Posts Tagged hookup
Is Something Bothering You?
Posted by One Gay at a Time in Gay Dating on June 8, 2012
That Tuesday, I woke to the sound of my alarm. I was going to go for a run, but the sound of my alarm wasn’t all I heard. It was raining outside. I turned off the alarm and looked out the window to see rain pouring down. I checked my phone to see if CK texted, but he hadn’t. Who knew what happened? I sure didn’t.
I wanted to text him when I got to work, but I decided against it. He knew where I was. He was the one who suggested plans that evening. He would be the one to hit me up and clue me in on those plans.
Finally, around noon I got a text: “Hey sexy.” I didn’t see it until a little later. I responded, “Hey. How was the rest of your night?” Apparently he’d gotten tipsy at the work event he called me from. He went home and passed out in all his clothes including his shoes. When he woke at 4:00am, he properly put himself to bed. The he apologized for not calling me back and asked how my night was. I mentioned my cancelled run, and he expressed interest in going for an early run with me sometime. Tthat would be the only way he’d do it since he’s not a morning person. I told him we’d both just stay in bed because I’d just be tempted to lie there with him.
I then asked him if we were still on for that night. “I’m game. What’s the plan?” he responded. I reminded him he set the plans, and I was waiting for the details. He decided he’d rather stay away from alcohol, and I asked what he wanted to do instead. He was eating his lunch, so he asked if he could get back to me later. 5:00 rolled around, and I still hadn’t heard back from him. I certainly wasn’t feeling very special anymore. That’s when the phone rang. I was heading into a meeting, so I sent him a text. When my meeting ended, I called him but got no answer. At 6:00, I finally got a call back. He was heading home and wanted a quiet night in with me. I wasn’t opposed, but I wasn’t thrilled either. I was beginning to wonder if it was all about sex with him. He needed time to straighten up his apartment, so I made my way over there around 7:00.
When I got to his apartment, I stood in the hall waiting for quite some time before he answered the door. I hadn’t called to tell him I’d arrived. A small part of me was surprising him on purpose. He just happened to be getting out of the shower.
He greeted me with a giant hug and a big kiss. I removed my shoes and got comfortable. He finished toweling off and joined me on the bed. We cuddled a bit until he asked me if everything was alright. I lied and said everything was fine. He pointed out I seemed short in my text messages. Big kudos to him for noticing the subtleties in my mood. We continued to hug until we discussed what we wanted to do for the evening. He mentioned watching the sunset, and I told him that’s exactly where my head was.
I had ulterior motives. When we got to the roof, I would find the appropriate time to bring up my concerns that arose since Sunday. He also asked if I wanted to smoke, and I shook my head yes. “Are you sure everything is cool?” he added. I told him I was short in my texts cause I was actually working all-day and apologized. I didn’t really think I was being all that short. We smoked and finally made our way up to the roof about a half hour later, Coronas in hand.
When we got to the roof, we continued snuggling on the outdoor couch. We talked about the surrounding buildings in an “I’m high” kinda way. The conversation never really had any direction. Then again, he brought up my mood and asked if everything was alright. I didn’t think I was being that obvious with him, but I also wasn’t being myself. That’s for sure. I didn’t know how to let myself be free with him anymore. I started to close myself off to ensure I wouldn’t get hurt. I was shoving distance in there with both fists.
I finally told him how I was feeling. I explained how I thought his sentiments came out of nowhere on Sunday. I told him I thought it was a bit early to have that conversation, but now that it’s been had, a few issues were brought to top of mind. I addressed my feelings regarding him being on Grindr and how that made me feel. I told him I felt as if I wasn’t enough for him. I told him I didn’t need to be on there, and while I wouldn’t dictate to him to not be as well, I just didn’t understand why he felt he needed to still explore it.
I was having a hard time expressing my feelings, but I think I got the point across eventually. I told him because of what he told me, I was afraid of getting hurt. I wasn’t able to be myself and give him the real me if I felt vulnerable to pain. I wanted to be myself with him. I wanted to give him the real me. I needed to feel safer than I did. “Since meeting you, you’ve made me feel incredibly special. Since you told me what you did on Sunday, I no longer felt special,” I told him.
He looked a bit shocked. “The last thing I want to do is make you worried or scare you. What I said to you on Sunday was not calculated. It was just how I felt at the time. You are incredibly special, and that hasn’t changed. You are… an aspirational boyfriend. I’d be insane to do anything to lose you. Baby, I think you’re incredible. Part of me knows how amazing you are and wants to dive in full force, but another part of me wonders if I still want my freedom. I’ve already started thinking of you less as something to schedule in my life and more as just part of my life.”
I wasn’t expecting him to tell me he wouldn’t hook up with other guys and tell me we were exclusive. I think I just needed him to know how I felt and where my head was. I could see in his eyes that he understood what was in front of him. I would still be patient and let him figure it out on his own. I just wasn’t going to find myself in another Smiles relationship. He needed to know that eventually the Grindr would have to go, or I would have to go. He needed to know that I wanted a boyfriend and not a friend with benefits. I needed to hear from him I wasn’t just a hookup cuddle buddy. I needed to know I was different from the other guys he slept with from Grindr.
