Posts Tagged trip
Letting Him Down Easy
Posted by One Gay at a Time in Gay Dating on May 7, 2012
Monday, I decided to be a good brother and pick my sister up from the airport. I drove her to Newark Airport early Friday morning before all of my Grindring, and she was arriving around 2:00.
Before I hopped in the car, I made plans with M.E. to meet up later that day. I wasn’t planning to tell him I knew about his Grindring from my bedroom. I was just going to keep that in mind when interacting with him. I wasn’t going to let myself fall for a guy like that. For us, it would be purely fun. He told me he had class that afternoon, but he would come meet me on the pier when he finished.
I was regretting agreeing to pick my sister up since it landed smack in the middle of my day. I wanted to head out to the pier and get some color while I was off from work. The forecast was looking gorgeous for the week, and I planned to take full advantage. I decided not to waste the morning and went for a run around 1:00. I came back to my apartment, showered and packed a bag for the pier. I hopped in the car and headed to the airport. My sister was delayed, so I spent about a half hour circling the grounds. When she finally touched down, I parked in front of her terminal and began reading my first Out magazine. I was becoming a full-on gay man. I finally subscribed to a clearly homosexual publication.
She came out, and I drove her back to Hoboken. We swung by the pier to drop be me off so I could get some sun, and she went home.
Around 3:30, M.E. joined me on the pier. We laid next to each other talking for a bit. I gently stroked his hand with mine. We weren’t being blatant or obvious, but we still found ways to show affection. It was a nice time. Around 4:30, the sun was beginning to set. The temperature was dropping, so I suggested we head back to my apartment. I wasn’t even thinking about this in terms of sex. I was just cold.
He gave me a ride back to my place and decided to come up for a bit. He couldn’t stay too long because he had plans for the evening. We ended up in my bedroom fooling around a bit. It was nice to have him in my bed again. Every time we were together, I enjoyed myself.
The time came for him to leave, and I said goodbye to him at the door with a kiss.
Over the next week, I didn’t really reach out to M.E., and he didn’t really hit me up either. When enough time had gone by, I assumed he met someone else. I was trying to get away from the relationships based on sex, so I wasn’t exactly protesting or questioning why his calls stopped.
One day I got a text from him asking me why we hadn’t been in touch in some time. I told him I assumed he met someone else. He assured me this wasn’t the case. He told me the reason he was so quiet was because he was trying to create distance. He was beginning to fall for me and didn’t want to get hurt. This is when I pointed out to him I knew he was on Grindr when he was at my apartment. I didn’t tell him how I knew this information. At first, he denied it and told me he was chatting with his friends about his spring break trip postponement. I acknowledged that, but also pointed out he was on Grindr while he was in my apartment. I told him how insulting that was to me. I pointed out how, by no means, were we exclusive, but to be on the app while sitting with me was not something I looked kindly upon. He apologized profusely. I told him I noticed he blocked me on Grindr as well. He told me the reason for this was because he saw me on there periodically, and it was killing him. He was imagining me with other guys, and it was getting to him so much he blocked me so he wouldn’t have to see it anymore. I told him I wasn’t holding anything against him, but it was shaping how I looked at whatever was going on between us.
He was completely torn up about it. I had a lot of other things going on in my life at the time, and I didn’t really feel like getting into it with him. I was partially using this as a way to make a clean break from him. I liked him and cared about him more than a one-night-stand. I considered him a friend who I also happened to enjoy in my bed. He was more friend than benefit. I didn’t want to hurt, but I also needed separation. There was too much going on in my life at the time. He begged me to talk on the phone, but I told him that would have to wait. I lied and told him I was with friends and didn’t want to be rude by taking a phone call.
I knew he wasn’t happy, and it wasn’t what he wanted. I needed to think about me for a change. I needed to put more effort into the men I was meeting and looking toward a long-term relationship with, rather than the men I just enjoyed having around for sex and a little companionship. It wasn’t fair to him, and it wasn’t what I needed. The time came to move on. How that would shape my relationship with M.E. was yet to be determined…
Follow @onegayatatimeBack to School
Posted by One Gay at a Time in Gay Dating on April 30, 2012
With things gently crumbling between Chelsea and I, I decided to give Middle Eastern another chance. I enjoyed spending time with him, and he certainly was a nice kid. I wasn’t sure if I could see myself dating a guy still in college, but I figured it certainly couldn’t hurt to give it a shot.
Wednesday morning while I was on my run, I did a lot of thinking. I was trying to clear my head. I realized I wasn’t all that into Chelsea after all. There were a few things about him I liked, but there was nothing there that got me truly excited to see him again. I didn’t want to waste either of our time, so I decided it was best to tell him how I felt.
While at work Wednesday afternoon I thought about him a M.E. He was such a sweet guy, he was quite interested in me, he was smart… There were a lot of great qualities there. The big question — Is he mature enough for me. I’d never dated someone that much younger than me before. I wasn’t basing this on a number. I was basing it more on his personality.
The other side of the coin was how great he was in bed. I really enjoyed being with him the first time. I fantasized about he and I having sex in the locker room shower of my gym.
When I got home that evening, I told him to come over. He didn’t hesitate. He finished what he needed to do, and he made his way to Hoboken.
