Posts Tagged Sex

Visit From the Closet

As I watched my roster shink over the summer, I began to revisit old friends. Adam4adam.com came back into my daily routine. I noticed I received a message from a 28 year-old guy who was still in the closet. His profile read: “Just lookin around, new to hookin up with guys and not out at all, so not really sure where I’m at right now. I do know I’m definitely extremely discreet and expect the same. Other than that, just playin it by ear.”

I knew this guy was going to be a delicate dance. His picture looked pretty good, and I was interested, so I reached back out to him. We exchanged a few emails about our current situations and talked about how fresh we both were in the gay world. I think that’s what he was looking for. Throughout every conversation we had, he stressed his need for discretion. I explained, “I spent 26 years in the closet. If anyone knows discretion, it’s me.”

We never made any plans during any of our initial conversations, but on a random Friday night, I found myself not interested in going to the bar. I had the apartment to myself, and I was bored so I hopped on a4a to check my messages. He happened to be online at the time, and I happened to be very horny, so I told him to come by. He had to shower and drive to Hoboken, but he was game.

This wasn’t my first rodeo. I was finally comfortable with these situations (not that that’s a good thing), and I realized I didn’t need to put in so much effort. When he arrived, I was sitting on the couch in gym shorts and a tank watching Jurassic Park. I poured us both a drink, and he joined me on the couch. We had casual conversation for a bit. Surprisingly, he made the first move. He put his hand on my leg when we were talking and left it there. As the conversation progressed, we stopped paying attention to the movie and began making out on the couch. Shortly thereafter, I pulled him over so he was straddling my lap, and we began an intense and fun make-out session.

When things got heated, and we were down to our boxers, I took his hand and led him to my bedroom. The boxers came off and the real fun began. We both had fun exploring the other’s body. He certainly was no Adonis, but he had a tight body nonetheless. I was enjoying myself, and he seemed to be as well.

At one point, he asked if I wanted to attempt penetration, but added a big disclaimer about his complete lack of experience in that realm. He was skeptical it was actually going to happen, and because of his comment, I knew it wasn’t. If that was going to be his first time, it certainly would take more prep. Five seconds after my initial approach, our suspicions were correct. He apologized, as he did a lot in bed. He was embarrassed by his lack of experience, but I actually found the role of teacher satisfying. I wasn’t the first guy he slept with, but I also wasn’t at the end of a long list, that’s for sure.

I often think back to everything I learned from Broadway and how absolutely patient he was with me from the start. I always try to embody that when dealing with someone new to the gay world, both in the bedroom and out.

When we realized penetration wasn’t going to work, we moved back to foreplay. After we both finished, we cleaned up and laid next to each other talking. I wasn’t thrilled with this. I wanted to have sex, not a long dialogue about being a closeted gay. However, I’d never be so rude as to say that or scoot him out the door. He was fresh, and I needed to be gentle with the delicate situation. I was also trying to find someone I could call on regularly for sex instead of random new guys all the time, so I didn’t want to do anything to mess this up. We talked for a half hour before he realized how long we’d been chatting. We got dressed and went back out to the couch to watch TV.

He sat down and I laid my head in his lap. It felt very comfortable, and I certainly didn’t mind that. He pet my head while we talked and watched TV. Eventually I fell asleep in his lap until he woke me to tell me he was heading home. I apologized for dozing off on him, but he was actually quite delighted it happened. I walked him to the door and kissed him goodbye.

He was a really down-to-earth guy and a big sweetheart. I liked him, but not enough to want to date him. And, the whole still in the closet thing was not something I wanted in a relationship.

Going forward, I was still searching for my unicorn, but in the meantime, he would become my go to on those lonely horny nights…

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Unexpected Lovin’

All week long, I was still reeling from my date with Prince Charming. He was really everything I was looking for in a man. Mature, driven, sexy, interesting, masculine… the list goes on. However, I couldn’t limit myself to just him. I needed a distraction or I would end up driving him away. Pillow seemed to have fallen by the wayside. Not sure what went wrong there, but I wasn’t going to put any more effort into chasing him down. After coffee with the midtown trainer, I realized the potential we had for compatibility. He seemed like a really great guy. On top of that, he was texting me asking when we were going to finally go out again, which is always a good sign. Apparently I made a good first impression.

We agreed to go out for dinner that Wednesday. He chose an Italian restaurant, Il Melagrano in the neighborhood between his gym and apartment. When I arrived, he was already sitting at a cozy table at the back of the establishment. I apologized for being slightly tardy, and we got to it.

