Posts Tagged Sex
Birthday Smiles
Posted by One Gay at a Time in Gay Dating on November 8, 2011
I’m not gonna lie. I was nervous. I don’t get nervous very often, but I wasn’t quite sure the situation I was walking into.
Smiles had his birthday at The Jimmy, a rooftop bar at the James Hotel in lower New York City. As nervous as I was, I set no expectations going in. I didn’t want to concoct all these crazy scenarios in my head, only to not see them play out.
The morning of his birthday party, I put A LOT of thought into what I was going to wear. I care about what I look like on a daily basis, but there was so much more going on here. I was nine years his junior, which meant many of his friends would also be a fair amount older than I am. I wanted to make sure I didn’t look like “who brought the child.” I tried on numerous permutations of clothing until I finally settled on one I felt comfortable with. I even consulted with my female roommate who works in the fashion industry. I wanted to look mature and smart, but I also didn’t want to look like I was trying too hard. (I’d like anyone to argue against me that I don’t over-think things too much).
I finished work that day at 5:00. Smiles and I had tentative plans to grab dinner before his party if I got out of work at a decent hour. When that time came, he was unable to keep those plans. He had a lot of things he still needed to do before the party, so he told me we would grab dinner with one or two others following the birthday gathering. I found something to snack on, and when the time came, I leisurely walked downtown to the hotel.
I had never been to there before. When I arrived I had no idea where I was going, which only heightened my anxiety. Finally I reached the rooftop bar and was able to find Smiles standing out on the deck by the pool. I walked up to him and was welcomed by an embrace, no kiss. Still early in our “relationship,” and not fully knowing the situation I was walking into, I didn’t initiate a kiss myself.
After a minute of small talk, I walked to the bar to grab an adult beverage for myself and a soda water for Smiles. I learned the night before he was not going to be able to participate in the libations due to the cleanse he was going through for his Ayawaska ceremony.
When I returned, he had a glass of champagne, which he felt obligated to sip since someone purchased it for him. I held on to his soda water for him until he needed it. He began introducing me to the friends he was speaking to at the time. He simply introduced me by my name, or a few times, “This is my friend,” and then my name. I had no expectations, but I was curious how I would be introduced. Certainly not boyfriend, but maybe as the guy he’s been seeing? No dice.
Early in the night, Smiles introduced me to one of his friends. This guy was younger than the majority of the crowd, and I made him buddy for the night. We hit it off and shared similar senses of humor. I knew Smiles would be preoccupied all night with his guests, so I prepared myself to be more social than I normally am. I didn’t want to be a wallflower or that creepy guy that lurks around and talks to no one. I was happy to have found someone to pal around with for the night.
Then the question I was dreading all night came up. My buddy asked me, “So how do you know [Smiles]?” I simply replied, “Recent friends.” We both smiled big, and he looked at me with a perplexed look. “That’s all I’m going to get?” he asked. I took a second, cocked my head to the side as I thought about it, and simply replied, “Yup.”
I then turned the question on him. Apparently they met on Fire Island and were just casual friends now. I wasn’t sure of the timing of this, but my instincts told me they hooked up at one point. To any normal guy, these things don’t pop in their head, but Smiles and I did meet on Grindr.
As more friends of the younger sect (all probably about five years older than me still) started showing up, my buddy and I began chatting with them. The question came up many more times asking how I knew Smiles. When others answered, there were a few “mutual friends,” but there was also a, “the old school way — Craigslist.” My brain was in motion. In my mind, my stock plummeted right then and there. Obviously he was still close with these guys if they were coming to his birthday party. Was he still seeing any of them. We were by no means exclusive. But, seeing these guys in person made me uncomfortable. However, I soldiered on.
It had been a while since I saw Smiles, so I circled back to him. He was starving. I offered to grab him something to eat just as he was simultaneously asking me to (keeping in mind his special dietary needs on top of the new ones for the cleanse). He pointed out “his” waitress for the night. He handed me his credit card, and I ordered him some tuna tartar tacos. When they arrived, he scarfed them down as to not miss a minute of his party. I was happy I was the one to which he turned to take care of him. He enjoyed them so much, he went back for seconds.
When I returned to my conversation circle, my buddy had departed. I was very disappointed because I wasn’t thrilled with anyone that was left. However, I continued to make small talk for the remainder of the night.
The time came to grab dinner. Smiles gathered a small group of about seven of us. We walked across the street to Cafe Noir and grabbed a table. Smiles sat at the head of the table, and I made sure I snagged the chair to his right.
The whole time at the restaurant, Smiles felt a little distant. I began to read far too much into that. I wondered if he was doing that because someone else would be offended if they saw him being affectionate towards me. Was there another “me” at the table? I was shocked I got an invite to his birthday gathering so early on. Who’s to say there wasn’t someone else in the exact same position?
I had my hand casually under the table and was rubbing his knee periodically. I wanted to see how he’d react. Nothing. I was a little hurt and confused.
I wanted to make a good impression on his friends in front of him. I was able to contribute greatly to the conversation over dinner. I attentively watch the news and stay up on current events, so I was actually the local authority on the topic of conversation. I wanted to prove to him I could hold my own.