We kissed and embraced. I felt a lot better. It was really starting to weigh me down. I think I handled it very well to suit my needs. A large part of me wanted to ignore the conversation we had in the Sonic parking lot. The other part of me, my constantly overactive brain, wanted me to get some closure on the topic. I think I found the sweet spot.
Warning: The following may be too graphic for some. After kissing and embracing, he began to get a bit frisky. He started to undo my pants. There was high risk here. We were in plain sight of the doorway leading to downstairs. One neighbor had already come up to the roof once to smoke. He began blowing me, always keeping one ear out for signal of someone approaching. I undid his pants and began pleasuring his endowment with my hand. Finally, paranoia got to him, and he suggested we move to the far corner of the roof, out of sight of the door.
When we got over there, he pulled my pants down to my ankles and did the same with his. He was pleasuring himself while going down on me. He edged me many times, getting quite close to making me finish. I was picturing my seed all over his chest, just as he wanted it. Alas, I wasn’t able to fulfill his wish. I came close many times, but just couldn’t get over the hump. He stood and suggested we move downstairs. We got dressed and made our way downstairs. I was incapacitated and had a hard time descending the stairs. My legs were jello from the full-body orgasm he gave me. I may not have had the release, but I still received all the pleasure. He laughed at my struggle.
As we walked down the stairs, I realized he had a slight exhibitionist streak in him. The stunt on the roof, sex with the blinds always open… I had a bit of this in me, but in smaller quantity. He was expanding my comfort zone.
When we got downstairs, the fooling around continued until we took a break to order Thai food. It was 10:30. Once that was taken care of, we had sex. I had the first chance on top, and then we swapped. It wasn’t long before he finished all over my back. He was out of breath and in a daze from how amazing it was. I knew I was having a blast, but I was thrilled our time in bed was so enjoyable for him.
Like clockwork, the food arrived. We settled into bed and ate while we watched Smash. I convinced him he needed to see the show so I could talk to him about it. He really enjoyed it, so much so we watched two episodes, eventually switching to dessert. I passed out half way through the second episode. When it was over, we turned out all the lights and went to sleep. I was happy to have the weight off my back after telling him my concerns. I felt comfortable with him once again. I fell asleep with an amazing man in my arms and a smile across my face from ear to ear.
Follow @onegayatatimeSticking to the Plan
Posted by One Gay at a Time in Gay Dating on May 4, 2012
I had a Friday to myself, and I wasted it on hookups. I could have been doing something productive like going to the gym or grocery shopping, but instead, I spent the day inside trying to line up sex.
There was one man in particular who I’d exchanged messages with on adam4adam.com. He was a well-built guy with a sexy body. He had a nice amount of body hair, great muscles and a spectacular behind. We’d talked about hooking up a few times, but we’d never seemed to line our schedules up. I messaged him, but he didn’t respond.
I continued to search for other guys on the computer when he finally responded. He didn’t read my message until it was too late. We exchanged phone numbers, and he called and told me he had a lot of errands to run before his mother’s birthday the following day. He wasn’t able to see me until later, but suggested we Skype in the meantime. I had nothing to do, so I agreed.
He was even good-looking with bed head on the computer. I couldn’t imagine how sexy he was in person. Seeing him on the computer was just making me hornier, if that’s even possible. I tried so hard to convince him to come by before his errands and do them later. All he needed to do was time-shift his day. He kept telling me the only way it would work is if I came to his apartment. I couldn’t because it was raining, and I don’t ride the motorcycle in the rain. We pushed back and forth for some time to no avail. Of course there was some teasing with body parts on camera while all this was going on. I couldn’t wait to feel his sexy body. Alas, he had to go, so I said goodbye and we made tentative plans for later. I told him when I came by, he’d certainly have to wear his jockstrap for me. He gave me a disclaimer. He was up for almost anything, but he was not up for full penetration the first time meeting me. I was a little disappointed, but understandable.
That’s when I turned to the Mexican guy in the previous post. He was willing to come by right then, and I needed a release. I had immediate regret after that encounter.
Later in the day, my old roommate texted and asked if I was interested in meeting up for happy hour. After being cooped up in my apartment all day, I thought that sounded like a spectacular idea. No one ever invites me out for drinks either. It’s usually me doing the inviting, so it was a special treat. I texted the burly man from my morning Skype session to tell him I’d have to postpone. He called immediately protesting. I told him other things came up, and I wouldn’t be able to come by. He didn’t stop persisting to try to persuade me otherwise. I told him he could have solved the whole thing had he come by earlier in the day.
The clock reached 6:00, and I hadn’t heard from my old roommate. I reached out to burly man to see if he was still available. Indeed he was. I agreed to come to his place a few miles from my apartment. He told me he would be waiting for me in bed wearing nothing but a jock and would leave the door unlocked for me to just walk in.
I drove over there and texted him when I got to his neighborhood. I tried the door, but it was locked. I called him to tell him, and he said his upstairs renter must have left and locked the door behind him. He told me to back away so he could unlock the door. I did as I was told and gave him a minute to get back to his bed.
