I [F] lost a bet to a bartender [M]

This might be a little long with some background and buildup because my favorite stories to read on this sub are the ones that are more detailed and truly paint a picture of what happened! If you’re interested in getting right to the sexy parts, scroll to the ******s.

I graduated from college a few years ago, and my best friend, Angela, and I decided we needed a weekend to hit up some of our old favorite spots back on campus. (For reference, my name is Elizabeth, but I usually go by Ellie or El) We booked an airbnb near campus and pregamed a little as we got ready to head out. I’m pretty average; I’m a 5’5 brunette with a C cup and an ass that I’ve worked for in the gym. I’m not bad looking, but I’m not a knockout. My bestie is gorgeous (taller girl with a great rack + dirty blonde hair) and loves primping, so she relished the opportunity to get me dolled up for a night out.

She gave my hair those pretty waves that look effortless and are kind of messy but also take way too long to actually do, and she gave me some dramatic winged eyeliner. I put on a matching lace bralette/thong set, my favorite leather leggings (the spanx ones!! I swear to God they’re worth every penny) and a white v-neck tee with a denim jacket.

I was in kind of a weird headspace where I was feeling nostalgic but also kind of invincible… like, I had missed all of the places we were planning to hit up, but I was coming back to them with more experience and a few years of ~real life~ under my belt. I also felt especially hot, and I was pretty horny… it had been a few weeks since I’d seen my fwb, and my vibrator had been seeing a lot of extra action, but it just wasn’t cutting it.

After getting ready and throwing back a few shots, we set out, feeling like the night was truly ours. The first stop was a bar that’s known for it’s wicked strong vodka mixers. Of course, we wanted to start here so we could carry our buzz with us for the rest of the night. We sat down by the bar and ordered our drinks. It was around 8PM, and our NBA team was playing, so we were watching them win (what up, Bucks!!) while talking with the girl behind the bar. Things were slower since it wasn’t too late yet, so she spent a decent amount of time by us. We were getting along with her really well, and when we were nearly finished with our second drinks, she told us that her shift was ending. We were getting ready to pay our tabs and leave for our next bar. Then her replacement came in.

This guy was taller, probably around 6’1 or 6’2, with a half sleeve tattoo poking out of his tshirt and a well-kept beard. He was the ideal amount of muscular, like he took care of himself but wasn’t in the gym for hours upon hours every day. He was also so confident and charismatic that I couldn’t help but watch him as he made his way through his start of shift motions behind the bar. I had my card sitting in front of me to close out our tab, since I was buying the rounds there. He eventually made his way over to us. Without saying a word or even interdicting himself, he picked up my card and set it down just out of my reach behind the bar before continuing on to pick up an empty bottle sitting next to us.

“Wait,” I said, “uhhh, aren’t you going to run my card? We were closing our tab.”

He turned around to face us with a half smile. Damn, he was really hot. Or I was just feeling somehow hornier? Or both?

“I’m really sorry, but you can’t close out your tab yet. I’m going to need you to stay for a little while and keep me company.”

Ang and I shared a “why not? Might as well stay” look with each other and took off our coats, settling back in for at least another drink with a side of some eye candy.

“We’re going to need more drinks then!” Angie called down to him.

He came back and was pouring them for us when a fairly trashed guy came up to the bar and started trying to challenge him to a chugging contest. Our bartender was able to distract him with a free “mystery shot”, and he was soon on his way.

“Sorry about that,” he said with an eyeroll as he finally delivered our drinks. “Sometimes I chug beers when I’m behind the bar, but the owner is here, so I couldn’t do it right now.”

Angie got a huge smile on her face. “Ellie here is actually really good at chugging beer! We were an unstoppable flip cup duo!”

“Really? Well, when I’m able to have some fun, why don’t we chug a beer together?”

At this point I was definitely tipsy, and there was something about him that totally had me hooked. Also, I AM pretty good at chugging beer, so I knew I wouldn’t embarrass myself even if I lost.

“Oh, you’re so on.”

We continued sipping on our drinks while our new bartender, whose name was Jake, continued turning me on. He mixed drinks with ease (the way these hands moved… oof), struck up conversations with literally everyone who came up, and paid us the perfect amount of extra attention. When a trio of guys came up to talk to us, he started stopping by even more to make sure everything was okay.

Angie was kind of hitting it off with one of the three, so they were engaged in a side conversation while I was left to talk with the other two. They were honestly really boring, and their flirting tactic was grilling me on NBA facts. The game we had been watching had ended, and it was into post-game coverage at that point. I was getting a little annoyed with defending my sports knowledge to them when Jake showed up in front of me with two empty glasses.

“Alright, I’m off my leash. What’s it going to be?”

I was delighted for a reason to ignore the other guys in favor of the one I had been lusting after for a while now. “Let’s just do coors light?”
He came back with two full pint glasses and started spelling out his beer chugging logistics: “Alright, so we clink, tap on the bar, and then chug.”

“Okay, cool, but what does the winner get??”

I’ll be real here… even though I know my chugging skills, I also know that a guy who works at a bar is always going to beat me. I was just hoping he’d ask for my number or a kiss or something like that if he won.

“How about the loser decides they can give the winner whatever they want to give them?”

It was like he read my mind, so I obviously agreed to those terms.

