Posts Tagged adam4adam.com
Visit From the Closet
Posted by One Gay at a Time in Gay Dating on September 19, 2011
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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Posted by One Gay at a Time in Gay Dating on September 13, 2011
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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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 22, 2011
I first downloaded Grindr as I was pushing back from the gate on my flight to San Francisco for business. Upon my return, I often played around with it at work. Early in my Grindr experience, I found a VERY sexy torso to strike up a chat with. The guy seemed very level-headed and not simply interested in hooking up. I also discovered he worked across the street from me.
But, when I asked him to hang out, he got very shy. He told me he was very picky and wasn’t that interested in meeting someone. I asked if he would grab a drink after work sometime, and he kinda let me down easy. Periodically, I messaged him after that just to say hi, but I never got much of a response. It was disappointing. Finally, I gave up.
Then one day, out of the blue, he messaged me. He asked if I had just been in Bryant Park sitting on a park bench for lunch. I was impressed and thrilled he recognized me without having met me. Ironically enough, I was on a lunch date with someone from adam4adam.com.
We chatted about the chances of him picking me out of a crowd in the city. I brought up the idea of getting a drink together. A month passed by since the last time I asked him. This time he was ready to play ball, maybe since he saw me in person? Not exactly sure. Either way, I convinced him to send me both his number and a picture of his face. At this point, I’ve had so many guys’ numbers in my phone, I needed some way to keep them straight (the first sign I was becoming a whore). My strategy was to get pictures of them to attach to their contact profile. I’m much better with faces than names.
A week later, on a whim, I sent him a text asking if he would be interested in grabbing lunch that very afternoon. I knew it was a long shot since it was such short notice, but why the hell not. Much to my surprise, he agreed. I had to run into a meeting, but would be able to meet immediately following since my work for the day was pretty much over. I told him to pick a spot. He told me he’d get right on it.
We met in the square between our offices and walked to KyoChon for some excellent wings. I had never been there before, so he explained all the ins and outs to the place. We took our food and grabbed a table upstairs.
He was great company. The conversation started immediately when I met him. The whole walk over we chatted about careers and how we got where we are today. The conversation still flowed while we ate. There were no awkward pauses or hiccups. I was very comfortable with him. He also had a great smile, something I’m coming to find is a weak spot for me. Ironically enough, he looked like Boston, had the same name as him, and he recently moved to NYC from Boston. The resemblance was a little uncanny, but I moved past it quickly.
I had a lot of respect for him. He left a very successful job at a law firm to come to NYC to find himself. He wanted a new job, but didn’t know what he wanted to do. He just knew he wasn’t going to find himself in Boston. Right now he was working in marketing, but that also wasn’t exactly what he wanted to be doing. He was still on the path to clarity.
We also talked about therapy. He was seeing a psychologist from time to time to talk through issues. He told me most people don’t realize it’s covered by most insurance companies to go for periodic sessions. He explained how it’s been a good outlet for him to get his head straight. I didn’t see him as a crazy person. I actually saw him as more sane for having such a healthy respect for it. I began to entertain the idea myself. My friends are my therapist. I have abused many of my friends in this respect and turned to writing a blog to alleviate some of that burden. Maybe a therapist was what I needed.
This was truly a quality guy. A guy I really wanted to get to know. I knew I would need to take it slow with this one. I didn’t want to come on too strong and turn him off right off the bat. We walked back towards our offices and said goodbye with a nice handshake. He turned and said, “This was good. We should definitely do it again!” I was very happy. I passed the test. Also, was this a successful “date?” It didn’t quite feel like it was a date going in, but maybe it was a lunch date by the time we were done. I was looking forward to our next.
