Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

Slave Ch. 01

by slaveheathen on Sep 25, 2017
Fetish

My name is slave. Of course, that's not my real name, but for the story I plan to tell, it will do. For the record, I'm a bisexual submissive male. There are few who know this fact. Common enough story there, I suppose. Truth is, my family and friends could never accept my lifestyle, so that part of myself stays safely locked away. But behind closed doors....

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...

Black Cuckolding In Montreal

by Samuelx on Sep 11, 2017
Interracial Love

Never say never, I guess that's what the moral of the story is. When my husband Benjamin "Benny" LaCroix told me that he wanted me to cuckold him, I think my jaw hit the floor. Benny is six-foot-one, lean and muscular, with dark brown skin, curly Black hair and lime-green eyes. My darling husband is biracial, born in the City of Montreal to a French Canadian...

Relaxing

by Sissy_Desire on Jul 15, 2020
Toys & Masturbation

**This short story contains elements of solo sissy anal play and cum eating. If you are not comfortable with that, please check out another wonderful story from a different creator. If you choose to stay and read, thank you. You're my kind of kinky slut.** I always enjoy swinging by the local adult toy shop. I've been there a couple of times before, and the...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

Shelly and "Jenny's" Story Pt. 02

by akak28 on Sep 26, 2017
Transsexuals & Crossdressers

I saw my wife leaving out of the corner of my eye, and I knew it was time. I hadn't spent 15 years at this company to be fired for no fucking reason. I was a man, and I was going to take what I deserved. I had already decided I was going to talk to Marcus at this party, but when I looked around I couldn't find him. Instead, I found Chantlle, Marcus' wife by...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

I Become Wendy's "Wife"

by Quietoldie on Sep 16, 2017
Transsexuals & Crossdressers

After the amazing weekend I thought things would settle back down to our usual routine. She was out working all day so I had to wait until the next weekend to go shopping with Wendy for my new wardrobe. In the meantime she allowed me to wear any of her clothes that I liked but most were a bit too big for me and Wendy had only a few dresses and skirts to choo...

Mrs. Claus's Predicament

by tcs1963 on Jan 7, 2019
BDSM

Wrote this story right before Christmas, Edited and proofread by my friend, TakeMeDown... ***** It was Christmas time again, and everyone was very joyful at the North Pole. Toys were being made on every table, hot chocolate was brewing and smiles abound. It was a beautiful holiday scene, with the exception of Dear old St. Nick being mysteriously absent....

Loving Wife Ch. 03

by Agena on Sep 26, 2017
Transsexuals & Crossdressers

Disclaimer: This is a story of fantasy and fiction. It is not about any known situation or person. You should be 18 or older to read it. Acknowledgment: The author wishes to thank Beautiful Midnight for editing and providing support for this story. Introduction: Bob goes deeper into a loving relationship of submission and femininity as his wife gains more...