Posts Tagged gay sex
It’s About Time
Posted by One Gay at a Time in Gay Dating on February 27, 2012
Today is a Fast Forward Monday!!!
My apologies to those who have come to expect Fast Forward Fridays. I have been traveling for work/pleasure, and I got caught up in things. I haven’t had a chance to write the second post, so I’m making up for it today. Hope you are enjoying these. It will help bring the blog a little closer to real-time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!
Back to your special edition of One Gay At A Time…
After missing the opportunity to finally meet my online friend after almost a years time chasing each other around, the day finally arrived when I was scheduled to finally meet him in the flesh. This was well overdue, and I was quite excited. I wasn’t about to get ahead of myself, but the suspense had been building up for quite some time.
We discussed where we would go for drinks or dinner and finally settled on Charritos, a Mexican restaurant I’ve been to on numerous occasions. In fact, this wasn’t the first date I took there. We planned to meet at 7:30. I knew the place didn’t take reservations, but it was a Monday night on a holiday weekend. I figured everyone was home getting ready for the coming workweek. It also wasn’t the nicest night, as snow was in the forecast, so I thought we’d be alright.
When I arrived, I was immediately proved wrong. I stood in front waiting for him to arrive noticing every table (all 8 of them) filled with diners. Finally, he arrived, and we attempted to go inside out of the cold. Even this proved difficult since there was nowhere to go once we were in there. While we waited for a table to clear, we awkwardly chatted.
This was surprisingly difficult. He seemed so incredibly flirty online and charismatic, and the man standing in front of me was a very shy reserved individual. I couldn’t get over it. Where was the guy I’d been chatting about my body and sexual interests in detail? Where was the flirt?
We talked about work and the weather. It was a struggle to find a topic to discuss. Everything felt forced. It wasn’t awful, but it certainly wasn’t what I expected.
Finally we got a table and sat. After we ordered, we started to chat a bit more. I asked most of the questions. He always responded in detail, but he never asked a question in turn. That may have helped the conversation flow much more freely, but it wasn’t there. I had to volunteer all my information. I feel awkward talking about myself when I wasn’t asked to. It was as if I was interviewing him for a job.
One topic we got on was siblings. I don’t know why, but that topic has been coming up more and more frequently on my dates. I’ve actually noticed it and tried curbing it. I learned about his siblings as well. It was nice to hear he came from such a similar family dynamic.
We talked about his job as well. I was very intrigued by it. He told me all about his schooling, his specialty in the field relevant to the gay community, his boss, the clinical work he does… This was really shaping up to be quite the catch of a man. He was very sweet and thoughtful. However, our chemistry was not mixing AT ALL! It was so disappointing. On paper he looked so good. Online, he seemed a sexual match for my libido. In person, he was a mouse. Night and day from my expectations.
After quite a while, the waiter basically asked us to leave. There were people waiting for a table, so they kicked us out. I was more than a little p*ssed, because I thought it was very unprofessional and rude, however, it was time for the date to conclude.
We’d already talked about him coming over to my apartment before the date. I was still very sexually attracted to him. I wondered if he’d relax when he was out of the public eye. As we walked outside, I asked him where he parked and told him I’d walk him to his car. I was hoping for a signal along the way to show his interest. I thought he’d drive me to my apartment and come up.
When we got to the car, it was the complete opposite. I hope you can understand my explanation without a diagram:
I thought we’d at least say a proper goodbye. I was hoping for a kiss considering all I could think about during the meal was how good his lips would feel. When we got to the car, I stood on the sidewalk, and he walked to the front passengers panel in front of the rearview mirror. That would have been fine. I may have even used the car as a backboard for a strong kiss, BUT there was also a chopped off parking meter between him and myself. Yes. A metal pole about four feet tall was between the two of us. I don’t think he could have strategically showed his lack of interest any more other than to simply get in the car and drive away.
We said goodbye, and I told him it was nice meeting him. He said, “Likewise.” That’s when I grew some balls and took what I wanted. I moved forward, reached my long arm over the pole, hooked it under his arm around his back, and pulled him in for a kiss. It wasn’t a long kiss or a makeout session, but I certainly wasn’t going to be satisfied with a peck.
And with that, I turned and walked home in the flurries falling from the sky. I was still a little blown away by the lack of spark during the date. I wasn’t even ready to go home. I decided to stop by my friends’ place on the way home and say hi.
I came in and we caught up on what’s going on with each other before I told he and his wife about my awkward date. He was a little baffled by it as well. He couldn’t understand what was going on. He really loved the parking meter pole story as well. I was so nonplussed.
