Sissy Boyfriend Stories

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Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

Thirty Days to Jenny Ch. 2

by monika ikon on Sep 12, 2017
Transsexuals & Crossdressers

day eleven Well, Alison, thought, Jeff had been listening to the 30 Days to Jenny tape for ten days already and the changes in his character were dramatic. He was sweeter, more helpful around the apartment, and even more satisfying in bed. He'd started a diet, been exercising, and had taken a renewed interest in his appearance. If the changes stopped there,...

Neighborly Relations Pt. 03

by grizzley123 on Feb 11, 2019
Fetish

Author's Note: As is true with all of my stories, this is a fantasy. The themes and ideas I find erotic might be different than yours, that's ok. Please leave comments, my ego will appreciate the positive ones, the writer in me will enjoy the constructive ones, and the submissive side of me will accept the berating ones. Enjoy! *********** It is best to re...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

Turned into a Slut Ch. 04

by xaitonnar22 on Sep 19, 2017
BDSM

After grabbing some quick sandwiches, Jennifer and I returned to her home. We found a note on the kitchen table from her parents letting us know that they would once again be out of the house for dinner. They didn't expect to be back until ten o'clock, it was seven right now. Once in her room, Jennifer commanded me to strip out of my jeans and bend over the...

The Man That Owns Me Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Don't be shy. Pull your panties down, baby boy. Show the man that cute little thing." He laughs, smiles at me. He's seated on the couch next to a man I've never seen before. When they entered my house I expected only him. I hurry to do as told. It's something that is part of me now. I never hesitate to do as he orders, dominant of otherwise. He owns me com...

From Husband to Man's Sissy Wife Ch. 02

by Pantypansy on Jul 9, 2019
Transgender & Crossdressers

I had just finished changing into a black satin, frilly French maid's outfit - which Hamish had picked for me - when I heard voices downstairs. I pulled my silk panties up tight and put on a pair of black high heels and tottered down the stairs. Hamish had changed into jeans and a button-down shirt, and was chatting to my wife in the kitchen. Both were l...

Lulu's Lockdown Diary

by lululuvsblack on Jul 6, 2020
Transgender & Crossdressers

Day 1 So, with this virus we've all been told to stay home and not have any physical contact with people outside, not get together in groups at all, and not even step out of the house if not completely essential. We're locked down. I guess it wasn't a great time to move in with a couple of guys I barely know, but there you go. There's nothing I can do about...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

Jack's Bully Ch. 04

by Alpacawreck on Sep 5, 2018
Fetish

Jack woke up in the morning and was greeted to a beautiful sight. He watched Emily sleeping and was glad the day before wasn't just a dream. He reflected on how things had developed so fast and it was all thanks to Matt and his cock. As he thought of Matt's huge cock he noticed his clit had started to harden. He looked back over at Emily wondering if she wou...