Sissy Wedding Stories

39,844 results
Orientation
Length
Source
Infinite Scroll

Brianna Gets Caught

by Sissy_Sammi_ on Feb 7, 2018
Transsexuals & Crossdressers

All characters are 18+ years of age. *Also, this is the 6th installment in Brianna's story. It makes more sense if the others have been read. Also thanks for the support. ************************* Brianna was in her room at Diane and Rick's after school getting ready. She was given a short mid-thigh blue skirt, a white T-shirt, and her classic pink conve...

Candi's Conversion Ch. 01

by CandiCumminz on Sep 10, 2018
Transsexuals & Crossdressers

I'd been having a great time since I lost my job. My wife was convinced I'd be devastated, so initially she indulged my days of computer games and jerking off with rapidly fraying sympathy. I failed to see the anger and resentment as she asked my to move my feet so she could hoover under them for the 100th time. It went on like this for a couple of months,...

Panty Boy Diaries: Entry 03

by _pdy_ on Apr 3, 2019
Transgender & Crossdressers

Does she know? Can she tell that I just got fucked? She must be able to smell the sex on me, right? My mind is racing as I sit here in this Uber on my way back home so that I can make it to my dinner with friends on time. The driver is a nice, middle-aged woman who's doing her best to be nice and polite. She asked me to sit in the front seat as she feels mor...

Brown Sugar Ravaging Ch. 03

by ILuvItBlack on Dec 25, 2018
Interracial Love

In Chapters 1 and 2, Eddie met Ty, right after Sherri had met Marcus. Both were being shown things they hadn't experienced before. Finding that he was able to take Ty's cock that had a large distortion because of a child hood accident, had Eddie giving it all up to him, and as he fucked him, Ty claimed Eddie as his for while he is visiting his Mandingo frien...

Blaze, Kami, Lyle and Poor Reggie!

by justincbenedict on Nov 20, 2018
BDSM

"All right, Lyle, when I whistle in F sharp, Reginald's thingie is supposed to wilt. If it doesn't, you strike it with the thorny rose branch." "P-please, darling Blaze-" "Shut up, Reg. We've been working on this all week. I need you to be ready at the play party, or Mistress Salem will be laughing at me, the bitch." "Yes ma'am." Lyle shook his head as h...

A Shemale Vacation Ch. 01

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was s...

My Second Piece of Ass Ch. 27

by Fable on Sep 13, 2017
Erotic Couplings

On Monday morning I overslept. Having had my bedtime delayed by Petri’s telephone call and having it interrupted by Ollie’s telephone call and being awakened again by Laura’s hand around my cock in the early morning gave me three good reasons to turn off the alarm and go back to sleep. Petri’s call came early and was welcome. She was alone and wanted someon...

It Finally Happened!

by d_p_sweetie on Sep 17, 2017
Loving Wives

The car came around at about 9 o'clock for her. My stomach was a bundle of nerves waiting up for this, but no matter how many angles we discussed, this was possibly the best option we had to save our marriage. I looked over at Lauren and smiled at her fresh, present, and sexy as the day I met her —sexier, even, if it was possible. She blushed a little, look...

Kasey's Confession Ch. 21

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Neil and Ted collected themselves, and before I could position myself on my knees in front of Tony, they made it clear they were leaving. I got up from the floor, steadied myself in my heels, and walked with them to the door. "Catch you later," they intoned to me before turning to Tony and saying, "We'll be down at McMurphy's later if you want to meet up."...

Kasey's Confession Ch. 07

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Whatever Derek had given me, it lowered my inhibitions and made me very eager to give into my fantasies. The voice inside that told me to run from the situation was getting fainter and while I was somewhat panicked by Mr. Smith's stated intention to "break" me, a larger part of me was intrigued. It wasn't like I hadn't been with men before and it wasn't like...