[MF] Fun with the bartender…

A bit of an introduction first. I am a 27/M, 5’11”, 180 lbs. I have short, dark hair, and an athletic physique. Years of playing baseball got me into the habit of working out regularly, and I have done my best to keep up with that. I am not in the shape I was in college, but working on getting back there. My line of work requires me to travel for about two weeks every month, on average. Normally I am accompanied by anywhere from 2-5 co-workers per trip, and together we handle marketing and public relations for various special events. It is the perfect job for a single man like myself. I get to be home for a while, but also get to go to new places, meet new people, and rack up frequent flyer miles and hotel points.

This past October was a particularly busy month. In a three-week span, I was in six different states. I was sick of airplanes and hotels by the end of the month, which anyone in sales or a similar travel-heavy field can relate to. But I get paid nicely, so I can’t complain.

The last trip of the month was the easiest one from a work perspective. I was scheduled to be there for only one day and night to deliver some marketing materials from corporate and conduct two hour-long meetings. Afterwards, two managers, Shawn and Lowell, offered to take me and my team to Happy Hour at a hole-in-the-wall bar down the street. We’ll call it A’s. We got there about 4:30pm, and I realized that this was the textbook definition of a hole-in-the-wall: tiny, cash-only, no food, an old jukebox in the corner, and a small karaoke stage in the very back. There were 7 of us, 5 men and 2 women. We were the only people in the bar at the time, so the drinks were coming fast. The beer was ice cold, and before long, Shawn started buying bourbon shots for the table. We were getting tipsy and loud. The regulars started to file in as they got off of work, but we hardly noticed.

When she wasn’t serving the other patrons, the bartender, Jessica, was spending her time sitting with us at our table and wasted no time joining in our conversations and jokes. A couple of hours in, some of the group decided to call an Uber and go back to the hotel, leaving me, Shawn, Lowell, my co-worker Christina, and Jessica.

Jessica was 25, and she was exactly my type. She was about 5’5” and thin, not skinny. She was in shape, but had enough curves to drive a man wild. Her breasts were perky C-cups (during our drunken conversations we got her to share that information with us), and her ass left the whole table staring at her every time she walked away. I will admit that I am an ass man, so I am biased, but it was incredible. There was plenty there that I was dying to grab onto, but it wasn’t fat. Even the girls at the table commented on it. She had brown hair pulled into a pony tail, and beautiful green eyes. It was clear that bartending was a perfect job for her, especially at a small bar like this. Between her looks and her flirtatious demeanor, I can’t imagine what kinds of tips she gets from the regulars.

Somewhere around 7 or 7:30, the beers and the bourbon shots were starting to hit all of us hard. Lowell was married and getting a stream of texts telling him to come home, so he left abruptly. Shawn and Christina had moved next to each other and were in their own little drunk world, flirting, whispering, and kissing. I knew where that was headed (Shawn was a notorious ladies’ man and he had set his sights on Christina from the beginning of the evening), so I decided to move to the bar and focus on Jessica. I had liquid courage, and now had her to myself, with the exception of an older couple at the end of the bar. I knew I wanted Jessica, but also knew it was going to be difficult. She was the only person working, so even if things progressed between us, it wasn’t like she could just leave. Nevertheless, we continued to talk, flirt, and drink (she even snuck a couple of shots for herself).

I was getting to the point where I needed to eat or I was going to either get sick or pass out early. There was a sports bar a couple of blocks south. I wanted to get something to eat and watch an NBA game that was coming on at 8. With nothing to lose, I asked Jessica if she wanted to meet me there at some point. She declined regretfully, saying she had to work until 11, and then was meeting up with friends. I tried my hardest not to seem too disappointed as she continued to apologize and we eventually said our goodbyes. I told Shawn and Christina where I was going and started walking towards my next destination.

I chugged two large glasses of water and got some much-needed food in my system as I settled down at the sports bar. There were a few other guys there, presumably businessmen like myself, but it was pretty quiet, even for a weeknight. The game was a blowout, and not entertaining at all, so I decided to call it a night at about 10pm. As I was preparing to pay, someone sat down right next to me at the bar, which I thought was strange considering how much room there was elsewhere. I glanced over and saw a familiar pair of jeans. I made my way up and realized it was Jessica, staring straight ahead, trying not to laugh. I was at a loss for words, and she finally busted out laughing and gave me a hug. She explained that her boss, the owner of A’s, came in and decided to start working on inventory, and told Jessica that he would finish out the night so that she could leave early. After making up a lame excuse to her friends, she decided to join me. I could not believe this stroke of luck.