When dinner ended, we walked outside in a large group. Many of his friends were going to smoke and invited him to join. He declined (the cleanse) and said he was going home. They also specifically asked me if I would come, but I too declined. I was hoping I was going home with Smiles. We split from the group and walked towards his place.
We weren’t a block away before he said, “Do you mind if I throw you in a cab instead of walking you up to the PATH since I don’t have a jacket and I’m freezing?” Apparently I would not be going home with him that night. I assumed he would invite me back to his place considering it was 1:30am. I even brought a spare shirt to work that morning for the following day should I be spending the night in the city. That wasn’t going to be the case.
At that point, I said goodbye to him on the street and began my trek up to the PATH. I was dreading my commute home since everything runs on a sparse schedule at that hour of the morning.
It also turned into a very long solemn walk because I was very disappointed with how the night played out. I felt so far away from him. A few nights prior, I thought I made so much excellent headway with him when I got an invite, but after the event, I had a very different picture in my head.
I tried not to let it get to me, but I can’t lie. It ate away at me for the rest of the night and into the next few days. I’m sure the fact that I had about six Johnnie Walkers didn’t help. At dinner the night before, he casually mentioned taking me to the opera that Saturday, so it was planned I’d see him again, and soon. But, it was mentioned so flippantly, I wasn’t sure I was officially invited. So many crazy ideas were floating through my head.
I was trying to follow friends’ advice to make myself a little less available to him. I was told I should make him seek me out, instead of the usual me seeking him out.
With that, I attempted to go about the rest of my week without driving myself insane, but that wasn’t going to be easy…
Follow @onegayatatimeDinner and a Stroll Along the River
Posted by One Gay at a Time in Gay Dating on November 7, 2011
Following my great date with Smiles, I couldn’t get enough. I relished every phone call, every text, every moment I spent with him. I suppose you could say, I was gaga.
Is Smiles the greatest guy out there? Is he the best guy out there for me? Who knows. I don’t know him well enough to make that assumption. However, my appetite was wet, and I wasn’t satiated. He is a really great guy, and possess a lot of the qualities I seek in a man. I was cautiously optimistic — Fingers crossed.
After our last date, I texted, “Had a great time last night btw :)” He responded, “Me too!” That being said, I asked him out once again. The following day, I said, “So… When do I get to see you again?” He proposed Tuesday night. I was a little surprised. I was waiting to hear Wednesday night, since he invited me to his birthday that night. I was thrilled he was interested in seeing me two days in-a-row. I was just hoping he would confirm for me once again he wanted me at his birthday celebration and wasn’t having second thoughts.
I had been apartment hunting, so when I found one, I sent him a picture. That was followed shortly after by a sexy picture of me I took last summer on vacation in California (you’ll recognize part of the picture in my Gravatar on the right). I thought I’d spice things up a little, especially since I promised him I would send the picture. He responded, “That’s way better than an apt pic!” I said, “I thought you’d appreciate…” However, he didn’t believe me when I told him I took the picture with the timer on the camera. He thought someone else took it until I went on to explain the entire situation. “You’re committed to this, huh? LOL. Good for you. Strong work,” he said.
When Tuesday arrived, I asked him if we were still on for that evening. He responded, “Yep. Barring a trip to the hospital for stitches after I punch my computer for not working and wasting my time today.” At the end of the day, he added, “I’ve calmed a bit, looking forward to seeing you. What time are you off? You don’t happen to have running shoes with you? I feel like I need a run, LOL.” After discussing my lack of running equipment, we decided on dinner at his favorite restaurant, Extra Virgin.
We grabbed a table outside the restaurant. It was that time of year right before it’s not too cold to sit outside, but it’s also not quite warm enough to be completely comfortable. We ordered our food and immediately dove into conversation. We talked about our days and what was new in our lives.
He told me he and a friend were going to a shaman to try Ayawaska (a Peruvian root similar to Peyote) for the first time. He explained the setting in a yoga studio and how it works. I was fascinated. I’m certainly not the type to be open to drug abuse, but recreationally or experimentally, I have an open mind, especially if it happens under close supervision. The point was to relax and open you mind. Many people use it to communicate with God/the spirits in a trippy way. There was slight reservation/worry in the back of my mind regarding the whole thing, but he is an adult. I knew he’d be safe.
We ate our meals (I don’t recommend the chicken pot pie at Extra Virgin, but everything else I’ve had is spectacular) and continued our conversation.

Smiles likes to order deserts when we go out. Going out to dinner is already putting a dent in my wallet that normally isn’t there. I cook in my apartment far more often than I dine out. Since I started seeing him, I was going out a lot more often for dinner. Not only that, it wasn’t exactly helping my waistline. It’s amazing how easy it is to put on pounds when you aren’t afraid of people seeing you in a bathing suit anymore.
Instead of getting desert, he suggested we go to this tea shop, McNulty’s and then grab desert elsewhere. He was looking for a specific tea, so I called the shop to make sure they were still open.
After the tea shop, we hit up a gelato place, L’Arte De Gelato. We took out gelato and walked down Christopher Street to the pier. We had a nice stroll along the pier holding hands. I pointed out a few things on the Jersey side, such as the pier I normally hit up in the summer looking back the other way. We chatted a bit at the end of the pier. I was hoping maybe for a little make out session or some hugging, but I didn’t get the feeling he was interested in that. I don’t think he noticed, but when I went to reach for his hand, that’s the exact moment he lifted it from the railing and turned around to head back to the Christopher Street PATH station. I wondered in the back of my head why he never invited me to come back to his apartment, especially since I knew we were in the neighborhood. But, I also know I needed to take it a little slower. I had a tendency to rush things, and I needed to break that habit.
