Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

The Sexy Cuckold Couple Pt. 06

by cuckcpl4play on Sep 19, 2017
Loving Wives

My New Life at Work...First Week Continues Part 6 I arrived home that evening (Monday) and felt exhausted by the roller coaster ride we had experienced over such a brief period of time. It brought me great comfort that Master must have some good intuition as allowing me to get home and be in my wife's arms, his slut's arms, tonight was truly needed. Also, o...

Cucky Trained by CD DOM Pt. 04

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

At 7:00pm you arrived in my room. You were fully dressed and looking very good. I sat you down and did your make-up and hair. Since your original wig was still splattered with cum I picked you out a different one. Similar in style but brunette. You looked like a totally different whore. "We are going to have company tonight, slut. You will greet our guests...

Caught In Lingerie Ch. 02

by hicutlover on Mar 5, 2018
Transsexuals & Crossdressers

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right...

AliExpress and Sissy Downfall Pt. 10

by His_fag_wife on Jan 23, 2019
Transgender & Crossdressers

As Charlie with her head raised off the cushion admired her new sissy pussy, she felt a complete head rush. As she and Tim had discussed just one guiche piercing at such length, over and over, texts flying back and forth on the crest of a wave of horniness and a submissives deep desire to please, she had fixated on the idea of being pierced without her wife...

An Invitation

by Divadaze on Sep 16, 2017
Transsexuals & Crossdressers

"Oh come on,Sarah. There has to be a way." An innocuous enough statement, but that's how it all started. I'd just received an invite to Cressida's annual Christmas party which, maybe not on the Hollywood A list, was within the cognoscenti an occasion not to be missed. The soirees of this director and major shareholder of a left leaning and decidedly outré...

The Awakening of a Sissy Pt. 08

by sissyjolie4u on Mar 30, 2020
Transgender & Crossdressers

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we...

Opening Him Up Ch. 01

by humbleboy on Sep 12, 2017
BDSM

"How would you feel if I used a strap-on, on you?" Amy looked at Tim with a mischievous smile. "I don't know." Tim was a little nervous, and he looked at how nice Amy was, lying there naked and beautiful next to him. She had a petite body, and very soft skin, a tight pussy, and now Tim started to image this girl, wrapped in leather wanting to take his ass....

Euphoria Resort

by sissyashley4bbc on May 4, 2020
Transgender & Crossdressers

"Welcome to Euphoria!" a good looking black man said as he greeted my wife, Jess, and I. I couldn't help but notice two scantily clad maids getting our bags for us. "Come right thus way to check-in with your specialist," he directed us. We clutched each others hands and hurried in, we were giddy to get started. Euphoria was no ordinary resort, it was cou...

You're Like a Little Boy at Times Ch. 04

by Myneed on Oct 11, 2017
Fetish

This is a femdom love story that will make most sense if the chapters are read in order. James is becoming helpless as Mel dominates him and molds him to her will. 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 Chapter 4 I received a flyer in the mail. Nowdays it is unusual to...

Sally, Tim have Elderly Neighbours Ch. 01

by MaryGrangerx43 on Oct 15, 2018
Fetish

This story is a complete fantasy and no association with real life whatsoever. No one is under the age of 20 and there is no physical hurt or pain. ***** Chapter 1 - Introduction My name is Sally Banks and I am 28 years of age and have been married for over 7 years to my husband Timothy Banks. We have always been reasonably happy, but over the last 12 mon...