We chatted a bit about what we were going to order, and then turned the conversation to our days so far. He had a very busy morning, while I had a day mainly filled with surfing the internet. When that conversation got stale, I brought the conversation back to something we spoke about on our first “date” — His skydiving trip. He was very excited, and we joked about all the possibilities of things going wrong and what he could do about it. When age came up, I could see he was uncomfortable with how much younger I was — Seven years. I told him not to think about it and to judge me on my actions and words and not my years on the planet. We changed topics of conversation periodically from working out, to work attire, to the Tough Mudder, to Fire Island, his dog and so on…

When our meal arrived, we continued the conversation. I feel as if I was doing a lot of the talking because he finished his food much sooner than I. When I realized this, I started asking more questions and did less of the talking myself. The conversation flowed well over our single glasses of wine, but it wasn’t 100% fluid. At one point during the conversation he mentioned his studio apartment: “Well, you’ll see it some day when it’s not a complete mess.” It was nice to hear, because it showed promise of another date and signaled to me he was a gentleman.

After coffee and desert, I walked him home. The conversation on the walk was much more jovial and relaxed. I felt very at ease with him. When we got to his apartment, I was ready to say goodbye on the street, but he invited me in to his lobby. We started making out and things began to get heavy. He backed himself up against the wall and pulled me in closer. His hands were all over my body, including down my pants, and I was seconds away from him having my shirt completely off. At that point, he paused long enough to hit the elevator button, signaling an invitation upstairs.

From the look of him, he was tipsy off the one drink we had at dinner. I wasn’t expecting to move this fast, so I was a little caught off-guard. I liked this guy and debated if I should be doing this with him already, but I just went with the flow like I usually do. When we entered the apartment, I got to meet his dog. She was very cute and friendly. He put her in the bathroom so she wouldn’t bother us while we got busy.

Seconds after I sat on the couch, he ripped my shirt off. At least I knew he was attracted to my body. Him being a personal trainer, I was self-conscious about my body. His was nothing short of spectacular, so I was hoping I’d live up to his standards.

We moved things to the bed, and both of us had our pants around our ankles. We were doing some heavy petting and grinding. It was a good time, but once again, I was having second thoughts about this. After some more fooling around, he finished. I wasn’t able to join in the fun as my head was a bit distracted. And then, on top of that, I was worried he’d wonder if there was something wrong with me or if I wasn’t attracted to him. Neither was the case. It’s just something that has always been adversely affected by mental distraction.

While he went to clean up, I began to put my pants back on. He already established he was getting up around 5:00am to go for a run and had a 6:00am client. I knew he wouldn’t want me to linger for small-talk. He came back and sat next to me with the dog at our feet. She already took a shining to me after I gave her an extensive belly rub, but when he went to give me a kiss, she started making noise. At this point, he made a game of it and started testing her, scolding her between every kiss until she didn’t make a sound.

At that, I gathered my things and said goodbye with a kiss. I walked down to Port Authority to take the bus home. Normally, my MO. was to text immediately and tell him how much I enjoyed the date, but this time I waited to see if he texted me the next day to see if he was interested, especially since the night didn’t end exactly smoothly. Only time would tell…

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Prince Charming

Saturday morning, I woke up without an alarm and laid in my bed. I picked up my tablet and began checking my emails, Twitter, Facebook, and finally, my adam4adam.com profile. I received numerous messages, as usual, but mainly from old men and thugs. However, there was a message from one guy in particular. He started off by telling me I had a great body, which is always a plus in my book.

His messages had a certain sass about them. I really liked it. I can really appreciate a man who knows how to verbally spar. There was also some heavy flirting going on. He said, “Can you drop that towel?” I replied, “Haha. Do you know how many people have said that to me?” To which he responded, “Yeah, but do they also ask you to turn around and pick it right back up? I wanna see it all! 😉 “He pointed out we chatted before on Grindr. The conversation never went anywhere, but there was nothing that showed it to be a failure. We chatted earlier in the month about where we lived and where we went to the gym.

In one of my pictures on a4a, I am seated on my motorcycle. He was very turned on by this and told me he wanted to go for a ride sometime. Through the course of the conversation, I also learned he taught flight lessons at a nearby airport. I made a deal with him that he could ride on the back of my motorcycle if I got a ride in his airplane. I told him I would drive him to the hanger at the airport, and we could reenact some scenes from Top Gun.

