Posts Tagged sexting
Juggling 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 @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 @onegayatatimeA Lovely Morning
Posted by One Gay at a Time in Gay Dating on December 14, 2011
Saturday went by and I didn’t talk to Smiles all that much. I was disappointed about being rejected and was still wondering if it was my own issues preventing us from getting between the sheets.
I sent him dirty text messages (not me in the picture) when I woke up about what I wanted to do to him, and surprisingly, he was responding positively. I couldn’t understand why he would be playful over text, but when push came to shove, I got the cold shoulder.
I wasn’t going to give up on him over this. Sex is important, but it’s certainly not the end all and be all of a relationship for me.
He invited me to come into the city to grab brunch with him and a friend. We made plans to spend a majority of the day together. I was on a mission to seduce him once again. After my chat with Boston, I was ready to broach the subject if I was denied once again.
I decided to resort to one of my old tricks. I started watching porn to get myself excited and raring to go. I thought I could use the material if I got to a place of desperation.
And with that, I hopped on my motorcycle and rode into the city through the Holland Tunnel. I parked on the street and walked up the stairs to his apartment. I brought an extra helmet with me so I could throw Smiles on the back if we were traveling around the city.
He decided we should walk to brunch since it was such a nice day, and we weren’t in a rush. We stopped at Starbucks to grab coffees while we walked. As we made our way to the West Village, we popped into a few stores, from clothing to eyewear stores.
Our destination was a familiar one. Smiles’ friend was meeting us at Extra Virgin. I had no idea who this friend was, but Smiles told me I probably met him previously at his birthday gathering. The three of us arrived at the restaurant around the same time. We all sat at a table in the back corner. Indeed I had been introduced to the friend previously, but we only chatted briefly.
Ironically enough, I couldn’t tell which team this friend played for. It wasn’t until he asked advice about a woman I realized he was heterosexual. There was nothing flamboyant about him, so it was no reflection on him that I couldn’t tell. It was more of a guilt by association thing.
He was a really nice guy, and I was thrilled to be included in the conversation throughout brunch. I am good at diving right in, but when two people in a group of three have a strong long-standing friendship, the third can be marginalized at times. This was not the case. The friend was quite interested in what I do as he works in a similar field of communications.
When brunch was over, we said goodbye to the friend. Smiles and I were on the hunt for a branch of his bank make a deposit. In the meantime, we hit up a few stores and walked around most of SoHo. Smiles was scoping out every bakery we passed along the way. I could tell he wanted something to satiate his sweet tooth. I was egging him on as we walked, but he resisted.
Finally, we made our way back to his apartment. I had been getting calls and emails from work all day. It became necessary for me to go into the office. Luckily, I had the motorcycle in the city with me, so I could shoot up there quickly without issue.
Smiles had plans to meet a friend about a business proposal over coffee, so I told him I would give him a ride on my way to my office. He got changed while I waited, and we were off.
I always like having him on the bike behind me. He’s the first guy to truly embrace the situation. He always inches forward on the seat so he’s right up against me, and he tightly wraps his arms around me. I relish every minute of it. When we stop at a traffic light, I make it a point to rub his leg or grab his hand. I find it romantic ironically enough.
I had to spend about an hour at the office, but the second I was able to leave, I darted back downtown to Smiles’ apartment. He’d already been home from coffee, and I couldn’t wait to be with him again. He really did make me happy. I was also very horny. The porn from the morning worked to get my engine revving, and I was ready to get busy with him. I wanted him in the worst way — Traffic could not move fast enough…
After sitting in tunnel traffic near his apartment, I finally arrived. I rang the bell and climbed the stairs hoping to find a happy ending once I reached the top…
Follow @onegayatatimeAm I Broken?
