Posts Tagged West Village

Chelsea Lately

Since we saw each other over the weekend, I had tentative plans to see Chelsea again on Monday after work.

I texted him during the day to figure out somewhat of a game plan. When I finished work, I walked to his apartment in Chelsea. He buzzed me in, and greeted me at his apartment door with a kiss. I got caught up on his day a lil’ while we sprawled on the couch a bit. He was in a good mood and was very talkative. After we lounged a bit, we started talking about what we wanted to do for the evening. Between the two of us, we couldn’t really come up with a game plan other than to find drinks and food somewhere.

He finally suggested Sushi Samba. I had never been, but I had their food before. It was amazing. I knew it was a little pricey, but I wasn’t really under a budget these days. As long as he was cool with it, I was game. We walked through the West Village, my favorite neighborhood in the city. We talked as we walked and had great conversation.

We sat at a table on the upper terrace of Sushi Samba since it was an unseasonably nice day, so we decided to order summery, fruity drinks. I ordered a melon drink and he ordered something with passion fruit. Both drinks were excellent, but ironically we enjoyed the other’s drink far more. For the next round we ordered the same, but swapped. We also decided to order a few small appetizers. Everything was great, and I was having a really nice time with Chelsea. We were both relaxed and enjoying the night. It just felt easy. Nothing was forced. I was liking him more and more. He was masculine enough. He was tall, good-looking, a sweetheart… There was little I could find to complain about.

On top of all this, he insisted on picking up the tab when it arrived. No matter how much I protested, he wouldn’t let me split the bill. Finally, I gave up. I was a bit shocked as well, because the tab came to $130 for drinks and apps. We hadn’t even gone to dinner yet — That was next.

One of his friends worked at a Brazilian restaurant nearby, Berimbau, and after trying to get ahold of him, he finally got the address. We made our way three blocks to the restaurant and were seated at a cute, romantic table for two. We decided what to order and both enjoyed our meals. The conversation continued to flow while we ate and even a little under the table leg stroking occurred. I was happy. This guy was turning out to be quite a catch.

While I was rubbing his knee, we started talking about PDA, and I came to learn he wasn’t very big on it. I find myself being a bit shy with PDA as well, but if the right guy gets me out of my shell, I go with it. I’m still building up that comfort level. He, however, did tell me he certainly had no problem with the leg rubbing. He was rather enjoying that, and so was I.

We shared dessert, and I insisted on paying the tab. He didn’t put up a fight.

We walked back to his place. It was a really nice night, and we enjoyed ourselves. Everything felt easy and casual. I liked that a lot. Things were going well, but for some reason, something was still holding me back.

I was pretty tired by the time we arrived back at his place. We hopped into bed and fooled around for a bit. I still had no idea if he was a top or bottom. I wasn’t looking for sex, but I was curious if I could find out the answer. I began to slowly inch my finger toward his bottom until I was “knocking at the door,” but he rather quickly jerked my hand away and stated, “I’m going to have to mentally prepare before that’s going to happen.” I laughed, and we both shrugged it off. That told me he didn’t normally bottom, but he wouldn’t be opposed to it after we got a little more comfortable. After another bit of time, we snuggled up and dozed off.

Once again, we both slept poorly. I was up every five minutes throughout the night. I woke up exhausted. To make matters worse, it was incredibly gloomy and rainy, and he didn’t have to go to work. I did. He sprawled out on the couch in his briefs. He certainly didn’t have a problem stripping down in front of me anymore. He sat there visually teasing me while I got dressed. I came over and joined him on the couch for the little time I had left before I needed to make my way to work. I needed to get a little before I left. The teasing was a little too much for me. I stood, gave him a kiss, gave his package a gentle little squeeze and made my way across town.

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Keeping His Options Open

Well before I met Smiles, I had been chatting with a guy I met on Grindr for some time. He was a feisty one, and I had a hard time locking him down for a date.

One thing you should know about me. If you ever give me your number, count on me having it forever. I don’t delete anyone. Whenever I add someone new from Adam4adam.com, Grindr, Manhunt or OKCupid, I note in their name how I met them. I ask them immediately to send me a pic to attach to the profile so I can keep them straight. If I meet them and don’t think there is potential or I find they aren’t worth my time, I add an X in front of their name so they go to the bottom of my contact list. It’s a system I’ve developed, and it works quite well.

