Posts Tagged conversation
Southern Hospitality
Posted by One Gay at a Time in Gay Dating on May 17, 2012
After my lukewarm date with the doctor, I was ready to get back out there in search for a man.
I’m happy to report, which I’m sure some of you may have suspected otherwise, I was doing a great job of staying off Grindr. Granted, it was a short period of time, but I was thoroughly proud of myself. I felt like I’d joined GA. Every day not having meaningless sex was another day of Grindr sobriety.
Tuesday after work, I arranged another date with Southern Drawl. The last date was a bit crazy. Footsie under the table. Shenanigans in the bathroom. I was curious if he’d be able to behave this time or would he be looking for another quick trip to the bathroom.
We texted during the day to lock things down. I proposed The Breslin. I’d always loved their food, their drinks and their ambiance. He shot the idea down because he said the place was always full of hipsters. I had always been a fan of Sala 19 in the Flatiron District, so I proposed we go there for dinner. It worked out well because it was halfway between our offices. He agreed.
I had to wait at work for him to finish. When he did, I made my way south to meet him. I met him on the street corner, and we walked to the restaurant.
Dinner was very nice. He was well-behaved, and the conversation was good. I told him about my allergist appointment, and he told me about his day. We talked frankly about our last date. We discussed what went on. I learned he’d never done anything like that before. I was also learning about the guys he’d dated since living in New York City. When we originally spoke on the phone, I was under the impression he was new to the gay world. I thought he’d never really dated anyone before. Now, I was learning about all the guys he dated in NYC, as well as the guy he dated through college that he said I so strongly reminded him of and resembled. It was a bit unsettling.
In the middle of dinner, he told me he’d ended things with the guy he was seeing. He explained they’d only been seeing each other for two weeks, and things were never that strong. When I probed him to ask if he left the other guy because he met me or if he did it because he wasn’t satisfied with the previous guy, he told me it was the latter, but part of it was also due to meeting me. A big red flag went off in my head. Would he leave me for a better model?
I still wasn’t sure about him. I liked talking to him. I liked being with him. He was smart. He was nice. He wasn’t flamboyant, however, I wondered if maybe he was too “straight.” He was a bit homophobic. I’m not the most open about my sexuality. I’m not out to everyone at work. I don’t openly advertise my sexuality. However, if he wasn’t comfortable with himself, how could we be comfortable with each other. I couldn’t be sure about him. Was he right for me? I had no idea. Only more time could tell. I was keeping a distance as we moved forward. We had a connection, but was it strong enough to last? Was it what I wanted?
In our conversations, his southern entitlement shined through. It was an incredible turnoff. Where was the southern charm I’d seen so many times in movies. When I think of the ideal man, I think of Matthew McConaughey. He definitely has an ego and self-confidence, but he also exudes charm and sexuality. His confidence is not in your face, and he seems down-to-earth. Southern Drawl fit the other Hollywood archetype — The Southern plantation owner. He had an air or superiority that was hard to swallow. Many times, he laughed off these comments, making them seem like a joke, but I wondered if there was really something deep down that was more genuine. I wasn’t ready to date a snob. That $hit wouldn’t fly with me. I wasn’t going to let him get away with it, and I’d already started calling him on it.
When we finished eating, we split the bill and walked north to the PATH station. I said goodbye to him ont he street with barely a hug. He was uncomfortable exchanging a kiss with me in front of a city of strangers. I wasn’t thrilled by that.
On my ride home, I questioned why I was continuing to see Southern Drawl. He was definitely interested in me, and I was still intrigued by him. I wasn’t ready to write him off just yet, but I didn’t see a lot of promise or potential. I would continue to see other men and continue to see him until I was ready to make a definitive decision.
Follow @onegayatatimeHouse Call with the Good Doctor
Posted by One Gay at a Time in Gay Dating on May 16, 2012
In a strike of luck, in terms of my desire to turn my dating/sex life around, the timing of a family trip could not have been better planned. My parents, my sister and I were heading to Virginia to visit my aunt, uncle and cousins. The purpose of the trip was to see the cherry blossoms in Washington DC.
It was a fun trip. I got to see my cousins’ girlfriends and their children, many of which for the first time. Even though the cherry blossoms had already fallen due to an early bloom, it was still nice to get away and relax.
While driving back to New Jersey with my sister, I began attempting to line up dates with all the guys I’d been talking to before I left. As far as going on dates, the trip came at a bad time because it put a roadblock in the momentum. I kept up with the texts from the southern boy I’d gone on one date with so far. We were trying to line up a second date, as well as a few first dates with some other men I’d chatted with.
I got back to town on a Monday afternoon and tried to dive right into the dating. One of the guys I’d been chatting with was a doctor I met on Grindr. We exchanged pictures. He was very good-looking, very well-spoken and very charming. His response to my picture was, “Matthew McConaughey party of one?!” I was incredibly flattered, and suggested he consult with an optometrist friend. Although he had some promise, I wasn’t all that excited to meet him. I was going in with an open mind, but the fact that he was a doctor was somewhat of a turnoff. He would have no time for me, and I have come to realize I need someone who will be around and spend time with me.
We texted back and forth to nail down plans. As the workday was ending, I asked him what he wanted to do. He responded, telling me, “I honestly feel like I need a quiet night in. A bit drained here but would definitely like to have you over for drinks and conversation if you are up for that?” It was a bit unconventional, but I told him I was game. He gave me his address, and we set a time at 9:00pm.
I made my way into the city, bottle of red wine in hand, and walked to his apartment. I called Boston, and he shocked me by picking up. I wanted to hear how his birthday went and catch up. He further shocked me with a story involving an on-duty officer and himself that made me so proud. It was nice to hear Boston letting loose.
As I walked up to his apartment, I hung up with Boston. He lived in a very nice building. He answered the door, and we exchanged hugs. He had a gorgeous place. I came in and made myself comfortable on the couch while he opened the bottle. I felt quite overdressed when I noticed him in sweatpants and a t-shirt. I was jealous. I removed my shoes and sat Indian-style on the couch.
