Posts Tagged disappointment
Technical Difficulties
Posted by One Gay at a Time in Gay Dating on October 16, 2012
On the night of July 3rd, CK and I slept at his apartment. I had a beach bag packed to head to Fire Island the following day. I insisted if we were going to trek all the way out there, we needed to leave early in the morning to get a full day of it. We also decided to make an effort to come back to the city in time to view the fireworks from his rooftop. We made plans with one of my old roommates and his girlfriend. They were going to join us on his roof since he had such spectacular views of the Hudson River.
When we woke, the weather didn’t look like it was going to be the most cooperative. We checked the report, and there was a threat of thunderstorms all day long. We both agreed to nix the idea of going to the beach and decided to stay local instead. We lounged around his apartment all morning, watching TV and eating a light breakfast, all the while waiting for the rain. When lunch time rolled around, I was anxious to get out of the apartment. It still hadn’t rained, and it was shaping up to be a pretty beautiful day. While we both agreed we could have gone to the beach, we also agreed not going was nice too.
Recently, I broached the subject with him of spending habits. I realized I was spending a lot more money, especially going out to dinner. I proposed a plan to try to cook more and go out less. I didn’t want to keep spending money frivolously, and thought he was probably in the same boat. The topic was well received, and we agreed to make and effort to spend less money.
As we walked to lunch, we made a plan to grab something small and cheap. We ran a few of CK’s errands before finding a spot to grab lunch — Uncle Nick’s, a Greek restaurant in HK. This was not part of the plan. Everything was a bit more expensive than a $5 sandwich. CK reminded me of our frugal conversation, and pointed out this place was not part of the plan. However, since all the portions were larger, I pointed out that this could serve as our dinner as well. We could take the leftovers home and eat them before the fireworks. It would work out nicely since we ate such a late lunch.
This worked out perfectly. We did swing by the grocery store to grab a few snacks for his rooftop to supplement our lunch/dinner. We grabbed chips, humus, cookies and supplies to make sangria. Before digging into making sangria, we decided to check out the scene on the roof. We wanted to know what we were getting ourselves into. CK lived in a large apartment building, and the roof certainly wasn’t going to hold all the residents, especially if they were bringing guests like me. Much to our surprise, it was still fairly sparse, but we knew that wouldn’t last long.
We quickly went downstairs to gather our things so we could lay claim to a prime fireworks viewing spot. As we made sangria, I reached out to two friends who were to be joining us, but they weren’t going to be able to make it. Looked like it was just going to be the two of us. That, and his roommate and the harem of friends he gathered for the night.
We made it back upstairs in time to lay out a blanket and enjoy a drink as the sun set. I was enjoying some quality time with my man before the crowd showed up. After some time, he had to run back downstairs. Of course, he disappeared for quite some time. I was sitting there alone trying to fend for our spot as more and more people arrived. Slowly but surely, his roommate and his friends started showing up. Of course, they assumed we were holding a spot for them, so I was surrounded by them on the blanket — Still no CK. This was not how I wanted to spend the night.
Finally, he came back. By then, the roof was fairly full. Shortly after, the fireworks began. Well, at least I think the fireworks began. CK’s roommate assured us the building had a prime view of the fireworks. He informed us he’d watched them from the roof the year before. LIES! All lies! We couldn’t see the fireworks at all. Immediately, there was both a mass movement forward toward the river to get a better view and a mass exodus out of the building to head to the river. CK and I tried to maneuver the roof to gain a better vantage point. When I turned around, he wasn’t following me.
In the chaos, I wasn’t able to find him again. I looked all over, standing on planters to see over the crowd. I tried calling him, but he wasn’t answering. I assumed he went downstairs, and to be honest, I was pissed. I assumed he abandoned me in an attempt to better view the fireworks. The elevators were overrun with people. I descended the twenty-five floors until I reached the ground floor. Because I didn’t have a building access card, I was a bit trapped. My only option was to walk back up to the top floor. I tried calling and calling, but still, CK was not picking up. When I got back to the roof, I managed to find CK. I explained what happened, and he explained how he was unable to find me. I was disappointed because the romantic night I was hoping for had gone to sh*t. This would be yet another fourth of disappointment. We had a fun day together, and I really enjoyed it. But, I wanted romantic fireworks with my man for our first Fourth of July together.
