Posts Tagged heavy petting
Never-Ending Date
Posted by One Gay at a Time in Gay Dating on May 29, 2012
I’d begun an amazing date with a spectacular man, and I couldn’t wait for what was to come next. Although I had been to Frankies 570 multiple times before with multiple dates, this time was special. I had an amazing guy to share a meal with. Ironically, my meal from days prior was so good, I ordered the same the again.
Conversation over dinner we great. It flowed like water downhill. We were both very flirtatious and chatty. On many of my other dates, there were long awkward pauses, but not on this one. Everything was just so easy. When I excuse myself to go to the bathroom, he leaned in requesting a kiss first. It was incredibly sweet and adorable. I really liked this guy. He was everything I was looking for.
I was just taking extra care to make sure I didn’t get ahead of myself. I had a history of falling for guys who would hurt me or not be interested in pursuing anything further. While in the restroom, I looked in the mirror to keep myself centered. All I could do was smile at my reflection like a giddy schoolgirl.
When I returned to the table, the conversation picked back up where we left off. My hand was on his leg under the table. His body language was very positive.
Our meals came, and we shared them with each other. Both of us were very happy with our selections. When the meal ended, we agreed to order a dessert to share. We got the crème-brulee. I dug my spoon into it and fed him a spoonful. It felt incredibly romantic. He smiled as his mouth closed around the spoon. We finished dessert and began to chat about what to do next. He was dancing around what I can only assume were his true motives. He said, “We can go have more drinks.” I interjected, “I don’t want to drink anymore.” “We can drop our bags at my place and go out. We could grab Pinkberry…” he added. I cut him off at the pass saying, “You can stop dancing around it. We can go back to your place.” He immediately smiled and agreed that was the best idea.
I wasn’t thinking we were going back to his place for sex. I knew there would be making out and a lot of heavy petting, but I wasn’t planning to give it up that easily. We hopped in a cab back to his apartment. He asked if I wanted to go to the roof, and I told him I would default to him. We were on his home turf. He could run the show. I picked the bar and restaurant. It was his turn to drive. Before we got to his place, he warned me of the condition of it. He informed me he lived like a frat boy.
When we got to his place, we stopped in his apartment on our way to the roof. I didn’t think he was as bad as he let on. We began making out on the bed. This, of course, led to many other things. Slowly but surely, clothes started landing on the floor in scattered piles. Eventually, we fond ourselves naked and engaging in a myriad of sexual acts, but penetration would never occur.
He was a very passionate man. I have found it nearly impossible to find a man whose intellect, wit and sense of adventure outside the bedroom matched their passion in the bedroom. He was a diamond in the rough. I wasn’t going to let this one go without a fight.
I noticed he was very into music. It was like he needed a soundtrack. I liked it. Every minute I was learning something new about him, and it was all making me like him even more.
We never made it to the roof. We ended up passing out on top of each other’s naked body. In the middle of the night, we both woke up. It was around 2:00. He offered for me to stay. I was under the impression that was already happening. I assumed I would just stay the night. We cuddled some more, and he turned out the lights.
When we woke in the morning, things weren’t awkward at all. I felt very comfortable with him. We talked about how we didn’t have sex and how that made us both happy. We didn’t need to rush things. I mean, I was spending the night on a first date, but I was happy true sex didn’t occur. I was also thrilled he was the type of guy who would just bring that up and not keep it inside for fear of saying the wrong thing. He spoke his mind. I needed to get back to that. Being with him might help me get back to that.
He was amazing. There was no question about it. We were both starving and decided to get dressed to hunt for some breakfast. We stopped by a few places before finally settling on Jimmy’s American Grill and Bar. We grabbed a table outside and picked up the conversation where we left off the previous night.
I let my freak flag fly. I felt so free with him. I told him all about me and my idiosyncrasies. I explained my Christmas Bash and all the work I put into it. He referred to me as Martha Stewart, and I expressed my hatred for that referral. I didn’t like that my cooking and entertaining had a feminine connotation. I told him I was more the Nate Berkus type. He laughed and agreed it was a better reference. I told him about my crazy coworkers and how we would make an amazing reality show. I told him about growing up on a farm. Everything I could think of, I brought out. He loved it all! I learned about where he grew up and his career in advertising. Every word made me like him more and more. He also told me about his friends. They texted him while we were eating to ask him to come to brunch 2.0.
Somehow, we got on the topic of The Hunger Games. I was reading the books, and he had already seen the movie. I told him I was looking forward to seeing the movie. He told me he would go see it again and asked if we could go see it Sunday. You could have knocked me over with a feather. He was already planning date number two before date number one concluded. I was thrilled and immediately accepted.
