Lost bar bets

I moved to Chicago during the pandemic. So when the bars started to open back up I was dying to be social again. I had visited a few bars around town and eventually found that The Jackhammer was my favorite place to hang out.  The guys were friendly and hunky. The drinks were strong and I had hooked up with a hot guy the first night I hung out there. On the busy nights  they would open a downstairs bar that was a great place to flirt. 

I work as a waiter so I have strange nights off.  Last week I had stopped in for a drink on a Monday night. The place was really dead so I finished my drink and was headed home around 6pm. On my way out I realized I had never checked out the bar next door called Touche. I didn’t really have any plans so I thought, what the heck - I‘ll have one more drink and check things out. There were a few dudes sitting at the bar and so I picked a barstool nearby, sat down and ordered a drink from the hunky shirtless bartender. They were talking about football and teasing each other about this team and that team. All of which meant nothing to me because I know absolutely NOTHING about sports or football. I try to spend most of my free time in the gym when I’m not working - so I rarely watch tv at all. One of the guys tried to involve me in the conversation and I had to confess that I had no idea what they were talking about. Folks in Chicago are really friendly and they of course bought a round of shots and before I knew it I was part of the small group. We must have talked for a few hours, because before I knew it another bartender showed up for the next shift. 

As they were changing shifts I closed out my tab with all the other guys and the bartender came around the bar and joined us in one last round of drinks that he bought for us. He had been flirting with me pretty hard all night and now that we were on the same side of the bar it was even more intense. He was sitting next to me and had let his hand wander over to my knee and then eventually it had made it’s way up my thigh until he was rubbing my now hard dick through the front my shorts. I got up and excused myself to go to the bathroom. Too many beers and shots. It took a while to start pissing because of my hardon. So I found myself just standing there with my hard dick and staring at the wall. By the time I finished up and got back out to the bar it had been a while…all the guys were laughing and joking about something and had ordered a couple pitchers of beer and another round of shots. The daytime bartender said they were going to open the back bar and watch the football game. He said it was not normally open during the week, but there was a special football game on. He asked if I would like to hang out with them and watch the game as well, so I could learn more about the game. 

To be honest, I could not care less about the game. But my hope was that I would end up hpoking up with the bartender, so I was quick to agree. The evening bartender came out of the back bar area and told us we could go back when were were ready. He had turned the game on and said he would be back occasionally to check on us until the second bartender showed up for the evening.

We all grabbed our glasses and headed back to the other bar. It was a much darker room with a long bar along one wall. Across from the bar was a long bench along the wall opposite the bar. There was just one TV on with some random beer commercial playing . We all gathered some barstools around and I took my place next to the bartender I had been flirting with. He asked me if I was a betting man. He said they sometimes make bets on games to keep things interesting. I was drunk enough I was prepared to go along with anything he wanted that evening so I said to count me in! He asked if the other guys wanted to join the bets and they all said they had to work the next day and would have to leave before the game was over.

He said it looked like it was just going to be me and him betting. I was just fine with that because I was hoping it would end up with us going home together after the game. I asked him what the bet was because I didn’t have much cash on me. He said ‘why don’t we make it really interesting since it’s just two of us betting. We can each pick a team. Every time your team scores you get to take a item of clothing from the other person. “

This instantly made my dick jump. 

I thought I would push the envelope a bit further and asked what happens if we lose all our clothes and the game isn’t over? All the guys had suggestions. Most of their suggestions involved blowjobs. The bartender got up and walked around the end of the bar we were sitting at. He rummaged around for a bit and then set a large birthday gift bag on the top of the bar. He said his birthday was last week and a bunch of his customers had brought in gifts. He said that if one of us lost all our clothes, the other person got to reach into the bag and pull out one of the items. That person then got to choose if they used the item on themselves or on the loser. 

I stood up and looked into the bag to see that it was full of sex toys, lube and leather items I couldn’t even identify. 

Again, this made my dick even harder.

I was drunk and horny and agreed without hesitation. All the guys were loving the bet. The bartender said it was just his birthday, so he should get to pick his team first. I knew nothing about football so it really didn’t make a difference to me.

He chose the guys in the blue uniforms and it appeared the game was already started with a zero - zero score. The game seemed to go for a while with no score. We had another round of pitchers delivered from the front bar and just as I was pouring my beer the guys started cheering. The blue team had just scored. The bartender stood up and walked over in front of my bar stool. He said “ time to pay up!” He grabbed the bottom of my shirt and quickly lifted it over my head. 