He was far more attractive than his pictures. His tight t-shirt showed off his chiseled body, and his face and smile looked very similar to Taye Diggs. I was slightly mesmerized.
It wasn’t long after we began talking that he let his guard down. The flamboyance came bubbling up, and it was really turning me off. I immediately lost my attraction for him. I could see us being friends, but I could never date someone like that.
We sat on opposite ends the couch talking the whole time. I learned about his job and what he does in his free time (which wasn’t much since he didn’t have much of it). He told me his specialty, and that dominated a majority of the conversation from then on out. Ironically, his specialty was relevant to me, and we got on the topic of safe sex and HIV for over and hour. It was incredibly educational on two levels. I learned a few things about HIV transmission and the disease itself, and I learned how little I know about the stuff I was so cavalier about days prior. I thoroughly enjoyed our talk, but I wasn’t attracted to him as a potential man to date. I would, however, love to keep him around as a friend.
It was late, and I needed to go home. He needed to go to bed. He walked me to the door, and I said goodbye with a kiss. He pulled back and made a comment on how he wished he’d only done that sooner. He really liked it and came back in for more. He was a good kisser too. I walked to the PATH and then walked home, and it took me a while to get there.
The next morning I noticed a text from the doc. “Off to sleep here, but just wanted to say thanks for an awesome date! I really had a great time meeting you.” I apologized for my lack of response and told him I was at the allergist to getting poked with various things to find my allergies. We exchanged small talk on the subject, and the conversation fizzled out. That was the last I’ve heard from the good doctor…
Follow @onegayatatimeRevisiting the Past
Posted by One Gay at a Time in Gay Dating on May 15, 2012
Relationships aren’t easy. No matter whether you’re friends or lovers, each relationship is accompanied by its own set of issues. When you introduce sex into these relationships, things get exponentially more complicated.
Tuesday, I engaged in unprotected sex with M.E. It happened in the middle of the night in the passion of a moment, however, there is never an excuse. People’s lives are at stake. I tell you about the poor decisions and the mistakes I’ve made because I hope you can learn from them.
From that morning on, I was on damage control. I’d already talked to him about what transpired between us, and we agreed to get tested and share our results to ensure we were safe going forward. I called a doctor’s office and made an appointment that Wednesday following work to have an STD test.
As I walked into the doctor’s office, I noticed a few other men sitting in the waiting room. I had never been to this facility before. I was curious if they were there for the same thing I was. I began to wonder what was going through their heads. Were they petrified? Were they already infected? etc. I myself began to worry a little. I wasn’t particularly worried until I walked into the waiting room. There was nothing I could do at that point, so I tried to calm my nerves. The only good part about this was it made me quite ready to fill a cup with my urine sample. They also drew blood and told me to call in three days for my results.
Now, it was the waiting game. I couldn’t do anything and would have to wonder for three days.
That night, I had plans with P to go see Silence, The Musical. After my tests, I walked all the way downtown to meet her for dinner near the theater. Dinner was very nice. I got her caught up on all the latest action in my life. She’s always incredibly supportive, even when I make poor life choices.
We went to the show, and about two minutes in, I noticed how attractive one of the male actor/dancers was. It was a small theater, and any time he was on stage, I couldn’t take my eyes off him. When they came out for curtain call, he caught my eye, and we made eye contact. There was a bit of an awkward moment, but I was crushing a bit.
I wasn’t intimidated because I’d already dated someone who worked on Broadway. This was Off-Broadway. I didn’t think twice about what I was about to do. That night, when I got home, I decided to do some research (and when I say research, I mean stalking). I pulled out the Playbill and looked to see if I could find him on Facebook. Much to my surprise, he was on there. I decided to message him. What the hell, why not? What did I have to lose?
I’m sure you’re wondering who this is, and I really hope this doesn’t come off incredibly creepy. I myself can’t believe I’m about to send you this. (And, something tells me I may not be the first).
First off, I came to see Silence tonight and thought you were incredibly cute and incredibly talented. Your mother must be so proud.
Second off, I have no idea if you’re single or even gay. But gay or straight, single or taken, I’d love to strike up a conversation with you. On the flip side, I fully understand if this makes you uncomfortable.
Anyway, with nothing to lose but a little dignity, I thought I’d give it a shot. Hit me back if you’re interested in chatting some time. If not, enjoy the flattery…
Then, I noticed he was a friend of Broadway, the guy I dated for ten months. I pulled out my phone and texted him to see what their relationship was. His response was, “Who is that?” I explained who he was and how they were Facebook friends. “Oh yes. We audition together. HOT!! You dating?” I told him, “No. I just cold called him on Facebook after seeing his show… LOL. We’ll see what happens. Think I creeped him out?” He felt I did creep him out, but I explained how I had nothing to lose.
Sadly, I never heard back from him. It just wasn’t meant to be.
Much later that night, I received a text from the guy I had sex with when I cheated on N. We’d been texting a bit recently after noticing each other on Grindr. He asked if I was up. I replied, and he asked if he could come over. Apparently, I was getting a booty call. It was about 11:30, but I didn’t see the harm. After all, I did fantasize about the first time we had sex quite often. It was something my mind went back to many times. This isn’t because of the cheating. It was simply because the sex was that good.
He came over, and I could tell he’d been drinking a bit. He immediately commented on how crazy it was that my new apartment looked exactly like my last. He began taking his shoes off before hopping on the bed with me. He immediately began making out with me interspersed with conversation. He never got closure with how messed up things ended between him, N and myself.
He wanted to talk a lot about him. I would have been fine if N never even came up in conversation. I learned they got together once after I told him to take a hike. It was hysterical how much their accounts of this encounter were completely different. The only commonality was how much disdain they had for each other. At one point he mentioned how dirty N was. I asked him to clarify as in physically or as in naughty. He then went on to describe a particular body part that would only have been encountered during sex and how disgusting it was. He then went on to tell me they never had sex. He told me N just gave him a blowjob and he finished on his face. He pointed out his surprise I ever dated N. N’s account of the story was they met on the street. After seeing him, he couldn’t believe I would hook up with someone so ugly, let alone cheat on him with someone of that caliber. All I could do was laugh my a$$ off in my head. These two were ridiculous. I was so happy I cut things off with both when I did.
