Shemale Fucks Boy Stories

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Shemales on Vacation

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

Shemales on Vacation or Fun in the Sun, When Boys Will Be Girls! ****** Chapter One - Cum Fly With Me! Teri Nolan and Brenda Vink giggled to each other as they whispered excitedly between them. It was hard to pay attention to the movie showing at the front of the cabin on their long flight across country to California. Their minds were on their sorori...

Magic Whore Ch. 04

by KinkyMuffin on Sep 19, 2017
Sci-Fi & Fantasy

He took my robe off. I looked away and he started rubbing my tits and then my cock. I started to harder when he moved to my pussy. I groaned as I got wetter. "For a boy, you make such an eager little slut," He whispered in my ear, "I'll just have to parade you around town." He lead me into the bed room and put me into a demi bra and a skimpy pair of pant...

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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A Dream?

by njcaptionlover on Sep 16, 2017
Transsexuals & Crossdressers

I nervously paced back and forth in my home waiting for the escort that I had called for while constantly checking my breath to see if it smelled good as well as my body. I felt like taking another shower but was worried that the escort would arrive while I was in the shower. As I continued to pace I wondered what she would look like, hoping that she was as...

Create a Shemale

by wsauthor on Sep 29, 2018
Science Fiction

*Author’s note: This story is Public, if you have an idea, start writing!* Robots, science and chemistry have all advanced further than the public is aware of. Due to patents and trade secrets, nobody knew it was even possible to create a sex bot. They can have gravity defying shapes and sizes. They can even alter their owner with chemical cocktails. Cockbot...

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Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

Time Travel

by Coolcockdude on Aug 17, 2020
Science Fiction

Choose your Gender Alex - Boy 22 Year Old virgin with a big dick. Alexa - Girl 22 year old virgin with busty boobs and tight ass.What's next? Boy - Alex Girl - Alexa What's next? Boy - Alex Girl - Alexa...

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A Shemale Vacation Ch. 02

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragement, very quickly changed in demeanour when he discovered we...