Sissy Pregnant Stories

39,436 results
Orientation
Length
Source
Infinite Scroll

Cuckold Story

by Grey Eagle 286 on Sep 19, 2017
Loving Wives

I watched my wife of ten years as she entered the den where I was working on a report for work. She was looking very good. Grace wore a light brown leather skirt with a pale yellow shell and Cardigan sweater set over brown boots with high stiletto heels. Her body is amazing, and is centerfold quality for playboy. I am very proud of her. I smiled at her, "Yo...

AliExpress and Sissy Downfall Pt. 10

by His_fag_wife on Jan 23, 2019
Transgender & Crossdressers

As Charlie with her head raised off the cushion admired her new sissy pussy, she felt a complete head rush. As she and Tim had discussed just one guiche piercing at such length, over and over, texts flying back and forth on the crest of a wave of horniness and a submissives deep desire to please, she had fixated on the idea of being pierced without her wife...

Wife Turns Slut For Husband Ch. 02

by Dirty Slut on Sep 26, 2017
Group Sex

The Worm Turns Intro: As you remember in the last saga my husband had begged me to turn him into a cuckold. As things turned out I found out that he wanted to see me fucking other men, and not just any men, but black men with big black cocks. It was a torturous decision for me, but as I loved Billy so much I finally made contact with a black man on Billy’s...

Sissy: That Time of Year Again

by caprine on Sep 14, 2017
Erotic Couplings

[This is a work of fiction. The story is an unadulterated and unabashed attempt to tickle male fantasies and perhaps some female fantasies as well. As such, the story may or may not totally conform to reality. All locations, events, and characters are entirely fictitious and any resemblance to actual persons, living or dead, is purely coincidental.] *****...

Wife Humiliates, Hubby's Turned On Ch. 02

by Quietoldie on Mar 17, 2020
Transgender & Crossdressers

Bernie (formerly Bernard) That night after Carol had told me she was going to look for another man to inseminate her Carol took me by the hand to our bedroom and dressed me in the loose bra and panties along with the nightie she normally wears to sleep in. "You can wear them from now on sweetie, I've decided to sleep naked in future. You don't mind, do you...

I Love Men to wear my Satin Panties Pt. 01

by Manndee on Apr 25, 2018
Transsexuals & Crossdressers

I was a quiet unassuming lad from the East end of London; I was 22 years old when I left home, it followed a number of pure flukes that all happened back to back, because of this I had had an amazing start to my life in my first job as a City trader. Unfortunately, things at home with my girlfriend were getting difficult after me losing my job. It was now 4...

The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

Jesse's Journey Down a Rabbit Hole Ch. 14

by sadkins116 on Sep 14, 2017
Illustrated

I want to thank everyone for reading, voting and commenting on our story. I submitted the first six chapters, and Rebeccasm submitted chapter 6 through 12. I will be submitting chapters 12 through 18. We have both worked hard on this series and as such both deserve to share the postings. Hopefully you will visit both of us and enjoy the series. As I mention...

Breeding Natalia

by sweetsatine on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Nathaniel Geller had been a young, up-and-coming salesman at MedZ who'd shown great potential. In just a few years, he made his way from ambitious college graduate to savvy junior manager. Risky ventures that others were skeptical of luckily always seemed to turn out succes...

The Making of Davina Ch. 02

by Timewarp10 on Nov 20, 2018
Transgender & Crossdressers

David put make up on, and looking in the mirror he liked what he saw. It was as if he saw himself for the first time; a person within being born. Davina came to life. "Oh God! It feels so right!" David remarked, seeing Davina smiling back with Davina's eyes, and not David's. He was looking through a portal into his own true soul, and he wanted to step into...