After the N conversation concluded, he really wanted to have sex with me. He mentioned how amazing it was the last time we hooked up, and he told me he hadn’t had sex with a man since the previous summer. I told him how hot it was last time we hooked up and how I referred back to it many times in my mind. With that, the clothes began to strip off.
Warning: The following may be too graphic for some. We were intertwined in each other’s embrace making out. I found myself lying on my stomach with him on top of me. I knew he would try to penetrate me, but I wasn’t game for that. The last time he did that, I sprang from the bed because he did it with no preparation and full force. I wasn’t about to let that happen again. He tried and tried, and I never relaxed to allow entry. I think he got embarrassed with his fumbling, and he made a comment. I complimented him and told him he was too large for me. We switched positions, much to his chagrin, and now I was the one on top. He was on his back, and I put his legs up on my shoulders.
He told me how much he enjoyed me inside him because I hit his prostrate just right. With that, I slipped inside him. It felt amazing. It was just as good as the last time I played over and over again in my mind’s eye. He loved it too. After a short while, he finished on his abdomen. Seconds later, I alerted him I was about to finish. He replied, “I want you to shoot inside me,” and I did. For me, this was a first, and it felt incredible.
I’m not sure why, but I had no problem finishing this time. It completely came naturally and without over thought. I felt amazing and incapacitated all in one. We lay there next to each other speechless for a minute before even moving or talking. We were in euphoria.
When that wore off, I became the topic of conversation. N told him about the blog when everything went down. He told me he read part of it and still didn’t understand why I wrote it. He also asked this story not make an appearance, but I find it too important to exclude. He pointed out I was looking for a boyfriend, and that was not what he was looking for at all. He pointed out how I was going about things all the wrong way if I wanted to find love. I explained to him all my trials and tribulations and what I was looking for in the end. He fully understood.
Then he made a comment about how stupid we were to not use a condom. I agreed. I’m sure he was far more worried about the situation than I was since I finished inside him. Apparently, with everything I’ve been through, I still didn’t learn my lesson. I wasn’t being responsible.
This was my wake-up call. I’d hit rock bottom. I’d gotten so reckless with my life. I needed to stop before I did something that could end my life. What was I doing? How could I be this stupid? This wasn’t how to find love — Having unprotected sex with the guy I cheated on my ex with. No more excuses. No more Grindr hookups. No more strangers. If I wasn’t finding love, I would be single and celibate for some time until I got myself under control. This was my turning point.
Follow @onegayatatimeSomething We Should Discuss
Posted by One Gay at a Time in Gay Dating on May 14, 2012
Things with Middle Eastern certainly weren’t leaving us holding hands skipping down the beach. I really liked him, but I never really saw the potential for a strong relationship with him. I would like to think I wasn’t leading him on. I would like to think he was well aware we were casual and enjoying each other’s company. But, who could be sure what’s going through someone else’s head?
I invited him to come over for dinner Tuesday night after work. A part of me was horny, and he is really great in bed. Another part of me wanted his companionship — Just someone to watch TV with and cuddle. He was in class and would come by a little later. This worked out because it would allow me time to make us food.
When he arrived, we immediately went into my bedroom and fooled around. We didn’t have sex, but there was a lot of kissing and groping and cuddling. He told me about his day, and I got him caught up on what was going on in my life since I’d last seen him. When we had our fill, I tossed him a pair of my shorts to put on, and we made our way back out to the living room to eat and watch TV. I learned he’d already eaten, and I made a plate for myself, and we sat on the couch watching TV.
When my roommates made their way to bed, and it was getting later, I turned off the TV and led M.E. to my bedroom. We hopped into bed and watched some more TV before we were no longer watching because other desires took over. Warning: The following may be too graphic for some. The kissing and heavy petting led to stronger desires. I grabbed a condom and lube, and we went at it. It was extra passionate this time, We were thoroughly enjoying each other. We went through many permutations of positions. Every one was better than the last. His body felt amazing, and he seemed to really be enjoying it.
I was disappointed he never finished with me, but I fully understood. I’m not quite sure he did. “I don’t know how to explain it. It’s like I have a full-body experience, but I never cum,” he expressed. I told him I knew exactly what he meant. I never brought it up myself, because I knew that was the exact opposite of a solution. In all the times I’d been with him, he never finished. He told me it was nearly impossible for him to accomplish after I penetrated him. We both went to bed that night without finishing. The sex was so great I didn’t feel the need to finish myself off. I was also hoping for some morning nookie, so I knew I would be hornier if I left it til the morning.
In the middle of the night, he did something that woke me up. I glanced at the clock and saw it was nearly four am. He began grinding against me and grabbing hold of my member. He was massaging his backside with it. When I woke, I began to engage in this activity as well. I was grinding on him until all of a sudden I found myself inside him. It was pure bliss. We both enjoyed this in the spooning position for some time before finally withdrawing and going back to sleep.
In the morning, we woke to the sound of my alarm. I had to go to work. He didn’t have any obligations that morning. As I predicted, I woke up hornier than ever. The middle of the night sex had my engine revving extra hard. We engaged in a lot of foreplay. I started orally pleasuring his backside before climbing on top of him and penetrating him once again.
This time, I did not reach for the condom. I know this isn’t the smartest. I let passion get the better of me. In the back of my mind, I trusted him. I didn’t think he was having sex with anyone else. I also know I’d done a lot to make sure I was protected with all the sex I’d recently engaged in. I had no signs of an STD and no reason to believe I contracted HIV.
We let out synchronic moans of pleasure. It felt amazing. We had lots of sex before he needed to take a break. He caught his breath as we exchanged how much we enjoyed sex together. When he was good again. He laid on his back while I lifted his legs up on my shoulders. I enjoyed looking into his eyes and kissing him while we had sex. He was pretty amazing in bed, and I loved his passion. We stopped when he needed a break again.