When the crowd thinned out, we managed to find a decent vantage point. Of course, we got b*tched out by a girl, who after investigation we learned was not a resident of the building. Although our night wasn’t quite as romantic as it could have been, another couple was having an incredibly romantic night. A man was proposing to his girlfriend via a presentation on his iPad. It was very touching and made me realize the night was a success just being with CK. I needed to stop thinking about the perfect picture I had in my head and just go with it.
When the fireworks ended, we made our way down to his apartment. The alcohol was flowing, among other things, and all his “roommates” were already home causing a raucous. When we moved into CK’s bedroom to escape the party a bit, it slowly but surely moved into the room as well. I wasn’t thrilled. Slowly but surely, they piled in, one by one. I inched my way further and further up the bed until I was sufficiently pressed against the wall to make room for more “roommates.”
That’s when it happened. I was so incredibly disappointed. CK and I discussed in detail how uncomfortable certain situations made me, and he breached that comfort level quite drastically. I wanted to be anywhere but there. I wanted to go home. I completely shut down. He made me so incredibly minuscule by ignoring the entire lengthy conversation we’d shared about this very subject. I wasn’t exactly being forthcoming about what made me so upset. The fact that he was so clueless about why I was so upset only made it worse. He actually thought I had cheated on him and didn’t know how to tell him. He couldn’t have been further off base.
I just wanted to leave, but I knew there was no way I would be able to make it home before the sun rose in the sky with all the crowds. Luckily, everyone began to file out of the room naturally. I laid there with my back to CK crying myself to sleep. He tried to comfort me and made excuses, but it was no use. The damage was done. He knew how I felt about this, and he selfishly did what he wanted anyway. This was not how someone treats you when they love you.
My head was spinning. Because I was worried I would have to let him go, the tears streamed more and more. I’d reached the last straw. I wasn’t ready to talk about it that night because I wanted a clear head when we talked about it for the last time. That night, we’d have to go to bed with tension in the air.
Spring Break Flake
Posted by One Gay at a Time in Gay Dating on May 9, 2012
This is my 300th post! You guys have been amazing! Here’s to many more to come!
I was particularly excited about my staycation because I was going to get to see Boston again. We made very tentative plans for him to come down for at least part of the week because he was on spring break from school.
As we got closer to the visit, Boston went dark on me. It was pretty standard for him to not return my calls. The only time I ever got to chat with him live was when I called on a Friday night when he was pregaming before hitting the scene. I understood he was very busy. It was his final year in school, and he had a lot going on. On top of classes, he was searching for an internship. He was even looking at a few places in New York City. I was very excited at the prospect of him being nearby, but I wasn’t getting ahead of myself.
I was more than annoyed this time because I was expecting him to visit or to have me swing up to Boston. I had to use the time off. I thought it would be a good time to try to see him. I’m sure he is reading this right now ready to kill me. He probably thinks this is a bit of a guilt trip, and it is. But, it is also part of the bigger picture for my week off. I made no plans because I thought I had some plans. Granted, even if I didn’t have those plans with Boston, I probably would have been doing the same thing — Lounging on the pier, going to the gym and having sex.
In early March, I tried to see if he was still coming to visit. “Gaah. Haven’t even thought about it yet. I’ve been drowning in work. I’ll know by next Wednesday though. That’s when midterms are over.” After that, complete darkness. I didn’t hear from him for a few weeks. I angrily texted him from the pier one day, “You could just text me back you don’t want to/can’t come…” After my vacation had come and gone, he finally texted me back: “Just got my phone back today. Lost it over St. Patty’s Day weekend. Will call you later tonight. You gonna be around?” Of course I would never receive that phone call. I did understand though. He was in college. I tried to put myself in his shoes, and I realized I wouldn’t have come down to visit either, however, I would have told him I wasn’t coming.
After time passed, I playfully texted, “As much as you suck for bailing on me, ‘A$$ Grab’ is not gay. He just showed up to the bar with a girl.” Surprisingly, he quickly responded, “Means nothing. And I didn’t bail on you!” I wasn’t going to let him get away with that. “Um. Yes you did. Just sayin’,” I added. He was quick to note, “We never had plans and this break hasn’t been conducive to going to NYC and back.” I pointed out our tentative plans and his lack of communication in his inability to come. I also pointed out that even though he lost his phone, there are other ways to reach out to me. I also expressed my disappointment in not getting to see him. It was something I was really looking forward to. He responded back saying, “Alright. I’m sorry. Been in Vermont all weekend and all break I’ve just been busy working, so I’ve been flustered a bit.”
