Posts Tagged texting
Two Hours
Posted by One Gay at a Time in Gay Dating on May 1, 2012
After coming to the realization Middle Eastern was not dating material, I began my search for a boyfriend once again. I thought I’d give him a second chance, and he proved to me he wasn’t worthy of that.
I went back to my matchmaker once again – Grindr. I was a little addicted. I found myself spending hours out of my day on the app. I was searching with great fervor. When I woke in the morning, the first thing I did was reach for my phone and fire up Grindr. The next thing I did was grab my tablet and fire up Grindr on that. It was even better on my tablet. The pictures were bigger, I could multitask with my phone, etc. I fully realized how much time I was spending searching for a man. I saw how much of my day was stolen from me. It was like a second job.
On a few occasions, I would strike up a conversation with a guy I thought worthy of my time. One such man lived nearby in Jersey City. We started chatting on Grindr, and I did what I always do. I asked him for his number so I could take things out of the Grindr app and start a conversation over text. I always asked for a picture from the start so I could keep the guys straight in my phone contact list. I kid you not when I tell you I have around 100 contacts from Grindr, Adam4adam.com, ManHunt and OKCupid. I had a system in place as well. Everyone’s name began with where I met them. I was cataloging these guys in theory. Some I never spoke to on the phone, let alone met them in person, but they were saved no less.
After getting this guy’s number, We texted about chatting on the phone some night. He picked up the phone and called me. This earned him a lot of brownie points in my book.
We started with the superficial things – Where we lived. He told me all about his building. I was quite familiar with it. I’d run past it on many occasions. This morphed into a discussion about where we grew up. He was fascinated to learn I grew up out in the country on a farm. Through texting, I’d already learned he was from Canada. I told him how surprised I was he didn’t have a Canadian accent. It popped up a few times, but quite infrequently for someone who grew up there.
I quickly learned he certainly fit the Canadian nice guy stereotype. Everything he said was sweet and polite.
I learned he was slightly older than me. This wasn’t an issue for either of us. I had always liked slightly older men, but I am always leery that older men aren’t thrilled with dating a younger man. I’m quite mature for my age, so I hope my personality can make up for the age gap.
We chatted about our jobs, and I learned he worked in the travel industry. He jetted around the country and internationally quite frequently. He even mentioned the possibility of taking someone like me with him on said trips. I wasn’t getting ahead of myself, but I did enjoy the idea of traveling with my boyfriend to far off locations. He detailed many of the perks, which I really enjoyed, but I didn’t want to let that cloud my perception of him. On the flip side, I told him one of my most embarrassing secrets. I told him I’d never left the country with the exception of Windsor Canada from Detroit. He told me it wasn’t a big deal, and he would help me remedy that issue.
Somehow we got on to the topic of dating and being single and previous lovers. He wasn’t very forthcoming with the information of his major heartbreak, but all it took was one question for him to tell me the overarching story. It seemed it was a sensitive subject, but he was willing to tell me the story. He was dating a man for seven years. This was before he was traveling for work. He was scheduled to go away for work, and at the last-minute, his trip was cancelled. He came home to their shared residence to find his boyfriend in their bed with another man. I expressed my grave sympathy. After seven years with someone he must have been crushed. My heart broke for him. He told me he simply told his boyfriend he needed to move out and that was the end of them.
I tried to lighten the mood and asked him what he likes to drink. Ironically, our lists shared a lot of the same drinks. It was uncanny how similar our pallets are. I learned he too is a fan of Malbec. We discussed how it would need to be present on our first date. I was happy we were on the topic of meeting for a date. He seemed like a great guy. Maybe he was the ship I was searching for in the storm.
I asked him what he was looking for, and he described his ideal situation. Amazingly, our perfect pictures lined up quite impressively. I was really excited to meet him. I only had one picture, and he appeared to be an attractive man. I was more excited to meet him to see how strong the chemistry would be. It was already pretty strong considering we spoke on the phone for two hours.
Only time would tell, and we made tentative plans to grab a drink or dinner in the near future.
Follow @onegayatatimeBack to School
Posted by One Gay at a Time in Gay Dating on April 30, 2012
With things gently crumbling between Chelsea and I, I decided to give Middle Eastern another chance. I enjoyed spending time with him, and he certainly was a nice kid. I wasn’t sure if I could see myself dating a guy still in college, but I figured it certainly couldn’t hurt to give it a shot.
Wednesday morning while I was on my run, I did a lot of thinking. I was trying to clear my head. I realized I wasn’t all that into Chelsea after all. There were a few things about him I liked, but there was nothing there that got me truly excited to see him again. I didn’t want to waste either of our time, so I decided it was best to tell him how I felt.