Warning: The following may be too graphic for some. When he arrived, we immediately went to my bedroom. He was hungry for sex. We quickly stripped each other until we were naked and enjoyed kissing, groping, sucking, etc. It was nice to be with a man who was so passionate once again. He loved to kiss and was good at it. I didn’t have a single complaint about him. After ample foreplay, we had sex. It appeared I created a bottom. He was all about it now, even begging for it this time. It was hot. I really like how masculine he was, but also how much he was willing to bottom for me. This was an unusual combination from my experience. [I actually had to walk away from the computer for a minute because I was thinking about the fun we had and getting a bit too excited while writing this].
Afterwards, I went into the bathroom to relieve myself. I came back to my bedroom to find M.E. on his phone. He was doing a lot of typing. I encouraged him to come to the living room with me to watch TV and be somewhat social with my roommates, but he told me he’d be out in a minute. He had a few messages he needed to reply to.
Since I last saw him, he sprained his ankle. I’d been giving him some advice, having sprained both mine multiple times and being related to a physical therapist and someone who teaches athletic training. As a result of this sprain, he wasn’t able to go on his planned spring break. He told me he was working out the logistics of rescheduling the trip for another time.
I left the room and went to the living room. I’m not 100% sure why this idea popped in my head, but I wondered if he might be on Grindr. I had my phone and tablet with me, so I pulled up the app and checked it out. He didn’t show up on either. Maybe he wasn’t on there, but my suspicions weren’t fully satisfied. When about ten minutes passed, I went back to the room to see if he was coming. He put some of my clothes on and joined me. We watched another episode of Modern Family together.
While he watched, he sat behind me in the chair, and I laid between his legs watching the show. We both laughed a lot. By the time the show was over, it was late. I suggested we go to bed, and he agreed. I asked him what he’d told his roommates about where he was going. He told them he was heading home for the night.
While he was brushing his teeth, he left his phone on my night stand. My mind shot back to the chance I had to look at N‘s phone the night I witnessed him kissing another man in front of me. Boston convinced me it was a bad idea. I wasn’t going to make that mistake again. I had no problem if he was using Grindr. We were not exclusive. I was seeing other people. I just found it incredibly offensive if he was cruising Grindr from the comfort of my apartment. That was not okay in my book. I needed to know. I turned his iPhone on, and sure enough, at the top of the screen was an icon for Grindr showing he had 23 messages. I placed the phone back down on the night stand and processed what I just learned. Not only did he have messages, but he blocked me on both my accounts so I couldn’t see that he was cruising Grindr.
It was that exact moment I decided M.E. and I wouldn’t date after all. It was fine if we spent time together and enjoyed having sex, but I wasn’t going to date him long-term. I couldn’t trust him. I wasn’t mad he may be seeing other guys or even having sex with them. I was mad he was attempting to line up other guys from my bedroom. I decided not to say anything right then and there. It would simply form my future behavior.
He came back to the bedroom, and we both climbed into bed. I wrapped my arms around him and he climbed into the natural crevice I created as big spoon until we dozed off.
When we woke in the morning, we fooled around a bit. I had to go to work, but I made sure to set an extra early alarm to allow for a little fun in the bed followed by a shower with each other. It was sexy and a nice way to start my day.
We left together, and he gave me a ride to the PATH. Since he told me last time he wished I kissed him when he dropped me off, I decided to oblige that request. I gave him a nice smooch before heading into the city to start my workday. I liked M.E., but not enough to make him my boyfriend — Not after what I learned. But, it would be nice to have someone around regularly to share affection and pleasure with on occasion. Maybe this was the start of a beautiful friendship…
Follow @onegayatatimeHalf Day Fun
Posted by One Gay at a Time in Gay Dating on April 12, 2012
Monday at work, I received a email from UPS notifying me a delivery attempt was made. When I arrived home Monday night, I had a notice on my door from UPS. They’d been there earlier in the day and attempted to deliver the leather chair I ordered. No one was home, but luckily the driver gave me his cellphone number so I could call him when I got home. I called him, and he delivered my chair around 7:30 at night. (I love my UPS man!)
I’d already informed work I’d be taking a half-day to accept the chair, so I kept those plans. It would allow me to take care of a few things after my emotional trip to LA.
Since I didn’t have to get up early Tuesday morning for work, I decided to reach out to a guy I’d been chatting with for quite some time on Grindr. I was very apprehensive because he was so young. He is 22 and is still in college. I told him straight up my hang-up with his age. That being said, I still agreed to meet him, but I explained it wasn’t an ideal situation.
When we first talked on Grindr, he was looking mainly for a hookup. He had an amazing body, but I was making an effort to calm down with the hookups. I told him I was looking for something more substantial. He was very interested in this response, but he already showed his cards. I knew he was there more for sex. We agreed to meet up for a drink sometime, and I went to bed.
Tuesday morning, I let my hormones get the better of me. I woke up horny as usual, and I found him on Grindr once again. I asked him if he wanted to come over. The conversation quickly morphed into sexual territory.
We both talked about a few fantasies, and I quickly learned he had an adventurous side. I was very turned on, so I told him to come over. He explained he needed to shower but would be up for coming over. I too showered in anticipation of his arrival.
While we talked about our fantasies, we discussed a little fun when he arrived. I told him how hot it would be if he undressed in the hallway before entering my apartment while I watched through the peek hole. He was more than enthusiastic about this and agreed.
