Posts Tagged charming

House Call with the Good Doctor

In a strike of luck, in terms of my desire to turn my dating/sex life around, the timing of a family trip could not have been better planned. My parents, my sister and I were heading to Virginia to visit my aunt, uncle and cousins. The purpose of the trip was to see the cherry blossoms in Washington DC.

It was a fun trip. I got to see my cousins’ girlfriends and their children, many of which for the first time. Even though the cherry blossoms had already fallen due to an early bloom, it was still nice to get away and relax.

While driving back to New Jersey with my sister, I began attempting to line up dates with all the guys I’d been talking to before I left. As far as going on dates, the trip came at a bad time because it put a roadblock in the momentum. I kept up with the texts from the southern boy I’d gone on one date with so far. We were trying to line up a second date, as well as a few first dates with some other men I’d chatted with.

I got back to town on a Monday afternoon and tried to dive right into the dating. One of the guys I’d been chatting with was a doctor I met on Grindr. We exchanged pictures. He was very good-looking, very well-spoken and very charming. His response to my picture was, “Matthew McConaughey party of one?!” I was incredibly flattered, and suggested he consult with an optometrist friend. Although he had some promise, I wasn’t all that excited to meet him. I was going in with an open mind, but the fact that he was a doctor was somewhat of a turnoff. He would have no time for me, and I have come to realize I need someone who will be around and spend time with me.

We texted back and forth to nail down plans. As the workday was ending, I asked him what he wanted to do. He responded, telling me, “I honestly feel like I need a quiet night in. A bit drained here but would definitely like to have you over for drinks and conversation if you are up for that?” It was a bit unconventional, but I told him I was game. He gave me his address, and we set a time at 9:00pm.

I made my way into the city, bottle of red wine in hand, and walked to his apartment. I called Boston, and he shocked me by picking up. I wanted to hear how his birthday went and catch up. He further shocked me with a story involving an on-duty officer and himself that made me so proud. It was nice to hear Boston letting loose.

As I walked up to his apartment, I hung up with Boston. He lived in a very nice building. He answered the door, and we exchanged hugs. He had a gorgeous place. I came in and made myself comfortable on the couch while he opened the bottle. I felt quite overdressed when I noticed him in sweatpants and a t-shirt. I was jealous. I removed my shoes and sat Indian-style on the couch.

He was far more attractive than his pictures. His tight t-shirt showed off his chiseled body, and his face and smile looked very similar to Taye Diggs. I was slightly mesmerized.

It wasn’t long after we began talking that he let his guard down. The flamboyance came bubbling up, and it was really turning me off. I immediately lost my attraction for him. I could see us being friends, but I could never date someone like that.

We sat on opposite ends the couch talking the whole time. I learned about his job and what he does in his free time (which wasn’t much since he didn’t have much of it). He told me his specialty, and that dominated a majority of the conversation from then on out. Ironically, his specialty was relevant to me, and we got on the topic of safe sex and HIV for over and hour. It was incredibly educational on two levels. I learned a few things about HIV transmission and the disease itself, and I learned how little I know about the stuff I was so cavalier about days prior. I thoroughly enjoyed our talk, but I wasn’t attracted to him as a potential man to date. I would, however, love to keep him around as a friend.

It was late, and I needed to go home. He needed to go to bed. He walked me to the door, and I said goodbye with a kiss. He pulled back and made a comment on how he wished he’d only done that sooner. He really liked it and came back in for more. He was a good kisser too. I walked to the PATH and then walked home, and it took me a while to get there.

The next morning I noticed a text from the doc. “Off to sleep here, but just wanted to say thanks for an awesome date! I really had a great time meeting you.” I apologized for my lack of response and told him I was at the allergist to getting poked with various things to find my allergies. We exchanged small talk on the subject, and the conversation fizzled out. That was the last I’ve heard from the good doctor…

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Stood Up Twice But Third Time’s a Charm

So much for getting things out of my system while in California. I was supposed to find myself while I was out there. I was supposed to calm down with the hookups. If anything, it had a converse reaction. Maybe it jump-started my libido. Since I arrived home, I had one meaningless one-night stand/hookup, and hooked up with a guy I could possibly considering seeing again. What was I, in college?

