The day after my birthday, CK and I made plans for me to meet his mother while she was in town. I celebrated my birthday the day before without him, but I still managed to have fun. I was incredibly excited to see him. I was also incredibly honored to meet his mother. I couldn’t believe he felt comfortable introducing me to her exactly one month from the date we first met, however, we’d grown extremely close in that short period of time.
There was a plan for me to meet CK, his mother, and three of his friends at Essex and Beauty on the Lower East Side for brunch. It was Mother’s Day, so I knew wherever we were going was going to be a sh*tshow! I was slightly anxious. I was more nervous about meeting the one friend I’d never met before than I was about his mother. I’m not sure why, but I didn’t feel any pressure there. I was pretty relaxed about it. Either way, I was missing my Superman terribly.
I arrived a few minutes late for our reservation. CK and his mother were still in transport, but the three friends had already sat at the table. One of them came to the front to greet me and take me to the table. I’d met him before when we all went to see Avengers together. As we ascended the staircase to our table, he informed me of a problem in the kitchen. He mentioned something about a leak and having to shut the kitchen down. There was new immediacy to our plans.
Per usual, CK was running quite late. I learned they were in a cab, but they were on the other side of Manhattan, however, he shared the good news he finally found a new apartment. It wasn’t in Brooklyn. It wasn’t on the Lower East Side. It was in Hell’s Kitchen. I was thrilled!!
We learned they wouldn’t arrive in time for us to order, and one of the friends began to protest in uproar. He argued with the staff until he learned of the true nature of the problem. The maître d’ offered to walk us over to their sister restaurant, The Stanton Social to ensure we got a table and were served quickly.
On the walk over, we happened upon CK and his mother getting out of their cab. He was in the process of calling me. I said hi to him and was introduced to his mother. She wasn’t what I expected at all. I’m not sure what my expectations were, but she certainly surpassed them. She was gorgeous and very lively. I immediately loved her spirit and energy.
We continued to the other restaurant. Not only did we get a table quickly, we were also served champagne to start. They more than made up for the inconvenience. On top of that, I feel we upgraded restaurants, not downgraded.
His mother took the time to hug all the other boys and say hi. She knew two of them from Miami, where CK grew up, so there was some catching up to do. CK was rather reserved in regards to PDA. We didn’t kiss, but I got a hefty hug. He whispered in my ear how much he missed me. We held hands under the table nearly the entire meal.
It was very nice being with everyone. The conversation flowed, and there was rarely an awkward moment. Our food was excellent, and we all enjoyed our meal. I was worried I’d feel like an outsider, not because his friends wouldn’t include me, but because they all already knew each other. I was the new guy. I didn’t know the stories. I didn’t know the inside jokes. That would take time. Generally, until I’m comfortable, I get quiet. I was worried they would think I was antisocial, which clearly isn’t the case.
If they hadn’t done enough to ensure we had a great experience, our lovely waitress brought us a plate of complimentary donuts to make up for what happened at Essex and Beauty.
I really loved watching CK and his mother interact. She had a nickname she called him, and I found it adorable. They shared a lot of the same mannerisms. I watched her keep him in line (and made sure I took mental notes). They were incredible together, even with the hell they went through over that weekend to find him a new apartment. It was obvious the copious amounts of love they shared.
When we exited the restaurant, his mother returned to go to the bathroom. He took the opportunity to pull me in and give me the biggest kiss. It was quite a scene, but we didn’t care. His friends made comments, and he pointed out how he wouldn’t kiss me in front of his mother. Apparently, it made her slightly uncomfortable when he “flaunted his homosexuality.” I thought this was funny, because it’s the kind of thing I could hear coming out of my mother’s mouth.
I also learned that when I went to the restroom while we were eating, his mother expressed her approval to him. “He’s really cute,” he told me she added.
