Shemale Gloryhole Stories

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Pam's Shemale Experience Ch. 12

by majicman21 on Oct 12, 2020
Transgender & Crossdressers

Pam and Alex sat together on the bed, the former watching television, the latter on her phone. It was their last night at the hotel. Some of the teachers at the conference had organized a group outing earlier in the night to a nearby restaurant for dinner and drinks, as a farewell of sorts. Pam had gone along, but Tanya had been unable to. "I have a date,...

Sorority Gangbang Sisters

by HeyAll on Sep 25, 2017
Group Sex

Part 1 of 4: The Pledge Emily stood nervously. She was the youngest person in the room full of people. A fresh faced 18-year old who was new to the college system. Her hair was tied in a ponytail. Her thick framed glasses made her look like a nerd. But she tried to be unafraid. She tried to be strong and brave. "Why should we allow you to pledge?" Morgan...

Late Night at the Campgrounds

by AnthonyBlackLit on Apr 14, 2020
Mature

Uncomfortable. Again. Drew Collins had been tossing and turning in his overpriced sleeping bag for what felt like the better part of the whole night. He groans. Another uncomfortable night sleeping in a tent on the hard ground. Drew was on one of his yearly family friends camping trips. The sort of trips people take with old family friends. Drew slips on hi...

The Sexiest Shemales Ch. 03

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

I woke up laying on Daisy's inner thigh. Her cock was lying right in front of my face. It smelled so good. It smelled like sweet perfume and cum from our previous romp. I smelled it and began rubbing the tip of my nose on it and then slowly I began kissing it. Daisy began to slowly wake up and did her cock. It grew more and more as I continued to kiss it and...

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...

The Booth

by NikkiKush on Aug 19, 2017
Exhibitionist & Voyeur

She really had no idea what she was in for, but the large dildo display that was located right inside the front door let her know it was at least going to be dirty. She liked dirty. She was dressed for dirty in a skirt that stretched across her luscious ass, and a top that dove all the way down her deep cleavage. Her body was the very definition of rubenesqu...

Hot Massage

by william125 on Sep 26, 2017
Transsexual

It's been a busy day at the spa. You decided to stay on working at the spa in your university town over the summer break rather than move back in with your parents. The spa offered an excellent training program for new starters and you found you were a natural. You quickly went from collecting used towels to massaging regular clients. As you wash the oil fro...

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Freak Daddy

by DickThePimp on Jul 6, 2020
Celebrities & Fan Fiction

Keeping it simple... And freaky... Parody... Offensive, but fun... For perverted entertainment purposes only... It's fuck time, bitches... You ever freak a bitch while your sweet mama makes you breakfast? I did just now. My girl Rosario Dawson strolled her fine Puerto Rican ass into the kitchen all nude and shit... Except for her gold and diamonds FREAK ch...

Beth Gets a BBC at the Gloryhole

by bethslover on Dec 9, 2019
Group Sex

[Comment: Beth is my girlfriend! We have a lot of kinky fantasies, but recognize that many of them are unrealistic/impractical for carrying out in real life. To cope, we've decided to write them out together. This story was based on two requests by literotica readers left on my previous story, 'Beth Gets Seduced by Gym-Bros'. You don't have to have read that...

Visiting a Gloryhole

by BuckyDuckman on Sep 13, 2017
How To

Gloryholes. Are they real? How do I find one? What's it like to visit one? Is there an etiquette to follow? Are they safe? Are they real? Yes! I've visited several of them. How many? I didn't keep count. Ten? Fifteen? I don't know. I've visited them from Philly to St. Louis to Florida and lots of places in between. Deploy the power of the internet to search...