I noticed that she had changed from her black work t-shirt into a stunning, purple, v-neck blouse. The material and design of the shirt accentuated her chest perfectly, and I couldn’t help but stare, which she noticed and encouraged.

There were a few minutes of small talk, and then she ordered two bourbon shots and made a toast to “tonight.” We each took our shot, after which she leaned over and kissed me. I was caught by surprise, but I wasted no time kissing her back. She aggressively grabbed me by the back of my head and pulled me deeper into the kiss. At that point, I knew what she meant by “tonight,” and that things were just getting started. I pulled away from her and we made eye contact. There was no more laughter and kidding around. She wanted it as bad as I did. She quickly accepted an invitation back to my hotel. I was not “prepared” for an encounter like this, so our Uber driver was forced to make a quick stop at the drug store so I could buy condoms.

We reached the hotel and rushed to my room. Once the door closed behind us, we were all over each other. I grabbed her, pressed her against the door, and explored her mouth with my tongue. For the first time, I was able to do what I had been wanting to do all night, which was to grab her ass and squeeze with both hands. Jessica moaned as I pulled her body closer to mine and she pressed against the quickly-growing bulge in my pants. Without leaving our kiss, she unbuckled my belt and pulled my pants to the floor. Without hesitation, her hand grasped my hard cock. She began to stroke it gently, occasionally letting go to fondle my balls. After a couple of minutes of this, she led me by the hand to the king-sized bed.

She instructed me to lay on my back on the bed. I watched intently as she climbed over top of me and began to unbutton my light green dress shirt. Without breaking eye contact, Jessica grabbed the bottom of her shirt and pulled it up over her head, revealing a lacy red bra. It took everything I had not to jump up and rip her bra off right then, but I knew my chance would come. My patience was tested even more as Jessica stood up and turned so that her back was to me. During our conversations earlier in the evening I mentioned that I was an ass man, and she asked what I thought of hers. She clearly remembered my reaction and that conversation, because she began teasing me. She pulled her jeans down just enough to see the top of her panties and then pulled them back up, shaking her ass the whole time. This continued for a bit, until she slowly removed her jeans entirely, revealing that perfect ass that I had been waiting for. She was wearing a red thong to match her bra, and bent over to step out of her jeans, giving me the absolute perfect view. I swear I almost came right then, but somehow I controlled myself with some deep breaths. Jessica turned around to face me, standing only in her bra and panties, and a sly smile across her face.

With me still on my back, but watching her every move, she once again crawled over top of me and kissed me passionately. Her lips moved down my neck, up and down each of my arms, down my chest, and back to my cock, which was almost painfully hard at this point. She licked the tip, swirling her tongue around to taste the pre-cum. My breathing was growing rapidly and I knew I did not have much longer before I busted. She apparently knew too, as she crawled back up and whispered in my ear, “come in my mouth.” I don’t remember if I said anything or just grumbled random sounds. She licked up the shaft and then began taking me into her mouth little by little. I am about 6” long, and have average girth. I won’t be starring in any porn movies, but have never received any complaints. This was clearly not Jessica’s first time, as she deep-throated me and swirled her tongue around as to not miss a spot. She started to gag a bit, then pulled back and caught her breath.

Jessica then did something that drove me crazy. She reached back and undid her pony tail, letting her long brown hair fall down around her face and onto my lower torso. The subtle tickle of her hair against my skin, combined with the feeling of her warm mouth around my cock, sent shockwaves throughout my body. I shivered, and reached down to grab her right hand with my left. Our fingers interlocked and we squeezed each other’s hand as her pace began to pick up. She had gone from lightly licking and teasing my cock to full-on sucking. Her head bobbed up and down as she tucked her hair behind her ear, allowing me to see everything that was going on. Her hand that was not holding onto mine found its way to my balls and began to work them as the sucking intensified. My increasing moaning hinted to her that it was not going to be long. She let go of my hand and switched positions so that she was now leaning over me from the side, so I could reach up with my left hand and grab onto her ass while she sucked. Not more than a few seconds later I felt that familiar feeling and couldn’t control myself any longer. As her head continued to move, I took a deep breath and unloaded shot after shot of hot cum into her mouth. She never hesitated, and made sure to get every last drop down her throat.