Warning: The following may be too graphic for some. I came in, undressed down to my boxer briefs and began kissing his back while pressing my body against his. It was as great as I imagined. His a$$ looked incredible in that jockstrap! I could barely resist him. We had a lot of fun together. There was a lot of groping, heavy petting, kissing, sucking, licking, biting, rubbing, etc. It was great. I was really enjoying the jockstrap as well. I was grinding on his backside, almost penetrating him, but never fully entering him. He really enjoyed it and was pushing me further, but in the end, he stopped himself.
He was begging for me to finish, and he brought me to the edge many times. He started orally pleasuring me. He thoroughly enjoyed this, and it was turning me on since he was enjoying it so much. Eventually, I finished in his mouth and all over my abdomen, and he loved it. He began to use his hand to pleasure himself. I helped by applying pressure to different areas until he finished all over his abdomen. We’d chatted about how each of us shoots on Skype, and it was interesting how different and how similar we were. His description was pretty spot on for what actually happened.
We both just laid there a minute and enjoyed the feeling pulsing through our bodies. I still couldn’t get over how amazing his a$$ was. I wanted to penetrate him so bad, but I knew that would have to wait for another day. He hopped out of bed and handed me a towel to clean up. While I stood there, I met two of his cats. They were very cool. This guy was quite into animals. He had a huge saltwater fish tank as well. He ran to the restroom while I got dressed. I also took the opportunity to snap two pictures. He came back and got dressed as well.
He walked me outside and chatted a bit while he smoked a cigarette. He didn’t live in the best of neighborhoods. An old woman so strung out on something walked by, and he engaged her in conversation for quite some time before finally offering her one of his cigarettes and sending her on her way. He told me about how his mother lived next door and his family’s ties with the city. He was a really nice guy. I could see myself seeing this guy again some time. He told me he was also kinda seeing some guy, but it was very casual and nothing serious. He mentioned the desire to see me again sometime, but we didn’t set up anything concrete.
I sped off on the motorcycle back home to shower and get ready to go out and meet up with friends. The only friend interested in going out was P. We agreed to hit up one of my favorite local spots where I know the owner, and he takes good care of me, Cooper’s Union in Hoboken. We had a relaxing night drinking and sitting at the bar. I told her about how I was getting out of control, and it was then I decided I was going on a Grindr diet. This had gone on far too long. I was realistic enough to know I couldn’t quit it cold turkey, but I also knew it was a great temptation for me. I was going to try to steer clear. I would only go on to see if someone messaged me. I would no longer cast out a net and would no longer have it running on my phone all day. I needed a break. I was addicted, and it was time for me to ween myself off the drug…
Follow @onegayatatimeA Colombian Night
Posted by One Gay at a Time in Gay Dating on April 23, 2012
After a very nice date Wednesday, I was pretty happy. It had been a while since I had a good first date. I spent a lot of time having strings of bad first dates or finding guys to simply have fun with and send on their way. Nothing was fulfilling, but for the first time since PR, I was hopeful.
Thursday nights are always my volleyball nights. It’s the one night of the week I get to fulfill my competitive edge and work out some of the frustrations that have built up over the week. I always look forward to it, and I almost always commence the night at my favorite watering hole, McSwiggans.
Before riding home on the motorcycle from volleyball, I checked Grindr to see if I had any messages. A few started flowing in as soon as I opened the application. Where I play volleyball is a hotbed for Hispanic Grindrs and it seems they flock to me like a moth to the flame.
When I got home, I started chatting with one guy who seemed nice enough. When I told him where I lived, he was confused why I showed up so much closer. I explained to him why I was in his neighborhood. He was disappointed to hear I’d already left the area. “We could have grabbed a drink or something.” I told him it wouldn’t have worked out since I had the motorcycle and was disgusting from playing three games.
I did, however, invite him to come to Hoboken and join my friends and I at the bar. I had already texted a few friends and told them to meet me there. Two of my friends were already in the process of getting ready to meet me.
He entertained the idea for a few minutes before finally accepting my offer and dragging his roommate along for the ride. I was going into this arrangement mainly thinking this would be a friendly drink. I made it clear I had friends with me so he wouldn’t think I was asking him out on a date.
I arrived at the bar at the same time my friends did. We grabbed beers and sat at one of the tables. I informed both my friends a guy and his roommate would be coming by to hang out. My male friend looked very leery, but I told him this was just a friendly drink thing. I think he was worried he was basically going to sit through one of my dates. After some time passed, my Hispanic Grindr friend and I started texting. He arrived and was sitting at the bar. I had walked up and ordered right next to him without noticing him there.
I immediately walked over and said hi to him and his roommate and introduced myself. I called my two friends over to introduce them as well.
It wasn’t long before my male friend’s comfort level dropped, and he decided to meet other friends at another bar. My female friend, P, was hitting it off with the guy I met through Grindr. They are both Colombian and were sharing a few stories. The other guys seemed very nice and decently cool. We started with the small talk and then got into more of a discussion. It was nice, but I wasn’t really attracted to this guy at all. This was purely going to be a friendly drink. We talked for at least another hour, and more than a few rounds later, we decided to head out.
He was a really nice guy, and we all left at the same time. P lived uptown and in the direction they were heading to go home, so they offered to give her a ride home. They were parked in the direction of my apartment, so I agreed to walk them to their car at the least before heading home. As we got closer, the convinced me to hop in and let them drop me off. I finally agreed.