When he arrived at my apartment, I buzzed him in. He came to the door and did exactly as we discussed. I was so incredibly turned on watching from the other side of the door. When he was left in his boxer briefs, he knocked. I let him in and led him to my room. We chatted very short bit before we started making out. He stripped me down to my boxers as well, and we embraced each other while we made out on the bed.
He had a great body — Plenty of muscles and lots of definition. He had the cutest smile as well! Warning: The following may be too graphic for some. This escalated, and the boxers ended up on the floor. I couldn’t keep my hands off him. He was the best looking guy I’d been with in a long time. He was also one of the best kissers I’d been with since I can remember.
Before he came over, we chatted about positions. He told me he usually was a top, but he wanted to bottom for me. He told me he had little experience in the area, but wanted to try it out with me. As things escalated, I whispered in his ear my desires and asked him if I should get a condom and lube. He enthusiastically said yes.
I made sure to take things VERY slow. I was treating him as if he was a virgin — Not my first. It took a little time, but after a short bit, he was very much enjoying himself. I could see waves of goose bumps flowing over his body. It was incredibly sexy. I’d finally found a match for passion in the bedroom. He had the right mix of intimacy and sex, and I was thoroughly enjoying myself.
It became necessary to take a break so he could catch his breath. We talked while he relaxed, mixed in with some more passionate kissing. After some time, we made our way to the edge of the bed and tried a new position, which we both thoroughly enjoyed. It’d been a long time since I was with a man in which I felt our bodies become truly one.
When he had his fill and couldn’t take anymore, we laid next to each other and pleasured ourselves. For once, it didn’t take me too long before I finished. He made a comment about being impressed, but was unable to finish himself. I immediately pegged him as someone who had the same problem I did.
We laid there for some time cuddling. I took a lot of time to take in his smile. It lit up his entire face. He was very cute. He is of a Middle-Eastern decent, which I would never say is my type, but I was really attracted to him.
This guy was one of the few who would be a repeat offender. He too expressed his desire to see each other again as we both got dressed. I was still incredibly turned on watching him stand naked in my room while he put on his clothes. I wasn’t just attracted to him sexually. I could tell he was a special guy. I was attracted to him on an emotional level as well. I just worried about our compatibility. I’ve been out in the workforce for nearly six years now. He still hadn’t even graduated college. I’m not one to discriminate based on age, but I do discriminate on life stage. This would either be a guy who expanded my horizon, or proved my rationale — Only time would tell…
Follow @onegayatatimeLate Night Quickie
Posted by One Gay at a Time in Gay Dating on April 11, 2012
Sunday night in LA, I took quite a blow to my heart. I tried to prepare myself for the inevitable goodbye, but I didn’t get to say goodbye. I’d driven all over LA trying to connect with The Navigator, but he wasn’t responding.
I faced facts and drove to the airport. I had no idea what else to do with my time, so I just drove to the car rental lot and returned my car. I figured I could at least use some time at the airport to blog a bit. I sat int he airport diner and ate my dinner alone.
My flight home was awful. First off, it was a redeye. I was set to land at 6:00am Monday morning. I had to go to work later that day so I tried my best to sleep on the plane. It was also awful because I was crammed in a widow seat towards the back of the plane. My airline status with United got me nowhere. I barely fit in my seat, and I wasn’t able to stretch out and walk around because the two men next to me were sleeping the entire flight.
I managed to sleep for two hours, but woke up after that. I had no feeling in my ring and pinky finger of my left had. Apparently I slept on it funny. When a fair amount of time passed, and I never regained feeling, I became worried. Maybe I had a blood clot or maybe I’d done some nerve damage. I tried to think about other things and distract myself, but I really started to get worried. I took out my laptop and did some more blogging, but even that was a challenge with two numb fingers. I was really starting to worry, but the feeling didn’t return the rest of the flight. (Four weeks and a doctor appointment later, and I finally regained feeling — I had a nerve impingement — Cubital Tunnel Syndrome).
I was exhausted all day at work Monday. I’d only gotten a few hours sleep on the plane and about one hour in my own bed before work. When I got home after work, I was still horny from my rambunctious trip. I was on Grindr, and a cute guy from the city wanted to come over for some fun. I didn’t turn him down since he was hot and said he’d wear his jockstrap.
When he arrived, I realized he was a redhead. He also had a slight Hispanic accent. He was also quite a presence clocking in at 6’4″. He was not born in America, but had been here a majority of his life. He was decent on the eyes, but nothing you’d run to your friends about. When he arrived we went straight to my room. He slowly got undressed and comfortable until we were both laying on the bed, me in my boxer briefs and him in a jockstrap.
Warning: The following may be too graphic for some. I found the jockstrap very sexy. I’ve always been attracted to the athlete types and find locker rooms to be one of the sexiest places. They just turn me on. Always have.The jockstrap really gave him the leg up in my book. He was looking for a hot top, and I agreed to fill the position, literally. I broke out the condoms and lube, and we have a good time. Sometimes it was a little weird and awkward, but sex is never perfect! He really seemed to be enjoying himself. I did as well, but I could already tell this guy was going to linger. He was a gentle spirit. This would be no wham bam thank you man. I was going to have to sit through some pillow talk.