While at work Wednesday afternoon I thought about him a M.E. He was such a sweet guy, he was quite interested in me, he was smart… There were a lot of great qualities there. The big question — Is he mature enough for me. I’d never dated someone that much younger than me before. I wasn’t basing this on a number. I was basing it more on his personality.
The other side of the coin was how great he was in bed. I really enjoyed being with him the first time. I fantasized about he and I having sex in the locker room shower of my gym.
When I got home that evening, I told him to come over. He didn’t hesitate. He finished what he needed to do, and he made his way to Hoboken.
Warning: The following may be too graphic for some. When he arrived, we immediately went to my bedroom. He was hungry for sex. We quickly stripped each other until we were naked and enjoyed kissing, groping, sucking, etc. It was nice to be with a man who was so passionate once again. He loved to kiss and was good at it. I didn’t have a single complaint about him. After ample foreplay, we had sex. It appeared I created a bottom. He was all about it now, even begging for it this time. It was hot. I really like how masculine he was, but also how much he was willing to bottom for me. This was an unusual combination from my experience. [I actually had to walk away from the computer for a minute because I was thinking about the fun we had and getting a bit too excited while writing this].
Afterwards, I went into the bathroom to relieve myself. I came back to my bedroom to find M.E. on his phone. He was doing a lot of typing. I encouraged him to come to the living room with me to watch TV and be somewhat social with my roommates, but he told me he’d be out in a minute. He had a few messages he needed to reply to.
Since I last saw him, he sprained his ankle. I’d been giving him some advice, having sprained both mine multiple times and being related to a physical therapist and someone who teaches athletic training. As a result of this sprain, he wasn’t able to go on his planned spring break. He told me he was working out the logistics of rescheduling the trip for another time.
I left the room and went to the living room. I’m not 100% sure why this idea popped in my head, but I wondered if he might be on Grindr. I had my phone and tablet with me, so I pulled up the app and checked it out. He didn’t show up on either. Maybe he wasn’t on there, but my suspicions weren’t fully satisfied. When about ten minutes passed, I went back to the room to see if he was coming. He put some of my clothes on and joined me. We watched another episode of Modern Family together.
While he watched, he sat behind me in the chair, and I laid between his legs watching the show. We both laughed a lot. By the time the show was over, it was late. I suggested we go to bed, and he agreed. I asked him what he’d told his roommates about where he was going. He told them he was heading home for the night.
While he was brushing his teeth, he left his phone on my night stand. My mind shot back to the chance I had to look at N‘s phone the night I witnessed him kissing another man in front of me. Boston convinced me it was a bad idea. I wasn’t going to make that mistake again. I had no problem if he was using Grindr. We were not exclusive. I was seeing other people. I just found it incredibly offensive if he was cruising Grindr from the comfort of my apartment. That was not okay in my book. I needed to know. I turned his iPhone on, and sure enough, at the top of the screen was an icon for Grindr showing he had 23 messages. I placed the phone back down on the night stand and processed what I just learned. Not only did he have messages, but he blocked me on both my accounts so I couldn’t see that he was cruising Grindr.
It was that exact moment I decided M.E. and I wouldn’t date after all. It was fine if we spent time together and enjoyed having sex, but I wasn’t going to date him long-term. I couldn’t trust him. I wasn’t mad he may be seeing other guys or even having sex with them. I was mad he was attempting to line up other guys from my bedroom. I decided not to say anything right then and there. It would simply form my future behavior.
He came back to the bedroom, and we both climbed into bed. I wrapped my arms around him and he climbed into the natural crevice I created as big spoon until we dozed off.
When we woke in the morning, we fooled around a bit. I had to go to work, but I made sure to set an extra early alarm to allow for a little fun in the bed followed by a shower with each other. It was sexy and a nice way to start my day.
We left together, and he gave me a ride to the PATH. Since he told me last time he wished I kissed him when he dropped me off, I decided to oblige that request. I gave him a nice smooch before heading into the city to start my workday. I liked M.E., but not enough to make him my boyfriend — Not after what I learned. But, it would be nice to have someone around regularly to share affection and pleasure with on occasion. Maybe this was the start of a beautiful friendship…
Follow @onegayatatimeHoboken Seconds
Posted by One Gay at a Time in Gay Dating on April 27, 2012
Today is another Fast Forward Friday!!!
Hope you are enjoying these. It will help bring the blog a little closer to real time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!
Back to your special edition of One Gay At A Time…
After our date on Monday, I wasn’t sure when I’d see Chelsea again. Things were moving forward at a nice pace, but I still wasn’t diving in like I normally do. What was holding me back? Was I finally going about things the right way? Was I not fully interested in him?