Wednesday at work, I was back to my old habits. I was all over Grindr searching for guys to go on dates with. The problem was none of them were looking for dates, so I decided to fill the time between dates with more hookups.

I hit up one of the guys in my favorite list, but he was really just interested in sex. We tried to make plans to meet up, but were having a hard time finding a location. He proposed an adult video store booth, but as you can imagine, I wasn’t onboard. He also wanted to go bareback, but I’d learned my lesson with that. No more taking those kinds of chances. When I tried to make more realistic plans, he flaked.

I started talking to one guy who was really hot. He wanted to hookup badly, but he needed time. He needed to prepare, which I can heavily respect, but he was also visiting. He needed to go out and get supplies to perform said preparation and needed to find poppers. It was pushing 6:00, and I wasn’t going to hang around the city any longer. He ended bailing on me, so I made my way home alone.

Two guys flaked on me; however, talking to them got me riled up. My libido was hungry. When did I become such a horn ball. After 25 years of basically no sex, you think I’d be fine going home with just my right hand.

I had an ace in the hole though. I texted the Middle Eastern guy from the pervious night and asked if he wanted to come over again. I don’t think I lifted my finger off the send button before I got a response back. He was certainly interested, but had to come over later after class. He wouldn’t arrive until around 10. That was fine. I figured out other things to do with my time, like eat dinner.

When he arrived, we went straight to my room, but I’m sure, much to your surprise, we didn’t immediately jump in the sack. We kissed for a bit, but then we simply laid next to each other cuddling while we watched Modern Family. We are both big fans!

Every time there was a commercial, he took the opportunity to kiss me passionately. There were no complaints from me. He was a great kisser. He had perfect lips and knew what he was doing. We also took the time to chat a bit. I wanted to get to know him a little. He lived with a bunch of guys in an apartment and even shared a room with a guy. None of them knew he was gay, and he recently broke up with a girl. He told me he’d been on a handful of Grindr meet-ups, but none were anything like what we shared. He told me how much he enjoyed the previous night and how much he thought about me all day long. It was very flattering, and a little alarming. This kid was falling for me — and fast. I needed to make sure things didn’t get out of control because I didn’t want to hurt him.

I couldn’t tell him what I was looking for because I didn’t know what I was looking for. I really wanted to find a boyfriend, but I wasn’t sure he fit the bill. This was new territory. I’d never dated anyone so much younger than me, let alone still in college. He was a really nice guy, and I could tell his friends loved him, but I was still conflicted. He was very mature, but nonetheless, he was still in school.

When the show was over, the making out led to heavy petting. Things escalated, and I invited him to spend the night. While naked, he walked to the bathroom to take out his contacts. I watched him from the bed, staring longingly at his body. I told him how hot I thought he was. He really riled me up. I loved the innocent confidence he exuded. It was incredibly sexy.

He told me he wanted to go to bed horny so we could wake in the morning and have some real fun. It was late, and I was tired, so I didn’t oppose. With that, he rolled into little spoon position, and I pressed my naked body against his in big spoon position. It felt so comfortable. It felt so right.

In the morning we both woke to the sound of my alarm — strategically set early to allow for time to play. We were both in a very frisky and playful mood. He certainly wasn’t shy about kissing. He loved it and did it often.

Warning: The following may be too graphic for some. While we embraced each other, he whispered in my ear how he wanted to ride me. I certainly was in no position to deny him this privilege. I was looking forward to it. I was shocked, him being so new, how much he was gung-ho about bottoming. I think he discovered he’s really a bottom. He hopped on, and it felt great. He came really close to finishing, but never did. I knew exactly what was happening, so I didn’t put any pressure on him or comment on it. That would only bring it to top of mind and make it worse.

He had to stop. He wanted to keep going, but told me he was sore. He informed me that I was a big guy. I’d never really thought of myself as big. I always thought of myself as average. But, as of late, I was informed otherwise. (This is not something that is important to me, but it is quite the ego boost to hear).

We laid next to each other once again pleasuring ourselves while he laid in the crook of my arm. I finished after a few minutes. I was happy things were turning around for me. It wasn’t taking a long time for me anymore. I was far from a one-minute man, but my mental block was easing. This wasn’t the case for Middle Eastern (will be called M.E. from now on). He never finished, but also never complained. He noted, “I can never [finish] after you’re inside me. I can’t explain it. It feels amazing, like a full body orgasm, but I just never shoot.” I knew exactly what he meant. I told him it’s just part of sex sometimes. I wanted to ease his mind.