Posted by One Gay at a Time in Gay Dating on December 13, 2011
The following topic of conversation is very embarrassing and very personal. It’s not easy to talk about, but I have a strong feeling I am not the only one who suffers from the issue. Warning: It may make some of you uncomfortable. I am exposing myself in this post, but I feel I need to face my demons to be able to get over them. I also feel guilty writing about this, because it’s a bit of an invasion of privacy for others, but I also feel it’s necessary if I’m being honest with myself and this blog. I wonder if someone out there may have insight to help me and others with this predicament. I feel the need to shine a light on this issue, as no one is talking about it.
My intentions were obvious this time around with Smiles. My hand was down his pants fondling him until I was pushed away with a grunt. There was no misconstruing my intentions. After being denied sex yet again by Smiles, I felt the need to consult my council.
I called Boston for his take on the situation. I explained being denied sex on more than one occasion. His immediate response was, “Oooooo. That’s not good. Something isn’t right.”
I responded, “I know, right? I just wanted to make sure I wasn’t making a mountain out of a mole hill.”
We chatted about the issue, and he told me I needed to address the issue. “Sex is an important part of any relationship, and based on what I read in your blog, sex is important to you,” he added. We discussed the best way to bring it up. The main consensus was waiting until the relevant situation arose. He suggested I don’t bring it up over dinner. If I was denied again, I should bring it up immediately to find the root of the problem.
This was the point in the conversation where I made a small confession of my own. I was worried I may have been to blame for the quantity. I explained my climaxing issue to Boston for the first time in full detail. I told him, while I’d been with Smiles a few times, I had yet to climax. This was through no fault of Smiles. This was a common occurrence for me dating back to the days I was with Broadway. In fact, I feel it was a large part of the reason we broke up. It put a lot of strain on the relationship. He took it personally, even though I assured him it had nothing to do with him. I was still quite attracted to him and still received pleasure from sex, but I wasn’t finishing.
I never was able to find the root of my problem. For a while, I hoped it would fix itself. When it didn’t I explored a number of theories. The leading one being I hardwired my brain to function in a specific way in relation to sex.
For 16+ years, my main outlet for my sexual frustrations was viewing gay porn and pleasuring myself. I wasn’t dating men, and I wasn’t exactly a lady killer either. I would go home, open the laptop, and take care of myself. I worried my brain was hardwired to react only to that stimuli.
I wanted nothing more than to “fix” this issue. For some time, I masked it by prepping myself. If I knew Broadway and I would be having sex, I watched porn before I saw him to build up a “spank bank.” I referred to this when he got me close to finishing to get me over that last hill. It worked for some time, but eventually that solution lost its effectiveness. That’s when things got really bad. I got so stressed about it, when the moment came, there was nothing I could do but think about my lack of performance. I was so wrapped up in the issue, there was no unwinding me at that point.
I had many frank discussions with Broadway on the subject. After discussing it, we agreed not to talk about the issue for some time. It was the only way I was going to be able to relieve some of the pressure I was putting on myself. Eventually it did the trick, and I had my happy ending. However, it wasn’t a 100% solution. Most of the time, I was only able to cum after he performed oral sex. A majority of our relationship, I never climax from anal penetration. The issue was still there. It was just lessened.
It wasn’t as big an issue with San Francisco because we were an entire country apart. When I was physically with him out in San Francisco, I had no issue. When we Skyped, it took slightly longer, but eventually I climaxed. After San Francisco, I slept with a handful of guys. I specifically remember it being an issue with The Trainer. I know it’s not an issue of physical attraction, because he had a body like a god! However, I had to finish myself off that time, and it took some time.
When I was dating N, it took a long time, but I almost always finished. He started noticing my “condition” as time went on. We discussed it lightly, but I think he was under the impression it just took me a little longer than most guys to finish. As I’ve said before, I had to resort to my “spank bank.” Many times, what I was imagining involved the two of us. I wasn’t even imagining porn stars. It was the two of us in different scenario/locations other than in my bed.
Over the summer, it wasn’t really and issue for me. I had no strong connection to the guys I was sleeping with. It was purely recreation and my own need to get some crazy out of my system. I had no pressure or image to keep up. I was just having fun, and it worked.
