Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

Caught Red Handed

by desireethtttv on Sep 15, 2017
Transsexuals & Crossdressers

With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse is completely opposite. Suzie is a Goodwill addict, with anything at a bargain giving her much pleasure. Me, I'd...

Virgin Ch. 03

by SissyKirsty on Sep 13, 2017
Transsexuals & Crossdressers

My last thoughts before I fell asleep were that I was now his, a thought that has washed away since and been replaced with shame as I wake with a pillow in my face. Shame, shame, and more shame. Why did I do what I did? What possessed me so? I kissed another man! I let him grind up against me and dry hump me. I even grinded back! I sucked his cock and came w...

On a Scale of 1 to 10

by His_fag_wife on Apr 17, 2019
Transgender & Crossdressers

He couldn't help himself, it was a new office environment for him and she truly was stunning. Even her little sister Claudia was delightful and sexy, but in a more understated way. The fact that she worked for Georgia her sister, set the hierarchy, but even more so, Georgia towered over her younger sister, and then there was Georgia's innate sense of style a...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

My Birthday

by hemlocks on Sep 14, 2017
BDSM

I knew David and Cindy would be home in half an hour. Cindy is my wife. David is her favorite lover. We live with him. Cindy and I have been married for 10 years. For the past 2 years, we have had a new arrangement. I began to have problems pleasing Cindy in bed, and it led to fights. We talked about it a lot, over several weeks. We talked about the source...

Celeste Pharma Ch. 02

by HorribleHenry on Oct 19, 2020
Transgender & Crossdressers

CELESTE PHARMA CHAPTER TWO I spent a very bad night ruing the day and the hour I had met up with Damian and had found my way to Celeste Pharma's Research Centre in the town of Crabtree. In just the first day of the course I had been virtually stripped of my masculinity with the aid of a black demoness called Monika. According to her I had been rendered pe...

Summer at Pond Cove Ch. 07

by The_Technician on Aug 14, 2018
BDSM

Walter and holly are taken to The After Hours Social Club where they participate in a couple of very interesting contests. This is a long story at over 9,000 words. The preparation in advance for the visit to the club involves some difficult, almost punishment, enemas, etc, but there is no scat play or anything like that. At the club walter is involved prim...

Following My Heart

by Alexdino on Oct 9, 2018
BDSM

House sitting for my fiancé was supposed to be a nice way to ingratiate myself with her and get back into her good graces. Nothing I could do seemed to make her happy, including the way I jumped to do her favors, took care of her dog, and was generally supportive. No matter my efforts she looked at me with suspicion and doubt. That's why I spent much of the...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...