Posts Tagged late
Late Night Snack
Posted by One Gay at a Time in Gay Dating on April 3, 2012
After my tryst with the Armenian and the Asian, I decided to order some real dinner. This was the last night I was on the company dollar, so I ordered some room service. While I waited, I chatted with the guy who wanted to come by later in the night. I sat and ate my meal in bed with just the TV to keep me company. I was feeling lonely, which is such a strange emotional state to be in considering I’d just shared one of the most intimate acts with two other men.
When midnight arrived, I started texting my late night snack. I asked him what he thought his E.T.A. would be. He told me it was still up the air, but he was definitely coming by. He was out with friends and would swing by on his way home.
Finally, around 2:00am, he texted he was finding parking and would be by shortly. Ten minutes later, I had a knock at the door, for the third time in a matter of hours.
He was a very nice polite black man who was anxious to spend some time with me. He seemed very young and innocent. We chatted a bit while sitting on the bed before any action began. It was getting late, and as rude as this sounds, I was ready to get it in and go to bed. I wanted a nightcap so I could doze off soundly till the morning.
Warning: The following may be too graphic for some. We had A LOT of foreplay and prep before anything happened. He really wanted to cuddle for a long time before we could even get frisky. I was almost ready to call it quits and ask him to leave. It was getting late, and I was getting tired.
There was a lot of kissing. A lot of heavy petting. A lot of licking and sucking. Finally, he was ready and got into position for me to penetrate him. I could tell this wasn’t a guy who gave it up to just anyone. Normally, I’m really into the foreplay and making out, but I’d already had my engine warmed up earlier that evening. In fact, the car had been taken around the block a few times.
I’d saved my climax for him and quickly learned this was a big mistake. He was very bad. We didn’t go for very long because I really wasn’t getting anything out of it. Finally, I stopped and rolled onto my back. I tossed yet another condom in the trash and started taking care of myself. He laid next to me and asked me to finish on his chest. I obliged his request, and he followed suit shortly after.
I knew he was going to be a lingerer. I tried to cut that off at the pass. I humored him for a short bit of time before I finally spoke up and said how I needed to get to bed. It was past 3:00am. It was time for him to go! He got the hint and got dressed. While he did so, he asked if we could hang out again while I was in town. He told me how much he enjoyed himself. I didn’t shoot him down, but I didn’t exactly give him the answer he was looking for. I told him I’d have to see what my schedule allowed for. I told him I was trying to get the most out of my vacation in L.A.
With that, I said goodbye, shut the door, showered all the men of the night away, and climbed into bed to dream about the sunny sandy beach I would be visiting the following day.
Follow @onegayatatimeLet’s Do Lunch
Posted by One Gay at a Time in Gay Dating on March 12, 2012
A few days after my date with Connecticut Cutie, we made plans to grab lunch.
Apparently, he had a very laxed work schedule, and he was able to come down to my neighborhood to meet me for a bite. It was nice to have a lunch date. Most days, I eat my lunch at my desk so I can go to the gym in the afternoon. It’d been some time since my last lunch date was well.
I rearranged my day so I could make this happen. I did not want to cancel on him last minute. Of course right when I was getting ready to walk out the door, people started coming to me with work. I told them I had a meeting to run to, and I snuck out of the office.
He had chosen to meet me at Cafe Rustico. It’s a small pizza place around the corner. Since I was a little late, he went to scope the place out.
When I met him on the corner by my office, he told me he wasn’t thrilled with it and asked if I knew of any good places in the neighborhood we could go. I picked a spot, Lena, and ran it by him. He was fine with it, so we decided on that. We ordered our food, and I picked up the tab. We found a small table to eat and chat. He told me more about his getting locked in the bathroom on the train going home after leaving me from our last date. He was quite a goofball. I loved it.
This time, we spent a lot of time talking about my roommates and his. Mine being my current lot, and his being his parents. Both had their positives, but they also had some big negatives as well. We also talked about our coworkers and bosses and our different situations at work. It was nice learning about his job. Last we spoke, it was left a little vague. However, overall, I think I monopolized most of the conversation.
I was enjoying spending time with him. I wasn’t completely sold on him yet. Only time would tell. But, he was certainly a nice guy and was winning me over slowly. My main hesitation was that maybe he was a little “too gay” for me. I wondered if he’d get along with my friends. My other hesitation was that he was living in Connecticut. How often were we going to be able to see each other?
We talked about what each of us had planned for the weekend. I had nothing special going on, and he was helping his dad remodel their bathroom at home. He joked about his “manly DIY project.”
After we each finished, we made our way to the door. I had to get back to work, and he needed to visit one of his stores and check on the merchandising.
We stood outside the restaurant to say our goodbyes. We exchanged a very nice hug, and then he went in for the big kiss. We pulled back, and he went in again for another, like he just couldn’t get enough. He was a good kisser. I liked it. It was a good sign for him.
I was slightly uncomfortable knowing any one of my coworkers could walk by at any second, but another part of me just didn’t care. Let them see. I’m not hiding anymore. I’m not going to walk around the office broadcasting my sexuality, but I also am not going to hide it.
I walked in the other direction with a smile from ear to ear. It’d been a while since a man kissed me like that. Lately, I’d been the one to initiate. Smiles was never particularly affectionate either.