The first time Smiles and I had sex, I bottomed. No matter who I have been with, I have never finished from bottoming. It has its pleasures, but it never had that effect on me — Hence my status as a preferred top. With Smiles, there was one time when I was very close during oral sex. I was right there, but I just couldn’t close that final gap. After we had sex other times, and I still didn’t finish, I began to morph my theory.
I have a very high pain threshold. Because of this, I wonder if I am in turn cursed with a high pleasure threshold. Maybe it takes more to get me off. I also wondered if my stimulation comes from something more visual. Maybe I need to witness the penetration to climax. Again, these are all just shots in the dark, no pun intended, but I want nothing more than to figure out this enigma. However, I haven’t been able to test my theory at this point.
Smiles expressed his interest early on to work with me to figure this out. It meant a great deal to hear him verbalize this to me. I need someone who can be understanding and patient with me if I’m going to lick this thing.
After I talked to Boston, after a drunk night at the bar, I discussed in length with D my issue. This was really tough for me because I am so embarrassed by the situation. It makes me feel like less of a man. He was helpful in our discussion and helped me feel more comfortable talking about it.
I also called to Broadway. I didn’t exactly feel comfortable talking to him about the details of my new relationship, nor did I think it was fair to him. But, he had experience with this issue. He knew what was going on with me, and maybe now that we weren’t together, he could help me find the key. When I told him I was being denied sex, he immediately said, “Something’s wrong! That’s not normal. You need to talk to him about it.” Everyone was telling me what I already knew, but not what I wanted to hear. In thinking I was partially responsible for the situation, I brought up my issue. Maybe he was avoiding sex with me because I couldn’t finish.
Broadway told me I needed to stop being so stupid about it. I was stressing myself out over it, and that wasn’t going to solve anything. I needed to acknowledge to myself the issue and go see someone about it. I told him I had been entertaining the idea of going to see a therapist, but it takes a very special type of therapist for such a sensitive issue. It wasn’t exactly the easiest thing to find in the yellowpages. He again just indicated I needed to talk to someone about it if I wanted to get over it. He also reminded me I needed to talk to Smiles directly about why we weren’t having sex more often.
The next morning when I woke, I sent Smiles a message detailing my desire for him to be in the bed next to me and how horny I was. He responded positively and seemed he would have been up for morning sex had he actually been there. I was surprised considering a few hours earlier I was denied.
We made plans for Sunday, and I went on with my pondering my issue for the rest of the day. Did he think I didn’t enjoy sex? That certainly isn’t the case. Even if I don’t finish, I still thoroughly enjoy sex and still get a body high from it. Did it bruise his ego to know I wasn’t being fully stimulated by him? I can assure him, it is me, not him. There were a million questions, but no solid answers.
One thing is clear. I need help. I cannot solve this problem on my own, but maybe talking about it with my therapist, Dr. WordPress, will help me face my demons head on and conquer them. Only time will tell…
Follow @onegayatatimePostponed Plans
Posted by One Gay at a Time in Gay Dating on December 6, 2011
On Thursday afternoon, I made plans with Smiles to go out with him Friday night. We planned to grab dinner and then go out the bars for a night on the town finally. However, that plan would have to be postponed.
Thursday night, he sent me a text explaining he forgot he had dinner plans in Brooklyn and then a birthday gathering in the West Village. He quasi invited me, but added, “That’s probably not exactly what you meant when you said night out on the town,” he added.
I suggested we simply postpone our plans one night. It was still relatively early in our relationship, so some space can sometimes help. I didn’t want him to get tired of me. I would use the time to go out with my friends since I was spending many of my weekends with Smiles or traveling.
Friday, I went out in Hoboken with my friends. He texted me to tell me he got a new phone. I was thrilled to know he was thinking of me even though I wasn’t with him (Or, at least that is what was going through my head as I read it).
Saturday morning, I woke and was feeling very productive. For quite some time, I wanted to trek down to the Financial District to check out the Occupy Wall Street movement in Zuccotti Park. I wanted to take the nice camera from work with me to snap some cool shots of the protestors. I didn’t want to do this alone. It was something Smiles and I discussed many times. I tried texting him and then eventually called him to see if he would join me. He was doing work, so he wouldn’t be able to join me until later in the day.