When we got to my apartment, it was slightly awkward because I could tell this guy wanted a moment alone with me. Maybe he wanted a kiss out of the night. I don’t know. I reached up and tapped his shoulder and said, “Thanks for coming down here. It was fun. We should connect again sometime soon.” He smiled and agreed. It was my subtle way of letting him down easy without getting his hopes up for a “date.”
Finally, I was making gay friends without overcomplicating things with hookups or sex. I needed to do more of this. I had one local gay friend, and he was all but married with a serious boyfriend, an apartment, a shared dog and a shared car. This was something I looked forward to, but maybe I needed to find a wingman to help me find the right guy first.
Follow @onegayatatimeWinding Down
Posted by One Gay at a Time in Gay Dating on April 17, 2012
Although things didn’t exactly end the way I would have hoped, I had a really great time with my new uptown Grindr friend. He was a very down-to-earth, sexy man whose body I found irresistible.
I made my way home on my motorcycle only to find my apartment full of my friends and my roommates’ friends. They apparently noticed my Irish exit, but I was shocked to find none of them texted me to find out where I’d gone. They didn’t seem to care much. They were all drunk and about to smoke.
I put my helmet in my room and joined in the fun. D pulled me aside and asked if I’d gone to hook up, and I didn’t lie. I nodded my head in agreement, and he said, “I knew it!” with a smile.
My roommate immediately mentioned breaking my glass planter that sits in the window, but failed to apologize for the act. She simply pushed it into a pile, plants and all, and left it there on the floor. After sitting in the room a solid ten minutes, my friend K announces, “Where’s [One Gay At A Time]?” I responded, “Really K! How many have you had!?” We all laughed.
The previous night, I talked to a guy on OKCupid who was quite an athlete. He seemed like a really fun guy, and I was anxious to meet him. We’d emailed a few times back and forth, and I learned he would be coming to Hoboken for the festivities in the evening. Ironically enough, he would be in the apartment across the street. The same apartment my roommate and I scoped out on numerous occasions, noticing a gay couple lives there. I texted him to see if he was there, but he told me he decided to stay home after not feeling well.
This, of course turned my attention to the apartment across the way. My roommate and I had scoped out this apartment many times starting on New Year’s Eve when we presumed two mo’s lived there. This night, they were having a party. We noticed many men, and we tried to make a sign with a sharpie and the inside of a paper bag. It was no use. Anyone’s attention that was looking out the window was drawn to our neighbors upstairs. They too were having a raucous party.
I decided to use technology to find a way to make friends with the mo’s across the street. I pulled up Grindr and tried to find anyone very close. When I finally got in touch with someone nearby and asked him if they were at that address, I came to learn that person had left the party already. I made many more futile attempts to reach out to the party. A few of us watched with curiosity when people moved into the bedroom, but nothing exciting happened. Our front window became a version of “Rear Window.”
When I grew tired of my new entertainment, I made my way to bed. It was a long day, but a fun day. I was beat.
The next day, I returned the favor of a friend for helping me move. I rode my motorcycle over to his new apartment and dug in moving bags and boxes. When we drove to his old place, I realized we were in the same neighborhood as Indiana Jones lived. I pulled out my phone and texted him to see if he was around. It’d been months since I last saw him, and I was anxious to see him again. We were due for a catch-up. I didn’t hear back from him that day, but I wouldn’t give up at that.
Follow @onegayatatimeWhere’d He Go?
Posted by One Gay at a Time in Gay Dating on April 16, 2012
FraI already started my morning off with a little frisky visit and some well appreciated service. It was time to join the real festivities.
I walked out into my kitchen to find my roommate with all her college friends and my other roommate with his girlfriend. I thought I pulled a fast one on all of them sneaking my visitor in the back door, but I was wrong. My male roommate saw him come in. He and his girlfriend questioned me on it, and I was completely honest with what happened. They were fascinated by how transactional it was. They couldn’t believe it, and his girl gave me a high-five.
I celebrated myself with a nice cold beer from the fridge. It was already 1:00 and I was well behind the rest of Hoboken. Before I finished my shower, I had four down. That would be enough to scratch the surface.
I got dressed and convinced my roommate and his girlfriend to come with me to a friend’s apartment. She was having her annual St. Patty’s Day bash. I was meeting D and K there as well. I was happy D was going to be in town. Since his car got a flat, he wouldn’t be visiting his girlfriend in Philly.
When I got there, the party was already well underway. I sat on the arm of the couch and conversed with my friends. I just took in the scene. For some reason, I wasn’t really feeling St. Patty’s Day this year like years passed. I didn’t feel the need to get sloppy drunk.
Of course, since my bladder has shrunk since college, I had to go to the bathroom. Since I was somewhat bored at the party, I was chatting with a sexy man I’d been chatting with for some time on Grindr. We’d talked about getting together so many times, but never did. Things were getting very flirtatious and leading toward an afternoon hookup. When I went to the bathroom, he suggested I come over. I took the opportunity to sneak out the door when I finished in the restroom instead of returning to the party. I’m sure it was just a matter of time before my friends realized I’d gone, but it wouldn’t be immediate.