With that, we both hopped in the shower, and I took the opportunity to wash him from head to toe with a bar of soap and my hands. It was really sexy and slightly romantic. We both enjoyed it. Then he did the same to me. It felt great!

While I get ready in front of the mirror, he noted its existence. He complimented me on what I was wearing to work. He really was charming and sexy. I was really starting to like this kid. I just worried we wouldn’t be able to have a real relationship. He was in the closet and in college. He told me he wasn’t hiding it anymore, but he was advertising it. I understood, but I just wasn’t sure if it was for me

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Postponed Plans

On Thursday afternoon, I made plans with Smiles to go out with him Friday night. We planned to grab dinner and then go out the bars for a night on the town finally. However, that plan would have to be postponed.

Thursday night, he sent me a text explaining he forgot he had dinner plans in Brooklyn and then a birthday gathering in the West Village. He quasi invited me, but added, “That’s probably not exactly what you meant when you said night out on the town,” he added.

I suggested we simply postpone our plans one night. It was still relatively early in our relationship, so some space can sometimes help. I didn’t want him to get tired of me. I would use the time to go out with my friends since I was spending many of my weekends with Smiles or traveling.

Friday, I went out in Hoboken with my friends. He texted me to tell me he got a new phone. I was thrilled to know he was thinking of me even though I wasn’t with him (Or, at least that is what was going through my head as I read it).

Saturday morning, I woke and was feeling very productive. For quite some time, I wanted to trek down to the Financial District to check out the Occupy Wall Street movement in Zuccotti Park. I wanted to take the nice camera from work with me to snap some cool shots of the protestors. I didn’t want to do this alone. It was something Smiles and I discussed many times. I tried texting him and then eventually called him to see if he would join me. He was doing work, so he wouldn’t be able to join me until later in the day.

Since I knew he was by his phone now, I sent him a sexy picture of myself from the summer with the caption, “Wanted you to have a sexy picture for your new phone.” He responded, “Haha. Love it!”

I tried a few of my other friends to see if they’d tag along, including LES. After much convincing, I was able to get him to join me, but under one condition. I had to come by his place to smoke first. I agreed and also proposed we use up my Groupon that was expiring that day.

When I finally got to LES’s place, we smoked and got on our way downtown in a cab. The sun was setting quickly, so I proposed we just grab something quick for lunch instead of using the Groupon.

We got downtown to the Occupy movement, and we began exploring. I took many pictures and was even approached by an editor from The Suit Magazine asking me to send her some of my shots. She was looking for pictures to use in an article.

After we had our fill of protestors, we made our way to Wall Street. While walking, LES said to me, “So what’s the deal with this other guy? How old is he? What does he do?” I knew exactly what that question was. I interpreted it to mean, “What does this guy have that I don’t? What makes him so special.” It was an awkward moment, but it was bound to come up at some point. I really liked Smiles, but I also really enjoyed LES’s friendship. I didn’t want to create too many waves or hurt anyone’s feelings. When we got to Wall Street, we found they were filming Batman, and we wanted to check it out. By the time we got there, they were cleaning up the “set.”

As I was walking LES home, Smiles called. He finished work and was ready for dinner. I wanted to go home, shower, change and drop off the camera before we went out. I told him I would meet him for dinner later, and we made plans. I felt very guilty having that phone call with LES walking next to me.

After I cleaned up and changed, I met Smiles in Chelsea for dinner. We had no location picked out, and ended settling on Elmo for dinner. Conversation during dinner was great. He had a very productive work day, and I feel he let me in even more. He was opening up more and more every time I saw him. We were finally peeling back the layers of that onion.

After dinner, he proposed we go over to Barracuda. I’d never been and have always been leery of it. I’m not a fan of gay bars. They make me uncomfortable.

When we arrived, I learned he knew two of the bartenders. I had met them before as well. They were both very good-looking and pretty unforgettable. They were at Smiles’ birthday gathering. Barracuda wasn’t anything like what I expected. I was expecting a flashy club like seen, not a dive bar. I immediately felt more comfortable.