I sulked home after saying goodnight to my friends. When I got home, I was curious to see if he was back on a4a. Surprise! I was right. I wasn’t going to get past this immediately. I needed to ask him about what happened.
“Surprise, surprise. Look who’s on here,” I messaged him. We chatted a bit awkwardly about the date. He messaged me back: “I was waiting for you to ask me to come back.” He wanted to come back to my apartment. He even brought his c*ck ring and poppers with him. I was so confused, and I made that clear to him. He wasn’t aware of his mixed signals, nor was he aware of the pole. He just thought I wasn’t interested since I walked him to his car. It was all a big misunderstanding. “I had a good time. I thought the conversation was nice,” he added. That doesn’t make up for the awkward date however. That just cleared up the mixed signals at its close.
Just to satiate my curiosity, I told him we would have to try to fix what went wrong when I got back from my work trip to San Francisco. He agreed, so we kept in touch over the next week.
I decided to see what was going on with the southern guy. He texted me to see how my weekend was, so I picked up the phone and called him. Again, we talked for almost an hour while I packed. This completely made up for my awkward date. I was really looking forward to getting back so I could finally meet him. Hopefully this one wouldn’t be as big a disappointment.
In the morning, I had a message from my new southern gentleman caller. He was asking for a picture of my “morning excitement” we’d discussed previously. I denied his request and told him he’d have to wait to see the real thing. This was my way of getting him on the ball about meeting up with me.
I also got a text message from my friend and recent neighbor. It was very sweet of him to do so. I needed to make it a priority to hang out with him when I got back to New York.
All that would have to wait on the backburner… The following day, I was headed to San Francisco for the week for work. Waiting for me were two men. One I attempted a long distance relationship with whom I would meet for a cocktail. The other, a great confident and online friend whom I was extremely excited to meet in person, especially in the bedroom…
Follow @onegayatatimeJuggling Act
Posted by One Gay at a Time in Gay Dating on February 27, 2012
Over the course of time, I began talking to a guy who’d been in and out of my life for almost a year. I think I started talking to him on Grindr first. We then found each other on adam4adam.com. Finally, we became Facebook friends.
You would think with all this contact, we’d be best friends or lovers by now, but that wasn’t the case. Whenever I was between guys I was dating, I would once again hit him up. He was very attractive and seemed to have a very level head on his shoulders. I really wanted to get to know him better, but I got the feeling I was going to have to pursue this one. I wasn’t going to win him over overnight.
For some reason, this time around was a little different. He was much more receptive to my advances. When the conversation would die down, I would prod him about losing interest. He would deny it and pay a lot of attention to me. He was constantly asking for me to send him pictures of myself and sending me compliments. It was nice to have a man tell me I was attractive.
We spent many evenings chatting on a4a and Facebook. I got to know a lot about his sexual side through those conversations. They would start innocently enough about our typical lives and somehow they’d always segue into our sex lives/desires. I was okay with this because I wanted a good man with a healthy sexual appetite. This was something I’d come to learn as of late. I needed to stop sacrificing good sex for a decent guy. I needed both.
I was also trying to juggle him in with the other guys on my roster. It is always such a challenge to get gay men to commit to anything. They never seem to want to be locked down to anything. I would schedule a date, and sure enough they’d always cancel or postpone. I was really getting tired of flakes running my social life. When my Friday night date cancelled, I tried to see if he was free for a drink.
I wasn’t able to meet him when he was free. He already had plans to go to Sugarland, a gay club in Brooklyn with a friend. He reported to me about his night with texts and pictures. Apparently he wasn’t having the best time and told me it was “Indian night.” Not his cup of tea. Since we couldn’t meet on Friday, we agreed to try for Saturday night.
It was going to be tough however. I was supposed to be attending my sister’s birthday gathering at a local bar. He had plans to go into the city. We agreed to try to meet up later, but who knew if that would come to fruition. He said, “I may head into the city, but we’ll both probably be out late… Let’s keep in touch and see where we are at later.” Of course, we’d never find each other that night. He still insists he sent me text messages to meet up, but I never received them.
Instead, when I got home, I texted my new “friend with benefits” to come by. I even volunteered to let him spend the night so he wouldn’t have to walk in the cold. He agreed and came by.
We had a great night together. He was really a passionate lover. It’s too bad he was so old. Instead, we’d simply just take care of each other’s physical needs.
At 6am, we woke and fooled around some more. Again, we never had sex because we are both tops, but he did mention the possibly of bottoming for me in the future.
At 8:30, he left to go home to get ready for church. I stayed in my bed and went back to sleep.
