Posts Tagged Boston
Deep Pockets
Posted by One Gay at a Time in Gay Dating on February 16, 2012
Since deciding to end things with Smiles, I’d already been on one date and had one hookup. I certainly hit the ground running. I felt slightly guilty all this was going on before we even had the chance to formally end things, but then again, things never really formally began between us.
I wasn’t wasting any time either. I had been talking to a really nice guy on adam4adam.com and set up a date to grab drinks with him after work Friday evening. It was a bit awkward because this was truly a blind date.
He had two pictures on a4a, but neither was clear and one didn’t include a face. When I asked him to send me a better face picture, he told me he didn’t like taking pictures of himself. Of course a red flag raised in my mind, but I had nothing to lose either. If I arrived and the guy was unacceptable, I was right next to the Port Authority bus terminal. I would be home in no time with little of my time wasted.
We agreed to grab drinks at Arriba Arriba in Hell’s Kitchen. It was conveniently located between his apartment and my office, and like I said, it wasn’t far from my transportation hub to go home.
As I left my office and began walking north, I was quite nervous. I’d never been on a true blind date before. I’d at least seen pictures of their faces, but this time I had no idea what he looked like. I joked with him, “Not gonna lie. Not sure what you look like… Haha.” It didn’t take him to respond: “Sorry mate. Don’t like taking pictures of myself. We will find each other… haha. You can ask me to leave once you see me and how ugly I am. Lol.” I didn’t care all that much at this point for the picture. I was already going in blind. I replied, “No apologies needed. Just tellin’ ya you’re gonna have to find me…”
I waited for him on the street corner. I put that time in a good location to good use. I surfed Grindr in HK for any new prospects. I know some may say that is classless considering I was waiting for a date, but I’m not in HK all that often anymore, and there is more talent in that neighborhood than where I work. He finally arrived and approached me. I asked how his trek to HK was, and we went inside to find a table.
When we learned we could only stand at the bar since we weren’t ordering food, we decided to go elsewhere. I was at a bit of a loss because I hadn’t been in the neighborhood for some time. I didn’t know of a good place for us to go for a drink. Luckily, this guy was good on his feet. He suggested Eatery, and we were off.
We grabbed a seat at the bar and ordered a few rounds of drinks. We chatted for a long time about a myriad of things. The whole time, he kept his ball-cap on. Beyond the fact that he should know it’s bad manners, especially since he was an older gentleman, I was also worried there may be no hair under there. I’m not shallow, and looks are not everything to me. But, if he was balding without shaving his head, I wasn’t sure I could deal with that. (Smiles shaved his head and I was obviously okay with that).
We talked about our upbringings. He lived a bicoastal lifestyle, living in California and South Carolina. He also was shipped off to boarding school in Switzerland, where his grandparents lived. I grew up on a farm and went to public school. We had quite the education/socio-economic divide before. This is one thing I‘m not sure I am capable of getting past. I’m sure if it was the right guy, I could handle him coming from wealth, but it’s something that makes me quite uneasy. He came from money, and a lot of it.
I also learned he leads a very lavish lifestyle. He told me about his plans to purchase a house in Barcelona. He’d recently traveled there to scope out some places. He also told me about the $200,000.00 loan he gave a friend and was never paid back because the friend died and left his only possession, his apartment, to someone else. He told me about his lavish trips to the Caribbean islands recently. The list goes on.
Ironically enough, he wasn’t talking about all these because he was trying to impress me (Or at least it didn’t come off that way, which is fine). It simply came up in conversation or I coaxed them out with questions. I just felt uncomfortable with our socio-economic differences. I don’t really aspire to the position of kept man. I want someone who will share the financial burdens with me equally. I know a lot of people would love to find someone rich to marry, but money means very little to me when it comes to love. I think like I would constantly feel like less of a man if I had everything provided for me constantly, and I contributed far less to the relationship. Maybe this is something I will learn to get over in time, but for now, it makes me uneasy.
I learned how he continued to build his wealth and his professional relationship with a family in Canada. He told me about all the businesses he was involved in, and I started to worry he was another Smiles — Too much on his plate to commit to a real relationship. I also learned he wasn’t out to many people in his life, even after he’d been in a nine-year relationship with a man who left his wife for him. It ended when the man cheated on him while he was away on business. I wasn’t sure how I felt about him still being in the closet. He’d experienced too much and was far too old to still be in denial of his true self. I wasn’t sure I wanted a “project” at that age.
Drinks quickly turned into dinner. We stayed at the bar and made friends with the waitress. She was super sweet and very interested in chatting with us. Over our meal, we conversed more, and I learned we share a lot of the same morals and interests. We had similar outlooks in life.
He also became much more physical as the night progressed. He constantly had his hand on my leg rubbing my thighs and caressing the back of my knee. I started to do the same. Periodically, he would stand and give me a big ol’ bear hug. It was sweet. I liked knowing he was a passionate physical man. I needed that after Smiles constant distance.
Six hours later, we were ready to leave the bar. He decided to walk me to the bus. I thought when we exited the restaurant we’d exchange a kiss and go our separate ways. He was a true gentleman and walked me to the Port Authority. Not only that, but he walked me to my gate to wait for my bus and stood there waiting with me. It was midnight, and he was being a total sweetheart. He stood anxiously next to me as if he didn’t know what to do or how to close the date. He wasn’t really out, so I had a feeling a goodnight kiss in front of a large group of strangers was out of the question. When my bus arrived, he said goodbye and we agreed to be in touch.
As I rode home from the date, I wasn’t entirely sure what I thought of him. He became more attractive as the night went on, but I wasn’t sure if that was his personality or the alcohol stepping in for average looks.
I had a lot to think about. It was clear to me he was interested in me. The next day, he texted to see if I was interested in catching a movie that evening. I told him I had plans to hang with friends locally, but if they fell through, I’d let him know. When I decided to keep my plans, I texted him to let him know. He wasn’t all that concerned considering he had hopped on a flight to Boston to hang out with friends and go to a party. Yup, hopped on a flight that day. He obviously didn’t have a planned flight considering he asked me to go to the movies — Unless he was planning to fly me to Boston to do so…
That night, while out with my friends, I called Boston. He told me some of his new exciting war stories, and I told him of my trepidations about Deep Pockets. He told me I was nuts to write him off based on financial differences, so I decided to see where things went over the next week or so.
