Posts Tagged chatroulette

Popping the Question

Another night went by, and I was still in the dark about where I stood in Smiles‘ eyes. He had to be somewhat interested, otherwise why would he be sticking around. However, the question remained, was he interested enough for me?

Out of nowhere, Smiles asked me to come with him to see a Christmas play in New Jersey. One of the men he worked with on his movie wrote a spoof on the Nutcracker and thought to ask me to come with him.

I was so frustrated! I was getting mixed signals in every direction. He didn’t invite me to casual Christmas parties, but he invited me to be his guest for a stage-play. I graciously accepted the invitation, but informed him I had a doctor’s appointment I would have to change if we wanted to get a ride from his friends instead of taking the train.

I managed to change my appointment, so I planned to just make my way to his apartment when I finished. I called him as I walked out of my office, but he told me he was still working. I had nowhere to kill time after the doctor really, but I didn’t exactly feel welcome to go down to Smiles’ apartment and hang out while he finished what he needed to do. I figured I would walk around Union Square and try to find something to kill time.

My appointment ended later than expected, and when I called Smiles after, he told me he was wrapping up work, and I could come by. I asked him if he wanted anything from Starbucks and walked towards his apartment.

We didn’t have a lot of time before we were supposed to be picked up, but just enough time to chat a bit and move a few more of his boxes to his storage unit.

When we got picked up, the driver/writer asked me what my connection was. “I know [Smiles],” I responded. I was purposely ambiguous because I myself would like to know the answer to that question. When he asked for clarification, Smiles spoke up and said, “We’re dating.” I was happy to hear him say it publicly for once, but I still didn’t quite know what that meant. At least it was verbalized. He then elaborated as to how long we’ve been dating. He pinpointed it to around the time of the NYC screening of his film. In my mind, I did the math. That was about a month after I met Smiles. Apparently I was one month ahead of him as far as our timelines were concerned. I’d already journeyed out to The Hamptons to see his film once before that night.

The rest of the ride was casual. Smiles even playfully reached his hand down and tickled my crotch. “That’s going to make for an interesting car ride,” I said to him. Smiles sat between myself and one of his friends I’d met twice before. Some in the car were joking about Jersey, and it was interesting to see Smiles defending it now that I’ve given him a more positive opinion about it. I kinda got to know his friend a little better, and I thought he was a good guy. I liked knowing that I could get along well with one of Smiles’ best friends.

When we arrived in the town, we all went out to dinner. It was pleasant, and I met a few new people. Over the course of the meal, somehow it came up that Smiles used to be a dancer. He’d taken classes throughout childhood. This was news to me. Even his good friend didn’t know about it. When I went to make a comment, Smiles jokingly shushed me out of embarrassment. He told me I wasn’t allowed to bring it up again.

We got to the theater and took our seats. Our group was all over the auditorium. Smiles and I were nowhere near anyone else. Before the show started, we cracked a few jokes and made some sexual innuendos about the Nutcracker on the stage curtain. I liked the playfulness I was witnessing in Smiles for once.

The show was far from good, but I had fun with it. I wasn’t expecting a Broadway hit. Smiles was nonplussed.

We got a ride back, and swapped Smiles’ friend for another. When we were getting in the car, Smiles had the friend sit in the middle. I’m significantly taller than anyone in the car, so I wasn’t going to sit in the middle, but the fact that Smiles wasn’t willing to make that sacrifice to sit next to me I found VERY off-putting. I sat next to a stranger, which I’m comfortable with, instead of the man I was dating for an hour-long car ride.

I became the topic of conversation once again. This time it was about my origins. They were surprised to learn I grew up on a farm. “Oh. A farm boy. Better hold onto this one [Smiles],” the driver exclaimed. The rest of the ride home was casual as well. They were kind enough to drop us at my apartment since Smiles was spending the night.

It was late, so we immediately began to get ready for bed. “What’s with you and the purple underwear?” he said. I informed him it was navy. I showed him my one pair of purple underwear and said, “This is purple.” I continued with, “What? Don’t you like it?” He told me he did. He was just surprised I had such colorful underwear. I hardly find navy boxer briefs all that arresting, but I went with it.