That is until a tall overly friendly black man came up behind me and started feeling up my chest with his arms around me. He was a feisty one, and I wasn’t interested. I made that pretty clear by my extremely uncomfortable facial expression. Smiles on the other hand was playing ball. I assumed it was a friend of his, until I learned he never met the guy before. This was just Smiles being his charming self.

Because I wasn’t completely comfortable, I drank a little more excessively than I should have. On top of that, Smiles’ ex arrived. I had no problem meeting him and talking to him, but I did have a problem when Smiles said to me, “I hope you don’t mind, but I’m going to steal away with [him] for a minute. I haven’t seen him in a while, and I need to chat about some things.” Based on the interaction, I wasn’t worried that he was going to do something with his ex. I was more annoyed I was being ignored in a place I’d never been before where I wasn’t completely comfortable and knew no one else.

I entertained myself by watching the bartenders cutting off the tall black man because he was being obnoxious to everyone at the bar. However, for me, the drinking continued — In excess! I drank so much, the bartender started giving me free drinks. I drank my face off. I was hurt and p*ssed. This little chat went on for a long time. There was some flirting and maybe Smiles wasn’t 100% over him, but I was okay with that. It’s natural. I wasn’t okay with being ignored! When the conversation ended, Smiles said to me, “How come you’re so quiet?” What the hell was I supposed to say to that? — “I’m quiet because you just ignored me for the past half hour?”

Next thing I know, when I woke up in his bed, the first thing I noticed was I was naked. I never sleep naked. The second thing I noticed was some lube on my backside. I couldn’t for the life of me remember anything about the night before. I don’t remember much after that. I don’t remember getting my coat from coat check. I don’t know how we got back to his apartment. I don’t remember climbing into bed.

I racked my brain to remember anything from the night before. The only thing I could conjure up was a flash of about ten seconds of sex with him on top of me. It was a very scary feeling! I’d blacked out before, but never have I blacked out sex. I was the only one ordering my drinks all night, but I couldn’t 100% rule out the possibility someone roofied one of my drinks.

I never mentioned to Smiles my panicky thoughts. There is no chance in hell Smiles would have done that to me, so I wasn’t worried in that respect. I knew he would never take advantage of me. I was probably pretty lucid in my drunken state, if previous history has anything to say. I was worried I may have done something to embarrass myself. I decided to play it cool and pay close attention to how the rest of the morning progressed…

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A Night at the Opera

After what I deemed somewhat of a failure night, Smile‘s birthday gathering, I wasn’t exactly feeling positive (I’m told by some readers they were depressed after yesterday’s post as well). However, I wasn’t giving up or accepting defeat. I chalked it up to an off nights.

Ayawaska Root

For the rest of the week, I didn’t reach out to him. I wanted to see if he’d reach out to me. Surprisingly enough, Smiles texted Friday afternoon. Maybe my friends were right. Maybe I was right to lay low and let him come to me. I hadn’t sent a message or made a phone call since I left him Wednesday night. He wrote, “How’s your Friday going?” I told him it was going well and inquired about his cleanse. We texted a bit before I jumped on the opportunity to confirm our plans to go to the Metropolitan Opera that Saturday.

I wrote, “Looking forward to seeing you tom night btw! Call me when you get a free minute so we can discuss details before you go comatose on me…”

He immediately called to clarify. We discussed the timing of his Ayawaska ceremony and the timing of the opera.

I remembered from our conversation earlier in the week, tickets were to Barber Saville. I went online and did some research. I’d never been to the opera before, so I didn’t want to look like a schmuck. In doing my research, I realized his timing of the show was off. “Is this Il Barbiere di Siviglia at the Metropolitan Opera? If so, it looks like it’s at 1:00 tom…” I texted him.

I received a troubling response: “What. OMG! EEK! Let me look…” “Houston, we may have a problem!” I responded, “I gathered.”

He eventually called me back to offer a few possible solutions. He didn’t think he was going to be able to make the opera by 1:00 after being up all night, so the first was to give me the tickets, and I take someone else. The next was he gives the tickets to a friend if I don’t want them. I said, “Well obviously my first choice is to go with you. You don’t think you’re going to be able to make it?” He paused a moment, and responded, “Let me make a few phone calls to see how I’m going to be after this. Who knows? Maybe I’ll be wide awake and energized.” He hung up.

