Shemale Gloryhole Stories

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Visiting Another Gloryhole

by rand0m on May 14, 2019
Fetish

Since writing my last story about my first glory hole experience I've been getting quite a few messages from other users telling me about their experiences or some asking how they could go about finding one. Corresponding with them just made me realize how many similar guys there are out there like me. I still consider myself more "straight" on the sexuality...

Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

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'''CHAT'''

by Ssrd33 on May 10, 2019
Transsexual

Hi Jhon!, Hi Mike ... I answered lazily ... like all the days, my life had become very routine and repetitive, at home my wife does not serve me as a man or husband, I think I was dating I sneaked in with another man, but at this point in my life I did not care and the children made a mess everywhere. I wanted to escape this prison from which I felt trapped,...

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Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Sherry's Adventures as a Slut Ch. 03

by BadBuzzard on Sep 13, 2017
Loving Wives

As soon as Sherry walked in her door after her incredible pussy-eating session with her friend Julie, she ran to the computer and logged on. She went straight to the Yahoo group that Julie had showed her and began to explore. The group's web site had a link to another site that listed adult theaters and gloryholes in cities all over the country. She nervousl...

Lissy the Gloryhole Stripper

by rick_oh on Sep 16, 2017
Fetish

Lissy showed up on time for her interview. She is a slender blonde female, about 23, with an engaging, sweet smile. Her yellow hair nicely framed her young-college-girl face. She wore a white blouse, jeans, and sandals. her attractive feet showed off her red-polished toenails. She told me that her name is Melissa, and she prefers that to her stage name of L...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

The Shemale Apocalypse Ch. 01

by cocklover1000 on Sep 15, 2017
Sci-Fi & Fantasy

The first place anyone really heard of it was large outbreaks in Thailand. No one knew what it was but the government played it off as a life choice via simple operation. But it was more then that. Minor cases were reported all over the world until 2011 the government in an effort to quell what they called an infection told the earth the truth about the wond...

I Dare You Ch. 3

by Digger66 on Sep 12, 2017
Exhibitionist & Voyeur

The following is intended for ADULTS ONLY. If you are under 18 or are offended by stories of a sexual nature, STOP NOW. This story takes place in a FANTASY world with no AIDS or STDs. In the REAL world AIDS and STDs can kill you. Protect yourself!!!! ***************************************** Several months had past. Work started picking up for Kay and me....

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...