Shemale Maid Stories

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Infinite Scroll

The Gym Ch. 4

by Kip Carson on Sep 14, 2017
Group Sex

John arrived at Kate's house at 6:50 pm. She answered the door in a very tight fitting short dress. "Damn, you look good" John told her. "Sorry I'm so early, but I was so excited about tonight" he added. "That's fine, I'm always ready early" she said. "And you look pretty damn good, too" she added. She eyed him up and down. He was wearing black dockers, a ni...

Coerced Ch. 02

by HorribleHenry on Jul 27, 2020
Transgender & Crossdressers

The prison governor, using Mikel as his interpreter, was very keen indeed that I should not return to America and make a terrific fuss about my enforced feminisation. I would not have put it past him to have arranged for my quiet assassination in order to permanently hide the fact that, during my six month's incarceration in his prison, I had been physically...

He is Your Master Now Pt. 03

by DomAlphamann on Jun 8, 2020
Transgender & Crossdressers

With seemingly no way out of his predicament, Ambrose Sweet clings to the hope that he might at be able to influence his ultimate fate, though he has no idea what that fate might be, or the true nature and scope of Cassilda's abilities and ultimate aims. Part 3: Crawling to Oblivion From the moment Cassilda told Ambrose "No erections until I see you again"...

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Pam's Shemale Experience Ch. 09

by majicman21 on Aug 7, 2019
Transgender & Crossdressers

It was Tuesday morning, the second day of the weeklong teacher's conference, and almost the entire room was paying close attention to the speaker, one Martin Greenman, forty-seven-year veteran of the classroom and expert in educational theory. The only one not paying attention was Pam. She was in the front row, doing her best to listen and sit still. Next...

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,...

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 Devil's Harem Outfit

by Miles63 on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: Hey guys, when I was finishing my last story I found a file with this story half finished and I thought, what the hell lets finish it. Now this is a very very dark story with strong erotic horror themes that some may not find pleasing. There is some strong incest thrown in too. If you are not into that this may not be the story for you. Other...

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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Connie Finds a Kinky Boyfriend

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. For those of you who have read my other adventures, this story is will be told in a...