When I woke up later, I told him and my new southern friend about my upcoming work trip and how I really wanted to meet them before I went away. The southerner had to pass because he was helping move a good friend into her apartment. We agreed to grab dinner Monday, Martin Luther King Day in the evening. Hopefully this date would finally come to fruition…
Follow @onegayatatimeHighs and Lows
Posted by One Gay at a Time in Gay Dating on February 24, 2012
I had been on OKCupid only a short while before I met Smiles. I met only one person from the site, LES, and that was already after I met Smiles. I have to say, I’m not that big a fan. Every search I did produced few candidates I was willing to entertain. No one was good-looking, and no one had exciting profiles. It reaffirmed for me why I originally was so against dating sites. I felt like it was full of desperate men.
Rarely would I receive a message for a worthy candidate, but when I did, I would quickly respond and dry to stir up some dialogue.
I started chatting with a nice southern boy from North Carolina who moved to the city in the previous few months. He seemed like a really genuine guy who wasn’t into the scene or fully out. I was very attracted to that. The southern boys always brought a little extra something I always liked. They were mannered and real men.
We messaged back and forth on OKCupid for some time before we exchanged phone numbers. One night, he asked if I could chat. I asked him for his gchat or AIM name. He responded, “No. I meant on the phone.” To which I responded, “Sure.” We spoke on the phone for an hour that night. I really got to learn a lot about him. He was volunteering a lot of information about his upbringing and his company and where he is today. He told me how he hates gay bars. He even took the time to tell me about his “hetero life partner.” That’s what he calls his best friend and roommate he left behind in North Carolina when he moved up here. Apparently they were completely best buds, however, nothing sexual ever transpired between the two of them. It was sexy to hear him speak about such a masculine love with his friend. I was really liking what I was hearing, and the fact that he wanted to call gave him so many bonus points in my book. I even told him that last bit of information, which I think he really appreciated.
In the morning, things switched to texting. He was horny and asked me to send him some more risqué pictures. I was onboard. I was all the more happy he asked actually. It proved to me he had a healthy libido, especially in the morning, which is when I’m at my horniest. We exchanged a few racier pictures and went to work. We made a commitment to each other to try to find some time to go out on a date in the near future. I couldn’t wait. He was not only sexy to look at and hopefully to touch, but he was also sexy and masculine in his personality.
In the meantime, I was also talking to a guy I met on adam4adam.com who I’d been messaging on and off for over a year. Between every relationship, this guy and I would exchanges flirty messages and pictures, but nothing would ever transpire. It was so frustrating because I found him to be very hot. He’d get very flirtatious, but never follow through or agree to meet me. Now I was making some ground. This time around, he seemed genuinely interested. I’m not sure what changed, but I was going with it. He was coming back home after a weekend away, and we were texting the entire ride back. When he got home, we continued the conversation on Facebook with a lot of banter and playfulness. He was really coming around on me. I continued to propose a date, but it wasn’t the easiest. He was open to the idea, but I couldn’t get him to lock down on a specific time and location.
A lot of our conversations revolved around sex. Again, after the dry spell I went through with Smiles, I was happy to hear it. I also knew he had a great job, as he had his doctorate and was using to teach at a college and work at a clinic. He really seemed like the full package. From looking at his Facebook pictures, I could tell he loved to travel and he loved to have a good time. He also lived close to me. I felt like this time, I had it in the bag.
That night, I found a guy on Grindr. He was visiting, and the host he was staying with was away. He knew no one and wanted to go out. I was already contemplating going out, so I convinced my roommate to join us at the bar for casual drinks. We met him on the walk to the bar, and when we did, I was shocked. He was tiny. I’m 6’2″, and he was easily 5’2″. My roommate immediately whispered a comment to me. Then he opened his mouth and the queeniest voice came out. I was so turned off, but I couldn’t be rude.
We awkwardly sat and chatted at my favorite bar that night. It was dead, so there wasn’t even anything to distract from the incompatibility. When my roommate and I had our fill, we decided to head home. The little munchkin followed us home. He asked if he could come over, and I agreed. It was a moment of weakness. I was horny, and I thought he could be fun.
BOY WAS I WRONG. He was beyond a stage five clinger. After some making out and heavy petting, he spent the night. The next morning, he told me the only way we could have sex is if I could see him the next night. Foolishly, I agreed. It was bad. No. Let me rephrase. It was awful! I couldn’t get rid of him fast enough. I kept laying it on thick how much I needed to get to work, and finally I scooted him out the door.