I didn’t want to be late, but I still wanted to continue the fun. We hopped in the shower and bathed every inch of each other’s bodies. I was still incredibly horny, and I knew I wouldn’t be able to concentrate at work if I didn’t finish. I tossed him down on my bed and pulled his towel off. We got right back into it for a bit before I withdrew and finished myself off. He was thrilled. He really enjoyed all of it, but I could see there was something else going on there. I knew we didn’t discuss the lack of protection, and it needed to be brought up. I was in a rush to get to the PATH to go to work, so I made a mental note to call him later to discuss.
He gave me a ride to the PATH, and I kissed him goodbye. When I got to the other side of the river, I’d received a text from him expressing his concern. He wasn’t worried, but he just wanted to discuss it. I explained to him I too had been meaning to bring it up, and I’m glad he did. I told him I’d always used protection with anyone else I’d been with, and he needn’t worry. I told him I trusted him, and after it happened in the middle of the night, I let my guard down about it in the morning. I told him I was going to get tested in the next few days so both of us could be certain he had nothing to worry about, and he told me he planned to go as well. He told me the last time he had been tested, and I told him mine. I had a strong feeling I had nothing to worry about with him, so scheduling a test felt more routine than anything. He’s a bit younger, so I’m sure he was worrying a bit more. I wanted to be sure to get results as soon as possible so I could give him peace of mind.
He was a good kid, and I really enjoyed being with him. I never wanted to do anything to hurt him. After we chatted over text, he told me he felt a lot better and wasn’t so worried. I apologized for putting him in that situation, and I told him we should discuss things after we both got our results back. I found it to be a very healthy conversation we probably should have had earlier, but I was happy we had it.
Southern Drawl
Posted by One Gay at a Time in Gay Dating on May 11, 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…
During my week off from work, I was laying in my bed on Grindr on my tablet. Much to my surprise, the southern guy from OKCupid I connected so well with over the phone popped up. Last I heard from him, he was seeing some guy. That was the reason he gave me for never following through to meet up with me. I wasn’t exactly thrilled with how it all went down. I left a really bad taste in my mouth. I really didn’t want to ever give him a chance, but I was constantly drawn to how well we hit it off when we talked on the phone.
I messaged him, “Well, look who it is!” He responded, and we began chatting a bit. He asked how I was and started getting a bit flirtatious. I told him I was well and pointed out his flirting would not work on me. He’d already turned me off by shooting me down. I detailed for him all the advances I made on him and pointed out how he never even took the time to meet me.
He pulled out the excuse that he wasn’t looking to meet someone else — It just happened. He kept trying to get pictures out of me. I told him I was not looking for sex, especially from him. I pointed out that if he wanted to grab a drink as friends, I would be down, but I wasn’t going to send him pix and do the whole Grindr flirting thing.
I’m not proud of this, but I had an internal conflict in my head. Part of me wanted to steal him away from the guy he was currently seeing. Another part of me wanted to make him fall for me and then dump him. I’m not that kind of vindictive guy, but I have to admit, the thought crossed my mind.
I decided then and there to form a game-plan. I was going to present myself as I am. I wasn’t going to try too hard or be someone I wasn’t, i.e. someone he wanted. I was just going to display my best self. If he happened to choose to go on a date with me, that was his choice, not mine. We exchanged pictures, none of which showed the goods. This is what really seemed to reel him in. He was certainly responding to visual stimuli. He really started getting chatty. I’d already learned he was still seeing someone, but he let it slip that it wasn’t the person he was going on the date with when he dropped me like a bad habit. I called him out for not calling me when things ended with the first guy. I put it all on him. I was running him through a guilt gauntlet. I made myself quite a prize for him to attain. Now, I had his attention. I wasn’t going to chase him. I set the bait, and he was going to chase me.
After more flirting and exchanging of pictures, we made plans to grab drinks after work Monday evening. We agreed upon Chelsea Manor, but when I arrived there, it was closed. He met me shortly thereafter, and we began to walk to find a bar to go to. I met him on the street with a very awkward handshake. He seemed very aloof. I had a feeling this was going to be an awful date!
We found a bar nearby, The Guilty Goose, and sat in the front window drinking a few rounds of beers. I quickly learned how homophobic he was. I’m a fan of guys who aren’t into the scene, but he was so far removed. It was alarming. He wouldn’t even walk through the “gay part” of Chelsea. I wasn’t asking him to go to a gay bar, but that was the neighborhood between his office and mine. There were plenty of places to go that weren’t gay bars.
We chatted over our beers and kinda hit it off once again. After three rounds, he asked if I was hungry, and we decided to grab dinner together. He knew of a good Thai place nearby, so we went there. We ordered a bottle of wine and our food. We didn’t need the bottle of wine. I could tell he was getting quite intoxicated. I was still pretty lucid, but I didn’t want to be drinking that much on a Monday night.
He started getting very flirtatious and sexual. At one point he removed his shoe and began massaging my crotch. I was wondering how the guy he was dating would feel about this. I wasn’t going to move things across the line, but if he did, I wasn’t going to stop him. Some other guy stole him away from me when I was trying to court him. It wouldn’t be my fault if he came to me while seeing someone else. I will say, I egged him on a little by unzipping my pants and offering a challenge to his dexterity. He wasn’t able to maneuver his foot into the opening. Then he tried using his hand, reaching far under the table. When I felt the waitress noticed the under the table horseplay, I got embarrassed and told him to put his shoe back on.
We paid our bill and made our way toward the PATH for me to go home. Apparently, he wasn’t done with me. “I’m really enjoying hanging out with you. Let’s grab another drink.” My goal for the first night was to set the bait, not to win him over. I was very cautious with him. He seemed like a wanderer. I didn’t want to take things too fast with him. He was going to have some decisions to make, and I didn’t want to force his hand with excitement. I wanted him to have the time to choose.
