Halloween In Chicago

If you have never been to Chicago for Halloween you should put it on your list. I had just moved to Chicago in July and was starting to make some good friends. I met a few guys at the gym and had been hanging out with them just about every weekend. Altogether there were 7 of us in the group. Basically, it was three couples and me. But nobody made me feel out of place. They all three had open relationships so at times it almost seemed like they were all single too.

We had been planning on hitting a few bars Halloween night since it fell on a Saturday this year. We all agreed to meet up at James and Bob’s house after the gym to have a few drinks and then head out. James and Bob were in their early 50’s but both had hard earned gym bods that gave them the rugby player build I enjoyed. I had met Bob at the gym because he caught me checking him out in the locker room. He had the most beautiful thick cock. Even soft it hung down at least 6 inches and rested on a nice set of balls. I saw him in the steam room one day and was caught staring at that cock. When I looked up from his cock and our eyes met, he had a huge smile.

We were alone in the steam room and he said ‘You got a pretty nice cock yourself. I’ve seen you in the showers here before. ‘ I was a little caught off guard but Bob had a very charming and disarming personality. My quick response backfired on me a little when I said ‘Thanks, I’m a grower – not a shower like you.’. Bob laughed his deep charming laugh and said ‘Really? How big does it get?’. At this point I didn’t know Bob had a partner so I said ‘You’ll have to check it out sometime.” Bob stood up and walked over to sit down next to me. He smiled as he said ‘ No time like the present’. And with that he reached over and grabbed hold of my cock and started to stroke it while he looked me in the eyes.

His rugged handsome stare kept me captivated and I let him continue to jerk me until my cock was rock hard in his hand. True to my work – my cock grew to a solid thick nine inches. After Bob got me hard he continued his slow teasing hand job as he held me with his gaze. I was so turned on by the situation that I was close to shooting my load no time. Bob could tell my breathing was getting faster and he asked me if I was close. I just shook my head yes and he said ….’hold on a little longer. Wait for me to tell you when to come.’ Bob slowed his stroking to a super slow torturous pace.’ I was riding the edge of the orgasm until my body was quivering. Just when I didn’t think I could hold out any longer the cool breeze hit my body when someone opened the steam room door and walked in. I jumped and tried to get my towel out from under my butt to cover up my raging boner.

Bob made no attempt to let go or stop his stroking. The took notice of what was happening and I just waited for him to say something. Instead, a slow smile stretched across his face and instead of leaving he walked over and sat down on the other side of me. He was staring at my cock and said ‘ Hey Bob, who is your new friend?” The two chuckled and I was introduced to his partner James. Bob continued his stroking and I started to get back into it. James was running his hand over my chest and down my stomach. He traced around Bob’s hand and then slid down over my balls. His hand continued a little lower until his middle finger traced my taint and then slid over my asshole. Bob’s hand job was so intoxicating that tilted my hips back without even thinking about it.

That gave James better access and a clear green light that I was enjoying myself. Bob continued his hand job as I started to reach my limit again. I could feel the orgasm building and then without warning James slipped his middle finger in my ass up to his second knuckle. This sent me over the edge and I started to shoot a huge load up across my chest, shoulder and face. James continued his finger fucking as Bob milked the load out of my cock. Right at the peak of my orgasm I felt the cool breeze hit me again as someone else opened the team room door and walked in. Being caught in the middle of my orgasm I could stop the load squirting out of my cock over in pulse after pulse. The new guy came in and took a seat directly across from us and started watching the show. James and Bob had been jerking their own cocks and almost in unison they stopped fingering me and stroking my cock.

They stood up and I started to feel the first hot splash of cum as Bob unloaded on my face which was now eye level with his cock. Then in quick succession I started to feel James’ load splashing across my shoulder and the other side of my face. After shaking off the cum dripping from their dicks, Bob patted me on the head and said ‘Nice to meet you. We didn’t catch you name before.’ My orgasm was melting away and the world was coming back in focus. The guy across from us was still watching. I stammered out ‘Rex’ and with that Bob ruffled the hair on the top of my head and said ‘ Nice to meet you Rex. And you are right, you are a grower.’

With that they walked out of the steam room and left me there with the new stranger staring at me legs still spread, fresh finger fucked hole exposed and my face covered in cum.