Since I knew he was by his phone now, I sent him a sexy picture of myself from the summer with the caption, “Wanted you to have a sexy picture for your new phone.” He responded, “Haha. Love it!”
I tried a few of my other friends to see if they’d tag along, including LES. After much convincing, I was able to get him to join me, but under one condition. I had to come by his place to smoke first. I agreed and also proposed we use up my Groupon that was expiring that day.
When I finally got to LES’s place, we smoked and got on our way downtown in a cab. The sun was setting quickly, so I proposed we just grab something quick for lunch instead of using the Groupon.
We got downtown to the Occupy movement, and we began exploring. I took many pictures and was even approached by an editor from The Suit Magazine asking me to send her some of my shots. She was looking for pictures to use in an article.
After we had our fill of protestors, we made our way to Wall Street. While walking, LES said to me, “So what’s the deal with this other guy? How old is he? What does he do?” I knew exactly what that question was. I interpreted it to mean, “What does this guy have that I don’t? What makes him so special.” It was an awkward moment, but it was bound to come up at some point. I really liked Smiles, but I also really enjoyed LES’s friendship. I didn’t want to create too many waves or hurt anyone’s feelings. When we got to Wall Street, we found they were filming Batman, and we wanted to check it out. By the time we got there, they were cleaning up the “set.”
As I was walking LES home, Smiles called. He finished work and was ready for dinner. I wanted to go home, shower, change and drop off the camera before we went out. I told him I would meet him for dinner later, and we made plans. I felt very guilty having that phone call with LES walking next to me.
After I cleaned up and changed, I met Smiles in Chelsea for dinner. We had no location picked out, and ended settling on Elmo for dinner. Conversation during dinner was great. He had a very productive work day, and I feel he let me in even more. He was opening up more and more every time I saw him. We were finally peeling back the layers of that onion.
After dinner, he proposed we go over to Barracuda. I’d never been and have always been leery of it. I’m not a fan of gay bars. They make me uncomfortable.
When we arrived, I learned he knew two of the bartenders. I had met them before as well. They were both very good-looking and pretty unforgettable. They were at Smiles’ birthday gathering. Barracuda wasn’t anything like what I expected. I was expecting a flashy club like seen, not a dive bar. I immediately felt more comfortable.
That is until a tall overly friendly black man came up behind me and started feeling up my chest with his arms around me. He was a feisty one, and I wasn’t interested. I made that pretty clear by my extremely uncomfortable facial expression. Smiles on the other hand was playing ball. I assumed it was a friend of his, until I learned he never met the guy before. This was just Smiles being his charming self.
Because I wasn’t completely comfortable, I drank a little more excessively than I should have. On top of that, Smiles’ ex arrived. I had no problem meeting him and talking to him, but I did have a problem when Smiles said to me, “I hope you don’t mind, but I’m going to steal away with [him] for a minute. I haven’t seen him in a while, and I need to chat about some things.” Based on the interaction, I wasn’t worried that he was going to do something with his ex. I was more annoyed I was being ignored in a place I’d never been before where I wasn’t completely comfortable and knew no one else.
I entertained myself by watching the bartenders cutting off the tall black man because he was being obnoxious to everyone at the bar. However, for me, the drinking continued — In excess! I drank so much, the bartender started giving me free drinks. I drank my face off. I was hurt and p*ssed. This little chat went on for a long time. There was some flirting and maybe Smiles wasn’t 100% over him, but I was okay with that. It’s natural. I wasn’t okay with being ignored! When the conversation ended, Smiles said to me, “How come you’re so quiet?” What the hell was I supposed to say to that? — “I’m quiet because you just ignored me for the past half hour?”
