Phil had been part of my larger friend group going back to our college days, and I had always suspected he was gay, but never knew for sure. Since my divorce, he had taken a stronger interest in me, and I was more than open to the attention. We had been good friends back in the day, lotta fun drunken nights out, but eventually, we drifted apart.
After discovering my 'other' side, I started realizing his friendliness might have been more than just about being buds, and I made an effort to start reciprocating. Knowing he was coming out tonight, I had put on one of my best shirts, got a haircut, and tried to look as presentable as possible. Half the night passed before I was able to inconspicuously sidle up to him. I had bought a round of beers for everyone, and a Patrón and soda with lime for him, which I remembered was his favorite drink from ages ago.
"It's nice to know I made a lasting impression on you," Phil said.
"I've always been a people pleaser, and I think it's cool you have a signature drink. It sets you apart from the Bud Light crowd," I said.
"Among other things," he replied. "You know we should hang out more. We used to hang out a lot back in the day, and it was a ton of fun. Whatever happened?"
"I got married, settled down to a boring life of network procedurals and house repairs," I said.
"I'm sorry, I fell asleep, what were you saying?" He had a grin on his face, pleased with his own joke.
He wasn't wrong, my married life had been slow. It wasn't just getting older, it was like someone had turned the vibrancy down on life.
"Exactly. Life got boring, I got boring. But that's in the past. I'm free now and trying to make up for lost time. I've been hitting the gym, getting out more, trying new things. It's super cliché, I know, but I'm trying to say yes more," I said, with genuine excitement.
It was true, though I left a lot of details unsaid. I'd been experimenting sexually and finding my place as a submissive. Trying new things helped me find my boundaries, and even the things I didn't like taught me more about myself.
"So, if I asked if you wanted to hang out tomorrow, you'd say...?" he asked.
"I'd say yes, let's do it," I said, trying to keep my smile from giving too much away. I didn't know if this was a date. We had hung out alone many times and while I was straight then, he had never made a move. I decided to proceed with caution.
We continued chatting for a bit, until our friend group started breaking up for the night. Phil told me to come over at seven-thirty, and texted me his address.
I spent the next day, overanalyzing everything. What I should wear, how should I present myself, should I bring a gift, and so on. I settled on a shirt that looked nice enough to show I was putting in an effort, but not so much that it screamed 'date night'. I went out and bought a bottle of Patrón, thinking that it would be a nice-but-neutral gesture. Lastly, I had learned enough about bottoming to prepare myself in advance.
I had started to take pride (and pleasure) in getting myself ready. I lathered up in the shower and shaved my balls and ass, then trimmed the hair above my dick to a neat half-inch with my body groomer. I made sure to clean my ass thoroughly with the shower sprayer, in hopes Phil would appreciate it later. When I got out of the shower, I checked myself out in the mirror, and felt like I was doing pretty well. By the time I left my apartment, I felt like I was nailing this-- my confidence was high that I was going to get laid.
When I arrived at Phil's apartment, I knocked and someone I didn't recognize answered the door. "Uh, is Phil here?" I asked, with a very puzzled look on my face.
"Oh yeah, he just went to the bathroom, you're Derek? C'mon in, the game just started."
The blackhawks were on TV, and while I did like hockey, I had been hoping to do a different kind of stick handling this night. My gut sank, I had completely misread the situation. Here I was with my shaved junk and squeaky clean asshole holding a bottle of Patrón, trying to hide my disappointment.
"Cool. I brought tequila," I said, trying to hide my disappointment. Phil came out and offered me a beer, which I took readily and handed him the bottle of Patrón.
"Thanks bud! I hope you don't think we're finishing this tonight, it's only the three of us. I do want to be able to walk tomorrow," he said. He took a seat on one end of the couch, while Joe was sitting on the other. I wanted to be closer to Phil, even if it wasn't a date, I could at least, maybe, get some accidental touching in. So I took a seat in the middle.
"Sitting in the bitch seat, I see?" Joe said.
"Better viewing angle for the game," I said, trying to cover my tracks.
The game was ho-hum and I was leaning into the tequila. Joe and Phil clearly had a rapport, and they were cracking jokes I didn't always understand. As the tequila bottle got lighter and lighter, I noticed the jokes getting dirtier and dirtier. I didn't think much of it, typical guy stuff. I tried to play along, and by third period, I had a decent buzz going. I looked over and saw Joe and Phil finishing their drinks.
"Let me take care of that for you guys," I said, and got up to make more drinks.
"The game is shit, but the service here is excellent," Joe said.
I felt my face blush, as I picked up their glasses and headed off to the kitchen. I could hear them talking in low voices in the other room, but couldn't hear what they were saying. I came back with fresh drinks, and when I leaned over to put them on the table, Joe had a big smile on his face, and was holding a one-dollar bill. He reached out and tucked it into my belt, as I put his drink on the coffee table.
"I know you're joking, but I'm pretty broke right now, so I'm keeping it," I said.
"You earned it, hon," he said, and I could feel my face flush again.
I sat sipping my drink and trying to focus on the game. Both guys were lying back in their seats, man-spreading across the couch. My left knee was touching Phil, my right knee touching Joe. I didn't know what to do with my hands, I laid them on my thighs, just barely touching both guys' legs. Even that little bit of contact was getting me excited. The mix of booze and the hints of flirting were taking their toll, and I was getting aroused. I didn't really know if I was trying to flirt with Phil or Joe, I was just getting horny, and wanted more attention from these guys.
I waited until the tallest player, Crevier, got checked, and I said, "See? Even the big guys get pushed around sometimes."
The two of them looked at each other with devilish grins, and then just started pushing me back and forth on the couch between them, like a ping pong ball. I turned beat red, I could feel my dick getting hard.
"The key to taking down the big guys is to gang up on them," Phil said.
I was rock hard by then.
Phil told me to freshen up their drinks, and I stood up; without thinking, I was tending the front of my pants. I tried to shift and hide it as I grabbed their glasses and shuffled out of the room. My face was bright red and my breath quickened. I felt a mix of embarrassment and excitement that I knew was only going to make my erection worse. I could hear them laughing in the other room, and it only fueled the fire inside me. When I came back in, holding their drinks, they were both grinning ear to ear.