We plopped down at the bar at Jake’s Saloon and ordered a round. He placed his hand in my crotch and began groping me a little. I was getting drunk, so I upped the ante slightly. I put my hand down his pants and began groping him as well. He was making an attempt to do the same with me when I stopped him. He wasn’t very good at not being obvious. That’s when my mind began to develop a plan. I suggested we casually use the bathroom. I would go, and he would follow one minute behind. I wasn’t looking to have sex. I was simply thinking a little making out with some heavy petting.
I went into the bathroom stall, and he followed close behind. He began kissing me and unzipped my pants. He suggested “you show me yours, I’ll show you mine.” We both stood there with our manhood in our hands when he bent down and began licking the tip of mine. It was time to go. I did not want the bartender walking in on us. We put the boys away, zipped up and casually walked back to the bar.
We finished our beers and made our way for the door. I was saying goodbye to him outside the bar because we would be heading in separate directions. I brought up how he was seeing someone else, and I didn’t want to get involved with someone who was involved with someone else. Better judgment was kicking in. I was noticing how his wandering eye would be a problem. If he was willing to dump his current guy for a better model, who’s to say he wouldn’t do the same to me. I was proceeding very cautiously. He assured me things with the other guy were already on their way out. He’d had doubts before even meeting up with me. He wasn’t willing to really kiss me, and when I called him on it, his inhibitions dropped a bit. We kissed a lot. I told him he needs to shape up if he wanted to pursue anything with me. Outside all the sexual flirtations, we really did click. We shared a lot in common and the conversation was good. I wasn’t thrilled he was so southern, but I’m sure that would be something I could get over.
There was potential here, but like I said, I was proceeding with caution. He was far from perfect, but I did like him. This wasn’t simply a game of cat and mouse. This was the first time I truly played the game with purpose, but he was the end goal. Only time would tell if anything meaningful would blossom…
Follow @onegayatatimeLeavin’ On a Jetplane
Posted by One Gay at a Time in Gay Dating on May 11, 2012
Another Monday. Another day at work. My staycation was officially over. Another day periodically checking Grindr.
I spent my vacation getting myself back. The only problem was I only repaired the physical me, not the mental and emotional me. I wasn’t on Grindr all day long, but I would periodically check it to see if anyone had messaged me. I was simply a Grindr fish. No longer would I be a fisherman.
I had a dermatologist appointment in the middle of the day. While walking to my appointment, I fired up Grindr. I was curious to see if anyone was scoping me out. I was also in a new neighborhood. I was hoping to find something new and unexpected. In the short window it took me to walk about twenty blocks, I’d managed to strike up a conversation with three different guys. All seemed to be quite level-headed. I told them all I was looking for dates, and all of them seemed excited at the prospect. It was difficult trying to keep three conversations going at the same time. I told them I was walking into my appointment and asked each of them for their phone numbers. I managed to pick up a lawyer, an actor and someone who worked for a magazine rating cruise ships. I asked each of them for their pictures to add to my roster and went to see my doctor about lightening up a scar.
When my appointment was over, I thought I’d make my walk seem shorter by checking messages on Grindr once again. A guy near my office was on and started messaging me. He seemed pretty hot and well fit. He was staying at a hotel near me and was anxious to give head. I told myself not to even continue the conversation, but once again, I found myself thinking with the wrong head. I entertained the idea and asked him what he was proposing specifically. He told me he had to catch a flight in a short while, but wanted some fun before leaving New York. I immediately knew which hotel he was staying at and his occupation. “You’re a flight attendant staying at the Radisson, aren’t you?” I asked. “Yea. How did you know?” he replied. “Not the first one I’ve talked to at that hotel. You guys love that hotel, and you guys love Grindr. So what exactly are you looking for?” I texted.
He asked me to come to his room. He would leave the door ajar. I would walk in, he would tear off my pants and just begin orally pleasuring me. I wouldn’t have to touch him or do anything to him. He just really wanted to blow someone. I knew better, but I still bit anyway. I figured, “What’s the harm?” Work had no idea how long my appointment would last, and it was a slow day at the office. I decided to take a detour, but I basically had to run to his apartment. Thank God I have long legs to get me there. He was anxious because his checkout was very soon.
He was very worried about STDs and HIV. I assured him I was clean. I also asked if I would be allowed to play with his manhood if I chose to. He enthusiastically said yes.
I arrived at his hotel in time for an afternoon tryst. I hopped in the elevator and made my way to his room. I’d been here before. This wasn’t my first b.j. from a flight attendant at the Radisson. I really needed to stop making that a habit, but at the time, I was excited to get off in the middle of the afternoon. I arrived at his room, and the door was left ajar.
Warning: The following may be too graphic for some. I walked in and said hi. He immediately began lifting my shirt and sucking on my nipples. I lifted my shirt off, and he undid my pants. Just then, he turned to me and asked, “You’re really clean right?” I assured him I was. “You can never been too sure,” he added.
He began pleasuring me. After a few minutes, I made my way to the bed and laid back. I wanted to fully enjoy him. It wasn’t too long before he worked his magic, and I was able to conjure up exciting mental images. I shot in his mouth and all over his face and chest. He spit on my chest and began working on himself. Seconds later, he shot all over my leg. “Let me grab you a towel,” he said immediately. I wasn’t moving. I was quite anxious to get both of “us” off me.
I cleaned up and began to exchange small-talk with him. He was Austrian and was headed home that evening shortly after I would be departing his room. I needed to get back to the office, and he needed to finish getting ready for work. He told me how much he enjoyed himself, and with that, I made my way out the door.
Shamelessly, I had a smile from ear to ear. I was still high from the endorphins. It felt amazing. I was ashamed and proud in the same moment. I still knew I was broken inside and needed to stop having these trysts with strangers, but I was also enjoying my sexual liberation. Somewhere, there had to be a happy medium. It was up to me to find it…
Follow @onegayatatimeConnecting the Dots
Posted by One Gay at a Time in Gay Dating on May 10, 2012
Just because I said I wasn’t going to hit up Grindr constantly in search of sex from strangers didn’t mean I couldn’t satisfy myself with guys I’d already been with. This way they wouldn’t be strangers.
