Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.
This post is embarrassing. It is now especially embarrassing because a few readers have commented about my promiscuous ways, but nonetheless, I will report the incident honestly and to my best ability. I, in no way shape or form, condone the following behavior. An early warning as well – this post will be graphic.
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.
Finally, I found one, and we both began to hunt for that elusive third. There were many roadblocks, and lots of waiting to hear back when questions were posed. I thought I had it all worked out, when one of the guys went dark on me. I was very disappointed because I thought I found the perfect combination. One top (me), one bottom, and one vers. When the bottom got a flat tire, it all went to $hit. All this juggling really made me realize why this never happened before.
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!
Then the underwear was removed on all parties. There was lots of rubbing, kissing, sucking, etc. After some time, I broke out the condoms and lube. I was horny and ready to get started with the real fun. After using his poppers, the bottom was ready and eager, so I penetrated him while he orally pleasured the vers. Then the vers came to my side of the bed. We’d already discussed I wasn’t bottoming, but he thought I could be persuaded. I told him sorry, but no. I backed off and let him have a turn with the bottom.
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.
There was something that really turned me on watching the other two guys have sex. I pulled out and encouraged the vers to join in again. I wanted to sit on the couch and finish while I watched them. The bottom wasn’t happy about this because the vers was bad at sex. All three of us were on the couch when I finally finished on my chest. The vers reached climax as well, but the bottom seemed content with stopping before he finished.
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.
Yet another video I’d like to share. This one is a music video for one of my new favorite groups, Duck Sauce. Great song and love the sexual connotations, but may not be safe for work depending on what you do. Enjoy!
On with the story…
Every Tuesday in Hoboken is free movie night if you have Cablevision’s triple play. I do not, but I have some very generous friends who do, and they lend me their card when they’re not using it.
I asked Smiles if he wanted to catch a movie and dinner. He told me he could possibly do dinner, but there was no way he could do the movie. He had to be up at 6:30 the following morning for a work meeting, so spending the night in my bed was off the table.
While I was finishing up work, he was moving his final boxes into his storage unit from Harlem. I agreed to help him when I arrived downtown, but when I got there, he was already finished.
I walked him back to his apartment. We talked about his day on the walk. I waited while he showered and changed after loading and unloading all those boxes to go to dinner.
While he was moving the boxes, both his parents called, separately. He was a little worried, so on the way to the restaurant, he dialed his mother. Smiles said he needed to walk a while, so we kinda just went for a stroll. We talked a little about work and how he got to where he is today. We stopped in a few stores on the way. We were walking for over a half hour before we settled on a spot to grab some grub.
We settled on Peels. When he returned to the table after washing his hands, the conversation was very dry. There were many long awkward pauses throughout the night. I struggled to think about anything we could to talk about. Nothing. I didn’t know what to do. We continued to eat in silence. It was incredibly awkward. I was so worried we’d hit that point already where we had nothing to talk about. I was petrified.
Was he distracted by the phone calls? Did something happen? Who knows?
When we finished eating, we paid the bill and began walking back toward his place and the PATH. We ran into a friend along the way, and Smiles chatted with him for a short while after barely introducing me. After we left the friend, he explained who he was and how close a friend he is. I was a little surprised. If he was such a good friend, then why was he so casual when introducing me. Maybe I didn’t mean as much to him as he did to me. Maybe I was putting too much of myself out there too soon. We’d been dating for a month and a half. I thought we’d be closer knit at this point, but maybe I was wrong. Maybe I had different expectations.
As we walked, he told me he was tired and a bit out of it. This wasn’t news to me after the awkward dinner we just had. He walked me to a crossroad and said goodbye. When I went in for a kiss, I barely received anything in return. It was almost like a child begrudgingly accepting a kiss from a grandparent. I felt like a piece of sh*t.
As I walked by myself to the PATH, I wondered if this thing had run its course. How much longer were we going to go before he fully opened up to me? — Before I didn’t have to wonder where I stood with him? I was tired of the uncertainty. It was dragging me down.
I needed to talk to someone, so I called Boston. No answer as usual. College always gets in the way of our friendship!
Next, I called LES to see what he was up to. No answer, so I left a message.
Then I texted the Principal just to say hi and see how he was doing. When I came above ground on the other side of the Hudson River, I received a response from him. We texted back-n-forth for the remainder of my walk home. When I got to my apartment, I immediately climbed into bed. I was depressed. This relationship was looking pretty bleak. Silence at dinner and an awkward kiss goodnight. Once again, maybe he just wasn’t into me.
The Principal and I continued to text over the next hour while I watched some TV. I explained to him I still had some feelings for him, however, the distance thing just wouldn’t work out for me. Apparently, I opened up a can of worms there. He really did miss me. I’m not sure why I felt the need to reach out to the Prinicpal that night. I thought I passed that chapter in the story. I think I did it for selfish reasons because I needed to feel wanted again. I knew the Principal would provide that for me. Looking back, I never should have done that.
In my mode of depression, I also responded to one of the guys who had hit me up on OKCupid. I asked him if he wanted to grab a drink sometime. I was taking my friends’ advice. I wasn’t going to put all my eggs in one basket. The guy responded, and we scheduled a date for the following night…
I asked Smiles if he wanted to catch a movie and dinner. He told me he could possibly do dinner, but there was no way he could do the movie. He had to be up at 6:30 the following morning for a work meeting, so spending the night in my bed was off the table.
We settled on Peels. When he returned to the table after washing his hands, the conversation was very dry. There were many long awkward pauses throughout the night. I struggled to think about anything we could to talk about. Nothing. I didn’t know what to do. We continued to eat in silence. It was incredibly awkward. I was so worried we’d hit that point already where we had nothing to talk about. I was petrified.
When we finished eating, we paid the bill and began walking back toward his place and the PATH. We ran into a friend along the way, and Smiles chatted with him for a short while after barely introducing me. After we left the friend, he explained who he was and how close a friend he is. I was a little surprised. If he was such a good friend, then why was he so casual when introducing me. Maybe I didn’t mean as much to him as he did to me. Maybe I was putting too much of myself out there too soon. We’d been dating for a month and a half. I thought we’d be closer knit at this point, but maybe I was wrong. Maybe I had different expectations.
The Principal and I continued to text over the next hour while I watched some TV. I explained to him I still had some feelings for him, however, the distance thing just wouldn’t work out for me. Apparently, I opened up a can of worms there. He really did miss me. I’m not sure why I felt the need to reach out to the Prinicpal that night. I thought I passed that chapter in the story. I think I did it for selfish reasons because I needed to feel wanted again. I knew the Principal would provide that for me. Looking back, I never should have done that.At the ripe age of 26, I came to a life changing conclusion. I'm GAY!
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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