That Tuesday was his last day in his current role at his job. He went out celebrating with coworkers, and when they were nearing the end of their evening of drinks and fun, he texted to ask if he could come by. Two days in a row. I certainly didn’t have a problem with that. He obviously wanted to see me, and I was very happy about that. One of his coworkers lives across the street from me, and they were able to share a car. I told him I’d be thrilled if he came over.
When he arrived, I could tell he was quite tipsy. It was cute how he couldn’t hold his liquor. Alcohol gets him quite lubricated. He was very flirtatious once again, as he was at the end of our first date. Everyone was buying him drinks since he was no longer be working out of that office. His new territory was Massachusetts, Connecticut, New Hampshire, etc.
We started with some kissing when he walked in the door. I took his hand and led him to my bedroom. He was wearing a full suit, so I found him some more comfortable clothes. In the middle of changing, we began to fool around. It was fun. He was a good kisser, and we were making out all over my bed. I liked having someone of the same size to hold, kiss and roll around with. This time around, he certainly wasn’t shy about being in just his briefs. We had a lot of fun with each other and still no sex. And, I was fine with this. I knew things would progress slowly, and I was quite happy about that. ( I was missing sex a little).
He was a sweet guy, but that night was a little different. I saw a side of him I hadn’t only caught a glimpse of. A lot of his drama started pouring out, and I realized he had just been trying to keep it all down in an attempt to not scare me off. Now, I was getting to see the real Chelsea. I went to bed with a different picture in my head. Was this what was holding me back? Did I think maybe he was a bit too gay for me?
We watched TV and ate some dinner. a lot of the little things I ignored previously were bothering me that night. We went to bed at a reasonable hour. After sleeping together twice and it not ending well, I made a suggestion at the risk of sounding cold. I told him there was no need for us to snuggle while we slept. I tried to be honest and realistic about it. I said, “We can cuddle and snuggle, and when we’re ready to fall asleep, we can curl up on opposite sides of the bed. That way you will get a good night’s rest.” I also took this as the opportunity to tell him I wanted to go for a run the following morning. I was finally getting into a workout groove, and I didn’t want to throw it off. I could sneak out while he was still sleeping, and when I returned we could get ready to head into the city together. With that, we both went to sleep on opposite sides of my California King bed.
I woke in the morning and quietly snuck out to pound the pavement. I had a good run. I needed to clear my head, and the run was just the ticket. When I returned, I hopped in the shower. When I came out of the shower, I gently woke Chelsea. Normally, I would have slipped back into bed with him to cuddle, but I wasn’t feeling it. It was then I realized I wasn’t particularly sexually attracted to him. He was very shy about his body, and while I enjoyed the slower timeline and waiting, a part of me knew it was an important part of the relationship I couldn’t ignore. I’d sacrificed that in the past too many times. I wouldn’t make that mistake again.
I continued to get ready. I was pretty quiet, but then again, I usually am after I work out. I’m also not a morning person to begin with. I either get quiet or I become combative, as my mother learned many a time riding home from swim practice in high school. There was little talk and discussion as we got ready for work/for him to head back home. When we emerged from my room, I found a mess left by my roommate. I detailed to him why I was so annoyed and how this was a common occurrence.
The walk to the PATH wasn’t exactly full of chatter either. I struggled to think about things to talk about. I fixated on his new job and asking the questions about how he was going to handle it. Subconsciously, I was noticing all the things in the back of my head I’d brushed aside once again. Now, my cons list was growing.
When we got to his stop, I gave him a quick peck on the lips. I could tell it made him uncomfortable, but I was trying to force myself to stop being ashamed of being gay. If he were a woman, I’d have had no problem kissing her to say goodbye on the PATH. Why should I censor myself just because he was a man?
Later that day, I received a text from him asking me if everything was okay, or was it my roommate. I blamed my quietness on being annoyed with my roommate, but in reality, I was no longer looking at him as a prospect.
That weekend, I went shopping with my friend, P. While at the Woodbury Common Outlets, I got a text from Chelsea asking, “Will I see you at the end of the week?” I didn’t want to drag this out. I decided in my mind I was no longer interested. It was going to be tough to convince myself otherwise. I replied, “[Chelsea], I don’t want to lead you on or anything, but I’ve been giving it some thought. I just don’t know if we’re a strong match. You’re a really nice guy, I just don’t know you’re the guy for me. I want someone who is going to be around more… That’s important to me. Hope you understand.” Immediately, he responded, “Yup. I feel the same way :). Anyways, all good here. Please do me a favor and put me in touch with your friend about subletting my apartment, and I’ll see you sometimes in the city :).” I don’t know if that was his way of protecting himself emotionally or if it is how he truly felt. Either way, it was a clean break. All was good, and we could still be friends if we ran into each other in the future.
