Free Shemale Stories

Shemale Prostate Orgasmic Bliss!!!!

if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... read more

ProstateMilker May 1, 2015 45%

Chapter 2 - Cuckold Cruise

If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope ... read more

Sissy Annabelle October 7, 2022 80%

The Weekend

The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... read more

MasterofSissies1 December 4, 2018 72%

Headmistress' Favorite Sport Part 3

There was no more time for Denise and Susanna to get over their chemically induced bout of incestuous activity as Denise was being sent to school. This was of course part of the plan. Slaves should always feel guilty about something and once their slave training was over, neither would be able to ma... read more

shemale lover December 12, 2011 87%

Headmistress' Favorite Sport Part 10

When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... read more

shemale lover December 13, 2011 100%

New Girl

'Hey girl, watcha doin?' To this day, I don't know why I answered like I did. 'It's Jess!' 'Pleased to meet you, Jess! I love that show too! You actually look like Jess from that show 'New Girl'!' 'You're kidding me, right dude? I don't look at all like Jess, and that is not even my ... read more

shemale lover December 22, 2012 100%

Adventure with a Couple

A friend of mine, who thinks that i lead an exciting sex life (okay, i DO, lol) has asked me to relate an incident from my experience where i had a session with a couple. So, R, here goes. i guess i should relate a bit about myself, so that you understand how this affair took place. i am a 41 yea... read more

shemale lover October 15, 2011 100%

Headmistress' Favorite Sport Part 9

When Denise returned from the academy all this was taking place without her knowing about it. She started her new life as a maid in Mistress Rachel and Master Tony's house alongside her mother, Susanna. Susanna had in the meantime developed into a complete slave, craving punishment and humiliatio... read more

shemale lover December 13, 2011 0%

Sissy School

I arrived at the school at 8AM for the start of my new life. The school had promised a lot when I saw their website but I wasn’t quite sure what I was in for. I had arrived dressed in male clothes with none of my belongings as I had been instructed to on the website. I walked through the gates into ... read more

Sissysophie780 July 4, 2019 69%

SISSY AWAKENING ⚧️ ⚧️

"Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleure amie et une femme que je connai... read more

Femboy 2021 March 25, 2023 50%

Darling Nikki

Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... read more

shemale lover July 15, 2012 100%

The House of Lesslie

I. The mansion hadn't changed, not all that much, from how I remembered it. If at all, it had aged gracefully, as only English mansions can ¬ a massive Edwardian building that had served Lords and Ladies, had housed masters and servants for centuries. Around it, at a respectful distance, w... read more

shemale lover October 14, 2011 66%

P.A. for a Day

The gates swung closed behind Charles as he slowly drove his car up the sweeping driveway. Even though he was looking forward to the erotic delights which were in store for him that day, the cares of the world seemed to weigh heavily on his shoulders. As he drove up to the garage he mused about t... read more

shemale lover September 5, 2012 0%

Headmistress' Favorite Sport Part 6

At Mistress Rachel and Master Tony's house Denise was pushed into the role of maid along side her mother, Susanna. Susanna had been reshaped exactly as Mistress Rachel wanted it. She was now a devoted little nymphomaniac slave who loved her mistress and master and who would do anything for them. Lik... read more

shemale lover December 13, 2011 100%

My Orgasm at work

I finally found my sexual fantasy come true at work. I always fantasize about one of my female co-workers (and sometimes all of them) dominating me, pegging me, brutalizing me. That every time they walk by my office, they would pour their coffee on my floor next to my feet and i'll get on my knee... read more

Chickzdigmeyup June 21, 2019 85%

Camming Down the Rabbit Hole Ch. 08

A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... read more

Dani_does_Dallas November 15, 2021 90%

Daddys Little Slut

I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... read more

aishacox January 31, 2023 100%

TRANSFORMATION DU SOUS-SOL DE ZOEY ⚧️ ⚧️

Jack a terminé son entraînement du matin en s'étirant. La sueur dégoulinait de ses muscles maigres alors que le chaud soleil matinal frappait la peau nue de sa poitrine. Il se pencha pour ramasser sa bouteille d'eau, reconnaissant pour une brise fraîche soudaine alors qu'il remontait la courte allée... read more

Femboy 2021 April 10, 2023 50%

Headmistress' Favorite Sport Part 11

Denise lay in the trunk of the car, her legs tied together with rubber straps waiting patiently to see what would become of her. She had long since relinquished all control over her own life and knowing that she was just useless sissy-slut made it easy to accept that whatever was done to her was pro... read more

shemale lover December 13, 2011 80%

Collette's Property

I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade ... read more

shemale lover December 19, 2012 90%