Shemale Gloryhole Stories

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Infinite Scroll

The Rose Diaries Ch. 13

by RoseB on Dec 31, 2018
Transgender & Crossdressers

Disclaimer and Notes: The Rose Diaries is an incredibly dark story focusing on forced (heavy emphasis on "forced") feminization of a completely non-compliant individual. There are elements of non-consent, violence, and dark subject matters. In addition, this story depicts dysphoria, dissociation, and general depression. I hope you do enjoy this chapter if...

Attorney Client Privilege Bk. 07

by Bazzz on Sep 14, 2017
Interracial Love

37 Lis was slipping on her navy blue Jimmy Choo pumps when she first heard the noise outside her front door. She figured that one of her neighbors must have been moving something big into their residence as she checked herself out in the full length mirror. She was wearing a navy blue business suit and she knew she looked good in it. The skirt was a bit lon...

The Lost Boy Ch. 11

by DamienDeath20 on Apr 23, 2018
Transsexuals & Crossdressers

A.N. Helloooooooo. Okay so after a million and one inconveniences, a bombardment of snowstorms and power outages. I'm finally here again! This chapter has been done for a while but I've been working on other works preventing me from posting it. But those will be coming out soon as well! The Following Contains: Dick girls fuckin bois. Git gud. (Also som...

Jasmine Fantasies: Nylon Seduction

by silkstockingslover on Mar 31, 2020
Illustrated

All characters are 18 years of age or older. Summary: Jasmine is seduced by secret admirer in nylons. Note 1: This is an April Fools 2020 Contest Story due to not one, but two plot twists. Note 2: Thanks to NYLONSKITTY/NYLONSKITTEN for permission to use her photos. She really is a gorgeous woman and worth checking out. Plus, one old pic of me (I mean real...

Babysitter Cupcake: MILF Cuckqueaned

by silkstockingslover on Feb 26, 2019
Fetish

Summary: College girl seduces wife and then fucks husband. Note 1: I have been asked by a number of people for a couple of years to write a cuckquean story (which made me look up what cuckquean means). I had begun attempts on one a couple of times over the past couple of years, but I set them aside when the plots didn't work. Then after a few more requests...

SpellsRUs: Urge for Self Loving

by Aphotic on Sep 12, 2017
Sci-Fi & Fantasy

My thanks to: J R Parz, the inventor of the Master PC universe, one of the better class of MC stories. My heartfelt appreciation to J R D author of the magnetically compelling Witch Chronicles series. Xanthos Pendragon , his Master PC Eclectic's Edition reminded me of the consequences of messing about with others' actions and how it troubles the conscien...

The Screamer Ch. 07

by Liquor69 on Sep 14, 2017
Group Sex

[Author's note: From this point in the story, the characters will begin to interact with characters from the series; "Cherry Takes on the NFL" To avoid any confusion on my reader's part, a familiarity with both series would be helpful. Thank you for taking the time to read and for all your wonderful encouragement.] The party wound down and Jim stayed behin...

HypnoSissy: Becoming a Cocksucker

by silkstockingslover on Sep 18, 2017
Fetish

Summary: Straight guy watches porn tapes that are not what they seem. Note 1: Thanks to hfernandez1983 for the story idea and the intriguing revelation that hypno sissy videos exist in the first place. Note 2: Of course, all participants are at least 18-years-old. Note 3: Thanks to goamz86, Robert, DomMasterJim and Wayne for editing. Category: This...

Blackmailed to be Me

by sissyneko on Feb 3, 2020
Transgender & Crossdressers

The bottle was three inches tall with a one-inch diameter, it was orange with a white childproof cap. It was sitting in the middle of the small round table that took up almost a quarter of my studio apartment. I was staring at it. I hadn't changed out of my boy costume yet. It was Monday night and Mondays are always bad, but this one had been worse than most...

Lucky Man Ch. 22

by Mentalcase on Aug 24, 2020
Group Sex

Chapter 22 Kelly Her head was leaning against the wall as her shoulders bobbed up and down as she wept. The gorgeous young blonde was obviously upset. Kelly went over to Duncan and looked at him quizzically. He flashed a look of, "I don't fucking know," at her and immediately backed up. "I'm going to get you a bottle of water and a towel," he said, lookin...