When we reached the PATH station, we hugged, and I gave him a kiss goodnight. I was happy to get to see him again, and I was cautiously looking forward to his birthday the following night. It was an awkward challenge for me, but I knew I was up for it. Birthdays are always interesting situations, especially when you’re the new addition to the crowd, but something told me I’d be alright.
Mom & Dad Turn a Deaf Ear
Posted by One Gay at a Time in Gay Dating on November 3, 2011
Mother’s Day crept up on me this year so quickly I didn’t get a chance to buy Mom a present. It should be easy. It’s always my birthday weekend. I decided quickly, I would take her out to dinner in New York City. I also thought ahead to Father’s Day and suggested they both come stay with me for a weekend. I would take them both out to dinner for Mather’s Day whenever they could find the time to visit. They always look forward to visiting my sister and I in Hoboken and venturing into the city, so I thought it was a perfect gift. I told them to check their calendar and get back to me.
That never really came to fruition. Weeks passed , and they never picked a day. That was the case, until they were coming into the city on a bus trip my aunt was running to see Rent. Every time they come to visit for a show, they go to Carmine’s. I always get an invite to join for dinner or lunch even though I’m not going to the show. This time, my parents wanted nothing to do with Carmine’s. They have a lot of complaints about how my aunt orders a lot of family style pasta dishes. “If we’re coming into New York City, I want something better than pasta, especially at that price,” my mother exclaimed over the phone. I didn’t blame her. The city had a plethora of great restaurants to offer. No one should be going back to the same place every time they visit, no matter how convenient.
I agreed to take them out for dinner following the show and asked them to pick a place. Once again, this was a whole ordeal. I helped them out by picking a few great restaurants in the area to choose from. Even that was like pulling teeth. Finally, they left the decision up to me, so I chose City Lobster and Steak. In the days leading up to the visit, I learned my sister would also be joining us.
I met my sister in Hoboken and rode the bus into the city together. We met my parents at the restaurant and got a nice table by the window. It had been some time since I caught up with my parents, even though I call several times a week just to chat when I’m bored and walking somewhere.
We talked a bit about the show before the topic of conversation shifted elsewhere. At one point, my mother asked me what I’d done over the weekend. I explained my successful date with Smiles and discussed how I finally had a successful third date. “What does that mean?” she replied. I said, “I have had a lot of unsuccessful first dates, but I finally found a guy I liked. In reply, she said, “Oh,” and smiled.
After the ten seconds we spent talking about my love life, she immediately turned to my sister and asked if she was still dating the doctor she had been seeing. I was a little infuriated. This was at least the fourth time she’d done this to me. Every time I brought up a guy I was “dating,” she changed the subject to the guy my sister was dating. She still wasn’t comfortable talking about my dating men. I don’t know why this is. She has gay friends. She’s very accepting of them. Why isn’t she comfortable with mine? I know these things take time. Trust me, I’m not taking that for granted. However, I came out to my parents over a year ago, and they still weren’t quite okay with it. I know I’ve concentrated on my mother’s reaction to this and not my father’s. He didn’t really react much at all. Just head nods. I only single out my mother because this is something I would talk to her about and rarely my father, even if I was dating a woman. I wanted to be able to talk about it with them. It is an exciting part of my life at times. Maybe I need to change that. Maybe I’m not giving him a fair shot. Maybe he could become an ally to bring my mother to terms with my sexuality. Only time will tell.
I discussed this exact exchange with my sister on the bus on the ride into the city. I predicted this would happen when I told her I was going to mention how things were going with Smiles. She suggested I not cause a commotion for dinner considering it was a gift. I explained I wasn’t going to attack them or anything, but I wasn’t going to shy away from the issue anymore. I was going to bring it up, whether they liked it or not.
After dinner, my sister and I went to the bar to meet some of her friends. As we walked, I told her how p*ssed I was. She conveyed I was probably hurt, but I corrected her in that I was p*ssed. She understood. She tried to keep the conversation going when I was talking about Smiles, accentuating the fact that I had gone on so many unsuccessful first dates, and this was a big deal. But, it didn’t exactly work. I asked her to go to bat for me a little. I asked her to tell my parents how disappointed and p*ssed I was about the issue and to ask them why it was happening. It wasn’t an easy conversation to have with them, but I was hoping they’d be a little more forthcoming with my sister, since it wasn’t her feelings they’d be hurting.
Those test results have yet to come back from the lab. In the end, I understand they’re going to have a hard time with it. I would have a hard time if my son came to me and told me he was gay. My heart would go out to him because it’s not an easy lifestyle to live. However, I know it’s not a choice one makes, and I would accept my son completely as the person he is. I would be thrilled he found the confidence to be himself, and I would fully support him and the man he chooses to stand by. I’m not looking for miracles. I just want them to take an interest in my love life. Growing up, they always pressured me to find someone. In a twist of irony, when I finally did, they want nothing to do with it. Only time will tell how this plays out, but when the time comes when I want to bring someone home for a holiday, it’s going to be like ripping off a band-aid, when it could have been an evolving process…
Follow @onegayatatimeSmiles Crosses the Hudson
Posted by One Gay at a Time in Gay Dating on November 2, 2011
After a very successful date with Smiles, I was left wanting more. Of course I was on Cloud 9, but I couldn’t let my crazy flag fly quite yet. I had a great time with him and a connection was obviously there, but I had to check myself. And, I couldn’t put all my eggs in one basket.