The last time I visited the bar manager in Hoboken, I had a great time. He had an amazing body, and we both really enjoyed each other. Wednesday, when I woke, he happened to be around. There had been a few days I suggested we get together, but he was always heading out-of-town for something. This time, he was available. There was a small snafu. He was sick. He had a sinus infection, so he was worried he’d get me sick. I told him it would be alright. We would simply avoid kissing each other. He told me to come up to his place, and he’d break out the glory hole again.
This visit was pretty much the same drill as my last visit to his apartment. He left the door unlocked. I was to walk in, undress, and saunter up to the hole in the sheet hung in the bathroom doorway. He was waiting for me on the other side. I hopped on my motorcycle and made my way to his place. I did as I was told.
Warning: The following may be too graphic for some. I removed my shorts and inserted myself into the opening. Immediately, he grabbed hold and began to orally pleasure me. It felt amazing. I wasn’t fully into the glory-hole thing, but it was making it a little more exciting. It wasn’t long before I pulled the curtain back once again. We started kissing each other all over each other’s bodies and swapping back to him on his knees. He was wearing his hat, which I’d already knocked on the floor so I could grab hold of his long flowing hair and his boots. It was an incredibly sexy look for him, and he knew it. I couldn’t keep my hands off his body.
He turned around and began grinding his backside against my crotch. I was incredibly turned on and excited. It felt so great to simply have his back pressed against my chest with one hand pulling across his chest so keep him close and the other pleasuring his impressive manhood. We continued this action until he was so excited he finished all over the bathroom floor. Everything felt amazing, and I was very close to finishing myself. However, this didn’t happen.
Once again, we moved things to the couch. He was all over me and everything felt incredible. I wanted to finish for him so badly. He was awaiting it with great anticipation ever since I first fooled around with him. We played for quite some time, and I kept losing my erection and gaining it again when I would pleasure his endowment. Throughout the whole visit, we were incredibly tempted to kiss, and came close many times, but at the last second withdrew again.
When a large period of time passed, he threw in the towel. He had to get on with his day. He was disappointed, and I was too. Not only disappointed, but also embarrassed. I wanted so much to please him. I wanted to give him exactly what he was looking for, but I came up short.
He walked into the bathroom and threw on a pair of sweatpants. As he walked, I could see his manhood swinging back-and-forth. It was such a turn-on. This is one thing that will always get my engines revving! He loved walking around with his package easily visible as well. It was something he was proud of, making it all the more sexy. I walked up to him and grabbed hold of it. I wish this was something I could do on the street. It would be so hot!
As I got dressed, I made a point to look around a bit. When I last left his place, I suspected he lived with his partner. I indeed confirmed my suspicion when I noticed there was only one bedroom. I also tried to casually scope out the pictures on the wall. The apartment was not decorated like two random roommates living together. It was definitely the residence of a loving couple. I felt a pang of guilt. This guy seemed like a good guy. I was disappointed in him for cheating on his lover. I didn’t know the dynamic between the two, but I never liked seeing infidelity. I wasn’t passing judgment, but I was putting myself in his mate’s shoes. I was a partnered man’s affair. Now I knew why we never had full penetration.
I said goodbye and made my way home. This would be the last time I would see him. I wouldn’t be the last time I chatted with him. He happened to sign on to Grindr about a week later. I was checking to see if I received any new messages and messaged him just to say hi. He was in Miami. I asked him if his man came with him, and he told me he was at home. Without knowing it, he slipped up and confirmed to me he had a man in his life. I pointed out to him how I caught him in a slip-up. When he originally mentioned the guy, he told me it was his roommate. He acknowledged his lie, and I told him we were cool. I had no hard feelings. It was his life, not mine. I then realized he was probably on Grindr down in Miami looking for a new piece of tail. I told him to enjoy himself, and with that, I said goodbye to him for probably the last time.
Follow @onegayatatimeSpring Fling
Posted by One Gay at a Time in Gay Dating on May 8, 2012
SPRING! The first day of Spring finally arrived. We didn’t have a very rough winter, but I was certainly ready for spring. I had no work obligation, so I rang in the new season from the comfort of my bed watching TV.
About 1:00 am, I got a booty call. There was a guy I had been in touch with for over a year and never met. He was a very sexy Hispanic man who it seems swam in the same circle as me. This wasn’t just any random booty call, however. He was over at a friend’s place, and they were looking to have some fun.
They didn’t want to have a threesome in the sense I’d recently been in. They were more looking to watch porn and jerk together with some light fun. Things got particularly uncomfortable when he asked if I party. I am NOT into drugs mixed with sex. It’s not my thing. I was pretty clear about this. I don’t feel comfortable around it at all. I told them if partying was in, I was out. They were fine with that. They didn’t think I was coming, but in the end I agreed to come by.
I quietly snuck out of my apartment and hopped on the motorcycle. I made my way in the chill of the night over to Jersey City where his friend lived. When I got there, I couldn’t figure out where to enter the building. I finally found it when the Hispanic guy came down to meet me. I finally got to meet him in person. He was hot and was an impressive presence. He was well-built and very tall. I shook his hand and rode the elevator up with him.
When we entered the apartment, I was greeted by a gorgeous dog. It was the Hispanic guy’s dog, and he put him in the bedroom so he wouldn’t be a bother. It was a gorgeous apartment. The owner was sprawled on the couch in front of the porn playing on the big screen TV. I was introduced and removed my jacket. I was encouraged to make myself comfortable. All three of us began to strip. I wasn’t attracted to the owner of the apartment at all. He wasn’t attractive, and he had a very distant look in his eyes. He kinda creeped me out. I had my suspicions he had already partied. He had a beer in his hand, but I had a feeling that wasn’t the culprit.
Warning: The following may be too graphic for some. The three of us laid on the couch watching porn together exciting ourselves. Then the kissing began. I started kissing the hot one while the ugly one started kissing all over my body and began orally pleasuring me. He was constantly going deeper to the point of making himself violently gag. I was petrified he was going to vomit in my lap. I tried to concentrate on the hot one. He was very normal and enjoying himself.