He did one better than that. He offered to fly me to mid-state New York for lunch, with the possibility of handing over the controls. Learning to fly has always been on my life’s to-do list. I was thrilled! I assured him I wasn’t just attracted to him for his flying abilities. He suggested we go out for a drink sometime and suggested a biergarten in Jersey City. He told me to check it out online and let him know if it was my speed. When I told him I’d been many times, he was elated because many of his friends felt it was “too straight.” I explained to him how “straight” I was, and assured him the biergarten was not a problem. He added, “Even if no attraction you are someone I think I can hang out with ;)”

After chatting more, I realized I really liked this guy. He had great energy, and he was a complete gentleman. I was excited to meet him, so, although it was raining, I suggested we grab a drink that day. He had a lot he needed to do, but agreed to meet up later. He conveyed to me on a miserable day such as we were having, he would stay home and cook dinner. He offered to cook me dinner at his apartment, but suggested we grab the drink first to make sure we’re comfortable with each other. I happily agreed.

Later that evening, he picked me up in his car to go to the bar. We weren’t even a block before he turned to me and asked, “So do you feel comfortable with me?” I loved his honesty and candor. It was just my speed.

We arrived at one of my local bars, O’Nieal’s, and each ordered a beer. Over small talk, we both gulped our beers. It was obvious we were attracted to each other, and I thought he was a great guy. He was definitely worthy of making me dinner; especially after learning he also went to culinary school. Over beers, I also learned he is a flight attendant, but is only a few short months away from becoming a pilot for a major airline. I liked his sense of initiative and goals. It was a turn-on.

I paid the tab, and we drove to the liquor store to get beer and wine. On the way, he turned to me and said, “Just to be up-front and honest, I want to tell you I live with my ex-partner. Is that an issue for you?” I told him it wasn’t. If there was something going on there, I doubt he would have brought it up. Once again, his honesty and candor were rather refreshing. At the liquor store, he wouldn’t allow me to purchase anything. “You bought everything for dinner. The least you can do is let me buy the booze!” I insisted. He refused

When we arrived at his apartment, first, I was shocked by how close in proximity we were to my apartment, and second, his apartment was gorgeous. He slipped into something more comfortable and quickly gave me a tour while we talked about his job and his roommates.

We made our way to the kitchen to start on dinner. I love to cook, so I asked if there was anything I could do to help. He told me, “Just sit there and keep me company. I’m really enjoying having you here.” He told me the menu, and I was duly impressed. Fillet mignon, lobster tails, spinach and bacon, grilled onions and caesar salad with dressing made from scratch. I was really enjoying watching someone else who enjoyed themselves so thoroughly in the kitchen. I was happy we both shared a passion for food and cooking. I could watch him cook for hours. I was becoming more and more attracted to him by the second.

The conversation while he cooked was very special as well. I learned a few things about his previous relationship with his roommate and his feelings on monogamy. As I got to know him, I realized there are good gay men out there. He gave me hope. Just when I thought he couldn’t get any better, he walked towards me with a beckoning finger so he could give me a kiss. It was, to say the least, magical. He was a great kisser and the gesture was perfect. I was swooning. Already, this was the best date I’ve ever been on, and we weren’t even half way through it.

After going out to the grill to flip the steaks, he came back in and sat on my lap. We made out a little bit, and I truly learned how good and passionate a kisser he was. I didn’t want to stop.

When he finished making the meal, we took our plates and made our way into the living room to eat. Everything was DELICIOUS, including him. I couldn’t thank him enough. No man ever treated me this way before. It made me realize the potential of a real relationship with a man.

When we finished eating, we moved on to desert. We started making out on the couch and really began to enjoy ourselves. When we were down to our underwear, we took a quick break for him to ask me which position I was. When we discovered our compatibility, we made our way down the hall to his bedroom. He stripped off his briefs as we walked, so I followed suit. He was super sexy, and I was excited to be heading to his bed. I was really into this guy on so many levels.

That night, we had great sex! I was impressed with myself by how easily I made him climax. The chemistry was there both in the bedroom and out. I was head-over-heels for this guy with each passing minute. When we had our fill, we set an alarm for me and fell asleep spooning.

The next morning, when we woke, I was feeling particularly horny and frisky. I wanted to go for a second round, but I don’t think he was on the same page. After a short make-out session, he offered to make coffee and breakfast. He had already done enough. There was no way in hell I was allowing him to make me breakfast, but I would take a cup of coffee. After we cuddled on the couch a bit and he showed me some videos from his flight classes, he drove me home so I could get ready for work. Of course, I went to work late that day, and it was worth every second.