I was heading to Chicago again for work, and I wanted to see him again before I left. When I got back to my desk, I texted him to thank him for meeting me and told him we’d get together again soon…
Follow @onegayatatimeNot Every Day is Eventful
Posted by One Gay at a Time in Gay Dating on February 6, 2012
After I learned my lesson with cheap haircuts and learned how much more I can spend on top of the original cost to have them fixed, I decided to pay more attention to who was cutting my hair.
The opportunity arose for me to purchase a Living Social for the New York Shaving Company for a haircut, a shave and free shaving cream for $36. I jumped at it because I was about due for a cut. My hair had grown in considerably since Smiles and I had the barber fix it in Brooklyn. The location of this establishment was also an added bonus — Not far from Smiles’ apartment.
I decided to get a new cut before New Year’s Eve, so I made an appointment for Wednesday night following work. I figured I would get cleaned up and then visit Smiles before heading home for the night. We’d texted during the day and I told him of my plan to get a cut and shave and told him I would try to swing by after since I was in the neighborhood.
I have to say, I was really impressed with the place and they did a great job. I was quite uneasy with the cut immediately following because it was so short. It was shorter than the last time, which was a bit of a change for me to get used to. Now I was going even further. It also made me realize the chill outside since I was far less insulated from the bitter cold that night.
As I walked through the streets of SoHo carrying a side table in a large box I’d ordered and shipped to work, I pulled out my cellphone and called Smiles to see if he was home. My hand and face froze in the bitter cold as we I waited for the phone to ring, but I got no answer. After two short rings, it went to voicemail. I knew he’d “sidebarred” me.
However, I was upset for not, because a minute later, he called me back. He apologized for hitting the wrong button when picking up the phone. He was trying to run around to get ready because he was meeting a friend for drinks. I tried to see if he’d be home for another five minutes, even if all I got to do was say hi and give him a kiss, but alas, he was already running late. I was disappointed I wouldn’t get to see him. He did promise to call me later that night before going to bed.
I course corrected for the PATH and made my way back to Hoboken, but not before texting a few other friends to see if they’d meet me for dinner at the Village Pourhouse in Hoboken. I had a Groupon I needed to use up, and it was late. I didn’t want to go home and cook dinner. I also didn’t want to be alone. After not getting to see Smiles, I felt a little lonely.
I quickly stopped home and dropped off the table. I said hello and goodbye to my roommates and made my way to the Pourhouse. D and K decided to come meet me for dinner. It was nice to see them and catch up. I hadn’t seen them in some time.
After dinner, I went home and watched TV. The time came for me to go to bed, but it would be without a phone call from Smiles.
I went to work the next day and learned Smiles was attending the opera that morning from his Facebook status. Considering he took me to the opera a few weeks earlier, I was curious who he was there with. I started to become suspicious, but I had no grounds.
Then I felt quite guilty when he called me during intermission to see if I was available to step away from “work” to grab lunch. I was thrilled. He never did this sort of unplanned thing. I told him it wouldn’t be an issue at all, and we picked a place to meet. It looked like my prayers of him finally asking me on a date were answered.
I decided to take him to Kyo Chon. I’d gone there before on a friendly lunch with a guy I’d met on Grindr and rather enjoyed it. It wasn’t that great this time around. I could tell Smiles wasn’t all that happy with it either. His wings were a little hotter than he could handle. He started sweating in front of me.
After we finished out lunch, Smiles was on the lookout for ice cream. He pulled out his phone to search for it. We walked to a Baskin Robins, but he wasn’t thrilled with the idea. I told him about the Ben & Jerry’s in Macy’s Herald Square, and he was much more content with the idea of that as long as time allowed for me to continue to be away from work.
I took him on a mini tour of Macy’s after we got ice cream to scope out some of the areas. I’d always liked the 1½ floor there. It’s the “designer” floor, and the people there have always taken great care of me, acting almost as a personal shopper. He was turning his nose up at the commercialism of it as if they weren’t “real” designers. I don’t buy all my clothes there, but to me, all I needed was the Ralph Lauren section to keep me happy.
Smiles was talking about his need to revisit his energy specialist, but he was debating whether to go home and go later because he needed a nap. He called to see the hours and learned he’d have to kill an hour somewhere or come back up to midtown later. I invited him to come up to my office to kill time. I wanted to show him our penthouse in the shadow of the Empire State Building, but he had decided on the nap.
I said goodbye to him and he hopped on the subway south.
That night I went out with friends. I thought about Smiles while at the bar and decided to text him, but got no response. I was being a good wingman to a friend that night, so I concentrated my efforts on that.
He texted me back in the am to tell me he stayed in for the night studying. He planned to go shopping for the day, and I didn’t hear from him for the rest of the day. I called him because I wanted to discuss our plans for New Years, but I got no answer. We messaged each other on Facebook briefly that night to tell me he was going out with a friend. I still didn’t know quite what we were going to be doing to close 2011. I didn’t need to know for any reason, but I was curious what was in the plans.