As time passed, I didn’t push the issue of a second “date.” I also became distracted with other guys, but one day, while going through my contacts, I discovered him again. I shot him a text asking if he’d want to grab lunch again soon. He told me he was out-of-town for the week, but we would touch base when he got back the following week. Only time would tell if we’d figure it out…
Follow @onegayatatimeDr. Talks A Lot
Posted by One Gay at a Time in Gay Dating on August 4, 2011
Since I was back to the single life, I was back to adam4adam. This certainly didn’t thrill me. But, once again, I have almost no gay friends, and I’m really not big on the gay scene. Other than online, I had no way to meet other gay men. One year out of the closet, and only one friend tried to connect me with another man.
In my a4a travels, I came across The Hot Dermatologist. When I first set eyes on his picture, I was a bit gaga. His body looked amazing. I messaged him and told him so, but I also told him I’d like to get to know him better. He responded well because I wasn’t just looking for a hookup. After chatting back n forth a few times, we agreed to meet for dinner.
We set a date, and made plans. He lives on the Upper East Side of NYC, and he asked if I would be willing to trek up there. I had no reason why I couldn’t, so I agreed. The day of the date, we picked a time, however, I finished work earlier than expected. I texted him, and we changed our plans. He meant to walk the dog before we met, but since I was done early, he invited me to join him for the walk.
When I arrived at his apartment, he told me to come up. He was doing something and wasn’t quite ready yet. When I got up to his apartment, we introduced ourselves at the door with a handshake. He told me to come in and introduced me to his dachshund. He apologized for not being ready and told me he was uploading pictures from his camera onto his computer. I originally thought it was something for work, but then he started showing me the pictures. They were of his dog from the weekend. This was a priority over a date with a sexy man?
He then proceeded to tell me he endorses a product on the HSN. He showed me the video clip from his call in earlier in the day.
Finally, he was ready to take the dog for a walk. We made our way outside and began to chat a bit. We talked about work, his dog and what we do for fun — simple small talk. He warned me ahead of time he needed to stop at one point to call into HSN live again. We found a quiet corner of the street, and he placed the call. It was interesting to hear what he had to say, but at the same time, I felt this was a bit odd.
When he finished the call, we walked back to the apartment to drop off the dog. He informed me his best friend was coming by while we were grabbing dinner to watch the dog and then go to the gym together later.
We walked to a nearby Mexican restaurant. He made a few recommendations, and we ordered. The whole meal, he talked. I got a few words in edgewise, but the majority of them were simply a response to his comments. He talked about how he’d like to meet a guy, but they never seem to tolerate his busy schedule. He had a boyfriend for a long time who was able to deal with his lack of presence, but that was long over. In the next sentence, he talked about how little he was making because he was in residency. He was interviewing at two different dermatologists’ offices for a position on Saturday and Sunday, his only two days off. How did he expect to find a man willing to be in on that deal?
Following dinner, he decided to take me into the garage of his building to move his car to the new space he acquired that morning. Again, this was an odd thing to do on a date. It was like I was tagging along for his errands. As we took the elevator to his floor, he told me his friends do not approve of his online dating. Just before opening his apartment door, he explained to me how he told his friend he was on a business dinner. I didn’t know what to do with that information. I had no idea what part I was supposed to be playing.
We walked in and I was introduced to his friend. His friend said, “I thought you told me you were on a business dinner?” Dr. Hotness responded, “I did.” To which his friend responded, “You went dressed like that?!” I think he immediately caught on to what was up and stopped asking questions.
After the good doctor showed his friend the pictures of his dog and the same video he showed me only an hour earlier, we all went down to the sidewalk in front of his building with the dog again. We all sat there chatting a bit. This was one of the oddest dates I have ever been on. I didn’t know what to do. I didn’t want to run, but I didn’t want to sit there any longer either. It was the single most selfish dateI’ve ever been on.
When 8:00 arrived, Dr. Hotness said, “Well, we’re gonna hit up the gym.” We all stood, and I got a handshake. “Call me later,” he said.