That day at work, we texted a bit. When the time came, I said goodbye and told him to be safe on his flight that evening. I couldn’t wait for his return and the possibility of seeing him again. I wasn’t completely sure where his head was, but it seemed like he was equally excited as I was at the prospect of a second date. This was just what I needed to help me forget about Pillow. Even if I never saw him again, I learned that the type of guy I am looking for really does exist out there. I was just hoping there were more like him our there. Either that, or I really hoped I finally wrangled my unicorn!

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Cloudy with a Chance of Depression

After the day on the lake with D, K, and D’s girlfriend, we all decided to go out for Mexican. It seemed this had become my new favorite cuisine considering I had it twice in the days prior on my date with Pillow and the Fire Island bartender. At dinner, I was scolded for being on Grindr. I really tried to limit my time spent on it when I was with friends, but it was a catch 22. If I spent time with them, I was not in a location where I could meet guys. We always went to straight bars. And, I was fine with this. In fact, I preferred it, but my friends would have to be tolerant of my Grindring.

I told D, “Just pretend I walked away from the group to talk to a guy when I’m on Grindr,” because that’s essentially what I’m doing. He suggested I physically walk away, but that was not something I was going to agree to. I asked him to be more understanding. I wish there is an easier way for me to meet men and still spend time with my heterosexual friends, but I have yet to find it.

After dinner and a quick pit-stop at a friend’s apartment to show face at his party, we made our way to the new Hoboken Biergarten. I wasn’t exactly in the most cheerful spirit. That morning, I never got a response from Pillow regarding his attendance to the lake. He didn’t take the time to text or call. I was starting to wonder if he just wasn’t into me. We had a great date the day before, and his texts following acknowledged that. But, I just had a feeling he wasn’t putting as much effort to get to know me as I was putting in to get to know him.

That night at the Biergarten, I noticed he was on Grindr. I’m not exactly sure why I sent him a message, considering he didn’t respond to my text messages, but I did. “Hey stud,” I sent. He responded, “Hi.” After not getting back to me at all, that’s all he had to say? So I said, “Did you go to Musikfest today?” His only response: “Yeah.” Well, that was over. So much for small talk. I said, “Well, have fun.”

After that, I figured I wouldn’t see him again. He obviously wasn’t interested, and it really started to get to me. I had been going on dates for a month and a half since breaking up with N. And, I went on A LOT of dates, almost all of which were failures. I thought this guy had a lot of potential, and I thought we were starting to click. I thought this was finally a success. He was part of an elite group — One of five guys with whom I’d gone on a second date with. Ever. I was feeling really low, and it showed.

A majority of the night, D looked my way and asked me why I was so gloomy. I told him I just wasn’t in a cheerful mood. He said, “I love this group, and I’m having a good time. Snap out of it. We’re having fun!”

I didn’t want to be a “Debbie Downer,” so I figured I’d step away from the table for a bit to try to clear my head. I had a hankering for a cigarette, so I went in search of someone from which I could bum one. I found a Good Samaritan who was willing to part with a cigarette. I relished every puff as a few raindrops fell on my skin. It was working it’s magic and relaxing me. I took the time to people watch. Everywhere I looked, I saw couples. Everything the cigarette gave me was just ripped from me, and I was back to feeling depressed. Dating was really starting to get to me. I’m a catch! Why couldn’t I find a good guy to realize that?

I went back to the table and tried to put on a happy face. I was successful for some time, but I was fading fast. I snuck away again to hunt for another cigarette. After I finished it, I walked home with two of my friends. I explained my issues to them both. They tried to console me, but I don’t think anything short of Bradley Cooper or Matthew McConaughey asking for marriage would have cheered me up.

When I got home, I poked around on Grindr. I found a guy who was two blocks away and looking for a good time. There was one issue — We are both tops. I told him we could just fool around and invited him over. He was an older man in his mid-thirties, but very attractive and had a great body!

We both undressed and had a good time. When we both had our fill, he began to get dressed. He expressed how much he enjoyed himself. He casually mentioned the possibility of a repeat, but we never exchanged numbers, so it would be completely left up to chance. Yet another casual encounter to add to my list.