Again, I understood, and I fully forgave him. I wasn’t going to hold a grudge for that. Time off when you’re as busy as he is can be precious time. I kept myself busy taking admiring guys on the pier in the sun in Hoboken as you see in this post.
I depend on him more than I should. The problem is I don’t have any gay friends. When I have something I want to share, I feel like I’m putting some of my friends out by talking to them about it. They just can’t relate, and I’m sure they’re tired of hearing it from me. I turn to him because I know he’ll give me sound advice, but also because I have no one else. This post may come across like I’m bitter, but that’s not the case. I truly appreciate Boston and everything he’s done for me. He’s a good guy.
We still good friends, and he still ignores my phone calls. But, I’m sure all that will change when he’s finally graduated and eventually moves down to New York. Or at least I can hope, right?
Follow @onegayatatimeIs This Going to Become a Trend?
Posted by One Gay at a Time in Gay Dating on March 29, 2012
Once again I had a Friday off from work, and once again I found my libido taking over my ability to reason. I woke up that morning feeling frisky, and of course I pulled up Grindr to see who was around.
I went through a lot of guys and even started acting like all the other guys I hate on Grindr. I was skipping the pleasantries and getting right to the point. I knew I needed to find a guy who was simply looking for one thing. I didn’t want a guy who would linger or keep calling. I just wanted my libido satisfied.
I finally found a guy who seemed to be interested. He was a black man who had an amazing body. When I gave him my proposition, he surprisingly responded with a reasonable response. He didn’t normally seek out hookups, but he understood the periodic need to satiate the animal within. He wasn’t completely comfortable with just coming to my apartment and jumping into bed. He wanted to meet me in person first. I learned we both went to NYSC, so we agreed to meet at the gym and take things from there.
I get no service when I’m at the gym since it’s completely underground. I texted him just before entering “the cave” telling him what I was wearing and that I’d arrived. I worked out for nearly an hour, and he hadn’t made an appearance. I assumed he stood me up. I actually walked upstairs until I got service to exchange a few texts with him. He was on his way. I informed him I was nearly done my workout. I guess my libido was slowly fading with the endorphins of working out.
I was doing my last circuit of abs before I was ready to head out when I finally saw him emerge from the locker room. He came right over to the mat. I smiled as he approached, and he laid down next to me. He started doing sit-ups at a rapid pace — So much so that his shirt began to lift and expose his abs and the tiny shorts that barely covered him, exposing a majority of his jock strap. It certainly wasn’t anything I’d attend the gym wearing, but I could tell he was a bit of an exhibitionist.
The whole time, I waited for him to get my attention and say something, but he never did. After a few sets, he got up and walked away. I assumed he wasn’t interested. Apparently, I’d just been rejected without a word. It was quite a blow to the ego. Maybe I needed to stay at the gym a little longer.
I made my way into the locker room to change when I discovered him getting undressed right next to my locker. He was standing there in his jock strap putting his clothes into his locker when he stepped back and removed the jock as well. He was quite the “gifted” man. Of course I was sneaking a peek every chance I got. It’d been a while since I’d seen someone so “gifted” in person. It was very difficult to hide my own excitement in my gym shorts. I needed to leave before I got really excited and someone took notice.
He grabbed a towel and made his way towards the showers. It was just the tease I needed to get my engine revving again. Looks like it was going to be the computer and me when I got home.
As I left, I texted him declaring my disappointment at his lack of interest. He responded back almost immediately, “Did you leave?” I explained to him I was done my workout and thought he wasn’t interested, so I was heading home. He told me he was definitely interested, and he just didn’t want to interrupt my rhythm. He told me he’d be over in a short bit.
When he arrived, we sat on my bed chatting a bit. He was a freelance journalist over in New Jersey covering the Whitney Houston funeral. He seemed like a really intelligent down-to-earth guy. It made the hookup a little more relaxed and less transactional.
Warning: The following may be too graphic for some. Things started to get hot and heavy, and we both found ourselves naked enjoying each other’s embrace. After a short while, I took out a condom and some lube while he relaxed on his back. We were going at it for a little while when I accidentally slipped out of him. I wasn’t the only thing to fall out however. I sincerely hope my face didn’t show what was going through my mind at the time. This wasn’t as bad as the guy in San Francisco, but it certainly wasn’t pleasant. There was a pea-sized nugget laying on my sheets at the base of his behind. If this was going to keep happening, I was going to learn to be celibate.