With that, I turned and started walking downtown. I knew I couldn’t walk all the way down to Port Authority from 96th street, but I wasn’t ready to hop on a subway. I pulled up Grindr to see if any of the other men I was pursuing were available to meet up. Of course no one was. I wasn’t ready to just go home and plop on the couch, so I called a few friends to see if anyone was interested in an evening jog. Once again, no luck.
I got about half way to Port Authority when I gave in and flagged a cab. Another date under my belt and I had nothing to show for it. It was very disappointing.
That night, I sent him a text: “It was a pleasure meeting you and [the dog].” He responded, “U too.” I have NO idea why I said this (probably because he was so hot), but I did: “Hit me up if you want to meet up again sometime.”
In a funny twist of fate, he responded, “I think we should just be friends.” I texted, “Gonna have to agree with you there. Not that you’re not a good-looking guy. Haha.” Apparently I struck a chord there, because he said, “Ha. Why? Am I not your type?” I said, “Haha. Why do you ask? You actually are… You just don’t seem to be fully invested in finding a relationship to be honest… I assume you said just friends because I’m not yours?”
At this point, he was insulted by my observation. We went back n forth on the issue. I told him I didn’t mean to offend. After some long exchanges and some playful banter, we ended on being friends with benefits. He said, “I can tell you are a great guy too. Love your body and how sincere you are!” I was very flattered. Since then, we have been texting but have yet to meet up again. Who knows? Maybe we’ll have a hot time sometime. Maybe not.
I went in to this date very skeptical. Most men and women would swoon over dating a doctor. For me, it was a BIG turnoff. I already dated a Broadway dancer who was unavailable. A doctor would be a step in the wrong direction. When was I finally going to find a guy for me? It was back to the drawing board…
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Posted by One Gay at a Time in Gay Dating on June 24, 2011
At this point in my dating life, online dating site, adam4adam.com and phone app, Grindr have produced fairly decent results. Sure, a lot of them were flakes, but the ones who made it to a first dates were all fairly decent guys.
One day, I messaged North Carolina to ask him how Grindr was working out for him. He told me about a few dates he went on. In turn, he asked if I had any positive dates from the app, and I told him about my encounters. He then asked if I had spoken to a particular guy, one of his coworkers, who happened to live in Hoboken. I checked my list, and in fact, I had been chatting with him for some time.
I took the opportunity to message the individual and tell him I knew one of his coworkers. He wasn’t too happy. He’s not “out” and was annoyed North Carolina was talking about his sexuality to other people he’d never met. When I explained he did it to set us up, things calmed down a bit.
We began chatting more and came to find we were neighbors. But, not just neighbors in the same hood. He lived across the street.
We attempted to find time to grab a drink, but he was always at the gym or I was in the pool. It never seemed to work out. Finally, on a random Friday, I texted him late in the evening while making dinner with my sister to see if he had plans. He was entertaining the idea of going into the city to meet a guy at Boxers. But, when I suggested we grab a drink locally, he was all over it.
He waited for me outside my building, and we walked a few blocks to a local bar. We both ragged on each other for taking long to get ready. He also took the opportunity to poke fun at my flip flops, all the while wearing men’s U.G.G.s. Who even knew they made U.G.G.s for men?!

We grabbed a high top near the bar and drank vodka sodas and Guinness all night. I learned how new he was to the gay world. We were both very fresh, and we swapped coming out stories. There wasn’t a single moment during the date that felt uncomfortable. He was perfect. Not only that, he had a smile that could melt granite. His dimples made me swoon, and his eyes when he smiled made me giddy.
We talked about Grindr and the guys we knew in common. He informed me others asked him about me. This was intriguing and surprising to me. First off, it’s an ego boost, but secondly, why would a guy talk to dudes about other Grindr dudes? Isn’t that your competition?
The time came for us to close our tabs and go home. He was ecstatic because his tab was so low. He thought it was beacuse he had a temporary debit card and the bartender made a mistake, but in reality, the other drinks were on my tab. I allowed him enjoy thinking he made out.