Next thing I know, when I woke up in his bed, the first thing I noticed was I was naked. I never sleep naked. The second thing I noticed was some lube on my backside. I couldn’t for the life of me remember anything about the night before. I don’t remember much after that. I don’t remember getting my coat from coat check. I don’t know how we got back to his apartment. I don’t remember climbing into bed.
I racked my brain to remember anything from the night before. The only thing I could conjure up was a flash of about ten seconds of sex with him on top of me. It was a very scary feeling! I’d blacked out before, but never have I blacked out sex. I was the only one ordering my drinks all night, but I couldn’t 100% rule out the possibility someone roofied one of my drinks.
I never mentioned to Smiles my panicky thoughts. There is no chance in hell Smiles would have done that to me, so I wasn’t worried in that respect. I knew he would never take advantage of me. I was probably pretty lucid in my drunken state, if previous history has anything to say. I was worried I may have done something to embarrass myself. I decided to play it cool and pay close attention to how the rest of the morning progressed…
Follow @onegayatatimeEvery One But the One I Want
Posted by One Gay at a Time in Gay Dating on November 22, 2011
Friday arrived, and I was starting to nail down plans with Smiles for the night. He had things to do all day, so we planned to grab dinner and then head to his friend’s birthday party.
This meant I had time to kill after work. My good friend A asked me to grab happy hour drinks with her. She recently moved our of Hoboken into the city with her boyfriend, so I was already seeing a lot less of her. We were due for a catch-up.
She picked a place in the Flatiron District that’s known for their happy hour. We cozied up to a spot at the bar and chatted about our new situations. It had been a while since I caught her up on the status between Smiles and I. I took her for a ride on the roller-coaster ride of emotions I’d been through. She gave me advice on how I should proceed and things I should watch out for. After five years, she knows me quite well and can predict a lot about me, so I’ve come to listen intently to what she says.
She also took the time to talk about the new challenges she faced moving in with her boyfriend. I tried to give her my two cents for what it was worth. My biggest advice to her was to pick her battles. On the things she could let go, she should, but on the things she really cared about, she should make a stink. That way, he would realize with more poignancy when he was doing things that got under her skin.
In the middle of our conversation, Smiles called to discuss dinner. He chose a place about two blocks from where we were drinking, and we agreed to meet in a half hour. When the time came, and A and I had our fill of cocktails, we walked to the restaurant Smiles chose. I coerced her into coming along to meet him since none of my friends had the opportunity yet.
I introduced them to each other, and Smiles invited her to join us for dinner. A had plans to meet her boyfriend for dinner, and I could tell she was looking for a quick exit, so she agreed to sit with us for a few minutes. She was already running late. I appreciated her making the extra effort, and gave her the out she needed. I told her to get on her way.
After she left, the conversation with Smiles was slightly forced and awkward. I was having a hard time breaking through and there were periods of silence. I learned he was feeling very sick and his stomach was bothering him. He had issues with his appendix, and it was inflamed and bothering him again.
Now, I was worried. I genuinely cared for him and my paternal instincts kicked in. I was worried for his safety and said, “Don’t be a hero on me here. If you aren’t feeling well, we can go at any time. Don’t soldier on on my account.”
“Thank you for your concern, but I’ll be fine,” he replied.
The rest of the meal was pleasant, but quiet. I reached my hand under the table to rub his knee to try to make a better connection while we chatted. That, and I was still worried about his condition.
When we finished dinner and desert, we had some time to kill. Smiles walked around the neighborhood looking for a massage parlor (legit, not sexual) in which to kill time before the birthday party. We couldn’t find one still open to take advantage of, so we hopped in a cab and made our way to the party.
When we arrived at the party, I was slightly overwhelmed by the crowd. I’d never been to a party so heavily skewed male in my life. I learned the birthday boy was gay, which answered a lot of questions for me.
We found a comfortable spot to plant ourselves and each grabbed a drink and something to nosh on. We made a friend and chatted with him a bit. He was an extremely jacked and cut black man who is an interior decorator. It was interesting hearing him talk about his occupation, all while looking at someone who looked like a personal trainer.
