Posts Tagged host

Check That Off the List

Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.

This post is embarrassing. It is now especially embarrassing because a few readers have commented about my promiscuous ways, but nonetheless, I will report the incident honestly and to my best ability. I, in no way shape or form, condone the following behavior. An early warning as well – this post will be graphic.

For some time, I’d been speaking to a few guys on Grindr who happened to be tops. When we both learned we were the same position, discussion turned to other options, such as bringing in a third. We were both really attracted to each other, but neither was willing to bottom for the other.

Many men dream about the threesome. Straight men fantasize about it constantly, and I assume it’s a big gay male fantasy as well. The only difference is gay men probably act on it and achieve it far more often. It certainly isn’t, however, easy to pull off. You have to organize three different mens’ schedules and also take into consideration their taste in other men. We all know how finicky gay men can be.

I woke up Friday with no agenda and morning wood. I wanted to take care of it, but I also wanted to act on my recent fantasy of a threesome. I started with one of the most promising guys who I’d discussed this with before. He wasn’t getting back to me. I began going through more than a few permutations trying to find 2 guys willing to participate who weren’t occupied with work.

Finally, I found one, and we both began to hunt for that elusive third. There were many roadblocks, and lots of waiting to hear back when questions were posed. I thought I had it all worked out, when one of the guys went dark on me. I was very disappointed because I thought I found the perfect combination. One top (me), one bottom, and one vers. When the bottom got a flat tire, it all went to $hit. All this juggling really made me realize why this never happened before.

After much discussion about who could host and who wouldn’t host, I managed to get my original group together, but not without issue. I had to ride my motorcycle into New York City to pick the bottom up. He wasn’t comfortable coming out to Hoboken alone, and the other guy wasn’t willing to host strangers. Strange to think he had no problem hopping into bed with strangers, just as long as it wasn’t his own. I rode in and picked him up. It was slightly awkward, but it all fell right into place. He hopped on the back of the bike, and we rode off to my place.

Warning: The following may be too graphic for some. We arrived before the other guy. I didn’t know the rules, but I was looking to wait for the vers guy to arrive before we got started. The bottom wasn’t so patient. He wasn’t the best looking man in the world, but he had a great body. He started kissing all over me until he undid my pants and started orally pleasuring me. He was quite good. He undid his pants as well and revealed a generous gift. He asked me if we could go to the bedroom until the other guy arrived. I encouraged him to wait since he was only a few blocks away.

When he arrived, the bottom walked to my bedroom and began to undress. I brought the vers guy into my room, and he and I began to undress. I wasn’t as thrilled with him. He looked much better in his pictures, but there certainly wasn’t anything wrong with him. You can’t win ‘em all. I laid on the bed in my boxer briefs while the other two joined me and began rubbing me all over and kissing me. I felt like a king. Everyone was there serving me, and it felt great!

Then the underwear was removed on all parties. There was lots of rubbing, kissing, sucking, etc. After some time, I broke out the condoms and lube. I was horny and ready to get started with the real fun. After using his poppers, the bottom was ready and eager, so I penetrated him while he orally pleasured the vers. Then the vers came to my side of the bed. We’d already discussed I wasn’t bottoming, but he thought I could be persuaded. I told him sorry, but no. I backed off and let him have a turn with the bottom.

This guy was incredibly awkward. He looked like he was having a seizure. His sex was spastic and crazy. On top of that, he was very particular and insisted I use the condoms and lube he brought. While he was inside the bottom, I climbed on top and penetrated the vers. This was not the easiest sex position by any means, and it did not last long. The logistics of three people getting the same rhythm are nearly impossible. It’s obvious in porn when this happens, they are doing it for the camera and certainly not for pleasure.

We swapped positions a few times and had already gone through a substantial amount of condoms. If one thing was certain, I was going to be wrapped up at all times! Finally, I suggested we move things to my shower.

We went through a few permutations of positions in the shower before I told them I simply wanted to watch them while I took care of myself. The bottom protested. I could tell he was very annoyed by the vers and wanted me more. When we ran out of warm water, we all toweled off. The bottom needed to excuse himself. He was feeling light-headed. He made his way out to the living room in his towel.