When we got back to my place, I asked if he wanted to come upstairs. He hesitated for half a second, but accepted the offer nonetheless.
Once we got upstairs, we started making out on the couch. He said, “I’ve wanted to do that all night!”
I proclaimed, “Me too!” Things started to heat up, and our hands were exploring each other’s bodies. He suggested we move to my bedroom, but my roommate was still awake with her light on in her room right next to mine. After a short period, I noticed the light was out and was confident she was asleep, so we moved things to the bedroom. We fooled around and finally dozed off.

The next morning, I awoke especially horny. I woke him up by arousing him, until we were both fully enjoying ourselves. At one point, I was grinding against his backside when he suggested I get a condom. I obliged and we began to have sex. I could tell he wasn’t used to this, and it was short lived. This is the one big regret I have from our encounter. I think he found himself in a situation that pushed the boundaries of his comfort zone, and he gave into the moment. While he “asked for it,” I feel we took things too fast too early. I really liked him! A lot! I wanted to do things right by him.
After we showered, he got dressed and went home. I thought about him a majority of the next day. I had other prospects in the queue, but this one had boyfriend potential. So, I took what I learned from my relationship with Broadway, and I applied it to the current situation. I wasn’t going to rush things, and I wasn’t going to try to define or label it either. I would patiently await whatever was going to happen next.
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Posted by One Gay at a Time in Gay Dating on June 21, 2011
Now that I have a fair amount of dates under my belt, I feel comfortable meeting more men without much prescreening. Normally, I try to qualify them by talking a fair amount before meeting in person. Now, it’s worth it to save this conversation for a first date.
I came across a very attractive 25 y.o. on adam4adam.com. His profile was far from substantial. Play safe only. HIV neg and STD free — looking for same. His name also had nsa (no strings attached) in it. This is not the arrangement I seek out, but at this point, I was having fun and not asking too many questions.
We exchanged a few messages over a decent time span. The conversation actually died to the point I messaged, “Hey there. Haven’t heard from you for some time. If I’m barking up the wrong tree, let me know.”
He responded with continued interest, and shortly after, I said, “I hope I’m not being too forward, but I’d love to meet up for a drink sometime. Toss me your number if you’re interested.” I got his number and set a date. We agreed to pick a location the following day as the workday was ending.
I texted him the day of the date to make sure we were still on. Nearly an hour passed. Just when I had about given up on him as yet another flake, he responded. He told me to meet him at 7:00. I purposely left my office late to arrive fashionably late. That would have gone well, except he showed up for the date a half hour late.
I waited for him at a high top in the dive bar he chose, Whiskey River. When he arrived, he apologized for being late and grabbed a beer at the bar. The conversation started slow, but picked up quickly once we got comfortable. I asked him why he agreed to go on a date with me. He said, “Because you asked me out for a drink. It was a nice change from all the guys looking for hookups.” When I asked him what he did, he told me he was unemployed and unleashed a story like I’ve never heard before.
He was born in Israel. After he served his military term for one year, he decided he wanted to explore the U.S. for 6 months. He left behind a boyfriend of about a year (a very complicated relationship). He ended up staying in NY working as a waiter. When a woman heavily flirted with him, he informed her he was gay. She introduced him to her other gay friend, and they all became close. So close, he and the woman married (took me a few minutes to realize for immigration purposes). This woman had fallen in love with him, but he realized this too late. They had a big falling out, and he moved out on his own.
That’s when he met a new man. They were dating for about a month when this man decided to take him to his Connecticut house. My date was expecting to be visiting a cottage, when in reality it was a mansion. This man was a millionaire 10 years his senior.
The whole time my date was telling me this story, he looked past me. His eye contact was unnerving. He periodically glanced back to me, but spent a majority of the date looking elsewhere.
So Wandering Eyes went on to tell me this man asked him to move to California with him for the winter. This was his typical schedule, and he wanted Wandering Eyes to come. W.E. left his job managing a hotel and his friends and moved to California.