When she came back outside, we made plans to go back to his place and spend the rest of the evening on his roof watching the sunset. We stopped for a bottle of wine and some beers and went up to the roof with the batch of cookies I baked for his mother. Before heading up to the roof, CK and one of his friends were talking in the kitchen. That left myself and his mother in his living room to chat. I learned about all her dogs, as well as CK’s dog all living under her care. She told me how early she had to get up to take care of them the morning she flew out. We talked about what it takes to raise a dog and discussed CK’s desire to get a dog. He was constantly trying to take me shopping for a dog, but I couldn’t take care of one on my own. I wouldn’t have a dog until I lived with someone who would help me raise it. Maybe CK could fill that roll one day.
We spent a lot of time talking about cooking. CK’s friend was an avid cook, so we had a lot to chat about. I showed him my massive digital cookbook I created. I learned where CK inherited his lack of cooking skills. Apparently, his mother was a self-admitted non-chef. She barely cooked, so the two of them discussed their lack of skill in the kitchen, however, each had their specialty they could cook. I expressed my plan to teach CK how to cook, but ensure he wouldn’t cut his finger off again under my supervision.
After a while, a guy CK used to hook up with who lived in the building joined us. CK privately made a comment to me when we were downstairs how he may have seen us all through the window. He mentioned inviting him to join us, and I didn’t protest. My guard was up however. I had no idea how he’d treat me. After all, I was the one who got the man he had a crush on. They were almost roommates until it came to light he had a crush on CK, who told me he did not share the same feelings.
In the end, this guy was pretty cool. He wasn’t combative toward me in the slightest, and we actually got along. The conversation continued through the night. When this guy left, CK made an attempt to set him up with the friend who joined us from brunch. I really liked this guy. He seemed to get it. He was very realistic and had a great sense of humor. Of the friends I’d met so far, he was the one I felt I would get along with the best. When the old hookup left, CK’s friend called him to set up a date. This also killed two birds with one bullet. The old hookup would be tied up and would stay away from my man. Yes, I was getting territorial.
CK’s mother told us stories about him when he was a child, and I was really enjoying getting to know him, his mother and his friends. It was starting to get late, and CK and his mother still needed to get dinner. I needed to get home and get ready for work the next day. I too needed to eat something other than cookies. I said goodbye to CK’s mother with a big hug and CK walked me to the door.
We talked about how much we couldn’t wait until his mother left, not because either of us were tired of her, but because we were hungry for each other. We hadn’t slept together in days, and our animal instincts were growling. I said goodbye to him with a big kiss and made my way to the PATH to head home.
It was a very successful weekend. I had a great birthday, and apparently, I was a hit with CK’s mother. The whole day was a big success. I was all the more excited to be a bigger part of CK’s life, and I couldn’t wait for the next moment.
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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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Wednesday night arrived. It was “date night” for San Francisco and I. We were meeting in the Castro to grab a drink and maybe some dinner together. It had been a while since I’d seen him last, and we were due for a catch up.
Since work was paying, and I was too lazy to learn the public transit system in San Francisco, I decided to take a cab. We arrive in The Castro neighborhood, and I witnessed the largest rainbow flag I’d ever seen in my life. The only thing I could compare it to (for the Americans in the room) is the giant American flags that adorn the poles in the parking lots of Perkins across the country. If you read my blog, you know how much I’m not a fan of the rainbow. However, I’m embarrassed to admit, the sheer size and presence of this thing actually made me a little proud.
I got out of the cab and met him on the street as we exchanged a hug and a kiss. We made our way to Badlands just up the street just in time for some happy hour specials. We caught up on the other’s dating life over the past few months. I learned San Francisco is currently casually dating someone. In the back of my mind, I’m very happy to hear this news. I didn’t want things to escalate beyond drinks for us, and this news was reassuring.
I told him the abbreviated story of Smiles and what I did on New Year’s Eve. He was a little surprised, but certainly didn’t judge.
