Sissy Pregnant Stories

39,436 results
Orientation
Length
Source
Infinite Scroll

A Slut. An Insatiable Slut.

by hunter_gatherer on Sep 12, 2017
Loving Wives

"Mr. Jenkins and Mrs. Jenkins, I have seen enough over these last few months and will recommend an amicable divorce. It's the best for both of you. You will have joint custody of your four year old daughter, on terms you both can work out on," said our counselor. I was heartbroken. I had tried to make everything work. I wanted to be together as a family. A...

Sissy Finds a Friend

by Quietoldie on Apr 10, 2019
Transgender & Crossdressers

Andrew likes to wear women's clothes in the privacy of his home. He finds he's more comfortable dressed as a woman, and wearing frilly clothes makes his cock stiffen up nicely. He's been married to Wendy for ten years now. She discovered his fetish by accident six months ago and has come to accept his need to cross dress. When she returned home early one da...

The Odd Couple

by ElderDirt on Oct 10, 2018
Romance

Author's Note: This story is based on the unlikely pairing of two friends of different sexual persuasions. The names of the characters have been changed to protect their identities, and a liberal dose of literary possibility has been applied to fill in the gaps as to how their romance grew and blossomed. Enjoy the telling. ~ ~ ~ ~ ~ "Hey, girlfriend! Why a...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

Joining the Ranks of Lady Bois

by eviltwin52 on Sep 14, 2020
Transgender & Crossdressers

This is a story about one man's transformation from loving husband to lady boi. His evolution began with a colleague leading him to an aggressive indoctrination. The journey takes him from the safe confines of a married Caucasian heterosexual male to celebrating his new life as Black cock loving lady boi. On a side note I have chosen to turn off the anonymo...

Isabella's Reversion Pt. 04

by silverbackteddy on Sep 11, 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...

The Cabin Ch. 07

by MaddieKim on Sep 14, 2017
BDSM

This is the final chapter of The Cabin. The story would not have been posted without Kirk2004's editing abilities. Once again, thank you, Kirk. ~*~*~ The Kitten is curious "Admit it, Kit. You're curious. You wonder what it would be like to be tied up and fucked." "I don't..." Kit's fingers went to the scar. Oh hell, Michael thought. She had been tied u...

Caitlin and Mistress Vicky

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang. *ring ring* Swallowing nervously,...

Mandy Sucks

by LilLindaMelons on Sep 16, 2017
Transsexuals & Crossdressers

I've written this fictional story in a POV style depending on what feedback I receive I may write more like it. I've been chatting to an older man for several ages and finally get up the courage to meet him. I dress up in one of my sexiest outfits and meet him at the appointed time and place. He drives me to a warehouse on an industrial estate before I kn...