After some time, this man turned to us and said, “Oh. Are you two together?”
Both their eyes focused on me. The pressure was on. I didn’t know what answer Smiles was looking for, but I saw this as an opportunity to gauge his reaction. I tilted my head slightly to the side nodding and said, “Yeah.”
Our new friend called attention to and questioned my head tilt heavily. I pointed out we didn’t know each other all that long. I still look back and wonder if Smiles was actually looking for me to say yes. I still wonder if he was being distant because he thought I wasn’t fully invested in our budding relationship. Of course I wanted to say yes, we were dating, but I didn’t know where his head was at the time. I didn’t want to scare him off by being overzealous.
We were nearing the time to head out for the night, but I needed to use the facilities first. That was particularly a challenge because the bathroom was being used by a few to sign a birthday book photo album. Finally, I gave up and assumed I could go when I got back to Smiles’ apartment.
We went downstairs and hopped in a shared cab with one of the female guests from the party. As we progressed, I learned I would not be going back to Smiles’ apartment. My destination was the PATH to go home. I was slightly shocked and annoyed. It was a Friday night. Why wasn’t I being invited back to his place. I know I’d never been there before, but this was a bit ridiculous. It was around midnight, and I was dreading my trek back to Hoboken.
He hopped out of the cab with me. We said goodbye on the street with a quick kiss, and I was on my way home. I’m not gonna lie. I was hurt. I felt rejected. There was only so much rejection I could take.
As I walked, I pulled out my phone. I called Boston, but of course, he was still ignoring my calls. I left him yet another voicemail. I also called my new friend to see what he’s been up to. No answer either. Finally, I texted the Principal. It’d been a while since we chatted, so I thought I’d given him enough space. We began texting, but I told him I’d have to continue the conversation on the other side of the river.
While waiting for the PATH, I nearly p*ssed my pants. The train going into the city dropped off a tranny who felt the need to flirtatiously wave at me and say hi. When it finally arrived, I leaned my back against the wall and closed me eyes to concentrate on something other than my bladder. Two women were in front of me on the crowded train, and around a turn, one fell into me. They started arguing with each other and engaged me in conversation. Though not stated outright, I learned they were a lesbian couple, and they were hot. We had a long conversation, and when we arrived at the Hoboken stop, they invited me to come hang out with them. They had no idea my preferences fall in the men category, and they were inviting me back to their place. I used my bladder as an excuse and said goodbye. It was early enough, but I was not in the mood to play.
While speed walking home, a very large black girl grabbed my arm, pulled me towards her, and shouted, “TAKE ME HOME WITH YOU!” I ripped my arm free and continued to walk home, all the while texting with the Principal. I was flirting slightly, but not to the point of crossing the line with him. I missed talking to him and our flirtations. I really did like the guy, but the distance was still killer.
When I got home, I relieved myself and hopped into bed. I was disappointed I was there alone, but I opened up a whole new can of worms with the Principal. He still wasn’t over me, and I just scratched open that scab again. I even went as far as to pull up Grindr again for the first time in over a month.
It was just my luck. The one I wanted to be spending my night with just sent me on my way, while everyone I didn’t want anything to do with seemed interested in me.
Furthermore, I wouldn’t be seeing Smiles the following day. Originally I was planning to go to a horse race in New Jersey and invited him to join. When the day was approaching I was no longer interested in going and sold my ticket. I was hoping to spend the day with Smiles, but I learned he was going to Six Flags with friends — without me. I understand he has a life of his own, and I don’t have to spend every waking moment with him. But at this stage in our relationship, I wanted to spend more and more time with him. I certainly would have invited him on a fun trip such as the one he was going on. Apparently, he didn’t feel as strongly for me. A clearer picture was being painted for me. Maybe he just wasn’t that into me.
I realized things weren’t going as smooth as I would have liked, so I set myself on entertaining other ideas…
Follow @onegayatatimeFillet Mignon and Baked Potatoes
Posted by One Gay at a Time in Gay Dating on November 18, 2011
After breakfast at the hotel, we got back on the road to my great-aunt’s house in Mount Vernon to drop off the keys and make our way home. It was surprisingly fast.
