Sissy Tim Stories

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The Awakening of a Sissy Pt. 09

by sissyjolie4u on Apr 13, 2020
Transgender & Crossdressers

Mistress Di pulled her car into her garage and instructed me that I was to immediately go prepare myself for the evening. "Remember to douche extra well for your evening time with Tim," she added. "Who knows what Tim might have planned for you tonight Jolie." She said that while winking at me. My mind was full of thoughts as I made my way to the bedroom. W...

The Awakening of a Sissy Pt. 10

by sissyjolie4u on May 11, 2020
Transgender & Crossdressers

Best I could tell, neither one of us had moved an inch from the position that we fell asleep in. The urge to pee woke me quite early, like 4 AM early. A smile came to my face as I realized I was still holding Tim's cock. While barely awake, I made my way to the bathroom and took a seat to pee. While sitting there peeing, it hit me that I should probably do a...

AliExpress and Sissy Downfall Pt. 04

by His_fag_wife on Dec 30, 2017
Transsexuals & Crossdressers

As Tim added inch after inch, slowly taking his time, stretching his new slut, driving deep into Emma's tight twitching arse, she moaned with the pain like a wounded animal. He loved the supremely tight fit as he slid forward into her, bit by bit. His sweaty ball sack finally rested on Charlies face, each of his big balls settling into Charlies eyes sockets...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

The Awakening of a Sissy Pt. 06

by sissyjolie4u on Mar 2, 2020
Transgender & Crossdressers

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You ha...

The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

AliExpress and Sissy Downfall Pt. 09

by His_fag_wife on Aug 20, 2018
Transsexuals & Crossdressers

Charlie stood wobbling slightly, on the 5 inch heels. Legs a little apart to accommodate the very substantial base of the Fenrir Dragon cock currently stretching her wide open, holding her buttocks apart and her asspussy wide open with the 2 1/2 inch diameter. She felt better now, shattered and tired but she was basking in the looks of approval from both her...

AliExpress and Sissy Downfall Pt. 05

by His_fag_wife on Feb 6, 2018
Transsexuals & Crossdressers

Charlie was deep in it now, being assessed by Miss Bell the beautician before she started work on removing all of Charlies hair below her soon to be plucked eye line. Candice the young pretty petite receptionist was also looking on to deepen Charlies humiliation. "Miss Bell, I'm really tight, but even my little pussy couldn't be satisfied by that little cli...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

You're Like a Little Boy at Times Ch. 03

by Myneed on Aug 30, 2017
Fetish

This is a slight twisted femdom love story that will make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** My heart ached for Mel. It had been another long week another long week of edging and chastity at Mel's instruction. Th...