Posts Tagged wrapped up

From Metropolis to Hoboken

On April 20th, my blog turned one year old. I didn’t even realize the milestone was coming up until I looked back at the calendar on a whim one day. I felt the need to celebrate, but I hadn’t told Clark Kent about my blog yet. How could I tell him I wanted to celebrate something I didn’t feel comfortable sharing with him yet?

Instead, I celebrated privately with messages from friends and readers on the blog and over social media. I also had a date night planned with CK.

I invited him to come out to Hoboken for an evening ride on the bike since we weren’t able to do so the previous Sunday. This would be the first time he came out to Hoboken and would see my place. I was quite excited. I came home for work early after a pitch and made sure my place was acceptable.

He had to work slightly later and had to swing by home before he came over. It was a Friday night, and he would be spending it in my bed. As time passed, I sat on the couch patiently awaiting his arrival as the clock ticked on. I had no word from him. I tried calling, but no answer. Where was he? What was he doing? What was taking so long?

Since I was a little broken from previous relationships, my mind began to get creative with where he may have been or what/who he may have been doing. Finally, I convinced myself to put those thoughts out of my head. They weren’t born of any behavior he exhibited. They were simply a spawn of his presence on Grindr. I needed to learn to trust again. The thoughts were gone, and all I could think about was seeing him.

He finally arrived in Hoboken around 8:00. I wanted to watch the sunset with him. The way it reflects off the city skyline is breathtaking, however, the sun had completely set. We’d be taking a ride in the dark.

I picked him up on the bike at the PATH, and we set off along the waterfront to the palisades of Weehawken. I wanted to show him a spectacular view while taking the bike out for a spin. He’d been so excited about it ever since he first learned of its existence.

I really relished having him ride behind me. He pulled himself in tight against me. It was incredibly romantic, and I loved how he wrapped his arms around me. I felt like a great protector.

When we got to the palisades, we parked the bike and took a short stroll along the cliff. We talked while hugging and kissing each other with the spectacular NYC skyline in our periphery. We happened upon a family taking pictures of each other with the city in the background. He offered to take the picture so everyone could get in the shot. I thought it was incredibly sweet of him, and I fell for him a little more at that moment. Every moment with him made me want him all the more. Again, I wouldn’t let myself get too wrapped up in him. It was still early. I didn’t even know if he was interested in a relationship, let alone one with me.

After taking the picture, I told him about my desire to prank tourists in NYC. I would offer to take a picture of them. Just as I was about to snap the picture, I would turn as if to run. When they began to chase after me, I would turn around and snap a picture. It would give them a great experience and a fun story to tell for the rest of their lives, and they’d have a picture to accompany it. He thought this was brilliant and commented on his desire to do this himself.

That’s also when I told him about my life’s to-do list. I told him I wanted to share it with him later because it spoke volumes about me.

We made our way back to the bike and decided to grab dinner back in Hoboken. I knew of a great spot everyone had been telling me to check out but had not been to yet, Bin 14. We rode down the hill from the palisade and made our way back to Hoboken along the river.

I found a spot to park, and we walked to the restaurant holding hands. I wasn’t yet comfortable doing this in Hoboken, but it was something I needed to get over. I would be gay for the rest of my life. If I wasn’t okay showing affection in public, I was in for a lot of headaches going forward. Since we didn’t have a reservation, they asked if we minded sitting outside. I preferred it actually. However, this posed a new situation for me again. We would be street side, and if I wanted to show affection, all of Hoboken could see — Or at least that’s how it felt.

Slowly but surely, I got over this. I was rubbing his knee under the table and exchanging kisses over our meal. I didn’t care who was looking. I still felt a little self-conscious, but I was proud of myself for getting over this.

After discussing wine at length, we agreed upon a nice bottle of Malbec. It took us some time to figure out how to order from the tapas like menu. We still hadn’t figured out our sharing dinner groove, but it was fun to learn this together. I came to find we shared a lot of the same tastes and likes. It also helped we were both share quite an adventurous palette. We ordered a few plates and told the waiter we would continue to order until we had our fill.

The food was great, and the conversation was even better. I was still getting to know him, and I was mesmerized by his smile the entire meal. I was gaga for this guy. If it turned out he wasn’t interested in pursuing a relationship with me, I was going to be heartbroken. I was past the point of protecting myself. I’d already cracked the candy shell. Now, I was in his hands.

We declined dessert, and I made sure to give the waiter my credit card to pay the bill before CK even had a chance to think about it. This date was going to be my treat. I liked this new system. With all the other guys I dated, we both threw down our credit cards and split everything. This felt more like dating and more like a relationship. Each date felt special because one of us was treating the other to it.

We hopped back on the bike and rode back to my apartment. When we got there, it was already fairly late, so we headed straight to my bedroom. I was just finishing removing my shoes when he shoved me backward onto my bed. Since it was up on risers, the bed shifted to the side and collapsed. He was so scared he’d broken my bed, but I assured him it was already an issue. This had already happened with N once before. I’d already been searching for a new sturdy bed not on risers, and this would be the impetus that forced me to address the issue with much more vigor.

We fixed the bed as best we could and continued to make out. It’d been a week since we were last together, so of course we were both horny for each other. I hadn’t had sex since we last saw each other, but I wasn’t sure I could say the same for him. We hadn’t crossed the monogamous relationship bridge yet, and I had no right to ask that question yet. We’d only been dating a week. One step at a time I told myself.

Warning: The following may be too graphic for some. Regardless, we found ourselves naked, and I was grinding on his backside. Our passion was elevated to a new level, and we were all over each other. I couldn’t get enough of his body — It was purely amazing. I’d never been with someone so handsome, so sexy, so fit, so sexual. He was like nothing I’d ever experienced before.

Eventually, he reached behind himself, grabbed hold of my manhood and directed it in until I found myself deep inside him. Amazing sex ensued until we both had our fill.

I was incredibly happy once again. I had a man who could come to dinner and hold a great conversation, and a man who could satisfy all my sexual desires. He was the best of both worlds.

With that, we cleaned up and climbed back into bed. I was happy to finally be sharing my bed with him. This would be the first time in a long time my California king was being put to good use. We fell asleep in each other’s arms. He was my little spoon. Throughout the night, we changed positions many times, but never fully woke up. We slept great.

When we woke in the morning, CK had to head back into the city to begin apartment hunting. He’d been putting it off and needed to put his nose to the grindstone. We stopped for a delightful breakfast at Ganache while we got to know more about each other. When we finished, we rode through the Lincoln tunnel into the city. I couldn’t drop him in front of his building because there was a parade going up his street, so we said goodbye to each other in front of the Empire State Building. I couldn’t think of a more romantic way to begin my Saturday…

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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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