I wasn’t even slightly drunk. I’d been anxious to see this guy for some time. I wasn’t about to let the opportunity pass. I quickly walked home, grabbed my helmet, hopped on my motorcycle and sped off uptown. Before I left the party, my Grindr friend asked me how I felt about glory holes. I told him I’d never used one before. When he sent me a picture of a sheet with a hole cut in it and a caption reading, “How would you feel about this?” I became excited. He told me he’d leave the door unlocked. I was to walk in, come to the sheet, unzip and let him take care of the rest.
Warning: The following may be too graphic for some. As I entered, I noticed how nice his place was. I was a little shocked. I walked straight to the sheet hanging in the bathroom door. I hadn’t even fully unzipped before he reached his hand around the sheet and began. It felt amazing! He continued for some time before I reached my hand around the sheet and began to stroke the back of his head. I could feel him, but I couldn’t see him. Finally, my curiosity got the best of me, and I just pushed the sheet to the side. I wanted to see him. He was very attractive in his pictures and even more so in person. On top of that, the only thing he was wearing was work boots.
After a little more time, he turned around and I began grinding myself against his backside. He was extremely hot and he knew how to use his body. I reached around and used my hand to pleasure him as well. He was VERY gifted. I hadn’t felt one like that since my friend in San Francisco.
He then requested we move things to the couch. I sat down, and he straddled my lap. It didn’t take long before he finished all over my chest and without warning. I had no idea it was coming. I tried to finish as well, but it was no use. Between my morning visit and the few beers I had, I sat there for quite some time without climaxing. He was so hot and he tried everything to help me finish, but it was no use. I gave up and apologized. I could tell he was very disappointed. He blamed the drinking, and I concurred that was to fault.
As he stood in front of me, I took all of him in. He had a spectacular body, and I let him know it. I asked him about his workout routine, and he told me he didn’t since his heart attack. He elaborated and told me it was no big deal, but I was a little worried. I could only think of him keeling over in front of me.
We chatted a little bit more while I got dressed and looked around a bit. He told me he had a roommate, but he wasn’t home. Something didn’t quite line up, but for some reason, I was buying the story. While we chatted, he stood in front of me in just his boots with his large gifts swinging back and forth. He was very proud of them as well. He put sweatpants on so he could walk the dog, and I could see his large bulge. I commented on it, and he commented how he loved how people would check it out, especially the guys with their girlfriends. I was so turned on. I also learned he managed a bar in the city, and he told me I should hit it up sometime.
We talked about meeting up again sometime soon. We both thought the other was thoroughly sexy and wanted a repeat. He was particularly looking for a sequel since he didn’t get a happy ending from our first encounter.
I said goodbye and made my way back downtown to my apartment…
Follow @onegayatatimeStood Up Twice But Third Time’s a Charm
Posted by One Gay at a Time in Gay Dating on April 13, 2012
So much for getting things out of my system while in California. I was supposed to find myself while I was out there. I was supposed to calm down with the hookups. If anything, it had a converse reaction. Maybe it jump-started my libido. Since I arrived home, I had one meaningless one-night stand/hookup, and hooked up with a guy I could possibly considering seeing again. What was I, in college?
Wednesday at work, I was back to my old habits. I was all over Grindr searching for guys to go on dates with. The problem was none of them were looking for dates, so I decided to fill the time between dates with more hookups.
I hit up one of the guys in my favorite list, but he was really just interested in sex. We tried to make plans to meet up, but were having a hard time finding a location. He proposed an adult video store booth, but as you can imagine, I wasn’t onboard. He also wanted to go bareback, but I’d learned my lesson with that. No more taking those kinds of chances. When I tried to make more realistic plans, he flaked.
I started talking to one guy who was really hot. He wanted to hookup badly, but he needed time. He needed to prepare, which I can heavily respect, but he was also visiting. He needed to go out and get supplies to perform said preparation and needed to find poppers. It was pushing 6:00, and I wasn’t going to hang around the city any longer. He ended bailing on me, so I made my way home alone.
Two guys flaked on me; however, talking to them got me riled up. My libido was hungry. When did I become such a horn ball. After 25 years of basically no sex, you think I’d be fine going home with just my right hand.
I had an ace in the hole though. I texted the Middle Eastern guy from the pervious night and asked if he wanted to come over again. I don’t think I lifted my finger off the send button before I got a response back. He was certainly interested, but had to come over later after class. He wouldn’t arrive until around 10. That was fine. I figured out other things to do with my time, like eat dinner.
When he arrived, we went straight to my room, but I’m sure, much to your surprise, we didn’t immediately jump in the sack. We kissed for a bit, but then we simply laid next to each other cuddling while we watched Modern Family. We are both big fans!
Every time there was a commercial, he took the opportunity to kiss me passionately. There were no complaints from me. He was a great kisser. He had perfect lips and knew what he was doing. We also took the time to chat a bit. I wanted to get to know him a little. He lived with a bunch of guys in an apartment and even shared a room with a guy. None of them knew he was gay, and he recently broke up with a girl. He told me he’d been on a handful of Grindr meet-ups, but none were anything like what we shared. He told me how much he enjoyed the previous night and how much he thought about me all day long. It was very flattering, and a little alarming. This kid was falling for me — and fast. I needed to make sure things didn’t get out of control because I didn’t want to hurt him.