Ironically, Smiles showed his hand well before I even had the chance to show mine. Somewhere in the confusion of emails, he replied to an old email I sent him eleven days prior. It was in reference to the first night I met him. I asked him, “How would you feel about meeting up Thurs. happy hourish??” He responded to that email saying, “Done.” He thought I was asking him out again, but in reality, I was asking him out for the first time (the first time we met at Employees Only). I can’t say I wasn’t thrilled with the response. It showed he was as interested in seeing me as I was in seeing him.
Once I realized what happened, I responded to his email, and now that I had his number, I sent him a text: “While I may jump the gun when it comes to emailing you, you’re the complete opposite. You ask yourself out and respond to emails a week old. I asked you to go out for happy hour 2 Thurs. ago, not this coming Thurs. I can’t meet up this Thurs. I have volleyball, but I’d love to meet up Fri. if you’re available.”
He laughed at the situation and told me we’d make plans for Friday after work. When Friday arrived, I texted him and said, “What’s the plan?”
He responded, “I was thinking it might be fun to go to the Standard Beer Garden for a drink and play ping-pong then go up to deem for new or since I haven’t really been to Hoboken, grab the PATH from the village afterward and find dinner somewhere over there. Thoughts? Preferences?”
Obviously autocorrect was hard at work here. I had no idea what “deem for new” was, however, that wasn’t what I was concentrating on. The fact that he offered to come to Hoboken spoke volumes to me. When I started dating guys in the city, I knew I was going to have to be the one to commute in. No guys in the city like to come out to Hoboken. They think it’s this far off land, when really it’s easier than going over to the East Side.
“Beer Garden and ping-pong sound great. Hope you bring your A game 😉 Don’t know what “deem for new” is, but we can hit up Hoboken too…” I responded.
He replied, “Harlem for bbq. I hate this autocorrect. Just give me my keyboard back.”
We met right after work and had a few beers. When the ping-pong tables opened up, we hopped on. I love an active guy. I have a short attention span and love being active, so when I find another guy who’s on the same page, I find it incredibly sexy. After about a half hour of rallying back n’ forth, we finished our beers and chatted a bit. When both our glasses were empty, we discussed where to head next for dinner. Since he offered to go to Hoboken, I capitalized on that opportunity.
As we walked to the Christopher Street PATH station, he pulled me aside and planted a kiss on me. This was starting to become a pattern, and I LOVED IT! I’m not big on PDA, but when you can sneak a kiss when no one is around on the street, I get incredibly turned on. I’m not gonna lie. When I knew we were going back to Hoboken, I had a pretty sure feeling we’d be visiting my apartment at some point in the night.
We took the PATH to Hoboken and joked about the many characters riding the train. This was a new experience for him. That’s what he was looking for, either in Hoboken or Harlem.
When we arrived in Hoboken, I showed him the amazing train station. He is big on photography and architecture, so I knew he’d appreciate it. Afterwards, we took a stroll along the waterfront as I pointed out the spectacular view of New York City. He reached out and grabbed my hand. This was a completely new thing for me. I’d never held a man’s hand in Hoboken. It’s not a homophobic society, but it’s also not a very open one. Regardless, I loved the sign of affection.
We decided to have dinner at Zylo, the steakhouse in the bottom of the W. Neither of us had been there, so we decided to give it a whirl.
While we sat at dinner we chatted. We ordered drinks; of course the same since we share drink tastes, but this time it was dirty martinis with bleu cheese olives. I was nearly floored when he brought up his birthday festivities and invited me. “I’m having my birthday on Wednesday with two of my friends at The Jimmy if you’re available and would like to come.” I told him as long as I didn’t have anything else going on, I would be thrilled. That was a huge step for me. The birthday invite is no small potatoes. It’s a big deal. It means introducing me to friends. I was impressed he felt that comfortable with me already. I wondered if I would get an invite since he first mentioned his birthday. I immediately became more attracted to him and started to let my guard down a bit. I didn’t need to put up such a front about my true feelings.

After dinner, we walked outside. I grabbed him and said, “Okay. So, I’m not going to let you come all the way out to Hoboken without coming to my apartment. You up for that?” He agreed, and we set off in the drizzling rain towards my apartment. Of course, he complained about the distance, but I assured him it would be worth it in the end.
When we got to my place, I showed him around, of course ending in my bedroom. It didn’t take long before animal instincts took over, and we were all over each other.