When I broke up with Smiles, I went back through all the guys I hadn’t Xed. It certainly wasn’t a long list, and I’m sure the guys had long forgotten about me. However, it was worth a shot. I had nothing to lose. I’d simply remind them who I was. If they were still interested, great! Mr. Feisty was among this company.

Surprisingly, when I reminded him of who I was, his tone was very different from the last we texted. He was much more open to meeting me and far more playful than three months prior. We got caught up on what was going on over the past three months over text.

I did learn that he met someone in December, and they’d been dating since. However, he was willing to meet up for a drink as friends.

Now, I know he said we’d meet as just friends, but that’s not what he really meant, I’m sure. He was keeping his options open. He wanted to manage my expectations going into our “date,” but he was also leaving himself the opportunity if he liked me to see me again. I was okay with all this and was certainly up for the challenge. My game face was on. Now we were introducing something into the dating game I’d missed from my life since I swam in college — Competition. I could put up a fight with the best of them. I was going to show him how great of a guy I was, and he was going to like it.

He’d been traveling that weekend, and I happened to catch him on his way back into the city in the car from south Jersey. We went back and forth for quite some time. I was once again shocked at the night-and-day difference in his correspondences from the last time we chatted. We figured out a night to grab a drink after work. I went down to meet him in the West Village at Jeffery’s Grocery.

When I arrived, he was wearing a baseball cap and no glasses. This was quite different from the picture he’d sent me. The reason I kept trying to talk to him so much was because the picture was very sexy. I found him very attractive. The man standing before me was attractive, but not like the picture.

We both ordered a beer. He’d chosen one of those odd places that has beers on tap I’d never heard of. I had no idea what color my beer was going to come in. The conversation was tough to break into. He wasn’t being very friendly. If anything, he was being combative. I got the feeling he was being defensive the whole time like he was getting a bad review at work. He never added much to the conversation. He would answer my question fully, but never sparked the next topic of conversation. It was very uncomfortable.

At one point the topic of Facebook came up. He went off! To say he hates it is an understatement. He loathes it, and made it quite known. But, somehow me managed to spare me from being a part of the idiots whining about their lives on there. Somehow I wasn’t one of the, and I wasn’t supposed to be insulted. I respected his opinion of the site, but he didn’t respect mine. He just seemed so angry. I was so turned off and couldn’t wait to leave.

We talked about the dating world. Usually on a date when you start to talk about the physical act of dating, you’ve reached the end. There’s nothing to talk about between you anymore. If you reach this topic, it’s because the only thing you have in common is that you’re doing this with many other people who it didn’t work with either. He told me about a few of his long-term partners. I was jealous he was able to find guys he could call his partner — and more than one. I told him about my worst date ever (until this one), and he couldn’t believe I didn’t leave. He told me he wouldn’t have had the patience to last five minutes with the guy.

However, it was obvious he wasn’t interested in me. That was evidently clear when the bartender asked if we’d like another, and he said he was done. This date wasn’t even entertaining. It was simply painful. I got absolutely nothing out of it beyond the knowledge I wanted nothing to do with this guy.

We paid our tab and left. We were heading in the same direction, so we walked together a block, said our goodbyes, and I walked away never looking back…

 

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You Make Me Smile

Over the next few days, I thought a lot about my relationship with Smiles. It was a constant roller-coaster. As far as relationships go, I am an infant. I’ve had all of five real relationships in my life, including this one. I was still learning how to be in one.

I needed to clear my head. For three days straight, I woke up early to run. It was the perfect way to start my day, I allowed me time to think without really being distracted, and I was able to work towards my spiteful goal of losing my pudge as Smiles so gently pointed out.

It was also beginning to be quite a busy week for me at work. Tuesday I worked until midnight. I talked to Smiles that night when I had a break to make dinner plans with him for the following night. Since I started dating him, I purchased a lot of Groupons for restaurants, so I thought it was time to start using them up. I was eating out at restaurants a lot more than I would have if I weren’t dating Smiles. This was the perfect way to lighten the blow to my wallet. As I left work, I texted, “Dinner tomorrow night maybe? Just leaving work (12:00) :(”

It wasn’t until the morning when I got a response: “Morning! Just getting this. I went to bed early last night. Dinner tonight works.” I explained the Groupon I purchased for Philip Marie in the West Village and asked him if he was okay with the choice. “Sounds good if you get off before 12!” he replied.