This was the challenge I faced. I constantly wanted the instant gratification I knew I could conger up on-demand, but I also needed to stop destroying my emotional state following each of those casual encounters with men. It was a delicate balance, but I needed to figure it out so I would stop feeling so awful about my dating life…

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Fire Island Bartender

I always get particularly excited when a new guy pops up on Grindr who happens to live in Hoboken. I have pretty much blocked all the gay men in Hoboken, so when a new one pops up, I notice.

One in particular messaged me and was pretty cute. In his pictures, he looked like he had a good body and seemed very nice and genuine. After we chatted a few times, we exchanged numbers and switched things over to texting.

He told me he was a trainer at NYSC, but he was on hiatus while he got a certification. In the meantime, he was working as a bartender on Fire Island. He was gone almost every Thursday through Monday. This made it very hard to find a time to meet up, but eventually we figured it out.

We decided to meet on a Tuesday evening at a Mexican restaurant in Hoboken, Charritos. I had only ever heard good things but had never been. He made a good choice. He spent the day out in the burbs of New Jersey at his friend’s pool, and he was late getting back because of rain and flooding. When he finally showed up in his ripped jeans, finely quaffed hair, tight T-shirt and leather bracelets, I knew this date was doomed from the start.

The night before I was warned about this guy. While talking to N, I learned they knew each other in passing. N had seen him working at the gym and told me he was quite effeminate. I became skeptical but open-minded at that point, but when I met this guy in person, the second he opened his mouth I was turned off. On top of that, I noticed how filled out he was. He was supposed to be a trainer. I would never go to a trainer who was that pudgy and couldn’t follow their own advice.

We sat and had a very nice dinner. We talked about coming out and our families’ reactions to the news. We chatted about work and what we do for fun. The conversation was nice, but there was no spark. He just kept looking at me with this big smile like he wanted to gobble me up. I got the feeling he was a bit lost in the world. He was openly gay, but I’m not sure if he knew how to navigate life with men. I shouldn’t talk, because I have no idea what I’m doing, but he seemed like his GPS was slightly off.

After dinner, he asked if I wanted to grab another drink somewhere. I obliged, but I should have ended the date then and there. I knew better. I clearly wasn’t interested in this guy and had an out to go home, but I felt bad for him. I felt like he needed a friend, so I stuck around. We went around the corner to Sushi Lounge and sat at the bar. We each ordered a round and continued our conversation.

Somehow the topic of the rainbow came up as a symbol for gay culture came up in conversation. I explained just how much I despised the rainbow. He was flabbergasted. He didn’t know how to react. I explained it was not something I embraced. I could understand why some people need a symbol to hold on to, but I was making every attempt to not let my homosexuality separate me from the rest of the world. I am a normal ordinary man who happens to like the company of other men. I don’t need a rainbow to broadcast who I am. On top of that, I find the rainbow aesthetically unpleasing. I could tell I really turned him off by all this, but he wasn’t going to argue.

Then the conversation turned to previous relationships. I told him about the two I had been in and the duration of each. He told me I had a longer relationship than any he’s ever had. When I asked him why, he asked the bartender for another drink. He was a broken gay man. I felt bad for him, but certainly no attraction towards him. I thought maybe I could be his friend.

After we split our tab, I walked him home. Much to my surprise, he invited me up. I have NO idea why I agreed, but I did. We sat on the couch with some wine while we watched one of the music channels. We got into a conversation about Lady Gaga. I told him I found her very inspirational and really got behind her message and what she stood for. He told me he was over her. We obviously were going to but heads, so I was about ready to leave.

At that moment, he took my wine glass, took off my shirt, and started kissing me. He was an awful kisser. All over the place. I did not want to be there making out with him. I did however feel he needed to be kissed. So, I suppose you could call it a pity kiss. After a short while, I told him I needed to go home. I had work the next day, and it was getting late. I said goodnight, and with that I was gone.

I made it as far as the bottom step of his apartment stoop when I realized I left my umbrella in his apartment. There was no way in hell I was coming back to this place to get it, nor did I really want to see him again after that night. So, I rang his apartment. He buzzed me in, and I went back up to get my umbrella. When I walked in the door, he pushed me back into a chair and mounted me. Apparently he wasn’t done. I immediately told him I needed to go. I only came back for the umbrella, not an encore. That’s when I really realized he only wanted me for my body. We didn’t have that great of conversation all night and disagreed a lot. We were obviously not compatible for a relationship, but maybe he was just horny. I was slightly offended and made my way home.

