Sissy Plug Stories

24,564 results
Orientation
Length
Source
Infinite Scroll

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

How I went from Domme to Slut Ch. 03

by Ms_Allison on Mar 7, 2018
BDSM

Another night of not knowing and torment was coming, this time I would have company, amber would be with me. This would be new. Ms. Linda had contacted me during the day via text. Her instructions were quite simple, amber and I were to bring a selection of slutty lingerie for her to choose from, our highest heels, and not bring any attention to ourselves as...

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Chrissy's Night Out

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: A Snack Before Dinner Four days have passed since Chrissy's adventure at Futanari Palace. Since that glorious night he only goes by Chrissy, he no longer identifies with the name Chris. He has begun dressing only in women's clothes, with full makeup and a wig. His coworkers weren't all that surprised by his change in behavior, they have suspected hi...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

A Sissy's Uniform Pt. 01

by Deeznuts4pm on Sep 14, 2020
Transgender & Crossdressers

I suppose the best place to start here is what my life currently looks like. I'm a 25 year old chastity sissy maid that lives with my dom. I would tell you my name before I was a sissy, but there's little point, so the name we are going by here is Jessica. I've always had a skinny build, and this is well complemented by my dark brown hair, which after servin...

Discovering Amber Ch. 06

by Ms_Allison on Feb 12, 2019
Transgender & Crossdressers

Mistress notes: Once you understand them sissies are rather easy to manipulate and control. It's just a matter of finding which buttons are the ones that need to be pressed and when to press them. amber has a weakness for lingerie, heels, and humiliation. Additionally, she was very easily brought to her knees at the promise of an orgasm. Getting dressed up...

The Perfect Night

by transgendercharmander on Sep 16, 2017
Transsexuals & Crossdressers

It was finally happening! Mistress H arranged to meet up with me at a nice hotel to have some fun. She told me depending on my behavior; she may decide to move me in with her to be her full time slave. This was the opportunity I had been fantasizing over for months! I knew I would have to do my best to please her, so immediately upon hearing her orders to me...

Down The Path Ch. 03

by gbr2004 on Sep 14, 2017
Fetish

This story involves gay sex and forced fem, not your thing, move to another story. * I haven't been able to concentrate all day, didn't get anything done. All I can think about is having to go back to the bookstore tonight. I don't know if I can do it but if I don't I'm not sure what he might do. Maybe he just won't contact me anymore and I really don't w...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...