We hopped into bed and spooned for a little while we chatted about a few random things. I wasn’t going to see Smiles for some time after that night because of the Christmas break, so there was no way I was making it through the night without getting my answer on where we were. Somehow the topic of chatroulette and manroulette came up. I explained to him how it worked and told him it was how I met the first guy I dated.

As time passed, we turned out the light. We were still snuggling when I finally built up the courage to say, “So where are we?”

“Somewhere between Hoboken and SoHo,” he joked. I responded, “That’s an avoiding answer if I ever heard one.”

After a pause, Smiles said, “I can’t be in a serious relationship right now. When I am, I put a lot of myself into it, and I can’t let myself do that. I need to concentrate on my career right now. But, I really enjoy hanging out with you and spending time with you.”

I took a second to absorb what he just said to me. It wasn’t the answer I was looking for, but it also wasn’t a crushing blow. My response was: “I was pretty much okay with whatever answer you had for that question. I just needed to know where I stood. I would like to continue to move forward, but I’m not in any rush or anything.” He knew I wasn’t thrilled with his answer. I don’t know if it was out of fear I would leave or if he truly was concerned with my feelings on the situation, but he added, “If it becomes a problem, let me know.”

We cuddled some more and went to sleep. I was relieved to finally have the answer. I felt a huge weight lift off my back. I was also horny. I tried to seduce him. “If you keep rubbing me, I’m never going to fall asleep,” he retorted. I quickly quipped, “Maybe that’s what I’m going for.”

I didn’t keep putting up a fight. I knew it was useless. He was stubborn enough that he’d certainly win that battle. I made myself comfortable to sleep and tried not to dwell on the news I’d just received. It was time to sleep. Worrying about what he said would only get in the way of that. Tomorrow was another day…

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Sure. Why the hell not?

I guess I’ve known I was gay for a long time.  But I was in denial.  You see the perfect family all over the media and in real life, and you think to yourself how badly you want that.  You convince yourself that being gay is something you can overcome or ignore.  Then you come to a breaking point.

I don’t exactly know when it is I realized that I was gay.  I can think back to freshmen year in high school and remember being attracted to guys and checking them out in the locker room. I’m sure it goes further back. I never acted on these feelings however.  Not for 26 years.

This is where my story begins.

A friend of mine introduced me to the amazing website chatroulette.com.  I checked it out and found it was quite addictive… Anonymously chatting with strangers around the world. From there, I discovered manroulette.com, and I was hooked. I finally found an outlet to talk to other gay men anonymously and even have a little “fun.”

After weeks on the site I started talking to a guy who lived in New York.  Living in Hoboken, it was interesting to think that this guy was just across the river sitting in his apartment in front of his webcam. We chatted a bit, mostly about how sexy the other looked, and then of course, we jacked off together.  It was hot, and I wanted to keep the “conversation” going.

We exchanged info and started skyping a few nights a week.  I found myself looking forward to our sessions more and more. We started to talk more about our personal lives. Slowly, brick by brick he disassembled the wall I spent the past 26 years building.  Finally I told him my real name and  how close to him I lived.

At this point, he asked, “Why haven’t we met?”

So I questioned myself and thought… Why the hell not!? It’s been 26 years and I’ve been putting on the charade. What do I have to lose? So I made the jump off the cliff and never looked back.

We set up a time for me to meet him outside work, and took a nice stroll back to his apartment. Once there he poured me a glass of wine and we sat on the couch talking for hours. I was so nervous I spilled my red wine.  Luckily, the couch was red as well…

After quite a bit of good conversation, he made his move. It was great. He was an amazing kisser, and I really started to enjoy myself. (Later we would talk about this and he pointed out how he noticed just how much I was enjoying it).

After a passionate make-out session, we took things to the bedroom. Things got heavy and clothes came off, and we truly began to explore each other’s bodies. There was no penetration, but that was ok.  I was just getting my feet wet (and some other things as well).

I spent the night, and in the morning he made me breakfast. We really had a connection and decided that we would definitely see each other again…

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