He immediately texted me: “Had a great night with you.” I didn’t respond immediately, but in the morning I texted: “I had a good time too.” After that, I was done with him. I was pleasant, but I didn’t give him hopes of a second date. He would not be a repeat offender. The next day he texted, “How was your day at work?” But, he would not get anything back from me. Once again, it was back to the dating pool…

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Weekend Hookups

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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2 Gay MadMen

Out of the entire roster I built before I went away, I had the highest hopes for one in particular. His picture on Grindr was of his face. What a nice change from the torsos that scattered my screen. And, not just any face. This man was sexy. He had dreamy eyes and perfect lips. I couldn’t wait to meet this man in person.

When we first started chatting on Grindr, I favorited him. I noticed one night he was very far away and asked where he traveled to. I learned he lives in my old neck of the woods in Pa. He explained he lived out there, worked in the city, and one or two nights a week, he would buy a hotel room so he didn’t have to commute. I suggested we grab a drink sometime. “Def man. I’m game for that,” he responded. And with that he gave me his phone number.

We were unable to set up a time for drinks before I went on vacation. He was polite enough to hit me up while down there to see how I was doing. One night, while texting each other, he decided to pick up the phone and call me. I couldn’t answer because I was riding in the car with my family, but he left a very sweet message. He gained a lot of points in my book for calling that night! It meant a lot to me.

When I returned to Hoboken, we finally set up a night to grab a small bite and drinks together. I already liked his style. He suggested tapas because if the date didn’t go well, we weren’t stuck together He booked a hotel room for Wednesday night, and I picked a restaurant. He was my fifth date in four days.

The night of our date, he was running late. He apologized and explained this was standard protocol for him. I told him not to worry about it because I was usually the one running late. To kill time while I waited for him, I strolled through Eatily. When the time for out date was approaching, I walked to the restaurant to get us a table. When I arrived at Boqueria in the Flatiron District, there were about fifteen people standing in the rain waiting to go inside. I didn’t panic. I tried the backup restaurant, Sala 19, but they had a 45 minute to hour wait. I called (Let’s call him “Pillow” since his lips looked like two little pillows I couldn’t wait to smooch), and told him of the predicament. I also explained I would be trying to find a new place and would meet him on the street corner. I did some research and found two other places. The first couldn’t seat us for another two hours. The second, Aldea, had no wait. We met and shook hands, I suggested we go there since it was two blocks away. He agreed.

When we arrived at the restaurant, I almost suggested we leave. It had awful ambiance, and NO ONE was there. It already made the date feel awkward. They sat us upstairs, and we both ordered drinks. When my sangria arrived, it was clear, served in a Tom Collins glass and topped only with green grapes. I don’t think it was sangria, but it was good, so I drank it. We both struggled to find anything on the menu we liked. I am NOT a picky eater, but this menu was a challenge! I suggested we just leave after the first drink and find a bar. He said we should stay and we ordered the almonds and olives plate, as well as a shrimp appetizer. We talked about the possibility of hitting up a bar after dinner as well.

The conversation started off dry and forced. This date I had such high hopes for started off on the wrong foot. I didn’t know how to rescue it. I never realized how much the setting could ruin a date, however, we were able to find some common ground. We both worked in advertising. I was happy I never asked him about it before, since it gave us something to talk about to break the tension.

When we finished, they brought us chocolates, we paid and went back out into the rain. We started walking up Broadway towards my office and somewhat towards the hotel he was staying at. As we passed the Ace Hotel, I stopped him and asked if he still wanted to get another drink or did he need to get back to his hotel. I was giving him an out. He said he’d be down for another drink, so I suggest the Breslin at the Ace Hotel. I had been there many times and really enjoyed the vibe there. I was also glad he wanted to continue hanging out with me.

There were no seats available at the bar, so we found a nice plot of space in the corner to lean against the wall. Once we had our drinks, things got a lot more relaxed. I said, “We should have just come straight here. That place was awful!” He told me I shouldn’t worry about it. We stood there for another round. With every drink, the mood got lighter, and I became more attracted to him. After the second round, he asked if I minded if he have a cigarette. I said, “Only if you don’t mind giving me one.” We stepped out into the rain and found a doorway to huddle in to smoke. We talked some more and the body language was very positive. I debated if I should have kissed him right then and there. But I didn’t of course.