The embarrassment hit me like a slap and I jumped up and grabbed my towel and walked out of the steam room. When I came out I almost slammed right into two hulk looking guys coming around the corner. They started giggling and one of them said. “Whoa, slow down dude. You got a little something on your face there.’ As he pointed to the cum dripping down my face. I’m sure I turned a whole new shade of red from the embarrassment. I turned the other direction and made a dash for the showers. When I go to the showers they were all full and I was forced to stand outside and wait. The two guys I nearly bumped into came around the corner to stand next to me. It seemed like forever before one of the showers turned off and with my towel around my waist I couldn’t wipe the cum off my face, shoulder and chest. So I had to stand there while the guys laughed and whispered and stared. When the shower curtain opened out stepped Bob. He said ‘ Hey Rex, it was nice to meet you in the steam room. Why don’t you get cleaned up and join James and I for a beer. We will wait for you out front.’ Completely caught off guard I said ‘ uh ok…be out in a sec’ and then jumped into the shower to hid behind the curtain.

So that was the first time I met Bob and James which pretty much set the tone for our friendship. Like I said we had been hanging out for a few months and I had become more comfortable around Bob, James and their playful friends. At drinks last week we were talking about Halloween and decided that we would all dress up in a sort of group costume. I said I didn’t really care. Just let me know what I need to buy. Bob said he would take care of everything and we should all meet over at his house before we go out.

I arrived to Bob’s a little later than everyone else because I was later getting out of work. When I walked in they were all wearing white towels around their waists, shower caps, and they had soap-on-a-rope around their necks. They had also got a back scrub brush and little yellow rubber duck to round out the outfits. I started laughing and had to admit it was a cute costume idea. It was bit skimpier than I expected. But since we were all in the same boat I didn’t really give it a second thought. Bob said my towel and other costume parts were in the bedroom and that there was a pair of white flip flops to go with it. I stepped into the bedroom to get changed and then had a startling thought. I had chosen to go commando today. So I didn’t have any underwear to wear under the towel. Wasn’t much I could do at this point so I just stripped down and put on the towel. I decided to leave the cock ring on that I had picked out for the night because it made the front of my towel stand out with a night bulge. I walked back into the living room and asked Bob how we were going to carry our phones, ID’s and credit cards in this outfit. Bob said he could carry my ID because he had a little wallet bracelet that strapped around his wrist. He said I wouldn’t need my phone because the other guys could call our Uber. So I gave Bob my ID and credit card and left everything else on the bed with my clothes.

We decided to make the first stop at a bar called SoFo. It was neighborhood bear bar with hot bartenders and a cute back patio. It was an unusually warm night for this late in October. It was just cool enough to make my nipples a little hard but not too bad. When we arrived to the bar we grabbed some drinks and headed to the patio. They had the heaters going and I found a place under one near the outside bar. Lots of guys came up and wanted to take pictures with our group. As the night went on we had a number of shots and beers bought for us.

When we got in the Uber and headed to the next bar called Jackhammer. Bob and James convinced me to take a Cialis. Not that I needed any help getting a hardon – but it was great to recover quick so you could go all night if needed. The only drawback (which I didn’t think about at the time) was that the slightest breeze would trigger a raging hard on for the rest of the night. We arrived to the next bar, grabbed a drink and headed to the back patio. We were standing around chatting to another group of guys all dressed in leather when I noticed one of the guys from our group with his towel around his neck. He was wearing a pair of shorts and I realized for the first time that maybe the other guys were not going commando like me. The thought of it made my dick stir a little and the Cialis helped it along.

I went to the bathroom and when I got back to the patio I couldn’t see anyone from my group. I walked through the bar and still couldn’t see anyone. I thought maybe they had gone over the bar next door so I headed to the front of the bar and out the door. It was a much smaller bar with a back bar that was in a separate darker room. The back bar was famous for a more sexually charged atmosphere. As I entered there were a lot fewer people than I expected – but I guess it was still ab bit early for this kind of bar since they were open until 4am.

I walked to the far end of the bar and up to the bartender. I asked if he had seen any other guys in towels like mine. He said he had not and asked if I wanted a beer. I said sure and as he sat it down I realized that Bob had my credit card. I was really embarrassed and told the bartender my situation. He laughed a little and asked what I had to barter with? I giggled nervously and said all I have left is this rubber duck. Throughout the evening I had given away my shower cap, scrub brush and soap-on-a-rope.

He said he would make me a deal. He would buy my beer but I would have to leave my towel and duck as collateral until my friends showed up. I let him know that I wasn’t wearing anything under the towel and his smile got even bigger. He said that was ok – I could just stand at the end of the bar and would be hidden from most of the bar. My buzz was pretty good and I was out of options. I slipped off the towel and set it on the bar next to the duck. The bartender took it and set it behind the bar next to the liquor bottles.

Let me know if you would like to hear more about this adventure. Leave a message in the comments.