We went through the clinking and tapping followed by the chugging. I did a decent job, but he ultimately beat me. (Shocking)

“You decide what my prize is, and I’ll be right back.”

At this point, the bar had gotten a lot busier. It was a popular destination, and we hadn’t even wanted to be here this late because we knew how packed it could get. Two more bartenders had come on shift, and all three of them were busting their asses. Meanwhile, the two guys who’d been talking with me were trying to challenge me to another chug off. I excused myself to run to the bathroom (literally run… I was SO not into either them)

On my way, I noticed Jake, who had been heading to some kind of downstairs doorway. Probably grabbing booze to restock the bar.

“Oh, hey!” I said, bumping my shoulder against his. At this point, I had decided his prize would be my number because I couldn’t envision trying to get a make out to happen with as busy as the bar was.

He turned to me and gave me that panty soaking smile with his matching eye smolder. “Oh, hey you. Have you picked my prize yet?” We were in a smallish hallway, and he leaned up against the wall, his big frame filling the space.

********

Was it the alcohol? Was it my horniness? Was it just him? I have no idea. Whatever it was, I decided to be a little bold. I pulled open the door next to the basement one he had open, and I was relieved to find a decent sized, relatively empty closet. “Your prize is in here…” I said, walking inside.

He followed me in and locked the door behind us. It was pretty dark with the door closed, but I found him easily and wrapped my arms around his neck. His lips met mine in a heated kiss, and I leaned further into him. As I was biting and sucking on his lower lip, he moved his hands to my ass and started sliding them under my leggings. I couldn’t help but moan into his mouth.

“I’ve wanted to do this to you since I walked in and saw you sitting at the bar,” he whispered into my ear before moving his mouth to my neck. My weak spot.

I pushed myself closer against him and could feel him bulging through his jeans against my stomach. Fuck. I needed this sexy man in the worst way.

While he was still kissing my neck and running his teeth over the sensitive skin there, I slid a hand under his waistband to grasp his hard cock. I started stroking it as best I could with his jeans still on, and then it was his turn to moan.

That was all the encouragement I needed to drop to my knees in front of him. It took me a few seconds to free him from his clothes, and then I could feel the heat of him in front of my face. I licked slowly up his shaft to make things nice and wet before taking just the head into my mouth. Using both hands, I stroked up and down his length while running my tongue over his tip. He backed up to lean on the wall, and he guided me to follow by pulling my head down further on his cock. I deep throated him several times, drool messily running down my chin and on to his balls. His moans were getting louder as he started bucking his hips against me, fucking my throat.

In that moment, I wanted nothing more than to swallow his cum. I picked up the pace, alternating between deep throating him and sucking on the tip while working his shaft and balls with my hands. At one point, he found the light switch and flipped it on. The bulb glowed over us, and I looked up to meet his eyes as I took him deep into my throat again. The vision of him over me plus his delicious cock in my mouth was turning me on like crazy. I could feel my thong sliding around wetly as I moved back and forth.

“I’m… I’m going to…”

I tried to let out an encouraging “mmhmm” as I kept up my pace, working his cock in my mouth and throat. He understood somehow what I wanted, and he gave me his load. I swallowed it greedily before he pulled me back up and started kissing me again.

His hand found its way into my leggings, this time down the front, while he reached into my shirt with his other hand. We switched spots so I was leaning against the wall as he rubbed against my throbbing clit. “You get this wet giving head? You’re incredible…”

He could have done anything he wanted with me at that point.

What he decided to do was slide two of his long fingers inside of me while rubbing circles around my clit. With his other hand, he worked my shirt and bralette down so he could lean over and suck on my already painfully hard nipple. I could feel his hard cock pushing against my hip, and I cursed myself for not having a condom on me.

He knew what he was doing with his fingers, though. I had been entranced by his hands as he served drinks earlier, but what he was doing with them in that moment was on a different level. I had my fist next to my mouth so I could bite down on it instead of screaming out like I wanted to. I was grinding against his hand and pulling his head against my chest, and I knew I was close to finishing. The pace of his fingers inside me picked up, but he started making his strokes on my clit slower and longer. The effect of that simple switch set me over the edge, and I threw my head back as a rolling orgasm came over me. My knees got a little weak, and I was so grateful for the wall behind me.

When I came back down, he pulled his hand from between my legs and brought his fingers up to his mouth to lick them clean. In that moment, with the single lightbulb behind him and those fantastic fingers soaked in my wetness, he was the sexiest guy I’ve ever seen. He gave me another one of his smiles and leaned forward to kiss me again, reaching his hand behind me to grab my ass.

Eventually we parted and readjusted our clothes. He ran his fingers by the corners of my eyes to wipe off the mascara that had flaked off and helped straighten out my hair.

We both returned to the bar. I took my seat next to Ang, who had dismissed the other guys in my absence. She gave my flushed face one look and burst out laughing. Eventually, Jake came back over to us. “So…” he started, leaning over to me, “want to have a another beer chugging contest?”

I did end up giving him my number, and we’ve texted each other off and on in addition to sending some sexy snapchats. We’ll probably meet up next time I’m in town. I will DEFINITELY make sure we have condoms available.

Source: reddit.com/r/gonewildstories/comments/fdsp7l/i_f_lost_a_bet_to_a_bartender_m