He tossed my shirt up onto the bar and then took a moment to squeeze and tease my nipples until they were hard. It was a little cool in the bar so they just stayed that way when he sat back down. I was now starting to watch the tv, hopping that my team would score so i could take his shirt off and get a good look at his muscled chest. My team grabbed the ball and took off down the field. About half way the guy tripped and dropped the ball. The blue team scooped it up and I watched as they zipped the opposite direction and scored again. 

The guys sitting around went nuts cheering and teasing me that it was time to pay up again. The bartender stood up and walked over to my barstool again. This time he motioned for me to stand up. When I did he popped the button my shorts and then lowered the zipper… Then he took both sides of my shorts and slid them down to my ankles. I stepped out of them and was glad I had put on a pair of boxers that day. He tossed my shorts up onto the bar next to my shirt and then gave my hardon a squeeze through the front of my boxers. The other guys were loving it. I sat back down on my bar stool and started to chug my beer out of nervousness. 

The conversation stayed pretty focused on my abs and chest. Another round of shots showed up from a new guy who must have been the second evening bartender from the front bar. Just as we were passing out the shots, the guys started cheering again! I looked up to see the blue team had scored again! I don’t even know how it happend so fast. 

The bartender walked over to me again and motioned for me to stand up. I instantly turned red from embarrassment. I slowly stood up and he squeezed my dick through the front of my boxers again. Then he slid them down over my hips and further down until my deck sprung free and bounced in front of me. They guys were going nuts and moving around to get a good look. The bartend had bent down to lower my boxers to my ankles and then waited for me to slowly step out of them. He grabbed my hard cock with one hand and then tossed my boxers up on the bar with the rest of my clothes.

There I stood with my tennis shoes and baseball cap on and nothing else. The bartender then sat back down on my barstool and pulled me backwards into his lap so all the guys had a perfect unobstructed view of me with my boner sticking straight out in front of me. 

All their attention had me supper turned on. The bartender sitting behind me was rubbing my sheet in nipples before slowly running his hands down my stomach over my abs and ending up with my dick in one hand and my balls in the other. I was both drunk and horny. I was also getting off on the group of guys watching me get groped by the hot bartender. This went on for a while until the guys were cheering again. Blued scored again. Without getting up the bartender grabbed me by the waist and lifted me up until I was sitting on his lap. Then he told the guys “ Alright, someone take his shoes off.“ Two of the guys jumped up and were on their knees in front me. They quickly whipped off my converse leaving me barefooted. 

There I was sitting naked on the bartenders lap with just my baseball cap on. Now the groping really ramped up. He basically held his beer in one hand and started slow jerking my cock with his other hand. The guys put my shoes on the bar and then returned to their stools to watch the show. 

I was about as read and embarrassed as I had ever been. But my dick was also harder than it had ever been. I never realized I was an exhibitionist, but I was for sure turned on by the scene. After a while I was really getting into the handjob while looking into the other guys eyes. The conversation continued along with the drinks and in no time the blue team had scored again. The guys cheered and then the bartender took my hat and tossed it onto the bar. 

Now I was totally naked. Hard dick. And exposed to a group of near strangers. 

The bartender said “ I have to take a piss, I wouldn’t put my bare feet on the floor if I were you”. I wasn’t sure what my other options were until one of the other guys stood up and walked over between my legs. He reached down and scooped his hands in between my legs, running his hands up the back of my thighs then under my ass cheeks. Then he lifted me up off the bartenders lap. I grabbed onto his shoulders until he had lifted my hips up to his chest. This put the tip of my hard dick right at his chin. In the same motion as he lifted me he slid my dick into his mouth. 

I didn’t even have time to react…just to groan with pleasure as my dick slid into his mouth. He spun me around and then sat me down on top of the bar. My ass hit the cold metal bar top and he started bobbing up and down on my dick. I just rested my hands on the back of his head and let him continue the blow job. I was starting to really get into it when he stood up and walked back to his barstool to sit down. 

Now I was sitting on the bar naked with a raging boner. As the bartender came back from the bathroom he made no effort to rescuer me from my perch. He took his seat and all the guys continued to take in my show.

More beers were poured and before I knew it the blue team scored again. The guys went nuts and they basically all jumped up to grab the back of sex toys. They started to pull things out the bag. They passed the dildos, cock rings and nipple clamps around. After a few minutes the bartender had selected some nipple clamps connected by a small chain. 

He walked over top the bar and took his time teasing each nipple before slowly attaching a clamp to each nipple. It took so long that the blue team scored again! And the guys started digging in the bag again. I couldn’t believe my team had not even scored ONCE! What the hell!