I couldn’t tell him what I was looking for because I didn’t know what I was looking for. I really wanted to find a boyfriend, but I wasn’t sure he fit the bill. This was new territory. I’d never dated anyone so much younger than me, let alone still in college. He was a really nice guy, and I could tell his friends loved him, but I was still conflicted. He was very mature, but nonetheless, he was still in school.
When the show was over, the making out led to heavy petting. Things escalated, and I invited him to spend the night. While naked, he walked to the bathroom to take out his contacts. I watched him from the bed, staring longingly at his body. I told him how hot I thought he was. He really riled me up. I loved the innocent confidence he exuded. It was incredibly sexy.
He told me he wanted to go to bed horny so we could wake in the morning and have some real fun. It was late, and I was tired, so I didn’t oppose. With that, he rolled into little spoon position, and I pressed my naked body against his in big spoon position. It felt so comfortable. It felt so right.
In the morning we both woke to the sound of my alarm — strategically set early to allow for time to play. We were both in a very frisky and playful mood. He certainly wasn’t shy about kissing. He loved it and did it often.
Warning: The following may be too graphic for some. While we embraced each other, he whispered in my ear how he wanted to ride me. I certainly was in no position to deny him this privilege. I was looking forward to it. I was shocked, him being so new, how much he was gung-ho about bottoming. I think he discovered he’s really a bottom. He hopped on, and it felt great. He came really close to finishing, but never did. I knew exactly what was happening, so I didn’t put any pressure on him or comment on it. That would only bring it to top of mind and make it worse.
He had to stop. He wanted to keep going, but told me he was sore. He informed me that I was a big guy. I’d never really thought of myself as big. I always thought of myself as average. But, as of late, I was informed otherwise. (This is not something that is important to me, but it is quite the ego boost to hear).
We laid next to each other once again pleasuring ourselves while he laid in the crook of my arm. I finished after a few minutes. I was happy things were turning around for me. It wasn’t taking a long time for me anymore. I was far from a one-minute man, but my mental block was easing. This wasn’t the case for Middle Eastern (will be called M.E. from now on). He never finished, but also never complained. He noted, “I can never [finish] after you’re inside me. I can’t explain it. It feels amazing, like a full body orgasm, but I just never shoot.” I knew exactly what he meant. I told him it’s just part of sex sometimes. I wanted to ease his mind.
With that, we both hopped in the shower, and I took the opportunity to wash him from head to toe with a bar of soap and my hands. It was really sexy and slightly romantic. We both enjoyed it. Then he did the same to me. It felt great!
While I get ready in front of the mirror, he noted its existence. He complimented me on what I was wearing to work. He really was charming and sexy. I was really starting to like this kid. I just worried we wouldn’t be able to have a real relationship. He was in the closet and in college. He told me he wasn’t hiding it anymore, but he was advertising it. I understood, but I just wasn’t sure if it was for me
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 @onegayatatimeIs This Going to Become a Trend?
Posted by One Gay at a Time in Gay Dating on March 29, 2012
Once again I had a Friday off from work, and once again I found my libido taking over my ability to reason. I woke up that morning feeling frisky, and of course I pulled up Grindr to see who was around.
I went through a lot of guys and even started acting like all the other guys I hate on Grindr. I was skipping the pleasantries and getting right to the point. I knew I needed to find a guy who was simply looking for one thing. I didn’t want a guy who would linger or keep calling. I just wanted my libido satisfied.
I finally found a guy who seemed to be interested. He was a black man who had an amazing body. When I gave him my proposition, he surprisingly responded with a reasonable response. He didn’t normally seek out hookups, but he understood the periodic need to satiate the animal within. He wasn’t completely comfortable with just coming to my apartment and jumping into bed. He wanted to meet me in person first. I learned we both went to NYSC, so we agreed to meet at the gym and take things from there.
I get no service when I’m at the gym since it’s completely underground. I texted him just before entering “the cave” telling him what I was wearing and that I’d arrived. I worked out for nearly an hour, and he hadn’t made an appearance. I assumed he stood me up. I actually walked upstairs until I got service to exchange a few texts with him. He was on his way. I informed him I was nearly done my workout. I guess my libido was slowly fading with the endorphins of working out.
I was doing my last circuit of abs before I was ready to head out when I finally saw him emerge from the locker room. He came right over to the mat. I smiled as he approached, and he laid down next to me. He started doing sit-ups at a rapid pace — So much so that his shirt began to lift and expose his abs and the tiny shorts that barely covered him, exposing a majority of his jock strap. It certainly wasn’t anything I’d attend the gym wearing, but I could tell he was a bit of an exhibitionist.
The whole time, I waited for him to get my attention and say something, but he never did. After a few sets, he got up and walked away. I assumed he wasn’t interested. Apparently, I’d just been rejected without a word. It was quite a blow to the ego. Maybe I needed to stay at the gym a little longer.
I made my way into the locker room to change when I discovered him getting undressed right next to my locker. He was standing there in his jock strap putting his clothes into his locker when he stepped back and removed the jock as well. He was quite the “gifted” man. Of course I was sneaking a peek every chance I got. It’d been a while since I’d seen someone so “gifted” in person. It was very difficult to hide my own excitement in my gym shorts. I needed to leave before I got really excited and someone took notice.
He grabbed a towel and made his way towards the showers. It was just the tease I needed to get my engine revving again. Looks like it was going to be the computer and me when I got home.