I was really disappointed I never got to chat much with the bride. It’d been years since I’d last seen her, and we only speak on the phone about once every four or five months.
During the whole ride, I had a lot of time to think. For me, this is deadly. When I have time to think, I crawl up into my own head and start digging around where I shouldn’t be digging — This is why I lead such an active lifestyle. Thinking depresses me.
A lot of thoughts about Smiles were going through my head. I was a little hurt and upset my advances were rejected in the morning. I also was very disappointed I didn’t get to grab brunch with him. Overall, I guess you could technically deem the weekend with him a success, but I still wasn’t thrilled. I was on unstable ground. I had no idea where I stood with him, and it was getting to me. As usual, I was over-thinking everything.
When we got back to Hoboken, we stopped at the grocery store. I decided to call Smiles to see if he wanted to come over that night. I wanted to make him a nice home-cooked meal since he never cooks for himself. We always go out for dinner or order take-out. He agreed to come by. I also had ulterior motives. I wanted make-up sex for Saturday morning when I was denied.
That evening, when he got off the PATH, I hopped on the motorcycle and rode down to pick him up. I was happy to finally get him out on the bike. He’d been on one before, so it wasn’t as exciting as the first time I’d taken motorcycle virgins on the bike, but it was nice to have him so close to me. We rode back to my apartment with his arms tightly around me. I thoroughly enjoyed it.
I started us off with some artichokes while the fillets finished grilling and the rest of the meal finished cooking. I made more food than the two of us could possibly finish. When we had our fill, I cleaned up, and we made our way to my bedroom for the night. He asked if he’d be spending the night. “Of course you’re spending the night! Did you think I was going to kick you out now?” I responded. “I don’t know. Some people need their rest before Monday morning,” he said. I reminded him the size of the California king bed and assured him he wouldn’t disturb my slumber. If anything, he would enhance it.
Warning: The following may be too graphic for some. I started getting frisky. After not getting any the morning before, I was even more geared up for some great sex. We undressed each other and jockeyed for position once again. I wasn’t making the same mistake again. I made sure I was in position to top this time. When I pulled out my night-stand drawer to get a condom and some lube, he made a comment about the large dinner and not sure it was a good idea. I surrendered, and we decided to use alternate methods. He climbed on top and used his hand behind his back. I was impressed with his ingenuity and his willingness to try alternate methods. However, it wasn’t quite enough for me. It felt great, but I couldn’t quite get over the final hump, as is my issue often.
We stopped and just enjoyed each other’s bodies laying next to each other before we both cleaned up and hopped into bed.
When I woke in the morning, I snuck quietly into my bathroom to shower so he could fall back asleep. If he wanted, I was going to let him sleep as long as he wished and just pull the door shut behind him. However, he had a few things he wanted to get to Monday morning, so he joined me on my morning commute.
We casually walked to the PATH and hopped on. When the time came for him to get off, we exchanged a quick kiss. A lot was going through my mind before that. I was a little afraid to do it because I knew all eyes would be on me as soon as he got off. However, I was the one who initiated it. It was subconscious, but I wasn’t going to let fear of others’ reactions rule my actions anymore. I didn’t care who knew I was gay anymore.
I rode the rest of the way to work not making eye contact with others. I wasn’t 100% comfortable in my own skin, but I was still growing with every day. Things were progressing nicely with Smiles, and they could only get better with added confidence.
Follow @onegayatatimeDinner and a Stroll Along the River
Posted by One Gay at a Time in Gay Dating on November 7, 2011
Following my great date with Smiles, I couldn’t get enough. I relished every phone call, every text, every moment I spent with him. I suppose you could say, I was gaga.
Is Smiles the greatest guy out there? Is he the best guy out there for me? Who knows. I don’t know him well enough to make that assumption. However, my appetite was wet, and I wasn’t satiated. He is a really great guy, and possess a lot of the qualities I seek in a man. I was cautiously optimistic — Fingers crossed.
