Before my trip to Washington DC, I started chatting with a few guys on Grindr. It was bad timing for the trip to come right after “meeting” them, but it would have to do. On my way back home, I made plans with a few guys over text for dates to get to know them.
One of the guys I was talking to was a bit older. He seemed like a great guy, and he was very interested in me. Of all the guys I started talking to, he texted the most. He seemed sweet, caring and attentive. While away, he asked how the blossoms were. He genuinely took an interest in me. He was texting me like a high school girl. I wasn’t annoyed. I was flattered. We made plans to grab a drink Wednesday evening after work.
Since Southern Drawl didn’t want to go to The Breslin, I proposed he and I meet there for a drink. It wasn’t far from my office, and it was pretty centrally located in Manhattan. We set a time, and I stayed at the office to kill time until he could make it there.
He ended up arriving early, and he texted me to let me know. I quickly left my office and speed-walked the ten blocks to the bar to meet him.
I wasn’t sure what I’d be meeting that night. From his picture, he looked like a very mature man. He had white hair, and he told me he was possibly getting a haircut before we met. I encouraged him to keep his longer hair since I liked it, but it was his hair. I didn’t know which hairstyle I’d be meeting.
I walked in to find him standing leaning against the wall. It wasn’t too difficult to pick him out of the crowd, however, he looked much older than I originally expected. I invited him to follow me to the bar and ordered us drinks. I managed to snag two bar stools just as someone was getting up to walk away.
We dove right into conversation about work. We both worked in advertising at one point, so we discussed that for a while. The more we talked, the more relaxed the conversation became. I didn’t see this conversation growing into a relationship, but he was a really nice guy. There was no reason why I couldn’t share a few rounds with a nice guy. I really didn’t think we were compatible.
Somehow we got into philosophical conversation talking about life in general. He really liked my outlook on life. I wasn’t putting on a show or anything. I was just being myself. He really responded well to this.
During our conversation, he came clean on his age and informed me he was 36. That’s how old Smiles was, so it wasn’t the issue for me. He did, however, look more like he was 42. I wasn’t sure if I believed him about his age. I wondered if he was lowballing it.
We started talking about family and his family house in the Hamptons. We got on the topic of coming out, and I told him how fresh I was to the gay world. He responded well to this and told me he was new himself. He came out to a few of his high school friends, and apparently it didn’t go well. For them, it became a problem of an identity crisis. They didn’t know who he was anymore. I told him how positive my experience was coming out and conveyed my sympathy about his experience. He also told me his family didn’t know either. It appeared I was more gay mature than he was. This was a first. This was a 36 year-old man who was still living in the closet. I didn’t think I could handle that. If he couldn’t accept himself by that age, the road was only going to get rockier as we went along.
After three rounds, the time came to go home. He expressed his desire to go on a second date, and I let on that this was a possibility. I didn’t want to lead him on and seem overly zealous about it, but I didn’t want to break his spirit. We walked to the corner and said goodbye with a hug. We exchanged a few texts after that, but obviously nothing ever materialized.
It wasn’t that late, so I decided to text M.E. and see if he wanted to come over. He did, and when he arrived at my apartment, we immediately went to the bedroom. Warning: The following may be too graphic for some. We stripped each other naked and got right down to things. There was a bit of foreplay and a lot of making out before I reached for the condoms and lube. Since being with him, I had unprotected sex with someone else. I needed to keep his safety in mind. While in DC, my results came back with no STDs and HIV negative, but I didn’t want to take any chances. We had amazing protected sex that night and fell asleep in a spooning position.
When we woke in the morning, we fooled around until we hopped in the shower. There, we had sex once again. I’m always horny in the morning, so this was even better than the night before. When we finished showering, we went back to the bed and had sex there. At one point, I even turned over and let him penetrate me. I felt I owed it to him. He was incredibly excited about it. This didn’t last long because, as he told me, he had a hard time keeping an erection after he’d been penetrated. I was okay with this, being as it’d been a long time since I bottomed.
We laid with each other, and I tried to finish myself off but to no avail. I had a dentist appointment to get to that morning, so I could no longer dawdle. I was already late the way it was. This was going to be a rough day. How was I ever going to concentrate on anything!?
M.E. gave me a ride to the dentist, and I gave him a kiss goodbye.
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Today is another Fast Forward Friday!!!
Hope you are enjoying these. It will help bring the blog a little closer to real-time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!
Back to your special edition of One Gay At A Time…
Saturday had arrived, and it was St. Patty’s Day. I was out early in the morning to hit up the gym. I wasn’t going to find myself wasting another day lying around my apartment looking for sex. It was the true start to my staycation and to the new me. It was gorgeous outside, and I was motivated.