This was another night he’d be going out with his friends and I mine. I started to think about that. He’d never invited me out for his boys’ night out. He never asked about my nights out in Hoboken with my friends. If we were in a relationship, we’d be meeting each other’s friends at this point, but that wasn’t the case. It seems we weren’t in a relationship at all. All the pieces were coming together, but I wouldn’t get the final piece until New Year’s Eve. That would be my gauge on how to proceed. It appeared my timeline had a new distinct end. Or would it be a beginning?
Follow @onegayatatimeLast Minute Regrets
Posted by One Gay at a Time in Gay Dating on December 9, 2011
After my awkward date with Smiles, I felt I needed some change. The date was uncomfortable and the goodbye was lack luster.
Two guys had been reaching out to me on OKCupid, so I took the time to respond to them and try to set up a time to grab drinks. I shot them a text to see if they was available the following evening.
One of them, a guy who happened to go to the same college as me, responded informing me Wednesdays were the only day during the week that really worked for him. He was taking graduate courses, so he was quite busy.
The other guy texted me back to explain he was most likely available to meet for a drink when he finished work, but was unsure when that would be. He is a financial planner, so his hours are somewhat sporadic. We planned to touch base again at 5:00 the next day.
I had a lot of regret after setting up this date, but I tried to proceed with an open mind. All my friends encouraged me to date more people and not put all my eggs in one basket. I was finally following their advice. Smiles wasn’t exactly being the warmest towards me, so no harm, no foul.
When 5:00 arrived, the regret came flooding in. I didn’t want to meet up for drinks. I felt like I was cheating on Smiles. The planner sent me a text explaining he would be working late. He asked if I could meet for coffee at 9:30. I agreed, and sat with my guilt. It was already bothering me, and I didn’t even go out for the drinks yet. What if he tried to kiss me? What if he really liked me? What if I really liked him? This just goes to show you shouldn’t make quick irrational decisions.
As it got later, I got more nervous about the date. Not because of the date, but because of what it would mean for Smiles and I. I didn’t want to betray him. We hadn’t talked about exclusivity yet, but I was hoping we were moving in that direction.
I received a text that calmed my nerves completely. He had to cancel because he got called back into work. I was off the hook. I’m very grateful he cancelled on me, because the guilt would have really gotten to me. It’s just who I am.
I began to examine my relationship with Smiles. There were times he was completely affectionate and a total sweetheart. He really made me happy during those times. Probably far more than he realizes. I really enjoyed spending time with him, no matter what we were doing. On the other hand, when he would ignore me or not take me into consideration, I felt like such a small man. It really hurt to feel he wasn’t feeling about me the same way I was feeling about him. I wanted him to adore me the way I adored him at times. I felt like he always kept me at a safe distance. Not so far that I leave him, but not too close that I could ever hurt him. If we were going to proceed together, he was going to have to make himself more vulnerable and let me in.
I felt like I was part of his second life. He had his friends and acted one way with them, but when he was with me, he was different. He never integrated the two lives. Always separate. This is the reason I broke up with Broadway.
All this also helped me realize I needed Boston back in my life to talk me out of these crazy ideas. He is my sanity. I let my mind run wild after one bad date. He was always someone who could put me back on track and give me a strong dose of reality, not what my mind was conjuring up. However, he isn’t the easiest to get ahold of since he’s in he final year of school.
Smiles wasn’t talking to me much, so I would wait until he felt the need to talk to me. I didn’t go on the date, but I wasn’t exactly running back into Smiles’ arms. I was going to play hard to get a little bit…
Follow @onegayatatimeThe Wedding Roommate Date
Posted by One Gay at a Time in Gay Dating on November 17, 2011
After Smiles left for New York to return the rental car with the two other girls from the screening, I sat around waiting for my roommate to wake up. When I got bored with that, I hopped in the shower, repacked my bags and laid everything out to get ready for the wedding. The night before, I promised her I wouldn’t wake her before 10:30. Obviously, all that didn’t take and hour and a half.
Finally, the time came to wake her. I sat impatiently while she got ready. She suggested we go eat and come back to get ready for the wedding. I agreed. However, when we couldn’t find a place to get brunch for about 45 minutes, we gave up and decided to go back to the house to get ready. We would grab breakfast at the first decent place we passed on the way to the wedding.
I was ready in about 10 minutes and had to wait another 40 minutes until she finished getting ready. WOMEN! This always makes me realize part of the reason why I’m gay! I’m sure my straight male readers can relate to me on this one!
We found a nice place to grab some great coffee and breakfast sandwiches. It was owned by a brother and sister pair far older than I. At one point, while talking to the gentleman in the booth behind us, they started to bicker. I put my head down and began to chuckle to myself. “Excuse me sir! I don’t think this is very funny,” the sister said towards me in a semi-joking tone. Now, I was laughing blatantly. “What’s so funny?” she asked. I explained my relationship with my older sister and how I could easily relate to the brother. I immediately was on her bad side, but I could tell deep down she really liked me — It was all an act. Everyone was eying us up ever since we walked in the door. I was wearing a dapper suit and my roommate had on a hot dress. There was no way to simply blend in now.
We finished our breakfast, we made our way for the door. The sister made a point of making eye contact with me and giving me a dirty look, but the brother also made a point to wish us a pleasant day.