He started talking about his grandmother and how she is sick. He was flying home the following day to see her before she passed away. It wasn’t looking good. I started to feel bad for him, but then my emotions became distracted when he mentioned things like sleeping with her in her hospital bed. He looked like he was ready to cry, but all I could think about was this strange layout in a hospital room. I understood he was close to her, as she was responsible for raising him, but some of the things he was saying with his accent seemed very strange to me. There was obviously a cultural divide.
After we chatted some more, and he asked if he could use my shower. Now he was really pushing it! I obliged the request, but after that, he was gone.
He showered and toweled off. He began to get ready to go home. He talked about getting together again when he got back. He mentioned how heartless a lot of the other guys he’d hung out with were, and how sweet I was. He said how much he liked me. He wanted this to be an ongoing thing of friends with benefits. He told me his real name and that the name he gave me, Keith, was completely made up. Someone was a little paranoid. I felt like I found a stray puppy who wanted to follow me home. There would never be a next time, but I told him to hit me up when he got back from visiting his grandmother. After about three weeks, he did of course text, and I of course did not respond.
Follow @onegayatatimeGym Hottie
Posted by One Gay at a Time in Gay Dating on March 14, 2012
Since my breakup with Smiles, I’ve been making greater efforts to spend more time with friends. I didn’t neglect them while I was dating him, but I certainly didn’t shower them with attention either. They’re very important to me, and I wanted to make sure they knew they were appreciated. Of course, I also just loved hanging out with them, otherwise they wouldn’t be my friends.
One of my old roommates asked me if I wanted to go out to the bar. It’d been a long time since he’d done this. It came quite out of the blue, but I was very happy for the invitation. Since we don’t live together, we get along much better. It wasn’t that we fought all the time while we lived together or anything. It’s just much simpler now. I look forward to bar nights with him.
At the same time, one of the girls who I know from my annual Martha’s Vineyard trips was planning a birthday gathering the same night a block from my office. I asked my old roommate if he minded going there for happy hour. I thought it would make things convenient so I could spend time with both. It’d been a long time since I caught up with both friends.
My old roommate and I arrived at the bar early. We made our way through the crowd at Gingerman to the bar to order some beers. I offered to pick up the first round, as I generally do. I handed him his beer and we cheersed. It was at that moment I learned it was his birthday. I had no idea until he said something. I felt like such a sh*t. He was a close friend, and I was usually up on that sort of thing. I have everyone’s birthday in my phone, so I checked to see how I missed the date. It turned out I didn’t have his birthday in there, but with more investigation, I had scheduled it a month later on the same date. I told him how bad I felt, but also added, “At least I offered to buy the round! Haha.” He laughed and quickly forgave my mistake. I thought about it for a second, and realized I was the only one meeting him for drinks. I was the one he wanted to spend his birthday with. I was touched and happy.
We stood by the door because it was the only place we could stand, drink and have a discussion. He told me his plans to go to Atlantic City that weekend for his birthday with a busload of people. I wished him luck since it sounded like such a complicated situation.
After some time, the birthday girl arrived. She came in and gave me a big hug. I introduced her to my old roommate, and we quickly caught up. She decided to make her way to the back of the bar to see if she could grab a table when the bouncer chased us away from the front door. My old roommate and I had already been back there and knew there were no tables, so I let her find out for herself after telling her that. He and I made our way to the front corner of the bar. Just as we did, a couch opened up. I texted the birthday girl to come join us. About ten minutes later, she finally did and brought the rest of her group over.
I talked with my old roommate as more and more people filtered in. It was becoming an intimate little circle. I introduced him to everyone that joined that I knew. When the evening was dragging on, I decided I was read to head home. I had to take equipment home from work, so I was going to book a car service from my office. I invited my old roommate to join me since he still lives in Hoboken as well, and he accepted. I pointed out how I bought all his drinks and provided him a ride home, proving I wasn’t a bad friend who forgot his birthday after all.
We said goodbye to the birthday girl and the rest of the group. She pulled me aside and told me how cute he was. I explained to her he wasn’t a love interest. I pointed out how she’d met him at my Christmas parties, as well as his girlfriend. She was so confused, but I realized what happened. He was guilty by association. Because he was sitting on the couch with me, and because of my status as a gay man, everyone who knew this bit of information also assumed he was gay as well.
As we walked to the car, I pointed out to him what happened. Even though there was nothing I could have done to prevent it, I apologized to him for it. He was oblivious to it, and he laughed it off.
That night, I also had to say goodbye to another ex-roommate. He was still a good friend and tennis partner. He was moving to San Francisco for work, which meant I would probably see him once a year like my other San Francisco friends. I was very sad to see another friend go. Slowly but surely, all my friends were moving away or pairing up and falling off the face of the earth. I know this is part of getting older, but that doesn’t make it any less painful.
My sister and I went to the bar where he and his friends were gathering. It was nice to get to see him since it had been so long. He’d been quite busy with his new job, but now I’d see even less of him. After I got to chat with him for a bit, I texted my other friends, D and his girlfriend and asked what they were up to. They wanted to meet up for drinks, so we decided to go to Cooper’s Union, where I know the owner and bartender.
We met them there, and the whole lot of us wasn’t charged for a single drink the entire night. He always took great care of me and my friends when he worked at my usual watering hole. Now that he branched off and opened his own bar, the attention only got better.
I had a great time with everyone that night. I got to see so many of my friends. Normally I’m too lazy to do any of these things. I always bail last minute out of selfishness, but I was trying to be better about it. It was already paying off. I had a really great time.
