To stop using bad puns in my stories. Get it? Ok enough crap, onto the story. I've made a lot of bad internet based decisions and this was no different. The ad was posted by a "woman." Well it was in the W4M section but that means nothing today. So it was posted by a woman and it was an actual woman believe it or not. She was looking for a guy to play her in pool with the potential for adult fun afterward. I love playing pool, I always have. I kept myself in beer money during college by hustling at the student center game room. So I replied and we chatted a bit online and through texts before she invited me over one night to play on her table. She lived a few towns away in a nice condo and she had a very nice pool table in her dining room. This is something I want to someday, a pool table in the dining room. Fuck you at Thanksgiving, stand and eat your bird, we're playing 9 ball. Sorry, something shiny, I got distracted. She was gorgeous, wearing a very short skirt, a low cut top and heels. she seemed to want to flirt as she bent over in front of me to take a shot. We played a few games. I went easy on her and she was an ok player.
"Let's make a bet on the next game? How about the loser gets fucked?"
"Sure." I said with a smile. I thought to myself that I win either way. I let her break and she got in one, then another, then another. Then she missed and it was my turn. I got in one, then another, then another. I looked up and in my field of view was my sexy new friend, only now she was topless and her breasts were gorgeous. Obviously I missed my shot. She went and ran the table, but missed the 8 ball. I was bent over and lining up my next shot when I felt her press her body against mine. Something didn't seem right, and I quickly made another shot. I turned around to make a sarcastic comment about not distracting me when I saw it. It being a leather harness with a rather large dildo protruding from it.
"Remember...loser gets fucked!" She said with a wicked grin.
I've seen pegging videos online and it just looked painful. Now I really had to sink this shot and all the others and win the game. Nope, I knocked the 8 ball in too soon. I lose...fuck me.
"Good game, now bend over the table."
"Are you serious about that? I thought you were just using it to distract me? How about you let me pleasure you with my mouth instead?"
She walked over and sat on her couch with her legs spread. I knelt in front of her and waited for her to remove the harness. Instead she bent her legs at the knee and guided my head towards the toy.
"I'm not gay." I cried out as she stuffed the head in my open mouth. She had very strong athletic legs and my head was pinned towards her crotch as she gyrated and fucked my face with the dildo. After many gags and gasps she released me and I collapsed on the couch next to her in a heap.
"You are an awful cocksucker. Here, let me show you how it's done."
She quickly unsnapped my jeans and pulled my soft cock out. She buried her face in my lap and took me in deep. She gave me a world class blowjob and it felt amazing as all blowjobs should. Then she suddenly stopped.
"Now about that bet we made." She said sweetly. "I'll be nice and let you choose the position. Doggystyle on the couch or bent over the pool table?"
"I guess doggystyle." I said with a defeated tone in my voice.
I got undressed and assumed the position. She squirted lube on the toy and on my ass. She stuck a finger in to loosen me up and then tried two.
"Holy shit, you're tight. This is going to be fun. Try to relax, it'll hurt less."
I took a deep breath and started thinking about fucking her. She was able to get both fingers inside. She used more lube and put the cockhead to my puckered hole and slowly guided it in.
"Wow that fucking hurts." I moved forward and tried to get it out.
"Relax, relax. Once the head is all the way in, it won't hurt as much."