I was left with the spaz in my room, and I wasn’t thrilled. We tried a go at it for a short bit, but I was much more interested in the guy sitting in the living room. We stopped and moved things out to the living room after closing all the curtains. The bottom was feeling better, so he was eager for me again. He hopped on the chair and asked me to go again with him.

There was something that really turned me on watching the other two guys have sex. I pulled out and encouraged the vers to join in again. I wanted to sit on the couch and finish while I watched them. The bottom wasn’t happy about this because the vers was bad at sex. All three of us were on the couch when I finally finished on my chest. The vers reached climax as well, but the bottom seemed content with stopping before he finished.

The vers guy almost immediately began to get dressed, noting he had to get back home to finish work. The bottom was going to head back in with him so he wouldn’t get lost, but the vers wasn’t willing to wait for him to get dressed. The bottom asked me to ride him back onto the city, but I told him I would give him a ride as far as the PATH. From there on, he was on his own.

We chatted a bit about how spastic the other guy was. Neither of us were thrilled with him, but it is what it is. The bottom got dressed and hopped on the back of my motorcycle. When we got to the PATH, I gave him directions for getting back home.

I sped off home. I was in need of a serious shower. Since the morning’s activities began, I felt incredibly dirty.

If you’re considering a threesome, I strongly encourage you to think it out first. Don’t just jump into it to satisfy some great fantasy you’ve seen many times in porn. If you have the constitution for it, then by all means, do what makes you happy. But, if you’re thinking twice, I strongly suggest you leave the fantasy to your mouse clicking.

There was nothing sexy about what happened. It did not live up to the fantasy I had originally dreamed of. It was awkward and at times laborious. I needed to wash away the shame and guilt I felt, but it was no use. Those would stick around for at least the remainder of the day.

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Welcome Back?

Sorry for the late post… Had a very busy morning at work…

 

Since that fateful night on December 31st, 2011, I’ve had my eye on a certain someone. He was also attending the party I went to on New Year’s Eve.

Throughout the night, I talked to him a fair amount. He seemed like a really nice guy. For a solid twenty minutes, he and I were the only ones in the living room until more guests arrived. We got to know each other fairly well. My original thought on him was he was too young, but the more I got to know him, the more I learned how mature he was. Obviously age had nothing to do with maturity. I learned that the hard way with Smiles. I wasn’t going to rule him out just because he was 22. It also helped he was very attractive. He had both the jock look and the intelligent look about him. It was very sexy.

I didn’t want to jump the gun however. I somewhat embarrassed myself that night, and I wasn’t sure if he took notice. I decided to wait until the dust settled, especially since he knew Smiles though a mutual connection, the party’s host. Before my trip to San Francisco, I laid the groundwork. I informed him of my breakup with Smiles on Facebook. He sent his condolences.

Now that I was home, I was ready to dive in and see if I could ask him out on a date. I sent him a Facebook message that Tuesday: “Hey dude. I know this kinda comes out of left field, but I thought you were a pretty down-to-earth guy when I talked to you on NYE. I was wondering if you’d be interested in grabbing a drink sometime…?” I don’t know why, but I felt very vulnerable doing this. It’s crazy. He’s five years younger than me. Why was I so intimidated? All I could do was wait for an answer.

That night, he finally responded: “I am flattered, but I am kinda seeing someone. Happened right after New Years actually. Doesn’t mean we can’t chill as friends.” My hopes were dashed. I’d been plotting and planning this whole thing out over time to find out I missed the boat. I was kicking myself, but there was nothing I could do. It is what it is.

I needed to graciously respond, and secretly hoped I could meet him as friends, and he would realize how much of a catch I am. Maybe he’d let things fizzle out with the other guy. The door wasn’t closed, even though it was beginning to shut. There was still a glimmer of light — A glimmer of hope.

“All the good ones are… haha… but yes.. Chill as friends works for me too. Always lookin’ for friends as well. Shoot me your #, and maybe we can find a time to hang/grab a drink…” I responded.

Sadly, I wouldn’t hear back from him again. Three weeks later, I tried to see if he would be interested in meeting up, but I got no response. If he was truly interested, he would have responded. I was learning to stop pursuing men who didn’t return an interest in me. It never worked out in my favor, and it just caused me greater frustration. If there were interested, they’d be as excited as I was to message/call/text. It wouldn’t matter about waiting two days before calling. If someone is interested, they won’t care about any of that. They’ll just be thrilled you connected at all.