Chelsea Comes to Hoboken
Posted by One Gay at a Time in Gay Dating on April 25, 2012
My Friday off was certainly an eventful one. I spent the better portion of the afternoon planning and participating in my first real threesome. I was already starting to judge myself and question all my recent behavior. A large part of me knew this was not who I was. I was completely acting out, but another part of me realized these were my gay “formidable years.” I never hooked up with guys in college while all my male friends were taking girls home from the bar. This was my wild time. Basically, I was giving myself license to have emotionless sex for sport.
That being said, I was still searching for the guy who would get me off Grindr and be the reason to settle down. I’d already gone on one good date with Chelsea. He asked what my plans were for the evening. I told him I had none since I had the day off, and he asked if we could do something together. I didn’t feel like doing anything crazy or going out, so I requested a lazy night in and suggested he come to my place. “Cuddle night?” he replied. “Definitely,” I said.
I still felt a little disgusted with myself for my afternoon behavior, but I also hoped maybe he could help distract me. He would certainly be something to get my mind off it. I took all my sheets off my bed and threw them in the washing machine. I hopped in the shower once again. I needed a cleanse.
I texted him back and told him I would make us dinner, and we could watch a movie. He agreed that sounded like a great idea, but he told me he’d already eaten. I made myself something quick before he came over.
“Do I have to come back to NYC late by myself?” he added. I told him he could certainly spend the night. In fact, I would very much enjoy that. He tried to convince me to come into the city, but I wasn’t about to budge. I’d already done one date in his neighborhood. I didn’t want to go into the city that evening since I wasn’t already there for work. He painted a better picture of what I was asking him to do: “Mind you, I don’t even go see my friends in Brooklyn. So this better be scoring me some hefty points! Haha! LMAO. You can ask my friends how much of a NYC snob I am. I’m like who? What? Why? Do I need a passport? And does Jet Blue fly there?” I quickly responded, “This isn’t my first rodeo. You’re not the first guy I’ve stolen out of the city.” Every guy I’ve convinced to come over to Hoboken has fallen in love with it and become an advocate. I am slowly introducing the NYC gay community to the great city of Hoboken one gay at a time :).
He agreed to stay over, as long as we agreed to behave. I told him I had no problem with that, and I appreciated him wanting to take things slow. I was very surprised by this, considering we met on Grindr, and I learned he’d done the hookup thing more than a handful of times.
When he arrived, I got him some comfortable clothes to wear, and we settled in on the couch with a few refreshments. We went through the guide trying to find a movie to watch. Finally, we settled on Drive, with Ryan Gosling. We laid on the couch with him in my arms the entire film. It was nice to snuggle with a man. It was very romantic. We both thoroughly enjoyed the movie, and when it was over, it was decently late. We decided to head to bed.
I found it adorable he didn’t take his shorts and shirt off when we went to bed. I don’t exactly sleep naked, but I have a hard time sleeping with clothes on. I find them restricting. I stripped down to my boxer briefs and encouraged (playfully removed the shorts I lent him) him to get comfortable before spooning with him a little. He warned me about getting too fresh, but I told him to relax. “I’m just trying to cuddle, not rape you. Stop fussing,” I jokingly stated. He did relax, and we got into a comfortable spooning position before finally dozing off for the night.
That night, neither of us slept very well. He was a thrasher and constantly woke up. I didn’t mind too much because I didn’t have anything to do the next day but lounge around. It was nice change to be sharing my bed with such a sweet guy. This had potential, and we certainly weren’t rushing things…
Follow @onegayatatimeA Colombian Night
Posted by One Gay at a Time in Gay Dating on April 23, 2012
After a very nice date Wednesday, I was pretty happy. It had been a while since I had a good first date. I spent a lot of time having strings of bad first dates or finding guys to simply have fun with and send on their way. Nothing was fulfilling, but for the first time since PR, I was hopeful.
Thursday nights are always my volleyball nights. It’s the one night of the week I get to fulfill my competitive edge and work out some of the frustrations that have built up over the week. I always look forward to it, and I almost always commence the night at my favorite watering hole, McSwiggans.
Before riding home on the motorcycle from volleyball, I checked Grindr to see if I had any messages. A few started flowing in as soon as I opened the application. Where I play volleyball is a hotbed for Hispanic Grindrs and it seems they flock to me like a moth to the flame.
When I got home, I started chatting with one guy who seemed nice enough. When I told him where I lived, he was confused why I showed up so much closer. I explained to him why I was in his neighborhood. He was disappointed to hear I’d already left the area. “We could have grabbed a drink or something.” I told him it wouldn’t have worked out since I had the motorcycle and was disgusting from playing three games.
I did, however, invite him to come to Hoboken and join my friends and I at the bar. I had already texted a few friends and told them to meet me there. Two of my friends were already in the process of getting ready to meet me.