The ugly guy was almost like a dog on me. He kept climbing on me, and I really wanted him to go away. The Hispanic guy kept making comments about him and to him. He, however, wasn’t speaking at all, only grunting. “She’s a big old bottom,” the Hispanic said. I fully understood that by him nudging his hairy a$$ toward me constantly, but I was not interested. He wanted me to penetrate him, but I was not going anywhere near that, even with a condom on. I was cordial to him, but I never purposely engaged him in any way. He kept getting in the way of me enjoying time with the hot one, whimpering by my face waiting to suck on my mouth.
A few times I contemplated leaving. I never did anything I wasn’t comfortable with, but I wasn’t really enjoying myself. Periodically, the porn would freeze to buffer, and the “dog” would have to fix it. It was a nice reprieve from him being all over me.
After some time, the hot one decided it was time for him to head home. He needed to get the real dog back and settle in for the night. If he wasn’t staying, neither was I. I stood and told them I was heading out as well. I started to get dressed. The ugly dog on the couch was confused by all this and still in a haze. The Hispanic guy asked if the other guy could give him a ride home. After some confusion, he agreed. I was very happy I wasn’t in that car. I wasn’t sure he’d be ok to drive. I waited for the other two to finish getting ready and dressed to head out.
The Hispanic with the dog told us he needed to go downstairs to let the dog relieve itself. I wasn’t thrilled with the idea of being left in the apartment with just him. I stood by the door, and the other guy got ready quickly. We ended up all riding down in the elevator together. When we got downstairs, we all said goodbye. I hopped back on the motorcycle, sped home and hopped in the shower.
When I got back to my apartment, I got a text from the Hispanic guy. “Sorry. I think my friend was into you. I felt kinda out-of-place. LOL.” I responded back after I got out of the shower, “Hey dude. Great body. Seem fun. No offense, but your friend isn’t really my speed. Sorry. Not sure if you had fun with me, but feel free to hit me up sometime.” That’s when I got the full story between the two of them: “Him and I hooked up when we first met and no more after that. Sorry if I came off rude. I had fun with you. Definitely. But, he was trying to have you for himself. I got the hint. He’s my bud, so I was trying not to f*ck it up. I wasn’t sure if you were into him or not. You were kissing each other. Plus I had my pup with me.” I explained to him the confusion: “I was more just letting him play. Didn’t want anyone to feel left out. LOL. I was trying to get more of you ;)” He told me, “I would chill again whenever.” I quickly responded, “Cool dude. You have my number. Anytime. Trying to go on a Grindr diet… Obviously failed tonight.” He finally added, “It’s cool. Had fun. Finish some other time. ;)” With that, I hopped into bed.
I finished myself off and passed out. I didn’t set an alarm since I had nothing to wake up for early in the morning. This post should have been titled I have no willpower. Hopefully the next day I would be able to stick to my new diet.
Follow @onegayatatimeLetting Him Down Easy
Posted by One Gay at a Time in Gay Dating on May 7, 2012
Monday, I decided to be a good brother and pick my sister up from the airport. I drove her to Newark Airport early Friday morning before all of my Grindring, and she was arriving around 2:00.
Before I hopped in the car, I made plans with M.E. to meet up later that day. I wasn’t planning to tell him I knew about his Grindring from my bedroom. I was just going to keep that in mind when interacting with him. I wasn’t going to let myself fall for a guy like that. For us, it would be purely fun. He told me he had class that afternoon, but he would come meet me on the pier when he finished.
I was regretting agreeing to pick my sister up since it landed smack in the middle of my day. I wanted to head out to the pier and get some color while I was off from work. The forecast was looking gorgeous for the week, and I planned to take full advantage. I decided not to waste the morning and went for a run around 1:00. I came back to my apartment, showered and packed a bag for the pier. I hopped in the car and headed to the airport. My sister was delayed, so I spent about a half hour circling the grounds. When she finally touched down, I parked in front of her terminal and began reading my first Out magazine. I was becoming a full-on gay man. I finally subscribed to a clearly homosexual publication.
She came out, and I drove her back to Hoboken. We swung by the pier to drop be me off so I could get some sun, and she went home.
Around 3:30, M.E. joined me on the pier. We laid next to each other talking for a bit. I gently stroked his hand with mine. We weren’t being blatant or obvious, but we still found ways to show affection. It was a nice time. Around 4:30, the sun was beginning to set. The temperature was dropping, so I suggested we head back to my apartment. I wasn’t even thinking about this in terms of sex. I was just cold.
He gave me a ride back to my place and decided to come up for a bit. He couldn’t stay too long because he had plans for the evening. We ended up in my bedroom fooling around a bit. It was nice to have him in my bed again. Every time we were together, I enjoyed myself.
The time came for him to leave, and I said goodbye to him at the door with a kiss.
Over the next week, I didn’t really reach out to M.E., and he didn’t really hit me up either. When enough time had gone by, I assumed he met someone else. I was trying to get away from the relationships based on sex, so I wasn’t exactly protesting or questioning why his calls stopped.
One day I got a text from him asking me why we hadn’t been in touch in some time. I told him I assumed he met someone else. He assured me this wasn’t the case. He told me the reason he was so quiet was because he was trying to create distance. He was beginning to fall for me and didn’t want to get hurt. This is when I pointed out to him I knew he was on Grindr when he was at my apartment. I didn’t tell him how I knew this information. At first, he denied it and told me he was chatting with his friends about his spring break trip postponement. I acknowledged that, but also pointed out he was on Grindr while he was in my apartment. I told him how insulting that was to me. I pointed out how, by no means, were we exclusive, but to be on the app while sitting with me was not something I looked kindly upon. He apologized profusely. I told him I noticed he blocked me on Grindr as well. He told me the reason for this was because he saw me on there periodically, and it was killing him. He was imagining me with other guys, and it was getting to him so much he blocked me so he wouldn’t have to see it anymore. I told him I wasn’t holding anything against him, but it was shaping how I looked at whatever was going on between us.
