Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Natural Escalation

by WatchingAndWaiting on Aug 18, 2017
Fetish

Tim looked over at Lisa. Her eyes were half closed, but she noticed him looking, and her lips curved into a lascivious smile before the pressure from behind surprised her and she shut her eyes in ecstasy, pushing back and raising her ass a little to meet the massive cock burying itself inside her rectum. Tim felt his cock twitch a little, pressed against the...

Tell Me

by monika ikon on Sep 16, 2017
Transsexuals & Crossdressers

It was a Friday night, in the middle of summer, and I didn't know it but my life was about to change forever. I had just come in from a quick before-dinner dip in the pool. Wendy greeted me with a drink and a sexy little smile that told me she was in the mood to fool around. I was beat from a very hard day at the office and a long hot commute home from the...

My Girlfriend's Sissy Roommate

by SEVERUSMAX on Sep 15, 2017
Transsexuals & Crossdressers

"Look, Stan, there's ... there's something that I have to tell you and explain. It's not easy. In fact, it's very fucking weird, even to me, even while I've been letting it happen. I have to level with you, because, well, you and I have been flirting for a good while now and I'm smart enough to realize that you want me. Hell, I want you, too. This is very .....

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...

A Sissy Shopping Trip Ch. 02

by cwsissy on Sep 16, 2017
Fetish

At the car, I headed for the driver's side as Cindy opened the passenger door. Before I could take more than the first step her almost shouted exclamation, "Excuse me!" stopped me in my tracks. I looking warily at her, wondering what was wrong. "Come on," she smiled tightly, "girls ride over here. I'll take care of the driving today." My macho pride rebelled...

The Awakening

by catalina_francisco on Sep 17, 2017
BDSM

Pulling my tight skirt quickly over my arse, I managed to try to look sweet and innocent as my Master opened the front door to His house. We had not been expecting any visitors, so were surprised to hear a knock, just as He filled my arsehole with His thick, hot cum. Trying to appear relaxed was a little difficult as I felt my own honey dribbling down my thi...

Dot Makes Tim a Cuckold Ch. 07

by wantwhitewomen on Sep 19, 2017
Loving Wives

Just incase you forgot, this is a story about a black man who is fucking a white woman. It is also a story about the husband who is now a cuckold. The HUSBAND wanted to be a cuckold!! Please understand, it's not against the husband's will, HE WANTS IT!! Enough said, read it if you like this type of story. Don't read it if you don't like this type of story. I...

A Little Bit Cuntry

by AussieKev1 on May 13, 2020
Mature

3 years ago, when I was 56, I was posted to a job in the NSW country town of Dubbo, for 3 months. I enjoy my country postings. I receive a generous allowance that pays for accommodation and meals and if I get to keep what's left over. I was also looking forward to this posting because it gave me a chance to catch up with a friend from my teens and twenties...

Caught and Hypnotized

by Miles63 on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: First of all, I just want to apologize for anyone wanting the continuation to my other story, it is coming but I'm currently editing my novel so that has taken priority. While searching for some notes on my book, I found this story I wrote years ago for a friend. I thought it was lost as some files got deleted from my Computer few years back...

Marriage Transformation Ch. 10

by jealouscuck on Feb 13, 2018
Fetish

After their night of sex with Tim, Chris and Elizabeth had a light lunch and retired to the pool. They had one more night before they would go home on Sunday. At first, they just relaxed in the sun. Later, they noticed Tim come into the pool area with some of his bachelor party friends. Chris noticed that most of the guys were stealing glances at them. They...