(Warning: Following paragraph may be too graphic for some) In the midst of passion, with the lights off, he said to me, “I want to f*ck you so bad. Are you okay with that?” I had a decision to make. All summer, I lived by the policy of strictly topping. I found I did not enjoy bottoming and declared that was something I would only do for a guy I truly liked once I was in a relationship. This policy worked quite well for me, but again, I had a decision to make. Without a word, I reach into my nightstand and took out a condom and bottle of lube. The decsion was made. I handed him the condom and warned him he’d have to go slow. It had been a long time for me since my last penetration. As I’ve experienced many times with guys, “condom syndrome” kicked in, and the heat was lost momentarily. However, we quickly recovered and some great sex ensued.
Afterwards, we showered and hopped into bed for the night. After a little cuddling, we both dozed off. In the morning, I woke and went into the kitchen to make us breakfast. Shortly thereafter, he woke and came out to join me. I loved seeing him walking around in my clothes.
I poured him a cup of coffee and went back to the stove to tend to the eggs and homemade pork and apple sausages. He came behind me and gave me a hug and kissed my neck. It was the perfect gesture at the perfect time. I was really falling for him every second I spent with him. This is what I’d been searching so long for. I was happy with where things were going, but that doesn’t mean there wasn’t still a little doubt in my mind. We weren’t dating yet. As my friend loves to point out, sex does not equal a relationship. She is right.
After we ate, I walked him back to the PATH. It was Saturday afternoon, and all of Hoboken was out getting ready for the football game. We stopped in front of the PATH station, right across from the prominent football bar, Texas Arizona, and we kissed each other goodbye. Again, this is not part of my comfort zone, but I went with it. I needed to be comfortable with these situations. There is no reason I should be embarrassed or ashamed.
Needless to say, I walked home with a grin on my face from ear-to-ear. I was so elated and blissfully happy. The date could not have gone better. However, there was a little voice in the back of my head telling me to calm down and not get overly excited…
Follow @onegayatatimeHIV Testing Hassle
Posted by One Gay at a Time in Gay Dating on November 1, 2011
After I had unprotected sex with San Francisco, I came home and marched myself straight to the local clinic for the free OraSure HIV test. I couldn’t believe how quick, easy and painless the process was. And, I had the results in twenty minutes — There was no waiting around worrying.
After that, I made a promise to myself to get tested on a regular basis. It didn’t matter if I was having unprotected sex or not, I wanted to get into a routine. I entered a new world when I came out, and that new world comes with different risks. I needed to do everything I could to protect not only myself, but also others I come in contact with.
I marked my calendar back then for six months later. That day arrived, and I went back to the same clinic. When they called my name, I went into the back room and sat with the woman who administered my first test. I didn’t have any reason to be worried, but I was still nervous and anxious. She asked me what brought me in to the clinic that day for the test. I explained to her I had unprotected sex six months ago, and I came in to get tested to make sure I was still negative. I told her I wanted to make it a regular habit to get tested, so I was back again six months later.
That’s when she started to scold me. She said, “That’s not what this test is meant for. Part of the reason we give this test is also educational. If you are having unprotected sex, then the test is warranted, but you shouldn’t be having unprotected sex, especially with people you are unsure of their status. You may be having unprotected oral sex, but again, part of this program is we educate you about the consequences of that. Unless you have an open cut in your mouth, you don’t need the test.” She went on and on almost berating me for coming in to know my status. I explained to her while “I’m having protected sex, you can never be 100% sure of anyone else’s status at any given time, even if you are in a committed relationship. I wanted to start a routine of testing for my own peace-of-mind.”
She replied, “That’s not what this test is for. We’ll give it to you today, but that’s not what the test is meant for.”
I was flabbergasted. She was harassing me for being overly cautious. I was having protected penetration sex, but no one has protected oral sex these days. What’s the point. Let’s be realistic here. And, who monitors open cuts in their mouth on a daily basis. Maybe I brushed my tongue a little too rough that day. That’s not going to be top of mind when I’m getting physical with a man.
I couldn’t believe she was giving me a hard time for going above and beyond the norm. If I told her I had unprotected sex a year ago and just decided to come in, she had every right to educate me on my shortcomings, but I felt very insulted she was telling me I was wrong for being sure of my status.
Twenty minutes later, she came out to the waiting room and brought me back into the testing room. She told me my status was negative and asked if I would like a copy of the paperwork. I graciously accepted and went on with my day.
When I told friends what happened, they were shocked. I arrived at work and told coworkers about what happened, and they couldn’t believe it. My coworkers and I had actually been working on trying to win business from the company who administers the test, so we are all very versed in the product and its benefits. Many of my straight coworkers were interested in getting tested following the pitch just because it was so easy and convenient. Everyone should know his or her status — After all, knowing is love.
I could understand if the woman gave me a hard time on a financial basis. If she told me the free test was meant for those less fortunate who couldn’t afford it or felt strongly they needed the test due to exposure to and HIV positive individual, I would have understood. That wasn’t the case. She wasn’t telling me I didn’t need a free test. She was telling me I didn’t need the test at all. I felt she was doing people a disservice if this is her policy with all those who came in for routine testing. Peace-of-mind is a wonderful thing, and no one should be denied that. I had mine for the next six months, but I would certainly have to find a new location to have the test administered six months from now.
Follow @onegayatatimeSkype with Massachusetts Mainlander
Posted by One Gay at a Time in Gay Dating on October 21, 2011
Since I left the island of Martha’s Vineyard, not a day went by I didn’t talk to the Massachusetts Mainlander.