He walked me to the PATH to say goodbye before heading downtown to meet his friends at Elmo. We kissed each other goodbye and gave a long lasting hug. There was a homeless man panhandling next to us who said, “Get a room,” through a smile. He began laughing, and I started to crack up since I was the one facing him. I said to my amazing date, “That made my day.” Immediately, he replied, “You made my day.” I was in heaven. I said goodbye and went down the stairs to the train.
Later, I learned from checking his Twitter that when he checked in at dinner on Foursquare, he wrote, “Easy conversation + tasty food + hot boy = great date on a Fri night (@ Frankies 570 w/ 2 others)” and the next day at brunch, “When last night’s date becomes this afternoon’s brunch date (@ Jimmy’s American Grill & Bar). He really did like me. I was just finding it hard to take. It was like a dream. I couldn’t really believe it. I didn’t want to get too excited because I didn’t want to get hurt. But, honestly, who gives a f*ck. I was happy, and that was all I cared about.
Meeting the Hatfields
Posted by One Gay at a Time in Gay Dating on May 18, 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…
Southern Drawl was very anxious to see me. Before our last date ended, he asked me, “So, when do you get to see me again?” It was a bit egotistical, but it was also a little cute.
I had plans with other guys for the rest of the week with the exception of my volleyball game on Thursday. We agreed to do happy hour after work on Friday to get the weekend started off right. He was going to the Frying Pan, a permanently parked barge on the Hudson River that doubles as a restaurant/outdoor bar, with a group of his coworkers. Apparently, he was comfortable enough to introduce me to them.
He was already there when I made my way across town to meet him. He worked right across the street, so there was a solid crowd present from work. I found them in the crowd and pulled up a chair to the table. Everyone was very welcoming and nice. They immediately offered me a cup of sangria, and I settled in. I joined the big conversation, and Southern Drawl and I had a few side conversations not meant for the table.
I wasn’t sure to what extent he was out to his coworkers, so I played a vague roll. I didn’t show any signs of affection or do anything that would be a severe tell. I had a good time.
When everyone was ready to go, we started walking. We were heading to his apartment, but we walked with the others until they peeled off to head in separate directions. It was then I was informed that this was a big deal. None of the other guys he dated had met his coworkers. Only one or two of them knew he was gay, so this was somewhat of a public coming out. I’m sure his coworkers would put two and two together if he was inviting a man to join them for drinks. It was flattering he was willing to do that with me.
Since before I met S.D. in person, I’d learned of his incredibly flamboyant and promiscuous roommate. We talked about him to quite an extent on the walk.
I could not have been prepared for his apartment when I walked in there. It was an utter dump! His roommate was lounging on the couch when we arrived. S.D. needed to change before we went out for the rest of the evening. I chatted a bit with his roommate, and he certainly had a strong unwarranted air of superiority. We didn’t get along, but we didn’t clash either. He was a non-entity to me.
Meanwhile, I made a comment about S.D.’s shoes, and I was ripped a new one. He went off on me how expensive they were and how dare I downplay them. I was dying to get out of that apartment, and S.D. was dragging his feet.
He told me his friends from back home in the south were going to be out on the Lower East Side since one of them worked at Brother Jimmy’s. We decided to pick a place in the neighborhood to grab dinner before drinking our faces off. We found a nice Italian restaurant, Pete’s Tavern and shared a delicious pleasant meal. Things were starting to feel comfortable with him. All the awkwardness melted away. We had great conversation and kept each other on our toes. The conversation was great, but I began to wonder if I was sexually attracted to him. When he sent pictures to me, I found him to be quite attractive, but since being with him, I didn’t get excited or aroused by him. We hadn’t crossed that bridge yet, but I wondered if when I came to that bridge, would I even want to cross it. On top of that, we hadn’t discussed positions since we first spoke on the phone. He told me he didn’t have much experience in the bedroom originally. He said he never really bottomed, but he may be willing to experience it. Since then, I got a different picture learning about the long-term relationships he’d been in. I wondered if they were sexless, or was he lying. We were two tops, and that was going to pose a problem as some point.
After we finished dinner, we walked to Brother Jimmy’s to meet his friends. He was excited to introduce me to them. They’d already seen pictures of me and predicted I was a far better man for him to date than the one he just let go. They already loved me before even meeting them, so it was my game to lose.
S.D. introduced me to them, and we hit it off pretty swimmingly. His best friend, a female, pulled me aside to talk and gossip. We chatted, and she expressed how much she liked me. “You’re just the right amount of gay,” I was told. I’d always thought that about myself, but it was still interesting hearing someone say this to me. Even the friend, the girl who was working behind the bar planted a kiss on me, right on the lips. It was a pleasant surprise. I was a hit!
