Posts Tagged upbringing

Is This Really Working?

Since my last date with Southern Drawl, he had been bothering me for another date. I was trying to take things slow with him. I wasn’t gaga for him by any means. He was growing on me a little, but he still left a lot to be desired.

We made plans to make plans after work Tuesday evening. I left work when he was about finished after trying to bang out a blog entry and made my way downtown to his office. I waited for him on the street corner to finish work for about ten minutes when it began to drizzle. I had not expected rain at all and had no umbrella. I was growing impatient. I called him, but he didn’t answer. Finally, I noticed him walking up to me at a very slow pace with his headphones attached to his phone.

Normally, I would greet someone I’d gone on this many dates with a kiss, but not him. He was too self-conscious. He was not out and was not comfortable with public displays of affection. This bothered me. I needed someone who could love himself enough to not care about everyone else.

We decided to walk downtown on the High Line. I climbed the stairs, and he walked behind me. We took a nice stroll south to find a place to grab dinner. We didn’t have a place in mind, but we had a neighborhood — the West Village. We talked about our days while we walked. Once again, he made a crack, and I didn’t respond well. It was always hard to gauge his sense of humor. We never seemed to be on the same page. If I joked back, he would tell me I was getting defensive and loud. It was insulting. He obviously didn’t get my sarcastic sense of humor.

When we reached the end of the High Line, we descended the stairwell and walked to find food. We passed more than a few places that looked good, but they didn’t have any available tables. They were either too crowded or they appeared non-desirable. We finally came to Frankies 570. I had been there, and the food is amazing. I hesitated going there for a solid second because I already had memories with Smiles there. We shared a really nice meal there one night after work. Then I thought about it, and it made more sense for me to expunge those memories. I could overwrite them with new ones. I didn’t exactly have positive associations with him. I felt used by him as a meal companion.

I suggested it to S.D., and we perused menu before going in. He agreed on the spot and was seated by the front widow at a nice table for two. We ordered drinks and chatted casually. It was nice to sit and relax and just talk about things and my day. We discussed his coming trip home. He was very excited. This would be the last time I saw him before he left. He told me he’d be sending me a lot of pictures from home and would call periodically.

Throughout dinner, he was much more demur than usual. There were no overtly sexual comments and no innuendoes. It was kinda nice. He asked a lot of questions as well. Usually, he was just talking away. It was nice to talk about our upbringings and his home, however, his sense of entitlement was still shining through. He spoke about politics and slavery. He told me stories of his family and how they basically still had slaves. He certainly wasn’t winning me over. I was never all that thrilled with the South’s way of doing things, and he was certainly perpetuating the stereotype in my mind. I also learned how important money is to him, and it was a real turnoff.

Slowly but surely, I was realizing this guy really wasn’t right for me. We had so little in common. I was simply enamored by someone paying attention to me and being interested in me. We were in a downward spiral.

On the positive side, my meal was spectacular. I ordered the rabbit ragu and enjoyed every bite. My drinks was pretty amazing as well.

When we finished eating, we sat there talking a bit more before heading out. When we finished our drinks, he accidentally spilled his water all over me. It was a bit humorous because we were just joking about it, and it embarrassed him immensely. The table next to us took notice of the large commotion this caused, as did the wait staff. We paid our tab and made our way out into the street.

He walked me to the corner to say goodbye. I could tell he was very uncomfortable. I was a block from the PATH and ready to head home. I was not going to a second location, and I was not going home with him. I think he was itching to hang out more, but I wasn’t interested. Just as I was about to go in for a kiss, he turned his head. I was partially p*ssed and partially happy. This was creating an out for me. I scoffed at him and began to walk across the street to go home. He chased me and stopped me on the other side of the street. I told him what he did was not cool at all. As he went in for a kiss, I played along, and at the last second, I too turned my head. Just then, a man was crossing the street and witnessed this. He began to chuckle to himself, and I pointed this out to S.D. He was embarrassed. It served him right. If he thought he had a chance with me, he’d have to sack up. I wasn’t about to date a closet case. I’d moved past that.

We said our goodbyes, and we finally did share a kiss. There was nothing magical. He was still self-conscious. He may have made a good friend, but I couldn’t see myself with him in a relationship. I finally came to see the light. I said goodnight and hailed him a cab. I put him in the cab and said goodbye. I wouldn’t see him for over a week. This would give time for things to settle and fizzle out. I wasn’t going to end things over the phone across state lines, but I wasn’t going to make myself available while he was gone.