Every day, we either texted or talked on the phone. One of us would text the other to say good morning, and throughout the day, we’d call each other to talk on the phone.

I liked chatting with him. I wasn’t sure where things would go between us. We live six hours apart. I tried the long-distance relationship thing with San Francisco, and we could have made it work — He just wasn’t completely compatible with me. I always have my doubts about long-distance relationships, especially with me, but I was willing to give this a shot if nothing else was coming my way. I’m the kind of guy who needs someone present. I like coming home to a man or going to a movie or laying together on the couch. Distance is not something I welcome with open arms.
I never met The Principal, so that threw in a whole other element. Face-time was important to me. If I couldn’t be with him physically, I needed the next best thing – Skype.
It wasn’t easy to convince him to come on Skype. It took a lot of arm twisting. When we started, I could tell he was very self-conscious. He was constantly adjusting and fixing himself. He wouldn’t even speak on Skype. He insisted on typing and blamed it on his roommate being home. I kept telling him to relax. “It’s just me,” I told him. Afterall, we developed quite a bond over the phone over the past couple weeks.
Our conversation was pretty standard (abridged of course), but would need to build to grow into a full relationship:
P: I’m all warm and horny now. LOL
Me: Haha. Oh really?
P: Def. LOL It’s this really cute guy in front of me.
Me: You look so snuggly right now. Like I could nestle in the armpit and watch TV with you. The real thing would be so much better, but this will do for now 😉
P: Pizza with roomie coming soon.
Me: I’m making pizza tonight from scratch.
P: When you cooking for me?
Me: As soon as you come stay with me for a weekend 🙂
P: All weekend?
Me: Yes. You come straight from work Friday and leave Sunday afternoon, so you can get home and relax before work on Monday. We can snuggle all weekend. Maybe I’ll show you New York for 5 min, and then, we’ll come right back here.
P: LOL You’ll hate me after that weekend.
Me: Why do you say that? You know it’s not true!
P: Too much of me. LOL
Me: No such thing! What… You’d come down for the day!? THAT’S DEF NOT ENOUGH TIME TO SPEND WITH YOU!
We were both laying it on pretty thick. Maybe I was getting a little carried away, but I really did like him. He seemed like a great guy. Had he lived in the same state, I’m sure we’d have been on many dates by then.
Me: See my room?
P: I dont konw what to do with you!
Me: My big bed…
P: It looks really comfortable.
Me: There’s a whole side with your name on it.
P: You are so awesome!
Me: You are too!!
P: Think about you alot… Potential of where to take this…. Never thought it would come to this level you know?
Me: I know. You’re quite the skeptic.
P: Well, I mean it was Grindr.
Me: Grindr is just the medium. The vessel.
P: I know but… Just mesh with you.
Me: You get out of it what you put into it. Doesn’t matter where you meet someone. Still think you should have hopped on the ferry and had dinner and drinks with me.
P: That time is done though.
Me: I know. I konw. So, now you should hop in the car. and have dinner with me. 🙂
P: That’s a long drive for dinner. LOL
Me: Dinner doesn’t end at the restaurant.
I also really enjoyed flirting with him. He responded very well to it, and I could tell he was very attracted to me. I was curious if he talked to anyone else about me. I didn’t broadcast to my friends I was talking to someone in upstate Massachusettes, but I did discuss it with my roommate.
Me: Have you mentioned me to ur roommate at all? Told my roommate about you. She comes home from work… “How’s Steve?”
P: I haven’t talked to anyone about you.
P: Def. takes it to another level — Seeing you and conversation. I want to feel close to you, smell you, nuzzle… I’ve only been with 3-4 guys (full intercourse), and I def def want to be connected with you bad.
Me: I love the way you describe it — Makes it romantic, sensual, passionate. I want to toss you down on my bed and treat you right!
P: I want to be tossed. 😉
The pillow talk died down a bit, and we talked more about relationship desires.
P: I want to rub you.
Me: A shoulder rub from my sexy man when I get home from work, and he tells me all about his day.
P: And, the back of your head.
Then the conversation took a turn I wasn’t thrilled with.
P: You need a great guy close to you.
Me: First, we figure out us.
P: You’re incredible.
Me: Then, we figure out the distance. Can’t let that be an obstacle.
P: Not what I meant.
Me: I need you close to me.
P: You should be dating someone close to you.
Me: STOP TRYING TO PUSH ME AWAY!
P: I want you to be happy.
Me: I really dont like when you do this!
P: K. I’ll stop.
Me: Good.
After that short detour, we got back on track:
P: Obviously I want you for me. I’ve been wrecked by you. Not even into talking to guys right now. You fulfill so much already. OMG — You are killing me. We touch base all day every day…
Me: I want you to be my man!
P: Care about you… This.
Me: You’re adorable. I just want to hug you all night.
P: Def could get lost in those arms.
Me: This could all be yours!!! For the low low price of a car ride 😛 I don’t want to pressure you though.
P: It would be the prize of the century.
P: I just feel really good with you.
Me: And, I with you.
P: And, the sexual is like beyond crazy. LOL I can’t imagine the chemistry.
Me: We can do this again soon. Now that you enjoy it.
P: K… I really like you! 😉 Bye.