Once we got back on the road, I was reminded once again how bad a driver my roommate is. She was all over the road and scaring the crap out of me. In fact, as we approached a cop on the side of the road, she veered off the road once again.
We got to the hotel and settled in. As we checked in, I noticed a guy in a tux (who I would later find to be the groom) who resembled me. I pointed him out to my roommate and she agreed. When the time came, we made our way to the church. We barely made it in time. We were actually running from the car.
After the wedding, my roommate and I walked downtown to take a few photos and buy some chocolates for my great-aunt. We had a lot of fun.
We made our way back to the hotel to hang out at the bar with my friends from college before we hopped on the bus to the reception. While closing my tab, the uncle of the bride asked me if I was a relative. I was a little perplexed since he was a relative. He should know if I was family. Then I realized there were two families coming together that day. I told him I swam with the bride in college. “Oh. You look a lot like the groom — Like you could be his brother or something,” said this man. I laughed and said I noticed the resemblance as well.
At the wedding reception, I really came to appreciate my roommate. As a gay man, I have limited resources for a wedding date since I wasn’t in a relationship. I planned to go with another female teammate who is still a great friend, but she went and got pregnant on me so she couldn’t travel. I floated the idea to my roommate to be my date months prior, and she jumped on the opportunity. She went to the same college as the bride and I, so I knew she’d fit right in.
I witnessed another friend from college sitting at our table arrive to the wedding and the reception stag. We had quasi dated in college for a very short period. The bride actually tried to set us up. She was the only single person at our table (I’m not exactly sure how you get a table with an uneven number). I felt really bad for her, but I was also very happy I didn’t show up stag myself.
I got myself nice and lubricated with about half a bottle of scotch and had a blast the rest of the night. The only time my roommate and I weren’t on the dance floor was to walk outside so we would stop sweating. Then, we’d make our way right back to the floor. The girl who came alone even came up to my roommate and made a comment about how lucky she was to have such a great wedding date (or so I was told later by my roommate). I had so much fun at this wedding – The most fun I’d had at any wedding I’d been to before. This is all for one reason. I had a great date! It makes all the difference. Who’d have thought taking your roommate to a wedding could be so much fun?
After the reception, we went back to the hotel bar to hang out some more. The problem was, all my friends left, and my roommate and I were exhausted. Half an hour passed, and the bride was nowhere in sight. While we waited, I took the opportunity to text Smiles: “Sooooo much fun! Missing you!” We were ready to give up and go to bed, but not before we raided the cereal bar for a late night snack in our room.
In the morning, we went down for the complimentary breakfast in hopes of seeing the bride again. I learned she wasn’t coming down because they had to get on with their honeymoon plans. I also learned I missed her last night at the bar, had I only stayed a little longer. I also received a text while we ate from Smiles. “Morning! Glad you guys had fun. I wish I could have spent the afternoon out there with you!” It was a very nice sentiment, and it brightened my day a little.
With that, we took coffee to go and got back on the road home…
Follow @onegayatatimeWall Street Dining
Posted by One Gay at a Time in Gay Dating on October 31, 2011
My apologies. After a short hiatus, I’m back…
In the days following my date with Smiles, I was very happy. I felt I finally met a guy I was really interested in who was genuinely interested in me. The possibilities seemed endless.
That being said, we weren’t dating yet — Not even in my warped head. There was no reason why I shouldn’t still be seeing other guys. Before I met Smiles, there were a few guys I was trying to set up dates with while I was building up the roster.
One in particular worked in a different part of town than I worked in. He was down in the financial district on Wall Street working as a consultant. While New York City isn’t exactly long distance dating, I definitely have a predilection for guys who live/work near where I live and work. It just makes it more convenient to see each other.
If you recall, my only real relationship that had two legs to stand on was with Broadway, and we rarely saw each other outside the bedroom based on work schedules. I know myself well enough to know I need a guy who will be around and able to spend time with me.
That being said, this new guy wasn’t eliminated because he was a subway ride away. Like I always say, I’m an equal opportunity dater. I don’t discriminate, even based on location.
We finally found an evening to meet up for dinner after I was done work. When the day arrived, he had quite a busy schedule, but he was still able to step away from the office to grab a quick bite. He picked a restaurant near his office, Plein Sud. It was convenient for me because it was a few blocks away from the World Trade Center PATH station for me to scoot home. I arrived slightly early and waited for him to arrive. He was running a little behind. I didn’t mind because usually I am the one running late.
When he arrived, we went in and sat. It was a nice French restaurant. I was expecting something a little more casual, but I went with it.
We met on OKCupid. He checked out my profile and messaged me. We went back-and-forth a few times before deciding to try to meet up. We had an active lifestyle in common, so I was willing to meet him without first getting to know each other in-depth over the computer. I wanted to make sure we had plenty to talk about on the first date, even if it wasn’t going very well.
We sat and chatted a bit about our jobs. To be honest, I didn’t remember a whole lot about him, but he didn’t recall everything about me either. After discussing what we did to pay the bills, we moved on to where we grew up and where we went to school. He was from Mexico/Texas and still had a thick accent. We had quite a different upbringing and studied very different fields in college. He was a nice enough guy, but we didn’t share all that much in common after all. We talked shortly about what we do for fun before he asked the waiter for the check. Throughout the meal, he kept apologizing for having to make it so quick, but I understood he had to go back to work. There weren’t exactly fireworks between us, so he wasn’t preventing a good thing from continuing.
