Posts Tagged hookup
Turning Over a New Leaf
Posted by One Gay at a Time in Gay Dating on October 5, 2011
With the passing of Labor Day, summer officially ended in my book. I was sad to see it go. Like always, it flew by in no time. Its passing wasn’t all sadness, however. My favorite season was right around the corner. The changing of the leaves, the crisp air, the smell of fireplaces… all things I loved about the fall.
Just as the seasons were transforming, so too was I. Since I broke up with N, I went off the deep end. Part of this is because I never had my wild time. While everyone else was hooking up and experimenting in high school and college, I was being a good boy. I sat there and watched everyone else experience relationships and casual sex. I was asexual. Sure, I had my fair share of hookups with women, but nothing worth writing home about.
When I finally accepted myself and came to terms with my homosexuality, I found myself in a relationship right off the bat. I never had a chance to meet new guys and discover new things. Following my breakup with Broadway, I had a short window of wild time, but it was mainly filled with dates that ended with me going home alone. Then came San Francisco, shortly followed by N. This summer was the first time I was single and gay. Did I live it up? Yes. Am I proud of everything I did? Hell no, but I also have no regrets. Everything was an experience, whether it was something I learned from or something that made me a better person.
I began to look back and examine my summer. I wasn’t being true to who I am — True to myself. I don’t have casual sex. I’m a monogamist. I crave a meaningful relationship with a special guy who appreciates me, body and soul. If I kept sleeping around, I was never going to find this. I need to make a change. I thought I would be able to ease into it when I returned from Martha’s Vineyard, but I was wrong. I needed to be more drastic. I was going to be a good boy, even if it meant the palm of my hand would be raw.
I had two friends with benefits. I needed to cut them off completely. Closet was still messaging me since we last hooked up. “Hey man, haven’t talked to you on a while. Hope all is well. Don’t want to sound insecure or anything(too late), and I know you said its not a bother to text/email you, but just FYI in case that ever changes just let me know you’re lookin for something different or you’re seeing someone else. Lol feel free to lie to me, just would rather know if you’d rather me step back… I don’t want to become one of those creepers that I keep hearing about haha. Anyway hope to see you sometime, even to meet out for a drink or something. Later man.”
I originally found both my friends with benefits on adam4adam.com, so I sent them both messages on there. I lied and told them I was seeing someone, and I wouldn’t be able to see either of them anymore: “Hey dude. Sorry I haven’t hit you up. Everything is fine. I have started seeing someone, and I decided I need to stop with hookups outside a relationship regardless of that person. I think you’re a great guy, and I had a great time with you! Don’t doubt that. I just need to find a serious relationship right now, so I’m concentrating on that. I hope you understand!!!”
While the muscular weekend hookup simply replied, “No worries,”
Closet had a few more things to say: “Hey bro, its cool. No hard feelings. I mean can’t say I’m not disappointed, cause putting the physical aside, you really seem like a great guy, and I’m glad we met. Honestly, I felt weird saying it to you before, but now what the hell hehe…you’re the first guy I was with that made me think I wanna come out(not to mention my first for a few other things, lol). Obviously not saying I was in love after a few hookups lol, but I felt something more than just empty sex. I’m considering it after the holidays this year (you know, one last Christmas where the family likes me, hehe), but I’ll revisit that one later. Anyways, you’re a great catch, and I hope you find a great guy – and my offer remains open if you wanna grab a beer, just as a friend, hit me up. Thanks again dude, and I hope our paths cross again sometime. P.s. Two more things… 1. Thanks for being so patient with me in bed and all that, even though I still need to loosen up a little (pun intended), you really made me feel comfortable. 2. If you ever run into me while out at bars or whatever, cuz I’ve been in Hoboken quite a bit lately, feel free to say hi. I’m trying to gradually cut back on the paranoia part of all this.”
I felt pretty bad about the situation with Closet. It was obvious he was starting to fall for me, but I had no interest in pursuing anything with him. I knew I was right to cut it off when I did.
