Dan and I had been friends since high school and now that we were in our early thirties, it felt like no time had passed. We still hung out and played video games. Drank beer and shot the shit. You know those kind of friendships. We'd both had girlfriends and Dan still had one, but I was single. My last one lasted three years and I was hurt when it ended. She dumped me for her yoga instructor saying that I wasn't sensitive enough or some bullshit like that. Fuck.
Dan was a prince of course. He took me out and got me drunk and poured me into a cab at the end. The hangover was epic but it felt worth it to have Dan there in my hour of need.
I liked Dan's girlfriend. She was cool and interesting and smart as hell. She always encouraged me to be better. That's awesome in a partner, right? And a friendship, too. Dan always wanted me to be better.
So a few months after my relationship tanked, he and I were at this bar downtown after work. Scotch and some fancy spring rolls, sitting talking about our jobs. Finance. Stock markets. That kind of shit. I was just sipping my drink when this guy came up to me at the bar and gave me a look. You know the look I mean. I'm not stupid. I've lived in the city my whole adult life. I know the look guys give other guys when they want to fuck. And this bar I knew was pretty metrosexual, open-opportunity. Dan and I liked the feeling that everyone got to have fun and no on cared.
Anyway, the guy turned to me and said, “Should I buy you a drink?”
I gave the guy a nice smile and said, “Sorry, dude, I'm just waiting for my girlfriend.” That was the line I used to cover all the bases. No one gets hurt.
He shrugged and gave me a grin and went on his way.
But me? Well I was flattered. Who doesn't like a little attention, no matter who gives it. Nice looking dude, too, so that made me feel like I wasn't an eyesore.
Dan laughed when the guy walked away and said, “Poor guy.”
I chuckled and drank my scotch. “Yeah....it makes me think that being bi is the way to go. I mean, you're open to fuck whoever is willing. That must be awesome.”
“Yeah...true enough.”
We didn't say anything more about it and kept drinking. It was one of those nights when we both knew we were going to get wasted. Friday, June, nice weather, Dan's girlfriend was out of town. The usual excuses we give for drinking too much. But it's fun, right?
The final scotch came and I was feeling a little numb and Dan's eyes were half-closed. Out of nowhere he said, “So...what if I dare you to get it on with a guy? I mean like full-on sex. Like that guy from earlier.?”
I looked at him, not quite getting it.“What...? Why the fuck would I do that?”
He cleared his throat and emptied his glass. Suddenly I knew what he was going to say. Fuck.
“This is a non-negotiable dare, Steve.”
“God damn you! A guy? How am I supposed to do that?”
So a little background is necessary, right? Way back when we were about seventeen we came up with this stupid dare thing. One night when we were piss-drunk and high, one of us – and I can't remember who – came up with the non-negotiable dare. If one of us invoked it, the other had to go along with it or feelings would be hurt or some shit like that. The other rule was that it could only be invoked one time for each of us a year so it didn't get abused.
So this was mine for the year. What the fuck?
I knew it was non-negotiable, but I had to say something. “Dan...what am I supposed to do? Invent a hard-on for a guy? Have sex with a guy? That's totally not fair.”
He chuckled and said, “Really? So you getting me to steal a bottle of that two-hundred dollar scotch from the liquor store was fair?”
He had a point. Last year that was my dare for him. So I said, “OK. Fine. So I go out with a guy...maybe I just have to kiss him?”
“No way, man. You go all the way. I don't care if you can't get it up, but clothes need to come off. And I want photographic evidence.”
You might think this was unfair, but we've required it before for our dares, so I knew I had to go along with it. I sighed. “Fine. So how do I find this guy?”
“How the fuck do I know? Go to a gay bar...or what about the dude who tried to pick you up a while ago?”
I thought about that. He was a decent looking guy and if I was going to fulfil this dare, then I at least wanted someone half-way good looking. I decided not to think about it too much. I downed the last of my scotch and stood up. “All right. Fine. Wish me luck.”
I walked around the bar, looking for him. It was still busy even though it was late and I had trouble making my way through all the people. But I spotted him at a corner table sitting with a couple of women. I walked over to them, a little unsteady on my feet, but I don't think it was that noticeable. He looked up at me and gave me that smile again. I think he was a little drunk as well, which made me feel better. I took a deep breath and said, “Hey. I'm Steve.” I stuck out my hand and he took it, looking startled.
“Greg.”
“Um...so about earlier, Greg...I was just in a mood...so I was wondering if you wanted to go out some time?”
Part of me wasn't sure if this was how guys picked each other up. I had no idea.