We went back inside and managed to find two stools. We sat facing each other and he began to lean in much more when we spoke. His body language was becoming more and more provocative with each sip. After that round, we both had another cigarette. When we returned this time, the only space available was at the bar. I ordered us another round of drinks and an order of fries considering we basically had olives for dinner.

I was having a good time with him. He was charming, had a good job, family oriented, very good-looking, mature, etc. It was about time I finally had a good date. The whole date, all I could think about was how much I wanted to kiss him. Around 11:30pm, we finished our drinks and closed out the tab. We spent the last four hours together. I wasn’t sure we’d make it past the first forty minutes when we stepped into the first restaurant.

I told him I would walk him to his hotel since it wasn’t far from my office, and I had to return there to get my things. When we got to the front of the hotel, I expressed to him how much I enjoyed the night first verbally, and then physically. I leaned in for a kiss and got exactly what I was hoping for all night. I pulled back and said, “And a good kisser too. It’s a shame I waited til the end of the date for that!” With that, we started kissing and embracing more while the doorman stood watching us. Finally, we both pulled back. As I started to walk away, I turned back and said, “We do this again? Soon!?” He nodded in agreement.

I walked away with the biggest smile on my face. What started out bad, ended really well. I couldn’t have been happier. On my way home, I texted him telling him: “I had a great time with you tonight!” He responded, “More to be had. I had a great time and now that we met, I can loosen up a bit.” Then we got into the conversation of the compatibility of our astrological signs. Then he said, “Yea. I wanted to bring you up, but it’s a first date. I try to be reserved. LOL Did I want to? No. But, I was good.”

I was thrilled. This meant he was really attracted to me and wanted to start something real, not just a hookup. I didn’t want to get ahead of myself, nor did I want to put all my eggs in one basket, so I didn’t toss the roster out just yet. But, I certainly had a front-runner.

That weekend, I texted him a few times, but got no response. I wasn’t thrilled with that sign. I questioned if it was just the alcohol talking after our first date, but I didn’t panic. I would see if we could meet during the week again when Monday rolled around…

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Harvard Law’s Review

After meeting the police officer and the southern gentleman, I was on a roll. I was getting through my roster of men with ease. Monday was no different — I scheduled in a new one, “Harvard.”

I picked him up on Grindr one late night in the city. He was a very attractive lawyer who seemed pretty normal and very masculine. He went to the gym a lot, so his body was tight, and he seemed like a genuinely nice guy. We exchanged numbers shortly after we began talking on Grindr. I texted him a few times while on vacation with my family to make sure he was still thinking about me periodically while I was gone. He was another guy I thought had a lot of promise.

The night before, while waiting for the bus to meet the southern gent, I called Harvard. He picked up, and we chatted a bit. I told him about my vacation and he told me how similar his family is. He had a trip coming up in a few months and felt the same way about it that I did about mine. It was easy to talk to him. He sounded great too. No flamboyance at least. I was looking forward to meeting him in person. I thought to myself, “Maybe a phone call should be a new part of the screening process before the first date. I could eliminate a few bad apples this way.”

On the walk home from my date with the souther gent, we texted each other. He managed to slip in a comment about how much he liked my body. I certainly appreciated the compliment and threw one right back in his direction.

We scheduled a date that Monday evening at Blockheads, and outdoor Mexican restaurant. This would be my third date in two days — I was speed dating over the course of a few days. I arrived early, so I put our name down and sat to read Chelsea Handler’s My Horizontal Life until he arrived. (She’s part of what inspired me to write this blog, so I thought I should at least read her books).

When he arrived, we were seated immediately. We had a nice table for two on the rim of the crowd. A few birds flew around our feet, and he started to freak out. I get weirded out when pigeons do it, but these were tiny little birds, not the flying rats I want to punt every time I see them. Now, I’m not judging, but it was a bit excessive. He freaked out and told me how much birds skeeve him out, but I was still a little weirded out by how much it bothered him.

I started to size him up. He looked like his pictures and he filled out his polo very nicely. Great arms and a great chest. I could tell he was a regular athlete who hit up the gym. This is important to me since I am so active. I need someone who can keep up with me.

We started on the small talk. We chatted about college, family, vacation, where we grew up, what we did for fun. It was almost as if he was reading from an interview script. The conversation was alright, but it certainly wasn’t relaxed. I was a little turned off because everything he said had a slight air of superiority to it. He was trying too hard to impress me, and if there’s one thing that turns me off with people, it’s that. He even wore his pretentious college ring. He was a nice guy, but I couldn’t take the high brow attitude.

