Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

From Princess – Mistress

by subway1962 on Sep 17, 2017
BDSM

This all started about 6 months ago on a Saturday afternoon, my wife had said that she would be out all day, shopping with her friend, then she was going to the cinema to watch a film and said she would be back about 10pm. My little princess (Ana) was having a sleepover with her friends so she was out for the night, that's when I realized I would be by myse...

Subliminal Obsessions Ch. 07

by Sissyhalo on May 28, 2018
Transsexuals & Crossdressers

*Before... But this, this is the big turning point because this, this as hot and as intense as it because it settled into lovemaking and being made love to by this amazing guy that honestly could have all the pussy he ever wants and he's with me. With me making love to me and it's so much more than sex to me right now. And honestly. Really fucking honest...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

Princess Mia Ch. 03

by rossdrakon on Sep 14, 2017
BDSM

First, I would like to thank "B. Smith." For editing the story and for your advice. I also want to thank the readers for your encouraging words. I will try my best to improve on the stories and writing. The story is based on real life experience. This is a story about a guy who found the perfect dominant woman that makes him truly happy. Story would be mor...

A Night at the Club Pt. 01

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

Dani nervously looked at his reflection in his trusty compact mirror. He was sitting in the passenger seat of Keyshawn's black Escalade, about to enter one of the most exclusive clubs in the city. His mascara made his naturally thick eyelashes flutter attractively, his eyeliner perfectly framed his blue eyes, and his Candy Apple lipstick was flawlessly appli...

Fifi La Femme: A Pansy at Last Ch. 02

by pris69696 on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 2- Missing Big Frank Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me to marry him; to be his gay wi...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...

Ginger the Living Sex Doll

by njcaptionlover on Sep 16, 2017
Transsexuals & Crossdressers

Growing up I've always felt like I was born the wrong sex. That I should have been a girl rather than a boy. However, living in a traditional family where I was made to suppress these feelings. The majority of my teens were spent trying to be boy and not the girl I wanted to be. After turning 18 years old, I moved out of my parents' house and decided to li...

A Disturbing Desire

by Cirkle7 on May 28, 2019
Transgender & Crossdressers

Of course everyone mentioned in this story is over eighteen years old. If you are under that magical age read no more. Also if gay desires, cross dressing, interracial relationships or anything along those lines offends ... please finds another story short many good authors here. This is my first story so please be gentle. ***** Last week my mistress sent...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...