I quickly improvised and suggested we continue our activities in the shower. We had some fun in there until we returned to the bed. I did my best to avoid the nugget while we both tried to finish ourselves off. Finally, I climaxed (I’m amazed I was able to with everything going on around me).
He informed me it would be a long time before he was able to finish himself. Apparently, he had similar issues to my own. I was happy in the realization my symptoms were finally lessening, and I was able to relax and finish more readily.
He got dressed, and I said goodbye to him. About ten minutes later, after immediately throwing my sheets into the washing machine, I received a text from him. He’d left a bracelet behind — And it was very important to him.
DAMNIT! I was going to have to see him again. I told him I’d bring it into the city sometime, but he suggested he would collect it over the weekend the next time we were both heading to the gym.
In the end, we needed to plan an evening for him to swing by and pick it up, but this time I told him, “No sex.” He stopped by for all of thirty seconds while I handed it to him through the door, never to be seen again.
Follow @onegayatatimeIt’s About Time
Posted by One Gay at a Time in Gay Dating on February 27, 2012
Today is a Fast Forward Monday!!!
My apologies to those who have come to expect Fast Forward Fridays. I have been traveling for work/pleasure, and I got caught up in things. I haven’t had a chance to write the second post, so I’m making up for it today. 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…
After missing the opportunity to finally meet my online friend after almost a years time chasing each other around, the day finally arrived when I was scheduled to finally meet him in the flesh. This was well overdue, and I was quite excited. I wasn’t about to get ahead of myself, but the suspense had been building up for quite some time.
We discussed where we would go for drinks or dinner and finally settled on Charritos, a Mexican restaurant I’ve been to on numerous occasions. In fact, this wasn’t the first date I took there. We planned to meet at 7:30. I knew the place didn’t take reservations, but it was a Monday night on a holiday weekend. I figured everyone was home getting ready for the coming workweek. It also wasn’t the nicest night, as snow was in the forecast, so I thought we’d be alright.
When I arrived, I was immediately proved wrong. I stood in front waiting for him to arrive noticing every table (all 8 of them) filled with diners. Finally, he arrived, and we attempted to go inside out of the cold. Even this proved difficult since there was nowhere to go once we were in there. While we waited for a table to clear, we awkwardly chatted.
This was surprisingly difficult. He seemed so incredibly flirty online and charismatic, and the man standing in front of me was a very shy reserved individual. I couldn’t get over it. Where was the guy I’d been chatting about my body and sexual interests in detail? Where was the flirt?
We talked about work and the weather. It was a struggle to find a topic to discuss. Everything felt forced. It wasn’t awful, but it certainly wasn’t what I expected.
Finally we got a table and sat. After we ordered, we started to chat a bit more. I asked most of the questions. He always responded in detail, but he never asked a question in turn. That may have helped the conversation flow much more freely, but it wasn’t there. I had to volunteer all my information. I feel awkward talking about myself when I wasn’t asked to. It was as if I was interviewing him for a job.
One topic we got on was siblings. I don’t know why, but that topic has been coming up more and more frequently on my dates. I’ve actually noticed it and tried curbing it. I learned about his siblings as well. It was nice to hear he came from such a similar family dynamic.
We talked about his job as well. I was very intrigued by it. He told me all about his schooling, his specialty in the field relevant to the gay community, his boss, the clinical work he does… This was really shaping up to be quite the catch of a man. He was very sweet and thoughtful. However, our chemistry was not mixing AT ALL! It was so disappointing. On paper he looked so good. Online, he seemed a sexual match for my libido. In person, he was a mouse. Night and day from my expectations.
After quite a while, the waiter basically asked us to leave. There were people waiting for a table, so they kicked us out. I was more than a little p*ssed, because I thought it was very unprofessional and rude, however, it was time for the date to conclude.
We’d already talked about him coming over to my apartment before the date. I was still very sexually attracted to him. I wondered if he’d relax when he was out of the public eye. As we walked outside, I asked him where he parked and told him I’d walk him to his car. I was hoping for a signal along the way to show his interest. I thought he’d drive me to my apartment and come up.