I was beginning to feel very disappointed and lonely. I had no promising prospects on the horizon. As time goes on, this dating thing is getting harder and harder. Everyone thinks gay dating in New York City is a cinch but far from it. It is so incredibly hard to date in this city. The gay men here certainly don’t do anything to make it any easier.

Warning: The following may be too graphic for some. In the meantime, I was back on local Grindr. I found a guy who lived very close to my apartment who wanted to be dominated and wanted to muscle worship me. I hardly think I’m the muscle worship worthy type, but if that was what he wanted, why not give it to him. I went over to his apartment. He was a bit awkward, but I wasn’t there to find love. I was simply there to satisfy a primal need. I thought I would be able to play the part. I thought I could say all the things a dominant top would say, but in the end, I think I sounded ridiculous. It’s not who I am. It wasn’t awful, but I don’t think either of us were getting out of it what we thought we would. It took me a long time to finish with him, as usual, which didn’t exactly make for a smooth evening. When I did, it was worth his wait. However, because of the nature of my climaxes, he had to run to the kitchen and grab a bottle of Resolve and a paper towel to clean up a spot on the carpet when I overshot his chest.

He came back to the bed and we laid next to each other chatting a bit. I learned he knew the other awkward hookup I had in the same building. Apparently they were friends. I specifically asked him not to mention me, which of course spurred a whole new line of questions. I knew this was going to come back to bite me in the a$s. It was only a matter of time before the 40 year-old started messaging me again.

With that, I got dressed and made my way home on my walk of shame. Luckily it was cold out and it helped me clear my head. What was I doing? This isn’t me. This isn’t what I’m looking for. Why am I doing this? Yes, we all have needs, but I should be putting more energy into finding the right guy instead of Mr. Right Now.

I thought about all the other guys floating around out there on my roster. Was it even worth it to revisit with long-time online friend after our failed date? Maybe the southern boy I was chatting with would finally find the time to meet up. The guy who came back on the roster after almost a year was still a possibility. I needed to plan drinks with him. My Asian neighbor friend from Grindr was still asking me to grab dinner sometime, but he doesn’t drink, so I didn’t see us being very compatible. There was the very sexy, very compatible guy I found on Adam, but he wasn’t responding to any of my messages anymore. I needed to cut him from the list.

I needed to get back in shape and concentrate on building a better me. Ironically enough, I was hitting the gym regularly again. For so unknown reason, I was looking for N there every time I went. I don’t know why, but something inside me wanted to see him there, even though I wanted nothing to do with him. I needed not only to close that chapter, but also to toss the book to someone else and forget about it.

I was spinning my wheels. I was constantly Grindring, and it was getting me nowhere. I was still feeling a little angry for letting Smiles take advantage of me. I thought back to all my relationships and realized how each of them let me down. N, San Francisco, Smiles… I didn’t need any of them anymore. They brought nothing positive to my life. It was time to drop that baggage. The only one I wanted to keep around was Broadway. Since we’ve broken up, we’ve managed to remain friends. I turn to him for advice, and he is always there for me. He’s a good friend and I truly appreciate him. I can’t understand why they all couldn’t be that way. I’m thrilled we’re still friends and want that with all my exs, but if they weren’t going to make that possible, so be it.

I needed to get to a better place. I wasn’t in a dark place, but I was certainly stuck in this constant gray area. I was walking around in a cloud. I was wasting my life away searching for a guy in all the wrong places. If I wasn’t happy, I wasn’t going to find anyone. I just needed to figure out how to change things. It wasn’t going to be easy…

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Goodbye to a Closer Long-Distance Friend

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…

On Friday, my last night in San Francisco, I made plans with Swinging D*ck to come to my hotel. We talked about grabbing dinner before staying in for the night. However, he casually invited me to come out with him and his friends when he realized he had to go out for a friend’s birthday. I was apprehensive since it was a torrential downpour outside. It hadn’t rained for three months prior, but now it was raining for three straight days. This trip was turning out to be an epic fail.

I graciously accepted his invitation and waited for his call to tell me where to meet them. Hours passed, and I didn’t hear from him. I was all dressed up with nowhere to go. I decided to run out to grab dinner at In-and-Out when dinnertime passed by. That’s when I finally got a text. He told me they were going to Lookout in a bit. He would text me when they were leaving, and I could meet them there.