Outside of my regulars, I gave up Grindr cold turkey. I knew it would be too tempting to fall into something if they were hot and looking to hookup.
I joined OKCupid, was checking ManHunt and adam4adam.com regularly to see if there were any guys reaching out to me I’d be interested in meeting. It wasn’t easy finding a man up ’til now. I couldn’t expect it to get any easier just because I stopped hooking up with random men. None of the men I went on dates with previously showed any interest in seeing me again. Pillow and The Trainer kept giving me the runaround, so I had to learn when to simply give up and move on.
I started to wonder what was wrong with me. What was I doing wrong? Without the sex and without the happy feeling I get when I have a prospective guy I’m seeing, I started getting cranky. This was going to be a learning experience for me. I needed to not only find a man, but also to find myself. In the meantime, everyone around me would to have to watch out. I was not a happy camper…
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Posted by One Gay at a Time in Gay Dating on September 27, 2011
After meeting the ginger, I was talking to a very attractive resident of Martha’s Vineyard who is originally from Russia. He is very attractive and very sexual. I attempted to invite him to meet us at the beach or come out with us to the bar for two straight nights, but he declined every time.
Instead, while out to dinner one night before hitting the bar scene, I came across a guy on Grindr who happened to be at the same restaurant. He seemed nice enough. When we finished our meal, I walked up to the bar to meet him and introduce myself. My friends weren’t far behind. It took all of three seconds to realize I would not be interested in this man from New York City.
As soon as he opened his mouth, it was quite evident he was a big ol’ mo. He is a 6’4″ ball of flaming queen. I couldn’t get out of there soon enough. Of course, I was too polite to simply walk away, and we exchanged numbers. And, just my luck, he was heading to the same bar my friends and I were going to. I did my best to hustle my group along except one of my friends stepped in to “help me out.” She didn’t quite realize how uninterested I was in this guy.
Our group split, and half of us went to the bar — The other half went home to bed. The Grindr guy and his straight friends followed shortly behind us. All the straight guys began hitting on the girls with me. I put a pylon between the Grindr guy and I so I wouldn’t have to engage him on conversation further. He started to chat with one of my female friends while I stood in the background and made myself as unattractive as possible. My friends and I were trying to see who could look more pregnant. Classy, I know. When we all finished our one beer, we moved on, but not before Grindr Guy grabbed me and tried to plan a beach trip for the following day. He was going to text me where they were, and we were expected to join them. That never happened.

So, just when I didn’t think I could dive any deeper into casual sex, I come to surprise even myself. The following morning, I was chatting with a good looking guy from Boston who was very discreet and had a girlfriend. He was looking for some action. I was only half interested. I was still trying to make things happen with the Russian. We were heavily flirting and exchanging pictures. He asked if I found any other hot guys on the island. I replied, “I’ve yet to see any serious talent since I’ve arrived.” I wasn’t about to share the Russian with him. That’s all I needed was for him to scoop him out from under me. He was very interested in me, but explained he was already making plans with another guy to have some fun in the woods.
At that point, he proposed the three of us get together. I didn’t know how to react. He already established he was not interested in sex but was looking just to fool around — “circle jerk” as he put it. I cautiously agreed to participate but needed more specifics before I would feel completely comfortable. At that moment, the Russian started responding.

I tried to see if he was interested in meeting up that morning instead of the party in the woods. I would go for a run to his place and spend some time there before anyone was even out of bed. That’s when I found out he was going to be the third party in the circle jerk. It’s also when the guy with the girlfriend started scolding me for trying to steal the Russian away from him. I explained I had been talking to him for some time. He of course called me on my earlier comment about the island’s lack of talent. It was slightly awkward, but we got passed it.
I learned the other two had already chosen a spot in the woods to meet. It happened to be 3.5 miles from where I was staying. I also learned I had slightly less than a half hour to get there. I threw on shorts, shoes, popped in my iPod and took off towards the site. I arrived shortly after the other two. The spot they chose was a construction site in the middle of the woods. It looked like a giant sinkhole.