When we got to the car, it was the complete opposite. I hope you can understand my explanation without a diagram:
I thought we’d at least say a proper goodbye. I was hoping for a kiss considering all I could think about during the meal was how good his lips would feel. When we got to the car, I stood on the sidewalk, and he walked to the front passengers panel in front of the rearview mirror. That would have been fine. I may have even used the car as a backboard for a strong kiss, BUT there was also a chopped off parking meter between him and myself. Yes. A metal pole about four feet tall was between the two of us. I don’t think he could have strategically showed his lack of interest any more other than to simply get in the car and drive away.
We said goodbye, and I told him it was nice meeting him. He said, “Likewise.” That’s when I grew some balls and took what I wanted. I moved forward, reached my long arm over the pole, hooked it under his arm around his back, and pulled him in for a kiss. It wasn’t a long kiss or a makeout session, but I certainly wasn’t going to be satisfied with a peck.
And with that, I turned and walked home in the flurries falling from the sky. I was still a little blown away by the lack of spark during the date. I wasn’t even ready to go home. I decided to stop by my friends’ place on the way home and say hi.
I came in and we caught up on what’s going on with each other before I told he and his wife about my awkward date. He was a little baffled by it as well. He couldn’t understand what was going on. He really loved the parking meter pole story as well. I was so nonplussed.
I sulked home after saying goodnight to my friends. When I got home, I was curious to see if he was back on a4a. Surprise! I was right. I wasn’t going to get past this immediately. I needed to ask him about what happened.
“Surprise, surprise. Look who’s on here,” I messaged him. We chatted a bit awkwardly about the date. He messaged me back: “I was waiting for you to ask me to come back.” He wanted to come back to my apartment. He even brought his c*ck ring and poppers with him. I was so confused, and I made that clear to him. He wasn’t aware of his mixed signals, nor was he aware of the pole. He just thought I wasn’t interested since I walked him to his car. It was all a big misunderstanding. “I had a good time. I thought the conversation was nice,” he added. That doesn’t make up for the awkward date however. That just cleared up the mixed signals at its close.
Just to satiate my curiosity, I told him we would have to try to fix what went wrong when I got back from my work trip to San Francisco. He agreed, so we kept in touch over the next week.
I decided to see what was going on with the southern guy. He texted me to see how my weekend was, so I picked up the phone and called him. Again, we talked for almost an hour while I packed. This completely made up for my awkward date. I was really looking forward to getting back so I could finally meet him. Hopefully this one wouldn’t be as big a disappointment.
In the morning, I had a message from my new southern gentleman caller. He was asking for a picture of my “morning excitement” we’d discussed previously. I denied his request and told him he’d have to wait to see the real thing. This was my way of getting him on the ball about meeting up with me.
I also got a text message from my friend and recent neighbor. It was very sweet of him to do so. I needed to make it a priority to hang out with him when I got back to New York.
All that would have to wait on the backburner… The following day, I was headed to San Francisco for the week for work. Waiting for me were two men. One I attempted a long distance relationship with whom I would meet for a cocktail. The other, a great confident and online friend whom I was extremely excited to meet in person, especially in the bedroom…
Follow @onegayatatimePut Me In Coach
Posted by One Gay at a Time in Gay Dating on February 13, 2012
It was obvious things were strained between Smiles and I. For quite some time, our relationship was on the decline. He was distant, closed off, and not very engaged, and I wasn’t happy.
I tried to stick it out with him. I tried being patient and understanding. He was a good guy, and I could see there was a great guy under all this. But, I had reached my limit. I knew I deserved better. It was time to move on.
Wednesday passed without communication from Smiles, so I sent him a text in the middle of the afternoon. “It’s apparent you’re trying to put distance between us. Can you possibly find time to discuss things with me in person? Thanks,” I typed.
He responded ten minutes later with: “I can this weekend. I’m up at 5:30 and in bed at 12:30 and not a lot of time in between. This weekend will be a littler better but not much. I will make something work though.”
Wow! It was all I could do to restrain myself from responding, “Thanks for squeezing me in!” How could he!? After three months of dating, he couldn’t sacrifice a gym session to take the time to talk to me like a man. What a coward! It was completely disrespectful and painted a clear picture of Smiles’ true feeling for me. I doubt he ever truly cared for me. He simply enjoyed not being lonely.