As the alcohol flowed, his emotions escalated. He became much more affectionate, and even started to get a bit hot n’ heavy. I just went along with it. I had no emotions attached to these actions. I was fully over San Francisco. I tried changing the subject so he wouldn’t keep putting the moves on me.
He talked about the possibility of moving back to New York, but said it would be very different this time around. He’s a completely different person. Everything he was saying were basically the reasons why I ended things with him. It was as if he’d read the blog. (To my knowledge, he still does not know about the blog).
We started talking about his dream of opening a bar in Hawaii. We talked a great deal about even the smallest details in his dream. I suggested a name for his bar, and he immediately fell in love with it. He even went as far as to register the domain immediately from his BlackBerry. I told him how to do all this with my advertising background and knowledge and my recent experience of purchasing my own domain for this blog.
He then brought up the possibility of checking out a drag show that evening, but then he remembered it wasn’t my thing. Instead, he suggested we grab dinner at one of his favorite restaurants.
The meal was spectacular, and it wasn’t that expensive. I was also introduced to one of his friends who is a server there. As the night went on, San Francisco grew more and more inebriated. He wasn’t’ too much to handle yet, but he was drawing closer. He started growing louder and more indignant.
When the bill arrived, I think he thought I was going to take care of it. I think he thinks I have an unlimited expense account (which isn’t the case at all), when in reality I paid for his meal the last time I was out there because I wanted to thank him for hanging out with me that night. We split the check and made our way for the door.
The whole time, I was trying to send a pretty clear signal I wasn’t interested in hooking up that night. I was failing. He asked if we should go back to my hotel or hit up his apartment. Then he answered his own question when he realized how close to his place we were. Again, I just went with it. I’m not entirely sure why I didn’t just go home. I think I thought I could get him home and then say goodnight.
While we rode in a cab to his apartment, he asked me about the stuffed animals and orchids he sent me for my birthday. I explained that was over nine months ago. I was lucky I kept the orchids alive for six months. As far as the stuffed animals, I told him I gave the mistaken monkey away, but I still had the bear (of much more significance) at my parents’ house.
When we got to his place, I met his roommate for the first time. One had only seen me on Skype and heard lots about me, and the other had never met me. Ironically, the other share the same unique name as me and joined on as a roommate shortly following our breakup. I’m not going to lie; I thought it was a bit weird.
When we finished tormenting the roommates with S.F.’s drunken antics, we went into his room. It appeared I was spending the night. However, it was just going to be that. I was not having sex with him.
Of course the makeout session ensued. I thought to myself, “At least he’s a good kisser.” Then the makeout session morphed into more passionate actions, and I found myself with no clothes on. S.F. put me in a position to begin to penetrate me, but I wasn’t going to make it that easy for him. I kept casually squirming so it wouldn’t be possible. He kept gently trying, but I wasn’t going to give in. There was no way in hell I was going to have sex with him, but I also knew I was dealing with a drunk man. I gently whispered into his ear, “Let’s just spend the night together.”
With that, he rolled over into little spoon position. I curled up with him and went to bed. In the morning, when my alarm went off for me to head back to my hotel to go to work, I found myself with his mouth on my “morning excitement.” I had forgotten how good he is at that. It didn’t quite matter. I wasn’t in the mindset to finish with him, and we know how difficult that can be even when I am in the mindset.
I got dressed, and he remained in bed. I could tell he was disappointed, but I didn’t care. I was not going to revisit old territory.
I didn’t hear from him until much later the next day. He told me how hungover he was in the morning, proving to me how drunk he was. He asked what my plans were for the remainder of my trip, but we didn’t discuss meeting up again while I was there. I was happy to dodge that bullet.
I let things go further than I wanted, but at least I didn’t hurt his feelings too harshly in the meantime. In my mind things wouldn’t quite be the same for us going forward. No longer did I feel the urge to call him just to chat, which is sad. It appears I have collected what pieces of my heart I left in San Francisco…
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