapter 19 The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her...

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

How I went from Domme to Slut Ch. 09

by Ms_Allison on Sep 11, 2018
BDSM

First I would like to thank mantoy999 for editing and suggesting content for this story. Also, I'd like to thank the readers who have reached out through Email or comments letting me know their thoughts. I love hearing from you all. ~~~~~~~~~~~~~~~~~~~~ To say I was shocked when Ms. Deb stopped into my U-shaped cubicle would be an understatement. While she...

Dominant Black Tales and Submissive Ch. 01

by AfroerotiK on Sep 13, 2017
BDSM

Did she have a hidden agenda? Was her desire to dominate white men driven by some racial hatred or need to seek revenge for her enslaved ancestors? By all outward appearances, that would appear to be the case. Mistress Desire was far more complex than superficial appearances would allow. Black, strong, confident, and proud, there was no mistaking that the Do...