When we all gathered, we tried to find a place to get out of site. I vetoed the original plan of walking into the woods, namely because I didn’t want to spend the rest of my vacation covered in poison ivy rashes. In the center of this hole in the ground were construction vehicles. Although they were the center of attention from all sides of the site, we managed to duck between them and get out of site.
(Just a warning, the following may get graphic) Almost immediately, the other two dropped their shorts to their ankles and began to jerk off. I followed suit. Every began to participate and aid each other in different combinations between the three of us. I was dripping with sweat from my long sprint, which surprisingly was a turn on for the other two. It brought me a little more attention as well. This was the first time I participated in anything with more than one other, so I was slightly intimidated. However, it was easier to relax a bit because I knew it wasn’t going to escalate to penetration. We all had our fun and eventually finished ourselves off in succession. I was on quite a high. Between hooking up in public, doing it with two guys, the run, and climaxing, I was in a different world. I had no idea how I was going to make the run back home. My legs were weak.
We decided it wasn’t a good idea to linger, especially the paranoid guy who had a girlfriend. He split off and the Russian and I casually walked back to the highway. He offered to give me a ride, and I graciously accepted. This would also help cut down on the time I was away. We had casual conversation the whole way back about our inability to connect with just the two of us earlier in the week and the other guy’s situation playing both sides of the fence. He dropped me near the house I was staying at, and we agreed to touch base later about hanging out.
I ran back to the house and hopped right in the shower. While I stood in the shower, I thought back on the morning’s events. It played out like a Sean Cody gay porn. The only thing missing were cameras. Everyone was just waking up and getting ready for the day. It wasn’t even the weekend yet, and I already had my first ginger and my first three-some. Who knew what the rest of the trip would bring. Only time would tell…
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Posted by One Gay at a Time in Gay Dating on September 6, 2011
Just when I was doing well and turning my back on my whorish ways, I got sucked back in. At work Friday I received another one of N‘s annoying, yet typical messages that pushed my buttons. I was still coming off the high from Wednesday’s successful date. He always knew just the right moment when I wasn’t thinking about him at all to poke his finger in my face with a sarcastic comment I was just expected to slosh off as a joke. On Thursday, through my blog, he managed to figure out who I had sex with while we were dating. He sent me a screen grab of his Grindr and asked if I recognized him. On Friday, he apparently wasn’t done talking about it and felt the need to bring it up again.
I had a half day, and I wanted to do something with it. N p*ssed me off, and I was in the mood for sex. I sat in Herald Square on my Grindr to see if I could stir something up. No dice. It was time to go home and pull up some porn.
When I got home, I went thought my daily routine of checking my messages on adam4adam.com. I had quite a few. One in particular was a very muscular man who lived nearby and happened to be online. We chatted a bit and unlocked our pictures for each other. He seemed like a really nice guy, and we were thoroughly horny at this point. So, I invited him over later that evening when my roommate would be out.
I can remember around the time I came out when I was talking to a guy in San Francisco. He used to have random guys come over for sex periodically. This blew my mind. It was inconceivable to me. I’m sure to some of my readers feel the same way. But now I was that guy. I’m not saying I’m not ashamed of it by any means. But it has become an easy way for me to get off, and it’s something I need to stop doing. Just not that day.
After my roommate went out to dinner, the guy from a4a came over. He came into my room, took his shoes off and hopped into bed with me. We were making out until both our shirts came off and our naked chests were pressed together. He felt so good. He was an older guy, but he was in great shape and everything was tight and muscular. We pleased each other orally and then moved on to penetration. I pulled out a condom and he begged for me to enter him. It was great sex. His smooth body was better than I expected. I was able to make him finish without even touching himself. We both really enjoyed ourselves.
Afterwards, he hopped in my shower and washed up. When he was getting dressed, he commented on how great he thought my body was. He was pleasantly surprised I lived up to my pictures, and suggested we make this a regular thing. I wasn’t opposed to the idea, but I was still making an effort to turn over a new leaf. At least with him, it wouldn’t constantly be a new or random guy.

