Shemale First Time Stories

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Jenna & Stephen Ch. 02

by Naf_Noparts on Sep 12, 2017
Transsexuals & Crossdressers

AUTHOR'S NOTE: My intention all along was to follow up with the progress in our relationship shortly after my original story, but so much has happened since that the story I'd start to write would be scrapped again and again. Here is the latest. Thank you so much to those of you who gave it such a high score, for your comments and constructive feedback, and...

How Dicks ended up in My Mouth Ch. 01

by ret123 on Sep 19, 2017
Transsexuals & Crossdressers

My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets. The story begins when m...

Mistress Melody's Wanton Evening

by RobinTVDaniels on Aug 18, 2017
Fetish

Mistress Melody had become my mistress recently and I was very deeply in love with her. Melody is not that tall but is a very sexy black woman with long braided hair. Her dominant personality was over six foot tall though. I was a transvestite submissive sissy and I was her total slave. We both knew my little 4 inch dick would never satisfy her so she had...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

Pounded Into Submission Ch. 02

by Jamesjones52 on Sep 12, 2017
Transsexuals & Crossdressers

*This is the prologue that leads up to Joe being "Pounded into Submission". Also, I read the comments about this being a repost. It is; I am the lonejackman. I got rid of my yahoo email account and couldn't get my password reset for here. * Two days ago Joseph was checking out porn like he usually did at his favorite site xhamster. A couple of BBW vids here...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

ShemalePrey.com

by Wazzfup73 on Apr 24, 2019
Transsexual

(Apologies that this is not in the Guidelines, but the term 'shemale' is used only for the purpose of erotic fiction and should not be as a term or to represent trans women in real life. Apologies to any people it may offend) As the alarm clock goes off on my phone and your mom shouts your name 'Ryan' to come down for breakfast I jump out off bed to look at...

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Shemale Shopping Spree

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

She-Male Shopping Spree featuring Chelsea and Victoria, two gorgeous chicks with dicks - and an attitude! by Mistress Tawny Suede "Oh god, I feel so incredibly horny!" said Victoria. "Well, sugar, if we hurry back to the apartment, I've got just the cure," said her best friend and roommate, Chelsea. Victoria looked the stunning black girl in the eye a...

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...