Posts Tagged awkward date

Valentine’s Letdown

Valentine’s Day had arrived. I managed to find myself single once again. I have yet to celebrate a Valentine’s Day. The one year it came while I was dating Broadway, we couldn’t be together because I got shipped off for work to the Midwest.

I ended my intense weeklong relationship with PR just the night before. I knew it was bad form to stick to our plans to go out for a romantic evening if I was just going to be faking it.

Just because I wasn’t going out for a romantic dinner doesn’t mean I wasn’t looking forward to the company of a man. For some unknown reason, I was exceptionally horny that day. Granted this has become the norm, and I’m starting to wonder if I may have a problem. However, I wasn’t stopping myself from exploring possibilities that day. I was single and ready to mingle.

I was all over Grindr and even pulled up the OKCupid app to see who was around my area. When this produced little results, I began to filter through all my previous Grindr, Adam4dam.com, OKCupid, and Manhunt contacts to see if there maybe something I missed or someone I wanted to revisit.

I messaged a few guys and asked what they were up to. The ones who I hadn’t spoken to in quite a while I asked how they’d been since we last spoke.

One guy hit me up on Grindr. I was pretty horny, so I wasn’t being picky. He was just offering to come over and give me a blowj*b.  I at the very least had a fallback. I was really looking to get it in, but I would settle for him if no candidates produced themselves.

I wasn’t happy with who I was becoming. Once again, I was letting myself get out of control. I needed to reign in my sex life, but that day, I just wanted to get it in. Tomorrow is another day.

I started chatting with the guy I’d gone on an awkward date with. We’d already talked about trying to figure something out about getting together again. I could tell he was more interested in sex than a relationship, but there was also still a glimmer of hope there for something to bud. I don’t claim to be a pro in the bedroom, but I do think, based on previous feedback, I am pretty damn good between the sheets. Maybe I could win him over that way.

We went back and forth for some time about him coming over. He wanted to go to the gym and hadn’t left work yet. Apparently I didn’t give him enough notice, but I could tell he was very interested. We talked about the logistics, and I made some great progress imploring him to come over. He told me he’d try to get his errands done and then he’d be in touch.

In the meantime, I had the blowjob on hold. I told him I had some work to do, and I would get back to him. He wasn’t thrilled, but he accepted my proposal of postponement. I told him I’d reach out to him as soon as I finished my work.

Finally, I got a text message. It appeared we were going to have our “second date” after all. He was wrapping up a few things and then he’d be over. He informed me he was bringing his c*ckring and poppers. I told him that was fine, but I wouldn’t be partaking in the poppers.

I immediately hopped in the shower to clean up, shave and prep for his arrival. I also opened a bottle of wine so we could relax before just jumping in the sack. I wanted to seduce him a little.

When he arrived, he was slightly awkward. I poured him a glass of wine and we sat on the couch chatting and drinking. When I felt the moment was right, I made a move. I was all but on his lap kissing him. And that’s when I learned why he was still single.

He was the worst kisser I’d ever been with. I thought he was going to eat my face. All that time I spent staring longingly at his lips, and that’s how he chose to use them. It was a very sad Valentine’s Day. I tried to soldier on past it. I tried to lead him and make-do the best I could.

Finally, I stood up to take a break, took him by the hand and led him to my bedroom. We slowly undressed each other. I was enjoying peeling his clothes off one by one. As I did, I was groping his entire body. He had a very sexy body and great skin. I couldn’t stop feeling him up.

Warning: The following may be too graphic for some. We laid head to toe and began orally pleasing each other. Eventually, he stopped to put on his c*ckring and grab his poppers from his jeans pocket.

When he came back to the bed, I began orally pleasing his bottom. He had a great a$s and manscaped very well. I was enjoying myself, but it didn’t seem I was doing the best job for him. That’s when I learned he doesn’t really get anything out of it, he told me apologetically. I didn’t understand because long ago he told me he was a bottom. I also recalled how much stimulation he got from his nipples, so I concentrated on them. He went wild.

A short time later, we laid next to each other stimulating ourselves. It didn’t take long before I finished all over his chest per his request. For once it didn’t take me forever to climax. As soon as I finished, he too exploded on his chest.