After all, I was back out there searching for a real prospect. I needed a real man who could make me happy. I didn’t need to settle on a guy like this. I live in NYC. I fired up Grindr to check my messages on my walk home. There are great gay men everywhere. Now, they just needed to find me…

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Gray Hairs

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…

That night following my breakup with Smiles, I went home feeling some freedom. I’d already gone on a date and hooked up before breaking up with Smiles. But, now that it was official, I felt I could do whatever I wanted.

It’d been a while since I had some good, wild, crazy sex. I was horny. I had three months go by with only a little bit of lovin’ in the bedroom. I was hungry for a good man and a good time.

I was very cautious of history not repeating itself. I was not going to let myself go wild like I had after breaking things off with N. I didn’t need to do it now like I needed to do it then. But, that didn’t mean I couldn’t have a little fun.

I pulled out Grindr and began my talent search for the night. I wanted to find a good time one-night stand type. Any guy who wanted to hook up with me the first night he met me would not be a guy I wanted to date. Yes! That is exceptionally hypocritical of me, but it’s my love life, and I make the rules.

I found an old friend on Grindr while I was searching. He was a guy who came over to my apartment one rainy night shortly after breaking up with N. We were both staunch tops at the time, so we just fooled around a bit, but he had a great body and was a lot of fun. Even though we didn’t have penetration, we managed to find other creative ways to ensure the other fully enjoyed himself.

We chatted a bit, and he told me he missed me. I explained why I hadn’t been around as he told me he was hoping I’d hit him up again for a fun night. I told him to come by, and I would surely show him another good time. He tried to convince me to come to his place, but I insisted on hosting. I just felt more comfortable in my own bed.

He came by, and we laid in my bed just talking for a little bit. He had on many layers, and I slowly stripped a few off so he would be more comfortable while we laid there. Eventually, we started making out, and I rolled him on top of me.

Warning: The following may be too graphic for some: I stripped him down to his briefs and fully appreciated his body. He was an older gentleman, but he certainly kept in shape. Everything was still tight and sexy. I hoped I would be in such good shape when I was older. Ironically it was that night I learned he was in his last year of his forties. I had no idea he was so old. I was shocked in fact. It didn’t change the fact that he was a sexy specimen of a man, but it kinda flipped my mentality on end. Up until this point, I thought the forty-year-old was the oldest I’d been with. He looked a lot like Ulrich Alexander Fox.

Regardless, he had a great d*ck and an amazing ass. I was ready to have some fun. I recalled his position as a top only, so I knew there would be not penetration again, but ironically enough, he volunteered, “Maybe sometime I’ll let you inside me.”

I was completely caught off guard. I replied, “Really!? Why’s that?” “Because you’re sexy, and I really feel comfortable with you. Maybe some day.” I asked if he ever bottomed, and he told me it’d been many many years since he’d last done it. I felt privileged. I was getting the ego boost I needed to get me back on my feet. It couldn’t have come at a better time. Here was a guy who was looking forward to another romp in the sheets with me, and we’d never even had full intercourse. Maybe I was better in the sack than I gave myself credit for :).

I had a lot of fun with him that night. He went down on me, and I finished like a pro. He commented on how he wished he still got as hard as I did and was able to shoot like I can. I then, with jello legs, helped him finish as well. He certainly deserved that after the fun night I was having.

Afterwards, we laid next to each other and just talked for a while. It was then I learned he was actually black. I’d noticed he wasn’t a white guy, but I wasn’t sure what his background was. I had nothing against this at all. I’d just thought maybe he was of Middle Eastern descent or possibly Egyptian. I also learned he was adopted by what seemed like a picturesque white family in Connecticut. He was very happy explaining his upbringing. I could tell there was a lot of love in that family. I was happy I had a real man in my bed and not just a body to hook up with. I’d never start a relationship with him, but at least this friend with benefits was an interesting guy with a big heart.

He again told me how much he missed me and being with me. He also told me he hoped we could find time to meet up again in the future. He encouraged me to come to his place some time since he lived alone and had a nice apartment. I told him I would certainly come to him next time. I learned he really wasn’t a creep, but a decent guy with a decent libido.

I once again took the opportunity to admire his body and tell him how hot he is. He was embarrassed by my compliments and talked about his need to take more care of his body. I insisted it was pretty amazing, and he directed the attention toward mine. He told me in detail how hot I was and how thrilled he was to have fun with me.