We texted a few times more, but interest wasn’t strong on either end as the text messages slowly came to an end. I was on to the next prospect…
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Posted by One Gay at a Time in Gay Dating on February 10, 2012
Sunday afternoon, I tried to see if Smiles would want to do something fun the following day since I didn’t have to go to work. Sadly, he had work to do. He was trying to build up a company from scratch, and it is a lot of hard work, so I understood. What I didn’t expect was he would be busy he wouldn’t be able to find the time to pick up the phone and call or text.
Monday passed with me planted on the couch watching TV all day while surfing adam4adam.com and reactivating my Grindr account. I was just seeing what was out there, but as the afternoon progressed, I started to think toward the future while examining the past.
I realized I wasn’t happy. I equated my relationship to the struggle of Sisyphus, a king punished by being compelled to roll an immense boulder up a hill, only to watch it roll back down, and to repeat this throughout eternity. I was constantly putting work into the relationship only to find I wasn’t receiving much benefit from it.
I had given Smiles more than his fair share of chances to finally woo me, and he failed. I enjoyed his company, and he was a very nice, successful, good-looking man, but the time had come to move on. It just seemed he wasn’t that into me, and I realized I deserve better. Since I had been on the journey to this conclusion for quite some time, I wasn’t that broken up about it. I’ve had varied reactions to the end of relationships in the past. I moved on with closure after my mutual breakup with Broadway. I had slight some minor cardiac scarring after I ended things with San Francisco. I was a wreck when things went south with N — Losing ten pounds in a week (Not proud of that).
This epiphany wasn’t all that earth-shattering for me. Things had been on the decline for some time. This certainly didn’t come out of the blue, so the blow was lessened.
I actually started to get slightly angry about things. I felt used. I recalled asking Smiles on our first date why he was on Grindr, and he had mentioned he was lonely. I realized I was someone to pass the time for him. I was someone he could go to dinner with so he didn’t have to eat alone. I was someone he could have the occasional romp in the sheets when he was in the mood. I was a seat warmer. He never had any plans to forge a relationship with me, and this made me really feel used.
I wanted more. I deserved more. And I was going to find more. I started searching once again on a4a and Grindr. These are clearly not the best place to find Mr. Right, but it couldn’t hurt to try. Once again, it was just going to be a lot of work.
On top of it all, our sex-life was minimal. As a result, I was horny. I was hungry for some good sex. Over the summer when I was having my wild time, I felt I started to really hone my craft. I had numerous guys constantly hitting me up for seconds, thirds, and more. It was great for my ego, and I craved a really good romp in the sack.
That’s when I turned my efforts toward Grindr. I wanted to find a local guy with a hot body. I knew it wouldn’t be easy from past experience, but maybe some new hotties moved into the area in the three months I’d been away. I started talking to one guy for quite some time. We even started to Skype with each other while I watched TV. He lived very close and had a really nice body. He was Asian, which doesn’t quite get my engine roaring so there he wasn’t a relationship prospect, but we could at least start on a friendship. We face-time chatted most of the evening. I gave him full disclosure on the situation. We even discussed him coming over to hook up, but in the end I decided to be good.
Afterall, I still hadn’t officially ended things with Smiles yet. It wouldn’t be right. I’d already betrayed that relationship once, I didn’t need to do it again, not matter how resolved I was about its end.
I got an offer from a man I’d had a tryst with in the past. He begged me to come to his apartment, but it was cold outside, and it was getting late. I had work the next day, and I needed to go to bed. I told him I’d take a rain check.
My new friend went to bed, and I continued to figure out a way to satiate my libido. I figured I would hit up some old friends in my Skype contact list. One of the sexiest men happened to be online. He lived in South America on an island, and I wanted to do bad things to his body. It was amazing. I loved camming with him. The only issue was he had a big thing for me. He always begged me to be his boyfriend, no matter how many times I told him it couldn’t happen because we are so far away. He begged me to come visit, but I told him I couldn’t afford the flight. I wasn’t about to fly to South America for a booty call. But if he lived anywhere close, I would have been over there in a second!
I convinced him to have a little fun on camera until I finished. As usual, it sapped all the energy from my body, and I jumped into bed and dozed off without a thought left in my head.
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Posted by One Gay at a Time in Gay Dating on February 9, 2012
I continued my walk of shame north on Seventh Avenue. I was still dressed for a night out from New Year’s Eve the night before. I didn’t care if anyone judged me. I was in my own world. No one else existed that morning. I was utterly alone in a city of millions.
I continued to try to reach Boston through text and by phone, but no dice. Since I was going to be near his apartment, I thought I would reach out to Broadway. At the very least, I could kill time with a visit until Boston finally decided to get back to me. I called him, and he picked up after a few rings. I asked him what he was up to and told him I wanted to swing by for a visit. He was still in bed and said he needed a few minutes, but he told me to come by. I told him I was walking from the 20s, so there was no rush for him to get out of bed.
When I arrived, I walked right up to his apartment. It was like old times — A blast from the past. It’d been months since I’d been there, but it felt like yesterday. I knocked on the door, and he greeted me. I came in and sat while he finished getting ready for the day. We sat on the couch, and he asked how my New Years was. “Tell me stories. You always have good stories to tell me,” he added. I told him what I did the night before. I gave him the cliff notes because I didn’t want to belabor the point. The wound was still fresh and bleeding. He shrugged it off and suggested we go to the diner for breakfast. I kinda loved that about him. He knew how I felt about it, so he did his best to brush it under the rug.
I agreed to go to breakfast, but I told him I’d already eaten. I would keep him company, and we could catch up. It’d been since the summer since I’d seen him.
Breakfast was nice. He told me about the party he went to the night before and all the guys he was pursuing. As usual, he was very passive about it. “I dunno if I really want to see him again…” he’d say. He’d find something completely superficial to judge the guy about so he wouldn’t have to put in the effort.
Since Smiles’ birthday gathering, we gained a mutual friend. We learned this from Facebook. The guy who I palled around for the night had been at the party Broadway went to the night before. They interacted, but it wasn’t a positive interaction. Broadway was remotely interested in this guy, but apparently he gave him the cold shoulder. This really turned him off, but I assured him my birthday buddy was a really great guy. If I’d been single that night, I probably would have asked him for his number. Broadway wasn’t sold.
