Posts Tagged flat tire

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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Where’d He Go?

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…

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