This was just gay karma coming back to bite me in the ass. I never should have led him on. From the bar, I should have had the balls to just send him home and take care of myself. This is where my penis gets me into trouble. Soon enough, he’ll learn his lesson…
Follow @onegayatatimePretty Fly for a Brit Guy
Posted by One Gay at a Time in Gay Dating on February 22, 2012
Life was returning to normal. I went to work every day, and I managed to fit in some gym sessions over my lunch breaks. I was feeling good.
I was free. I was single. I had no rules. Or at least I could live by my own rules.
Sadly, my old friend Grindr and I were rejoined at the hip. I wasn’t thrilled to be pals again, but he was a necessary evil. If I was going to straight bars every weekend, I was destined to live a life of the third wheel forever. I needed to do something proactive.
Most days at work, Grindr would sit open on my phone in the background waiting for the right guy to come along. Periodically throughout the day, I’d check on it to see what I caught in my net or to periodically toss out a new line.
I try to take my “lunch” at the gym at least twice a week. This frees up my evenings and actually makes me more productive. When the endorphins are flowing, I’m a far better worker.
I was also back on Grindr full force. I was on the hunt for a man. Mainly I was looking for a relationship. But, if the right opportunity came up, and I was in the mood, I wasn’t going to turn them away.
Just as I said before, if I wanted sex, I would go for it. But, if I wasn’t interested, I would simply let the opportunity go by. There was no need to hold on to guys for future use. There are plenty to go around.
Monday, on my way to the gym for a workout, I pulled up Grindr and began chatting with a great looking torso. We exchanged a few messages before he told me to come to his hotel. I laughed to myself and told the guy, “Sorry buddy. I’m on my way to the gym for a workout. Good luck.”
Apparently, he wasn’t done with me. He continued to message me all the things he wanted to do to me. Now, I was at the gym, and I was turned on. Originally I had no interest, but his persistence peaked my interest.
I learned he was a flight attendant staying at the Radisson Hotel near my office. This certainly wasn’t the first flight attendant I had a chat with staying at that hotel. It was almost a daily occurrence in the past. This one was hungry. He really wanted to give me a blowjob. He sent me a few pictures, and my interest was peaked even more. However, I continued with my workout.
Smiles and I were no more. I had to do what I could to attract a new man. I was focused on my workout. I needed to whip my body back into shape. It didn’t matter if it was winter. I wasn’t going to use that as an excuse. I’d lost some weight since Smiles challenged me on that subject. However, it all returned when my relationship was coming to a close. I was simply feeling lazy. The breakup was the kick in the butt I needed to get back to the gym in a dedicated fashion.
I told him I would not be able to come by because I was at the gym, and I had to return to work. I did offer the possibility of stopping by on my way home after work. I asked him what his plan was exactly. He stated: “I leave the door open for you. You come in with the lights out, we make out and I suck you off.” That was quite a plan. I had very little heavy lifting, and I would go home a happy man. “And I don’t have to do anything to you?” I added. “No. I just really love sucking c*ck,” he replied. The pictures he sent certainly showed him to be a very attractive and fit man. I wasn’t completely sold, but the prospect was top of mind.
There was one catch. I wasn’t done work until at least 5:30, and he had to leave the hotel at 6:15. As my workday was coming to a close, I messaged him to see if our arrangement could work out. He said as long as I arrived quickly, there would be enough time for him to blow me.
Yes, I know how incredibly risky this situation sounds. I also know how incredibly disgusting it sounds. I was completely using another human being. I’m not proud of it, but we all have a sexual animal instinct. Mine was starved for nearly twenty-six years. After that, it fluctuated. I was in need of pleasure, so I wasn’t about to deny myself that. Feel free to judge away.
I left work and went to the hotel. I arrived at his room and knocked on the door. He answered in a pair of shorts. I came in, and he immediately began making out with me. He was hot. I was really enjoying myself.
Warning: The following may be too graphic for some. He then unbuttoned my pants and pulled them down. He did all this while one hand was lifting my polo up, and he was licking my nipples. This guy was good. Good kisser and sensual bedfellow.
We moved things to the bed, and I stripped off his shorts. He had a great body and an amazing d*ck and a$s. I was having a blast. I scoped out his body. I told him to join me up on the bed so I could play with his body. He had a spectacular a$$ and an amazing d*ck. I was having a blast treating parts of his body like an amusement park for my hands and fingers. I almost couldn’t get over how sexy this guy was. He could probably have any guy he wanted. Why was he offering to blow guys without receiving anything in return? He must really enjoy pleasing another man.