I can’t know what was going on in his head, but he seemed interested in me and asked if we could meet up again. I told him, “I’m sure we can work something out.” I knew in the back of my head I was never going to see this guy again. He was a nice guy, but I could already tell it would be laborious to find time to get together. Finding friends/lovers shouldn’t be that hard.
I said goodbye to him at the corner as he walked back to work, and I walked to the PATH.
I was okay the date didn’t go spectacularly. I had my sights set on Smiles. However, I know myself well enough, and I still needed a distraction so I wouldn’t smother him with attention. I continued to look to my roster for dates, but that’s also where The Principal came in. We continued to talk on the phone, text and chat. I needed an outlet, and we already had a budding relationship. I would continue to foster things with him while I investigated the furthering of a relationship with Smiles.
Follow @onegayatatimeA Smile That Makes Me Melt
Posted by One Gay at a Time in Gay Dating on October 14, 2011
After meeting Sexy Eyes for coffee, I continued on to my planned date that evening. I picked up a guy on Grindr one morning taking the car service to work. It was complete chance this happened. Normally, my driver takes the Lincoln Tunnel, but because of traffic, he took the Holland. I was particularly bored that morning, so I pulled up Grindr to see what would pop up. Once I was in New York City, I noticed a guy who had a great smile. I messaged him my standard, “Hey stud,” but I also added “Great smile!”
We began chatting a bit after that and he quickly found a spot amongst my favorites. Over the course of a week, we would chat in the evenings. Many times he’d be walking home from being out somewhere and pull up Grindr to pass the time.
He seemed like a very level-headed guy and I enjoyed our chats. We had a few things in common, but our conversations were never very in-depth. In my typical fashion, I asked him to go out for a drink sometime. He graciously obliged. When I asked him for his phone number, instead I got his email. He wasn’t comfortable giving me his number before we met. I assured him I wouldn’t stalk him, and he could trust me. But, I wasn’t going to pressure him into giving it to me.
On a Saturday evening, I sent him an email: “Not to be too forward, but would you have any interest in coffee or brunch tomorrow? Like meeting new people… Pretty chill… No expectations. You just seem, like a cool down to earth guy…” He replied back, “Normally I would say yes, but I actually have a full day tomorrow starting at 10 until late night. Sometime during the week would be better, this is an unusually packed Sunday. ” The response was promising, so I would just have to be patient.
We managed to figure out a time to meet the following Thursday. He picked a bar in the West Village and we agreed to meet at 8:00.
I was running a few minutes late for the date, so I sent him an email telling him I would arrive about five minutes late. I got to the bar at 8:05 and sent another email letting him know I was standing outside with an umbrella and a blue shirt. After twenty minutes and no word from him, my patience was waning. I began to wonder if I was stood up. I texted the guy who cancelled my OKCupid friend date earlier that evening to see if his interview was over and to see if he wanted to hang out since I was still in the city. I was about a minute from walking the block to the PATH to head home. I also had the prospect of meeting Sexy Eyes again that evening in the back of my head.
Just then, a man with an amazing smile emerged from the bar to greet me. I had no idea he was inside this whole time. He apologized for the confusion and told me he could explain. While he was standing at the bar, a man approached him and began chatting with him. All “Smiles” could think of was how much this guy didn’t look like his Grindr pictures (thinking he was talking to me). The guy happened to be there on a match.com date and confused Smiles for his date. After chatting for about ten – fifteen minutes, they realized they were talking to the wrong guy. Smiles hadn’t wanted to be rude while they were talking, so he wasn’t checking his phone. At this point he saw my emails, and he came outside to retrieve me.
I grabbed a drink, and we stood in the corner chatting a bit. The conversation started off VERY rocky. I didn’t know what to say, so I said, “So how was work today?” He replied, “That’s what’s going to break the conversation. Haha. Work was good,” jokingly. The conversation was much easier after that. I learned he was against Grindr in the beginning. His friend encouraged him to download it and use it. His response was, “If I want to take a guy home for a hookup, I can just go to the bar and get one. That way I can see him and feel him up (as he reached out his hand to feel up my chest) before I take him home. Why would I need a digital version of that? That’s not what I’m looking for.” I couldn’t agree more with his sentiments. He told me after begrudgingly downloading the app, he actually had gone on a few dates from Grindr. None were spectacular, but they were adequate enough to keep him on it.
While we were talking, he warned me he had to leave at 9:00 because he had dinner plans with a friend. I wasn’t sure if this was the real deal or if he was using it as an out because he thought the date was going so poorly. “I originally thought an hour would be enough time for us to meet for the first time,” he said. I barely had a chance to meet him, let alone get to know him in the half hour we spent together. I was very disappointed. He was very cute, smart, established, successful, funny, active… Everything I look for in a man. I wanted more.
After we awkwardly closed our tabs, we walked outside. The date ended with an awkward hug, and I said we should definitely try to meet up again sometime soon. He seemed a bit nonplused, but he certainly didn’t shoot me down. I left the date wondering if I made a bad first impression and if there was anything I could do to repair that.