The next day, I went to the beach. He started texting me, “Damn bro. Don’t usually text next day, but in the shower fully hard thinking about yesterday. HOT!” It was just the ego boost I needed. He added, “Anytime you want a repeat. So close n convenient too!” This was also followed up with a myriad of sexy pictures. I scolded him for getting me excited on the beach when there was nothing I could do to alleviate the hormones.
When Sunday morning rolled around, my roommate went out with my sister for brunch, leaving me home alone. I texted my new friend with some amazing benefits to come over for another visit. Of course, he obliged. We were having yet another sexy romp when we were interrupted by the sound of my roommate coming into the apartment. He was fully aware of what I was doing, but I didn’t exactly feel comfortable with him hearing us. I suggested we move to the shower, and Mr. Smooth agreed heavily.
We turned on the hot water and had a hot wet time. We both finished with fireworks in the shower. When I toweled off, I checked my messages and noticed my roommate tried to call numerous times and left a text message. He just left to go surfing at the beach without me. I managed to call him and convince him to come back to get me. He was only ten blocks away. I started to rush Mr. Smooth. I felt bad, but we both knew what this was. I got dressed for the beach in one minute flat, and he quickly put his clothes back on.
As we walked down the stairs, he grumbled about the walk of shame in front my roommate, but was over it right away. As I drove to the beach, I sent a text message apologizing for the circus, but also complimented him for yet another hot time in bed. He was fine with it all.
Maybe I would keep this one around for lonely times, but I would also try to find the strength to find a real man to be my boyfriend and stop with the hookups altogether…
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Posted by One Gay at a Time in Gay Dating on August 26, 2011
On the way to Rehoboth, the guy from the run texted me. I explained the situation and his lack of commitment. At this point, I was in over my head with the hicks. I told him to meet us in Rehoboth. I needed to be rescued, and he eventually came to my rescue.
We arrived at the bar, The Purple Parrot, and he arrived about a half hour later. I noticed the guy who originally was talking to me on Grindr was laying claim to me. I overheard some alarming conversations that made me realize he expected some sexual action from me. “I swear to God, if he goes home with this guy after we brought him up here!” This was NOT happening. I clung to my new friend like white on rice.
The hicks went inside to do karaoke, and my new friend and I followed shortly after. We found a bachelorette party of the sweetest girls to entertain us. We all became good friends fast, which was perfect because the hicks were ready to leave. I explained I was going to stay and would meet up with them later in the night. The one who laid claim to me tried to hang back with us and even asked for a ride home, but when he couldn’t get a guarantee, he got p*ssed and left. Later in the night I received a text scolding me for never meeting up. I retorted explaining why, and my reasoning was that I was not a piece of meat for him to lay claim to.
We spent the rest of the night singing karaoke with our new bachelorette friends and taking lots of pictures. We had a blast. When it was getting late, he asked if I was ready to go home. He was a really sweet guy, and I had a good time with him. Even if I had to deal with the hicks for most of the night, I was happy to get away and got to spend some time with a new friend.
On the way home, I rubbed the back of his head while he drove, and we chatted. I wasn’t sure where this was going, but there was no way in hell I was having sex with anyone. He drove right past my condo when we got back to Ocean City and went straight to his place. When we entered, he was startled because he mom was still up. We hid in a side hallway until he could devise a plan. He told me I was going to be “Steve” his friend, and we walked past her up to the loft he was staying in.
Once we got up there, we started making out a bit. He pulled his pants down and started playing with himself. My pants were off, but I still had my boxers on. I decided to give him a hand. He finished all over his shirt and pretty much passed out. I was really hoping he’d be a gentleman and drive me home, but that wasn’t going to be the case. I would have to walk 2.5 miles home at 3:00am. I told him I needed to wake up in my own bed, got dressed and walked out.