As I left, I texted him declaring my disappointment at his lack of interest. He responded back almost immediately, “Did you leave?” I explained to him I was done my workout and thought he wasn’t interested, so I was heading home. He told me he was definitely interested, and he just didn’t want to interrupt my rhythm. He told me he’d be over in a short bit.
When he arrived, we sat on my bed chatting a bit. He was a freelance journalist over in New Jersey covering the Whitney Houston funeral. He seemed like a really intelligent down-to-earth guy. It made the hookup a little more relaxed and less transactional.
Warning: The following may be too graphic for some. Things started to get hot and heavy, and we both found ourselves naked enjoying each other’s embrace. After a short while, I took out a condom and some lube while he relaxed on his back. We were going at it for a little while when I accidentally slipped out of him. I wasn’t the only thing to fall out however. I sincerely hope my face didn’t show what was going through my mind at the time. This wasn’t as bad as the guy in San Francisco, but it certainly wasn’t pleasant. There was a pea-sized nugget laying on my sheets at the base of his behind. If this was going to keep happening, I was going to learn to be celibate.
I quickly improvised and suggested we continue our activities in the shower. We had some fun in there until we returned to the bed. I did my best to avoid the nugget while we both tried to finish ourselves off. Finally, I climaxed (I’m amazed I was able to with everything going on around me).
He informed me it would be a long time before he was able to finish himself. Apparently, he had similar issues to my own. I was happy in the realization my symptoms were finally lessening, and I was able to relax and finish more readily.
He got dressed, and I said goodbye to him. About ten minutes later, after immediately throwing my sheets into the washing machine, I received a text from him. He’d left a bracelet behind — And it was very important to him.
DAMNIT! I was going to have to see him again. I told him I’d bring it into the city sometime, but he suggested he would collect it over the weekend the next time we were both heading to the gym.
In the end, we needed to plan an evening for him to swing by and pick it up, but this time I told him, “No sex.” He stopped by for all of thirty seconds while I handed it to him through the door, never to be seen again.
Follow @onegayatatimeBoston Therapy
Posted by One Gay at a Time in Gay Dating on February 21, 2012
My relationship with Smiles had come to a close. We met. We discussed. I guess you could say we had closure.
I’d already moved on to other men and began rebuilding my roster. It’d been a while since I was in the game, and I was a little intimidated. Over the three months I dated Smiles I lost my edge. It was my sister who pointed out to me, “I didn’t like you with him. You weren’t yourself. You were much more reserved around him.” I didn’t like the sound of that. I pride myself on being open and myself all the time. Apparently, I lost that somewhere along the way. I needed to find it again.
I would do so with the help of my therapist, Boston. I really lucked out in my timing. Boston was on a break from his final year of school, which meant his services were available. I was going to take full advantage. He was a good friend, and I missed him. I was really disappointed we didn’t get to meet up when he came to visit New York for New Years. It really made me look forward to the day when he graduates, and I convince he to come to New York or Hoboken so I can have him around more often.
Monday night when I got home from work, I called Boston. I wanted to give him an update on how everything with Smiles went since we’d been chatting about it a bit. I told him how everything ended and how I was moving on.
Ironically enough, Boston had a few tales of his own. Apparently, a little of me was rubbing off on him. I was very happy to hear this news. Sometimes I think he puts his love life on the back burner too much. I think he loses hope at times and engulfs himself in other ventures. I want to see him happy. He’s a great guy and he deserves this.
So, when he told me about a straight friend of a friend coming to visit and the sub sequential hookup that ensued, I was downright proud. He managed to attract a “straight” man enough that this man took the opportunity to make out in the bathroom of a club.
I was so happy to have my friend back. I loved swapping stories with him!
I also took the time to explain to him how LES wouldn’t talk to me. For the life of me, I couldn’t figure out what I could have done to him to make him stop talking to me all of a sudden. We were building a strong friendship. I had the feeling he developed feelings for me, especially since he asked me, “So what’s the deal with [Smiles]?” He invited me to his birthday, and I missed it. I apologized, and he told me it was okay. I invited him to my holiday party, but he dropped off the face of the earth and never showed. Following, I attempted to reach out to him on numerous occasions. Okay, so maybe I’m under exaggerating. I tried to text or call almost every day for a while there. I thought I was being funny, but now looking back, I could easily see my actions being misconstrued. Maybe he thought I had stalker tendancies.
In the end, things got very suspicious. He would never respond to my Facebook messages, and he never showed up as online. However, he never unfriended me. As long as that didn’t happen, I didn’t think he was all the annoyed by me. I sent him another long apologetic message on Facebook asking him to please reach out to me. When I finished writing it, I thought I’d give him a call to see if I could get through. It’d been about a month since I last texted or called. When I did, I was shocked to find out the number was no longer in service. He either blocked my number or changed his.
I couldn’t believe it. Had I really taken it that far. Maybe he wasn’t mad at me. Maybe he was afraid of me. I hung up the phone and immediately sent another Facebook message: “I’m sorry if I’ve been bothering you. Don’t worry. It won’t happen anymore.” I was mortified. Did he really think I was that insane, or was he really that mad at me. I was really hurt that someone would ever be that mad or upset with me that they’d simply cut me off. My ego was seriously bruised.I also happened to be perusing my old messages on OKCupid, and it told me LES deleted his account. When I made a new OKCupid account shedding an identity I’d used since college, I came to realize he was still on there and had an updated and active account. He’d blocked me on there as well. He really wanted nothing to do with me, and there was nothing I could do about it.
