Sissy Glory Hole Stories

127,566 results
Orientation
Length
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Infinite Scroll

Sammi Goes to College

by Sissy_Sammi_ on Dec 10, 2017
Transsexuals & Crossdressers

4th part to Sammi's story. After Sam graduated from high school, and knowing he'd be moving to college by the end of the summer meant he was just killing time until then. He worked for most of the summer at a restaurant as a server, and at night Sammi worked as a cam whore. He made some extremely good money by the end of the summer, and he was extremely pro...

How I Became Sissy Willow Ch. 03

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

I slept on the floor next to the bed that night, still in the lingerie and sundress I'd worn the day before. Fern and Jason, of course, slept together in the bed. As I drifted off to sleep I kept thinking about the events of the evening. I had been put in women's clothes by my wife, Fern after she found a magazine I forgot to hide. The magazine showed a tra...

Covid 19 - Pete Turned into Charleigh Pt. 03

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

"OK off with the wig now and we'll get rid of body hair first and then we can document the necessary changes." Mistress Red pulled off Charleigh's wig, one of the last vestiges of Charleigh's feminine sissy armor and as Pete looked in the mirror, he wondered if he was doing the right thing. With his bald head, flabby pecs and miniscule caged cock, he certa...

Sister, Meet My Sissy

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

George was mincing around the bedroom on his new high heels, almost moaning in joy as his big cock slid around in the inside of his panties. I could see the thick buttplug in his ass through the thin panty material and I smiled. George was a lovely sissy with almost feminine body type and features but with that delicious big cock. He'd taught me as much abou...

A Glory Hole for Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each days, growing into text messages each day, and more. No idea...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Sissy Chantel, New Reality Ch. 04

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life. 8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...

The Computerized Bed

by submissive~pet~ on Sep 14, 2017
Fetish

The year is 2020 all sorts of new inventions have been created. The time machine in which John Paul traveled was from the year 2002. He had no idea what was in store upon his arrival to the future. His machine carried him into a large bedroom. It was a very lovely room done in pinks and light blues. The bed was enormous in size, 4 times the size of any he...

Sarah had Sex in an ABS

by SarahCD on Feb 12, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Adult Bookstore Whoring

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Crossdressing sissy Terilyn Bardot arrived at the adult arcade around 6:10 p.m. The city was having some kind of carnival on the waterfront, and so most of the parking spaces were gone. Teri went in and stripped to just a 2 piece bikini and her high heels. She freshened up her hot red Revlon lipstick and greased up her anus with Vaseline. Then she waited. An...