I ate my burger in my hotel room and made my way outside to hail a cab. Luckily I wasn’t out in the rain too long.

When I arrived, I made my way to the second story bar and began looking for him. After two minutes, and noticing a lot of men scoping me out, I found him in the crowd on the other side of the bar. I walked over and said hi with a big hug. He introduced me to his friends. They were all very nice. I wasn’t sure exactly how much they knew about me.

I ordered a beer before I was told we would be moving on for the night. It was back out into the rain. Apparently, we were headed to a house party for the remainder of the night but not before popping into a liquor store for some beer. We hopped in a cab and made our way to the party.

It was slightly awkward because I was now a friend of a friend of the host. I was hoping everyone would be okay with my attendance. Luckily, only the entrance was slightly awkward. After that, I was in my element. I talked with my friend, his friend, and many other men at the party. It was the biggest sausage fest I’d ever been too. I think there may have been two women there versus the fifty gay men.

I met some interesting people and one very sexy man who looked a lot like Steve Pasquale (Sean Garrity) from Rescue Me. Swinging D*ck is a smoker, and when I drink I’ve been known to smoke the occasional cigarette, so those were nice breaks where we somewhat stepped away from the group and could talk more. He really was a sweet, intelligent guy. I learned a lot about him talking to him on Skype, and I only wanted to get to know more.

The night was beginning to draw to a close. For one, I had a flight to catch in the morning. Secondly, the birthday boy/host was ready to hit up the bars. Everyone was getting kicked out. S.D. told me he had to tell me something when we got outside. We walked away from the party to find a bodega to get him cigarettes. As we did, he took the opportunity to confide a big secret he’d been walking around with.

He pointed out to me how standoffish he was the previous night, how he had to leave early and how he changed plans from coming to my hotel that night. Then he told me all this wasn’t because he wasn’t attracted to me — Quite the opposite. The reason was because he was HIV positive.

My heart immediately sank, and not in a selfish way. The compassion I felt for him in that moment was so great, I can’t even begin to explain.

Apparently I know very little about HIV. He told me he’d been “positive undetectable” for a year and a half now. I never heard that term before, but deduced its meaning from its name. I also did the math in my head and realized he contacted it just after he started talking to me on Skype. I put two and two together and realized that’s why he was so depressed when I was talking to him. My heart was breaking for him.

He explained that he is on medication, and the doctor told him he would lead a very normal and full life for the remainder of his time on this planet. I was learning a lot about the treatment for HIV. I realized I needed some education, and I was happy I had someone so amazing to teach me.

A large part of me wanted to cry and give him a big hug because I couldn’t imagine what he was going through all this time since being diagnosed. The larger part of me was upset because he felt he couldn’t just tell me outright from the start.

He didn’t know how to tell me, nor did he want to. He thought I would treat him differently or stop being his friend. I told him he needed to give me more credit than that. He was an amazing guy, and nothing changed between us.

He started to explain his strange behaviors I wasn’t even noticing. When I asked him back to my room, he was very leery because of what might happen, but he still wanted to be with me. So, he agreed. When we were fooling around, he said he was purposely taking more time to please me so I wouldn’t even have a chance to please him. When I went for it, that’s when he really said he had to get going. It wasn’t because he wasn’t attracted to me. It wasn’t because he didn’t like me. “I think you’re amazing,” he added. It was because he was scared. I understood completely.

When I asked him to come to my room a second night, he talked to his friend about it. “I don’t know if I can tell him,” he told his friend. His friend told him to do whatever he felt comfortable with. He actually invited me to come out with them that night in an attempt to set me up with his friend. Looking back, I did feel as if I was being sized up as the night progressed. However, I was not feeling him in the slightest.

When we were at the party, he encouraged me to go with the guys who asked me to come with them for some fun because it would get him off the hook. I wasn’t the slightest bit interested in them either, however their compliments were always welcome. 🙂

I never noticed all this, but I jokingly reprimanded him for going through all those charades instead of just telling me as a friend. Of course I would understand. I told him about all my skeletons. I would have hoped he’d feel comfortable telling me his.

