Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Three Strikes And A Home Run

by SW_MO_Hermit on Sep 14, 2017
Loving Wives

I walked out of the courthouse a free man once more. My heart was heavy but my anger was subsiding. To my surprise I hadn't gotten screwed too badly this time. I headed for the public parking lot and my trusty old F150. It was a forty mile drive home and I really needed to get on the road. My children would be home from school soon and I needed to be there f...

You're Like a Little Boy at Times Ch. 05

by Myneed on Oct 13, 2017
Fetish

This is a slightly twisted femdom love story of James and Mel, his Mistress. It will make most sense if the chapters are read in order. In the last chapter, Mel's boyfriend, Tim, left the costume party with Tiffany. Mel made James, who is dressed as a girl, cum in public. I hope you are enjoying the series. All characters are over 18. ***** The party co...

The Training of Sissy Paula

by submissive~pet~ on Sep 14, 2017
Fetish

The Training of sissy slave Paula... Hello everyone I would love to share a story with you. I had just recently told a slave to leave me and never come back. He was not up to my standards, so I no longer had any use in him being my slave. There for I began a search for one that would be obedient and serve all my desires and needs. It began with me...

My Girlfriend's Sissy Roommate Ch. 04

by SEVERUSMAX on Nov 21, 2017
First Time

"So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it's between you and Rain, and I think that it's rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn't go so far as to call him a cuckold in the typical...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

The Sexy Cuckold Couple Pt. 09

by cuckcpl4play on Sep 19, 2017
Fetish

Part 8: The Ceremony We arrived home and almost like clockwork, a text came in to Miss Jenny's cell as we pulled up the drive. Master's text read...time is fleeting slut so you will have visitor's at your place shortly to help with your final task before dressing and officially submitting and devoting yourself to me as my owned slut Oh, and make sure slave...

The Artist

by uppishcarrot on Aug 31, 2017
Fetish

Tina was an artist. At 28, she owned her own art gallery in a posh area in the city. She was smart, outgoing and overly confident. Tall, brunette, blue eyed, she could melt a cheese sandwich from across the room. I met her on opening night. The company I worked for was having a Christmas party and it was to be held at Tina's gallery. It was a great atmosph...

My Girlfriend's Sissy Roommate Ch. 05

by SEVERUSMAX on Nov 24, 2017
Group Sex

I awoke from my half-drunken sleep to the sound of sex, and God, it was a fantastic noise! I could feel the vibrations on the bed as Larissa rode Rain, plus I could hear her moans as she took him balls deep inside her cunt. She looked at me as she saw me rise, gesturing for something, and sure enough, she wanted it in her ass. It was a dream come true, and I...

Catwoman Prowling

by cindy_4u on Sep 14, 2017
Erotic Couplings

2 years back for Haloween I was dressed slutty as usual. My costume for that year was Cat Woman. A tight body suit held with a clasp behind my neck, a zip on my ass to keep it tight around my waist and criss-cross strands that exposed my back and abs. Boots, mask, whip, the works. The tight body suit complemented my tiny frame to show every one that I had n...

Miracle Cure

by sharkinlace on Sep 12, 2017
Transsexuals & Crossdressers

I always had trouble with girls. Growing up I was a little bit introverted, which made socializing with people I didn't know a bit of a chore. But I never knew how to act around girls especially. Even when I was able to find the courage to talk to them, most of the time they just wanted to be friends. And the few times I actually went out on dates ended eith...