Posts Tagged 36
Posted by One Gay at a Time in Gay Dating on May 18, 2012
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.Follow @onegayatatime
Posted by One Gay at a Time in Gay Dating on November 15, 2011
The official day arrived. Smiles was turning 36. He celebrated his birthday in conjunction with two friends a week earlier, which didn’t go so well for me. I wanted to rectify that situation.
I also wanted to dote on my new man for his birthday. I called him early in the afternoon to wish him a happy birthday and ask if I could take him out to lunch. The Ace Hotel is near my office and has two great restaurants and a bar adjoining it. Normally I’d let him choose, but I couldn’t wander too far from work on my lunch break.
I met him not far from the hotel on the street corner. I greeted him with a big ol’ kiss and a hug to say happy birthday. As we walked, he made comments about how casual my work attire was. He was under the impression people in advertising walked around in Mad Men suits all day. I explained how far off base he actually was.
As we walked, he reached down for my hand. I love it when he does that! We arrived at the first restaurant he chose, and after checking out the menus at John Dory, we decided to leave and hit up the other, The Breslin. I’d been there many times and absolutely love their lamb burger. I knew he’d be happier with the choice as well.
When the waiter asked if we’d like anything to drink, I declined, but encouraged Smiles to order a drink. He requested a dark and stormy. Without looking at the menu, I immediately knew what I wanted, and ironically enough, we both ordered the lamb burger. I also added another dark and stormy to the tab after seeing how refreshing his looked. Afterall, I work in advertising… It’s only natural to have a cocktail lunch, right?
Somehow the topic of conversation turned to religion. My mother was just telling me about a book a majority of my staunchly Catholic family read, Heaven is Real. We discussed the book and how we were brought up with religion. We even got as deep as to discuss our beliefs in a higher being. This is usually a risky subject for discussion, but the conversation remained casual and flowed while we ate. I think it actually brewed a stronger connection between us.
When the check came, I insisted on paying. He was pulling out his credit card, but I forced the server to walk away with just mine. There was no way in hell I was letting the birthday boy pay. “It’s your birthday. I told you I wanted to take you out to lunch for your birthday!” I exclaimed. After saying, “That’s an expensive birthday lunch. You really don’t have to,” he thanked me.
When we finished, he decided he wanted to grab a coffee. Since I met him, he has become addicted to the Starbucks salted caramel latte, or as he likes to call it, “his salty pretzel drink,” which I find adorable! While we waited for our concoctions to be made, he took the opportunity to lean his back against my chest. For me, the little things matter a lot. Those signs of affection really speak volumes. We got our coffees and walked towards my office a bit before saying goodbye. He was out of his downtown comfort zone, so I relished guiding him around to find a subway back home.
We said goodbye with a gentle kiss. I put him on the subway and made my way back to the office. Of course, I had a smile from ear to ear as I walked. It was a short encounter, but I was happy to get to see him. It was his birthday lunch, but I think I got more out of it than he did.Follow @onegayatatime