Toilet Sissy Stories

36,221 results
Orientation
Length
Source
Infinite Scroll

Don't Avoid Daddy

by handjessicacd on Sep 19, 2017
Transsexuals & Crossdressers

This is my first story. I've never written about any of my encounters before, until recently when I've been wanting to re-live them in my head. I thought it would be an interesting story. Any feedback would be appreciated. Enjoy :] --------------------------------------------- It feels like I haven't been used in ages. I'm too much of a scared sissy. I fi...

Seductress & Daemon: Sissy Pt. 02

by SeducedKnight on Sep 15, 2017
BDSM

********** A continuation of my initial story, the next morning... ~~~~~~~~~~ Zombe: a black rubber o-ring type bracelet worn locally, either on wrists or ankles (or both in my case, I have an oversized one that I wear as a necklace too). ********** I wake early the next morning, Seductress and the sissy are still asleep, the sissy and I are snuggled in...

Wife in Control Ch. 04

by wifetoy on Sep 25, 2017
Fetish

This is the fourth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please review the earlier chapters for the full poem and the humiliations I have been forced to endure because of my failure. I did not think she would actually perform all of these cruel punishments on m...

Claire's New Start

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

There's the thick taste of cum in my mouth and my bum has that feeling of being fucked...filled...made love to and last night replays in my sleep along with everything that has found a home in my head. ...Stop lying, start loving that cock inside you. ...You've never been man enough but you can be sissy enough. ...Worship cock like a good sissy girl. ......

Retired to a Whole New Life Ch. 02

by sissymissyct on Feb 11, 2019
BDSM

As my fate was now sealed by the lock, Mistress Michelle handed me the key and instructed me to put it on Cara's ankle bracelet. I gently undid the clasp and attached the key as instructed. I re-fit the bracelet and lovingly kissed her foot, and then Mistress Michelle's. They helped me too my feet and we went back out to the living room, Michelle locking th...

Sissy Girl Forever Pt. 02

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies p...

My Little Slut Ch. 02

by Sweetblood03 on Sep 12, 2017
Fetish

"My apologies, Mistress." He pulls up the flimsy black knickers over his softened cock, bends his head and begins to lick the pooled cum off my sleek black boots. "You realize that this means a day with the cage on for your forgetfulness, don't you, pet?" I reach down to stroke his cheek while his tongue works over the leather catching every last drop of c...

Lauri's First Adventure Pt. 02

by stockingsofsilk4me on Feb 25, 2019
Transgender & Crossdressers

Part II (thank you for the positive feedback on my first story ever!) ------------- From our many chats on Yahoo, Micha and I knew each other quite well, even though this was our first time meeting. I knew she was definitely the more dominant (and experienced) of our pairing and I knew there were certain things she wanted to experience with me. Being the m...

My New Digs Ch. 02

by cuckytoher on Aug 21, 2018
Fetish

The ice cold water hit my tired body like a thousand stinging needles as the lights went on at 6 a.m. I jumped up from the floor to finish my shower in the two minutes allotted to me by Andrea and Marko. I quickly soaped myself up and rinsed myself down knowing the clock was ticking. If I lingered more than two minutes, the door would automatically lock and...

Sissy Training Week 01: Induction

by Peggylea on Mar 17, 2020
First Time

Some years ago I was under the supervision of a Domme Mistress called Neve who organised for me to undertake a course in sissy training so I fully understood my role as a smalldick submissive. She found me a place on a 6 week sissy training course with a teacher called Mr Deal who was very experienced and had devised such a program. I was to meet Mr Deal a...