Later that evening around 11:00, I sent him an email stating: “Let me start off by saying your smile pays off even more in person! But anyway… Great meeting you tonight. Hope we can meet up again some time soon…” And in a follow-up email, I sent, “And my number’s ###. Use it.” He seemed to be very good about checking his email, but I wanted his phone number. It offered the option to call. I would get it if he chose to text or call me.
The next afternoon, I heard nothing from Smiles. I wasn’t angry. I was disappointed. I thought I’d give it that one last stitch effort. I sent an email saying, “Or I take it you’re not interested…”
That’s when I finally got a response. “Easy big guy. Good morning. Haven’t had a chance to get into email yet today. Enjoyed meeting you last night, maybe Sunday we can catch up again for a little longer?”
I felt like a fool. I immediately replied, “Sh*t! I knew I jumped the gun! haha Sorry bout that. I should be around Sunday. Hit me up and we’ll figure something out…”
I was elated. Apparently I didn’t make that bad of a first impression after all. He was interested, and now I had something to look forward to. Who knew what Sunday would bring?…
Follow @onegayatatimeRude Can’t Begin to Describe
Posted by One Gay at a Time in Gay Dating on October 10, 2011
When I joined OKCupid, I had high hopes for the site. My ex, Broadway, told me to check it out. I had never heard of it before, but I was certainly willing to give it a shot.
When I joined, I made a profile and began poking around. I was very disappointed with the talent on the site. I found it very hard to find someone I wanted to send a message. I decided to take a passive role. As people viewed my profile and sent me messages, I sorted through the interested men to see if there was mutual interest on my end.
One guy started messaging and seemed to be compatible with me. He wasn’t the best looking guy, but he certainly had something different going for him. I decided to give him a shot. We started chatting on OKCupid, and quickly moved the conversation to the phone. He texted periodically, but mostly, he called at night before going to bed. We sparred playfully quite a bit. Our exchanges were fun, but periodically, he would push the envelope too far, and I would simply shoot him down.
As time passed, I wondered why he continued to call. I learned he wrote a Broadway show to be released in the spring and was contacting some very big names to be the female lead. He was in line for a lot of success, but at the time, he was working out of his apartment and living a below average lifestyle. We talked a little about me and what I do, but we didn’t get much into hobbies and what we do for fun. He was being elusive on those details.
I enjoyed the phone calls and the attention, but every time I hung up the phone, I would say to myself, “Why is he still calling me?” There were a few things we had in common, but I didn’t feel I was really what he was looking for. It seemed he was looking for a guy who would roll over at the snap of his fingers. I certainly wasn’t filling that position. I was actually beginning to look at him as great practice to be more confident and demand more from a man who was interested in me. When the conversation switched to sex, we discovered we were both tops. Even with that knowledge, he took every opportunity to ask me for a picture of my a$shole. I adamantly declined to fulfill that request. I made myself perfectly clear that was not something he would be receiving from me.
When he didn’t drop the request in every phone conversation following, I got quite heated. I told him if that was all he was interested in, he was barking up the wrong tree. I wasn’t on OKCupid to find a guy to have sex with. I was looking for more substance. If that was all the substance he had, he needed to move on. I think he finally got it. But, I also think he thought he was just being playful, and I was overreacting.
It was also getting to the point where I needed to meet this guy. We talked for over a week, and I wasn’t going to invest any more time if he wasn’t worth it. He was already on the fence in my mind — 50/50. But, I was willing to give him a chance, even though the odds were not in his favor.
We planned to go out on Saturday for drinks and a bite to eat to celebrate the casting of his lead female. Over text and phone conversations Saturday morning, I told him I would head into the city and meet him at 6:30. When he responded at 5:15 requesting we do 6:00, I sprang into action to get ready. On the walk to the PATH, I texted and called constantly. He wasn’t responding. I wasn’t about to get on the PATH until I knew where I was going and where I should get off.
I stopped at Starbucks and ordered a latte. Luckily, I grabbed my coat before I left my apartment, because I would be sitting on a park bench outside the PATH station for the next 45 minutes. I continued to call, until finally, he picked up the phone. He shouted, “Geez! I’ll call you back! Give it a rest!”
I was so insulted. No man was going to speak to me that way and get away with it. I was already passing the time by talking to guys on Grindr, and one even went on to invite me out for a beer. I should have abandoned my original plans at that point and had the beer. The fact that he continuously pursued me boosted my ego so much it became the only thing keeping me to those plans. Sad, I know.
Instead of grabbing the beer with the guy on Grindr, I went to The Melting Pot, where my friend is a bartender. I figured I’d grab a glass of wine and give this as$hole a few minutes to get back to me about our plans for that evening. I was going to give him a second chance, but I wasn’t going to let him get away with talking to me like that.
When he finally called, he didn’t acknowledge the time passed since we planned to meet. He also didn’t acknowledge barking at me over the phone. I was very short with him and called him on it. He didn’t apologize. His response: “Well, you can either come buy me a glass of sangria to celebrate my casting, or you can go home and cry about it.” I was flabbergasted! He had some nerve! Now, I was going on this date out of spite. I was going to be spectacular and then shoot him down.
