Shemale Fucks Guy Stories

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Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Chrysalis of Kirsten

by KirstenEclipse on Mar 23, 2019
Transsexual

Date: March 22, 2019 Author: Kirsten Addison Subject: Chrysalis of Kirsten Chapter 1 By KirstensubTS My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transsexual slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been c...

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End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Yet Another Shemale Tale Ch. 03

by DonScott on Oct 12, 2020
Transgender & Crossdressers

"That was very nice," Mia said as she wiped a drop of gravy from her cute red lips, "shall I wash up?" "Not now," I told her, "let's go into the lounge and have a drink." We got up from the kitchen table and as she walked out of the room I uncorked a bottle of red and picked out two glasses. "I have been here nearly two days," she said with a giggle as I...

Ashley's Misadventures Ch. 02

by redking99 on Sep 14, 2017
Group Sex

Ashley is gently stirred awake by something warm, gently rubbing her exposed clit. She moans softly, wondering if she is still dreaming. Her dreams are erotic of late. Her desires and wants greatly heightened just from her dreams. Her pussy remains almost permanently moist. She moans again, louder this time, as the fingers on her clit begin a slightly more v...

Marilyn at the Movies

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

So, after about a bit of a hiatus, the shemale that you love is back. Well, at least I love her. After all she is an alter ego for me. Now if I could parlay that into some cash, I’d be good to go. Anyway, it’s good to be back in the saddle, especially the way college has been getting to me. This story, and the next few I plan on writing, will be stroke stori...

The Docks

by threep on Sep 17, 2017
Loving Wives

I pull the car up into a spot near the darkest end of the dock parking lot, roll down the windows, and shut it off. Now we just wait. My wife's hands tremble a little as she adjusts her shirt and pulls down on her skirt a little (to no avail -- it's far too short). She's wearing a schoolgirl outfit: hoop earrings, a white blouse tied just under her chest wi...

Finding Love Where You Can

by NerdySex on Dec 18, 2018
Loving Wives

It was a month after I started my new job. The guys encouraged me to meet others from the company. Elmer's Kitchen and Bar was the place to be on Friday nights. Upwards of one hundred younger people from my company usually showed up. Mike and Steve, guys on my project team, did introductions. There was one girl in particular that caught my eye. Young, blond...

Nadine's Night Out Ch. 01

by redking99 on Sep 16, 2017
Erotic Couplings

Nadine, oh Nadine. A beautiful, sensual, Filipino woman. Fair skinned, almost perfect complexion. Standing at about 5 foot 6 on those great, shapely, legs. 34C bustline looking great on her slim frame and a rear end which juts out prominently but not large as to overwhelm. She has a bubbly and rather sexy personality, sometimes flirting, sometimes just playi...

A Special Girl

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the small town that I came from. I'm from Fitchburg, by the way. I...