Lost Bet Blowjob Stories

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Lost Bet

by Pippa on Sep 11, 2017
Fetish

It all began as a bit of a joke really. We'd all been out clubbing in some really raunchy nightspots and were still high on both the atmosphere and the 2 Love-doves that we'd swallowed a few hours before. As the night wore on and morning was quickly rearing its bright and beautiful head, the group began to dwindle until only three of us were left. My husband...

Lost Bet

by Kinxx on Sep 13, 2017
Anal

It was almost a Saturday afternoon ritual - Jim, one of my friends from work would come over and we'd watch the football game (or hockey if it was winter), drink some beer (ok, a lot of beer) and enjoy ourselves. Usually our wives would get together and either go shopping, out to a movie or basically be anywhere but there with us. It usually worked out ok...

A Lost Bet Ch. 04

by amarasfantasy on Sep 12, 2017
Transsexuals & Crossdressers

As I slept that night, I dreamt vivid dreams...sexual dreams. The next morning, I was able to remember one of the dreams that I had but I didn't tell Frank or Tom. I kept it to myself because I wanted to understand what it meant. I'd dreamt that I was walking down the street when I got close to the entrance of a park. It was me in my male clothes. As I got c...

A Lost Bet Ch. 02

by amarasfantasy on Sep 12, 2017
Transsexuals & Crossdressers

It was a fitful night. While the chair had been designed to provide at least a little comfort, having my arms bound behind me all night got to be uncomfortable. Plus, I was forced to remain in the same position because of being bound to the chair. And it didn't help that every so often, I had a machine pumping in and out of my ass. I slept intermittently, bu...

A Lost Bet Turns into a Fun Night

by swingingrichards1 on Sep 28, 2020
Exhibitionist & Voyeur

"You lost the bet." Lindsey said. "I know. I still can't believe they blew a three-run lead in the ninth inning though. I'll get the next round of beers." I replied. "No- let's make it more interesting. I have a girls' night this weekend for Emily's birthday and you know she recently broke up with her boyfriend. What if you were a stripper for us?" Lindse...

Slutty Sue Pays Off Her Lost Bet

by raidernation25 on Sep 13, 2017
Group Sex

I don't know why I bet on things I know nothing about. I hate football but a few years ago I lost a bet with my husband on the Super Bowl. I thought that Denver would destroy Seattle while my husband, a Raiders fan didn't really care one way or another. "As a Raiders fan I hate both teams equally," my hubby Ed explained. Well stupid me picked Denver and E...

Bet Your Bottom

by RejectReality on Sep 12, 2017
Anal

"I can't believe you're making me do this," Natalie said as she stood on the hotel balcony at three a.m. with the wind blowing through her strawberry-blonde hair. Her eyes scanned the parking lot, and though she didn't see any signs of life, someone down in the darkness would be a lot harder to see than she would be on the balcony — dimly lit as it was...

Daring Exposition

by bluueboy on Sep 12, 2017
Exhibitionist & Voyeur

A few years ago I lost a bet to my live-in boyfriend. Which meant he would own me for an entire week. Well this particular week included my birthday as well. First, let me tell you about me because that seems to be how this usually seems to go. I have very dark brown hair and brown eyes. I am 5'2" and muscular from years of gymnastics. I am extremely flexi...

Bar Bet Weekend

by LiseKLord on Feb 7, 2018
BDSM

Joly and Rina had been friends since elementary school, through high school as well. They had been college roommates and now, five years after graduation, thanks to good jobs, they still chose to share a very nice condo in the heart of downtown. They knew everything about each other, and despite the occasional annoyances any living together relationship migh...

Booty Shorts

by Jamie753 on Jun 26, 2019
Exhibitionist & Voyeur

Amy lay in bed thinking about how her day had gone. First noteworthy thing that happened that morning was her roommate Cassie telling her it was time to fulfill her obligation for the lost bet Amy had made over the weekend. Along with her declaration Cassie had handed her a pair of shorts and told Amy that she had to wear them all day. Looking over the ga...