He lived the life of a kept man. They even discussed marriage. He drove a Porsche, wore Armani suits, was waited on hand and foot by servants and went to galas, award shows and benefits, all the while not working. The millionaire was also very possessive over him. He read his emails and checked his phone periodically. W.E. had nothing to hide, so he allowed this behavior. He started to get bored with his new lifestyle and missed his NY friends,. He decided to plan a trip back east for a week.
Upon his return, the millionaire was acting very different and suspicious. When the opportunity for W.E. to read through the millionaire’s emails arose, he jumped on it. He discovered that while he was in NY, the millionaire had an affair with another man and even took pictures of the two of them in the bed he shared with W.E.
W.E. decided he wanted nothing to do with this situation moved back to New York. The millionaire did everything in his power to get him to stay, even asking for them both to have action on the side, and they would just stay together. No dice. W.E. was gone.
In the meantime, the woman he married was interested in marrying a new man and filed for divorce. W.E. came back to New York jobless, divorced, newly single and homeless (the millionaire allowed him to live in his Manhattan apt until he got back on his feet). I wanted to walk around the table and give him the biggest hug. My heart bled for him.
I learned so much about him from that story. His character ran deep. His friends told him he was crazy for giving up the lifestyle he had, but he was still able to recognize his own unhappiness and moved on.
We chatted for about 3 hours before we walked to a Starbucks for a coffee. There we talked about movies and one of his interests, comic book heroes. We discussed our favorites and why.
The time came for me to go home, so I walked him to his subway stop. He had the most beautiful eyes and lips. I had been staring at them all night. A majority of the night, all I could think about was how much I wanted to kiss them. However, when the time came, I lost my nerve. I hoped he would make a move, but he didn’t. We hugged goodbye and talked about a second date.
On my way home, I texted, “Hey. Prob supposed to wait til tomorrow to msg you, but not my style… Really enjoyed meeting you tonight. Can tell deep down you’re a really great guy… And you’re even hotter in person… I’d really love to see you again some time if you feel the same… P.S. I’m really awkward with goodbyes… Sorry… Felt like such a sh*t when I walked away…”
He responded, “No worries. I probably would’ve kissed you if you didn’t walk away… So maybe it’s not a bad thing that you did…”
This is very confusing. How would it be a good things I walked away without a kiss? “Of course it’s a bad thing! Wanted nothing more than for you to kiss me ;),” was my response.
His next text was much more reassuring; “Well… Guess we’ll know better next time.”
I told him I was happy to hear there would be a next time. Sadly, there never would be. We tried, but plans never seemed to work out. Things fizzled out, and we haven’t been in touch since…
Follow @onegayatatimeGay Terminology
Posted by One Gay at a Time in Gay Dating on June 20, 2011
When I was single and “straight,” I used to think about how gay men would react to me when I came out. I kinda always knew I’d be a catch. Now, it’s a little out of control. I have been propositioned by sooo many men on Grindr and adam4adam.com. I’m not tooting my own horn here. I recognize the quality of men admiring me. And, quantity does not make up for the lack of quality.
Many of the messages I receive are easily understood, such as:

Would you let a dude lick ur feet for cash? $200 U come in, we watch porn, I lick and massage ur feet. I jack off… U sit back and relax. No other touching… and also…
Wanna come over and breed me?… A bunch of guys are gonna take turns with me. Want in?… (After some time passed with no response from me) Guy who was gonna host can’t anymore. Wanna breed me?
Some take it even further to illustrate their point.
Let me show you what’s gonna happen… (Picture of his massive black dick) U gonna need stitches!
Some of the messages and profiles I see are not so easily deciphered. Things like, looking for? Looking for what? Does this mean what am I into? Are you asking me if I’m looking for a hookup or a relationship? Just ask the question you want an answer to. I’m already in the dark about so much in the gay culture. Code and cryptic messages aren’t helping!