When I arrived, he stood to greet me with a hug. He commented on how attractive I am — better than my pictures — and how he would have put more effort in if he only knew. He was laying it on thick. I could tell he was very attracted to me. I thrived on it. With every word, he gave me more power. He was actually less attractive than his pictures. I wasn’t interested in the slightest, but that doesn’t mean I couldn’t use the date as target practice. I shot him down at every attempt. He made a few lewd comments, and I made my disgust apparent. When he made a cavalier comment about hitting the restrooms as a joke, I went off on him. I asked if that sort of thing normally worked for him. I pointed out how much of a negative effect it had on me. This guy was truly a creep. Ironically, I was having so much fun shooting down a guy who was pursuing me, when I should have been looking forward to the date’s end.
I found out he was late for the date because he was arguing with someone on the phone. He claimed he barked at me not knowing who it was and apologized. If he wasn’t rude enough, he spent 70% of the date texting on the phone. The argument wasn’t over. He didn’t even have the decency to give me his undivided attention.
When the date ended, we began to walk towards his apartment and the PATH train. When we reached a crossroad, he pulled me in for a close hug. Luckily, I didn’t have to kiss him, as he was recovering from a cold. That doesn’t mean he wasn’t trying to pull me closer than is comfortable. He started to make a comment about my being arouse, but I pointed out to him how much that wasn’t the case. I was blunt. “I could not be less aroused right now.” And, after a little more conversation, we parted ways.
I was shocked when he followed up with a text stating his desire to meet again. I responded, “That most likely will not be happening. We have very different priorities, and you were exceptionally rude.” He questioned how he was rude, and I decided it wasn’t even worth my time to recount the scenarios. He truly was an as$hole.
The best part of this was that I walked away unscathed. I actually had fun being blunt yet dignified. I wanted him to want me so badly, so when I shot him down, he’d realize what he was missing. I think I was successful considering the texts continued for some time…
Follow @onegayatatimeFire Island Bartender
Posted by One Gay at a Time in Gay Dating on September 8, 2011
I always get particularly excited when a new guy pops up on Grindr who happens to live in Hoboken. I have pretty much blocked all the gay men in Hoboken, so when a new one pops up, I notice.
One in particular messaged me and was pretty cute. In his pictures, he looked like he had a good body and seemed very nice and genuine. After we chatted a few times, we exchanged numbers and switched things over to texting.
He told me he was a trainer at NYSC, but he was on hiatus while he got a certification. In the meantime, he was working as a bartender on Fire Island. He was gone almost every Thursday through Monday. This made it very hard to find a time to meet up, but eventually we figured it out.
We decided to meet on a Tuesday evening at a Mexican restaurant in Hoboken, Charritos. I had only ever heard good things but had never been. He made a good choice. He spent the day out in the burbs of New Jersey at his friend’s pool, and he was late getting back because of rain and flooding. When he finally showed up in his ripped jeans, finely quaffed hair, tight T-shirt and leather bracelets, I knew this date was doomed from the start.
The night before I was warned about this guy. While talking to N, I learned they knew each other in passing. N had seen him working at the gym and told me he was quite effeminate. I became skeptical but open-minded at that point, but when I met this guy in person, the second he opened his mouth I was turned off. On top of that, I noticed how filled out he was. He was supposed to be a trainer. I would never go to a trainer who was that pudgy and couldn’t follow their own advice.
We sat and had a very nice dinner. We talked about coming out and our families’ reactions to the news. We chatted about work and what we do for fun. The conversation was nice, but there was no spark. He just kept looking at me with this big smile like he wanted to gobble me up. I got the feeling he was a bit lost in the world. He was openly gay, but I’m not sure if he knew how to navigate life with men. I shouldn’t talk, because I have no idea what I’m doing, but he seemed like his GPS was slightly off.
After dinner, he asked if I wanted to grab another drink somewhere. I obliged, but I should have ended the date then and there. I knew better. I clearly wasn’t interested in this guy and had an out to go home, but I felt bad for him. I felt like he needed a friend, so I stuck around. We went around the corner to Sushi Lounge and sat at the bar. We each ordered a round and continued our conversation.
Somehow the topic of the rainbow came up as a symbol for gay culture came up in conversation. I explained just how much I despised the rainbow. He was flabbergasted. He didn’t know how to react. I explained it was not something I embraced. I could understand why some people need a symbol to hold on to, but I was making every attempt to not let my homosexuality separate me from the rest of the world. I am a normal ordinary man who happens to like the company of other men. I don’t need a rainbow to broadcast who I am. On top of that, I find the rainbow aesthetically unpleasing. I could tell I really turned him off by all this, but he wasn’t going to argue.
Then the conversation turned to previous relationships. I told him about the two I had been in and the duration of each. He told me I had a longer relationship than any he’s ever had. When I asked him why, he asked the bartender for another drink. He was a broken gay man. I felt bad for him, but certainly no attraction towards him. I thought maybe I could be his friend.
After we split our tab, I walked him home. Much to my surprise, he invited me up. I have NO idea why I agreed, but I did. We sat on the couch with some wine while we watched one of the music channels. We got into a conversation about Lady Gaga. I told him I found her very inspirational and really got behind her message and what she stood for. He told me he was over her. We obviously were going to but heads, so I was about ready to leave.