“You can be a bit aggressive,” Boston told me. That really resonated with me. I did tend to be agressive. I’m a tenacious man. When I see something I want, I don’t give up until I attain it — This goes for everything.
The interesting part was that I simply wanted a good friend back. He was a really fun guy to be around, and I wanted to introduce him to Boston. I thought they’d make a GREAT pair. I would have loved to see the two of them together. But, I don’t think that will ever happen. New York is a big city, and I don’t know that we’ll ever cross paths again.
Boston and I talked more over the course of the week. We almost had a nightly check in for a while there. We’d chat on the phone for about an hour about our dating lives and the mistakes I made with Smiles. He told me more stories about another guy he was helping to introduce to the gay world. I hope I’m not blowing up Boston’s spot, but once again I was proud of him. He was facing new challenges and having new experiences. I was happy to see my friend experiencing more of life these days. I understood how busy school made him, but at least he was taking advantage of his time off.
I was building my roster and had a friend to gossip about all the new things going on in my life. Things were getting better, but I still wasn’t happy to be back out in the dating pool. I was anxious to land another man, but this time around, I wasn’t going to just settle for a guy who was willing to date me. I needed to “find a man who will worship you like you worship him,” as my friend A so eloquently put it. I needed a real man, not another little boy. A man who could express himself verbally, emotionally and physically. I was going to find a triple threat, and once again I had one of my closest friends in my corner.
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 
The Next Chapter
Posted by One Gay at a Time in Gay Dating on April 16, 2013
Two years ago, I started this blog. I began writing because I felt alone. I knew there had to be other gay men out there who were looking for the same thing I was, and I wanted a way to connect with them.
Since the beginning, I have gone on MANY dates and put myself in many situations well outside my comfort zone. I have not only grown more comfortable in my own skin, but I’ve also grown up as a gay man. I got all the hookups out of my system and began searching for a meaningful, long-term relationship.
This blog began as an open forum diary of the daily occurrences I encountered navigating the gay world. I told my side of the story honestly in hopes that others out there would be able to relate, comment and most importantly, realize they are not alone.
When I first told CK about the blog, he was very open to and even grew excited about the idea of my writing our relationship. Over time, as you could probably understand, his excitement waned, and we began to argue about the content of the blog.
I had to make a choice between the blog and my man. It’s quite obvious which I chose. As a result, I will no longer be blogging about the specifics of my relationship with CK. However, in lieu of continuing to finish our story in a daily dairy format, let me catch you up on what has happened since July. Here are some of the highlights…
It took a lot of time for CK and I to figure things out. This wasn’t the first time our relationship reached physicality, but I hoped it was the last. It also took a long time for things to return to normal between CK, me and my circle of friends. My sister wasn’t speaking to me for over a month and my friends had semi-ostracized me from typical gatherings. I burned a lot of bridges on that trip, and I am still working to rebuild them today. You can expect to read about my experiences and feelings dealing with issues such as physical violence in a relationship as one of the topics I will cover in coming posts.
After Sandy exhausted my last modicum of energy, I decided I was too tired to shave my upper lip. CK and I both decided to raise awareness and funds to fight prostate cancer by growing mustaches for Movember. I proudly raised over $500 for charity as a result of my stache, and I was thrilled when we both shaved them off — We both looked like pedophiles.
When I returned to Hoboken after Thanksgiving, preparations began immediately for what would have been my Sixth Annual Holiday Bash. This year, it became Our First Annual Holiday Bash. I finally had someone to share the hosting duties with, making it extra special.
In February, CK and I took a romantic trip to Mohonk Mountain House in New Paltz, NY. Although it seems we can’t go anywhere without having some kind of quarrel like an old married couple, the trip was amazing and couldn’t have come at a better time. We went ice skating, snow shoeing, swimming, hiking, and much more. It was a perfect escape for both of us to get out of the city and away from the bustle of it all after the holidays.
In between, there have been countless brunches, parties, trips, nights out, Broadway shows, fights… Oh yea, and plenty of sex — Can’t forget the sex! Overall, things have been going well for us. You have good days and bad days, but you have to realize the bad days are just there so you appreciate the good ones all the more. I am thrilled to announce, this past Saturday, CK and I celebrated our one-year anniversary at the restaurant we went to on our first date, Frankies Spuntino 570. Although we waited nearly an hour, the evening was perfect, and I look forward to many more years together.
Although I won’t be detailing the specifics of my relationship going forward, I hope to share with you what I have learned along the way. It’s not easy being in a relationship, but then again, the things that are worth it never really are.
To my most dedicated readers who haven’t let me lack of posting stop them from commenting words of support on my blog, thank you. You are what has motivated me to get back into this once again. I feel like many of you have integrated my writing into your daily routines, and I have left you with your morning coffee in hand and no reading material. You will not see the frequency of posts you may have grown accustomed in the past, but I still hope you find time in your lives for One Gay At A Time.
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