I was starting to adjust to the nipple clamps when the bartender walked up between my legs with a large metal ball stretcher in his hands. I had been so turned on for so long now that my balls were pulled up snug between my legs. He grabbed my balls with one hand and then asked one of his buddies to come over and help. TWO of them stood up and walked over. He said “ ok, lean back and spread you legs.“ Shocked and horny I did what he asked. They spread my legs apart and started working and stretching my balls away from my body. I was leaned back on my elbows. One foot up on the bar and the other being held out chest high by one of the guys. They were working my balls into the ball stretcher when I felt someones finger slide in between my cheeks and across my asshole. I then realized that my legs were spread apart wide enough that they were all getting an unobstructed view of my hole. As I felt the pressure and weight around my balls I could also feel one of them rubbing circles around my exposed hole. I couldn’t help but let out a groan which got a round of cheers from the group of guys watching my show.

When the stretcher was attached they all took a step back to look at me. One foot on the bar, balls hanging over the edge and other foot swing off the side of the bar. I sat up as one of the guys handed me a beer. As I took a drink I realized that I needed to take a piss. I told the bartender I needed to piss from all the beer I had been drinking and he started to chuckle. He said “ Ok, but you are going to want your shoes back for that. What are you willing to do to earn your shoes back?” I was at a loss, not sure what to offer. 

They all started make suggestions and finally landed on either me sucking a dick of my choice for 15 minutes or allowing them to choose another toy from the bag. I didn’t think I had 15 minutes before I pissed on myself so I chose the bag. The bartender reached inside and pulled out long rubber dog tail. All the guys started laughing and joking with each other. The bartender said ‘ grab your shoes and take a piss - then come back and we will take care of this”

I grabbed my shoes and slipped them on. I hopped off the bar and headed to the bathroom. My dick was bobbing in front of me and I had to walk kinda bowlegged because of the large ball stretcher between my legs.

While I was taking a piss I heard the guys erupt in cheers again. As I walked back across the bar to the the group of guys they were laughing and pointing at the tv. The blue team had scored again. The bartender said” You can’t catch a break!”  He was chuckling and said “ I’ll make you a deal. I’ll put the dog tail back in the bag and let you keep the shoes. But we have to let the guys pick another toy from the bag for me to use on you. OR - I can put the dog tail on you and choose another toy myself.”

I really didn’t want to wear the dog tail all night so I choose to let the guys pick. They had clearly already made a decision. I should have known better. They reached in to the back and pulled out a large rainbow colored strap on dildo.

The bartender got a huge smile on his face. He took the dildo from them and started stepping it on over his jeans. Once it was strapped on he started wiggling his hips back and forth so it was slapping from one hip to the other as he swung his hips.

The guys were cheering and laughing. They handed the bartender a bottle of lube and I watched him lube up the strap on. They were all cheering him on. He sat the lube on the bar. He picked up one of the bar stools and then sat it out toward the center of the room away from the bar. Then he grabbed me around the hips and led me over to the barstool. He bent me over at the waist and took my hands and put them on the barstool. Then he used his foot to spread my feet further apart to expose my hole. I was leaning on the barstool facing the door of the bar. My cock was hard as a rock. I felt him put the cold tip of the dildo against my hole and I braced myself of the barstool.

The group of guys gathered around and I stood there waiting for him to push inside. My knees were starting to shake but nothing was happening. I turned and looked over my shoulder and the bartender had a huge smile on his face. Once my eyes were locked with his he started to lean forward and slide the dildo into my ass. I couldn’t seem to look away as I felt my hole stretch and the dildo slide in inch by inch. The guys were cheering him on, laughing and having a great time. Every couple inches he would stop and let my hole adjust. Then he would start moving forward again. He repeated this until he was “balls deep“ in my hole. He reached up and grabbed my hips and I braced myself. 

He started to slowly pull out of my hole until just the tip was inside. The he reversed course and started to impale me on the strap on again. All the way in. All the way out to the tip. All the way in. All the way out to the tip. All the way in. All the way out to the tip. 

The guys were loving the show. Some were rubbing my arched back. Ruffling my hair. One was tugging on the chain attached to my nipple clamps. And all the while the bartender continued the long slow deep fucking of my hole. 

One of the guys grabbed the lube off the bar and slicked up my hard dick. Then he took one of my hands and moved it to my dick. He said “ stroke yourself but don‘t cum. You don’t want to take this fucking after you shoot your load.”

I started to jerk my dick while I balanced myself on one hand on the barstool. I was bent over the stool in the middle of the bar. Jerking my cock and getting fucked by a strap on while a group of near strangers watched and cheered me on.