Then it was Jessica’s turn. As I came down from my high, I grabbed her by the arm and pulled her to me. She screamed playfully and giggled as I began kissing her neck. I reached behind her and undid her bra. Her tits bounced slightly as they were freed from her bra and I took the time to admire them. As I mentioned before, they were incredibly perky. She had large nipples, and I immediately lowered my head and took one of them into my mouth. Her fingers ran through my hair, tugging on it as I flicked her nipple with my tongue. As I nibbled on them with gradual force, she tugged harder on my hair, enjoying every second. I continued this for a while, then leaned back and took both breasts in my hands and squeezed them gently. She took this opportunity to reach down and begin lowering her panties. There was no more playful teasing; she was ready. I ripped her panties off of her and threw them blindly behind me. I sat mesmerized by her shaved pussy.

I told her to get comfortable as I sunk my head between her legs and began to work on her. I playfully licked and sucked her thighs, made my way to her taint, and then to her slit. I separated her lips with my tongue, which then found its way inside her. Jessica closed her eyes and began playing with her nipples. I took this as a sign that I was doing things right, so continued confidently. As she grew wetter, I inserted one finger, then two, and began slowly exploring inside of her. While fingering her, my mouth turned its attention to her clit. I started out slowly circling it with my tongue and blowing on it gently. Jessica squeezed her thighs around my head and moaned louder. The moaning turned into mild whimpering as I continued to work her clit. I alternated between licking, sucking, and lightly nibbling, while continuing to finger-fuck her. She reached up and grabbed the headboard behind her and began screaming in between breaths. She screamed out that she was cumming and her body convulsed. One of her hands grabbed onto my hair once again as she steadied herself. She then grabbed the back of my head, just as she had at the sports bar when we kissed, and pulled my head deeper into her crotch. I was loving it and did not want to stop. I brought her to one more orgasm, after which she needed to take a break.

I walked to get two bottles of water from the mini fridge, and as I circled back to the bed, Jessica noticed that I was almost completely hard again. After taking a few sips of water, we began to make out, tasting each other’s juices in our mouths. After a few minutes she asked if I was ready. I readily agreed and asked her the same question. She responded by flipping me onto my back once again and climbing on top of me. I reached over and grabbed the box of condoms and put one on while Jessica played with her nipples. Once I was done she grabbed the base of my cock and guided it into her tight pussy. She lowered herself all the way down to the base and I was balls deep inside of her. Her tits bounced as she began to ride me. She bent over and rested her hands on my chest for support, letting her hair fall in front of her face. As her speed increased, so did the volume of her moaning. She gazed into my eyes and we did not break eye contact for the next few minutes.

I pulled out quickly and turned over. I flipped Jessica over onto her stomach and pulled up on her waist, inviting her to stick her ass up in the air. She took the hint and raised up onto all fours. I took hold of her ass with one hand, and guided my cock into her with the other. I took her waist in my hands as we synced our motions and engaged in the hardest fucking of the night. Jessica turned around and looked at me with a dirty smile as I rammed into her. Our bodies were slamming into each other so hard that I had to ask and make sure I wasn’t hurting her. She just moaned and said “don’t stop.” The motion of her ass as I fucked her was hypnotizing. She reached her hand up and played with her clit for a short time, before sinking her head into a pillow and screaming into it. She stopped her movement for a split second as she came.

I slowed my pace while she recovered. I grabbed her chest and pulled her up so that we were both kneeling in the upright position, with my cock still inside of her. I grabbed onto her tits with both hands and built back up to a faster speed. I felt myself tensing up again, so I flipped Jessica onto her back and began to fuck her missionary style. Our lips met again as we fell into a deep kiss, her wet pussy taking in the entire length of my cock. I fucked her hard in that position for another couple of minutes, and my turn had arrived. I grabbed both of her hands with mine and I experienced an orgasm more powerful than I ever imagined as I came inside of her. My arms and legs were literally shaking as I pulled out and fell onto the bed next to Jessica. She rolled over onto her side and I embraced her, kissing her forehead as her eyes closed and she smiled. Her hands rested on my chest as I stared at the ceiling, recovering from one of the most passionate nights of my life.

Before I knew it, she was asleep. I turned her over and covered her up with the blankets while I went and cleaned myself up. I lay back down and fell asleep next to her. The next morning we drank coffee together and talked for another few hours. She eventually had to go but told me she was off work that night. I immediately re-booked my flight for the following day, and we spent another night together. Depending on how this story is received, maybe I’ll tell that story later…

Source: reddit.com/r/gonewildstories/comments/7dhedx/mf_fun_with_the_bartender