In between all this, the waiter came by to take our drink orders and then our dinner orders. Every time he came by, Harvard started flirting with him. It was obvious this guy was a ‘mo, but he wasn’t even attractive. The waiter is supposed to flirt with you for a good tip, not the other way around.

We both enjoyed our meal and continued the “interview” while we ate. He told me about his “type.” I fit the mold perfectly as far as physical looks went, but I have a feeling he was looking for a younger or more subservient guy. We would butt heads, and I think he was looking for a guy he could rule over.

When the date ended, we hugged goodbye. We didn’t even talk about follow-up. We both knew there were no fireworks there. On my walk home, I texted him, “It was nice to meet you.” He responded, “likewise.” After that, it was simply on to the next guy on the list…

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A Southern Gentleman

Before I went to OCMD, I was talking to a southern gentleman who found me on Grindr. We hit it off immediately. He seemed like a level-headed guy, and he was 35. After my last failed relationship with a 25 year-old, I decided older was better. San Francisco opened me up to the idea of dating a man of that age, and I had a good feeling about it.

The Southern Gent and I messaged each other a lot on Grindr. We also exchanged pictures. He found me exceptionally sexy, and I found him to be quite attractive. He was no super model, but he certainly took care of himself. We exchanged Facebook information. I looked through all his pictures. They were of him being crazy at a wedding, boating on a lake, safari hunting in Africa, etc. The guy had a picture of a Zebra he took down. I was impressed and swooning a bit.

We tried to figure out a good time to meet, but it always conflicted with his schedule or mine. After a while, he went completely dark. We made plans to meet one Sunday night, but when that weekend came, I got no response to the many text messages and phone calls I made. “I can only assume you lost interest already… Not sure if I did something, but I’ve sent you msgs with no response. Was excited to meet you… If I’m wrong, you know how to reach me.”

An entire week went by, and I heard no word from him. I removed him from my favorites on Grindr so I wouldn’t have to look at him every time I pulled it up. Of course, that’s when he started to message me again. He apologize emphatically for not getting back to me and blamed most of it on getting a new job. I’m definitely one for giving second chances, and I though he would be a great match for me, so I agreed to meet him when I got back from my vacation.

While in Maryland, we texted periodically. We set up a date for the Sunday evening upon my return home. He picked Pier I Cafe on the Upper West Side. I took the bus into the city and hopped in a cab the rest of the way. I made my way down to the Hudson waterfront and saw him immediately. He had a very New England country club look about him. I liked it. He didn’t look like a snob, but he looked like he appreciated the finer things in life.

We both grabbed beers and tried to find somewhere to plop down. There were no tables available, so we found a cement wall to sit on. We got to know each other slowly. We talked about our jobs, our living situations, working out, college, etc. The conversation was flowing quite easily. He is an architect, which is something that has always interested me. I found it sexy. The one hangup I had with him was he turned into a total queen every time he laughed. He was a bit flamboyant. He could have sucked all the air out of the room after every laugh had we been indoors. It was extremely off-putting. I’m sure you’re all judging me as picky at this point, but it was hard to look past. I was starting to get annoyed with these guys who claimed to be masculine. It’s my one real hangup in the gay dating world, and guys self-judge this aspect of their lives VERY poorly. Basically, I’m attracted to dudes who just so happen to be attracted to other dudes as well, not some big ‘mo.

I also started to gauge the level of chemistry between us. It wasn’t exactly at its peak either. We shared a lot in common, but I could tell the attraction wasn’t there on both sides. We both passionately talked about cooking and our specialties. It was an interesting conversation. After a while, I noticed one of my friends. He also noticed me, so on one of his trips to the bar, he swung by to say hi. I introduced him to the Southern Gent and talked to him about how things were going since his marriage in Key West.

Four rounds and one basket of calamari later, it was time to go home. I gave him a small kiss on the lips and said, “We should do this again sometime.” I didn’t have such a good feeling about our chemistry as I did before the date. I was a little disappointed, but I thought maybe I needed to give him a second chance. I would leave that up to him. If he was interested, he would followup the date with a phone call. When the call never came, I knew my suspicions were accurate. I unfriended him on Facebook so I could write about my dates without feeling guilty.

I was disappointed it didn’t work out, but that was based on an assumption I made before I even met him. I would need to not get my hopes up so high before the first date. It would be the downfall of my morale if I let the bad dates and disappointment get to me…

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Whoring It Up in OCMD Pt. 2

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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