I Made a “Bad” Decision Last Night [FM]

I was meeting my boss for drinks. We work remotely for the same small company and meet occasionally for work stuff or drinks.

She’s great, but she always end up trying to set me up. It’s not them, it’s me. All of my life, I have had sex and view it as an experience. I have done some crazy shit and only a handful of times, doubted my decisions. I guess I just haven’t been wowed by any of the men that have bedded me.

Drinks led to dinner, then more drinks. We were joined at dinner by friends of ours and as it got dark outside, people started peeling off. I found myself drinking with a woman named Mel. She was a friend of my bosses and is pretty badass.

We ended up at a local dive bar and next thing I know, I am shooting pool with two men in the back. Mel is paired with Tim and I am paired with Matt. Matt was fit and lean and his skin was leathery brown from working in construction.

Every time Matt leaned over me to “coach” me on my shot, I could feel him pressing into me. If he would clean himself up, he’d be cute. I had already told him a few times that I had a pool table in my basement growing up, and showed him as well with my skilled shots. It had been a while that a man pressed his semi chub in my backside and I didn’t mind what he was doing and play along.

As the night progressed, the four of us played and watched other play pool while drinking beer. I made my way to the bathroom and when I returned, Mel had left with Tim. I decided that I was going to finish my beer and take off, but Matt had talked me into playing one more game and I agreed.

Matt started off strong and put down two after his break. I was able to keep pace and midway through we were about even. I was lining up a shot and Matt moved from his usually place by the pocket that I was shooting at to behind me. He bent over

“Want to make the game more interesting?”

I paused and turned my head “How about $20.”

I turned and sank my shot and walked to the other side of the table to line up my next and he followed.

“How about I give you $20 if you win and you give me head if I win”

I shook my head and laughed to the point where I had to stand up. I turned and faced him.

“My blowjobs are worth more than $20” and then gave him a smirking smile before spinning back to the table and lining up my shot.

I could hear him rustling as I lined my shot and then a bill was placed next to me.

“$100”

I dropped my head, exhaled, then rose up and turned to him.

“If I lose, and I am not going to lose. I am not giving you head here in this bar.”

He grinned “I know some places out back where there will be some privacy this time of night.”

I exhaled and lightly shook my head. “I bet you do.” then I paused. “You are on.”

The game went on and it stayed close to the end. Matt had two balls and I was on the 8 ball. The “gamesmanship” was at an all time low from gentle grazes to him dry humping the pocket I was shooting at. He sank one and was lining up a long shot, so I went behind the pocket and unbuttoned two buttons on my sundress and leaned over the table, giving him full view down the top of my dress. My breasts, just hanging over the pocket. Needless to say, he missed, but left me with a shitty shot on the 8 ball.

His ball was blocking me from cutting it down the rail, so I called the opposite corner.

Matt stood over the balls and grabbed his cock through his jeans. By the time I lined up the shot, I couldn’t help but notice his bulge in his hand. I refocused and took the shot. My buzz made me shoot a bit too hard. The 8 ball rolled across the table and hit the back bumper about an inch too short and missed the pocket. The cue ball rolled precariously down to my side of the table and I watch in horror as it skidded against the opposite rail and dropped in the pocket. My shoulders dropped and I exhaled knowing that I had just scratched and lost.

I looked over at Matt and his grin was priceless. He came over and grabbed my beer on the way.

With a completely straight face he handed me my quarter glass of beer “I’m gonna pay the tab. Why don’t you finish your beer and put away the cues and we can head out.”

My stomach sank and I was in disbelief. I gathered the cues and the bridge and put them on the rack and finished my beer. Matt returned with stoic and reached out for my hand.

“You ready?”

I gave him an expressionless nod and followed him out the back door of the bar where people were smoking earlier. There was no getting out of this. I live in a small town and not paying my debt on a bet would be a much bigger story than paying my bet, which would probably be seen as a tall tale told by a drunk.

He led me behind the next building to a small parking lot that met a row of small businesses. We then went down an alley towards Main Street and to our left there were stairs that led down to a tattoo parlor. I slowly walked down the stairs which were illuminated by a neon tattoo sign. By the door there was a wooden bench and Matt stopped and turned to me.

