Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Morning Glory

by dreadknots on Apr 25, 2018
Transsexuals & Crossdressers

Reviews for my last crossdress-y story were pretty good! Hurray! This one is a little more teasing in nature, but is ultimately pretty fuzzy. I am a sap. *** Hardcore Fitness was the classiest gloryhole in town. All the right people knew what went on behind the illusory front of a 24/7 gym, and the syndicate behind its operation paid off the right guys in...

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...

Abducted and Turned Out Ch. 05

by dawnib66 on Sep 19, 2017
Transsexuals & Crossdressers

.... I lapped at her pussy as she intermittently moaned and derided me. "Eat that cunt, you sissy whore. I know you prefer cock, don't you? Answer me slut!" she said as she forced my face deeper into her pussy. "Yes, mistress," I said into her cunt. As I did, she moaned loudly and her pussy spasmed as she gushed into my face. "You are a good little bitch,...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...

Dual Use Building Retail Strip

by Alluring_Crimson_Shifter on Dec 24, 2019
Anal

Nancy was recently separated. She had to start a new life and was busy getting an affordable place to stay, and a new job. She stood in front of the mirror getting ready for work. She was a hair stylist, and she loved her silky brunette hair. She looked at the frontal view of her panties and loved how good her pussy looked. "Hello good looking," she said to...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Sissy Comes Clean

by Cuckyboy3 on Oct 6, 2020
Fetish

Reflections after Mystic: On the scenic drive back home from a fall getaway vacation with my lovely wife, I pondered quietly how the excursion would be remembered as a first of a kind. I had begun the trip with the expectation of a quick and routine spanking followed the next day by an epic sex experience. Three days later, however, I emerged having not onl...

Becoming a Sissy Maid & Slut Vol. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eighteen: Some New Friends for Chantel. A blissful night's sleep has led me to a wonderful Sunday day off. Master has told me I must accept that special Sunday plans are on the go after 3:00pm but today, this morning awaking at 9:00am I run my routine, enema, shower, put on fragrant body lotion. I then begin a day of dressing just for myself, but al...

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...

Desiree and Big John

by desireethtttv on Sep 12, 2017
Transsexuals & Crossdressers

It had been only a week since I'd introduced "Desiree, the Hot to Trot Transvestite" to my girlfriend Suzie, leaving me not a bit surprised that she chose not to spend the very next weekend at my place. While she hadn't freaked out, she was concerned I was gay since I was so convincing but I assured her I was not. I planned on revealing the truth I'd been wi...