S.D. also told me his friend from work, “his little buddy,” was joining us. This kid was gay and even lived with S.D. on the couch for a period. They were very close and best friends of sorts. When this kid arrived, I was introduced to him. He seemed very nice, and we exchanged small talk. Almost immediately, S.D. and he separated from the group and began chatting the night away. It was obvious to me S.D. had a crush on him. I wondered if the little guy just wasn’t interested in S.D. and that was the hangup for why they weren’t together. I felt incredibly neglected. I was getting quite drunk, and that usually peaks my emotional state. I was very close to walking out the door and going home without a word but better judgment kicked in.
After we watched someone who looked like Snookie do an amazing rendition of Adele for karaoke, I was ready to go home. I was drunk, and I was trying to see past how he ignored me. Even after all I drank, the bartender charged me seven dollars. I’m still not 100% sure why, but I asked S.D. if he wanted to come back to my place and spend the night. I think I wanted to test our sexual chemistry. I wasn’t looking for sex. Clearly that wasn’t possible in the state I was in. I just wanted to get somewhat physical with him.
We made out way back to my place and quietly made our way to my room. We climbed into bed to spoon, and I passed out quickly.
Warning: The following may be too graphic for some. When we woke up in the morning, we started spooning and fooling around. There was a lot of heavy petting and oral pleasuring. It wasn’t long before he was straddling my chest fondling himself. It also wasn’t long before he excited himself so much he finished right on my chest. He asked for my permission, but I wasn’t expecting it to happen almost immediately.
We lounged in bed for some time before I made us breakfast. There was a bit of a schedule for the morning, however. My parents were coming into town for Easter weekend. I needed to get him out of there before they arrived. Just as we finished eating, I got a call from my parents. They were downstairs. I told S.D. to quickly get dressed and make his way down the back stairwell. He was fine with this, and we agreed we’d chat later on the phone. I hustled him out the door and kissed him goodbye.
One minute later, I threw on flip-flops and went down to greet my parents. They didn’t make a single comment about the guy leaving my building. I had yet another celibate weekend in front of me, and this was a good thing.
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 @onegayatatimeSticking to the Plan
Posted by One Gay at a Time in Gay Dating on May 4, 2012
I had a Friday to myself, and I wasted it on hookups. I could have been doing something productive like going to the gym or grocery shopping, but instead, I spent the day inside trying to line up sex.
There was one man in particular who I’d exchanged messages with on adam4adam.com. He was a well-built guy with a sexy body. He had a nice amount of body hair, great muscles and a spectacular behind. We’d talked about hooking up a few times, but we’d never seemed to line our schedules up. I messaged him, but he didn’t respond.
I continued to search for other guys on the computer when he finally responded. He didn’t read my message until it was too late. We exchanged phone numbers, and he called and told me he had a lot of errands to run before his mother’s birthday the following day. He wasn’t able to see me until later, but suggested we Skype in the meantime. I had nothing to do, so I agreed.
He was even good-looking with bed head on the computer. I couldn’t imagine how sexy he was in person. Seeing him on the computer was just making me hornier, if that’s even possible. I tried so hard to convince him to come by before his errands and do them later. All he needed to do was time-shift his day. He kept telling me the only way it would work is if I came to his apartment. I couldn’t because it was raining, and I don’t ride the motorcycle in the rain. We pushed back and forth for some time to no avail. Of course there was some teasing with body parts on camera while all this was going on. I couldn’t wait to feel his sexy body. Alas, he had to go, so I said goodbye and we made tentative plans for later. I told him when I came by, he’d certainly have to wear his jockstrap for me. He gave me a disclaimer. He was up for almost anything, but he was not up for full penetration the first time meeting me. I was a little disappointed, but understandable.
That’s when I turned to the Mexican guy in the previous post. He was willing to come by right then, and I needed a release. I had immediate regret after that encounter.
Later in the day, my old roommate texted and asked if I was interested in meeting up for happy hour. After being cooped up in my apartment all day, I thought that sounded like a spectacular idea. No one ever invites me out for drinks either. It’s usually me doing the inviting, so it was a special treat. I texted the burly man from my morning Skype session to tell him I’d have to postpone. He called immediately protesting. I told him other things came up, and I wouldn’t be able to come by. He didn’t stop persisting to try to persuade me otherwise. I told him he could have solved the whole thing had he come by earlier in the day.
The clock reached 6:00, and I hadn’t heard from my old roommate. I reached out to burly man to see if he was still available. Indeed he was. I agreed to come to his place a few miles from my apartment. He told me he would be waiting for me in bed wearing nothing but a jock and would leave the door unlocked for me to just walk in.
I drove over there and texted him when I got to his neighborhood. I tried the door, but it was locked. I called him to tell him, and he said his upstairs renter must have left and locked the door behind him. He told me to back away so he could unlock the door. I did as I was told and gave him a minute to get back to his bed.