He entertained the idea for a few minutes before finally accepting my offer and dragging his roommate along for the ride. I was going into this arrangement mainly thinking this would be a friendly drink. I made it clear I had friends with me so he wouldn’t think I was asking him out on a date.
I arrived at the bar at the same time my friends did. We grabbed beers and sat at one of the tables. I informed both my friends a guy and his roommate would be coming by to hang out. My male friend looked very leery, but I told him this was just a friendly drink thing. I think he was worried he was basically going to sit through one of my dates. After some time passed, my Hispanic Grindr friend and I started texting. He arrived and was sitting at the bar. I had walked up and ordered right next to him without noticing him there.
I immediately walked over and said hi to him and his roommate and introduced myself. I called my two friends over to introduce them as well.
It wasn’t long before my male friend’s comfort level dropped, and he decided to meet other friends at another bar. My female friend, P, was hitting it off with the guy I met through Grindr. They are both Colombian and were sharing a few stories. The other guys seemed very nice and decently cool. We started with the small talk and then got into more of a discussion. It was nice, but I wasn’t really attracted to this guy at all. This was purely going to be a friendly drink. We talked for at least another hour, and more than a few rounds later, we decided to head out.
He was a really nice guy, and we all left at the same time. P lived uptown and in the direction they were heading to go home, so they offered to give her a ride home. They were parked in the direction of my apartment, so I agreed to walk them to their car at the least before heading home. As we got closer, the convinced me to hop in and let them drop me off. I finally agreed.
When we got to my apartment, it was slightly awkward because I could tell this guy wanted a moment alone with me. Maybe he wanted a kiss out of the night. I don’t know. I reached up and tapped his shoulder and said, “Thanks for coming down here. It was fun. We should connect again sometime soon.” He smiled and agreed. It was my subtle way of letting him down easy without getting his hopes up for a “date.”
Finally, I was making gay friends without overcomplicating things with hookups or sex. I needed to do more of this. I had one local gay friend, and he was all but married with a serious boyfriend, an apartment, a shared dog and a shared car. This was something I looked forward to, but maybe I needed to find a wingman to help me find the right guy first.
Follow @onegayatatimeHAPPY ANNIVERSARY!
Posted by One Gay at a Time in Gay News on April 20, 2012
Today is One Gay At A Time’s 1 year anniversary.
It’s hard to believe it’s already been a year. At times, it seems like longer. One year ago today, I hatched the idea to create the nom de plume, One Gay At A Time and beging writing a blog.
I want to take this opportunity to thank all of you, my faithful readers! We’ve been through a lot together to say the least. I feel fortunate to have conversed with many of you and gain a different perspective on a tumultuous dating life. Please keep reading, and I will keep writing. If I help just one person find comfort in themselves, I feel more than accomplished.
Here’s to sharing many, many anniversaries in the future.
Follow @onegayatatimeOn A Sexual Roll
Posted by One Gay at a Time in Gay Dating on April 18, 2012
I have a generous amount of vacation days, as I did a very good job negotiating when I was hired at my job. I don’t, however, have friends who share the same luck. They can either take the time off and have no money to travel, or they have money, but can’t get away from work. On top of this, being single leaves me only with the option to travel – Alone. I don’t enjoy this. As a result, I build up all these vacation days and never use them.
When the new year arrives, I have until the end of March to use up all the days I carried over. As a result, I start giving myself four day work-weeks and have staycations. I decided to take Monday off after the local holiday in Hoboken. As per my usual, I woke up horny and turned to Grindr. I tried to get one guy I’d been flirting with to come to my place. He lived in the city in Harlem, so no matter how hard I tried, he was not going to come to Hoboken.
After him, I went through a ton of Grindr guys trying to find someone to come over for some morning fun. None were biting. I turned Grindr off after what I’m sure was over an hour of surfing, and hopped on the computer. I thought I would give adam4adam a shot. I had messaged a few guys, but I wasn’t getting a response. That was until I found one guy who is 26 and worked in the area.
He was a good-looking guy, as per his profile pictures. We began exchanging messages. He unlocked his pictures, and I got a glimpse of his face finally. He was a very sexy, light-skinned black man. He had this college jock look about him, and I was very turned on. His body was fit, he was clean-cut, and his smile was utterly adorable.
I asked him if he’d be free later to swing by. He had a light day at work since his boss was out of the office. We discussed logistics since he worked in neighboring Jersey City. He could either take a cab or the light rail to my place. I gave him all his options, and we made a plan for him to come by around 4:00. I learned he was usually a top, but he was willing to bottom for me. This was extra exciting to me, because I had greater hope he’d be a more masculine man than most typical bottoms.