It was hot. Embarrassing. And the sluttiest moment I could remember. I was starting to get into it. I  kept myself of the edge of orgasm. The bartender had picked up the pace and the guys were cheering him on when one of them said “ Oh fuck! Another touchdown! “ 

They all went wild. They grabbed the bag and brought it over to set it down in front of me. The bartender kept up his pounding and I kept tugging my dick, not sure what would come next. 

I was grunting with each thrust. The guys were digging around in the bag. All of the sudden a group of new guys walked in from the front bar. They were walking straight toward us and felt my entire body blush with embarrassment. I hadn’t even realized how strangely the night had progressed until i took in the moment. 

I was the only one naked in the bar. Wearing only my tennis shoes, nipple clamps and a ball stretcher. Bent over a barstool in the middle of the bar. Letting a dude I just met fuck me with a strap on for a crowd. 

As the new group surround us everyone started introducing themselves. Then they turned the focus to me. The bartender tightened his grip on my hips and started to pound my hole without mercy. He was pounding me so hard I had to let go of my dick and hold on to the barstool to keep from falling over.

As they were all watching me get pounded I felt one the guys reach down and start milking my dick. I was getting so close to cumming. My hole was warmed up and easily taking the dildo now. This just caused the bartender to pull all the way out occasionally and then slam balls deep again to hear me grunt. 

One of the guys was telling the new group that I lost the bet. He was explaining the rules and how I had found myself being whored out in public. The guys were laughing a little to hard and whispering something in each others ear. As everyone learned the secret they all began laughing and joking in on the inside joke. 

My knees started to tremble as I neared orgasm. I was grunting from the pounding my hole was taking and I felt by body tighten, my back arch and then I was hanging on the edge of agony. The guy milking my dick started pounding faster in time with my hole pounding and I finally tipped over the edge. 

I started to see stars and I began cumming. The bartender never let up his pace and the guy milling my dick starated to rub the head with his palm as cum was still bursting out blast after blast. The over stimulation made me start to scream from please and the guys cheered me on. 

Just when I thought I would pass out the guy let go of my dick. The hole pounding continued and my dick and balls bounced between my legs. 

The orgasm started to wear off and the embarrassment flooded in. I could feel how sensitive my hole was but the bartender continued to pound my now loose hole.

I don’t know why I didn’t try to stand up but as I came down from my orgasm I continued to bend over the bar stool and let the bartender Use my hole for the crowd. 

They all continued to laugh and whisper and finally one guy said to the bartender “ Hey dude, should we let our little slut in on the joke?”

It took a minute for it to register what he said. Joke? 

The hole pounding continued and one of the guys was squeezing more lube onto my hole as the strap on continued it’s pounding. 

I stretched to look around over my shoulder and the bartender had a huge evil smile on his face. He kept fucking my sloppy loose hole as he said “ I have to confess. When you said you didn’t know anything about football, I didn’t believe you. “ 

Now he pulled all the way out with the dildo and spit on my ruined hole. Then he slid the dildo balls deep again. He said “ Hey guys, help me lube up this little pig”. Then he pulled all the way out again. Two of the dudes leaned in and spit on my gaping hole. Then the bartender slammed balls deep again. Then he pulled out and different guys spit on my hole.

my hole started making sloppy sounds and I could feel the spit running down my crack and my balls.

The bartender caught my eyes again with that evil grin and said “ Ok, I confess, the game we are watching is a rerun. I knew exactly how many times my team would score.” 

It all started to sink in. They kept spitting on my hole as the bartender pulled out and then slam back in. They all knew I would lose. The whole time.

The shock set in. The orgasm had worn off. My hole felt like it was on fire. 

He said “ At first I thought you were just a little slut looking to get used. Now I can see you really knew nothing about football. But the fact that you are still bent over taking a public fucking shows that your were built to be a bar whore!”  He pulled out and slapped my ass. All the guys left me out in the open and walked back over to the bar. Chuckling and laughing among themselves. 

I slowly stood up. My hole was on fire and I walked bowlegged back to the bar where my clothes were. All the guys drank their drinks and watched me slowly take off the nipple clamps and ball stretcher. As I reached for my clothes the bartender said. “ Hey, I’l make you a deal. Let each of these guy take a ride on your ass with this strap on and I will erase the security camera videos of what you did tonight. Or, you can get dressed and leave. I will do my best to not let that end up on Pornhub.” 

Oh god. Was I going to be on PornHub? I did let that all happen in a public bar!. I didn’t really have much of a choice. I looked at the bartender with the evil grin and then slowly walked back over to the barstool. He said “ Assume the position!” The guys cheered and they all started to walk back over. The bartender handed me the lube and said. “ You better lube up good and this time don’t cum. It will be much better if you edge yourself until everyone is done having fun…..”