He was completely torn up about it. I had a lot of other things going on in my life at the time, and I didn’t really feel like getting into it with him. I was partially using this as a way to make a clean break from him. I liked him and cared about him more than a one-night-stand. I considered him a friend who I also happened to enjoy in my bed. He was more friend than benefit. I didn’t want to hurt, but I also needed separation. There was too much going on in my life at the time. He begged me to talk on the phone, but I told him that would have to wait. I lied and told him I was with friends and didn’t want to be rude by taking a phone call.
I knew he wasn’t happy, and it wasn’t what he wanted. I needed to think about me for a change. I needed to put more effort into the men I was meeting and looking toward a long-term relationship with, rather than the men I just enjoyed having around for sex and a little companionship. It wasn’t fair to him, and it wasn’t what I needed. The time came to move on. How that would shape my relationship with M.E. was yet to be determined…
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Posted by One Gay at a Time in Gay Dating on May 4, 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…
Saturday had arrived, and it was St. Patty’s Day. I was out early in the morning to hit up the gym. I wasn’t going to find myself wasting another day lying around my apartment looking for sex. It was the true start to my staycation and to the new me. It was gorgeous outside, and I was motivated.
As I left the gym, I ran into K and one of my other friends. They were heading into the city to drink, but I wasn’t interested. I’d just come from the gym. I’m not a fan of day drinking to begin with. I said goodbye and continued on my way home. D’s girlfriend was up from Philly that weekend, so I texted them to see what they were up to. They were grabbing brunch and had no plans for the rest of the day. I told them I was bored and lonely, and if they thought of anything, I’d be game. I also called my old roommate to see what he was up to. He was studying for yet another test he had to take for work. I knew it was useless to try to convince him to do anything else.
Finally, D and his girlfriend decided to swing by. They came up, and we just lounged around chatting. She’d never been to my apartment before, so I showed her around. After some time, we decided to go for a drive and check some new cars for D to possibly lease. I was game, so we made our way uptown in the great weather to D’s car.
We decided to drive around Jersey City since there were a few nice neighborhoods I’d never explored. I was a bit curious, and the other two were as well. I also wanted to scope out a spot I had in mind for dinner that night with the guy I spoke to on the phone for two hours, Travel Agent. We drove by the cute cafe on the corner in an upscale neighborhood of Jersey City, The Hamilton Inn. I’d seen it a few times before and had been curious how it was. I pulled up the menu on my phone and suggested the idea to T.A.
He was still working, but he said it sounded like a good idea. We planned to work out the rest of the logistics later.
We drove around for quite a bit more before finally returning to Hoboken. They dropped me off at home. I hopped in the shower and began to get ready for the evening with T.A. I’d been texting him a bit and made a reservation at the restaurant for 7:00. When he told me it’d have to be later, I called and changed the reservation for 8:30. When the time came, he picked me up in his nice Audi. He was a good-looking guy. He wasn’t someone you’d stop on the street and say, “Damn!” but he was good-looking. We jumped right into conversation. It was fairly relaxed. I feel he may have been slightly uptight, but I tried to remain candid and relaxed.
The Hamilton was exactly what I was hoping for. It had a decent crowd, the food looked and smelled amazing, and we got a nice table to sit and chat with each other. The obvious and easy thing to decide was to order a bottle of Malbec to share. I still couldn’t help feeling he was uneasy about things. He just didn’t seem to relax. I tried to lighten things up and asked if he wanted to split an appetizer. He agreed, but it wasn’t terribly easy to pick something. He defaulted to me, and after discussing it, I finally decided on the pierogies with goat cheese appetizer.
We began by talking about where we grew up in more detail than we discussed on the phone. The conversation shifted to our jobs. I got to learn in greater detail what he does. I told him about my job, and slowly I began to realize I was monopolizing the conversation. He’d ask me a question, and I’d answer in detail. When I’d ask him questions, his answers would be short. I wanted to get to know him. He seemed like a decent guy.
The waiter returned and we ordered. I was debating between he risotto and chicken. I decided on the chicken, and he decided on the risotto.
We talked some more until our food arrived. Or should I say, I talked some more. I would never say it was a bad date, but I would also not say it was a great one either. We shared some of our meals with the other. It was a nice time. I was enjoying his company, and the food was delicious. I was looking forward to a second date so we could think of something more relaxed to do. Hopefully that would break him out of his shell.
We declined dessert since he had to get home because he had a big work project the following day. He expressed to me how much he enjoyed the date. I was happy to hear it. We split the tab and made our way back to his car. On the way back to my apartment, we passed another restaurant I was interested in trying. I mentioned it to him, and he said, “Maybe next time we should try there.” That was a very hopeful statement. If he was already thinking about next time, maybe he really did enjoy it too.
We stopped in front of my apartment, and he put the car in park. He leaned over and gave me a kiss. I pulled back and went in for a second. It was nice, and I wanted him to know I was interested. I told him, “Call me when you’re back from Mexico. Or, you can text/call whenever you like,” with a smile as I exited the car. He told me we’d be in touch.
After that, I heard nothing from him. He clearly stated his enjoyment and mentioned a second date. How was I not supposed to think he was interested? I sent him a text to tell him of my good time with him, but I got no response. I checked Grindr, and sure enough, he was online. Clearly he was ignoring me. I messaged him on Grindr as well. When a day passed and I heard nothing back, I decided he would either deny this or the “relationship” would be dead before it began. “I hope you’re not ignoring me. I thought you were a classier guy than that.” He had given me two different phone numbers, so I asked if I was texting the wrong number. Finally, he responds explaining he was busy and apologized. He told me he was interested in seeing me again as well.
However, after that, I didn’t hear from him again. I know when I’m not particularly interested in a guy, I don’t outright tell him that. However, I don’t talk to him about future dates to lead him on. It was very disappointing, but I wasn’t going to let one guy get me down. My Grindr diet was slowly working. I was back to concentrating on dates and not sex. Hopefully, with enough time, I’d find a good guy to settle down with — Someone to be the reason I delete Grindr forever…
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 