Greg looked at his two friends and grinned, then turned back to me. Now that I was supposed to actually go on a date with him, I actually looked at him. He had all this dark wavy hair and a pretty intense scruff on his face. His eyes were this totally cool light blue. I was right, nice looking guy. He seemed fit and was wearing a really nice suit.
He said, “Sure Steve. That would be great...let me give you my card. He pulled out his wallet and extracted a business card and handed it to me. When I took it he said, “Give me a call.”
I gave him my best fuck-me smile and decided to up the ante so I grabbed his shoulder and gave it a nice stroke, turned and left. I figure if I had to do this, I was going to do it well.
I turned and smacked into Dan who was standing right behind me, pretending to be looking the other direction. I pulled him away and we went back to the bar. I said, “You fuck! You didn't think I would do it, right?”
He looked sheepish but said, “Well, you know...I just wanted to protect my interests.”
“Whatever. Let's go. I need to sleep and not think about what you've gotten me in to.”
We shared a cab and we were quiet, but every so often he would chuckle and poke me in the ribs. Asshole.
--
The next morning I stayed in bed for a while. I was hung over – that was the main reason – but I also let the fact of what Dan had gotten me into sink in. I was supposed to what? Go out with a gay guy and then fuck him? How exactly was that supposed to work? Not to mention that I had to have evidence that I had actually done it.
The thought made me feel a little nauseous so I lay there feeling sorry for myself. But after a while, I knew I needed to plan this out. Like, I had never gone out with a guy before - and never wanted to, but that was irrelevant at this point – and even more, I had never even thought about sex with another dude. I mean come on, sure, I had watched things on Pornhub with two guys fucking a girl, but that was no help.
So on the Pornhum front, I made myself some coffee and settled down in the living room to educate myself. I went to the gay section, feeling stupid, and pulled up some videos of guys getting it on in various kinds of ways. It all felt overwhelming, so I refined it. I put in 'guys kissing'. That was a good place to start.
No surprises there. Two guys kissing is no different than a guy and a girl. No brainer. But I knew the point was that it wouldn't feel the same. That's what scared me. Ok, fine. I pulled up some clips of guys actually having sex.
Like...the oral I got. I mean I've watched girls go down on me. I know what that's all about. Having a cock in my mouth...that's another story. But I also knew that my cock in a guy's mouth might be kind of fun. I sat there trying to imagine it and my dick told me that that might be nice. Who doesn't like getting their cock sucked? I pulled it out and gave it a nice stroke. Ok. So far so good.
Then there's the whole fucking thing. I watched a bunch of clips really closely, in slow motion, in different positions. In the end I decided mechanically it wasn't that different that fucking a woman. Different hole, use some lube, otherwise it made sense. I felt better. I watched guys going at it and I could almost imagine it. At least from the top's perspective. I stroked myself and forced an image of my cock deep in a guy's ass. If I didn't think about it too much, I could keep my dick hard. Fine.
But I knew it was tenuous. I worried that when I was in the situation with a guy, my cock would shrivel up. I kept stroking and just imagined the feeling of my cock in someone, anyone. Some place warm and wet. If I closed my eyes and just concentrated on the feeling, I could feel myself getting into it. My cock was getting nice and wet. I looked down and decided to taste my precum. It wasn't the first time, and I let it sit on my tongue. Sweet and salty. Nice.
Then I went for some bisexual porn. That was more interesting, obviously. There were woman there doing all the woman things and having all the bits that woman have and the guys would do cool things with them. And it did kind of interest me when a guy sucked cock while fucking the girl. Kinda cool. Or got fucked while going down on the woman. Also cool. A chick and a guy sucking the same cock, taking the same load of cum. Very nice. I liked it when they kissed with the cock between them. That got me going and my cock finally erupted all over my belly with a satisfying buzz in my body.
So all in all, I felt better. I think I could do this. Or at least try and that's all Dan wanted. He didn't expect me to produce a video of me cumming all over some guy's face or getting ploughed and yelling my head off while shotting cum all over the place. He just wanted proof that I had gotten naked and attempted to have sex.
So I let all this marinate and then the following Friday, I called Greg. We chatted for a few minutes about nothing much, then I asked if he wanted to have dinner. I suggested this place on College Street that I had been going to for ages. Old-school Italian but still hip with really good food. He said he knew it, so we agreed to meet the following evening at seven. Done.
I felt better. Scared, but better. At least this was in motion and would be done soon.
I spent some time grooming the next afternoon. I mean, I groom when I go out with women, but I felt like there were some extra steps and I asked google for some advice about cleaning various parts of me that I normally don't spend that much time worrying about. I mean, I'm no slob. I like to be tidy and smell nice, but this...well, you get the picture.
I arrived a little late to the restaurant and the owner gave me a big smile and clapped me on the back. That felt nice. I'd been going there for so long I felt like part of the family. That's why I chose it. I wanted comfort if I was going to do this.
