Sissy Gym Stories

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Julie's Collaring Ceremony Pt. 01

by julieaugust72 on Dec 24, 2019
Transgender & Crossdressers

Please allow me to introduce myself. My name is Julie and I am a very submissive older sissy. I am 5-9, with a soft feminine body. I have been taking fem pills for years now. They have given me a feminine shape with a nice soft arse and 36C tits. I work out very hard in the gym to keep my body tight. But I still have a bit of a belly which people that the me...

Ami Gattson's Slave Stable

by profperverse on Jul 27, 2020
Fetish

I reported to the home of Ami Gattson as I had been ordered to do. I had a nervous feeling of anticipation as I approached my new situation. Just earlier today during lunch I learned that Susan Russo had "sold" me to Ami for the price of a lunch and a slave girl Susan was getting for me. I understood that Ami had another male slave and a female. My role in...

Young Master Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a ch...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

The Awakening of a Sissy Pt. 04

by sissyjolie4u on Jan 27, 2020
Transgender & Crossdressers

After a long evening of studying, practicing, and of course grooming myself, I woke to a message from Mistress. The message read; Sissy Jolie, douche your pussy, bath yourself, and be ready to meet. Make sure you douche and your trainer is inserted. I'll be over around 11 and I expect you to be in matching bra, panties and your heels. Also, ensure your cocks...

A Little Bit Feminine

by ThatGuyMan on May 12, 2020
Transgender & Crossdressers

"Are you sure I can't help?" The reply was cut short by the sound of Jason retching once again. The sound came from their bathroom at the end of the bed, where it had for the last five minutes. Tammy leaned up in bed, concern on her face, as she made to kick the sheets off and go help her husband. Jason, ears like a hawk despite currently revisiting last n...

A Christmas Tail Ch. 03

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

The following story is written by my wife Angel. It is her view of the slave auction night plus my night as her slave and what she made me do. As I rode home in our car that night, a bit dazed, and reflecting on what the hell had just happened, I was surprisingly pleased with myself. I really had showed, mostly to myself, but also of course to my husband...

Sissy Sauna

by Queen_Diana on Nov 16, 2020
Transsexual

Tommy fidgets a bit as he passes through the automated doors and into the air conditioned gym. People mill about, ranging from those who have clearly been in the gym for months on end, and those that have clearly just started. Tommy was in the middle. Anxiety and fear well up inside of him for a split second, his field of vision narrowing down into a thin fi...

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Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

Sarah was Naughty in the Sauna

by SarahCD on Jan 16, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...