Ironically enough, Smiles and I were almost at this party. It wasn’t until Smiles learned of the over-priced charge to enter that he decided we were just going to the house party. It was crazy to realize Broadway, Smiles and I were all swimming in the same circles in New York City. Apparently the gay community was pretty tight, even in a big city. It put it all into perspective. It also made me realize the picture of myself I painted when I let a stranger suck on my neck and face in front of the guy I was dating.
I wasn’t feeling very talkative, so I did a lot of question asking and listening. When Broadway finished his breakfast, he asked for the check. He wasn’t feeling well, so he wanted to go back to bed. I checked my phone, and Boston still hadn’t gotten back to me. I guess I wouldn’t see him before he left the city.
I walked Broadway back to his apartment and said goodbye. Something I learned from him was it is okay to kiss an ex on the lips when you see them. When I first came out, I was fascinated by how often gay men kissed each other. This was completely foreign to me and not something I was comfortable with. Even if I travel in a big gay pack, I don’t think I would be kissing my gay male friends. But, I felt comfortable kissing a man who I had kissed over a hundred times. So we exchanged a kiss and a hearty hug before I made my way to Port Authority to snag a bus back to Hoboken.
While I walked to the bus, I texted Smiles: “Since I have the day off tomorrow, can we do something fun?” I was hoping I could do some damage control and get us back on a happy track.
It wasn’t long before I received a simple text in response: “I have to work tomorrow.” I was already picturing a Monday afternoon with me sinking deep into the couch by myself in front of the TV. I was very disappointed, but it’s not like I had anything to say. I was the one who royally messed up here. I was going to have to deal with the consequences.
Later that evening, I talked to Boston on Facebook. I told him what I did and how things played out. We didn’t talk long, but promised to come back to the topic when he had more time.
I had time all day to assess the situation. Why wasn’t Smiles mad? I realized I wasn’t happy about this. It hurt even more. It showed me quite clearly how little I meant to him. I didn’t see any way to recover from this. I was pretty sure our relationship was over. And, since I’m pretty much a high schooler in the gay dating world, I hopped back on adam4adam.com and Grindr that night to see what was out there. I wasn’t throwing my line into the sea, but I could at least swim around and see what kind of fish were out there…
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Posted by One Gay at a Time in Gay Dating on February 8, 2012
New Year’s Day, Smiles woke me in the morning. I was in a complete fog. I immediately began wracking my brain to remember how the night ended. I knew we had sex, and once again, I could only remember a tiny flash of the intimate moment we shared the night before but no more than a flash. I could remember being p*ssed at Smiles on the walk home for walking five paces in front of me. And, I could remember smoking on the balcony.
I had now realized I completely wiped my phone, so anyone who texted the night before would certainly not be receiving a response from me.
Smiles was up and about walking around the apartment. I searched the room for my briefs, but couldn’t locate them. He came in the room and retrieved them for me from deep within the sheets. I had a massive headache, so he gave me some pain killers and water. It was sweet of him to take care of me in my still inebriated/hungover state. I asked Smiles about leaving the party, and he recounted the details for me. It was clear he wasn’t thrilled about it, but he also wasn’t holding it against me. The he uttered, “And I haven’t even gotten to the fun part yet!” he added.
He was going to leave it at that. I told him he couldn’t do that to me. He had to tell me what else I did. He asked if I really wanted to know, and I insisted. This is the “fun” part:
Apparently, the advances made by the guy on the balcony didn’t end there. Clearly he was persistent, and clearly I was vulnerable and well intoxicated. Smiles recounted a scene for me that drained all the blood from my face. “[The guy who sang my praises to Smiles] came up to me and asked me if you were okay. When I told him you were fine, he replied, ‘Are you sure? Because he’s making out with someone else on the couch.” I nearly passed out. I couldn’t believe it. Was I really capable of that? Could I really do that to another person after witnessing N do that to me? Was I that heartless?
I racked my brain trying to remember any bit of a make-out session on the couch. A vague image came to mind of this man kissing all over my neck. I remember asking him to stop, but also couldn’t remember putting up a strong fight. I’m not sure if my mind was making this up or if it was reality. Either way, my actions were deplorable.
I froze. I didn’t know what to do. I didn’t know what to say. I couldn’t believe he was still speaking to me. I couldn’t believe he still had sex with me that night after that. I was mortified. What was going on? My head was spinning!
“What did you do? Did you come over and stop it?” I asked. He shook his head no.
“[Smiles], I don’t know how to apologize for that. I can’t believe I did that! I can’t believe your still speaking to me right now. I can’t believe you didn’t leave me there. I don’t have words for how sorry I am. I don’t remember any of that. At all!” I plead.
“It’s okay. You were drunk. It was New Year’s Eve. Don’t worry about it,” he said.
Don’t worry about it!? I made out with another guy in front of you, and you tell me don’t worry about it?! Should I be happy you’re not that upset about it, or should I be even more hurt that you’re not phased by it. “I still don’t know what to say. I can’t believe I did that,” I added. He just looked back at me with a face that said, “Yeah. You did that.” I wanted to slither away into darkness and forget the world.
We continued to get ready for brunch and walked out the door. As we walked, all I could think about was how disrespectful I was to the man I’d grown so fondly of. Sure we had our moments where I questioned our relationship, but what I did was unforgivable. I would not have been able to forgive myself for what I did. When N did it to me, it signaled the end of our relationship.
I did this in front of his friends — Many of which I told I was dating Smiles. I made myself look like a complete whore, and I made Smiles look like a fool. The man who was singing my praises was the man who witnessed my greatest downfall. This was one of the worst things I’ve ever done in my life, and there was no making up for it and no undoing it.
I continued to tell Smiles how bad I felt about the whole thing. He was trying to make conversation and ignore the subject, but it was all my mind could fixate on. “It’s fine. Stop worrying about it,” he kept saying. We ate breakfast and talked about a few things I can’t recall because my mind was completely elsewhere. I was crushed. I almost had to leave the restaurant, Extra Virgin — His favorite restaurant, so I could go outside and cry.