At this point, I was very horny. Along my walk, I received a message from the guy who exchanged blowjobs a few nights before with the man I just left. I heard how hot he was, so I entertained the idea of meeting him. His roommate was home, so he convinced me to meet him in the dark alley behind his apartment building. When I got there, he was standing with his dick in his hand. He was really hot. We started making out. He undid my pants and gave me a blowjob. After some time, I returned the favor and then continued working with my hand. Shortly after, he finished all over the sidewalk. It was really hot. I thought I was going to receive the same treatment, but instead, he told me he had to get back inside before his roommate noticed he was gone. This was now two guys in one half hour that I helped with a “night-cap” who didn’t feel the need to reciprocate.
On the next leg of my journey, my mother called. I explained that “Will” had too much to drink once we got back to O.C., and I wanted to sleep in my own bed, so I agreed to hop on the bus. However, all the buses were packed to the gills, so I told her I was walking home. She stated, “You’re an adult and you can stay out as long as you like, but you need to tell us when you’re going to be out this late. Your father and I haven’t been able to sleep.”
The entertain myself for the rest of the 2 miles I had to go, I turned to Grindr. I had received another message from yet another hottie while I was hooking up in an alley. At this point I was a complete whore. Why not tack on another one? This guy was horny and looking for action. I explained where I was and where I was headed. I told him he could come pick me up, but asked where we could hookup. I suggested his car, but being a local, he convinced me it was cool if we hooked up on the beach. Just as I was getting to my street, he drove past me and turned towards the beach. I followed and met him by the sand.
We introduced ourselves and began to walk through the dunes. Just then, the garbage trucks were driving across the beach to empty all the cans. We stood and waited for them to finish before we started making out. He was a good kisser, and he quickly moved on to orally pleasing me. He was good. He was very good. Finally, someone was interested in my pleasure that night. After a while, he stood. I dropped his pants and returned the favor. I never hooked up on a beach before. It was an exciting new venture for me. After a while, I asked if he was a bottom. I explained I wasn’t going to have sex with him, but I wanted to grind on each other a bit. He agreed and turned around. I pressed my body against his and gave him a reach around. He finished all over the sand. It was my turn. I started to take over for myself while he played with my balls. It felt great. When I shot all over the sand, he said, “Wow. I’ve never seen anyone shoot like that before.” I replied, “Yea… That’s my hidden talent.”
After the two of us decorated the sand, we got dressed and started to walk back towards his car. We talked about why he was in O.C. and how he was moving to NYC in September. I told him to hit me up when he did. I was always looking for new friends to hang out with. We said goodbye with a kiss, and I walked home.
When I got home, I opened the door quietly and hopped into the sofa bed I was relegated to since my sister arrived. My mother came out to scold me one last time before dozing off. I felt like such a high school boy sneaking around to hookup and getting yelled at for breaking curfew.
The next morning, the last day at the beach, the guy I met on the run wanted to meet up and make up for not finishing me off the night before. This was a constant circus of juggling locations and sneaking around. It was becoming nearly impossible. The solution we came up with; he would pick me up in his car and we would hookup in his car somewhere. That somewhere turned out to be a parking garage, and that hookup turned into a blowjob for me. We both finished in the car by our own hands. He was heading home straight from there, while I was heading to the beach to meet my family. He dropped me off by the sand, and we said our goodbyes. He encouraged me to hit him up the next time I was home in Pa.
I was ashamed and embarrassed of my behavior on my vacation, but I got it all out of my system. I wasn’t planning to hookup at all, but even went as far as to do it three times in one night. What a whore! Once again, things needed to change, but I just told myself it was vacation. I was allowed to take a vacation from my morals for a week…
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Posted by One Gay at a Time in Gay Dating on August 25, 2011
It was that time of year. The annual family trip to Ocean City, Maryland. Every year I both looked forward to and dreaded this vacation. While it was a week to disconnect and relax, I knew I was surely in for some excessive boredom. Don’t get me wrong, I love my family, but we’ve been going to the same place for years. I can only take so much of it before getting tired of it.