After about a half hour, he called back. He talked to someone who’d done it before, and they told him they weren’t sure how he’d feel afterwards, but it was quite possible he would be alert and want to go. They told him not to cancel his plans. So, our new plan was no plan. We were going to play it by ear.

That night around 8:00 I sent him a text saying, “Have fun tonight, and be safe ;).” I got a response at 4:16am. “Home safe. Should be good tomorrow. Home at 4am. Call you about 11.” It was a very happy text message to wake up to. I was thrilled. After thinking we wouldn’t get to go, I once again got excited about the date. No man has ever taken me to the opera before.

At 11:00, he called, and we discussed attire. We thought about grabbing brunch for a hot second until we realized we’d be late if we did. I came into the city, and we hopped on the subway up to Lincoln Center. We first grabbed the tickets, and then, instead of brunch, we settled on coffee at Starbucks.

We made our way back to the opera house and found our seats. We had great orchestra seats, but to get to them, this involved sneaking past a full row of elderly folks. As Smiles was passing one elderly fellow who didn’t stand for him to pass, the man got overly excited about someone passing in front of him and began to make a fuss asking Smiles to wait for him to stand. In the meantime, the elderly man began to have a coughing fit followed by apologizes for the next ten minutes. I was thrilled there was at least one seat between myself and this man. That is, until the show was about to begin, and he wanted a better view and scooted over – still coughing, still apologizing.

He wasn’t even there after a few minutes in my mind. I started to chat with Smiles. He was talking about a work project and the subject of his mother came up. Mid-story about her, he stopped and said, “Well, you’ll see if you ever get to meet her.” I was back on track! The fact that he was even entertaining the idea of me ever meeting his mother thrilled me! I was on cloud nine.

On top of that, he reached out his hand as the show began to hold mine. The birthday party night was well behind me. I now had a clear signal he was indeed interested in me. I could have melted into a puddle right there (it’s the little things for me obviously).

When intermission came, I had no idea everyone leaves the theater. We went outside and grabbed water at a nearby cafe. It was a gorgeous day, so we sat in the sun a minute commenting on all passersby. When it was time, we went back into the theater and watched the remainder of the opera. I was elated. It was a good show. I would definitely go back again, but it’s more of a once a year thing, whereas Broadway is a few times a year thing. But, that wasn’t even what was making me so happy. I had a permanent smile.

Afterwards, we decided to grab early dinner. We crossed the street to hit up a sushi restaurant, only to find it closed. We settled on Cafe Fiorello’s next door. When the waitress approached, Smiles asked her what her name is and began chatting her up. This is something I noticed he does everywhere we go. I find it very attractive. However, if I didn’t know any better, I’d say he was flirting with her (he did used to date women as well). She was eating it up. Neither was a bad thing. I wasn’t off-put at all.

We shared a nice half bottle of white wine and ordered our food. When the waitress returned to tell me they no longer had any lamb in the restaurant, I ordered my second choice. Smiles cut in and said, “You should inform the maître d’ we are outraged there is no lamb, and he should give us another half bottle of wine.” She replied, “Since you guys are so great, I’ll see what I can do.” After she left, I commented on how I was impressed by his effort.

When she came back to check on us, she said, “He said no to the bottle of wine, but I’m there’s something I can do for you instead.” He again thanked her with his charming smile. I said, “We’ll prob get a free desert or something.” He noted, “Oh, we’ll get something. You’ll learn I don’t give up. This is fun for me.”

Shortly thereafter, she returned with two glasses of champagne for us. I was duly impressed. He was a smooth talker. He really worked his magic. With that, we cheers to actually making it to the opera.

We were our waitress’ last table, so we closed our check so she could cut out. “You guys are my favorite table of the day. I love you guys!” she exclaimed. Although he argued against it, I picked up the tab since he provided the opera tickets. As I forced my card into the waitresses hand and told her to scram before he could get his out, he appreciated the gesture. As we were finishing our champagne, Smiles pulled out his phone and was looking for something. I asked him what he was trying to find. He noted there was a store in the neighborhood he wanted to stop in. I asked which because I was decently familiar with the neighborhood. He wouldn’t tell me. It was a big secret. I love surprises, so I didn’t push the issue.

We began to walk up the street. I had no idea what was coming next or where we were headed since he was being secretive, but I had a feeling I was going to like it. But, that’s another post for another day…

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