Shemale Gloryhole Stories

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Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

How Dicks ended up in My Mouth Ch. 01

by ret123 on Sep 19, 2017
Transsexuals & Crossdressers

My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets. The story begins when m...

Adventurous Outing

by Broadvue on Sep 26, 2017
Group Sex

Kimmy and I have been together for a few years now. When we met she was sexually inexperienced, having not been any men before me. But after a couple years of having a steady boyfriend, she was finding her adventurous side. It started out just trying different positions in the bedroom, but then it extended to discrete touching in movie theaters and restauran...

Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

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Brazilian Shemale

by Thorsten007 on Dec 30, 2017
Transsexual

Rules: Needs to be a brazilian shemale with big tits, a fat cock and a nice round bubble butt! Feel free to continue and create new storylines.What's next? James Kingston Pablo What's next? James Kingston Pablo...

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Gloryhole

by russello on Sep 13, 2017
Group Sex

Annette sat alone at one end of the wobbly barroom table, wondering how she had let herself get talked into coming here. She didn't like noisy drunks, and she didn't like loud music. She didn't like alcohol, and she didn't like being flirted with by drooling morons. She didn't like her sister's friends, and, though she tried not to admit it, she didn't like...

Victoria Justice: Dirty Girl

by MrMaxLord on Dec 17, 2017
Celebrities & Fan Fiction

All of the following is complete and total fiction. Not a single word of it ever occurred. Victoria Justice: Dirty Girl by MrMaxLord (MF, MFM, oral, anal, DP, DVP, gloryhole, cons) ***** The night was dark. The only illumination of this long stretch of desert highway being the occasional gas station or roadside diner. And to Victoria Justice, that was j...

Becoming Marie Ch. 01

by mariethetv on Sep 16, 2017
Transsexuals & Crossdressers

I'd had always liked dressing in women's undies from an early age. It was usually my older sister's panties and skirts whenever possible. When I finally left home at eighteen and moved into an apartment in the town center, it really took off. I had had a few encounters with a few guys, mainly glory hole fun in the local cottages. On a few occasions I found t...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Shemale Shopping Spree

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye a...