Lost Bet Girlfriend Stories

201,764 results
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Infinite Scroll

Ashley's Boyfriend Makes a Bet

by Rembacher on Sep 14, 2017
Loving Wives

I was back in Niagara. I'd spent two years here attending Niagara College studying international business. It had been a few years, but I was back for the week as part of a convention for my internship employment. The internship is the key part of my Bachelor of Commerce in Honours Business Administration minoring in Modern Languages- Spanish. (Yup, that's a...

Our Third Holiday

by holiday_show on Aug 19, 2017
Exhibitionist & Voyeur

We had been together for a few years now and this was our third holiday together. The first one in Lanzarote she went topless on our balcony, I even managed to take a couple of pictures. The second holiday together in Greece she went topless on a quiet beach away from the apartments, there were a few people around but mainly older people. This time I wanted...

Stephanie and the Poker Game

by floridaguy2001 on Sep 19, 2017
Loving Wives

Stephanie, my girlfriend has heard for a while now about my buddies and the poker games I hold, she has always wanted to meet them and I told her the next game she was invited but she had to behave because Stephanie has quite a wild streak, she told me she would and sounded almost giddy looking forward to the game. I told her okay baby we will have the game...

Busted, But Still A Head

by brewdude2003 on Sep 16, 2017
Erotic Couplings

King, Jack. Dealer has a six showing. Gravy. I'm back in the game. I sweep my hand over my cards. The dealer flips her hole card, and there lies a queen. She has to hit, and she's going to bust. Money in the bank. Dealer takes her hit and pulls a five. "Twenty-one" the dealer announces, as if to rub salt into the wound. I was totally cleaned out, but felt d...

Two Lesbians Gangbang

by SlutProblems on May 7, 2019
Group Sex

Maybe I should have told Lily that I was a lesbian right away. She probably would have understood my sordid past a lot better if she knew. Things would have progressed between us a lot more quickly with our relationship as well. If I had only known that she would become the love of my life I would have done things a lot differently. The truth is, being a les...

Winning an Unexpected Bet

by madmartigan37 on Sep 26, 2017
First Time

I was twenty five when this story happened, but still working on an undergraduate degree at university. I'd made some bad decisions right after high school, flunked out, taken a few years off to get my shit together and finally gone back. I was living with my girlfriend and she was working full time to support me, but I had a part time job at a bookstore in...

The Finest Competition

by SteveRay on Sep 17, 2017
Group Sex

My Friday night out with the boys had come to basically nothing so after a couple of beers at the pub I decided to call on my girlfriend Nicky who had stayed in that night to study for some upcoming uni exams. When I arrived I was only mildly surprised to find out that the studying had been canned and she was relaxing on the couch watching a movie with one o...

The Girl with the Freckles Pt. 05

by FreckleLover on Sep 19, 2017
Erotic Couplings

"Can't you just try doing a slap bass? We need that percussive snap, more funk feel," I pleaded with Danny. "What the fuck do you want from me? I told you a million times," he growled, half angry, half frustrated. "I can't slap! YOU fucking play bass if you think you can do it!" "Shit," I muttered under my breath. "Alright, alright. I'll try'n work out an...

Anything for Lindsay Ch. 05

by allaboutcontrol on Sep 26, 2017
Fetish

"Oh god, oh my....," Jason said, in pure pleasure, trying with every ounce of his body to hold back from cuming. Lindsay was sitting next to Jason, slowly stroking his penis. Jason was completely naked laying on Lindsay's bed. Lindsay was fully clothed in a tank top and a pair of jeans. "Its only been 50 seconds Jay, hold on, you still got a little over tw...

Party Desire Ch. 03-04

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

Chapter 3 - A Party Surprise Downstairs Suzie and the other little girls were all running round the house excitedly playing 'pin the tail on the donkey'. Mrs Baxter calls Suzie over. 'Suzie I've a very special surprise for you. This is Molly. She's come to play with you.' I fiddle awkwardly with my ruffles and Suzie looks at me strangely some recognitio...