Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

Slave Ch. 04

by slaveheathen on Sep 25, 2017
Fetish

Note: Yup. Fetish story. Don't like it, don't read it. Comments and constructive criticism are welcome. On with the depravity... I slept late the next day, oddly enough. Couldn't have had anything to do with being utterly exhausted. Oh, wait. Yeah, it did. I was ready to crash after the shower, but Mistress Kay made me eat her pussy for an hour before sh...

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

A Big Change Pt. 02

by OldHarry on Feb 25, 2019
Transgender & Crossdressers

The morning after my "Fitting" found me back in work and my focus was on the tasks of the day, yet in the back of my mind I kept on hearing Mary, "If you can suck cock as well as you lick pussy, you'll be very popular." It was those words, "Suck cock," I have never sucked, or wanted to suck a cock, if she thinks that, then is very much mistaken. I had to re...

Sissy Dust Pt. 01

by Sissyhalo on May 29, 2018
Transsexuals & Crossdressers

All characters are over 18 years of age. ***** I'm not a genius or anything but I did get a decent job out of university with my bachelors of chem and started working in a cosmetics company. No not the testing division but in formulations. And it's a boring job really past the actual chem coolness of seeing reactions happen in new things and the way thin...

Getting Married

by hotdaddy9 on Mar 17, 2020
Transgender & Crossdressers

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home...

I Get Married

by hotdaddy9 on Mar 7, 2020
Transsexual

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home and...

Open in Reader

Neighbourhood Terror to Sissy Pt. 16

by Fibaro on Jan 6, 2020
Transgender & Crossdressers

Chapter 18 Marcy had hoped the stop at CC's would have been the last one. She had suffered enough embarrassment for a day. Lisa's claim that they still had a few errands to run made her worry that it wasn't all over after all. Her worries were soon confirmed when they stopped in a rather seedy looking neighbourhood. Getting out of the car Marcy knew better...

Becoming a Sissy Maid & Slut Vol. 09

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Prefix: I will be fast forwarding a few days in my sissy maid, sissy slut lifestyle story here. From the last chapter ending on a Tuesday night going into my second week as Master George's full time sissy maid and slut to that of me getting ready for the following Saturday night of slut service. I feel the story's journey no longer has to follow a linear da...

The Prize Ch. 01

by Holly2 on Sep 17, 2017
BDSM

After Jeff served them all tea and cookies in the nude, the women voted on who had succeeded in humiliating him the most during the course of the afternoon. The Twins who had invited their friend Mike over to help in his degradation were the unanimous winners. His ass was still sore from its first fucking, and the shame of then having to suck off that same c...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...