This is a story. It is not real. Any similarities of characters to someone in real life is strictly coincidental.
Warning: If you are offended by adult material, please do no read.
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Brian was a singer. And his singing was as bad as his decision making. Most of the time this was annoying, but one night it really worked in my favor.
It was about ten at night when Brian and his girlfriend Heather came over. Brian was slightly buzzed, and Heather explained she wanted to stop by instead of having Brian drive all the way home. Brian came in and started talking to me. When Heather bent down to set down her purse, I got a good look at her cleavage. Heather wasn't the thinnest brunette I knew, but her tits were superb and she had a pretty face. She was probably insecure about her weight which was why she let Brian treat her like shit. I stayed out of it.
"Hey you're playing minesweeper?" Brian asked stupidly. He had a tendency to get excited about the strangest things.
"Yeah," I said. "I was bored."
"That game is so impossible. I bet you can't beat it."
"PA-LEEZ, I am the Minesweeper master," I joked.
So I sat at my desk and started the game back up.
"Holy shit, how do you know where they are?" He was so stupid.
"I don't know, I just do somehow," I lied. It was hilarious to let him come to conclusions.
Just then I made a mistake. It was set to medium. Sometimes that happened.
"Oh! I knew you couldn't do it!"
"Want to bet?" I asked him
"You're on. $5 bucks says you can't beat it next time either."
"Pff, 5 bucks? Can't you think of anything more interesting?"
"Umm, ok. If you win, Heather will show you her tits."
I eyed Heather, surprised, and looked back up at him.
"Brian, what the fuck?" Heather exclaimed, looking away from the tv she had flipped on earlier.
"It's no big deal. He won't win. Besides, its just your boobs, don't be so uptight, I thought I was dating someone cool." Heather looked away and crossed her arms in discomfort.
Holy shit, would she do it? I thought to myself. It looked like she might.
"Ok, you're on. $5 bucks to you if I lose, and Heather's tits if I win." Brian nodded. Idiot.
I started and was more careful this time. I won easily.
"Oh my gosh!" Brian smacked his hand to his head and looked down at the floor. I glanced over at Heather. She was sitting on my couch, legs and arms crossed, refusing to look over at us.
Brian looked over at Heather, and shifted a little bit.
"Double or nothing," he said.
"What do you mean?"
"I mean play it on hard. If you lose, you owe me 50 bucks, if you win Heather gives you a blowjob."
"What the hell Brian?! I will not give him a blowjob! I don't agree to this!"
I listened to them argue in my living room. Brian was slightly buzzed adding to his already above average stupidity. But it looked like Heather didn't want him to think she wasn't cool enough for his "rock and roll lifestyle". I couldn't believe she was going along with this.
When they were finished Brian kissed Heather on the forehead. "I knew I had a cool girlfriend." I could tell Heather was making a conscious effort to appear comfortable with this. I trembled at the thought of those lips on my cock.
The trouble was I wasn't sure I could do it.
"Hard is almost impossible Brian. How about I get three tries. But if I lose all three times, I pay you $100. But if I do win, Heather does the job topless, and I get all creative control of the act."
Brian hardly heard the last part with $100 on his mind. I noticed Heather stiffen on the couch though. She wasn't the only thing that did.
"$100? Alright, you're on."
I tried to be as careful as possible. To put it lightly, I had never cared about a game of minesweeper so much and couldn't believe the last ten minutes. I lost the first game. I came close, but it turned into a 50/50 chance and I guessed wrong. Damn mines! The second game I lost before I could get a foothold. I swore.
"I'm gonna pay off my bar tab," Brian said excitedly.
The third game I got a lucky start. It seemed like half the field was cleared by my first click. I was able to seperate out most of the mines by elimination, and only a few came down to a guess. I got lucky, and the game was mine. I won.
"Oh crap," Brian said under his breathe. He had counted on me losing. I let out a breathe I had been holding.
"Damn, could have used that $100. I'm gonna use the bathroom and take a walk. How long you gonna be?"
"I'm gonna take my time if you don't mind. You wanted to sober up before you left anyway, right?"
"Sure, whatever. I'll walk to the store. She can call me when she's ready."
He walked off to my bathroom. Heather hadn't moved.
After a minute of her not moving, I got up and walked into the living room where she was still sitting on the couch. My erection was making a tent in my pants.
She looked at me and sighed. "Let's get this over with." She sat up straighter and leaned forward a little, as if I would approach her for her chore.
"Hey, take off your shirt first."
She looked at the floor and delayed for a moment. Then she lifted up her shirt, revealing her white bra. I sat on the couch next to her, and pulled out my erection, rubbing some pre-cum on her stomach. She started to lower her head down towards my crotch.
"No, get on your knees in front of me."
She glared up at me. "Fine."
She did so. She looked good on her knees.
"Now the bra." I could tell she didn't like being ordered like this. It made it even hotter.
She undid her bra and let her breasts pop free. They were shapely and luscious. I couldn't help but gasp.
"Happy now?" she asked, topless on her knees in front of me. I could see a little tear forming, so I got on with it.
"Nice and slow." I told her.
She went down, and I felt her warm mouth slip around my cock. I moaned loudly.
I heard Brian open my bathroom door, and he walked by to the front door.
"Good girl," I said, purely for Brian's benefit. Out of the corner of my eye, I saw him stop in the hallway, and peek around at us. I pulled out my cock and a string of pre-cum pulled out with it from Heathers tongue. Then instead of putting it back in her mouth, I rubbed in onto her face. She tried to pull away, but I grabbed her hair and she stopped. I rubbed it all along the side of her face so Brian could see.
"Fucking asshole," she muttered.