When he arrived, I was immediately taken back by how sexy he was in his work clothes. Then I noticed his incredible blue eyes. He looked just like Michael Ealy. He was very masculine and had on slacks, a dress shirt, a tie and an incredible smile. He wasn’t nervous about this at all, which I found to be very sexy. I led him into my room, and he immediately began undressing himself. I liked his matter-of-factness — His “I know the drill” style. I sat on the bed talking to him as he undid his tie, stripped off his shirt, removed his shoes and took off his pants.
Warning: The following may be too graphic for some. The man had an amazing body. I was very pleased. I could tell he takes good care of his body, and I was ready to ravage it. I wanted to touch every inch of his milk chocolate colored skin. I was still sitting on the bed in my gym shorts and tank top when he unexpectedly took off his boxer briefs as well. If I wasn’t already excited before, now I was rock hard. He walked toward me as I stood and removed my clothes as well.
He was a well gifted man, and once we were both fully undressed, we laid on the bed with him on top of me making out for a bit. He had amazing lips and knew how to use them. He had a strong body, and I enjoyed wrapping my arms around him. It was hot! We began to fool around and explore each other’s bodies.
Ater some making out and mutual oral pleasure, he got into position for me to use some of the techniques I’d read in Tickle My Tush. I knew he was normally a top, so I took the time to make sure he was fully ready and not rush things. I was enjoying myself as well. He seemed to be really enjoying himself as well from the sound of things.
That’s when I reached over the edge of the bed to my nightstand and grabbed a condom and some lube. He was face down on the bed in front of me, and the real fun was about to begin. I really enjoyed being up against his body and feeling him. He may not have been a bottom, but he sure was passionate in the bedroom and knew how to use his body. The sex was great, and eventually he finished. Seconds after that I too pulled back and finished. It was very hot! I grabbed a towel to clean up his back and the sheets below while we exchanged a few more kisses and expressed our enjoyment with each other.
Just as he undressed like he knew the drill, he began to get dressed. I learned he was heading back to work. I was surprised because he lived in the city. I assumed I was a pit stop on the way home. I felt bad for him he had to return to the office, but I didn’t regret inviting him over. I had a great time with him and would certainly be willing to have him swing by again sometime.
I walked him to the door and gave him another kiss goodbye. He was such a polite gentleman. I could tell him momma did a good job raising him. He thanked me, to which I replied, “Thank me!? Thank you! That was great! Anytime you want to do this again, you know how to reach me.” And with that, he was gone.
In the coming weeks, we’d try to do it again, but he was having a busy week. I could tell he was more than just a hot body, so after that, I asked him if he’d ever be interested in grabbing a drink sometime, but I got no response. Perhaps he will just remain a fond memory of a day off…
Follow @onegayatatimeWinding Down
Posted by One Gay at a Time in Gay Dating on April 17, 2012
Although things didn’t exactly end the way I would have hoped, I had a really great time with my new uptown Grindr friend. He was a very down-to-earth, sexy man whose body I found irresistible.
I made my way home on my motorcycle only to find my apartment full of my friends and my roommates’ friends. They apparently noticed my Irish exit, but I was shocked to find none of them texted me to find out where I’d gone. They didn’t seem to care much. They were all drunk and about to smoke.
I put my helmet in my room and joined in the fun. D pulled me aside and asked if I’d gone to hook up, and I didn’t lie. I nodded my head in agreement, and he said, “I knew it!” with a smile.
My roommate immediately mentioned breaking my glass planter that sits in the window, but failed to apologize for the act. She simply pushed it into a pile, plants and all, and left it there on the floor. After sitting in the room a solid ten minutes, my friend K announces, “Where’s [One Gay At A Time]?” I responded, “Really K! How many have you had!?” We all laughed.
The previous night, I talked to a guy on OKCupid who was quite an athlete. He seemed like a really fun guy, and I was anxious to meet him. We’d emailed a few times back and forth, and I learned he would be coming to Hoboken for the festivities in the evening. Ironically enough, he would be in the apartment across the street. The same apartment my roommate and I scoped out on numerous occasions, noticing a gay couple lives there. I texted him to see if he was there, but he told me he decided to stay home after not feeling well.
This, of course turned my attention to the apartment across the way. My roommate and I had scoped out this apartment many times starting on New Year’s Eve when we presumed two mo’s lived there. This night, they were having a party. We noticed many men, and we tried to make a sign with a sharpie and the inside of a paper bag. It was no use. Anyone’s attention that was looking out the window was drawn to our neighbors upstairs. They too were having a raucous party.
I decided to use technology to find a way to make friends with the mo’s across the street. I pulled up Grindr and tried to find anyone very close. When I finally got in touch with someone nearby and asked him if they were at that address, I came to learn that person had left the party already. I made many more futile attempts to reach out to the party. A few of us watched with curiosity when people moved into the bedroom, but nothing exciting happened. Our front window became a version of “Rear Window.”
When I grew tired of my new entertainment, I made my way to bed. It was a long day, but a fun day. I was beat.