We continued to talk as her got dressed. I walked him to the door and gave him a kiss goodnight.

It was exactly what I needed right when I needed it. I had fun. I got an ego boost. And, I had a smile on my face for at least the rest of the night. I would sleep a very happy man that night!

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Deep Pockets

Since deciding to end things with Smiles, I’d already been on one date and had one hookup. I certainly hit the ground running. I felt slightly guilty all this was going on before we even had the chance to formally end things, but then again, things never really formally began between us.

I wasn’t wasting any time either. I had been talking to a really nice guy on and set up a date to grab drinks with him after work Friday evening. It was a bit awkward because this was truly a blind date.

He had two pictures on a4a, but neither was clear and one didn’t include a face. When I asked him to send me a better face picture, he told me he didn’t like taking pictures of himself. Of course a red flag raised in my mind, but I had nothing to lose either. If I arrived and the guy was unacceptable, I was right next to the Port Authority bus terminal. I would be home in no time with little of my time wasted.

We agreed to grab drinks at Arriba Arriba in Hell’s Kitchen. It was conveniently located between his apartment and my office, and like I said, it wasn’t far from my transportation hub to go home.

As I left my office and began walking north, I was quite nervous. I’d never been on a true blind date before. I’d at least seen pictures of their faces, but this time I had no idea what he looked like. I joked with him, “Not gonna lie. Not sure what you look like… Haha.” It didn’t take him to respond: “Sorry mate. Don’t like taking pictures of myself. We will find each other… haha. You can ask me to leave once you see me and how ugly I am. Lol.” I didn’t care all that much at this point for the picture. I was already going in blind. I replied, “No apologies needed. Just tellin’ ya you’re gonna have to find me…”

I waited for him on the street corner. I put that time in a good location to good use. I surfed Grindr in HK for any new prospects. I know some may say that is classless considering I was waiting for a date, but I’m not in HK all that often anymore, and there is more talent in that neighborhood than where I work. He finally arrived and approached me. I asked how his trek to HK was, and we went inside to find a table.

When we learned we could only stand at  the bar since we weren’t ordering food, we decided to go elsewhere. I was at a bit of a loss because I hadn’t been in the neighborhood for some time. I didn’t know of a good place for us to go for a drink. Luckily, this guy was good on his feet. He suggested Eatery, and we were off.

We grabbed a seat at the bar and ordered a few rounds of drinks. We chatted for a long time about a myriad of things. The whole time, he kept his ball-cap on. Beyond the fact that he should know it’s bad manners, especially since he was an older gentleman, I was also worried there may be no hair under there. I’m not shallow, and looks are not everything to me. But, if he was balding without shaving his head, I wasn’t sure I could deal with that. (Smiles shaved his head and I was obviously okay with that).

We talked about our upbringings. He lived a bicoastal lifestyle, living in California and South Carolina. He also was shipped off to boarding school in Switzerland, where his grandparents lived. I grew up on a farm and went to public school. We had quite the education/socio-economic divide before. This is one thing I‘m not sure I am capable of getting past. I’m sure if it was the right guy, I could handle him coming from wealth, but it’s something that makes me quite uneasy. He came from money, and a lot of it.

I also learned he leads a very lavish lifestyle. He told me about his plans to purchase a house in Barcelona. He’d recently traveled there to scope out some places. He also told me about the $200,000.00 loan he gave a friend and was never paid back because the friend died and left his only possession, his apartment, to someone else. He told me about his lavish trips to the Caribbean islands recently. The list goes on.

Ironically enough, he wasn’t talking about all these because he was trying to impress me (Or at least it didn’t come off that way, which is fine). It simply came up in conversation or I coaxed them out with questions. I just felt uncomfortable with our socio-economic differences. I don’t really aspire to the position of kept man. I want someone who will share the financial burdens with me equally. I know a lot of people would love to find someone rich to marry, but money means very little to me when it comes to love. I think like I would constantly feel like less of a man if I had everything provided for me constantly, and I contributed far less to the relationship. Maybe this is something I will learn to get over in time, but for now, it makes me uneasy.

I learned how he continued to build his wealth and his professional relationship with a family in Canada. He told me about all the businesses he was involved in, and I started to worry he was another Smiles — Too much on his plate to commit to a real relationship. I also learned he wasn’t out to many people in his life, even after he’d been in a nine-year relationship with a man who left his wife for him. It ended when the man cheated on him while he was away on business. I wasn’t sure how I felt about him still being in the closet. He’d experienced too much and was far too old to still be in denial of his true self. I wasn’t sure I wanted a “project” at that age.