Finally, I finished just as he requested. I really enjoyed all of it. It was a blast. I know it’s not the most conventional thing, but I saw no harm in this. He aimed all over his face. This guy really had a kinky side. I know I wouldn’t be able to do what he did, but if that’s how he got his rocks off, more power to him.
I asked him if he had a towel. These were the first words exchanged between us. We walked to the bathroom to retrieve a towel to clean up. I finally got to see him in the light. He had an adorable face to match his hot body, and I took the opportunity to inform him of all of this. On top of that, I heard him speak for the first time. He had the cutest British accent I’d ever heard. I wanted to take this guy home immediately. Sexy, good in bed, British accent — He was the full package! And, if it couldn’t get any better, when I gave him all these compliments, his smile was incredible.
I talked to him about his plans for the rest of the evening. He had to run to catch a flight back to the U.K. He was working and overnight. He planned on finishing himself off before he showered and made his way to the airport. We talked a little about his job, and I wished him the best of luck. With that, I was off on my way home.
As I walked to the PATH, I messaged him on Grindr and asked him for his email. I told him we could meet up the next time he was in New York City. Maybe we could even do something crazy like grab a drink. I dunno why, but I wanted this guy to be a pen pal of sorts. I was thrilled to think I could make a friend in the U.K., and I was sure he’d be back in the states often. When I got to the other side of the Hudson, he’d replied with his email. I sent him another Grindr message a day later when he arrived home. He told me he was looking forward to seeing me again. I told him when he came back to New York, we’d grab a drink at the bar sometime, but I still have yet to send him an email to set up a meeting time…
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 @onegayatatimeGray Hairs
Posted by One Gay at a Time in Gay Dating on February 17, 2012
Today is another Fast Forward Friday!!!
Hope you are enjoying these. It will help bring the blog a little closer to real time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!
Back to your special edition of One Gay At A Time…
That night following my breakup with Smiles, I went home feeling some freedom. I’d already gone on a date and hooked up before breaking up with Smiles. But, now that it was official, I felt I could do whatever I wanted.
It’d been a while since I had some good, wild, crazy sex. I was horny. I had three months go by with only a little bit of lovin’ in the bedroom. I was hungry for a good man and a good time.
I was very cautious of history not repeating itself. I was not going to let myself go wild like I had after breaking things off with N. I didn’t need to do it now like I needed to do it then. But, that didn’t mean I couldn’t have a little fun.
I pulled out Grindr and began my talent search for the night. I wanted to find a good time one-night stand type. Any guy who wanted to hook up with me the first night he met me would not be a guy I wanted to date. Yes! That is exceptionally hypocritical of me, but it’s my love life, and I make the rules.
I found an old friend on Grindr while I was searching. He was a guy who came over to my apartment one rainy night shortly after breaking up with N. We were both staunch tops at the time, so we just fooled around a bit, but he had a great body and was a lot of fun. Even though we didn’t have penetration, we managed to find other creative ways to ensure the other fully enjoyed himself.
We chatted a bit, and he told me he missed me. I explained why I hadn’t been around as he told me he was hoping I’d hit him up again for a fun night. I told him to come by, and I would surely show him another good time. He tried to convince me to come to his place, but I insisted on hosting. I just felt more comfortable in my own bed.
He came by, and we laid in my bed just talking for a little bit. He had on many layers, and I slowly stripped a few off so he would be more comfortable while we laid there. Eventually, we started making out, and I rolled him on top of me.
Warning: The following may be too graphic for some: I stripped him down to his briefs and fully appreciated his body. He was an older gentleman, but he certainly kept in shape. Everything was still tight and sexy. I hoped I would be in such good shape when I was older. Ironically it was that night I learned he was in his last year of his forties. I had no idea he was so old. I was shocked in fact. It didn’t change the fact that he was a sexy specimen of a man, but it kinda flipped my mentality on end. Up until this point, I thought the forty-year-old was the oldest I’d been with. He looked a lot like Ulrich Alexander Fox.
Regardless, he had a great d*ck and an amazing ass. I was ready to have some fun. I recalled his position as a top only, so I knew there would be not penetration again, but ironically enough, he volunteered, “Maybe sometime I’ll let you inside me.”
I was completely caught off guard. I replied, “Really!? Why’s that?” “Because you’re sexy, and I really feel comfortable with you. Maybe some day.” I asked if he ever bottomed, and he told me it’d been many many years since he’d last done it. I felt privileged. I was getting the ego boost I needed to get me back on my feet. It couldn’t have come at a better time. Here was a guy who was looking forward to another romp in the sheets with me, and we’d never even had full intercourse. Maybe I was better in the sack than I gave myself credit for :).