The next day, I returned the favor of a friend for helping me move. I rode my motorcycle over to his new apartment and dug in moving bags and boxes. When we drove to his old place, I realized we were in the same neighborhood as Indiana Jones lived. I pulled out my phone and texted him to see if he was around. It’d been months since I last saw him, and I was anxious to see him again. We were due for a catch-up. I didn’t hear back from him that day, but I wouldn’t give up at that.
Follow @onegayatatimeWhere’d He Go?
Posted by One Gay at a Time in Gay Dating on April 16, 2012
FraI already started my morning off with a little frisky visit and some well appreciated service. It was time to join the real festivities.
I walked out into my kitchen to find my roommate with all her college friends and my other roommate with his girlfriend. I thought I pulled a fast one on all of them sneaking my visitor in the back door, but I was wrong. My male roommate saw him come in. He and his girlfriend questioned me on it, and I was completely honest with what happened. They were fascinated by how transactional it was. They couldn’t believe it, and his girl gave me a high-five.
I celebrated myself with a nice cold beer from the fridge. It was already 1:00 and I was well behind the rest of Hoboken. Before I finished my shower, I had four down. That would be enough to scratch the surface.
I got dressed and convinced my roommate and his girlfriend to come with me to a friend’s apartment. She was having her annual St. Patty’s Day bash. I was meeting D and K there as well. I was happy D was going to be in town. Since his car got a flat, he wouldn’t be visiting his girlfriend in Philly.
When I got there, the party was already well underway. I sat on the arm of the couch and conversed with my friends. I just took in the scene. For some reason, I wasn’t really feeling St. Patty’s Day this year like years passed. I didn’t feel the need to get sloppy drunk.
Of course, since my bladder has shrunk since college, I had to go to the bathroom. Since I was somewhat bored at the party, I was chatting with a sexy man I’d been chatting with for some time on Grindr. We’d talked about getting together so many times, but never did. Things were getting very flirtatious and leading toward an afternoon hookup. When I went to the bathroom, he suggested I come over. I took the opportunity to sneak out the door when I finished in the restroom instead of returning to the party. I’m sure it was just a matter of time before my friends realized I’d gone, but it wouldn’t be immediate.
I wasn’t even slightly drunk. I’d been anxious to see this guy for some time. I wasn’t about to let the opportunity pass. I quickly walked home, grabbed my helmet, hopped on my motorcycle and sped off uptown. Before I left the party, my Grindr friend asked me how I felt about glory holes. I told him I’d never used one before. When he sent me a picture of a sheet with a hole cut in it and a caption reading, “How would you feel about this?” I became excited. He told me he’d leave the door unlocked. I was to walk in, come to the sheet, unzip and let him take care of the rest.
Warning: The following may be too graphic for some. As I entered, I noticed how nice his place was. I was a little shocked. I walked straight to the sheet hanging in the bathroom door. I hadn’t even fully unzipped before he reached his hand around the sheet and began. It felt amazing! He continued for some time before I reached my hand around the sheet and began to stroke the back of his head. I could feel him, but I couldn’t see him. Finally, my curiosity got the best of me, and I just pushed the sheet to the side. I wanted to see him. He was very attractive in his pictures and even more so in person. On top of that, the only thing he was wearing was work boots.
After a little more time, he turned around and I began grinding myself against his backside. He was extremely hot and he knew how to use his body. I reached around and used my hand to pleasure him as well. He was VERY gifted. I hadn’t felt one like that since my friend in San Francisco.
He then requested we move things to the couch. I sat down, and he straddled my lap. It didn’t take long before he finished all over my chest and without warning. I had no idea it was coming. I tried to finish as well, but it was no use. Between my morning visit and the few beers I had, I sat there for quite some time without climaxing. He was so hot and he tried everything to help me finish, but it was no use. I gave up and apologized. I could tell he was very disappointed. He blamed the drinking, and I concurred that was to fault.
As he stood in front of me, I took all of him in. He had a spectacular body, and I let him know it. I asked him about his workout routine, and he told me he didn’t since his heart attack. He elaborated and told me it was no big deal, but I was a little worried. I could only think of him keeling over in front of me.
We chatted a little bit more while I got dressed and looked around a bit. He told me he had a roommate, but he wasn’t home. Something didn’t quite line up, but for some reason, I was buying the story. While we chatted, he stood in front of me in just his boots with his large gifts swinging back and forth. He was very proud of them as well. He put sweatpants on so he could walk the dog, and I could see his large bulge. I commented on it, and he commented how he loved how people would check it out, especially the guys with their girlfriends. I was so turned on. I also learned he managed a bar in the city, and he told me I should hit it up sometime.