In the middle of all this, a gorgeous man walked into the bar. I’d seen him many times before. I’d actually seen quite a bit of him as well. He was a usual at my favorite bar, and he was a usual at my gym in the city. Apparently we both lived in Hoboken, and we both worked in the same neighborhood. I’d had a crush on him for a looonnnggg time, but had a very strong feeling he was straight. He was still gorgeous and fun to look at.
At the same time, I noticed he caught my sister’s eye as well. It’s ironic, but we have the same taste in men periodically. We both acknowledged shared interest in him, but I pointed out to her it wasn’t even worth a battle. She’d already won. There was almost no question in my mind he was straight “How do you know?” she asked. “I can just tell. But, I can also tell you he looks great with no clothes on — At least from the backside anyway,” I added. We both laughed and she continued to ogle him from afar. I did as well, but I was much more discreet about it.
When I was tired and it was time to go home, I gathered everyone to make our way home. Of course I wasn’t going to walk out without paying. I gathered cash from everyone and handed him a wad of cash before walking out the door.
I had a great night. I saw a lot of my friends in one night, I got to scope out a hottie I’ve had my eye on, and I had cheap drinks. Maybe single life was working out well for me. Maybe it was time I tried that for a while… Maybe not…
Follow @onegayatatimeWelcome Back?
Posted by One Gay at a Time in Gay Dating on March 7, 2012
Sorry for the late post… Had a very busy morning at work…
Since that fateful night on December 31st, 2011, I’ve had my eye on a certain someone. He was also attending the party I went to on New Year’s Eve.
Throughout the night, I talked to him a fair amount. He seemed like a really nice guy. For a solid twenty minutes, he and I were the only ones in the living room until more guests arrived. We got to know each other fairly well. My original thought on him was he was too young, but the more I got to know him, the more I learned how mature he was. Obviously age had nothing to do with maturity. I learned that the hard way with Smiles. I wasn’t going to rule him out just because he was 22. It also helped he was very attractive. He had both the jock look and the intelligent look about him. It was very sexy.
I didn’t want to jump the gun however. I somewhat embarrassed myself that night, and I wasn’t sure if he took notice. I decided to wait until the dust settled, especially since he knew Smiles though a mutual connection, the party’s host. Before my trip to San Francisco, I laid the groundwork. I informed him of my breakup with Smiles on Facebook. He sent his condolences.
Now that I was home, I was ready to dive in and see if I could ask him out on a date. I sent him a Facebook message that Tuesday: “Hey dude. I know this kinda comes out of left field, but I thought you were a pretty down-to-earth guy when I talked to you on NYE. I was wondering if you’d be interested in grabbing a drink sometime…?” I don’t know why, but I felt very vulnerable doing this. It’s crazy. He’s five years younger than me. Why was I so intimidated? All I could do was wait for an answer.
That night, he finally responded: “I am flattered, but I am kinda seeing someone. Happened right after New Years actually. Doesn’t mean we can’t chill as friends.” My hopes were dashed. I’d been plotting and planning this whole thing out over time to find out I missed the boat. I was kicking myself, but there was nothing I could do. It is what it is.
I needed to graciously respond, and secretly hoped I could meet him as friends, and he would realize how much of a catch I am. Maybe he’d let things fizzle out with the other guy. The door wasn’t closed, even though it was beginning to shut. There was still a glimmer of light — A glimmer of hope.
“All the good ones are… haha… but yes.. Chill as friends works for me too. Always lookin’ for friends as well. Shoot me your #, and maybe we can find a time to hang/grab a drink…” I responded.
Sadly, I wouldn’t hear back from him again. Three weeks later, I tried to see if he would be interested in meeting up, but I got no response. If he was truly interested, he would have responded. I was learning to stop pursuing men who didn’t return an interest in me. It never worked out in my favor, and it just caused me greater frustration. If there were interested, they’d be as excited as I was to message/call/text. It wouldn’t matter about waiting two days before calling. If someone is interested, they won’t care about any of that. They’ll just be thrilled you connected at all.
I was beginning to feel very disappointed and lonely. I had no promising prospects on the horizon. As time goes on, this dating thing is getting harder and harder. Everyone thinks gay dating in New York City is a cinch but far from it. It is so incredibly hard to date in this city. The gay men here certainly don’t do anything to make it any easier.
Warning: The following may be too graphic for some. In the meantime, I was back on local Grindr. I found a guy who lived very close to my apartment who wanted to be dominated and wanted to muscle worship me. I hardly think I’m the muscle worship worthy type, but if that was what he wanted, why not give it to him. I went over to his apartment. He was a bit awkward, but I wasn’t there to find love. I was simply there to satisfy a primal need. I thought I would be able to play the part. I thought I could say all the things a dominant top would say, but in the end, I think I sounded ridiculous. It’s not who I am. It wasn’t awful, but I don’t think either of us were getting out of it what we thought we would. It took me a long time to finish with him, as usual, which didn’t exactly make for a smooth evening. When I did, it was worth his wait. However, because of the nature of my climaxes, he had to run to the kitchen and grab a bottle of Resolve and a paper towel to clean up a spot on the carpet when I overshot his chest.
He came back to the bed and we laid next to each other chatting a bit. I learned he knew the other awkward hookup I had in the same building. Apparently they were friends. I specifically asked him not to mention me, which of course spurred a whole new line of questions. I knew this was going to come back to bite me in the a$s. It was only a matter of time before the 40 year-old started messaging me again.