It was a gorgeous day, and Smiles told me he wanted to go for a bike ride. He asked what I had planned for the day. I couldn’t think. I had no plans. I was hoping to spend the day with Smiles, but clearly that wasn’t an option. I decided I was going to try to meet Boston before he left the city, even if it was at the bus stop. I had to tell him what I did. I knew he wouldn’t look favorably on me, but I also knew he wouldn’t judge me. I left Smiles with a kiss as he walked south, and I turned and walked north. I decided to walk off my disgrace.
As I pounded the pavement from 11th street to 43rd, I tried reaching Boston. He wasn’t answering the nearly twenty-five calls I made to him. I needed him. I needed someone to talk to. I decided to hit up my roommate and see what she was doing. Maybe we could curl up on the couch and watch a movie to help make the day pass by. I talked to her for a bit, but she had plans. I couldn’t bring myself to tell here what I did. I was too ashamed. I would tell her later.
I decided to call Smiles during my walk. I wanted to make sure he knew how broken up I was about it if we were to survive this. I reiterated how bad I felt and how wrong I was as I tried to choke back tears and a vocal quiver. “Listen. It’s okay. It’s in the past. It was New Year’s Eve. You were drunk. That was 2011. This is 2012. Don’t worry about it. It’s alright,” he assured me. I think he realized how upset this made me, and that was all I could do. My fate was in his hands…
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Posted by One Gay at a Time in Gay Dating on December 13, 2011
The following topic of conversation is very embarrassing and very personal. It’s not easy to talk about, but I have a strong feeling I am not the only one who suffers from the issue. Warning: It may make some of you uncomfortable. I am exposing myself in this post, but I feel I need to face my demons to be able to get over them. I also feel guilty writing about this, because it’s a bit of an invasion of privacy for others, but I also feel it’s necessary if I’m being honest with myself and this blog. I wonder if someone out there may have insight to help me and others with this predicament. I feel the need to shine a light on this issue, as no one is talking about it.
My intentions were obvious this time around with Smiles. My hand was down his pants fondling him until I was pushed away with a grunt. There was no misconstruing my intentions. After being denied sex yet again by Smiles, I felt the need to consult my council.
I called Boston for his take on the situation. I explained being denied sex on more than one occasion. His immediate response was, “Oooooo. That’s not good. Something isn’t right.”
I responded, “I know, right? I just wanted to make sure I wasn’t making a mountain out of a mole hill.”
We chatted about the issue, and he told me I needed to address the issue. “Sex is an important part of any relationship, and based on what I read in your blog, sex is important to you,” he added. We discussed the best way to bring it up. The main consensus was waiting until the relevant situation arose. He suggested I don’t bring it up over dinner. If I was denied again, I should bring it up immediately to find the root of the problem.
This was the point in the conversation where I made a small confession of my own. I was worried I may have been to blame for the quantity. I explained my climaxing issue to Boston for the first time in full detail. I told him, while I’d been with Smiles a few times, I had yet to climax. This was through no fault of Smiles. This was a common occurrence for me dating back to the days I was with Broadway. In fact, I feel it was a large part of the reason we broke up. It put a lot of strain on the relationship. He took it personally, even though I assured him it had nothing to do with him. I was still quite attracted to him and still received pleasure from sex, but I wasn’t finishing.
I never was able to find the root of my problem. For a while, I hoped it would fix itself. When it didn’t I explored a number of theories. The leading one being I hardwired my brain to function in a specific way in relation to sex.
For 16+ years, my main outlet for my sexual frustrations was viewing gay porn and pleasuring myself. I wasn’t dating men, and I wasn’t exactly a lady killer either. I would go home, open the laptop, and take care of myself. I worried my brain was hardwired to react only to that stimuli.
I wanted nothing more than to “fix” this issue. For some time, I masked it by prepping myself. If I knew Broadway and I would be having sex, I watched porn before I saw him to build up a “spank bank.” I referred to this when he got me close to finishing to get me over that last hill. It worked for some time, but eventually that solution lost its effectiveness. That’s when things got really bad. I got so stressed about it, when the moment came, there was nothing I could do but think about my lack of performance. I was so wrapped up in the issue, there was no unwinding me at that point.
I had many frank discussions with Broadway on the subject. After discussing it, we agreed not to talk about the issue for some time. It was the only way I was going to be able to relieve some of the pressure I was putting on myself. Eventually it did the trick, and I had my happy ending. However, it wasn’t a 100% solution. Most of the time, I was only able to cum after he performed oral sex. A majority of our relationship, I never climax from anal penetration. The issue was still there. It was just lessened.
It wasn’t as big an issue with San Francisco because we were an entire country apart. When I was physically with him out in San Francisco, I had no issue. When we Skyped, it took slightly longer, but eventually I climaxed. After San Francisco, I slept with a handful of guys. I specifically remember it being an issue with The Trainer. I know it’s not an issue of physical attraction, because he had a body like a god! However, I had to finish myself off that time, and it took some time.
When I was dating N, it took a long time, but I almost always finished. He started noticing my “condition” as time went on. We discussed it lightly, but I think he was under the impression it just took me a little longer than most guys to finish. As I’ve said before, I had to resort to my “spank bank.” Many times, what I was imagining involved the two of us. I wasn’t even imagining porn stars. It was the two of us in different scenario/locations other than in my bed.
Over the summer, it wasn’t really and issue for me. I had no strong connection to the guys I was sleeping with. It was purely recreation and my own need to get some crazy out of my system. I had no pressure or image to keep up. I was just having fun, and it worked.
The first time Smiles and I had sex, I bottomed. No matter who I have been with, I have never finished from bottoming. It has its pleasures, but it never had that effect on me — Hence my status as a preferred top. With Smiles, there was one time when I was very close during oral sex. I was right there, but I just couldn’t close that final gap. After we had sex other times, and I still didn’t finish, I began to morph my theory.
I have a very high pain threshold. Because of this, I wonder if I am in turn cursed with a high pleasure threshold. Maybe it takes more to get me off. I also wondered if my stimulation comes from something more visual. Maybe I need to witness the penetration to climax. Again, these are all just shots in the dark, no pun intended, but I want nothing more than to figure out this enigma. However, I haven’t been able to test my theory at this point.