Warning: The following may be too graphic for some. I came in, undressed down to my boxer briefs and began kissing his back while pressing my body against his. It was as great as I imagined. His a$$ looked incredible in that jockstrap! I could barely resist him. We had a lot of fun together. There was a lot of groping, heavy petting, kissing, sucking, licking, biting, rubbing, etc. It was great. I was really enjoying the jockstrap as well. I was grinding on his backside, almost penetrating him, but never fully entering him. He really enjoyed it and was pushing me further, but in the end, he stopped himself.
He was begging for me to finish, and he brought me to the edge many times. He started orally pleasuring me. He thoroughly enjoyed this, and it was turning me on since he was enjoying it so much. Eventually, I finished in his mouth and all over my abdomen, and he loved it. He began to use his hand to pleasure himself. I helped by applying pressure to different areas until he finished all over his abdomen. We’d chatted about how each of us shoots on Skype, and it was interesting how different and how similar we were. His description was pretty spot on for what actually happened.
We both just laid there a minute and enjoyed the feeling pulsing through our bodies. I still couldn’t get over how amazing his a$$ was. I wanted to penetrate him so bad, but I knew that would have to wait for another day. He hopped out of bed and handed me a towel to clean up. While I stood there, I met two of his cats. They were very cool. This guy was quite into animals. He had a huge saltwater fish tank as well. He ran to the restroom while I got dressed. I also took the opportunity to snap two pictures. He came back and got dressed as well.
He walked me outside and chatted a bit while he smoked a cigarette. He didn’t live in the best of neighborhoods. An old woman so strung out on something walked by, and he engaged her in conversation for quite some time before finally offering her one of his cigarettes and sending her on her way. He told me about how his mother lived next door and his family’s ties with the city. He was a really nice guy. I could see myself seeing this guy again some time. He told me he was also kinda seeing some guy, but it was very casual and nothing serious. He mentioned the desire to see me again sometime, but we didn’t set up anything concrete.
I sped off on the motorcycle back home to shower and get ready to go out and meet up with friends. The only friend interested in going out was P. We agreed to hit up one of my favorite local spots where I know the owner, and he takes good care of me, Cooper’s Union in Hoboken. We had a relaxing night drinking and sitting at the bar. I told her about how I was getting out of control, and it was then I decided I was going on a Grindr diet. This had gone on far too long. I was realistic enough to know I couldn’t quit it cold turkey, but I also knew it was a great temptation for me. I was going to try to steer clear. I would only go on to see if someone messaged me. I would no longer cast out a net and would no longer have it running on my phone all day. I needed a break. I was addicted, and it was time for me to ween myself off the drug…
Follow @onegayatatimeChelsea Early
Posted by One Gay at a Time in Gay Dating on April 26, 2012
Saturday morning I woke up at a decent hour. It wasn’t easy sleeping with Chelsea. He thrashed constantly.
We quietly chatted for a few minutes lying face-to-face before I told him to go back to sleep while I made breakfast. I whipped up some of my famous homemade pork and apple sausage, scrambled eggs and sliced up an avocado. I brewed him coffee and went back into my room to rouse him. I slowly slid into bed and nuzzled with him to gently wake him. He was really cute, and I enjoyed doting on him a little.
When I finally woke him, we embraced and flirted a bit. I was feeling a bit randy and naughty, and I was trying to get a little frisky with him — Nothing serious… just a little heavy petting. He was quietly protesting, but he was enjoying it. When I finally managed to sneak his briefs down to his knees, he gave in. It was better than I expected. We had a little fun, but again, nothing serious — Just a lot of groping. I didn’t want to make him uncomfortable. After a bit, I made my way to the kitchen, and he joined me. He was very grateful for the breakfast spread and raved about how good it was.
After we finished eating, we moved to the couch to relax in front of the TV. My female roommate woke up and came into the living room. I introduced her to Chelsea, and they hit it off immediately. We had our laptops out, and we were playing on Facebook. My roommate was telling him all about her dating life, and Chelsea was trying to think of guys he could set her up with. I became a non-participant observer at this point while the two of them had girl talk. She apologized for monopolizing our time, but I didn’t really mind. It was nice to see him interacting with her. I always put prospective men through a litmus test. They must meet my friends and get along with them before I will fully accept them.
The time came for him to head back into the city. He needed to do a bunch of things before he started his new position in Connecticut. He was also looking to find a sublet for his apartment while he was traveling for work Monday through Thursday. I told him I’d talk to my friends about renting it out, but I wasn’t thrilled he was about to start a job that would have him traveling far away. This would most likely mean I wouldn’t see very much of him. He would only be around on the weekends. If I went away for the weekend, I wouldn’t see him for a long time. It was a tough obstacle I could see in the near future.