We arrived on a Sunday, and one of the first things I did was turn on Grindr. I’m addicted. I know. It’s an issue, but I also knew it would be my salvation from the boredom that would ensue. After riding in the back of the car with crap piled around me feeling like a twelve year-old, I needed to get out and do something. My parents plopped down in front of the TV, a position they would take for the next three nights as well. I wasn’t feeling so lazy. On top of that, I was already getting grief for playing on my phone while we sat and watched TV. I needed to get out.
I managed to find a nice guy on Grindr not far from where I was staying. He was from Pa, not far from where I grew up. He certainly wasn’t around the corner, but he wasn’t far either — 2.5 miles. I decided to go for a run. I could run down to his condo, say hi and turn back. It was also a good way for me to squeeze in a run as well. I told him I was going to run down there. As I got near, it appeared he was going to chicken out on me. I told him, “You’re really going to flake on a guy who just ran 2.5 miles to say hi to you!?”
Eventually, he came out to say hi. I think he had ideas in his head of us blowing each other on the beach, but I was just there to say hi. We walked around the block and talked about a few things. He was no adonis, but he was certainly a nice guy. I thought it would be nice to grab a drink with him later in the week just to chat. I wasn’t looking for anything sexual while down here on vacation. I was turning over a new leaf, remember? I said goodbye and ran back home.
The next day, a local guy found me on Grindr. He was a bit of a sweetheart. We swapped a lot of pictures, and he expressed his interest in getting naked with me. This would be very tough. I would have to plan a way to get away from the family without raising suspicion.
That’s when I created my friend “Will” from college. He was down in OC with his family. He was based on a real guy, so it wasn’t difficult to come up with material on how we knew each other, but he was not real.
Monday night, the guy I met on the run hit me up for a hookup. I told him that’s not what I was looking for. He managed to find service elsewhere. A guy invited him over, and they gave each other head. He told me how incredibly hot this guy was, but also about how he wasn’t fully comfortable with his sexuality.
In any case, “Will” and I were going for a run that Tuesday morning followed by breakfast. In reality, I was meeting this cutey for breakfast at his favorite local spot and then heading back to his house if we hit if off for some fun. Breakfast was very nice and we hit it off. I followed him to Ocean Pines, a ten minute drive from breakfast.
We went into his room and had great sex. It was just what I needed. We both really enjoyed ourselves a lot! The time came to say goodbye and head back to the family. On the drive back, I was beaming. Sex always looks good on me. Just then, N texted. He totally ruined my high. I was on this vacation to completely forget about him for a while, and he was making this nearly impossible. This was the second day in a row he texted. I called Boston to brag about my morning romp and bitch about N once again. Poor Boston.
That night, the guy from the run explained to me his boyfriend was arriving. This was the first time he brought up the fact that he had a boyfriend. My relationship wounds were still fresh. Infidelity was a BIG turnoff. He proposed we all go out, but we would have to meet “by chance.” I said, “What? So I sit at the bar looking all sad, and you two come sit next to me and chat me up? Not gonna happen.” Besides, Tuesday night was an annual tradition for my father and I to go to Hooters for wing night. He knows I am gay, which makes it even more ironic, but we always have a good time. It’s the one time of year he orders a beer when we go out. There is an element of humor added as well. My mother loves the wings, but she refuses to step foot in the fine establishment, so we order too much food and take the leftovers home to her.
By Friday, his boyfriend was back home in Pa. We made plans to grab a drink together, nothing more, but he was having a hard time committing to anything. In the meantime, another guy was hitting on me on Grindr. He was good-looking in his picture, and after talking for some time, he asked me to come with him and his 3 friends to Rehoboth for the night. I debated in my head just how risky this was. Looking back, it was a really dumb idea, and I never should have done it. But, life without risk is life unlived.

They picked me up and we went back to their condo for a few drinks before heading up to the bar. When I met all the friends, I knew I got myself into a bad situation. These guys were all hicks from right outside D.C. I wasn’t scared, but I also suspected I wasn’t going to have a good time… To be continued…
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