Later that Wednesday afternoon, Smiles called to make sure I was still getting out on time, otherwise he was going to grab dinner with some of his friends. I got where he was coming from, but it also felt a little like he was trying to get out of our date. I assured him I would not be working late. As the afternoon progressed, he asked about what time we’d meet, joking about “a blue plate special at 6:30” when I told him I’d be done around 6:30/7:00. We made plans to grab dinner at 7:30. I took the opportunity to slip a joke in there about his grandpa status and his ability to make it until 7:30, and he retorted by saying, “I’m stressed. It makes me sleepy. I’ll bring my cane.”

We sat in the front window of the restaurant, and after we ordered drinks, we dove into conversation. We talked about family and career goals among other things. He talked about his desire to be beyond financially stable so he could spend more time with his family. He is not originally from the Northeast, so spending time with his family isn’t the easiest or most convenient. He also talked about his desire to build an empire. He is very passionate about a lot of different business ventures, many of which are sound ideas. However, sometimes I worry he tries to take too much on his plate at once.

The conversation was great. It was a conversation two people in a relationship would have, not two people who were just dating. I joked with him, “You’re going to be the next Nate Berkus.”

Oooooo, did I get a look! Apparently, Smiles met him in the past, and isn’t the biggest fan of him as a person. “Okay. Note to self: Don’t equate you to Nate Berkus ever again,” I said with a smile.

When the waiter came to ask us about desert, Smiles started a conversation with him like he always does. He asked if we were his only table, and the waiter described his other table. It was a man and a woman who he suspected were on a first date. We joked about our date. While we weren’t on a first date, he was learning all kinds of new things about me, such as my penchant for Black Friday shopping. He took the opportunity to take a few playful jabs at my sanity while we all had a good laugh.

After we paid our bill, we started to walk the five blocks towards the PATH. Instead, we walked about eight blocks. That was about the time Smiles realized we’d gone too far. He questioned the situation, but I explained how I was enjoying the conversation and was willing to walk back up to the PATH if I needed to. We were standing in front of a liquor store while he finished the story he was telling. When he finished, I grabbed his jacket and pulled him in closer so I could kiss him. For the first time, I felt like we were really kissing. We exchanged many affectionate kisses before finally pulling away from each other.

At that point, he said, “Why don’t you live in the city?” I laughed and replied, “Was that a subtle hint? I’m not that far!” And with that, I walked away with a smile from ear to ear. I finally felt like we had moved beyond going on dates with each other. We were dating. We were in a relationship, and I was very happy!

When I got back to Hoboken, I sent a text, “You make me smile 🙂 .” Shortly following he responded, “That’s a good thing cause I ain’t so easy to like all the time!”

I was REALLY HAPPY with everything that night. I was getting the validation I needed. I was also looking forward to Friday. That was the first time I’d be able to see him next since I play volleyball every Thursday. That would also be when I would once again attempt to seduce him and attempt to roll around with him in bed…

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A Lovely Morning

Saturday went by and I didn’t talk to Smiles all that much. I was disappointed about being rejected and was still wondering if it was my own issues preventing us from getting between the sheets.

I sent him dirty text messages (not me in the picture) when I woke up about what I wanted to do to him, and surprisingly, he was responding positively. I couldn’t understand why he would be playful over text, but when push came to shove, I got the cold shoulder.

I wasn’t going to give up on him over this. Sex is important, but it’s certainly not the end all and be all of a relationship for me.

He invited me to come into the city to grab brunch with him and a friend. We made plans to spend a majority of the day together. I was on a mission to seduce him once again. After my chat with Boston, I was ready to broach the subject if I was denied once again.

I decided to resort to one of my old tricks. I started watching porn to get myself excited and raring to go. I thought I could use the material if I got to a place of desperation.

And with that, I hopped on my motorcycle and rode into the city through the Holland Tunnel. I parked on the street and walked up the stairs to his apartment. I brought an extra helmet with me so I could throw Smiles on the back if we were traveling around the city.

He decided we should walk to brunch since it was such a nice day, and we weren’t in a rush. We stopped at Starbucks to grab coffees while we walked. As we made our way to the West Village, we popped into a few stores, from clothing to eyewear stores.

Our destination was a familiar one. Smiles’ friend was meeting us at Extra Virgin. I had no idea who this friend was, but Smiles told me I probably met him previously at his birthday gathering. The three of us arrived at the restaurant around the same time. We all sat at a table in the back corner. Indeed I had been introduced to the friend previously, but we only chatted briefly.