Smiles expressed his interest early on to work with me to figure this out. It meant a great deal to hear him verbalize this to me. I need someone who can be understanding and patient with me if I’m going to lick this thing.
After I talked to Boston, after a drunk night at the bar, I discussed in length with D my issue. This was really tough for me because I am so embarrassed by the situation. It makes me feel like less of a man. He was helpful in our discussion and helped me feel more comfortable talking about it.
I also called to Broadway. I didn’t exactly feel comfortable talking to him about the details of my new relationship, nor did I think it was fair to him. But, he had experience with this issue. He knew what was going on with me, and maybe now that we weren’t together, he could help me find the key. When I told him I was being denied sex, he immediately said, “Something’s wrong! That’s not normal. You need to talk to him about it.” Everyone was telling me what I already knew, but not what I wanted to hear. In thinking I was partially responsible for the situation, I brought up my issue. Maybe he was avoiding sex with me because I couldn’t finish.
Broadway told me I needed to stop being so stupid about it. I was stressing myself out over it, and that wasn’t going to solve anything. I needed to acknowledge to myself the issue and go see someone about it. I told him I had been entertaining the idea of going to see a therapist, but it takes a very special type of therapist for such a sensitive issue. It wasn’t exactly the easiest thing to find in the yellowpages. He again just indicated I needed to talk to someone about it if I wanted to get over it. He also reminded me I needed to talk to Smiles directly about why we weren’t having sex more often.
The next morning when I woke, I sent Smiles a message detailing my desire for him to be in the bed next to me and how horny I was. He responded positively and seemed he would have been up for morning sex had he actually been there. I was surprised considering a few hours earlier I was denied.
We made plans for Sunday, and I went on with my pondering my issue for the rest of the day. Did he think I didn’t enjoy sex? That certainly isn’t the case. Even if I don’t finish, I still thoroughly enjoy sex and still get a body high from it. Did it bruise his ego to know I wasn’t being fully stimulated by him? I can assure him, it is me, not him. There were a million questions, but no solid answers.
One thing is clear. I need help. I cannot solve this problem on my own, but maybe talking about it with my therapist, Dr. WordPress, will help me face my demons head on and conquer them. Only time will tell…
Follow @onegayatatimeAwkward Silence
Posted by One Gay at a Time in Gay Dating on December 8, 2011
Yet another video I’d like to share. This one is a music video for one of my new favorite groups, Duck Sauce. Great song and love the sexual connotations, but may not be safe for work depending on what you do. Enjoy!
On with the story…
Every Tuesday in Hoboken is free movie night if you have Cablevision’s triple play. I do not, but I have some very generous friends who do, and they lend me their card when they’re not using it.
I asked Smiles if he wanted to catch a movie and dinner. He told me he could possibly do dinner, but there was no way he could do the movie. He had to be up at 6:30 the following morning for a work meeting, so spending the night in my bed was off the table.
While I was finishing up work, he was moving his final boxes into his storage unit from Harlem. I agreed to help him when I arrived downtown, but when I got there, he was already finished.
I walked him back to his apartment. We talked about his day on the walk. I waited while he showered and changed after loading and unloading all those boxes to go to dinner.
While he was moving the boxes, both his parents called, separately. He was a little worried, so on the way to the restaurant, he dialed his mother. Smiles said he needed to walk a while, so we kinda just went for a stroll. We talked a little about work and how he got to where he is today. We stopped in a few stores on the way. We were walking for over a half hour before we settled on a spot to grab some grub.
We settled on Peels. When he returned to the table after washing his hands, the conversation was very dry. There were many long awkward pauses throughout the night. I struggled to think about anything we could to talk about. Nothing. I didn’t know what to do. We continued to eat in silence. It was incredibly awkward. I was so worried we’d hit that point already where we had nothing to talk about. I was petrified.
Was he distracted by the phone calls? Did something happen? Who knows?
When we finished eating, we paid the bill and began walking back toward his place and the PATH. We ran into a friend along the way, and Smiles chatted with him for a short while after barely introducing me. After we left the friend, he explained who he was and how close a friend he is. I was a little surprised. If he was such a good friend, then why was he so casual when introducing me. Maybe I didn’t mean as much to him as he did to me. Maybe I was putting too much of myself out there too soon. We’d been dating for a month and a half. I thought we’d be closer knit at this point, but maybe I was wrong. Maybe I had different expectations.
As we walked, he told me he was tired and a bit out of it. This wasn’t news to me after the awkward dinner we just had. He walked me to a crossroad and said goodbye. When I went in for a kiss, I barely received anything in return. It was almost like a child begrudgingly accepting a kiss from a grandparent. I felt like a piece of sh*t.
As I walked by myself to the PATH, I wondered if this thing had run its course. How much longer were we going to go before he fully opened up to me? — Before I didn’t have to wonder where I stood with him? I was tired of the uncertainty. It was dragging me down.
I needed to talk to someone, so I called Boston. No answer as usual. College always gets in the way of our friendship!
Next, I called LES to see what he was up to. No answer, so I left a message.
Then I texted the Principal just to say hi and see how he was doing. When I came above ground on the other side of the Hudson River, I received a response from him. We texted back-n-forth for the remainder of my walk home. When I got to my apartment, I immediately climbed into bed. I was depressed. This relationship was looking pretty bleak. Silence at dinner and an awkward kiss goodnight. Once again, maybe he just wasn’t into me.
The Principal and I continued to text over the next hour while I watched some TV. I explained to him I still had some feelings for him, however, the distance thing just wouldn’t work out for me. Apparently, I opened up a can of worms there. He really did miss me. I’m not sure why I felt the need to reach out to the Prinicpal that night. I thought I passed that chapter in the story. I think I did it for selfish reasons because I needed to feel wanted again. I knew the Principal would provide that for me. Looking back, I never should have done that.
In my mode of depression, I also responded to one of the guys who had hit me up on OKCupid. I asked him if he wanted to grab a drink sometime. I was taking my friends’ advice. I wasn’t going to put all my eggs in one basket. The guy responded, and we scheduled a date for the following night…
Follow @onegayatatimeBeing Supportive
Posted by One Gay at a Time in Gay Dating on December 2, 2011
After our night galavanting around the village taking in the Halloween sights, I felt like I made a half step closer to Smiles. We hadn’t completely closed the gap, but seeing him two days in a row was a good step. We finally added sex to the mix again, and I was watching him slowly open up to me. Maybe this relationship did have potential. Maybe I just needed to be more patient.
