Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

Mistress de Sade's Sissy School

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

My whole body hurt, everything, both inside and out, the pain had brought me agonisingly awake. I could feel the bars of the cold cage I had been thrown into, it had been my home for several months but the beating was new. The other sissies had turned on me, they might be 'girly' but they were cruel, Mistress Kayne had warned me that to disobey one last ord...

Pretty in White Ch. 01

by wendy_james on Sep 16, 2017
Transsexuals & Crossdressers

Pretty in white... That's what my Mistress whispered in my ear after she finished dressing me in a white bra, a white knit camisole, a white linen blouse, white sheer pantyhose, and the palest-of-pink panties over them. She stood me in front of her full-length mirror in her dressing room, and she came up behind me. I was wearing white open toe sandals with...

How I Became Sissy Willow Ch. 04

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

It was now Saturday afternoon. Last night, after I'd returned home from work I had been dressed in women's clothes by my wife, Allie; introduced to her lover, Mike; been made love to by him myself; been subjected to physical and emotional torture by the two of them; and had it all captured on video. This morning I had had all my body hair removed and had pa...

Big Bobby and Sweet Sally Ch. 03

by DanteDidIt on Jan 31, 2018
Transsexuals & Crossdressers

We drove most of that first day we were together, through a state and a half at least. Big Bobby had miles upon miles to catch up on since we got a later than usual start that morning. I just sat in the passenger seat, taking in each sight and sound the road had to offer. My now smooth bare legs were propped up and perpetually warmed by the glimmering sunlig...

Covid 19 - Pete Turned into Charleigh Pt. 04

by His_fag_wife on Jul 27, 2020
Transgender & Crossdressers

Red unlocked the locks, unclasped the clasps on the box and then popped the lids back on the two bottles of poppers, but popped them in place for later. After this first session being so much of a hit, she thought Charleigh might be in the box for some time, every day for the coming weeks, if the lockdown remained in place for that long. At least then the du...

Handyman Pt. 04

by lovedart54321 on Sep 28, 2020
Transgender & Crossdressers

I started my new job and was forced to focus my attention on learning a new field, with a strong understanding of chemicals, working around food, thorough site inspections, paperwork, etc. As much as I wanted to focus on Tony, Gina, our home, and the new living arrangements, I also didn't want to mess this up. I knew Tony had put a good word in for me, and I...

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...

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Lingerie Does Make the Man

by lingerielover on Sep 12, 2017
Fetish

What do you think you are doing? She asked, and I knew I was caught and I was going to have to pay for my indiscretions. I didn't know what was going to happen, but I knew it wasn't going to be good. I guess I should start from the start of the day. I got up early like I always do and was just waiting for everyone to leave the house for the day. The kids wo...