Sissy Enema Stories

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Orientation
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Infinite Scroll

A Weekend Away Ch. 02

by SluttyChrissy on Sep 14, 2020
Transgender & Crossdressers

Author's Note: Thanks for all the kind feedback & comments on chapter 01. This chapter does a lot to set up the rest of the story, so there isn't a ton of sex. Please hang in there with me and there will be much more sex in the chapters 3-?? I hope this one is sexy enough to keep you interested! ---------------------------------------- I'm not sure how lon...

Sheila and Penny

by Sheila_TSSub on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 I had been upstairs that morning doing my chores. I was dressed in a cute little yellow summer dress and leather heels with 4" wedge heels. When I came downstairs I found Mistress Tina (my wife) and Princess Gina (our daughter) in the den. There was a man there that was unknown to me. "Come here." Tina commanded. I went in and knelt beside her cha...

Becoming CD Mistress Raven's Slut Ch. 02

by Vodka_Jim on Dec 10, 2018
Transgender & Crossdressers

Author's Note: I took some inspiration for this next chapter from some of the comments, both public and private, that I had to the first chapter. In doing so, I've written about things (e.g. forced cross-dressing) that I've never personally experienced. Most of my writing is based on things that I've experienced and that I think I can relate. So, if I've mis...

Casey's Submissive Journey Pt. 02

by corduroysissy on Dec 14, 2017
BDSM

Debbie's eyes bulged when he looked up at Angelina, and his best friend smiled back at him. "This is my Angie, Debbie, he wanted to watch you cream his jeans." Looking through the make-up and wig he could barely make out the face of his young buddy. Casey was blown away by how good Jamie looked as a girl, he was pretty as all hell. The make-up looked perf...

Letter from Tanglewood Springs

by justincbenedict on Jan 1, 2019
BDSM

Dear Shoeblossom, How can I start this? I was raised to be a spoiled brat, and I always seemed to get what I wanted when I had tantrums, even into adulthood. My parents always let me win when we played games, and I learned how to cheat in school and subtly sabotage other players in athletics, such as kneeing in basketball, to make me a star academically a...

The Wedding Ch. 07

by betamale08 on Mar 31, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 7 -- Wardrobes, Witnesses and Weddings... "Good morning sleepy head! It's just after 6a.m -- time to get up, we have a lot to do, come on now, it's you big day so up you get Gabby..." Sitting up in Carol and Darren's big very comfortable and still not really with it or awake, I didn't even realize that it wasn't Ca...

Pay for Pleasure - Prequel

by Pleasure_the_slut on Sep 16, 2017
Transsexuals & Crossdressers

I had written about how Sandy turned me into a $50 whore before writing about how I got to that point with her. I was cruising an online posting for sex one Thursday evening and I came across a posting for TV looking for big cock. Well that got my attention, I'm 8" and very thick. So, I shot a reply right away. Not a minute later Sandy and I started chatti...

Found - Again

by BufordTJusticeTX on Sep 16, 2017
Transsexuals & Crossdressers

This story is a work of fiction, if it has any similarities it's all in your head. It does have graphic descriptions of sex; all participants are above legal age. This is the second story in the set, I encourage you to read part one, Found. I appreciate all feedback. ***** FOUND, AGAIN. Sally finished the evening by telling me to go home and get some res...

Casey's Submissive Journey Pt. 07

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Note: This part of the story, and those to follow, occur after Karen had been accepted into the Lady's Club. ***** Karen spotted Betty Jean from across the room and she looked interesting. The ladies were all watching their husbands sucking and fucking each other in full drag, it was Fag Night at the Lady's Club and the sissies were giving them a really go...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...