Ironically enough, I couldn’t tell which team this friend played for. It wasn’t until he asked advice about a woman I realized he was heterosexual. There was nothing flamboyant about him, so it was no reflection on him that I couldn’t tell. It was more of a guilt by association thing.

He was a really nice guy, and I was thrilled to be included in the conversation throughout brunch. I am good at diving right in, but when two people in a group of three have a strong long-standing friendship, the third can be marginalized at times. This was not the case. The friend was quite interested in what I do as he works in a similar field of communications.

When brunch was over, we said goodbye to the friend. Smiles and I were on the hunt for a branch of his bank make a deposit. In the meantime, we hit up a few stores and walked around most of SoHo. Smiles was scoping out every bakery we passed along the way. I could tell he wanted something to satiate his sweet tooth. I was egging him on as we walked, but he resisted.

Finally, we made our way back to his apartment. I had been getting calls and emails from work all day. It became necessary for me to go into the office. Luckily, I had the motorcycle in the city with me, so I could shoot up there quickly without issue.

Smiles had plans to meet a friend about a business proposal over coffee, so I told him I would give him a ride on my way to my office. He got changed while I waited, and we were off.

I always like having him on the bike behind me. He’s the first guy to truly embrace the situation. He always inches forward on the seat so he’s right up against me, and he tightly wraps his arms around me. I relish every minute of it. When we stop at a traffic light, I make it a point to rub his leg or grab his hand. I find it romantic ironically enough.

I had to spend about an hour at the office, but the second I was able to leave, I darted back downtown to Smiles’ apartment. He’d already been home from coffee, and I couldn’t wait to be with him again. He really did make me happy. I was also very horny. The porn from the morning worked to get my engine revving, and I was ready to get busy with him. I wanted him in the worst way — Traffic could not move fast enough…

After sitting in tunnel traffic near his apartment, I finally arrived. I rang the bell and climbed the stairs hoping to find a happy ending once I reached the top…

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Postponed Plans

On Thursday afternoon, I made plans with Smiles to go out with him Friday night. We planned to grab dinner and then go out the bars for a night on the town finally. However, that plan would have to be postponed.

Thursday night, he sent me a text explaining he forgot he had dinner plans in Brooklyn and then a birthday gathering in the West Village. He quasi invited me, but added, “That’s probably not exactly what you meant when you said night out on the town,” he added.

I suggested we simply postpone our plans one night. It was still relatively early in our relationship, so some space can sometimes help. I didn’t want him to get tired of me. I would use the time to go out with my friends since I was spending many of my weekends with Smiles or traveling.

Friday, I went out in Hoboken with my friends. He texted me to tell me he got a new phone. I was thrilled to know he was thinking of me even though I wasn’t with him (Or, at least that is what was going through my head as I read it).

Saturday morning, I woke and was feeling very productive. For quite some time, I wanted to trek down to the Financial District to check out the Occupy Wall Street movement in Zuccotti Park. I wanted to take the nice camera from work with me to snap some cool shots of the protestors. I didn’t want to do this alone. It was something Smiles and I discussed many times. I tried texting him and then eventually called him to see if he would join me. He was doing work, so he wouldn’t be able to join me until later in the day.

Since I knew he was by his phone now, I sent him a sexy picture of myself from the summer with the caption, “Wanted you to have a sexy picture for your new phone.” He responded, “Haha. Love it!”

I tried a few of my other friends to see if they’d tag along, including LES. After much convincing, I was able to get him to join me, but under one condition. I had to come by his place to smoke first. I agreed and also proposed we use up my Groupon that was expiring that day.

When I finally got to LES’s place, we smoked and got on our way downtown in a cab. The sun was setting quickly, so I proposed we just grab something quick for lunch instead of using the Groupon.

We got downtown to the Occupy movement, and we began exploring. I took many pictures and was even approached by an editor from The Suit Magazine asking me to send her some of my shots. She was looking for pictures to use in an article.

After we had our fill of protestors, we made our way to Wall Street. While walking, LES said to me, “So what’s the deal with this other guy? How old is he? What does he do?” I knew exactly what that question was. I interpreted it to mean, “What does this guy have that I don’t? What makes him so special.” It was an awkward moment, but it was bound to come up at some point. I really liked Smiles, but I also really enjoyed LES’s friendship. I didn’t want to create too many waves or hurt anyone’s feelings. When we got to Wall Street, we found they were filming Batman, and we wanted to check it out. By the time we got there, they were cleaning up the “set.”