I had a lot of fun with him that night. He went down on me, and I finished like a pro. He commented on how he wished he still got as hard as I did and was able to shoot like I can. I then, with jello legs, helped him finish as well. He certainly deserved that after the fun night I was having.
Afterwards, we laid next to each other and just talked for a while. It was then I learned he was actually black. I’d noticed he wasn’t a white guy, but I wasn’t sure what his background was. I had nothing against this at all. I’d just thought maybe he was of Middle Eastern descent or possibly Egyptian. I also learned he was adopted by what seemed like a picturesque white family in Connecticut. He was very happy explaining his upbringing. I could tell there was a lot of love in that family. I was happy I had a real man in my bed and not just a body to hook up with. I’d never start a relationship with him, but at least this friend with benefits was an interesting guy with a big heart.
He again told me how much he missed me and being with me. He also told me he hoped we could find time to meet up again in the future. He encouraged me to come to his place some time since he lived alone and had a nice apartment. I told him I would certainly come to him next time. I learned he really wasn’t a creep, but a decent guy with a decent libido.
I once again took the opportunity to admire his body and tell him how hot he is. He was embarrassed by my compliments and talked about his need to take more care of his body. I insisted it was pretty amazing, and he directed the attention toward mine. He told me in detail how hot I was and how thrilled he was to have fun with me.
We continued to talk as her got dressed. I walked him to the door and gave him a kiss goodnight.
It was exactly what I needed right when I needed it. I had fun. I got an ego boost. And, I had a smile on my face for at least the rest of the night. I would sleep a very happy man that night!
Follow @onegayatatimeClosure
Posted by One Gay at a Time in Gay Dating on February 17, 2012
Saturday finally arrived. Smiles so graciously found time in his busy schedule to meet with me to discuss “us.” I wasn’t in a combative mood, but I was resolved in the notion that I wouldn’t be a doormat for him anymore. I had a lot of things I wanted to say to him, but I didn’t rehearse them in my head. I wanted my emotions to speak for me.
I knew how I felt, and I knew how he let me down. I was so disappointed in him for simply trying to back away from our three-month relationship instead of just speaking to me like a man. I was embarrassed for him.
We decided to meet at Doma Coffee Shop. Ironically, it’s pretty much where our relationship started (after a failed date at Employees Only). I had a few places to go in the city that day, so I took the motorcycle in. It was a nice enough day I could get away with it with a few layers.
After I parked my bike and walked toward the shop, I noticed Smiles was just arriving. We shared an awkward hello. I think he may have been going in for a kiss, but I gently turned and just gave him a hug. I had no interest in giving him any more of my affections. I’d already given him enough.
We went inside, and he ordered his coffee and began to pay. I wasn’t expecting him to buy my coffee, but it was interesting he didn’t even offer. He found a table for us to sit at while I ordered my coffee.
I joined him at the table, and we awkwardly chatted about work for a bit. Surprise, surprise — Our conversation revolved around his job once again. I was trying not to enter this meeting bitter or with a superior attitude. After all, it was a week earlier I was kissing another man in front of him. I wasn’t above him in any respect.
He talked about his business partner who was in the news at the time. Because I stay well-informed, I knew a lot of the story about the man’s current situation that Smiles did not. So when he was complaining about the man not getting back to him, I informed him of the news of the day and his new partner’s involvement in it. He was shocked to learn some of the details I knew. We were about to break up, and I was still keeping Smiles up-to-date on the goings on in the world at the time.
When that conversation got stale, Smiles kicked off the “us” conversation. He led with his thinking on the “situation.” He told me he recognized he wasn’t putting as much of himself into the relationship as he could have and how that wasn’t fair to me. He pointed out his priority of focusing on his career currently, and his schedule didn’t allow for a relationship. He acknowledged the possibility of his being partly responsible for my actions on New Year’s Eve. Over more conversation, I realized he thought I might have been acting out or doing it on a subconscious level.
I reiterated for him how little of the end of the night I remembered. I was on the verge of tears as I explained this to him. I told him I never would have done it had I been sober. I told him I didn’t initiate the kissing, but I also didn’t stop it immediately. I told him that I would like to think I stopped it relatively quickly, but I have no idea because I don’t remember a single moment of it. I think Smiles wanted to know the motivation for the make-out session. He half asked a question and then stopped when he again realized I didn’t recall any of the end of that night. I apologized emphatically and acknowledged how horrible what I did was. I choked up as I told him it was one of the worst things I’d ever done in my life. I could see that it did in fact bother him. The morning after, he told me he was okay with it, but now, I knew he wasn’t.
