Sissy Glory Hole Stories

127,566 results
Orientation
Length
Source
Infinite Scroll

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...

Property To Be Pimped

by desireethtttv on Sep 11, 2017
Transsexuals & Crossdressers

It had been weeks since I'd brought to light my idea of my wife, Suzie, strapping on a big dildo and taking me dressed as Desiree, the Hot to Trot Transvestite. While at first she teased me with possible participation, it never came to be, despite me bringing it up on several occasions. She really didn't care for me dressing up, jealous of my clothing expend...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Neighbourhood Terror to Sissy Pt. 25

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

Chapter 27 Marcy woke up with a loud groan as her alarm went off loudly and way too early. She really had to drag herself out of bed as she didn't look forward to her day ahead at all, but she couldn't afford to waste much time at all as she still had a busy morning ritual to take care of. It started off bad with the kiss to the dildo, although she had to a...

Jacki's Journey into Sissyhood

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

I thought to myself could I really go through with it this time? I had to at least try it, didn't I? I took another swig of wine and then brushed the blonde strands of hair out of my face again as and I read through the message one more time. "Jacki, Id love to get together and treat you like the beautiful gurl that you are. Look over my pics and if you like...

The Sissy in the Loft

by Sissy_Sammi_ on Dec 31, 2018
Transgender & Crossdressers

*All characters are 18+ *** James grit his teeth and walked through the door, a bell ringing as he entered the store. It was getting late and the sun was setting outside. He had been waiting in his car for nearly 20 minutes, waiting for people to leave the shop and no longer be near the store. The lady running the shop looks at him with a strange look fro...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

A Big Change Pt. 04

by OldHarry on Mar 12, 2019
Transgender & Crossdressers

Dante's was not what I expected, not really sure what I did expect, but this wasn't it, this place looked like a private doctor's surgery, A red door and a small brass plaque with Dante's engraved on it. We parked up and the four of us approached the door, it opened in to a nice red carpeted foyer, the women at reception bid us good evening and asked about...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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