We continued to walk to the bar everyone was heading to. He told me about how he contracted it and how bad the situation was. He admitted that’s why he was so depressed when I first started talking to him. It all made sense now.

When we arrived at the bar, it was time for me to say goodbye. I had an early flight, and it was already two in the morning. We talked a little bit more, gave each other a big hug, and made out a little bit. It was hard saying goodbye. I felt we had so much more to talk about. But I needed to go. We kept coming back for just one more kiss before we finally parted ways.

As I walked towards my hotel searching for a cab, I thought about what just happened. My heart was still breaking for him that he had to go through that. I wish I’d known sooner so I could have been there more for him. I was so proud of him for finally finding the courage to tell me. I was starting to think he just wasn’t into me a little bit, but that’s not important. What is important is that I have a friend I love dearly and will always be there for, no matter what happened to him. I just hope he knows that!

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To Kiss or Be Kissed

Goodbye 2011 and all the hardship that came with it. 2011 was a tough year, and I was ready to kiss it bon voyage.

New Year’s Eve had arrived, and so did Boston. He came to New York City to celebrate with some friends. They were staying at a hotel in Hell’s Kitchen and going to a bar to ring in the new year. We’d been in close contact about meeting up while he was visiting for some time.

We made plans to meet that night before I met Smiles for dinner, however these plans would be broken. As the night’s close grew nearer, Boston realized he wouldn’t have time, so we agreed to try to meet on New Year’s Day.

Instead, I killed time spying on my neighbors across the street with my roommate before venturing into the city for the night. It appeared we’d discovered two ‘mos living over there after some close examination. However, their blinds have been drawn now for quite some time, hindering further “study.”

Smiles and I had been texting about our plan for the evening. We were going to grab dinner somewhere along the way to the party on the Lower East Side, but when he tried to make a reservation for the restaurant downstairs, he realized the difficulty that may pose. Instead he proposed to make beef stroganoff for the two of us at his apartment. I wasn’t thrilled with the idea because I was looking forward to a romantic dinner for two, but it would have to suffice. (Now you can begin to see why I hate New Years).

After we finished eating, we took a cab to the apartment. Smiles spent a good portion of it on the phone with his mother. I’d already made all my new year’s calls on the walk to Smiles’ apartment from the PATH. I didn’t want to be on my phone the rest of the night trying to call people so I got it out of the way before starting our night together. I thought what he was doing was rude. When he hung up, you could cut the tension in the cab with a knife. Neither of us had anything to talk about. The night was not off to a good start.

We arrived at the party and were greeted by a very nice gentleman who was not the host. He was one of the guys Smiles had gone to Six Flags months earlier (whom he didn’t remember without a reminder). A trip I wasn’t invited on and still bitter about. When the host emerged from the shower, Smiles volunteered to run to the corner store to get necessary supplies. Apparently he wasn’t the best of hosts (or so said Smiles). He asked if I wanted to join him or stay and made sure I was okay with staying.

I took the opportunity to get to know the guy who greeted us while I waited for Smiles to return and more guests to arrive. More people joined us in waves, and it was a pleasure to meet them all. I sat on the couch talking to one in particular for some time. He seemed like a really great guy. Later in the night, I would learn from Smiles that this guy told him how great I was after learning we were together. “He had nothing but glowing praises for you,” Smiles divulged.

A majority of the night, Smiles wasn’t paying attention to me. He was far more concerned with standing in as host. He made sure everyone had a full drink at all times, including me. I had to tell him to cool it because I was getting too drunk too fast. I don’t think he realized I was also filling my own drinks besides what he brought me. I was making plenty of conversation with a lot of the other guys at the party in the meantime. Ironically enough, we were talking about dating. I was giving some of the younger guys my “fatherly advice” from my experiences, which is absurd considering I’m out less than two years. I did all this without mentioning my blog once, no matter how much I wanted to direct them to it. Smiles was still unaware I was writing OneGayAtATime.

When the ball was about to drop, the whole crowd gathered around the TV in the host’s bedroom. Smiles asked if I wanted to pile in, but I told him my lack of interest in watching the ball drop. We huddled by the door as Smiles snapped pictures of the group from the doorway. When 2012 arrived, he turned to me and laid a nice kiss on me. When he pulled back, he went in a second time. It was one of his better kisses and it was sweet, but I’m not sure it could make up for the lack of attention I received all night. It was like we were at the same party, but we certainly weren’t together.