After giving him a towel and we both cleaned up, we laid next to each other in bed. I wanted to cuddle, but he didn’t seem the type to I just put my hand on his inner thigh. We chatted about the most random things. He was staring at my bookcase, and we talked about some of the books on the shelf. I pointed out my only gay book on the shelf, Beaches. It’s a picture book I like to page through periodically. He told me all the gay books on his bookshelf deal with barebacking. A huge red flag went off in my brain! Was he into barebacking? I didn’t ask him to elaborate, but I wish I did.

That’s when I hopped on his back and began to give him a massage. I have very large and very strong hands. I like to put them to good use. Apparently he was a little more delicate that I anticipated. He asked me to lighten up a bit, but he was enjoying what I was doing. I noticed how he analyzed everything. He really was a headshrinker.

When I stopped, he started inspecting my skin. I recalled on our date how he wished he was a dermatologist. He was very complimentary of my skin and complexion. I appreciated the compliment, but the delivery was incredibly awkward. He was not an easygoing guy, and I started to realize how little I was attracted to him. On top of that, I was starting to get an irritation on my neck from where he was trying to eat it. I knew then this would not be a repeat offender.

With that, he got dressed, collected his things, and we said goodbye at the door. He left very unceremoniously. I had no plans to reach out to him again after that. We’d had such a long history, making it weird, but we’d only really known each other a short while. He too had no plans to reach out to me.

Ironically enough, he messaged me on Grindr the other night, but of course this went nowhere.

Now, the only question is when and if I unfriend him on Facebook and what are the consequences?

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My California King

Things were going well for PR and I. He was turning out to be a great guy.

He’d been out with my friends and fit in. We’d had fun in the bedroom, and living room for that matter. I still had yet to meet any of his friends, but so far I was liking where things were going.

One evening after work, we made plans to finally go see The Woman in Black in the city. We both shared an interest in horror/scary movies, so I agreed. It sounded like a nice date too. I was sure it would involve some intimate hand holding in the theater and a nice night on the town for us.

I stayed at work killing time by writing a few blog posts until the time came to go to the movies. We agreed to meet in midtown by the PATH station and walk to the theater together. I didn’t hear from him for quite some time. It was getting very close to showtime, and I was getting annoyed. Why wasn’t he answering me? We were going to miss the movie.

Finally, I got a call from him. I met him on the street after learning he’d already started walking towards the theater. When I met him, I informed him we missed the movie. We needed to go to a different theater or find somewhere to grab a bite before the next showtime. He was very apologetic, but I was okay with everything. I didn’t have a schedule for the evening. I was just happy to be spending it with him.

We altered our plans and started walking to the theater on 42nd street. This would work out well because we could just hop on the bus at Port Authority to head back to Hoboken after the movie.

PR tried to pay for my ticket, which I thought was very sweet of him, especially since he was just working part-time until he found a full-time position. I thanked him for offering as I put my own credit card into the ticket vending machine to buy my own ticket. He tried to fight me, but it was no use.

We grabbed a big bag of popcorn and sodas and found our seats. I enjoyed holding his hand or rubbing his arm while we watched the movie. He was an affectionate guy like me. I liked that we were a match in that department. I was falling for him pretty fast, and we were spending a lot of time together over a short period of time.

The movie was decent. I don’t know that I would have picked it, but I was entertained and was happy to be out with PR.

We decided to grab dinner back in Hoboken. PR had only lived there a short period of time. He was anxious to get a lay of the land, so I suggested a few places we could hit up along the way. We settled on It’s Greek to Me and rode the bus through the Lincoln Tunnel. We hopped off the bus at our stop and went into a convenient store to grab a bottle of wine to take to the restaurant.

We sat at a table and decided on our meals. I insisted he try my favorite appetizer there, saganaki cheese. It was perfect with the wine we bought. I was really enjoying a casual night with him. The conversation was so relaxed and easy. We’d already gotten well past the awkward date stage. I was happy to just sit there with him at times, not even talking.