At that moment, he took my wine glass, took off my shirt, and started kissing me. He was an awful kisser. All over the place. I did not want to be there making out with him. I did however feel he needed to be kissed. So, I suppose you could call it a pity kiss. After a short while, I told him I needed to go home. I had work the next day, and it was getting late. I said goodnight, and with that I was gone.
I made it as far as the bottom step of his apartment stoop when I realized I left my umbrella in his apartment. There was no way in hell I was coming back to this place to get it, nor did I really want to see him again after that night. So, I rang his apartment. He buzzed me in, and I went back up to get my umbrella. When I walked in the door, he pushed me back into a chair and mounted me. Apparently he wasn’t done. I immediately told him I needed to go. I only came back for the umbrella, not an encore. That’s when I really realized he only wanted me for my body. We didn’t have that great of conversation all night and disagreed a lot. We were obviously not compatible for a relationship, but maybe he was just horny. I was slightly offended and made my way home.
He immediately texted me: “Had a great night with you.” I didn’t respond immediately, but in the morning I texted: “I had a good time too.” After that, I was done with him. I was pleasant, but I didn’t give him hopes of a second date. He would not be a repeat offender. The next day he texted, “How was your day at work?” But, he would not get anything back from me. Once again, it was back to the dating pool…
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 
Lazy Morning
Posted by One Gay at a Time in Gay Dating on February 3, 2012
Today is another Fast Forward Friday!!!
Hope you are enjoying these. It will help bring the blog a little closer to real time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!
Back to your special edition of One Gay At A Time…
Smiles and I had a very special night together sharing dinner in my apartment. We went to be happily in each other’s arms after being away from each other for some time. I’m not entirely sure why, but I felt he’d finally come around to me.
The massage didn’t last long and the seduction failed to the grumbles of Smiles’ stomach. I should have remembered that was his first priority in the morning.
We sat at the kitchen counter and ate while we chatted a bit about what we had to do the rest of the day. I also caught Smiles up on some of the events going on around the world since he didn’t have cable and wasn’t the best at staying informed.
After breakfast, we returned to my room. I needed to get ready for the office, and Smiles needed to get dressed to head home to begin his workday. We started to make out a bit until I pulled him towards the bed. “Do you want to have sex?” he asked. I giggled with a big grin and replied, “Of course. Why do you think I was trying to seduce you before? I always want sex.” That was also my subtle way of letting him know I wanted to have more sex.
Warning: The following may be too graphic for some. I was already on my back with him on top of me, so I could only assume he wanted to top this time around. I topped the last time, so I only thought it fair to receive this time. I slipped the condom on him as he made a comment questioning whether I was doing it right. “[Smiles]. This isn’t my first condom, obviously,” I quipped.
I was getting very close as I pleasured myself while he penetrated me. Just as I was about to climax, he said, “I going to cum.” I quickly responded, “Me too.” And with that, as close as I was, I was a mile away from finishing. In that split second of him distracting me, I lost it. I could feel my muscles quivering just before he said anything, but it was gone. Now, it was top of mind, and I knew it wasn’t going to happen.
Smiles would have been so happy. He’d wanted to make me finish for so long, and he would have been the first to do so from topping me. Alas, it wasn’t meant to be. When it didn’t, I could see him looking into my eyes with compassion. The sex was great. There was no pain or awkwardness. I wanted to show him how much I enjoyed it, but I couldn’t. My mental block got in the way once again.
After we relaxed and kissed a bit, he suggested we clean up in the shower. He was getting ready to hop in, and I told him I was coming in with him. My shower has two shower heads and a seat. Everyone that has seen my shower has made sexual comments about it, and I was going to finally get some use out of them.
I wanted to have some more sensual time together, and when I hopped in, Smiles began to wash me. I was very turned on by this. When he finished, I tried to do the same for him, but he wasn’t interested. He rinsed off and hopped out of the shower to dry off. I watched him as he toweled off, and immediately got extremely aroused. He put lotion on his face with his towel on the floor while I pleasured myself in the shower at the sight. When he left my bathroom, I beckoned him to come back in the shower and help me finish. I wanted him to be a part of it. He climbed in and I pressed myself against his back while I tried to finish. Once again, failure.
When we ran out of hot water, we hopped out. He finished applying lotion and brushing his teeth while I masturbated on my bed. I needed to finish somehow or work was going to be hell for me! He came and joined me in the crook of one my arms while I pleasured myself. FINALLY, it came. I thought of him dropping the towel in the bathroom, and it set me off. I was disappointed it wasn’t a direct reaction to something Smiles did, but I was relieved he was there to witness that it was possible and that my climax was something pretty special 😉 .
We quickly finished getting ready and walked to the PATH with my roommate chatting the whole way. The conversation wasn’t as free-flowing between us as much as when it was just the two of us. I wondered if Smiles had issues with PDA and public discussion. It just felt a little awkward.
When we got to his stop, I gave him a peck on the lips to say goodbye. I thought about that morning all day. I was happy to finally finish with him in the room, but I wished it came at Smiles’ hand. I think it would have been an ego boost for him and a big step forward for the two of us. However, it was progress — Baby steps. This something I was going to conquer, hopefully with Smiles’ assistance.
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