When he got back to the city, he texted me about his conversation with his friend. He was talking about where he was the previous night, and the friend asked him how we met. He was embarrassed we met on Grindr and lied. I texted him back telling him he need not lie in the future. He should simply tell people we met through a mutual friend. He also realized he forgot his toothbrush. We made plans to go out again on Tuesday, and I told him I could either bring it to him, or he could leave it at my apartment until the next time he spent the night. I was being slightly presumptuous, but he decided to leave it at my place.
That night, I went to one of my best friend (and avid blog reader), J’s surprise birthday parties hosted by his fiancée (another avid blog reader). It was still March and still cold outside, but there was no way I was taking the train out to where he lived. Every time I took the train there, I ended up sitting at the train station for roughly and hour or so, and then spent over an hour on the moving train. He lived a 40 minute drive away, so I decided if I bundled up, I could brave the cold and ride the motorcycle out there. Boy was I way off.
I froze my a$$ off. I was incredibly cold the entire ride. I couldn’t wait for it to be over, but my friend, J is well worth it. I also got to hang out with one of my other college teammates who just moved back from California. I hadn’t seen him since I went out there for a trip with friends and met up with him for an afternoon.
J was so surprised to see both myself and our other teammate. He didn’t even know he came back from CA. I was thrilled to see him so happy and glad I made it out there to witness it. When everyone was packing up to head home or off to the bowling alley for some more fun, I decided to split. It was already nearly midnight, and it was only getting colder. I said goodbye and sped off for home trying to avoid hypothermia in the process.
When I got home, my roommate and I chatted about how much she loved Chelsea. She thought he was a good fit for me and thought he was a really great guy. It was nice to hear her glowing review. I had nothing but positive reviews as well, but only time would tell if this was meant for the long haul.
Follow @onegayatatimeStood Up Twice But Third Time’s a Charm
Posted by One Gay at a Time in Gay Dating on April 13, 2012
So much for getting things out of my system while in California. I was supposed to find myself while I was out there. I was supposed to calm down with the hookups. If anything, it had a converse reaction. Maybe it jump-started my libido. Since I arrived home, I had one meaningless one-night stand/hookup, and hooked up with a guy I could possibly considering seeing again. What was I, in college?
Wednesday at work, I was back to my old habits. I was all over Grindr searching for guys to go on dates with. The problem was none of them were looking for dates, so I decided to fill the time between dates with more hookups.
I hit up one of the guys in my favorite list, but he was really just interested in sex. We tried to make plans to meet up, but were having a hard time finding a location. He proposed an adult video store booth, but as you can imagine, I wasn’t onboard. He also wanted to go bareback, but I’d learned my lesson with that. No more taking those kinds of chances. When I tried to make more realistic plans, he flaked.
I started talking to one guy who was really hot. He wanted to hookup badly, but he needed time. He needed to prepare, which I can heavily respect, but he was also visiting. He needed to go out and get supplies to perform said preparation and needed to find poppers. It was pushing 6:00, and I wasn’t going to hang around the city any longer. He ended bailing on me, so I made my way home alone.
Two guys flaked on me; however, talking to them got me riled up. My libido was hungry. When did I become such a horn ball. After 25 years of basically no sex, you think I’d be fine going home with just my right hand.
I had an ace in the hole though. I texted the Middle Eastern guy from the pervious night and asked if he wanted to come over again. I don’t think I lifted my finger off the send button before I got a response back. He was certainly interested, but had to come over later after class. He wouldn’t arrive until around 10. That was fine. I figured out other things to do with my time, like eat dinner.
When he arrived, we went straight to my room, but I’m sure, much to your surprise, we didn’t immediately jump in the sack. We kissed for a bit, but then we simply laid next to each other cuddling while we watched Modern Family. We are both big fans!
Every time there was a commercial, he took the opportunity to kiss me passionately. There were no complaints from me. He was a great kisser. He had perfect lips and knew what he was doing. We also took the time to chat a bit. I wanted to get to know him a little. He lived with a bunch of guys in an apartment and even shared a room with a guy. None of them knew he was gay, and he recently broke up with a girl. He told me he’d been on a handful of Grindr meet-ups, but none were anything like what we shared. He told me how much he enjoyed the previous night and how much he thought about me all day long. It was very flattering, and a little alarming. This kid was falling for me — and fast. I needed to make sure things didn’t get out of control because I didn’t want to hurt him.
I couldn’t tell him what I was looking for because I didn’t know what I was looking for. I really wanted to find a boyfriend, but I wasn’t sure he fit the bill. This was new territory. I’d never dated anyone so much younger than me, let alone still in college. He was a really nice guy, and I could tell his friends loved him, but I was still conflicted. He was very mature, but nonetheless, he was still in school.
