Timmy Stories

876 results
Orientation
Length
Source
Infinite Scroll

Let's Make Timmy Taller

by Baba8 on Sep 1, 2017
Humor & Satire

Timmy was a conservative Airman. He served three years of his four year Air Force hitch in the Philippines. He spent his free time in the first bar that you see as you exit the base bus in the town of Balibago outside of Clark AFB. (The eruption of Mount Pinatubo killed the base) You could almost hit the main gate with a beer bottle. He never got to MacArthu...

Prison Guard

by passionatepoet on Sep 17, 2017
Mature

Jenny was a guard at a men's correctional prison. She was very kinky and she loved to fuck. Timmy was an inmate at the prison and he was mentally challenged. He also had a very large cock that was noticeably seen bulging from the uniform khaki pants he wore. Timmy's bulge caught Jenny's eye on several occasions and she would go into the women's restroom of t...

The Best Milf Patricia Heaton

by DickThePimp on Aug 1, 2018
Celebrities & Fan Fiction

This is a parody... It is not real. *** Timmy rang the doorbell, of his neighbor across the street, Patricia Heaton. She had asked him to move some stuff from her basement. Her family was out of town and she was all alone, so she needed his help. Timmy is a good guy, 18 years old. He was preparing for college in the fall and he could use some extra cash, s...

Stone

by BrainGym on Sep 17, 2017
Loving Wives

I've been writing for a long time and I have published many works. This is my first story for Literotica; and what better category than Loving Wives? **************************************************** Timothy Leadbeater (known as Timmy to everyone) blew on his whistle. "Batter up!" He shouted to his softball team. He was coach and umpire to a bunch of ei...

Linda Gets Lucky at College Ch. 02

by Lrt83 on Apr 24, 2018
Mature

Six weeks had passed, and Linda and Jim had increased their relationship. He had moved into her large home and spent most of his nights there. Jim still had to attend fraternity parties and meetings. Linda went to some of the parties. At one of the annual alumni parties she got hit on by the older alumni than some of the girlfriends of the current members....

The New Girl

by winterflame on Sep 16, 2017
Transsexuals & Crossdressers

Timmy’s stomach fluttered with nervous excitement as he stepped off of the plane. He’d been waiting for this moment for years, and his first view of the island didn’t disappoint him at all. It wasn’t the lovely greenery or the brilliant sunset that left him in awe, although those delights did register dimly on his senses. The sight that had him so captivated...

Sex Kitten of the Month Pt. 05

by HerMatman on Nov 18, 2019
Erotic Couplings

It is raining outside the gymnasium on a Friday evening. Timmy (19 yrs.) is a handsome sandy-blonde competitive wrestler. He stands at 5'8" and weighs 149 lbs. His girlfriend never leaves his side. This out-of-town meet is the first time she'll miss a wrestling match. She dropped him off in the parking lot and drove away in her car. The athlete bus is alread...

Ask For It

by indentcouple on Sep 19, 2017
Loving Wives

I have to admit that I never, ever thought that I would be writing a story to a web site. My name is Joanie. I am 38 years old, 5'7", thick dark brown hair and a very womanly figure, with 38D breasts (for those of you who need to know) and wide, but very firm, athletic hips. I have been told that I have a perfect complexion. My very creamy white breasts are...

Summer Model Ch. 02

by kelly gatsby on Sep 19, 2017
Exhibitionist & Voyeur

"Come in Timmy," Laura said, opening the garage door where she had her photography studio. "I'm glad your here." Timmy entered, obviously nervous. He looked up at her, and then looked back down. Laura tipped him an extra $100.00 after their first photo session and she was glad to see him back. He was acting awkward again. Just like when they first met. "Y...

The First Time

by jjgarces on Sep 13, 2017
Celebrities & Fan Fiction

Kelsea Ballerini hadn't taken her rise to prominence in the country music world lightly, and the one thing she was quickly becoming known for was being personable with her fans. One of the ways in which she had done this recently was by taking a female cancer patient of hers to the CMA Awards as her date for the evening, and while it was something Kelsea di...