After we split the bill, we made our way home. We chatted more while we walked, and when we got to the intersection between our apartments, he was ready to say goodbye. I questioned him, and asked, “Aren’t you going to spend the night?” He replied immediately, “Do you want me to?” To which I confirmed and pulled him towards my apartment immediately. He asked if my roommates were home, but I told him that wouldn’t matter. They were cool and had people over all the time. He had no worries.

He’d forgotten to call his sisters to wish them a happy birthday, so he made a few phone calls to them while I answered a few emails and checked up on the blog. We relaxed on the couch for a little bit before making moves to the bedroom to go to bed. We watched Archer and Chelsea Lately in bed together, and laughed at all the same parts. It was nice to just sit and watch TV with a man.

When a commercial break came, I asked him what his “roommate” thought about him not being home all the time lately. “I told him I’m sleeping in a cute guy’s California King bed,” he quipped. I laughed and joked with him: “Is that all I am to you — A comfy bed?” He laughed and kissed me to show the contrary. Shortly thereafter, we dozed off and went to bed.

When my alarm went off in the morning to get ready for work, I looked back to the bed and smiled. I was happy to be waking up next to him. Of course I hopped back into bed and started to get a little frisky, but that wouldn’t make me late for work. I planned ahead and set the alarm a few minutes early.

I always leave room for play time…

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Last Minute Regrets

After my awkward date with Smiles, I felt I needed some change. The date was uncomfortable and the goodbye was lack luster.

Two guys had been reaching out to me on OKCupid, so I took the time to respond to them and try to set up a time to grab drinks. I shot them a text to see if they was available the following evening.

One of them, a guy who happened to go to the same college as me, responded informing me Wednesdays were the only day during the week that really worked for him. He was taking graduate courses, so he was quite busy.

The other guy texted me back to explain he was most likely available to meet for a drink when he finished work, but was unsure when that would be. He is a financial planner, so his hours are somewhat sporadic. We planned to touch base again at 5:00 the next day.

I had a lot of regret after setting up this date, but I tried to proceed with an open mind. All my friends encouraged me to date more people and not put all my eggs in one basket. I was finally following their advice. Smiles wasn’t exactly being the warmest towards me, so no harm, no foul.

When 5:00 arrived, the regret came flooding in. I didn’t want to meet up for drinks. I felt like I was cheating on Smiles. The planner sent me a text explaining he would be working late. He asked if I could meet for coffee at 9:30. I agreed, and sat with my guilt. It was already bothering me, and I didn’t even go out for the drinks yet. What if he tried to kiss me? What if he really liked me? What if I really liked him? This just goes to show you shouldn’t make quick irrational decisions.

As it got later, I got more nervous about the date. Not because of the date, but because of what it would mean for Smiles and I. I didn’t want to betray him. We hadn’t talked about exclusivity yet, but I was hoping we were moving in that direction.

I received a text that calmed my nerves completely. He had to cancel because he got called back into work. I was off the hook. I’m very grateful he cancelled on me, because the guilt would have really gotten to me. It’s just who I am.

I began to examine my relationship with Smiles. There were times he was completely affectionate and a total sweetheart. He really made me happy during those times. Probably far more than he realizes. I really enjoyed spending time with him, no matter what we were doing. On the other hand, when he would ignore me or not take me into consideration, I felt like such a small man. It really hurt to feel he wasn’t feeling about me the same way I was feeling about him. I wanted him to adore me the way I adored him at times. I felt like he always kept me at a safe distance. Not so far that I leave him, but not too close that I could ever hurt him. If we were going to proceed together, he was going to have to make himself more vulnerable and let me in.

I felt like I was part of his second life. He had his friends and acted one way with them, but when he was with me, he was different. He never integrated the two lives. Always separate. This is the reason I broke up with Broadway.

All this also helped me realize I needed Boston back in my life to talk me out of these crazy ideas. He is my sanity. I let my mind run wild after one bad date. He was always someone who could put me back on track and give me a strong dose of reality, not what my mind was conjuring up. However, he isn’t the easiest to get ahold of since he’s in he final year of school.

Smiles wasn’t talking to me much, so I would wait until he felt the need to talk to me. I didn’t go on the date, but I wasn’t exactly running back into Smiles’ arms. I was going to play hard to get a little bit…

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