Sadly, it made me feel a little better knowing it upset him. It showed that maybe he, on some level, actually did care about me, even if just a little bit. At least I knew he felt something toward me.
I transitioned into more conversation of how we would move forward. I told him I was pretty much on the same page as him as far as ending our relationship. I told him I wasn’t getting enough of what I was looking for from him, and it was a direct result of his priorities.
I told him how hurt I was that he would just drop me after three months. I really stressed that point. I told him I felt so disrespected that he would just stop texting and calling like a switch, as if I wouldn’t notice or I would be okay with it. It really did hurt, because in my mind it nullified our relationship. It showed he didn’t respect it enough to give it the attention it needed, even if it was coming to a close. He told me it was because he needed time to think about what he really wanted and how he wanted to proceed. I told him he didn’t need to cut me off while he thought about it, and he acknowledged his fault.
In the end, we were fine. The whole conversation lasted roughly a half hour. He was on task and had things to do, so when the conversation was winding down, he stood and said, “Shall we go?”
We walked outside and began to part ways. I turned back and said goodbye. I also told him to call me to grab dinner sometime. Just because we weren’t dating didn’t mean we couldn’t be friends. He responded, “Sure thing sir.” I thought that was an odd response, but I’ll take it.
It was an amicable breakup. I’m not sure if I got the closure I needed. I still felt like he used me and doubted if he ever really cared for me. I never got an answer if my suspicions were true. I wondered if he’d been with other men while dating me. I wondered if he met someone else. All questions I would never get answers to. I think that is the hardest part about a breakup — The blow to the ego. We take fault and feel there is a flaw in ourselves, even if that’s not the case at all.
I would recover from this breakup relatively quickly, but I certainly would walk away with a few new scars and a few pieces of luggage to my baggage pile. I would try not to let it affect me too greatly, but then again, you can only control your emotions so much.
Hopefully, as one door was closing, another would soon be opening…
Follow @onegayatatimePocket Gay
Posted by One Gay at a Time in Gay Dating on February 15, 2012
Things with Smiles had soured, and I was already getting back into the dating game. I found a guy who I thought I’d have a connection with on Grindr and set up a date. When the date didn’t go swimmingly, I made my way home.
I was horny — Really horny. Smiles and I had a sparse sex-life. This could quite possibly be a result of my inability to climax at the drop of the hat, or it could have been a result of something else. Regardless, I was hungry for some good sex. I’d come close a few nights earlier to succumbing to the temptation of a Grindr booty call, but in the end, I behaved myself. I hopped on the computer and managed to take care of myself.
Tonight I wouldn’t be so well behaved. I knew I could find a guy to selfishly pleasure me without much effort on my part, both in the search and in the bedroom. This may sound disgusting to some, but we are all animals when you get down to it. We have sexual desires and drives that need to be satiated. I held no loyalty to one man at the time, so I felt no guilt. The other guy would be quite aware of what he was getting into — A one-night-stand.
I didn’t always have this mindset. In fact, I can specifically remember a conversation I had with N about sex and relationships. At the time, I didn’t believe I could have sex without having an emotional attachment to. He didn’t have the same mentality. I found it ironic since I was further along the gay timeline than he was. I would have thought our positions would have been the opposite. Obviously, if you read my blog, you know my position has changed. I know I am capable of having sex outside a relationship.
I’m not proud of this, and this is far from and ideal situation for me. However, at times, my animal instincts take over and my libido craves for satisfaction.
On my walk home, I fired up Grindr. I began chatting with a few people, but there wasn’t much talent. One of the guys seemed decently cute, but I wasn’t sold just yet. I was still on the hunt. We talked a little bit, and I realized we’d spoken a bit on adam4adam.com.
I hit up a bunch of other guys. I was tempted to hit up one of the two friends with benefits I’d established over the summer, but better thinking kicked in. I didn’t want to open up that can of worms again.
When the night was drawing on, I decided to settle for the decent guy on Grindr. He was a really nice, genuine guy. I could tell he’d been judged for his smaller stature based on his adam4adam profile. I felt a connection in our current lack of self-esteem.
We talked a bit more about what the night would entail. It was getting quite late, and he wasn’t thrilled with having to trudge around Hoboken late in the night. I did the unthinkable. I told him to come over and said he could spend the night.
When he arrived, he came directly to my room. I was a little disappointed. He looked better in his pictures, and he was quite small, but I looked on the brighter side. I really enjoyed feeling strong in the bedroom, and it meant I could toss him around a little bit. We casually chatted while I sat on the bed, and he removed his coat and shoes. He joined me on the bed, and we began to make out.