When it comes to relationships, my major downfall is over-thinking. Luckily, I have friends. And, I have you, my faithful readers. (Oops! Did I just address the audience?) Anyway, even though I don’t have a therapist, and at times I think I need one, I have my friends.
One of the guys I swam with in college, “J,” is a dedicated reader. So much so he harasses me when I don’t post on time. You can all thank him for keeping me on schedule. We’ve been through a lot together. He was almost one of the first people I told I was gay. On my ride back from telling my parents, I met him for lunch. I planned to tell him, but at the last minute I chickened out. I was waiting until I saw him again to tell him the news, but that didn’t happen until a few months later. I am constantly reaching out to him for advice and using him as my sound board. He’s more of a help to me than he realizes.
I have a wide array of friends and different reactions I can expect from them. Some I turn to for sex advice, like my friend who knew all about my philandering on Martha’s Vineyard, even when I was trying to cover it up. Some I turn to when I’m suspicious, like A, however some of those make me unnecessarily more suspicious. Some I turn to who I know will support whatever I’m saying, like D and K. J always gives me a fair and balanced viewpoint of the situation. Boston always gives me the harsh reality dose I need sometimes. Even Broadway weighs in sometimes for advice. And nothing makes me happier than when I get advice from my readers/newly found cheerleaders.
I take everything they all say, put it through my own filter to make decisions on how to proceed. They’re all great and I appreciate them all.
Many times Smiles would tell me about conversations he had with his ex to keep him centered and sane. He was finally reaching out to me to fulfill this role, and I was thrilled!
He sent me an email asking me to call because he didn’t have my phone number. I called, and he explained how he got a replacement phone from Verizon and it was defective. I joked it was the user and not the device that was a problem. He was using a very old clamshell phone he’d used years ago.
He also told me he was in the middle of a breakdown. He had a lot of frustrations, many of which stemmed from work. Luckily, this was something he was opening up about to me recently, so I was able to give him some educated advice. He has a problem seeing things in the small picture. Too many times he looks at the big picture too soon and gets overwhelmed. I did my best to calm him down, and I think I did a fair job. Apparently, others were giving him contradictory advice to my position, but I stood my ground once again. I asked him what he really wanted. If there were no restrictions, what would make him happy. I questioned why he was settling for things just because he thought it was what he was supposed to be doing. It seemed like he was taking my advice to heart.
He told me he was going out to get ice cream instead of going for the run he planned on to exert his frustrations. As he read aloud the flavors in the cooler, I encouraged him to pick something indulgent and go home and have at it. He was stressing a lot and needed to take the time to relax. Sometimes I wonder if he forgets to step back and have fun.
When he got back to his apartment, he was feeling better and was ready to dive into his pint of Ben and Jerry’s. He thanked me for the pep talk and said goodnight.
I went back to watching TV on the couch, but I had a smile on my face. He turned to me in a time of need. I finally felt needed and appreciated. I wanted to be more integrated into his life, and this was a step in that direction. I sat there thrilled a the new development.
Was this the foundation of a relationship?
Follow @onegayatatimeEvery One But the One I Want
Posted by One Gay at a Time in Gay Dating on November 22, 2011
Friday arrived, and I was starting to nail down plans with Smiles for the night. He had things to do all day, so we planned to grab dinner and then head to his friend’s birthday party.
This meant I had time to kill after work. My good friend A asked me to grab happy hour drinks with her. She recently moved our of Hoboken into the city with her boyfriend, so I was already seeing a lot less of her. We were due for a catch-up.
She picked a place in the Flatiron District that’s known for their happy hour. We cozied up to a spot at the bar and chatted about our new situations. It had been a while since I caught her up on the status between Smiles and I. I took her for a ride on the roller-coaster ride of emotions I’d been through. She gave me advice on how I should proceed and things I should watch out for. After five years, she knows me quite well and can predict a lot about me, so I’ve come to listen intently to what she says.
She also took the time to talk about the new challenges she faced moving in with her boyfriend. I tried to give her my two cents for what it was worth. My biggest advice to her was to pick her battles. On the things she could let go, she should, but on the things she really cared about, she should make a stink. That way, he would realize with more poignancy when he was doing things that got under her skin.
In the middle of our conversation, Smiles called to discuss dinner. He chose a place about two blocks from where we were drinking, and we agreed to meet in a half hour. When the time came, and A and I had our fill of cocktails, we walked to the restaurant Smiles chose. I coerced her into coming along to meet him since none of my friends had the opportunity yet.
I introduced them to each other, and Smiles invited her to join us for dinner. A had plans to meet her boyfriend for dinner, and I could tell she was looking for a quick exit, so she agreed to sit with us for a few minutes. She was already running late. I appreciated her making the extra effort, and gave her the out she needed. I told her to get on her way.
After she left, the conversation with Smiles was slightly forced and awkward. I was having a hard time breaking through and there were periods of silence. I learned he was feeling very sick and his stomach was bothering him. He had issues with his appendix, and it was inflamed and bothering him again.
Now, I was worried. I genuinely cared for him and my paternal instincts kicked in. I was worried for his safety and said, “Don’t be a hero on me here. If you aren’t feeling well, we can go at any time. Don’t soldier on on my account.”
“Thank you for your concern, but I’ll be fine,” he replied.
The rest of the meal was pleasant, but quiet. I reached my hand under the table to rub his knee to try to make a better connection while we chatted. That, and I was still worried about his condition.
When we finished dinner and desert, we had some time to kill. Smiles walked around the neighborhood looking for a massage parlor (legit, not sexual) in which to kill time before the birthday party. We couldn’t find one still open to take advantage of, so we hopped in a cab and made our way to the party.
When we arrived at the party, I was slightly overwhelmed by the crowd. I’d never been to a party so heavily skewed male in my life. I learned the birthday boy was gay, which answered a lot of questions for me.
We found a comfortable spot to plant ourselves and each grabbed a drink and something to nosh on. We made a friend and chatted with him a bit. He was an extremely jacked and cut black man who is an interior decorator. It was interesting hearing him talk about his occupation, all while looking at someone who looked like a personal trainer.
