Dirty Crossdresser Gloryhole Stories Stories

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Crossdresser's Private Gloryhole

by kccrossdresserleslie on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story, I am a crossdresser and this is the story of a wild wild night! HI. My name is Leslie, I am a very dedicated crossdresser. I have to live as a male by day because of work. At night I usually get home pop open a beer and pop a buttplug in my juicy hole, get on the computer and watching some dirty naughty things until I just have to dres...

A Night to Remember Ch. 02

by Master_and_Sex_Kitten on Sep 16, 2017
Transsexuals & Crossdressers

Happy Birthday to me...Friday April 24th was my four year anniversary of joining Literotica.com, so as a special treat, four new stories in one go! * Author's note: If you haven't read part one -- A Night To Remember -- that might help provide a little context :P this is a transsexual story about love, confusion and exploring a new world of sex. Enjoy! --...

The Rental House

by PorscheKaru on Sep 15, 2017
Transsexuals & Crossdressers

I own a rental house in a city nearby. Actually its about an hour and a half away and it just became vacant. I needed to go down and inspect and clean it and fix anything needed fixing so I could rent it out again. Being so far away I planned to stay there while working on it so I brought an air mattress, blankets, pillow, and clothes. I also brought a duffl...

Text Conversation Shorts

on Apr 22, 2025

Read or create stories taking place in a text Conversation filled with dirty talk and photos. These can be tales of seduction, cheating, ****, cucking, or whatever else the imagination come up with. Tales can be short one shots or a multiple chaptered story.What's next? Wannabe Alpha Male Loses Girlfriend To His Ex Ne...

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Gloryhole Event

by carriekitty on Apr 22, 2025

Well i decided to try something new for a change, I spoke to Kerry (friend from previous stories) and she told me that there was a greedy girl event going on this Friday night, Carl was out with his friends and I had nothing planned, so I thought I'd go down and see what's going on. So Friday soon came and I got freshened up, put on some smart casual clothin...

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Dirty Chrissy Goes to College Ch. 4

by DirtyChrissy on Sep 13, 2017
Erotic Couplings

After my boyfriend Rob introduced me to the wonders of sex in video peep booths and gloryholes, our sex life heated up even more. Now, when we would fuck, Rob and I would relive the experience. One night, while fucking my pussy doggy style, he reached around and diddled my clit with his fingers and whispered in my ear, "Is this how that stranger touched your...

Gloryhole Addiction Ch. 02

by Brittni4u on Dec 19, 2018
Fetish

It has been a several years since my dirty yet amazing gloryhole experience. At that time, I was 18 years old and still in high school. It was supposed to be a sneaky one time experimentation which turned into a nine month long, multi-visit, wonderful cock sucking experience that has never left my memory. I have always had an oral fixation when it comes to...

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

How I Became a Crossdresser

by Chrispe69 on Sep 16, 2017
Transsexuals & Crossdressers

I've always loved everything about women. I love their curvy feminine features, their long painted fingernails, the high heels they wear and their silky smooth clothing. When I was young, I liked the women I dated to be flashy and slutty looking. I never had much trouble getting the sex I was after from these women either. I got married in my late twenties...

Literotica Monthly Awards 2020: July

by Literotica on Oct 5, 2020
Loving Wives

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of July's Reader's Choice Awards. First Place ($150 Cash Prize Winner):S'mores Ch. 04 - Forever Please by BookwormmomSecond Place ($100 Cash Prize Winner):Home for Ho...