We talked about meeting up again sometime soon. We both thought the other was thoroughly sexy and wanted a repeat. He was particularly looking for a sequel since he didn’t get a happy ending from our first encounter.
I said goodbye and made my way back downtown to my apartment…
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 
Check That Off the List
Posted by One Gay at a Time in Gay Dating on April 24, 2012
Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.
For some time, I’d been speaking to a few guys on Grindr who happened to be tops. When we both learned we were the same position, discussion turned to other options, such as bringing in a third. We were both really attracted to each other, but neither was willing to bottom for the other.
Many men dream about the threesome. Straight men fantasize about it constantly, and I assume it’s a big gay male fantasy as well. The only difference is gay men probably act on it and achieve it far more often. It certainly isn’t, however, easy to pull off. You have to organize three different mens’ schedules and also take into consideration their taste in other men. We all know how finicky gay men can be.
I woke up Friday with no agenda and morning wood. I wanted to take care of it, but I also wanted to act on my recent fantasy of a threesome. I started with one of the most promising guys who I’d discussed this with before. He wasn’t getting back to me. I began going through more than a few permutations trying to find 2 guys willing to participate who weren’t occupied with work.
After much discussion about who could host and who wouldn’t host, I managed to get my original group together, but not without issue. I had to ride my motorcycle into New York City to pick the bottom up. He wasn’t comfortable coming out to Hoboken alone, and the other guy wasn’t willing to host strangers. Strange to think he had no problem hopping into bed with strangers, just as long as it wasn’t his own. I rode in and picked him up. It was slightly awkward, but it all fell right into place. He hopped on the back of the bike, and we rode off to my place.
Warning: The following may be too graphic for some. We arrived before the other guy. I didn’t know the rules, but I was looking to wait for the vers guy to arrive before we got started. The bottom wasn’t so patient. He wasn’t the best looking man in the world, but he had a great body. He started kissing all over me until he undid my pants and started orally pleasuring me. He was quite good. He undid his pants as well and revealed a generous gift. He asked me if we could go to the bedroom until the other guy arrived. I encouraged him to wait since he was only a few blocks away.
When he arrived, the bottom walked to my bedroom and began to undress. I brought the vers guy into my room, and he and I began to undress. I wasn’t as thrilled with him. He looked much better in his pictures, but there certainly wasn’t anything wrong with him. You can’t win ‘em all. I laid on the bed in my boxer briefs while the other two joined me and began rubbing me all over and kissing me. I felt like a king. Everyone was there serving me, and it felt great!
This guy was incredibly awkward. He looked like he was having a seizure. His sex was spastic and crazy. On top of that, he was very particular and insisted I use the condoms and lube he brought. While he was inside the bottom, I climbed on top and penetrated the vers. This was not the easiest sex position by any means, and it did not last long. The logistics of three people getting the same rhythm are nearly impossible. It’s obvious in porn when this happens, they are doing it for the camera and certainly not for pleasure.
We swapped positions a few times and had already gone through a substantial amount of condoms. If one thing was certain, I was going to be wrapped up at all times! Finally, I suggested we move things to my shower.
We went through a few permutations of positions in the shower before I told them I simply wanted to watch them while I took care of myself. The bottom protested. I could tell he was very annoyed by the vers and wanted me more. When we ran out of warm water, we all toweled off. The bottom needed to excuse himself. He was feeling light-headed. He made his way out to the living room in his towel.
I was left with the spaz in my room, and I wasn’t thrilled. We tried a go at it for a short bit, but I was much more interested in the guy sitting in the living room. We stopped and moved things out to the living room after closing all the curtains. The bottom was feeling better, so he was eager for me again. He hopped on the chair and asked me to go again with him.
The vers guy almost immediately began to get dressed, noting he had to get back home to finish work. The bottom was going to head back in with him so he wouldn’t get lost, but the vers wasn’t willing to wait for him to get dressed. The bottom asked me to ride him back onto the city, but I told him I would give him a ride as far as the PATH. From there on, he was on his own.
We chatted a bit about how spastic the other guy was. Neither of us were thrilled with him, but it is what it is. The bottom got dressed and hopped on the back of my motorcycle. When we got to the PATH, I gave him directions for getting back home.
I sped off home. I was in need of a serious shower. Since the morning’s activities began, I felt incredibly dirty.
If you’re considering a threesome, I strongly encourage you to think it out first. Don’t just jump into it to satisfy some great fantasy you’ve seen many times in porn. If you have the constitution for it, then by all means, do what makes you happy. But, if you’re thinking twice, I strongly suggest you leave the fantasy to your mouse clicking.
There was nothing sexy about what happened. It did not live up to the fantasy I had originally dreamed of. It was awkward and at times laborious. I needed to wash away the shame and guilt I felt, but it was no use. Those would stick around for at least the remainder of the day.
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