Drinks quickly turned into dinner. We stayed at the bar and made friends with the waitress. She was super sweet and very interested in chatting with us. Over our meal, we conversed more, and I learned we share a lot of the same morals and interests. We had similar outlooks in life.

He also became much more physical as the night progressed. He constantly had his hand on my leg rubbing my thighs and caressing the back of my knee. I started to do the same. Periodically, he would stand and give me a big ol’ bear hug. It was sweet. I liked knowing he was a passionate physical man. I needed that after Smiles constant distance.

Six hours later, we were ready to leave the bar. He decided to walk me to the bus. I thought when we exited the restaurant we’d exchange a kiss and go our separate ways. He was a true gentleman and walked me to the Port Authority. Not only that, but he walked me to my gate to wait for my bus and stood there waiting with me. It was midnight, and he was being a total sweetheart. He stood anxiously next to me as if he didn’t know what to do or how to close the date. He wasn’t really out, so I had a feeling a goodnight kiss in front of a large group of strangers was out of the question. When my bus arrived, he said goodbye and we agreed to be in touch.

As I rode home from the date, I wasn’t entirely sure what I thought of him. He became more attractive as the night went on, but I wasn’t sure if that was his personality or the alcohol stepping in for average looks.

I had a lot to think about. It was clear to me he was interested in me. The next day, he texted to see if I was interested in catching a movie that evening. I told him I had plans to hang with friends locally, but if they fell through, I’d let him know. When I decided to keep my plans, I texted him to let him know. He wasn’t all that concerned considering he had hopped on a flight to Boston to hang out with friends and go to a party. Yup, hopped on a flight that day. He obviously didn’t have a planned flight considering he asked me to go to the movies — Unless he was planning to fly me to Boston to do so…

That night, while out with my friends, I called Boston. He told me some of his new exciting war stories, and I told him of my trepidations about Deep Pockets. He told me I was nuts to write him off based on financial differences, so I decided to see where things went over the next week or so.

We texted a few times more, but interest wasn’t strong on either end as the text messages slowly came to an end. I was on to the next prospect…

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Romantic Evening in the Park

As we left dinner Saturday afternoon following the opera, we began to walk north on Columbus Ave. I had no idea where we were going or what we were about to be doing, but I had a feeling I was going to enjoy the surprise. I was already enjoying the fact that he was being romantic enough to surprise me.

Finally we stopped at the corner of 67th to pop into 67 Wine. Call me stupid, but I was in the store for a solid two minutes before I realized what his plan was. I heard Smiles ask for a cold bottle of white wine, but it wasn’t until he asked for plastic cups that I realized his intentions. Apparently he wasn’t ready for our date to end. We were a few blocks from Central Park. He must have been planning a spontaneous picnic.

It’s been a looonnnggg time since a man put that much thought or care into a date with me. I was swooning from the attention. As we walked to the park, I had a smile from ear to ear.

We passed a family with a child being slightly rambunctious, and he stated, “Yea. The jury’s still out on that one.” I didn’t let that comment fall too far before I scooped it up. On our second date, he pointed out an apartment that would be perfect for two edgy gay men to live in, implying no children. I know children is the last thing one should be thinking about on a second date, but the comment caught me off guard. Children are definitely something I want in my life at some point. Hearing that he’s still entertaining the idea was reassuring. I said to him, “What? Kids?” When he acknowledged, I pointed out how he’d be a great dad.

We entered the park by Tavern on the Green. As we walked out onto Sheep’s Meadow, there was a plethora of people out enjoying a spectacular October Saturday. There were lots of frisbees and couples, much like Smiles and I, enjoying a nice evening in the park just as the sun was setting.

We found a plot of dry grass in the middle of the open field to sit and crack open our wine. He poured each of us a glass. I sprawled out a bit and leaned back onto my elbow to get closer to him to chat. It was really shaping up to be a very special day. A day a few hours earlier I wasn’t sure would come to fruition.

Somehow we got on the subject of high school hookups, which was very interesting to hear him talk about it. When he was in high school, he dated girls exclusively, as did I. I liked that about him for some odd reason. It made him a little “less gay,” if that makes any sense. He talked about his first time. At one point, after one of his stories, we even joked about Saran Wrap being used as a contraceptive. I talked about my upbringing and family. I learned my suspicions of his parents’ divorce were true. The conversation continued though college, finally ending in the real world post college. I found out when and where his love of cars came from (He owns a Mustang from the 60s I’m dying to take a ride in… Among the other things I want to do in it). I learned a great deal about him amongst those blades of grass. I caught a glimpse into how he became the man he is today.

