Sissy Tim Stories

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Orientation
Length
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Infinite Scroll

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

AliExpress and Sissy Downfall Pt. 07

by His_fag_wife on Apr 9, 2018
Transsexuals & Crossdressers

Please for goodness sake don't read this story if extreme use of submissive males by dominant males and dominant females offends you. This is pure fantasy and at the darker end of the spectrum of stories on Literotica, please do not read if this is not your sort of thing. Otherwise I hope you enjoy the spiral of depravity. ***** Charlie was alone in the ro...

May Ch. 01

by Jack1107 on Oct 31, 2018
Mature

Jack was in his last term at University before his finals at the end of May. Easter had been early this year. His mum, Jean, had asked her friend May if Jack could stay with her Monday to Friday for the last term as her Town House was a two-minute walk from the University. Jack had a fifty-minute drive to it then another fifty-minute drive home in the evenin...

Opening Him Up Ch. 03

by humbleboy on Sep 12, 2017
BDSM

Amy laid down next to Tim exhausted. “Tim, now I want you to suck on ALL that cum you just shot in my pussy.” Tim without a word placed his mouth on her trimmed pussy and began to suck and lick her hot organ. “That's good. You love this pussy, don't you?” Amy had always liked the way her husband eat her out, but now it was the power trip getting her off. “D...

AliExpress and Sissy Downfall Pt. 02

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

Charlie had really done it this time, deciding on his first big self bondage session in his hotel room after picking up all his kinky goodies he bought on AliExpress. Then his wife had surprised him by joining him for the weekend and found him, fully dressed as a Sissy slut, make up, wigs, high heels the lot. Locked in bondage at his own hands. Now she was a...

AliExpress and Sissy Downfall Pt. 08

by His_fag_wife on Jul 10, 2018
Transsexuals & Crossdressers

Emma's gaze swung around the room taking in as much of the contents of the room as she could. So many of the items being completely unrecognizable to her. "Close your mouth my dear little slut or I may have to put something in it." "Yes Master, sorry Master, it is just an amazing collection." "It is, isn't it and we'll get Charlie to choose your new plug...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

A Sissy Shopping Trip Ch. 01

by cwsissy on Sep 16, 2017
Fetish

My wife, Cindy, and I were in the bedroom getting dressed for a party at Tim and Karen's place. They were good friends that we had known for even before our marriage four years earlier, with whom we had shared a lot of good times, including many a camping trip and tipsy card game, always with plenty of hot talk rife with innuendo. Well, technically, Cindy w...

What Just Happened? Ch. 04

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 04 -- I am no longer in control I looked at Beth and so did the pizza guy. The delivery guy started a discussion by saying, I do not want to offend you girls, but you are both very attractive and I see one of you has panties on because I can see them. So the other panties on the floor must be yours he said as he looked at me. What is Beth doing st...

Opening Him Up Ch. 02

by humbleboy on Sep 12, 2017
BDSM

Amy was looking down on her husband, watching the large life like phallus enter into his mouth. She got the strap-on in four inches and then Tim started to choke. "Relax my little bitch and try to think of swallowing my cock." Tim tried and he eventually gained another inch, but for fear of this new sensation he wouldn't go all the way. "Don't worry, I'm goi...