We had protected sex and both of us rather enjoyed ourselves. I showered and then invited him to do the same before going to bed.
When I woke in the morning, it was a bit awkward. I had to go to work, but I also had to get rid of him so I could get ready. I woke with enough time to do both. I politely hinted it was time for him to go so I wouldn’t be late. He quickly got the hint, but he wasn’t going to leave immediately.
He decided to give a parting gift. He climbed down under the sheets and started pleasing me orally. He was good. He was very good. Surprisingly, it didn’t take long before I finished — For the second time in less than twelve hours. If this kid was more my type we surely would have started a thing that morning. He surely knew my libido and how to satiate it. Morning is when I am horniest, and the fact that he just went for it really got my engine revving.
I hopped in the shower while he got dressed. After my shower, I escorted him to the door. I was trying to avoid my roommate from seeing him, but I failed. I gave him a gentle kiss at the door and said goodbye. My roommate then said, “I guess the date went really well last night.” I didn’t feel the need to lie, but I didn’t want to get into it. “He wasn’t the one I went on the date with,” I added with a grin. And with that, I simply walked away.
I texted him that afternoon thanking him for coming by and telling him I had a good time. Later, he texted me saying, “Me too :). Do you wanna grab dinner or something sometime? If you aren’t interested or were just looking for a one-time thing, I’d totally respect that. Not trying to sound crazy. Haha. You just seem like a really nice guy, so thought I’d ask.” Apparently, I’d done it again. A guy who knew he was coming over for a hookup wanted more than just sex. I wasn’t interested in him for anything else, so I let him down gently. “Gonna be honest with you. You deserve at least that. Just ended a relationship this week, so I need to figure out me right now… Make sense?” He was quite classy and responded, “Absolutely man. Sorry to hear. Mine ended back in September. Dated over a year. It’s rough. Hit me up sometime :).”
I did need to figure myself out a bit. But, there was no reason I couldn’t do that while simultaneously playing with “Mr. Right Now” and searching for “Mr. Right.”
Follow @onegayatatimeValentine’s Gay
Posted by One Gay at a Time in Gay News on February 14, 2012
I feel guilty even acknowledging this “holiday” on here, but I also feel I shouldn’t ruin it for those who don’t agree with my stance.
Enjoy the day. Hopefully you have someone in your life to make today special for you both, but also realize that when you’re in a relationship, every day should be Valentine’s Day!
Maybe Cupid will come and strike me with his arrow…
Follow @onegayatatimeOne Gay at a Ty
Posted by One Gay at a Time in Gay News on February 13, 2012
Now that the Smiles Saga is winding down, I thought it would be fun to periodically share with you some of the content I come across I really love. So today, I’m going to have a guest post for you.
I am a big fan of this Ozzie. He’s been a dedicated reader of mine for some time, and we’ve share a close bond now. He’s got a pretty level head about him, but he’s still a real human being with real feelings, flaws, desires, etc.
As soon as I read his post, I loved it so much I immediately reached out to him and asked if he would whip something up for me. I know this will definitely skew toward my homosexual audience, but I assure you, I will have other guests that cater to a larger audience in the future as well.
So, it’s time to shine the spotlight on my good friend Ty-Curious. If you like what he’s written here, be sure to check out his blog: ty-curious.com.
Remember to scroll down if you want to see today’s regularly scheduled post.
Enjoy!
Why Penises are like Presents
**Warning, today’s blog is quite graphic so if you are underage, easily offended or a family member of mine you probably don’t want to read on**
It may be my inner slut but when I make out with a guy I immediately begin to wonder what his penis looks like. Is it big or small, thick or thin, cut or uncut, straight or bent, good-looking or ugly. There are so many different combinations of all these different attributes that you almost never know what you’re going to get!
I have come to think of seeing a penis for the first time like unwrapping a Christmas present. Unwrapping a package to reveal something good makes me super excited and I can’t wait to use my new toy! On the other hand it can also be like receiving a bad present when you unwrap the package to reveal something very disappointing and you have to pretend that you like it!
Like there is gift giving etiquette there is also penis etiquette. Here are some of my rules for gift giving.
1, Don’t open too many presents. If you open presents every day it will become boring and lose it’s excitement.
2, Don’t let too many people unwrap your package. Nobody wants a gift that everyone else has already played with!
3, Make him wait! Remember when you were little and you spent days or even weeks shaking that gift under the Christmas tree in anticipation of the big day? Excitement builds over time, use it to your advantage to build excitement over your package.
Do you have any more rules? Let me know yours in the comments!
— Ty-Curious
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 