The Principal was a really great guy. I really liked him. He didn’t know it, but he was also providing me an invaluable service. He was distracting me from Smiles. I have a tendency to dive in full force, even when I barely know a guy. The Principal was giving me an outlet for this so I didn’t scare off Smiles. I wasn’t exactly using him. I did enjoy conversing with him, and I really did think he was a great guy. But, only time would tell if this relationship had two legs to stand on…
Sexy Eyes
Posted by One Gay at a Time in Gay Dating on October 13, 2011
After seeing Sexy Eyes on the street with my roommate, I decided to make him a priority. He not only impressed me, but also my roommate. She wanted to date him . He was charming and funny and had a smile and sexy green eyes that gave me butterflies.
On my way home that night, I began texting immediately. He was all but begging me to stay in the city that night with him, but I insisted I would not let my roommate walk home alone at that hour of the night. He heavily respected my decision, but also attempted to persuade me to come back on another bus after I walked her home.
Instead, I promised we would go out the following Friday. That still didn’t satiate him. He wanted to know why we couldn’t meet Thursday. I explained I had my volleyball league Thursday nights, so I would be unable to meet up. I figured he would understand being quite the volleyball player himself.
That of course was a lie. I scheduled a meeting with a guy from OKCupid. It was an interesting scenario. The guy reached out to me originally, but after chatting a bit, I came to learn he was seeing someone. He was just looking for friends. I didn’t buy it of course, but if that’s what he really wanted, I was game. I need gay friends. We scheduled happy hour drinks for Thursday evening after work.
On top of that, I scheduled another date with a guy I met on Grindr a week prior. Between these two, there would be no time to meet Sexy Eyes.
When the OKCupid friend had to bail because of a follow-up job interview, I decided to see if Sexy Eyes was available for after work coffee. I figured we could sit and chat and get to know each other a little better.
He bit. He was extremely excited to see me. Immediately following work, I walked down to the Starbucks closest to his office. He works at a financial law firm and would not be finished for the evening. He was, however, able to step out for about an hour to chat.
The conversation was mainly dominated by him, but it was good nonetheless. We talked for about an hour before I told him I needed to head home for volleyball (my other date). Our date ended with a few smooches and a hug. I was really feeling this guy. We shared a lot in common, he was older and had a respectable job, he was very good looking, he was fun to be around… The list goes on. As I walked away, he texted me telling me he wanted to kiss me more, but didn’t want to make a scene near his office. He begged me to come back into the city after my “volleyball game.” I entertained the idea in my head, but I made no promises. Who knew how my next date would go?
I met the next guy at a bar near the Christopher Street PATH station, but that will have to be tomorrow’s blog entry, because as you may have suspected, I wasn’t quite done seeing Sexy Eyes that evening. After my second date, I went home, showered and changed, and hopped on a bus back to the city. Sexy Eyes was just finishing up his own volleyball workout as I was getting to Port Authority.
We agreed we’d go out somewhere, but made no plans. When I arrived at Port Authority, I called him to find out the plan. He told me he just got out of the shower and needed to finish getting ready. He gave me his address and told me to come to his apartment. We would make a decision where to go from there.
When I arrived, I told the doorman who I was there to see, and he let me up to the apartment. I was greeted at the door with a very nice kiss, and we chatted while he finished getting ready.
Somehow, we both ended up in his bedroom just as he finished getting ready. He sat on the bed in front of me, lifted my shirt and began kissing and licking my entire torso. It felt amazing.
Between kisses, he asked if I wanted to go out or just stay in. I didn’t need to verbally answer because I was already removing his shirt. I hadn’t had sex since Labor Day. I won’t say I was a big ball of horny, but he was a very attractive and seemed very interested in me and not just my body. I wanted him. Bad.
(Warning: The following may be graphic for some) Shortly after, he was undoing my belt and unzipping my pants. He was thrilled to learn I submitted to his request to wear briefs. I never wear them, but if a man requests it and thinks I look sexy in them, who am I to disagree? He then pulled down my briefs and opened his mouth and felt amazing. It had been a while since anyone did anything with my body besides my own two hands, so I was completely enjoying the moment.
Things got hotter, and we both ended up on the bed in numerous positions. Throughout the course of our time in bed, he started playfully biting me. I’m not gonna lie. It hurt! I went along with it because they were quick, and I have a high pain threshold. But, I wasn’t entirely into it. This was something that may have to be resolved down the road. At the peak of the passion, I was inside him, and we were both thoroughly enjoying ourselves. He finished during the act, and shortly after, I finished myself off. As per usual with the guys I’ve been with, he was impressed with my finale. Something I’ve learned to take pride in based on the reception it usually gets.
He beckoned me to come join him in the shower to clean up so we could snuggle in bed. After the shower, we laid in bed together and watched the late night news. It was getting very late, and I was constantly dozing off. After realizing this, he suggested we turn off the TV and go to bed. After all, we both had work in the morning, and he had to be up earlier than I did.
The next morning, we woke at the same time. He hopped in the shower while I read over emails from his bed. When he got out, I hopped in for my turn. He told me he would probably be gone by the time I got out. I was instructed to take my time and just pull the door shut behind me on my way out. I thanked him and kissed him goodbye.
That evening, it was affirmed for me the biting had gone too far. All day at work, my chest was sore where he bit me, and when I came home and got undressed, I looked like I was abused in certain spots.