This is where you come in. I’m enlisting the help of everyone who reads my blog/tweets to compile a gay dictionary. I’m new to this game, so things like “M4M” confuse me. I know it means man for man, but when you’re on a gay app, why would you feel the need to say that? Did you mean something else? Obviously, I need someone to help me decode the lingo.

What’s a power-bottom, and how is it different from a regular bottom? I’m so lost!
I tried doing my own research for many of the terms I’ve come across, but this was an overwhelming task.
So I’m asking you to think about the gay terms you see or use and define them in the comments for me. Thanks!
Follow @onegayatatimeThe Repeat Offender
Posted by One Gay at a Time in Gay Dating on June 17, 2011
It’s amazing what the power of suggestion can do to you. All it takes is for someone to put an idea in your head, and you are rendered incapacitated. It can consume you and become all you think about. This power was wielded over me by who other than the 40 y.o.
Following my birthday weekend, I reserved Sunday night to sit my single ass on the couch and catch up on the DVR. I was all but finished watching everything I taped the week before when I got a a text message from the 40 y.o. “Recover from your birthday present? Want another bj?”

That’s all it took. The seed was planted. My mind raced back to the last time he came by, and all I could think about was how good it felt. I told him to come by my apartment. When he asked if I could come to his place, I became a little uneasy. I wasn’t sure about not being on my home turf. He wanted to host because he was doing laundry and packing for a business trip the next day and he “figured I’d take a break to blow you. lol.”
I explained to him I felt more comfortable in my own setting. To which he responded, “Understand. It’ll just have to be a raincheck then. I’ll be back in a few days.”
That’s where he had me. I lost the upper hand, and he knew it. I would either have to come to him, or I would have to wait for the blowjob that was just planted into my brain.
I tried my hand at being clever to lure him to my apartment. “Put a load in… Then I’ll put a load in, and you’ll be back just in time to switch it over. You know you want to.”
My tricks didn’t work. “I have to be smart. I have to be up for an early train. Guess I’ll have to watch porn and spank it.”
We sparred back-and-forth with our words, both trying to convince the other to come to them. Just when I had him convinced to make the 7 block trek to my apartment, one of my roommates came home. I was so close, and yet so far away. With that, I finally agreed to go to his place. He lives in the same building as one of my friends, and I needed to drop something off at her apartment.

When I arrived, he gave me a hug. He proceeded to show me around his apartment, the whole time playing with himself in his gym shorts. Finally he pulled me into his bedroom and sat me down on the bed. He pulled my shorts down just enough so he could get working on me. I took his shirt off and began to play with his nipples. We were both enjoying ourselves. He pulled off his shorts and sat naked on the hardwood. His member was BIG just as I remembered from the first time, however, he never got fully erect. I remembered this from our first encounter and how worried I was it would happen to me at the age of 40.
Then he did something that both shocked and disgusted me. He pulled out a small bottle, untwisted the cap, held it to his nose and heavily snorted in each nostril. I don’t have a lot of experience with drugs, so I wasn’t fully aware of what was going on.

I didn’t really want to look at him anymore. I told him to come up on the bed so I could lay back. He disagreed and said he wanted to stay on the floor. I complied.
It wasn’t much longer before my whole body was tingling, and I was ready to finish. I let him know how close I was by the volume of my moaning. He pulled me in deeper and took everything I had to give. When I was depleted, he commented, “Wow, that was a lot!”
I responded with the only thing I could think of. “Don’t say I didn’t warn you…”
He walked into his bathroom to rinse his mouth as I got dressed. When he came back into the bedroom, he pulled on his shorts and shirt and said, “I’ll walk out with you. I need to take the dog for a walk.”
As we walked down the stairs, we discussed the noise level of his neighbors. I began to wonder about his noise level. That’s when the thought crossed my mind, how many of “us” are there in his roster?