After some time, this man turned to us and said, “Oh. Are you two together?”
Both their eyes focused on me. The pressure was on. I didn’t know what answer Smiles was looking for, but I saw this as an opportunity to gauge his reaction. I tilted my head slightly to the side nodding and said, “Yeah.”
Our new friend called attention to and questioned my head tilt heavily. I pointed out we didn’t know each other all that long. I still look back and wonder if Smiles was actually looking for me to say yes. I still wonder if he was being distant because he thought I wasn’t fully invested in our budding relationship. Of course I wanted to say yes, we were dating, but I didn’t know where his head was at the time. I didn’t want to scare him off by being overzealous.
We were nearing the time to head out for the night, but I needed to use the facilities first. That was particularly a challenge because the bathroom was being used by a few to sign a birthday book photo album. Finally, I gave up and assumed I could go when I got back to Smiles’ apartment.
We went downstairs and hopped in a shared cab with one of the female guests from the party. As we progressed, I learned I would not be going back to Smiles’ apartment. My destination was the PATH to go home. I was slightly shocked and annoyed. It was a Friday night. Why wasn’t I being invited back to his place. I know I’d never been there before, but this was a bit ridiculous. It was around midnight, and I was dreading my trek back to Hoboken.
He hopped out of the cab with me. We said goodbye on the street with a quick kiss, and I was on my way home. I’m not gonna lie. I was hurt. I felt rejected. There was only so much rejection I could take.
As I walked, I pulled out my phone. I called Boston, but of course, he was still ignoring my calls. I left him yet another voicemail. I also called my new friend to see what he’s been up to. No answer either. Finally, I texted the Principal. It’d been a while since we chatted, so I thought I’d given him enough space. We began texting, but I told him I’d have to continue the conversation on the other side of the river.
While waiting for the PATH, I nearly p*ssed my pants. The train going into the city dropped off a tranny who felt the need to flirtatiously wave at me and say hi. When it finally arrived, I leaned my back against the wall and closed me eyes to concentrate on something other than my bladder. Two women were in front of me on the crowded train, and around a turn, one fell into me. They started arguing with each other and engaged me in conversation. Though not stated outright, I learned they were a lesbian couple, and they were hot. We had a long conversation, and when we arrived at the Hoboken stop, they invited me to come hang out with them. They had no idea my preferences fall in the men category, and they were inviting me back to their place. I used my bladder as an excuse and said goodbye. It was early enough, but I was not in the mood to play.
While speed walking home, a very large black girl grabbed my arm, pulled me towards her, and shouted, “TAKE ME HOME WITH YOU!” I ripped my arm free and continued to walk home, all the while texting with the Principal. I was flirting slightly, but not to the point of crossing the line with him. I missed talking to him and our flirtations. I really did like the guy, but the distance was still killer.
When I got home, I relieved myself and hopped into bed. I was disappointed I was there alone, but I opened up a whole new can of worms with the Principal. He still wasn’t over me, and I just scratched open that scab again. I even went as far as to pull up Grindr again for the first time in over a month.
It was just my luck. The one I wanted to be spending my night with just sent me on my way, while everyone I didn’t want anything to do with seemed interested in me.
Furthermore, I wouldn’t be seeing Smiles the following day. Originally I was planning to go to a horse race in New Jersey and invited him to join. When the day was approaching I was no longer interested in going and sold my ticket. I was hoping to spend the day with Smiles, but I learned he was going to Six Flags with friends — without me. I understand he has a life of his own, and I don’t have to spend every waking moment with him. But at this stage in our relationship, I wanted to spend more and more time with him. I certainly would have invited him on a fun trip such as the one he was going on. Apparently, he didn’t feel as strongly for me. A clearer picture was being painted for me. Maybe he just wasn’t that into me.
I realized things weren’t going as smooth as I would have liked, so I set myself on entertaining other ideas…
Follow @onegayatatimeSex On The Beach
Posted by One Gay at a Time in Gay Dating on September 28, 2011
Friday had come and gone on the island, and I behaved myself. I was trying to enjoy my time with my friends and stop thinking about finding a guy to hang out with, hookup or not. But, when Saturday rolled around and most of my friends were all coupled up, I started feeling lonely once again.
We went to a bar in Oak Bluff, Offshore Ale Company, to pregame for a night on the town. We ordered plates of french fries and tried some of the many beers they offered on tap. Everyone was well on their to a drunk night.
Throughout the night, I texted the Russian and tried to get him to come out to the bar. He wasn’t interested. However, he was quite horny and was looking to meet up with me. He proposed we hit up a remote stretch of beach between Oak Bluff and Vineyard Haven. He told me he’d drive over and pick me up in twenty minutes. I had patchy service everywhere on the island (Thanks for nothing T-Mobile!), so I was worried he wasn’t going to be able to reach me. Ironically, that night at the bar, I had exceptional service, but almost forty minutes passed by with no word from him. I texted, but I received no response.
I figured he was either running behind or something came up, so I contined to hang out with my friends. Ironically, I ran into my college teammate’s best friend whom I’ve drank with many times in Hoboken. We chatted a bit before he needed to leave, and then I made my way back to the rest of the gang.
I excused myself to go outside to call the Russian and see what was up. I told everyone I’d be back in a minute after I made a phone call. When I got outside, I saw him standing by his car. He apologized for not getting back to me because he forgot his phone at home. I hopped in his car, and we left for the beach. I texted one of my friends to explain I wasn’t coming back in the bar, but I would join up with them later in the night.
We pulled off the road into a small parking lot by the beach. Just as we were walking down to the sand, another car pulled up. We figured we’d need to walk a bit to get out of site of the new arrivals. It didn’t help the moon was bright that night. (Warning: The following may be too graphic for some). When we found a spot, we started to make out. He unbuckled my belt and unzipped my pants. He got down on his knees in the sand and went to town. He felt amazing. Already, this was much better than the ginger and the construction site. All attention was coming to me, and I was basking in it. He took off his sweatshirt and laid it on the ground and laid down on his back on top of it. I laid on top of him. By now, both our shirts were off and our pants were around our ankles.
