Girlfriend Bet Stories

104,405 results
Orientation
Length
Source
Infinite Scroll

Abby Pt. 01

by alexbrown1802 on Sep 13, 2017
Exhibitionist & Voyeur

Abby's alarm went off suddenly and she awoke with a groan... Damn. Six O'clock, already. She rolled over and hit the alarm button on her phone. She then sat up and yawning and rubbed the sleep from her eyes. She looked around at the mess that was her bedroom, it was cluttered with normal 18-year old girl things; clothes, makeup, shoes, boots, accessories, a...

Boarding School Blowjob

by HaskellHacker on Dec 12, 2018
First Time

Tom and Charles had been best friends since they were 9. They had met playing for the same school rugby team. Through this, they spent a lot of time together and formed a bond that had lasted. They both left primary school and joined the same secondary school, which happened to be a boarding school. There, again they were both accomplished players and so spe...

Spying on My Girlfriend

by DarkrSide on Mar 27, 2019
Exhibitionist & Voyeur

EVERY CHARACTER IS OVER 18 YEARS OLD "Which bathing suit should I pack?" my girlfriend Lori asked. I stuck my head out of the bathroom. In one hand she held a modest one piece bathing suit and in the other she had what could only be described as a bikini. I couldn't help but laugh. "I'm sure your students would love that one," I said as I pointed to the b...

It's for Research Ch. 03

by PrincessErin on Sep 16, 2017
Toys & Masturbation

Nathan unlocked his front door and was confused. The house was completely dark. He had been meeting with his editor and had been invited out for drinks afterwards. Brianna knew that he was going to be late, but she normally waited up for him. She was not the jealous type and knew that when he was out late, she would catch up on her reading or sometimes go ou...

Under The Red Roof

by SEVERUSMAX on Sep 16, 2017
Group Sex

I was barely inside the door of my room when I was attacked, and rather hungrily, by her. She had her mouth on mine, her lips pressed to my own, her tongue soon pushing past to taste me and see if I had done what she asked of me. I had, of course, wanting to see what she would do about it, and I wasn't disappointed. My pants were soon down at my ankles, her...

Winning an Unexpected Bet Ch. 03

by madmartigan37 on Nov 13, 2017
First Time

I didn't see Becca for about a week after that night at the bookstore. I also cut back on texting her. It seemed like she was falling for me and that wasn't a good idea for either of us. She was going to be going to university in the fall and meeting a bunch of new people. There was a good chance she'd meet lots of new guys there and fall for somebody new. I...

Neighbourhood Terror to Sissy Pt. 13

by Fibaro on Oct 7, 2019
Transgender & Crossdressers

Chapter 15 Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...

Like a Boss Ch. 04

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

After her latest night with the first ever NXT women's champion Sasha Banks woke up with a sore, gaping ass hole and Paige nowhere to be found. She had been pissed off ever since, especially as she was forced to wait for hours for her ass to heal enough so that she could just stumble around, and in that time she'd have plenty of chances to plot her revenge a...

The Saree Bet Ch. 01

by piyali19 on Mar 2, 2020
Transgender & Crossdressers

My name is Ishita. However, I didn't always go by this name -- I was called Ishaan before. I grew up in a middle class Indian family in the suburbs of Delhi. I was very shy and awkward growing up. And girls just scared the hell out of me. I was around 5 feet 5 inches tall and had a slim body. I also had shoulder length hair. I had grown my hair over the hol...

First Time Tied

by storm_usmc on Sep 12, 2017
BDSM

This is a story about a coworker of mine and her first experience with bondage. To begin with I'm a Marine stationed at Camp Pendleton. I'm 28 years old with brown hair, I stand 5'11" 190 pounds and am muscular. I've been told by women that I'm really good looking and am even more attractive due to the confidence I exhibit. I had just come back from my secon...