I’m no one’s lap dog. I was back in the game. In my mind, we were all but broken up. It was inevitable. There was no coming back from this, especially since the relationship wasn’t the strongest to begin with. I’d been through yet another failed relationship with a man who simply wasn’t that into me. My confidence was pretty much shot. What was it about me they couldn’t seem to embrace? I’m not pathetic enough to say what was I doing wrong, but I also knew I may be something to turn these men off.
Regardless, I was back in the game. I needed to put myself back out there. Some people would argue I needed some time to be single and to figure myself out, but I know myself well enough. I didn’t need time to heal from this one. I did need to have some fun. It’d been a long time since I had passionate active sex, and I was hungry for it.
After my last breakup, I went wild over the summer. I hooked up with a lot of guys and expanded my sexual horizons. It was both a good thing and a bad thing. I didn’t want to go back to my old ways. I already learned how unfulfilling it was. There was no need to repeat old mistakes. But I wasn’t going to completely limit myself. I was “single” for all intents and purposes.
I had been talking to a Latino on Grindr for a bit of time. He seemed like a really nice guy, and we had a lot in common. Latinos aren’t really my type, but I’m an equal opportunity dater. N was of Latino background, and we got along well enough in the beginning.
We set a date for Thursday night to grab a drink at a local Hoboken bar, Trinity. He lived in neighboring Jersey City, and I convinced him to drive over since I didn’t have a car — It was a bit cold for the motorcycle.
He arrived before me, and found a spot in the corner of the bar. It was a good spot since we could talk without a large crowd of spectators. I shook his hand and introduced myself. He did the same, and I immediately recognized an accent of some sort. I asked him where he is from.
He told me of his roots in Venezuela and asked about my upbringing. I told him about my time growing up on the farm and how I came to live in the shadow of New York City.
We’d learned about our shared interest in volleyball and talked about that for some time. He was much more of an amateur than myself, but it was nice to find someone who had an interest in it.
We somehow got on the subject of coming out and families. He told me he’d been out of the closet since he was eighteen. He asked when I came out, and I proudly told him I was fresh and new. I told him I’d only come out about a year and a half ago. The expression of shock and disappointment on his face said it all. I knew the date was a failure. We chatted a bit about it, and I could tell he was not thrilled with the idea of my being a “new gay.” I tried to explain to him I wasn’t new. On the timeline, it may seem short, but I did a lot in that short period of time. I grew in leaps and bounds and had relationships of all sorts with varied men. For the first time in my life, I was trying to vaguely paint myself as a recovering whore.
When I think back about this, it was a dumb idea. If it was something that bothered him, I should have accepted that and moved on. I didn’t need to end the date then and there, but I shouldn’t have tried so hard so early to be what he wanted. I should have just been myself. This may be why I get involved with men that aren’t truly interested in me.
Somehow our discussion morphed into the topic of sex with women. He’d never been with a woman, but I have. I was just adding water to the fire with every sentence. We talked about the local gay dating ring, Grindr and the like. It was an interesting conversation, as we the entire date, but I doubted there would be a second.
When we finished that drink, I paid the bill and offered to walk him to his car. When we got there, I went in for a kiss. It was pretty bad. We pretty much crashed into each other with a forceful peck. I’m not sure why I kissed him if I wasn’t all that interested in him. I think it’s because I’ve been out of the game for some time, and I just felt like it was what I was supposed to do.
As I walked home, I checked my phone to find out one of the guys I’d met from Grindr months ago was moving to Hoboken. We’d been in touch sporadically since we originally met. He was just coming off a really rough breakup, and I was just starting things off with Smiles. I met him in hopes of making a new gay friend. I needed those as much as I needed lovers. He’d invited me to go out a few times, but I was never able to due to other plans. Now we’d be neighbors, and hanging out would be much easier. I was just what I needed to come back into my life at that moment.
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Posted by One Gay at a Time in Gay Dating on January 19, 2012
When I got home from my dinner date with Smiles, I sent him a text asking if I could spend the following night with him at his place. I wasn’t sure if he’d already passed out, but I never got a response. I was hoping he’d answer me before I left for work in the morning so I knew if I should bring clothes for work the next day.
My office party was that Wednesday night at the Greenwich Village Country Club. We weren’t able to bring guests, but I was hoping I could see Smiles following the party. I wasn’t all that into it and was willing to leave early if need be.