We agreed there would be no penetration, but we were going to have our fun in other ways. And, boy did we. We tried many positions and permutations, trying to avoid getting sandy at all times. After we finished decorating the sand, we got dressed carefully and walked back to the car. The last thing I wanted was to spend the rest of the night at the bar with sand in my clothes and boxers. We sat on the hood of the car and shared a cigarette. When it was finished, we hopped in, and he drove me back to town where my friends were drinking and dancing at the bar.
I arrived too late and was not granted access, however, this worked out well because some friends were heading home anyway. I joined them to head home for some late-night mac n’ cheese.
It was nice to have a friend with benefits on the island. He lived on the island year-round and makes his living in various ways, one of which is photography. This would be the last action I got on my vacation, but that didn’t mean the conversation ended there.
Since leaving Martha’s Vineyard, I became Facebook friends with the Russian. The Boston guy with the girlfriend has made it a point to text and email me the dates he is coming to New York City. The ginger photojournalist has texted me once to reiterate the good time he had and to ask how the rest of my vacation was going once he arrived back in D.C. Overall, it was a nice ego boost. Apparently I’m that good and hot enough they felt the need to followup.
Most likely, I will never see any of them again, but I take with me some fun memories and new experiences. Just as my vacation was ending, my priorities began to shift. Sex was starting to severely lose its mystique. It tends to do that when you have meaningless sex. I needed a change and this was a good transition point. When I got home, things were going to be different — Or at least that was the plan…
Follow @onegayatatimeIs This A Porn Shoot?
Posted by One Gay at a Time in Gay Dating on September 27, 2011
After meeting the ginger, I was talking to a very attractive resident of Martha’s Vineyard who is originally from Russia. He is very attractive and very sexual. I attempted to invite him to meet us at the beach or come out with us to the bar for two straight nights, but he declined every time.
Instead, while out to dinner one night before hitting the bar scene, I came across a guy on Grindr who happened to be at the same restaurant. He seemed nice enough. When we finished our meal, I walked up to the bar to meet him and introduce myself. My friends weren’t far behind. It took all of three seconds to realize I would not be interested in this man from New York City.
As soon as he opened his mouth, it was quite evident he was a big ol’ mo. He is a 6’4″ ball of flaming queen. I couldn’t get out of there soon enough. Of course, I was too polite to simply walk away, and we exchanged numbers. And, just my luck, he was heading to the same bar my friends and I were going to. I did my best to hustle my group along except one of my friends stepped in to “help me out.” She didn’t quite realize how uninterested I was in this guy.
Our group split, and half of us went to the bar — The other half went home to bed. The Grindr guy and his straight friends followed shortly behind us. All the straight guys began hitting on the girls with me. I put a pylon between the Grindr guy and I so I wouldn’t have to engage him on conversation further. He started to chat with one of my female friends while I stood in the background and made myself as unattractive as possible. My friends and I were trying to see who could look more pregnant. Classy, I know. When we all finished our one beer, we moved on, but not before Grindr Guy grabbed me and tried to plan a beach trip for the following day. He was going to text me where they were, and we were expected to join them. That never happened.
So, just when I didn’t think I could dive any deeper into casual sex, I come to surprise even myself. The following morning, I was chatting with a good looking guy from Boston who was very discreet and had a girlfriend. He was looking for some action. I was only half interested. I was still trying to make things happen with the Russian. We were heavily flirting and exchanging pictures. He asked if I found any other hot guys on the island. I replied, “I’ve yet to see any serious talent since I’ve arrived.” I wasn’t about to share the Russian with him. That’s all I needed was for him to scoop him out from under me. He was very interested in me, but explained he was already making plans with another guy to have some fun in the woods.
At that point, he proposed the three of us get together. I didn’t know how to react. He already established he was not interested in sex but was looking just to fool around — “circle jerk” as he put it. I cautiously agreed to participate but needed more specifics before I would feel completely comfortable. At that moment, the Russian started responding.
I tried to see if he was interested in meeting up that morning instead of the party in the woods. I would go for a run to his place and spend some time there before anyone was even out of bed. That’s when I found out he was going to be the third party in the circle jerk. It’s also when the guy with the girlfriend started scolding me for trying to steal the Russian away from him. I explained I had been talking to him for some time. He of course called me on my earlier comment about the island’s lack of talent. It was slightly awkward, but we got passed it.
I learned the other two had already chosen a spot in the woods to meet. It happened to be 3.5 miles from where I was staying. I also learned I had slightly less than a half hour to get there. I threw on shorts, shoes, popped in my iPod and took off towards the site. I arrived shortly after the other two. The spot they chose was a construction site in the middle of the woods. It looked like a giant sinkhole.
When we all gathered, we tried to find a place to get out of site. I vetoed the original plan of walking into the woods, namely because I didn’t want to spend the rest of my vacation covered in poison ivy rashes. In the center of this hole in the ground were construction vehicles. Although they were the center of attention from all sides of the site, we managed to duck between them and get out of site.
(Just a warning, the following may get graphic) Almost immediately, the other two dropped their shorts to their ankles and began to jerk off. I followed suit. Every began to participate and aid each other in different combinations between the three of us. I was dripping with sweat from my long sprint, which surprisingly was a turn on for the other two. It brought me a little more attention as well. This was the first time I participated in anything with more than one other, so I was slightly intimidated. However, it was easier to relax a bit because I knew it wasn’t going to escalate to penetration. We all had our fun and eventually finished ourselves off in succession. I was on quite a high. Between hooking up in public, doing it with two guys, the run, and climaxing, I was in a different world. I had no idea how I was going to make the run back home. My legs were weak.
We decided it wasn’t a good idea to linger, especially the paranoid guy who had a girlfriend. He split off and the Russian and I casually walked back to the highway. He offered to give me a ride, and I graciously accepted. This would also help cut down on the time I was away. We had casual conversation the whole way back about our inability to connect with just the two of us earlier in the week and the other guy’s situation playing both sides of the fence. He dropped me near the house I was staying at, and we agreed to touch base later about hanging out.
I ran back to the house and hopped right in the shower. While I stood in the shower, I thought back on the morning’s events. It played out like a Sean Cody gay porn. The only thing missing were cameras. Everyone was just waking up and getting ready for the day. It wasn’t even the weekend yet, and I already had my first ginger and my first three-some. Who knew what the rest of the trip would bring. Only time would tell…
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 