When the show was over, the making out led to heavy petting. Things escalated, and I invited him to spend the night. While naked, he walked to the bathroom to take out his contacts. I watched him from the bed, staring longingly at his body. I told him how hot I thought he was. He really riled me up. I loved the innocent confidence he exuded. It was incredibly sexy.
He told me he wanted to go to bed horny so we could wake in the morning and have some real fun. It was late, and I was tired, so I didn’t oppose. With that, he rolled into little spoon position, and I pressed my naked body against his in big spoon position. It felt so comfortable. It felt so right.
In the morning we both woke to the sound of my alarm — strategically set early to allow for time to play. We were both in a very frisky and playful mood. He certainly wasn’t shy about kissing. He loved it and did it often.
Warning: The following may be too graphic for some. While we embraced each other, he whispered in my ear how he wanted to ride me. I certainly was in no position to deny him this privilege. I was looking forward to it. I was shocked, him being so new, how much he was gung-ho about bottoming. I think he discovered he’s really a bottom. He hopped on, and it felt great. He came really close to finishing, but never did. I knew exactly what was happening, so I didn’t put any pressure on him or comment on it. That would only bring it to top of mind and make it worse.
He had to stop. He wanted to keep going, but told me he was sore. He informed me that I was a big guy. I’d never really thought of myself as big. I always thought of myself as average. But, as of late, I was informed otherwise. (This is not something that is important to me, but it is quite the ego boost to hear).
We laid next to each other once again pleasuring ourselves while he laid in the crook of my arm. I finished after a few minutes. I was happy things were turning around for me. It wasn’t taking a long time for me anymore. I was far from a one-minute man, but my mental block was easing. This wasn’t the case for Middle Eastern (will be called M.E. from now on). He never finished, but also never complained. He noted, “I can never [finish] after you’re inside me. I can’t explain it. It feels amazing, like a full body orgasm, but I just never shoot.” I knew exactly what he meant. I told him it’s just part of sex sometimes. I wanted to ease his mind.
With that, we both hopped in the shower, and I took the opportunity to wash him from head to toe with a bar of soap and my hands. It was really sexy and slightly romantic. We both enjoyed it. Then he did the same to me. It felt great!
While I get ready in front of the mirror, he noted its existence. He complimented me on what I was wearing to work. He really was charming and sexy. I was really starting to like this kid. I just worried we wouldn’t be able to have a real relationship. He was in the closet and in college. He told me he wasn’t hiding it anymore, but he was advertising it. I understood, but I just wasn’t sure if it was for me
Follow @onegayatatimeSo When Are You Moving Back to New York?
Posted by One Gay at a Time in Gay Dating on April 9, 2012
Finally, work sent me somewhere fun, and I was taking full advantage. I stayed out in LA, managed to have some fun, and even managed to find myself a pretty great guy, The Navigator, to hit up the beach with. After swinging by his apartment, we agreed we weren’t done hanging out.
We made our way back to my hotel. After we turned off his street, I came to a stoplight. I took the opportunity to reach over and put my hand on his leg. He immediately responded positively to my advances. He reached down and laid his hand on top of mine and gave it a squeeze. We continued to hold hands the entire way back to the hotel.
We made our way to the room, and when we arrived, we quickly got comfortable with each other. We dropped our bags and laid down on the bed. We chatted a bit before he reached over, pulled me in, and we exchanged a long deep passionate kiss. When we finally came back up for air, I said to him, “I’ve been waiting to do that all day long!” He smiled from ear to ear and pulled me right back in for another deep kiss. He was a great kisser — Not just a good kisser, but a great kisser.
Was there anything wrong with this guy? He certainly wasn’t going to make leaving easy on me. I still had to keep myself in check. This thing would have an end. I couldn’t grow too attached, or I would be in for a world of pain.
The thing I liked most about the chemistry between us was how playful we were. There was no drama. We were just having fun. Everything was so easy. We cuddled and talked and tickled and joked. I felt incredibly comfortable with him. We just seemed to be on the same page about everything. He was certainly giving me hope that I could find a guy out there who I just clicked with right off the bat.
All day long, he had been texting with his friend giving him updates on our “date” as he so-called it on the beach. While we laid there he teased his friend about how good-looking I was, but lied and told him I’d just dropped him off at home while I listened on speaker phone. The exchange between the three of us was very comical and flirtatious. He showed me pictures of the guy we were talking to, and we sent pictures of me to his friend. We all had a good laugh, and his friend asked for continued updates.
The kissing slowly turned into making out. The making out evolved into heavy petting. The heavy petting became stripping. The stripping led to oral pleasures. And finally, the oral pleasures led to me learning he is versatile, which of course led to penetration. My provisions weren’t presumptuous at all. I suspect he noticed my condom/lube purchase at CVS, and this is what gave him the courage to propose going back to my hotel room.