With that, I got dressed and made my way home on my walk of shame. Luckily it was cold out and it helped me clear my head. What was I doing? This isn’t me. This isn’t what I’m looking for. Why am I doing this? Yes, we all have needs, but I should be putting more energy into finding the right guy instead of Mr. Right Now.
I thought about all the other guys floating around out there on my roster. Was it even worth it to revisit with long-time online friend after our failed date? Maybe the southern boy I was chatting with would finally find the time to meet up. The guy who came back on the roster after almost a year was still a possibility. I needed to plan drinks with him. My Asian neighbor friend from Grindr was still asking me to grab dinner sometime, but he doesn’t drink, so I didn’t see us being very compatible. There was the very sexy, very compatible guy I found on Adam, but he wasn’t responding to any of my messages anymore. I needed to cut him from the list.
I needed to get back in shape and concentrate on building a better me. Ironically enough, I was hitting the gym regularly again. For so unknown reason, I was looking for N there every time I went. I don’t know why, but something inside me wanted to see him there, even though I wanted nothing to do with him. I needed not only to close that chapter, but also to toss the book to someone else and forget about it.
I was spinning my wheels. I was constantly Grindring, and it was getting me nowhere. I was still feeling a little angry for letting Smiles take advantage of me. I thought back to all my relationships and realized how each of them let me down. N, San Francisco, Smiles… I didn’t need any of them anymore. They brought nothing positive to my life. It was time to drop that baggage. The only one I wanted to keep around was Broadway. Since we’ve broken up, we’ve managed to remain friends. I turn to him for advice, and he is always there for me. He’s a good friend and I truly appreciate him. I can’t understand why they all couldn’t be that way. I’m thrilled we’re still friends and want that with all my exs, but if they weren’t going to make that possible, so be it.
I needed to get to a better place. I wasn’t in a dark place, but I was certainly stuck in this constant gray area. I was walking around in a cloud. I was wasting my life away searching for a guy in all the wrong places. If I wasn’t happy, I wasn’t going to find anyone. I just needed to figure out how to change things. It wasn’t going to be easy…
Follow @onegayatatimeThe Horror!
Posted by One Gay at a Time in Gay Dating on February 28, 2012
Touchdown! After a long flight of writing a lot of blog entries, I finally landed in San Francisco. I was very happy to be away from New York. This was forced time to clear my head. It would be impossible to try to find a guy for a date from thousands of miles away, and I needed a break. Don’t get me wrong, I want a man to call my own, but the process of finding one is exhausting.
I rode to my hotel with a very chatty driver. He had lots of questions and comments for me. Many of the comments referred to women and our “shared” desire for them. I didn’t have the heart to tell him I was gay. I just let him continue talking. It wasn’t that long of a ride.
I got to my hotel, and took my good ol’ time getting to the office. They didn’t know exactly what time I landed, and I’m sure they wouldn’t have any work for me yet anyway.
I was right. When I arrived at the office, they had no work for me the entire afternoon. This worked out quite well. It allowed me to update the blog and go for a nice long delicious lunch I didn’t have to pay for. When the workday was coming to a close, I made my way back to my hotel.
I’d been on Grindr all day hunting for a guy to either meet for a drink or have some fun with. Nothing was turning up. I recalled the last time I was out there. Originally, I had the same luck. That is, until I picked up signal from San Francisco. No such luck that day.
I thought about the other weapon in my arsenal. I could pull up adam4adam.com and see who was in the area. I managed to find a few sexy men to message. It was only a matter of time before one of them messaged me back. A few did, but many of them were flakes. A few of them were unattractive as soon as I saw their faces as well. I asked a few to hang out, and the ones only interested in sex, I proposed coming to my hotel. Some of the guys on Grindr offered bl*wjobs, but I was looking to get it in.
One guy was very willing to make the journey to my hotel, and he was a bottom and looked pretty sexy. I told him to come by and gave him the details. I had one failsafe. They would not be able to come up to my room without me picking them up from the lobby. If I was unsatisfied with what showed up, I could hop back in the elevator and shut the door. That’s terrible, I know, but you never know what will show up when push comes to shove.
I was doing it again. I ended a relationship and simply fell back into old habits of hooking up outside of a relationship. I wasn’t thrilled with myself, but I was giving myself a free pass while in San Francisco.
I would have to put off dinner until after my evening tryst arrived. I was hungry, but I wouldn’t have time to get dinner before he came by. When he arrived, I collected the man from the lobby. He was a good-looking Aussie.
We got up to my room and talked about where we were from and our stories. He sat on the bed and talked with me. He seemed like a pretty cool guy. He was a bit of a vagabond. I liked his traveling experience. I was envious of it.
When the moment was right, we both went in for a kiss. This was followed by LOTS of kissing. Lots! He seemed quite nervous. I was trying to get him to relax a bit. I took my time with him gently feeling his body. He was a good kisser. This was a good sign.
Slowly I began peeling off some of the many layers he was wearing until we were both naked. He had a decent body. He was skinny, but not exactly muscular and defined. The kissing became more passionate and the petting grew heavier. When we were pretty far along, I whispered in his ear, “I want to be inside you.” He responded the same sentiment, so I reached for the condom and lube I had in the nightstand drawer.