We got outside, and I said goodbye to both him and the dog. On that walk home, I was still feeling euphoric from the bj, but I also decided this was the last time I would have a sexual encounter with the 40 y.o. It was fun, but there were too many things about the whole situation that made me uncomfortable.
After that, he began stalking me on Grindr — heavily. After some time, I blocked him so he could no longer track my whereabouts. For a little while, I would respond to his text messages, but as of late, I’ve taken to simply ignoring him. I’m dreading the day I run into him on the street.
Follow @onegayatatimeA Special Birthday Present
Posted by One Gay at a Time in Gay Dating on June 15, 2011
Warning: This post gets a little graphic towards the end…
Thursday, for my birthday, I went to my favorite watering hole, McSwiggans, where I know the entire staff, and they take good care of me. And boy did they take care of me! As did my friends. Each and every one of my friends bought me a shot, on top of the free beers the bartenders were handed me. Needless to say, I was successfully inebriated by the end of the night, even though the plan was to have just a few drinks at the bar with friends and celebrate on Saturday.
The next morning I woke up. Still drunk. I stumbled to work, counting in my head how many shots I could remember from the night before. While walking, one of the guys from Grindr asked me how my night went. I explained (surprised I could remember it all), and told him how miserable I was. This particular Grindr and I had chatted before on adam4adam.com. I found him interesting and mildly attractive, until I found out he is 40 years old, well beyond my age comfort zone.
The night before, I change my Grindr profile to reflect this special occasion. I don’t exactly know what I was hoping to accomplish by adding “Birthday Weekend” to my profile, but it certainly produced results. Many people took the opportunity to wish me a happy birthday. Some even went as far as to offer me their services as a gift…
I made a decision the next day, Friday morning, not to go out that night. I was going to need to recuperate if I hoped to have a successful Saturday birthday celebration.
That night when I got home from work, the 40 y.o. messaged me again on Grindr. He was a bit of a stalker, always commenting on my location and whereabouts. When he asked me what I was doing for the night, I told him I was sitting home alone on my couch catching up on my DVR.
That’s when he propositioned me with a birthday blowjob. I sat and debated his offer for quite some time. This kind of interaction was totally out of character for me. I’ve never had the random hookup. Part of the idea scared the crap out of me, while the other part thrilled me.
After our exchanges back-and-forth for some time, he managed to convince me this was a good idea. He lived only a few blocks away, my roommates weren’t home, and I wouldn’t have to do anything I didn’t want to. This was a present for me for my birthday. I sheepishly agreed. We exchanged phone numbers, and I gave him my address. On his way over to my apartment, I texted him pre-apologizing for my awkwardness when he arrived. Again, this was not something I had ever done before, so I had no idea how to act or what to do.
When he arrived, I awkwardly introduced myself. I had no idea what I was doing, so I gave him a tour of my apartment. After we chatted, he made a move to kiss me, and suggested we go into the bedroom.
Once in there, he sat me on the bed, pulled my shorts down and went to town orally pleasing me. I laid back and enjoyed my gift. After some time passed, he told me he wanted me inside him. I was very horny, and in the heat of the moment, I agreed. I was smart enough to grab a condom (won’t make that mistake twice), and we went at it. When I was close to finishing, he ripped the condom off and starting blowing me until I finished in his mouth. It felt AMAZING!

At that point, the fun was over. We were both very sweaty, and while he went into the bathroom to clean up, I took the opportunity to towel off and get dressed. When he came back into my bedroom, he got dressed and said to me, “See. That wasn’t so awkward. Was it?” I just replied with a laugh and a smile.
And with that, I walked him to the door and said goodbye. And, with that, he was gone.
I felt amazing, mainly because of the thrill of the risk of the whole situation, and I just got off. But, emotionally, I felt guilty and dirty. I had never used another human being in such a way. This was something new and foreign to me. I needed to purge the guilt and the self-judgement, so I immediately went back to my room, showered, and went to bed.
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