Check That Off the List

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.

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  1. #1 by VpO on April 24, 2012 - 3:05 PM

    I had a threesome once when I was drunk . . .wasn’t planned. And like you said, it’s really hard to keep everything going. They make it look so easy in porn! Probably something I wouldn’t do again.
    And tell those who are judging to piss off. Everyone was safe and no one was hurt in any way. Some people just need to always judge.

    • #2 by One Gay at a Time on April 24, 2012 - 3:31 PM

      No one has started judging yet except myself, but thank you for standing up for me 🙂

  2. #3 by kinmanhattan on April 24, 2012 - 4:08 PM

    Hahaha, it’s a sign- 😛

    I suppose it’s a part of you that really wanted to explore it and since you’re “new”…. I’d imagine what you were thinking when it got awkward – it’s dare I say… a little cute? Lol. 😛

    • #4 by One Gay at a Time on April 24, 2012 - 4:28 PM

      LOL. These are the exact opposite responses I thought I’d be getting today…

      • #5 by kinmanhattan on April 24, 2012 - 4:41 PM

        Ha, want me to be more candid? Lol.

      • #6 by One Gay at a Time on April 24, 2012 - 5:01 PM

        Please… speak your mind!!

      • #7 by kinmanhattan on April 24, 2012 - 5:42 PM

        What happened to that romantic guy looking for love in the most exciting city in the world? Zip it up 😛 especially, when there’s not enough to go around, and shouldn’t you be taking a break on vacation? Like getting massages from your favorite readers? Getting “dirty” as you call it isn’t very vacation-like, is it? You could be out volunteering, where you’d meet the man of your dreams and then you’d settle down and then we’d write the blog together telling everyone of our miscellaneous adventures… Hahaha. I digress.

        I hope you don’t lose the romantic and loving man that you really are in quick, short-term resolutions and “dirty” misadventures. We care too much about you. Grindr is dangerous… and far too addicting. Don’t fit that negative stereotype…

      • #8 by One Gay at a Time on April 24, 2012 - 11:15 PM

        Sometimes we must stray from the path in order to find our way…

  3. #9 by theyoungplum on April 24, 2012 - 6:24 PM

    You can do who or what or how ever many you want.

    But in my humble opinion, the hottest part of that story is when you picked the guy up on your motorcycle. Damn.

    • #10 by theyoungplum on April 24, 2012 - 7:18 PM

      Also, technically today’s post consisted of two gays at a time.

      False advertising.

  4. #12 by PennStateGuy on April 24, 2012 - 10:47 PM

    I love the disclaimers. It should just say “ok here’s the good part” lol. And I kind of agree about the motorcycle thing.

    • #13 by One Gay at a Time on April 24, 2012 - 11:16 PM

      The disclaimers came about when my straight friend was caught off guard by some details he’d rather not read… But I enjoy that you find them to direct you to the “good parts”. 🙂

  5. #14 by superjaaho on April 25, 2012 - 11:06 AM

    I can’t help but agree with kinmanhattan a little bit. Although I don’t think there’s anything wrong with ’emotionless sex’ or a bit of sexual frivolity, it seems like you’re spending a lot of time looking for hook ups and I can’t help but wonder if it’s at the expense of the nice guys who want more. As kinmanhattan said, do some volunteer work, go read a book at a cafe, go for a run; you will no doubt run into a decent, single gay guy who’s perfect for you, sooner or later .
    I like what’s going on with Chelsea. You seem into him! And he is potentially what you want, right? So why not skip the randoms and threesomes and focus purely on him? At least until (a) you’re in a relationship with him, (b) you decide you don’t like him in that way, or (c) you find out he doesn’t like you that way. Otherwise the opportunity may pass you by because you’re too busy messing about on Grindr or whatever. You know?

    • #15 by One Gay at a Time on April 25, 2012 - 12:47 PM

      I agree with him as well. I have been getting out of control, and I’m never going to meet a man as long as I’m behaving in this manner.

  6. #16 by skinbycarrielorrain on April 25, 2012 - 11:13 AM

    this was very honest! None of that Hollywood Glam Feel-Good threesome saga. Life is messy and difficult and awkward. It takes time to get to know someone and have a level of intimacy that comes with trust and severe-like. Thank you for being honest about your experience and kudos to you for not sugar coating it for the readers OR yourself. I appreciate your maturity. Have an excellent day and I look forward to more of your brain.

    • #17 by One Gay at a Time on April 25, 2012 - 12:47 PM

      I try to keep everything I write honest. My hope is someone out there can relate and feel they are not alone. Thanks for your kind words!

      Feel free to subscribe on the homepage as well!

  7. #18 by barefoot_med_student on April 25, 2012 - 12:20 PM

    Is it weird that I find your blog interesting? And don’t mind the judge-y people, they need lives.

    • #19 by One Gay at a Time on April 25, 2012 - 12:46 PM

      Not weird at all! 😉 Glad to hear you’re enjoying it. I post weekdays. Feel free to subscribe on the homepage.

      No worries on the judgey people. I have thick skin.

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