James and Greg Differ on Strip Poker

After graduating from college in Pennsylvania, I moved to Boston for my first full-time job. It was a little harder to make friends in a new city than I expected, and I found myself spending a lot of time in online chatrooms. Now that I was in my 'adult' life, one of the things I missed the most about college was: in college it was so common to see naked guys, either in the gym or just streaking the dorm hallways. I had moved to Boston in January, so beaches weren't really an option (and I don't think I was aware at that time that there was a nude beach in Provincetown, 3 hours to the southeast). I'd been in Boston now for nearly 6 months, and had yet to see a naked guy.

So, there was this guy Greg from #gayboston that had been asking me out to dinner for several months. I had always politely declined. Mostly I was just a shy 21 year old and afraid to meet in the 'real world'. Greg was 25 and a chef in Boston.

After six months of surfing internet porn but not seeing a live penis (other than my own), I invited Greg over for a game of strip poker. I really wanted to see a naked man, and figured it was an acceptable trade/compromise that a guy might also see me naked. Greg was quick to say yes, and he arrived at my apartment in less than 30 minutes.

We made small talk for a short while, then Greg asked, "should we get started?"

I agreed and walked over to my dresser, where I thought my deck of cards was in one of the drawers. I opened and rummaged through all six drawers, but could not find my cards. I hadn't used them since I had moved to Boston, but I would have sworn that I had packed them in the dresser drawers. Greg was becoming impatient, "Do you have anything else we can use?"

I don't know why I didn't think of Trivial Pursuit or Monopoly, but instead I replied, "I have a quarter."

"That will work," said Greg.

I asked him if he wanted to be heads or tails. He said, "heads." I flipped the coin and it landed on the floor with heads up.

"Great," I said, "take something off."

He looked at me and said, "No, I'm heads."

I said "I know you're heads; so take something off."

He argued, "No, heads means I win; you have to take something off."

I said, "Fine, but that means if it lands on tails you had to take something off."

Greg agreed. So, I took off my t-shirt and handed Greg the quarter. He stared at my tan chest for a little while, and then tossed the coin. Heads again! Greg smiled, "That's still you." I stood up and took off my shorts. I realized things were not looking good. I was down to just my boxers, and Greg hadn't even taken anything off yet.

I flipped the coin again. Tails! "Finally," I thought to myself. Greg bends over and unties a shoe, and slips off his shoe, and then asks me for the quarter.

I said, "Not until you take something off."

He says, "I just did."

I replied, "No, a shoe doesn't count."

He answers, "A shoe counts as clothing."

"But that's not fair, I'm not wearing any shoes," I reply. Since it was summer, and I was in my own apartment, it was customary for me to walk around barefoot, and it never occurred to me to put socks/shoes on simply because someone was coming over.

Greg says, "Hey, it's not my fault you chose not to wear shoes."

We argued back and forth a bit, and finally achieved a 'compromise' where Greg took off both shoes, counting them as one item. However, I did some quick mental math, and the picture still looked bleak. Greg still had on socks, as well as his shirt and pants, and presumably underwear. I was down to my last item (boxers), so I would have to hope for a series of lucky tosses.

Greg tosses the coin. Tails again! He stands up, and I'm thinking he's gonna take his shirt off. But no, he undoes his belt. Again I protest, "belts don't count." Greg insists that belts are clothing, and it isn't his fault that my gym shorts didn't have belt loops. Ugh, I cave in and allow him to take off the belt. After all, there have been two tails in a row; maybe my luck is changing.

Greg hands me the coin, and I give it a flip. Heads. Greg looks at me in anticipation. I had been sitting there thinking what I could possibly 'invent' as clothing, but other than boxers and the hair on my head, I didn't have anything that would come off (and I just couldn't foresee shaving my head to count it as 'clothing'). I stood up, and pushed my boxers down, and stepped out of them, and then sat back down on the sofa.

Greg and I continued chatting. He asked about where I went to school, the farm I grew up on (I guess he noticed my farmer's tan), my work, and various other things. About 45 minutes had passed before I even realized how much time had elapsed. Greg took advantage of the first awkward pause in the conversation to ask, "what do you want to do next?"

I said, "I dunno."

He said, "Do you want to kiss?"

I said, "No."

He looked a bit offended and said, "well then, why did you invite me over?"

I replied, "to play strip poker."

He repeats, "and then?"

I explained, "No, I just wanted to see you naked. I wasn't looking for anything more."

He seems to be getting a bit angry and calls me a tease. I argue, "I didn't mislead you at all; I told you what I wanted to do (i.e. play strip poker)."

He tells me that "strip poker is a code for sex; like if you invite someone up to your place for coffee, you're really inviting them for sex."

I apologize, and re-state that really my interest was solely in seeing him naked.

I think that was the first point that I realized I had been sitting there still completely naked while chatting with Greg, who was still rather fully clothed (minus only shoes and a belt).

Greg says, "so, would you like to see me naked?"

I said "yes" with great expectation, thinking he was going to stand up and do a strip tease for me.

He said, "ok, I'll give you double or nothing."

I asked, "what do you mean?"

He says, "If it's tails, I'll take everything off...if it's heads, we kiss."

At that point in my life, I was still coming to terms with my sexuality and had not yet fooled around with a guy, and I wasn't ready to kiss a guy. I tried to explain this to Greg, but I could sense he was getting a little agitated. He announced that he was gonna leave.

I said, "but don't I get to see you naked? It's only fair...you've seen me."

He replied, "You lost, fair and square." He then offers me one final "all or nothing" proposition. "Tails, I'll take everything off...heads, I get to take a picture of you."

I'm somewhat relieved by the offer; it doesn't involve anything sexual. I tell him, "okay."

Greg grabs the coin off the floor and tosses it. It bounces off the arm of the sofa and lands heads-up. I say, "Do over; it hit the sofa."

He replies, "That's a valid toss. I'm not tossing it again."

We argue a little bit more, but finally I relent... fine "game over, you won." Greg tells me that he has a camera in his car, and he'll be back in a few minutes.

Two minutes later, Greg knocks on my door, and I let him back in. "Where do you want me?" I ask.

"Stand over there by the TV," Greg says. He snaps a pic. Then he tells me to go stand by the refrigerator, and he snaps another pic. He directs me to go stand next to the sliding glass door, and he takes another pic.

I said "Hey, the deal was just one picture."

He puts his camera down, puts it into his backpack, and gathers up his stuff, and walks to the door. As he's leaving he says, "You know, when I suggested taking a picture of you, I had presumed you'd at least be in your underwear or something."

It hadn't even occurred to me when Greg walked out to the car, that I should put something on, so I was still fully naked when he returned. I responded, "Hey that's not fair, you should have told me to put something on."

Greg simply looked at me with a puzzled look, and said, "It was nice meeting you," and pulled the door shut.

The next evening after work, I logged onto #gayboston to chat. I wasn't in the room long before a guy typed, "Hi sweetcobs. Nice pictures."

"What do you mean?" I typed back.

He responds, "I heard your lost as 'strip flip the quarter', lol."

"Who did you hear that from?" I ask.

"McGreggor told me," the man types back.

Then another guy types, "Wait, are there pics from this?"

The man responds, "Yeah, Greg sent them to me this morning."

"Can you send them to me?" types the other guy.

"Check your email."

And that was my introduction to Boston men.