Warning: The following may be too graphic for some. Now I know I say this in a lot of posts, but this time, it may be too graphic for even those who are normally turned on by my warnings. Just be forewarned. Don’t say I didn’t tell you so!
I inserted myself inside him. He felt great. He seemed to really be enjoying himself as well. We were about two minutes in when something didn’t feel quite right. I took a whiff of the air, and immediately knew what was wrong. I looked down in horror, and it was all I could do to keep myself from vomiting all over this man.
I immediately pulled out and hustled to the bathroom. We both knew what was wrong. I tossed the condom in the trash and began scrubbing myself. I casually suggested a shower. I was trying to maintain my composure so this man wouldn’t feel worse than he already did. This was horrific, but I still had the man’s ego in the back of my mind.
He suggested I go first. I’m not sure why. All I could think about was his uncomfortable state while I showered. He made his way to the toilet and took care of himself while I washed up in the shower. When I finished, I left the bathroom so he could do whatever he needed to do.
I was still a little shaky and trying not to think about what just happened. I’d encountered this before, but never to this extent.
When he emerged from the bathroom, you could have knocked me over with a feather. He actually suggested we keep going. I was speechless. I didn’t know what to say. At this point, I no longer had the man’s feelings in mind but only my own sanity. I told him, “No. I think I’m done for the night.” He didn’t stop apologizing. “Don’t worry about it. It happens. Part of the territory,” I reassured him while he got dressed.
And then, when I didn’t think this man could surprise me any more than he already did, he suggested we grab food since he hadn’t eaten anything yet either. “No. I think I’m just going to order room service or something but thanks,” I added.
Just as he was walking out the door, my phone rang. It was San Francisco. I explained to my departing guest that I needed to take the call and gave him a wave goodbye. I couldn’t wait for him to be out of my sight so I could stop thinking about what happened.
“Helloooooo. How are you? Are you Grindring?” he said as I picked up the phone. All I could think in the back of my head was, if you only knew! I simply replied, “I’m single. I can do whatever I want.” We talked about our schedules for the week and planned a night we could grab a drink together. He suggested we meet in The Castro since I didn’t make it up there during my last visit. Once our plans were solidified, I hung up and tried to figure out what to do for dinner.
Joe’s Crab Shack was a block away and was one of the few places still open at that hour. I decided to go there. This would be the second mistake of the night, as this was the worst seafood I’d ever had. I couldn’t finish it. I was literally wiping the seasoning off the crab legs with paper towels, and I still could barely tolerate them.
If this was a sign of what was to come from my San Francisco trip, I was going to lock myself in my hotel room when I wasn’t at work. The positive was, it certainly couldn’t get much worse…
Follow @onegayatatimePlaying It Cool
Posted by One Gay at a Time in Gay Dating on November 21, 2011
My weekend with Smiles was a decent one. I’m not self-destructive, nor do I get in my own way enough to think it was a failure or a bad weekend. Any time I spendt with him was progress, and it made me happy. But, I left the weekend feeling a little uneasy. I was denied twice in two days. Did he not find me attractive? Was he just thinking of me as a friend? Not knowing where I stood was eating away at me.
It’s obvious he was interested in me. But, it was his level of interest that worried me. We were in the beginnings of a budding relationship, or so I hoped. Things were supposed to be carefree and fun. The heavy stuff comes later. We should have been having sex like rabbits and dying to see each other.
I felt like I was constantly chasing after him. I got no indication he was interested in chasing me. But, maybe I wasn’t giving him the opportunity. Maybe I got so excited about him, I was constantly initiating our time together, and if given the chance, he would be asking me out on dates.
On Monday evening I texted him to see if I could spice things up with a little getaway. “Hey. What would you say to getting out of the city for a weekend?… Celebrate your birthday, just the 2 of us… Something totally low-key and relaxing like New Paltz, NY. Gorgeous this time of year too and not that far…” I thought if we hit up a bed and breakfast, we could find the time to get wrapped up in each other with no other distractions.
A big part of me thought this was a giant leap forward, and I was moving too soon, but another part of me noticed a little bit of stagnation. Things were getting a little stale. Maybe I needed to intervene to get us to that happy-go-lucky mindset.
Just as I expected, he safely replied, “Hmmm that sounds like fun, can I think on that one for a min? I’d want to be able to give you my full attention and I think with [work] this weekend, the [possibility of a new prospective work project] starting and the over two jobs with a bit of clock on them, I might not be totally present. Which wouldn’t be fair.”
I was right. Too soon, too fast. I didn’t want to cower and backtrack. I had to play it cool. “Certainly. Wasn’t exactly talking about this weekend. Was more thinking 3+ weekend out. Just wanted to throw it out on your radar,” I replied. I wasn’t lying. I was really just planning in advance.
He got my drift. I soon got a text back: “Ah. Ok. Sleep well. I’m crashing early tonight for a change.”
I decided to take some advice from friends and play a little hard to get. I stopped texting or calling. The next point of contact was going to be initiated by him. It killed me. I wanted to text so bad. I never went anywhere without my phone, waiting for him to text or call.
Tuesday went by without a word. I was in a bad place. I started having doubts about the whole thing. We were only a couple of weeks in, and he already grew tired of me. These weren’t good signs, and I started to really get down about it.