Wednesday morning arrived, and I still had no answer. I decided to be on the safe side and bring clothes regardless. Maybe he’d answer me midday. When I didn’t get an answer, I asked the question again in a text.
He responded with an apology. He didn’t realize he didn’t respond the night before. “Yes. You can spend the night.” I explained the party, and he told me he had happy hour plans with his wealthy client friend and his partner.
For me, the office party was not all fun. Every year I get wrangled in to help with a few elements of the night. I performed my duties and then had fun drinking and dancing with my coworkers. It was a really good time — Better than I expected. However, I was more looking forward to seeing Smiles.
I texted him to see what he was up to. If he was still out, I was going to meet up with him. He told me he was wrapping up drinks and heading home shortly. I told him I would be leaving the party shortly as well and would come by.
I said my goodbyes and collected my coat. I wasn’t that far from his apartment, so I decided to walk. While I walked, I called his phone just to make sure he was home. I called about 10 times in a row with no answer. I sent text messages and heard nothing back as well. I wasn’t sure what to do, but I decided to continue on to his place. Finally, just as I was nearing his block, he picked up. His phone was on silent in the other room, but he was home.
He buzzed me in, and I came upstairs. I gave him a big kiss hello. I wasn’t drunk, but I was properly tipsy.
We talked about happy hour and the party while we hopped into bed. I undressed and hopped on “my side” of the bed, and he slid into his side.
Just recently, I made the switch back to briefs periodically. I decided I looked good in them since they showed off my legs — The same legs Smiles loved to compliment. So I knew what I was doing when I laid on my back in just briefs while talking to him. We chatted a bit before he made a big move. My seduction worked.
Warning: The following may be too graphic for some… As I laid on my back in my briefs, he started groping my crotch as he rolled over partially on top of me to make out. This was a bit out of character for Smiles, but I like it. Apparently he liked what he saw and went for it. I could get used to that.
Things got more heated and passionate and the clothes came off. I thought this was going to be the extent of our romp in the sheets, but apparently he was ready to escalate things. He proposed sex. I was a little apprehensive because he was still recovering from surgery. I didn’t want to further injure him. He detailed his limitations; he couldn’t top and he couldn’t put his legs up. I was still worried I may hurt him, but if he was good for it, I was game.
With that, he put a condom on me, and he climbed on top. It didn’t take long before I lost it. I’d been drinking the better portion of the night, and that really wasn’t helping at the moment. “I always lose you in this position,” he said. I found that ironic, because that was the position Broadway and I so often found ourselves in.
“Have you ever done poppers? he asked. I told him I’d never done them myself, but I’d witnessed them used. He told me it increased blood-flow and would produce one of two effects. Either it would make the problem worse or it would solve it. I figured it was worth a shot, so I agreed to partake.
He opened his nightstand drawer and pulled out a small vial. He held it up to my nose as I inhaled. Sadly, it had a negative effect.
“Let’s try one more thing. Stand up. It may help the circulation,” he told me. So I did what I was told. Magically, it worked. He turned, and I pressed my chest against his back. He lubed me up and bent over the bed, and we went at it. Finally, we were having great sex, even if it did get off to a rocky start. Apparently, he also was enjoying it as he finished on the floor. Just as he did, he turned around and said, “I wish I could make you cum.”
And it was over… I was close to finishing, but him pointing that out to me made me lose it immediately. My mind switched over immediately.
He walked to the shower, and I laid in the bed. I wanted to hop in the shower, but that wasn’t physically possible based on his setup. I thought we could have more fun and maybe I would finish. When he came back, I took off his towel and pulled him into the bed. I told him not to say things like that because it was a sure fire way to make sure I didn’t finish with him.
We cuddled for a bit, just laying in each others’ arms. Just as he was about to get up to go brush his teeth, I asked him if I could ask another question. I wanted to ask him where we stood. I wanted to know what I was to him. However, as he walked away, he responded, “No.”
I was a little crushed. I went from being so happy to finally be having great sex to utter disappointment. How was I supposed to be in a relationship with him if I couldn’t express how I was feeling.
He came back, and I was already prepped for bed. I curled up facing the wall ready for sleep. I wanted him to read my body language and realize how much I closed off, but I don’t know if he got the hint.
That night I had a dream about Smiles. I specifically remember him in the dream saying to me, “You know I like you, right?” It was the reassurance I wanted in reality, but this was a figment of my imagination. It was just that – A dream.