As I was walking LES home, Smiles called. He finished work and was ready for dinner. I wanted to go home, shower, change and drop off the camera before we went out. I told him I would meet him for dinner later, and we made plans. I felt very guilty having that phone call with LES walking next to me.

After I cleaned up and changed, I met Smiles in Chelsea for dinner. We had no location picked out, and ended settling on Elmo for dinner. Conversation during dinner was great. He had a very productive work day, and I feel he let me in even more. He was opening up more and more every time I saw him. We were finally peeling back the layers of that onion.

After dinner, he proposed we go over to Barracuda. I’d never been and have always been leery of it. I’m not a fan of gay bars. They make me uncomfortable.

When we arrived, I learned he knew two of the bartenders. I had met them before as well. They were both very good-looking and pretty unforgettable. They were at Smiles’ birthday gathering. Barracuda wasn’t anything like what I expected. I was expecting a flashy club like seen, not a dive bar. I immediately felt more comfortable.

That is until a tall overly friendly black man came up behind me and started feeling up my chest with his arms around me. He was a feisty one, and I wasn’t interested. I made that pretty clear by my extremely uncomfortable facial expression. Smiles on the other hand was playing ball. I assumed it was a friend of his, until I learned he never met the guy before. This was just Smiles being his charming self.

Because I wasn’t completely comfortable, I drank a little more excessively than I should have. On top of that, Smiles’ ex arrived. I had no problem meeting him and talking to him, but I did have a problem when Smiles said to me, “I hope you don’t mind, but I’m going to steal away with [him] for a minute. I haven’t seen him in a while, and I need to chat about some things.” Based on the interaction, I wasn’t worried that he was going to do something with his ex. I was more annoyed I was being ignored in a place I’d never been before where I wasn’t completely comfortable and knew no one else.

I entertained myself by watching the bartenders cutting off the tall black man because he was being obnoxious to everyone at the bar. However, for me, the drinking continued — In excess! I drank so much, the bartender started giving me free drinks. I drank my face off. I was hurt and p*ssed. This little chat went on for a long time. There was some flirting and maybe Smiles wasn’t 100% over him, but I was okay with that. It’s natural. I wasn’t okay with being ignored! When the conversation ended, Smiles said to me, “How come you’re so quiet?” What the hell was I supposed to say to that? — “I’m quiet because you just ignored me for the past half hour?”

Next thing I know, when I woke up in his bed, the first thing I noticed was I was naked. I never sleep naked. The second thing I noticed was some lube on my backside. I couldn’t for the life of me remember anything about the night before. I don’t remember much after that. I don’t remember getting my coat from coat check. I don’t know how we got back to his apartment. I don’t remember climbing into bed.

I racked my brain to remember anything from the night before. The only thing I could conjure up was a flash of about ten seconds of sex with him on top of me. It was a very scary feeling! I’d blacked out before, but never have I blacked out sex. I was the only one ordering my drinks all night, but I couldn’t 100% rule out the possibility someone roofied one of my drinks.

I never mentioned to Smiles my panicky thoughts. There is no chance in hell Smiles would have done that to me, so I wasn’t worried in that respect. I knew he would never take advantage of me. I was probably pretty lucid in my drunken state, if previous history has anything to say. I was worried I may have done something to embarrass myself. I decided to play it cool and pay close attention to how the rest of the morning progressed…

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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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A Smile That Makes Me Melt

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?…

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San Francisco Comes to The Big Apple

In the week leading up to San Francisco’s arrival in New York, I began to have doubts. I was staying up until 3:00 am most nights to talk to him. Morning runs became a thing of the past, and my waistline showed it. I went on a few dates since I left San Francisco, but none compared to the immediate, strong connection I had with him. I had no replacement, but I doubted my ability to continue a long-distance relationship.

As I drove to the airport I had panicky thoughts. What was I doing!? A man was flying 2,563 miles cross country to see me after spending two shorts days together. Was I ready for this commitment? I wasn’t worried about getting hurt because I was strong and had an open mind about us, but what if I broke his heart?

When he arrived, we shared a long, passionate kiss. We talked on the ride home. When we arrived at my apartment and hopped into bed relatively quickly. This time, I insisted on a condom. I wasn’t making that mistake with him again! I learned my lesson. He too was on the same page about the issue.

After a romp in the sack and quick shower, we traveled into the city. He made plans to meet one of his old friends. Little did I know, but old friend really meant old. He was 50 years old. They were flight attendants together way back in the day. That night, the three of us went to see Sister Act on Broadway.