As I talked to the other guys, I felt like I was revealing a big secret that Smiles and I were dating. No one knew, and it was as if I was letting the cat out of the bag. I felt uncomfortable about that.

The music came up and the furniture was pushed aside. The living room was now a dance floor. Smiles and I have never gone out dancing together, so I was relishing the opportunity to have a little fun with him. I started dancing with him, and he started laughing at me. It wasn’t completely insulting, but it was also a slightly belittling. I think I was making him uncomfortable (and I am not a bad dancer by any means!).

When I went to refill my drink, Smiles was in the middle of the group dancing up a storm just as I’d seen him bust a move in Central Park. I was hurt. He didn’t want to dance with me, but he did want to dance with everyone else. When I looked down, my cup had only ice in it. So I made the conscious decision to drink away my sorrows. Johnny Walker Black and I huddled in the kitchen and had a good time together.

When someone asked if I wanted to go smoke on the balcony, I jumped at the opportunity. When I got out there, there was a small group including the guy who told Smiles how great I was.

This is where the night gets foggy. There was a guy who was late to the party who was fawning all over me from that point on. He told me I was gorgeous and paid me more compliments than I can remember. I vaguely remember pointing out to him that I was dating Smiles, but that didn’t stop him. He kept laying it on thick.

From that night, the next thing I remember was walking home behind him p*ssed because I was chasing after him. We weren’t walking together. I was walking about ten paces behind him.

Smiles woke me in the morning. I was naked, so I knew we had sex, and I had an uncomfortable moist feeling between my cheeks, so I knew I was the bottom. I thought back and could remember flashes of sex from the night before, but I couldn’t remember anything about leaving the party.

After I searched for my underwear and my dignity, neither of which I could find without assistance, I picked up my phone to check messages. Apparently in my drunken stupor, I wiped out my phone trying to get into it too many times with a failed password. It was back to factory settings.

I told Smiles, and he recounted the walk home. It involved me arguing profusely that we were headed in the wrong direction (Isn’t that ironic). It involved me tapping a French woman on the shoulder and welcoming her to the country. And it involved Smiles being annoyed by my antics.

“And I haven’t even gotten to the fun part yet!” he added.

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Quite a Cast of Characters

Yesterday’s video got great reception, so I decided to include another video I came across lately thanks to Smiles. I think it’s amazing shots and a very emotional piece. On top of it, the music is spectacular! Hope you like it!

On with the story…

Monday came, and I had a very light day at work. I was hoping Smiles would ask me to grab dinner, but alas, nothing. I was always the one to initiate dates, and I needed to see if he would take the initiative for once.

I gave up all hope and went home without hearing from him. Surprisingly, while lounging on the couch in front of the TV, I received an email from Smiles. He wanted to know what I was up to for the night. I logged onto Facebook to chat with him. “They are partying in the streets below me. I’m getting cage crazy,” he typed. I forgot about the Halloween parade that was happening in his neighborhood since I didn’t partake in the Halloween festivities this year.

I responded to him, “What do you propose?” He suggested coming to me since it was so crazy where he lived. I explained I was already home, but I would come back into the city to meet him for dinner. When he learned this, he said, “Oh, no don’t do that. I thought you were still at work.” I suggested he could also come out to Hoboken, which prompted the response, “I’ll get [my friend] and keep myself entertained.” That’s not the response I was looking for. I told him I was bored and really didn’t mind coming back into the city (So much for playing hard-to-get). He told me he felt bad, but I assured him I was as close as I’d be if I were still at work.

We picked a convenient place where we could find each other in the melee of the Halloween parade. We walked around the West Village and found a cute spot to grab dinner, Hudson Corner Cafe. There was a slight wait, so we hit up the bar. Once again, I was a little taken aback by the charisma he showed everyone at the restaurant. From the host to the bar tender to the waitress. He always made it a point to be personal with them, and I found it incredibly sexy.

We ordered drinks outside our comfort zones at the bar until a table was made ready. I wasn’t 100% sure, but I thought he switched the drinks when the bartender served them. Interestingly enough, we tried the drinks the other was served. I didn’t like his, and he wasn’t thrilled with mine. When we sat at the table, we ordered another round, and the waitress clarified the confusion. It worked out well considering we liked the other’s drink better.