For the rest of the night, I didn’t sleep well. I tossed and turned like the inner turmoil I so wanted to release.
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Posted by One Gay at a Time in Gay Dating on November 14, 2011
Before I met Smiles, I was chatting with a guy on OKCupid. After cruising the site, trying to find anything remotely resembling a prospective man, I managed to find a guy who was both attractive and seemed to have a great personality — at least based on his profile. He looked like he led an active lifestyle and was smiling in all of his pictures, so I sent him a message.
Surprisingly, he messaged me back shortly thereafter asking me to email him some pictures (my profile only has my torso pic). However, he added, “And just to be upfront about intentions, I’m seeing someone currently, but I’m so down to make legit guy friends. I don’t do well with the fem/gay scene so I’m always eager to meet more guys like us :)”
I wasn’t exactly thrilled, but I was also looking for friends. At the least, maybe I could get a wingman out of him. I responded, “Of course you’re seeing someone… All the good ones are!!! I can use friends just as much as I can use lovers ;)”
He seemed like a very genuine, down-to-earth guy. I was pleasantly surprised by his response. “Awww! Well you’re very cute. Why are you single?” he asked. We exchanged numbers and planned a time to meet on Thursday night immediately following work. Ironically enough, it was a night I double booked.
When my day was winding down, I texted him to confirm, but, he had to cancel. He had an impromptu second interview for a job, so I couldn’t exactly hold it against him for the last minute cancellation. Instead, I called up Sexy Eyes to see if he could grab coffee and already had plans later to meet Smiles for the first time.
I tried to reschedule with my new prospective friend, but I got no response after that. I wasn’t sure what happened exactly, but enough time passed that I lost interest. Then, out of the blue, I received a message, “Hey man, I broke up with my boyfriend So I’ve been in a funk. Sorry for flaking on you – I’m not usually like that, but the breakup wasn’t exactly amicable. If you want to give me a second chance, I’ve evened out and am down to chill.”
If you’ve ever read my blog, you know I’m all about second chances. However, now the roles were flipped. I was dating Smiles for a few weeks at this point, so this time I was the one looking for just friendship. For some odd reason, I didn’t make it a point to lay that out for him ahead of time, as he had done before the first time we planned to meet.
Wednesday after work, we met at Shima in the East Village, his neighborhood, for sushi. He was already waiting at the restaurant when I arrived. I sat and we immediately jumped into conversation. It was great because there was no tension or awkwardness. We jumped right in like we were old college buddies. I learned a lot about him over dinner — How he just moved to the city, what he wanted to do, what he did for fun, his family… The conversation flowed constantly. We really hit it off.
When dinner ended, we stood outside chatting a bit before he invited me back to his place to smoke and watch Archer, a show we found we shared a common love for.
The whole reason I went on this date was because my friends all encouraged me to date other people. They explained it was healthy to date a few people at the same time until you find one you really like. Things had become a but of a roller-coaster with Smiles emotionally. It went against every fiber of my being, but I decided to follow their advice. However, when push came to shove, I turned it into a friend date and couldn’t make a move. It was getting late, so after a full episode, I decided it was time for me to head home. I wanted to leave before things got awkward.
He may have thought we were on a date, but I was dating Smiles. And, as much as my friends told me I needed to be dating other people as well, I couldn’t do it. I couldn’t lead my new friend on while I had a strong interest in Smiles.
He walked me to the elevator to say goodbye. I could tell he was expecting a kiss. And, I can’t lie. I wanted to kiss him. I had a really good time, but like I said, I couldn’t lead him on like that. I knew where my true interests lay. I gave him a hug and said goodbye. I could see the disappointment in the expression on his face as he walked back into his apartment. I felt awful.
I knew I couldn’t leave things as they ended. I wanted a friendship from him, so I wanted him to know he didn’t just get rejected by me. I decided to text him to explain on my walk home.
I told him how great he is and how much I enjoyed myself with him, but I explained how I’d been dating Smiles since the night he first cancelled on me. He responded by noting, “Guess that was my loss.” We discussed it further. I realized I was wrong in not telling him my intentions going in to the date, but I didn’t know my intentions until the date was closing. I thought I could date more than one guy at a time, but it’s just not how I operate — At least not when I’d been seeing the guy for a few weeks. I could tell he wasn’t thrilled with the situation, but I had a feeling time would fix it, and we could start a great friendship.
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