During intermission, I was chatting with the 50 year-old. He was complaining about the difficulty of deciding if men were gay or straight. He pointed to one particularly sexy man I was eyeing, “Like him. Gay or straight? Who can tell?” At that moment, I looked over the man’s shoulder and noticed he was chatting with someone on Grindr.

I replied, “Gay!” and explained. I was tempted to immediately hop on Grindr and seek him out, but there was no possible way to pull it off while on a cross-country date. However, I still regret not talking to the sexy man.

At dinner following the show, I met yet another old friend — a 40 year-old. I’m a good sport and can hang with ease, but dinner became truly awkward when the discussion turned to age. San Francisco is seven years older than me. His friends pointed out that he’s never been the older man, and then they insisted I call him “daddy” while they filmed it on one a BlackBerry. I adamantly declined.

We met yet another friend at Barbasque. Finally, he was someone in my age bracket and one of the sweetest guys I’ve ever met. He welcomed me right off the bat and chatted me up most of the night.

The next day, we met with yet another old roommate, this time on the Upper West Side. This time a married couple in their 50s whose guest room SF used to live in. The one husband who was home was not very welcoming to my presence. I felt incredibly awkward, and couldn’t wait to exit his apartment.

We wandered the city shopping, and that night, he made plans to meet three friends for dinner. Luckily, everyone at dinner was in their 30s, and the nice guy from the night before was there. So, I spent the night chatting with him while SF caught up with the others.

Throughout dinner, San Francisco had one hand on my leg, and the other on the leg of his best friend from New York. They were being a little more than just friendly. They had a long history, and I don’t get jealous. But, I started to feel a bit jaded.

After dinner, San Francisco, the best friend and I went to a bar. The two of them were tipsy, and the truth finally came out.

I learned he had been going to gay clubs in New York since the age of 19. Not only that, but he was the one known to be carrying K among his circle of friends. I am not anti-drug use, but the picture that was being painted was not something I wanted to hang on my wall.

The ride home that night on the PATH was a quiet one. I could tell it really bothered him that I wasn’t drinking with his friends, but I wasn’t feeling well after dinner. I asked him, “What’s wrong?” but he wouldn’t acknowledge his discontent. I explained my lack of participation was due to feeling ill after dinner, and he became slightly more relaxed.

As we waited for a cab, SF and two drunk “frat guys” exchanged shoulder checks and words. SF is roughly 5’ 5” — no match for these two — but his beer muscles were flexed. I attempted to avoid the situation by coaxing him into the cab. However, he escalated it by rolling down the window shouting back at them and antagonizing them.

He rationalized the situation as protecting me and didn’t stop ranting about how he could have taken them until he finally fell asleep. I was starting to have my feelings affirmed that a relationship between the two of us was not meant to be. I will always defend myself, but antagonizing drunk as$holes is infantile and useless.

The next day, we took my motorcycle out for a spin and spent the day on the pier with one of my friends. When SF left to get ice cream, she asked me how it was going. I explained to her the situation. It was written all over her face — this relationship had ended.

That night, my sister and a few of my friends came over for dinner. I graciously invited all of his friends to join, but all declined. I enjoyed seeing how much my friends accepted him, but at this point, I was completely turned off by his past. That night, we had sex again, but the passion was gone for me.

On his last day in NY, we met one final ex-roommate. While SF was a flight attendant, he lived with a hairdresser in a 1BR apt. Whenever SF was out of town, the hairdresser got the bed, but when SF returned, the hairdresser was relegated to the couch. Meanwhile, he was running a salon out of this 1BR apt. The whole idea was inconceivable to me.

At one point during lunch, between reminiscings of cross dressing and coke lines while watching The Golden Girls, the hairdresser waved his hands at us and bluntly said, “So, what is this?” I was insulted by the tone in which the question was posed, but i wrote him off when I remembered the main purpose of the cross-country excursion was to visit me, not him.

We went home and had one last romp. At this point, I was going through the motions. It wasn’t so much his past that turned me off, as it was that he was hiding it from me.

When I dropped him at the airport, we kissed and said goodbye. SF was the still the sweetest man I ever met, and I truly did enjoy his company. But, I wasn’t completely heartbroken to see him off.

As I walked home after parking the car, I felt alone. I wasn’t sure if it was because he was by my side for the past 72 hours, or it was because I already missed him. Only time would tell.

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