After our last date, I texted, “Had a great time last night btw :)” He responded, “Me too!” That being said, I asked him out once again. The following day, I said, “So… When do I get to see you again?” He proposed Tuesday night. I was a little surprised. I was waiting to hear Wednesday night, since he invited me to his birthday that night. I was thrilled he was interested in seeing me two days in-a-row. I was just hoping he would confirm for me once again he wanted me at his birthday celebration and wasn’t having second thoughts.
I had been apartment hunting, so when I found one, I sent him a picture. That was followed shortly after by a sexy picture of me I took last summer on vacation in California (you’ll recognize part of the picture in my Gravatar on the right). I thought I’d spice things up a little, especially since I promised him I would send the picture. He responded, “That’s way better than an apt pic!” I said, “I thought you’d appreciate…” However, he didn’t believe me when I told him I took the picture with the timer on the camera. He thought someone else took it until I went on to explain the entire situation. “You’re committed to this, huh? LOL. Good for you. Strong work,” he said.
When Tuesday arrived, I asked him if we were still on for that evening. He responded, “Yep. Barring a trip to the hospital for stitches after I punch my computer for not working and wasting my time today.” At the end of the day, he added, “I’ve calmed a bit, looking forward to seeing you. What time are you off? You don’t happen to have running shoes with you? I feel like I need a run, LOL.” After discussing my lack of running equipment, we decided on dinner at his favorite restaurant, Extra Virgin.
We grabbed a table outside the restaurant. It was that time of year right before it’s not too cold to sit outside, but it’s also not quite warm enough to be completely comfortable. We ordered our food and immediately dove into conversation. We talked about our days and what was new in our lives.
He told me he and a friend were going to a shaman to try Ayawaska (a Peruvian root similar to Peyote) for the first time. He explained the setting in a yoga studio and how it works. I was fascinated. I’m certainly not the type to be open to drug abuse, but recreationally or experimentally, I have an open mind, especially if it happens under close supervision. The point was to relax and open you mind. Many people use it to communicate with God/the spirits in a trippy way. There was slight reservation/worry in the back of my mind regarding the whole thing, but he is an adult. I knew he’d be safe.
We ate our meals (I don’t recommend the chicken pot pie at Extra Virgin, but everything else I’ve had is spectacular) and continued our conversation.
Smiles likes to order deserts when we go out. Going out to dinner is already putting a dent in my wallet that normally isn’t there. I cook in my apartment far more often than I dine out. Since I started seeing him, I was going out a lot more often for dinner. Not only that, it wasn’t exactly helping my waistline. It’s amazing how easy it is to put on pounds when you aren’t afraid of people seeing you in a bathing suit anymore.
Instead of getting desert, he suggested we go to this tea shop, McNulty’s and then grab desert elsewhere. He was looking for a specific tea, so I called the shop to make sure they were still open.
After the tea shop, we hit up a gelato place, L’Arte De Gelato. We took out gelato and walked down Christopher Street to the pier. We had a nice stroll along the pier holding hands. I pointed out a few things on the Jersey side, such as the pier I normally hit up in the summer looking back the other way. We chatted a bit at the end of the pier. I was hoping maybe for a little make out session or some hugging, but I didn’t get the feeling he was interested in that. I don’t think he noticed, but when I went to reach for his hand, that’s the exact moment he lifted it from the railing and turned around to head back to the Christopher Street PATH station. I wondered in the back of my head why he never invited me to come back to his apartment, especially since I knew we were in the neighborhood. But, I also know I needed to take it a little slower. I had a tendency to rush things, and I needed to break that habit.
When we reached the PATH station, we hugged, and I gave him a kiss goodnight. I was happy to get to see him again, and I was cautiously looking forward to his birthday the following night. It was an awkward challenge for me, but I knew I was up for it. Birthdays are always interesting situations, especially when you’re the new addition to the crowd, but something told me I’d be alright.
At the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 