That morning, I walked to work with a smile on my face. It was a good night, and I met a good man who seemed to be interested in me. Over the few months I’ve been out and single, I’ve learned my lesson not to count my chickens before they’ve hatched. Maybe I’ve become slightly jaded in the process, and this bothered me. But, this was something I needed to start doing so I wouldn’t get my hopes up and get hurt in the end.
Follow @onegayatatimeTurning Over a New Leaf
Posted by One Gay at a Time in Gay Dating on October 5, 2011
With the passing of Labor Day, summer officially ended in my book. I was sad to see it go. Like always, it flew by in no time. Its passing wasn’t all sadness, however. My favorite season was right around the corner. The changing of the leaves, the crisp air, the smell of fireplaces… all things I loved about the fall.
Just as the seasons were transforming, so too was I. Since I broke up with N, I went off the deep end. Part of this is because I never had my wild time. While everyone else was hooking up and experimenting in high school and college, I was being a good boy. I sat there and watched everyone else experience relationships and casual sex. I was asexual. Sure, I had my fair share of hookups with women, but nothing worth writing home about.
When I finally accepted myself and came to terms with my homosexuality, I found myself in a relationship right off the bat. I never had a chance to meet new guys and discover new things. Following my breakup with Broadway, I had a short window of wild time, but it was mainly filled with dates that ended with me going home alone. Then came San Francisco, shortly followed by N. This summer was the first time I was single and gay. Did I live it up? Yes. Am I proud of everything I did? Hell no, but I also have no regrets. Everything was an experience, whether it was something I learned from or something that made me a better person.
I began to look back and examine my summer. I wasn’t being true to who I am — True to myself. I don’t have casual sex. I’m a monogamist. I crave a meaningful relationship with a special guy who appreciates me, body and soul. If I kept sleeping around, I was never going to find this. I need to make a change. I thought I would be able to ease into it when I returned from Martha’s Vineyard, but I was wrong. I needed to be more drastic. I was going to be a good boy, even if it meant the palm of my hand would be raw.
I had two friends with benefits. I needed to cut them off completely. Closet was still messaging me since we last hooked up. “Hey man, haven’t talked to you on a while. Hope all is well. Don’t want to sound insecure or anything(too late), and I know you said its not a bother to text/email you, but just FYI in case that ever changes just let me know you’re lookin for something different or you’re seeing someone else. Lol feel free to lie to me, just would rather know if you’d rather me step back… I don’t want to become one of those creepers that I keep hearing about haha. Anyway hope to see you sometime, even to meet out for a drink or something. Later man.”
I originally found both my friends with benefits on adam4adam.com, so I sent them both messages on there. I lied and told them I was seeing someone, and I wouldn’t be able to see either of them anymore: “Hey dude. Sorry I haven’t hit you up. Everything is fine. I have started seeing someone, and I decided I need to stop with hookups outside a relationship regardless of that person. I think you’re a great guy, and I had a great time with you! Don’t doubt that. I just need to find a serious relationship right now, so I’m concentrating on that. I hope you understand!!!”
While the muscular weekend hookup simply replied, “No worries,”
Closet had a few more things to say: “Hey bro, its cool. No hard feelings. I mean can’t say I’m not disappointed, cause putting the physical aside, you really seem like a great guy, and I’m glad we met. Honestly, I felt weird saying it to you before, but now what the hell hehe…you’re the first guy I was with that made me think I wanna come out(not to mention my first for a few other things, lol). Obviously not saying I was in love after a few hookups lol, but I felt something more than just empty sex. I’m considering it after the holidays this year (you know, one last Christmas where the family likes me, hehe), but I’ll revisit that one later. Anyways, you’re a great catch, and I hope you find a great guy – and my offer remains open if you wanna grab a beer, just as a friend, hit me up. Thanks again dude, and I hope our paths cross again sometime. P.s. Two more things… 1. Thanks for being so patient with me in bed and all that, even though I still need to loosen up a little (pun intended), you really made me feel comfortable. 2. If you ever run into me while out at bars or whatever, cuz I’ve been in Hoboken quite a bit lately, feel free to say hi. I’m trying to gradually cut back on the paranoia part of all this.”
I felt pretty bad about the situation with Closet. It was obvious he was starting to fall for me, but I had no interest in pursuing anything with him. I knew I was right to cut it off when I did.
Outside of my regulars, I gave up Grindr cold turkey. I knew it would be too tempting to fall into something if they were hot and looking to hookup.
I joined OKCupid, was checking ManHunt and adam4adam.com regularly to see if there were any guys reaching out to me I’d be interested in meeting. It wasn’t easy finding a man up ’til now. I couldn’t expect it to get any easier just because I stopped hooking up with random men. None of the men I went on dates with previously showed any interest in seeing me again. Pillow and The Trainer kept giving me the runaround, so I had to learn when to simply give up and move on.
I started to wonder what was wrong with me. What was I doing wrong? Without the sex and without the happy feeling I get when I have a prospective guy I’m seeing, I started getting cranky. This was going to be a learning experience for me. I needed to not only find a man, but also to find myself. In the meantime, everyone around me would to have to watch out. I was not a happy camper…
Follow @onegayatatime