Greg was already there and he stood up and hugged me, which startled me a bit. He felt solid and smelled, frankly, really good. We ordered a bottle of wine and Frank brought us some bread and olives and I realized things would be just fine.
Greg said, “So, Steve...I get the feeling you don't ask guys out a lot.”
Fuck. Was it that obvious? I said, “Yeah, well...I've been off the market for a few years and it feels kind of new to me all over again.” This was kind of true, I realized.
He smiled and said, “I get it. I was in a relationship for a while that ended last year. It was kind of like I was suddenly in high school or something. Like I'd forgotten how to date.”
I laughed because it was true. I took a sip or two of wine and said, “How long were you in a relationship?”
He literally gulped. “Uh...seven years.”
That shocked me. Poor dude. “Wow. That's a long time, right?”
“Yeah, it was...”
I wasn't sure if I should ask more, but I realized I wanted to know. “What happened?”
He laughed and gulped some wine, then ate some olives as if he was trying to figure something out. Then he said, “He went to a conference and met someone. You know the story. Younger, cuter, blah blah. He came home and dumped me. I guess it had been coming for a while and I hadn't noticed.”
I wasn't sure what to say. And I felt bad that I couldn't really share...except if I said I was bisexual. Interesting. I hadn't thought of that. Instead I said, “Yeah, I get it. My ex dumped me for their yoga teacher.”
Greg smiled, then laughed. I felt a bit stupid. He seemed to notice and reached over and put his hand on mine which, if I'm honest, felt kind of nice. Simple, caring. What's not to like?
I managed to laugh and said, “Yeah, well. I'm no yoga guy, so how could I compete?”
We both laughed and I felt better. Frank brought us our food and more wine and we actually had a nice meal, good conversation, pretty chill. So far, so good.
When we were done, we got up and walked out onto College Street. I felt some questions floating around and finally I said, “So...Greg.” I internally gulped, then said, “You feel like continuing this evening? I mean...”
He put his hand on my arm and leaned in and whispered in my ear, “You mean, should we go back to your place and fuck? Is that what you mean?”
Shocked, I stepped back and said, “Uh...maybe?”
His laugh was bright and easy and he hugged me. I wasn't expecting a hug. I don't know what I was expecting, but not a simple hug. Again, I was surprised at how nice it felt. Dan and I hugged but they were more like bro hugs, if you know what I mean. This had more body contact and his arms went around my shoulders and I couldn't help but do the same.
He pulled back and looked at me. “Tell you what. You walk me home and on the way we'll plan our next date, and who sleeps where. Deal?”
I felt a wave of relief and I said, “Deal.”
Part of me wanted to get this over with but at the same time this guy was so decent, so...I don't know...nice...I didn't want to be an asshole.
We walked a few blocks along College and then up a quiet street with big trees and stopped in front of a little duplex. I noticed a cat looking at us from the living room window. Greg turned to me and said, “So next Saturday, then. I get to choose.”
I said, “Sounds good.” Then I got scared because I assumed there would be kissing and sure enough, Greg pulled my face to his and our lips met. I forced myself to go with it, so I opened my mouth and so did he and soon we were full-on necking. He gave me some tongue and I did the same and it was really fucking weird. Surreal. I felt like a fraud, mostly. Was I leading this decent guy on just for this stupid dare? So I put more energy into it and pulled his face closer to mine, and his body closer to mine. I ran my hand down his back and felt his ass. A guy's ass. It was muscular and firm and then our crotches met. He was hard. It was totally obvious. Pressing into me.
I pulled back and said, “Whoa. Let's cool this down. We'll save it for next time.”
Greg laughed and mussed my hair. He gave me a light kiss and said, “Next week.”
“Next week.” And then, as soon as he walked into his house, I totally freaked. What the fuck was I doing? I just had my tongue halfway down the throat of a decent guy and I was doing it for a dare. What kind of a shit was I? I had to tell Dan. This was going too far.
But you know the thing? The thing that, despite my freakout, despite the fact that I felt like I was leaving my body the whole time we kissed, despite the fact that I was only supposed to be in this to satisfy this adolescent dare, and despite the fact I was a total loser, I had to admit that my cock had been pretty hard when I was kissing him. Not full on, but definitely getting there. I remembered the feeling of his cock pushing against mine.
When I got home and sat in the living room with a glass of scotch, I felt like a shit. A shit who also got hard. From kissing a guy. I had no idea what to do with that.
Part of me wanted to go to the nearest skanky bar and pick up a woman and take her home and fuck her to next week. But I knew that wouldn't make a damn bit of difference. So I went to bed and shut my mind off.