The sex wasn’t the most amazing because I was having difficulties with the condom, but it certainly wasn’t bad. We were passionately enjoying each other on many levels.
After we had sex, we laid next to each other talking more. We attempted to take some pictures together to send his friend, but we couldn’t keep our eyes open because the flash was too bright. After our romp in the sheets and copious amounts of cuddling, I was hungry. I remembered an In-and-Out burger down the street. It was 1am, and they were one of the few places still open, so we got dressed and made our way there to grab dinner.
We took our food back to the room and had a picnic in my bed. We talked and made plans to go hiking the following day. The whole night, all I could think about was how crazy it was I even met him. It was even crazier how we both dove in headfirst. He even mentioned being worried I might be a serial killer for the first couple of minutes in the car. After we finished eating, I jokingly confirmed he was staying. He went to his bag and got changed and broke out his toothbrush. It seems he may have been presumptuous as well in packing his bag.
I didn’t care one bit. I was thrilled to be sharing my bed with such a great man. I only wished it was for a longer-term basis…
Follow @onegayatatimeLate Night Snack
Posted by One Gay at a Time in Gay Dating on April 3, 2012
After my tryst with the Armenian and the Asian, I decided to order some real dinner. This was the last night I was on the company dollar, so I ordered some room service. While I waited, I chatted with the guy who wanted to come by later in the night. I sat and ate my meal in bed with just the TV to keep me company. I was feeling lonely, which is such a strange emotional state to be in considering I’d just shared one of the most intimate acts with two other men.
When midnight arrived, I started texting my late night snack. I asked him what he thought his E.T.A. would be. He told me it was still up the air, but he was definitely coming by. He was out with friends and would swing by on his way home.
Finally, around 2:00am, he texted he was finding parking and would be by shortly. Ten minutes later, I had a knock at the door, for the third time in a matter of hours.
He was a very nice polite black man who was anxious to spend some time with me. He seemed very young and innocent. We chatted a bit while sitting on the bed before any action began. It was getting late, and as rude as this sounds, I was ready to get it in and go to bed. I wanted a nightcap so I could doze off soundly till the morning.
Warning: The following may be too graphic for some. We had A LOT of foreplay and prep before anything happened. He really wanted to cuddle for a long time before we could even get frisky. I was almost ready to call it quits and ask him to leave. It was getting late, and I was getting tired.
There was a lot of kissing. A lot of heavy petting. A lot of licking and sucking. Finally, he was ready and got into position for me to penetrate him. I could tell this wasn’t a guy who gave it up to just anyone. Normally, I’m really into the foreplay and making out, but I’d already had my engine warmed up earlier that evening. In fact, the car had been taken around the block a few times.
I’d saved my climax for him and quickly learned this was a big mistake. He was very bad. We didn’t go for very long because I really wasn’t getting anything out of it. Finally, I stopped and rolled onto my back. I tossed yet another condom in the trash and started taking care of myself. He laid next to me and asked me to finish on his chest. I obliged his request, and he followed suit shortly after.
I knew he was going to be a lingerer. I tried to cut that off at the pass. I humored him for a short bit of time before I finally spoke up and said how I needed to get to bed. It was past 3:00am. It was time for him to go! He got the hint and got dressed. While he did so, he asked if we could hang out again while I was in town. He told me how much he enjoyed himself. I didn’t shoot him down, but I didn’t exactly give him the answer he was looking for. I told him I’d have to see what my schedule allowed for. I told him I was trying to get the most out of my vacation in L.A.
With that, I said goodbye, shut the door, showered all the men of the night away, and climbed into bed to dream about the sunny sandy beach I would be visiting the following day.
Follow @onegayatatimeThe Horror!
Posted by One Gay at a Time in Gay Dating on February 28, 2012
Touchdown! After a long flight of writing a lot of blog entries, I finally landed in San Francisco. I was very happy to be away from New York. This was forced time to clear my head. It would be impossible to try to find a guy for a date from thousands of miles away, and I needed a break. Don’t get me wrong, I want a man to call my own, but the process of finding one is exhausting.
I rode to my hotel with a very chatty driver. He had lots of questions and comments for me. Many of the comments referred to women and our “shared” desire for them. I didn’t have the heart to tell him I was gay. I just let him continue talking. It wasn’t that long of a ride.
I got to my hotel, and took my good ol’ time getting to the office. They didn’t know exactly what time I landed, and I’m sure they wouldn’t have any work for me yet anyway.
I was right. When I arrived at the office, they had no work for me the entire afternoon. This worked out quite well. It allowed me to update the blog and go for a nice long delicious lunch I didn’t have to pay for. When the workday was coming to a close, I made my way back to my hotel.