As I left the gym, I ran into K and one of my other friends. They were heading into the city to drink, but I wasn’t interested. I’d just come from the gym. I’m not a fan of day drinking to begin with. I said goodbye and continued on my way home. D’s girlfriend was up from Philly that weekend, so I texted them to see what they were up to. They were grabbing brunch and had no plans for the rest of the day. I told them I was bored and lonely, and if they thought of anything, I’d be game. I also called my old roommate to see what he was up to. He was studying for yet another test he had to take for work. I knew it was useless to try to convince him to do anything else.
Finally, D and his girlfriend decided to swing by. They came up, and we just lounged around chatting. She’d never been to my apartment before, so I showed her around. After some time, we decided to go for a drive and check some new cars for D to possibly lease. I was game, so we made our way uptown in the great weather to D’s car.
We decided to drive around Jersey City since there were a few nice neighborhoods I’d never explored. I was a bit curious, and the other two were as well. I also wanted to scope out a spot I had in mind for dinner that night with the guy I spoke to on the phone for two hours, Travel Agent. We drove by the cute cafe on the corner in an upscale neighborhood of Jersey City, The Hamilton Inn. I’d seen it a few times before and had been curious how it was. I pulled up the menu on my phone and suggested the idea to T.A.
He was still working, but he said it sounded like a good idea. We planned to work out the rest of the logistics later.
We drove around for quite a bit more before finally returning to Hoboken. They dropped me off at home. I hopped in the shower and began to get ready for the evening with T.A. I’d been texting him a bit and made a reservation at the restaurant for 7:00. When he told me it’d have to be later, I called and changed the reservation for 8:30. When the time came, he picked me up in his nice Audi. He was a good-looking guy. He wasn’t someone you’d stop on the street and say, “Damn!” but he was good-looking. We jumped right into conversation. It was fairly relaxed. I feel he may have been slightly uptight, but I tried to remain candid and relaxed.
The Hamilton was exactly what I was hoping for. It had a decent crowd, the food looked and smelled amazing, and we got a nice table to sit and chat with each other. The obvious and easy thing to decide was to order a bottle of Malbec to share. I still couldn’t help feeling he was uneasy about things. He just didn’t seem to relax. I tried to lighten things up and asked if he wanted to split an appetizer. He agreed, but it wasn’t terribly easy to pick something. He defaulted to me, and after discussing it, I finally decided on the pierogies with goat cheese appetizer.
We began by talking about where we grew up in more detail than we discussed on the phone. The conversation shifted to our jobs. I got to learn in greater detail what he does. I told him about my job, and slowly I began to realize I was monopolizing the conversation. He’d ask me a question, and I’d answer in detail. When I’d ask him questions, his answers would be short. I wanted to get to know him. He seemed like a decent guy.
The waiter returned and we ordered. I was debating between he risotto and chicken. I decided on the chicken, and he decided on the risotto.
We talked some more until our food arrived. Or should I say, I talked some more. I would never say it was a bad date, but I would also not say it was a great one either. We shared some of our meals with the other. It was a nice time. I was enjoying his company, and the food was delicious. I was looking forward to a second date so we could think of something more relaxed to do. Hopefully that would break him out of his shell.
We declined dessert since he had to get home because he had a big work project the following day. He expressed to me how much he enjoyed the date. I was happy to hear it. We split the tab and made our way back to his car. On the way back to my apartment, we passed another restaurant I was interested in trying. I mentioned it to him, and he said, “Maybe next time we should try there.” That was a very hopeful statement. If he was already thinking about next time, maybe he really did enjoy it too.
We stopped in front of my apartment, and he put the car in park. He leaned over and gave me a kiss. I pulled back and went in for a second. It was nice, and I wanted him to know I was interested. I told him, “Call me when you’re back from Mexico. Or, you can text/call whenever you like,” with a smile as I exited the car. He told me we’d be in touch.
After that, I heard nothing from him. He clearly stated his enjoyment and mentioned a second date. How was I not supposed to think he was interested? I sent him a text to tell him of my good time with him, but I got no response. I checked Grindr, and sure enough, he was online. Clearly he was ignoring me. I messaged him on Grindr as well. When a day passed and I heard nothing back, I decided he would either deny this or the “relationship” would be dead before it began. “I hope you’re not ignoring me. I thought you were a classier guy than that.” He had given me two different phone numbers, so I asked if I was texting the wrong number. Finally, he responds explaining he was busy and apologized. He told me he was interested in seeing me again as well.
However, after that, I didn’t hear from him again. I know when I’m not particularly interested in a guy, I don’t outright tell him that. However, I don’t talk to him about future dates to lead him on. It was very disappointing, but I wasn’t going to let one guy get me down. My Grindr diet was slowly working. I was back to concentrating on dates and not sex. Hopefully, with enough time, I’d find a good guy to settle down with — Someone to be the reason I delete Grindr forever…
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