I decided, I wasn’t going to put myself back out there completely, but I was going to continue to put my ear to the ground to see what was going on out there. I started answering my messaged on OKCupid and chatting with a few guys. It was nothing crossing the line, but in a way, I was laying some groundwork if Smiles decided he was done with me.
Finally, on Wednesday, he texted me to ask me how my day was going. The exchange went back and forth a bit before simmering out. I was thrilled — Back on top. I recognized how happy I was, but I also recognized how dependent I am on others for my own happiness. This is an issue. I really need to learn to be more independent. It’s not healthy to need other people to that extent.
In our exchange, he invited me to come with him to a bar to watch a friend’s band the following night. I reminded him I had volleyball on Thursdays and couldn’t go. I really wanted to go, but another part of me was happy I had to turn him down. I have a tendency to drop everything for men I’m interested in. I needed to show I was independent as well.
Thursday went by, and we didn’t talk to each other during the day. On my way to volleyball, I texted him: “Thinkin’ bout you 🙂 .” He responded, “Good luck at your game!” It was nice he remembered I had a game. He was showing a vested interest in my life, which is always a good sign.
After volleyball, we texted a bit. He told me about how he didn’t get the project he was counting on for work. I knew it meant a lot to him, so I tried to console him as best I could. I knew he would be depressed for a few days as a result because he was really looking forward to it. I called him, and we spoke on the phone. I also took the opportunity to ask if I would get to see him Friday night.
Since he asked me to watch the band with him, I was satisfied he wanted to spend time with me, and I knew it wasn’t simply me chasing him down.
He had plans to go to a friend’s birthday party Friday night and talked about us going together as if we planned this long ago, and it was assumed I would be attending with him.
It appeared things were back on the upswing, at least emotionally for me. The question remained. Would we continue moving up, or was it only a matter of time before things started sinking again?…
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.
At 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 
Finally, Someone Who Knows What They’re Doing!
Posted by One Gay at a Time in Gay Dating on March 2, 2012
So far my trip was turning out to be a flop. I had on traumatic experience and an ex who tried convince me to have sex. I needed my luck to turn around.
I was hoping I would finally get to live out my fantasy. I made plans with him to grab a drink Thursday night after work. He asked if I’d like to meet in The Castro, but I asked if he wouldn’t mind coming to my neighborhood in the Wharf since I trekked up there the previous night. He agreed, and I asked the concierge for a good spot to grab a drink and chat with someone. He gave me a great spot to check out two blocks away — Parlor. It was perfect. We could easily head back to my hotel room after a few drinks.
While I waited for him to get ready, I excited myself with some porn. I wanted my libido revved when I met him because I wanted to live out my fantasy completely.
When he was nearby, I made my way to the bar. There weren’t many people there. It was perfect. Good music, but quiet enough for us to chat.
We sat and talked for hours. He’d been seeing a therapist over the past few months, and he’d really been having some breakthroughs. He has a tough time with his family as they’re not accepting of his lifestyle “choices.” I told him my coming out story, and he was very happy I for me that I had such a supporting family.
Three beers later for each of us, and the conversation was going strong. Our conversation hit the pause button when we both heard someone at the other end of the bar making a gay comment, not in reference to us in the slightest. Our ears perked up ready to be on the offensive but there was no need. When we finished our fourth round, I asked him if he would like to come back to my hotel room. He accepted my invitation, but said he couldn’t stay too long since he had to work early the next day.
Warning: The following may be too graphic for some. One by one I peeled off his clothes until he was naked. I took it all in with a big grin on my face. From the first time I laid eyes on his “big swinging d*ck” as I called it, I couldn’t wait to get my hands on it. It was beautiful, and I sure as hell had some fun with it.
He immediately went for mine and started orally pleasing me, front and backside. He was very good, but also very loud, moaning as his head bobbed up and down. This wasn’t something I was used to. I wanted to finish for him. I wanted to show him the fireworks I could set off, but I just couldn’t concentrate. After some time passed, I went to return the favor, but he stopped me. He told me he had to go because he had to be at work early the next morning.
I was so disappointed. He was really good in bed, and I needed that. I also had been looking forward to that for years now. But, I completely understood. Around midnight, he got dressed to head home. As he was leaving, he told me how great I tasted and how he wasn’t going to wash his hands or face for days. This was very dirty and very sexy. I’d never had anyone respond to my body that way before. He kept coming back for more as he made his way to the door. I could tell he didn’t want to leave, which made me happy. I was also purposely teasing him with my body, as I lay naked on the bed. I didn’t want him to go, but I still had one more night in San Francisco, which means I had one more chance to take him to bed…
Follow @onegayatatimeRate this:
amazing lips, bar, breakthroughs, Coming Out, concentrate, concierge, conversation, Date, Dating, dirty, disappointed, drinking, family, fantasy, finish, fireworks, fooled around, Friendship, Gay, gay comment, Gay dating, gay sex, gentleman, great body, great guy, grin, heart, Hoboken, Homosexual, Hooking Up, hotel room, hugs, incredibly sexy, invitation, kiss, libido, lifestyle choice, load, love, luck, manroulette.com, moaning, music, naked, neighborhood, New York, New York City, not accepting, offensive, orally pleasing, Parlor, porn, real thing, relationship, San Francisco, Sex, sexy, skype, spectacular kisser, story, supporting, tasted, Texas, texting, The Castro, therapist, traumatic experience, trip, Wharf, wine, work, yearn
2 Comments