I’d been on Grindr all day hunting for a guy to either meet for a drink or have some fun with. Nothing was turning up. I recalled the last time I was out there. Originally, I had the same luck. That is, until I picked up signal from San Francisco. No such luck that day.
I thought about the other weapon in my arsenal. I could pull up adam4adam.com and see who was in the area. I managed to find a few sexy men to message. It was only a matter of time before one of them messaged me back. A few did, but many of them were flakes. A few of them were unattractive as soon as I saw their faces as well. I asked a few to hang out, and the ones only interested in sex, I proposed coming to my hotel. Some of the guys on Grindr offered bl*wjobs, but I was looking to get it in.
One guy was very willing to make the journey to my hotel, and he was a bottom and looked pretty sexy. I told him to come by and gave him the details. I had one failsafe. They would not be able to come up to my room without me picking them up from the lobby. If I was unsatisfied with what showed up, I could hop back in the elevator and shut the door. That’s terrible, I know, but you never know what will show up when push comes to shove.
I was doing it again. I ended a relationship and simply fell back into old habits of hooking up outside of a relationship. I wasn’t thrilled with myself, but I was giving myself a free pass while in San Francisco.
I would have to put off dinner until after my evening tryst arrived. I was hungry, but I wouldn’t have time to get dinner before he came by. When he arrived, I collected the man from the lobby. He was a good-looking Aussie.
We got up to my room and talked about where we were from and our stories. He sat on the bed and talked with me. He seemed like a pretty cool guy. He was a bit of a vagabond. I liked his traveling experience. I was envious of it.
When the moment was right, we both went in for a kiss. This was followed by LOTS of kissing. Lots! He seemed quite nervous. I was trying to get him to relax a bit. I took my time with him gently feeling his body. He was a good kisser. This was a good sign.
Slowly I began peeling off some of the many layers he was wearing until we were both naked. He had a decent body. He was skinny, but not exactly muscular and defined. The kissing became more passionate and the petting grew heavier. When we were pretty far along, I whispered in his ear, “I want to be inside you.” He responded the same sentiment, so I reached for the condom and lube I had in the nightstand drawer.
Warning: The following may be too graphic for some. Now I know I say this in a lot of posts, but this time, it may be too graphic for even those who are normally turned on by my warnings. Just be forewarned. Don’t say I didn’t tell you so!
I inserted myself inside him. He felt great. He seemed to really be enjoying himself as well. We were about two minutes in when something didn’t feel quite right. I took a whiff of the air, and immediately knew what was wrong. I looked down in horror, and it was all I could do to keep myself from vomiting all over this man.
I immediately pulled out and hustled to the bathroom. We both knew what was wrong. I tossed the condom in the trash and began scrubbing myself. I casually suggested a shower. I was trying to maintain my composure so this man wouldn’t feel worse than he already did. This was horrific, but I still had the man’s ego in the back of my mind.
He suggested I go first. I’m not sure why. All I could think about was his uncomfortable state while I showered. He made his way to the toilet and took care of himself while I washed up in the shower. When I finished, I left the bathroom so he could do whatever he needed to do.
I was still a little shaky and trying not to think about what just happened. I’d encountered this before, but never to this extent.
When he emerged from the bathroom, you could have knocked me over with a feather. He actually suggested we keep going. I was speechless. I didn’t know what to say. At this point, I no longer had the man’s feelings in mind but only my own sanity. I told him, “No. I think I’m done for the night.” He didn’t stop apologizing. “Don’t worry about it. It happens. Part of the territory,” I reassured him while he got dressed.
And then, when I didn’t think this man could surprise me any more than he already did, he suggested we grab food since he hadn’t eaten anything yet either. “No. I think I’m just going to order room service or something but thanks,” I added.
Just as he was walking out the door, my phone rang. It was San Francisco. I explained to my departing guest that I needed to take the call and gave him a wave goodbye. I couldn’t wait for him to be out of my sight so I could stop thinking about what happened.
“Helloooooo. How are you? Are you Grindring?” he said as I picked up the phone. All I could think in the back of my head was, if you only knew! I simply replied, “I’m single. I can do whatever I want.” We talked about our schedules for the week and planned a night we could grab a drink together. He suggested we meet in The Castro since I didn’t make it up there during my last visit. Once our plans were solidified, I hung up and tried to figure out what to do for dinner.
Joe’s Crab Shack was a block away and was one of the few places still open at that hour. I decided to go there. This would be the second mistake of the night, as this was the worst seafood I’d ever had. I couldn’t finish it. I was literally wiping the seasoning off the crab legs with paper towels, and I still could barely tolerate them.
If this was a sign of what was to come from my San Francisco trip, I was going to lock myself in my hotel room when I wasn’t at work. The positive was, it certainly couldn’t get much worse…
Follow @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 