Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

First Time Bi

by First_time_bi on Sep 16, 2017
Transsexuals & Crossdressers

I never thought that I'd be in this position. I am a 40 year old married man, 5'9" 185 lbs and try to work out regularly to keep in shape. The problem is that I travel constantly for work. It takes a tremendous amount of willpower to avoid the junk food and commit to a workout schedule when I am on the road. For the past 3 years, I have been the leading sale...

More Than I Wanted Ch. 03

by gbr2004 on Sep 16, 2017
Fetish

This story continues the saga of Steve and how his life is changed from one meeting with Mike, the man who is now in control of Steve's life. Mike has pictures that will he is threatening to send to his employer if Steve doesn't do as told. Worse yet, he threatens to send the pictures to his parents and brothers and this is not an acceptable option for Steve...

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...

A Night of Makeup, Cock and Cum

by mikhaylacumme on Sep 13, 2017
Transsexuals & Crossdressers

It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I had always wondered what it would be like to be with one a...

A New Adventure... Ch. 04

by johnjinglez1 on Nov 19, 2018
Transgender & Crossdressers

This is the fourth installment of my "Sex Diary." For the better part of a year and a half I decided to try some new things in the world of CD / TS / Sissy boys. All stories are 100% real. After my last encounter with Mia things really started to cool down on the TS/CD front for me; I'd met a couple of girls who really interested me and were satisfying my s...

Sammi's Place in College

by Sissy_Sammi_ on Dec 17, 2017
Transsexuals & Crossdressers

Sammi was up at seven AM, as usual, fully dressed and dolled up and tidying up the suite. Something had broken in her brain at this point, she had been re-wired. Her life had taken some drastic turns, and who she was and what drove her had been completely replaced by something new. Sam, in the past, had been at the helm and would occasionally allow Sammi he...

From Her Ex-Boss to her Bitch Pt. 06

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. ***** It had...

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...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Chatroom Trick Ch. 03

by ukmaleslave on Sep 15, 2017
Transsexuals & Crossdressers

For those of you first reading this let me fill you in on a Friday that that opened my eyes. I am a 26-year-old normal guy who had for sometime been flirting and playing with an older woman named Mary via an Internet chat room. She was about 41 a firm fit body and gorgeous red hair, perfect, better than that she didn’t live too far away. Our chats didn’t rea...