We ordered our food and chatted while we waited. I was surprised the conversation was flowing so  easily since I’d just seen Smiles the day before. When the food arrived, he commented on how little food I received. We split a brussel sprout salad, and he encouraged me to take a much larger portion. It was a very sweet gesture. We talked a lot about work and his aspirations. I was being very encouraging, but I also gave him my strong opinion on the situation. He was trying to find a typical office job while struggling to reinvigorate and old company he started years earlier. I knew that was his passion, and he would be very unhappy with a desk job. I told him he was at a great advantage. He didn’t have a comfortable job he wasn’t thrilled with that he was stuck with because it was a paycheck. He had the freedom to do whatever he wanted. He should just take a job to have a job. He took my advice to heart, which I really appreciated.

After dinner, we walked the streets. We passed someone in an amazing E.T. costume like I’d never seen before. We decided to grab desert at Magnolia’s Bakery before more walking. I made friends with a few British pigs in a blanket while waiting in line. We ate as we walked, and when we finished, we were near the PATH station. He asked, “What do you want to do now?” I was under the impression he was dropping me off, but that wasn’t the case. I didn’t think very quickly, but I suggested we head over to the parade and check it out.

Smiles had his camera, so we snapped a lot of pictures of some special characters along the way. We finally arrived at the parade and watched for a short while. When we had our fill, we continued on. Smiles suggested we go into a bar. This sounded like a great idea to me considering I already thought our night was going to end a while ago.

When we walked into the bar, Julius’, Smiles needed to use the facilities, so I attempted to order us drinks. For some reason I had no luck with this task. Usually this is my forte since I’m 6′ 2″. While standing there, an old man was creepily eyeing me up. He wasn’t being nonchalant about it at all. His eyes were burning a hole in me. I made NO eye contact with him, even though he was standing two feet away from me. When Smiles returned, he magically had no problem getting service. He commented I wasn’t smiling, and that’s why I wasn’t getting service. (Probably cause I felt uncomfortable).

We drank our beers and had a chat about weight. I joked about the Magnolia’s stop and the beer and how it would affect my waist. He casually made a comment about my weight. This wasn’t the first time he alluded to my size. Over the summer, I was extremely confident about my body, but once fall arrived, I put on a few pounds. By no means was I fat, but I wasn’t as sexy as I was over the summer. I asked him,”What’s your waist size?” He told me and was shocked to learn mine, 32″, was only one inch larger than his. He couldn’t believe it. I wanted to point out to him we share similar body shapes, even though I think he thought I was heftier. I made a lot of jokes about losing weight not for him, but in spite of him. I was making it a serious goal to lose weight just to prove it to Smiles I could. He looked at me with skepticism. I still couldn’t believe he was basically calling me fat, even if it was playful.

After we finished our beers, we continued to a bar he frequented, Diablo Royale. He knew the bartender quite well. We found a nice corner to stand in and chat. We took in all the costumes around the room. I remember specifically realizing I didn’t feel 100% comfortable with Smiles yet. I questioned this. We’d been dating for some time, and while I enjoyed his company, I felt I couldn’t completely relax. It was as if I was on a constant audition.

When we had our fill of the night, he walked me to the waterfront. Even more than usual, there was quite a cast of characters walking around. He pointed out a piece or property he’s had his eye on for some time he’d like to develop. I agreed with him about the possibilities for the property. That night, he was opening up to me more about work. I liked learning about that side of his life. I shared a lot of the passions he had in that respect. Finally, he walked me back to the PATH. It was 12:30, and I knew I would be heading home. This was one time I wasn’t hoping/expecting to go home with him. I had to work the next day. I was still shocked and very pleasantly surprised the date didn’t end after dinner. He gave me a kiss, and I hopped on the PATH.

He was quite sweet and affectionate that night, but we still hadn’t completely clicked. Something was still missing, and I couldn’t quite put my finger on it…

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Smiles Returns pt. 2

My second date with Smiles was off to a great start! We already walked the entire High Line and grabbed sangria. Now we were on our way to an unplanned dinner.