As the sun went down, some cuddling ensued. It wasn’t until we couldn’t see very far in front of us that we decided to leave the park. After a short pit stop at the restrooms to relieve ourselves, we made a detour to investigate where some loud drumming and music was coming from. We discovered it was an impromptu drum session/dance party the broke out in the middle of the park. We stood and observed the celebration for some time, before out of nowhere, Smiles jumped into the mix and started dancing with one of the women. I loved his spontaneous spirit and was VERY impressed with his dancing skills. I was a little taken aback actually. I couldn’t stop smiling. I wasn’t sure if he expected me to join in, but I hadn’t had enough to drink yet to get my ass in that dance circle.

When we had our fill, we walked down a darker pathway. I took the opportunity to pull him aside for a quick kiss. I laid a big one on him. We continued on towards Columbus Circle without further plans. When we neared the subway, he pulled me towards him and said, “So I have a suggestion. Let’s go back to your place, put on gym shorts, and sit on the couch and watch a movie for the rest of the night.” My face lit up with a smile, and I said, “That sounds like a spectacular idea!” With that, we made our way to Port Authority to hop on the bus.

When we arrived at my apartment, I was surprised to find my roommates home with a large group of girls smoking on the balcony after a bar-be-que. I was less than thrilled. Our night of sitting on the couch alone was going to be heavily interrupted by a pack of young girls.

We poked our heads out on the balcony and said hi before heading to my room to put on more comfortable attire. Of course some kissing and heavy petting ensued while in my room, but we made our way back out to the balcony. Smiles planted himself in the middle of the group as if he’d known them forever. He joined their conversation and gave them advice while we all smoked. When Smiles and I had our fill, we went inside to order take-out to satiate our muchies. While waiting for the food, Smiles beckoned me to my bedroom. He was hungry for sex. After the day he showed me, who was I to deny him that pleasure. And, I too was hungry for sex.

However, if you’ve read my blog, you know I prefer to top. There was a polite standoff for a short period as to who was going to hold that position. No words were said, only body positions exchanged. Finally, I found myself in a weaker position and was conquered. If you’re keeping track now, that’s two points for him, none for me. I was okay with letting him top this time, but next time was definitely mine. This wasn’t something we discussed, and I wasn’t sure how to bring it up. I wanted to make sure he wasn’t exclusively a top, but I wasn’t ready to end it even if he was. It was a catch 22.

Warning: The following may be a little graphic for some. After some passionate time, he finished. He was continuing, waiting for me to finish. I explained to him I never finish from bottoming. I was insinuating that I normally top. I wanted to make sure he didn’t think I always liked being on my back. He understood what I was saying, but was a little shocked I never finish from bottoming. He was perplexed. This was twice now we were together where he finished, and I did not. This topic is worth a blog post on its own. Stay tuned…

We cleaned up and went back out to the kitchen just as the delivery man was buzzing. We took our food and plopped down on the couch to eat. As we settled in, the girls finally left the apartment. We decided to watch the second Transformers since Smiles had never seen it. I was happy just spending time cuddled up next to him. Being as it was a long day, I kept falling asleep on him — Literally on him. No matter how hard I struggled to stay awake, I continued to fall asleep. When the movie was ending, I awoke and felt really bad for sleeping on him.

We cleaned up our mess and made our way to the bedroom to settle in for the night. I had one of the best days I’d ever spent with another man. I slept with a smile from ear to ear that night.

When we woke in the morning, I made coffee. We sat on the couch a bit, chatting with my roommate about her night before we finally showered and made our way to brunch at Trinity along the waterfront. We sat outside, yet again enjoying the nice Indian Summer we were having. When we finished eating, I walked him to the PATH to head home. Standing in front of the PATH, I kissed him. I’d never kissed a man in broad daylight in Hoboken before — Especially not in one of the busiest intersections in all of Hoboken in front of everyone watching Sunday football at the bar across the street. I was expanding my comfort zone, and certainly for a worthwhile cause.

As I left him, I had an abundance of energy. The endorphins were flowing! I kicked myself for ever doubting his feelings towards me and put his birthday party out of my mind. With that, I all but floated home. Hopefully, things would only go up from here.

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