I wanted to get this over with. The competitive me was still in disbelief that I had lost. That bothered me more than the fact that I was about to have an older man stick his dick in my mouth and I was going to have to blow him and swallow his load.

All of the sudden, I snapped out of the funk and came to terms that it was time to pay up. It had almost two months since I last had sex and I thought to myself that I should just enjoy whatever was in store for me over the next few minutes.

Matt asked if I wanted to fool around first and I bit my lip and nodded. He stepped into me and lowered his head to mine. The kiss was better than I had expected and at first his hands rested on my hips before moving towards my breasts. He managed to get his hand in the top of my breast and pinched my nipple and I separated from him.

“Am I being too rough?”

I unbuttoned more buttons from the top of my dress giving him more access.

“No”

And we went back at it.

My hand grabbed at his bulge in his jeans and rubbed his growing cock. My other hand slid down and I began working on his belt buckle, then button and zipper of his jeans. Once I got his jeans opened, I slid my hands under his shirt and pushed upward, exposing his ripped abdomen. His shirt flung off and was discarded on the ground and I began kissing his neck, then chest and working myself lower.

I squatted in front of him and gave his cock one final rub before pulling his jeans down for the reveal. It sprung out and I gazed at it before taking hold of his shaft and looking upward. It had been a while since I had one this size and I wasn’t going to waste it.

Matt grinned and locked with my eyes as my tongue teased the tip glided up and down his shaft. My palms rested on his abs as I took him in my mouth for the first time.

He muttered “Ohhhh fuck yeah” as I tested how deep I could take him. I knew I could take him deeper without gagging, but wasn’t going to reveal that just yet.

I slowly bobbed and twisted my head on his cock while letting out subtle moans. My right hand slid down to and gripped his shaft and my head bobbed into it a few times before I started pumping in sync with my head bobbing.

Every time I opened my eyes and looked up, Matt gave me a “fuck yeah” or “oh my god yeah” as I worked his cock in my mouth.

I was wet and horny and dirty thoughts of taking this further filled my head. His cock was divine and I wanted him inside me.

I released his cock and he watched at my tongue run up the length and then I left it hanging in front of me.

“Sit on the bench”

Without hesitation, he did what he was told and watched me raise in front of him. I re positioned myself in front of him and leaned and gave him a passionate wet kiss. Our head separated and I placed a my hands on either side of his hips on the bench and took him back in my mouth.

He sat further back and watched as I bobbed and twisted and moaned on his cock. My pussy was at the point of exploding and I was not going to waste such a beautiful cock on just giving head.

I again separated and stood in front of him. He watched as I tugged at the tie around my waste, then pushed the straps of my sundress from my shoulders. My sundress dropped to the ground and revealed my naked body. His mouth opened slightly and his eyes opened wider as he devoured me in his mind.

I stepped into him and then climbed on top of him. I gave him a brief kiss before guiding his tip into my wet slit. He placed his hands on my hips as I worked him inside of me. Any discomfort passed as I focused on working him deep inside of me.

Once fully inside, I grinded on him and we kissed again before I grabbed his head and pushed it into my breasts. I was relishing every second that he was inside of me as he sloppily sucked and kissed my breasts.

I raised my hips and lowered my head to his ear.

“Fuck me.”

His hands gripped onto my hips and he began thrusting inside of me. The creaking of the bench got louder as his hip drove his cock in and out of me. I didn’t care if the bench broke. I was loving every inch of his cock and caught up in the moment.

He muttered “I am going to cum”.

Normally, I would jump off and let him finish in my mouth, but I was too into the moment that I told him to keep fucking me.

Moments later he gripped my hips harder and drove himself deep inside of me. I felt the twitch as he unloaded deep inside of me. I arch my back and grinded on top of him until grip eased, then I leaned into him and gave him a kiss as we remained as one sweaty ball of sex on a wooden bench.

After one more kiss, I climbed off of him and grabbed my sundress from the ground and pulled it over my head. I collected my flip flops and we made our way up the steps to the alley.

Matt offered me a ride home and I declined because I lived only a few blocks. I wanted to relish the events that just happened as I walked those few blocks back to my place.

​

**** To Be Continued ****

Source: reddit.com/r/gonewildstories/comments/x4elsy/i_made_a_bad_decision_last_night_fm