As we walked, he reached down to grab my hand. I’m terrible at making those first moves, so when he did, I nearly melted into a puddle right there on the street. I loved every second of it. It also gave me the validation he was enjoying my company. We stopped to snap a few pictures of interesting things along the way. I was happy to see he was into photography since this was something I was truly interested in as well. We chatted more on the subject as we walked and stroked each other’s hands.

When we arrived at Extra Virgin, I learned why he warned me he was quite the regular. Immediately, the host made a killing fuss over him. He was a tall flamboyantly gay black man who had no qualms about jumping all over Smiles in front of me. I enjoyed the spectacle, especially since Smiles was getting quite embarrassed by the fiasco.

We took our seat at the bar and began to peruse the drink menu. Dark and Stormies have become one of my new favorite drinks, especially in a crisp fall day. The bartender asked Smiles what he wanted to drink, and much to my surprise, he replied, “I’ll have a Dark and Stormy.” Of course, when he turned to me, I replied, “I’ll have the same.” We commented to each other how much we like he drink and how perfect it is for this time of year. It was nice to see more and more commonality as the evening progressed.

As I was looking over the menu, I settled on the chicken with a mushroom sauce. He was looking over his menu and made the recommendation,  “The chicken is excellent.” I informed him I already decided on that and was looking forward to it. Once our orders were placed, we could return to our conversation. We found more and more commonality between us, and I was really enjoying the time I was spending with him. What was supposed to simply be coffee and a stroll on the High Line turned into an all day affair.

Shortly after we arrived, a coworker arrived and sat next to Smiles. We didn’t acknowledge each other, and I was okay with that. I wasn’t hiding anything, but I’m still not out at work. It made for some slight awkwardness, but it certainly didn’t taint my evening.

Our meals arrived, and we both enjoyed them thoroughly as the conversation continued. At one point, he stood to use the restroom. As he passed my chair, he put his arms around me from behind and gave me a hug. It was one of the sweetest things any man had done to me in a long time. When he returned, he sat with his hand on my thigh as we chatted. The bartender brought over the desert menu since the host offered it to us on the house. I then took my hand an placed it on his thigh, gently stroking his knee while we chatted. At one point, I removed my hand, and he reached up to the bar and placed my hand back on his leg. I liked his conviction and it sent a clear signal to me he was enjoying his night as much as I was.

Following our meal, we walked down the street. He again reached out and grabbed my hand. While walking down a darker street, he guided me across the sidewalk, pulled me in closer, and he planted a kiss on me. These are the little things that really win me over. I was really falling for this guy, which was very interesting since the first date didn’t go extremely well. We came upon a cellist on the street corner playing for all passersby. He took the hand he as holding and pulled it around his back. We stood and listened for a song while he played. It was very relaxing having him leaning against me with my arm around him. I was truly there in the moment and extremely happy. I’m sure I had a smile from ear to ear.

When we decided to continue on, we walked toward the PATH station. We made one quick pitstop in a sex shop on Christopher Street. We looked in the front window at some of the wares the store sold. I wondered if this was a test to see if I could roll with the punches and have fun. I think he wanted to see how I would react, and I performed superbly. We had so much fun talking about everything in the store. He even took pictures of a few things, and we had a good laugh.

We continued another block before we were at the PATH station. We stood facing each other talking about how much fun we had. We hugged, and I pulled him in for a few kisses. I wanted to ravage him, but it was neither the time or the place. We had a conversation earlier in the night about making people a priority and seeing the people you care about the most. I acknowledged that conversation by turning to him as he walked away and said, “Let’s do this again soon! Make me a priority.”

After the date, I shot him an email the following day. “So I tried not to jump the gun so much this time… Waited ’til I had some downtime this afternoon to hit you up… Better?? Hope the cold calling isn’t too painful! (Acknowledging his workday) Had a great time yesterday! Hope you negotiated good rates with everyone (the cellist, bartender, host, Joan Rivers, …) to play their parts. Would love to see you again, so let me know when you’re free, and we can get together. P.S. Do you think I’m I phone number worthy yet?”

Shortly after, he replied, “LOL! yes, ###.###.####. Glad you appreciate my unplanned dating Karma ;-)” It was great to hear back from him so soon. It showed he was still interested in seeing me. I couldn’t have been happier. It was just a question of when I would get to see him again…

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