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Fillet Mignon and Baked Potatoes

After breakfast at the hotel, we got back on the road to my great-aunt’s house in Mount Vernon to drop off the keys and make our way home. It was surprisingly fast.

I was really disappointed I never got to chat much with the bride. It’d been years since I’d last seen her, and we only speak on the phone about once every four or five months.

During the whole ride, I had a lot of time to think. For me, this is deadly. When I have time to think, I crawl up into my own head and start digging around where I shouldn’t be digging — This is why I lead such an active lifestyle. Thinking depresses me.

A lot of thoughts about Smiles were going through my head. I was a little hurt and upset my advances were rejected in the morning. I also was very disappointed I didn’t get to grab brunch with him. Overall, I guess you could technically deem the weekend with him a success, but I still wasn’t thrilled. I was on unstable ground. I had no idea where I stood with him, and it was getting to me. As usual, I was over-thinking everything.

When we got back to Hoboken, we stopped at the grocery store. I decided to call Smiles to see if he wanted to come over that night. I wanted to make him a nice home-cooked meal since he never cooks for himself. We always go out for dinner or order take-out. He agreed to come by. I also had ulterior motives. I wanted make-up sex for Saturday morning when I was denied.

That evening, when he got off the PATH, I hopped on the motorcycle and rode down to pick him up. I was happy to finally get him out on the bike. He’d been on one before, so it wasn’t as exciting as the first time I’d taken motorcycle virgins on the bike, but it was nice to have him so close to me. We rode back to my apartment with his arms tightly around me. I thoroughly enjoyed it.

I started us off with some artichokes while the fillets finished grilling and the rest of the meal finished cooking. I made more food than the two of us could possibly finish. When we had our fill, I cleaned up, and we made our way to my bedroom for the night. He asked if he’d be spending the night. “Of course you’re spending the night! Did you think I was going to kick you out now?” I responded. “I don’t know. Some people need their rest before Monday morning,” he said. I reminded him the size of the California king bed and assured him he wouldn’t disturb my slumber. If anything, he would enhance it.

Warning: The following may be too graphic for some. I started getting frisky. After not getting any the morning before, I was even more geared up for some great sex. We undressed each other and jockeyed for position once again. I wasn’t making the same mistake again. I made sure I was in position to top this time. When I pulled out my night-stand drawer to get a condom and some lube, he made a comment about the large dinner and not sure it was a good idea. I surrendered, and we decided to use alternate methods. He climbed on top and used his hand behind his back. I was impressed with his ingenuity and his willingness to try alternate methods. However, it wasn’t quite enough for me. It felt great, but I couldn’t quite get over the final hump, as is my issue often.

We stopped and just enjoyed each other’s bodies laying next to each other before we both cleaned up and hopped into bed.

When I woke in the morning, I snuck quietly into my bathroom to shower so he could fall back asleep. If he wanted, I was going to let him sleep as long as he wished and just pull the door shut behind him. However, he had a few things he wanted to get to Monday morning, so he joined me on my morning commute.

We casually walked to the PATH and hopped on. When the time came for him to get off, we exchanged a quick kiss. A lot was going through my mind before that. I was a little afraid to do it because I knew all eyes would be on me as soon as he got off. However, I was the one who initiated it. It was subconscious, but I wasn’t going to let fear of others’ reactions rule my actions anymore. I didn’t care who knew I was gay anymore.

I rode the rest of the way to work not making eye contact with others. I wasn’t 100% comfortable in my own skin, but I was still growing with every day. Things were progressing nicely with Smiles, and they could only get better with added confidence.

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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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Your Cheating Heart

Saturday, I woke up fairly later in the morning. N was still sleeping in my bed, and Boston was still sleeping on the couch when I started to make breakfast. I fried up some frozen homemade sausage patties and eggs. In the meantime, my two favorite men woke up and joined me in the kitchen. I brewed a pot of coffee, and we sat and ate. Boston and I planned to go into the city for the day. He hadn’t been to the city in ten years. He is in music school and asked to check out the original Steinway store to play on some of their finest pianos. We invited N to join, but his plans included shaving his back and getting a haircut.

When breakfast ended, N and I went into my room and fooled around. I was horny since we didn’t do anything the night before and hungry for real sex. But, N wasn’t 100% cooperative. “I feel bad that Boston is out there alone right now. Ya know, we could let him watch,” he said with a wink and a smile. I just laughed it off and continued with my heavy petting. (I did feel bad for Boston because he got out of the shower and all his clean clothes were in my bedroom.) When I finally realized it wasn’t going to happen, we stopped. N went home to get ready for his day of primping, and I showered to get ready for the city. (I would later come to find N accusing me of hooking up with Boston at this point)

When Boston and I arrived in the city, we came upon a street fair. We walked around and got lunch. Following, I showed him some of the major attractions. It was really nice just relaxing with Boston and walking around the city. He started to feel like a little brother. Finally we arrived at the Steinway and Son’s a half hour before they were about to close for a recital. Boston sat at a few of the pianos and blew me away with his talent. I told him if he ever wanted to impress a guy, he should take him to a piano store and it would be in the bag.

We also stopped into to Saks to visit one of Boston’s old friends. We said hi, and he invited us to a house party and a drag show at a bar on the lower east side, Drom.

On the walk back to Port Authority, we passed a few of the pianos sprinkled around the city. I made Boston sit and play after The Naked Cowboy finished tinkering in Times Square. He ended up being filmed by the man in charge of documenting the project. Overall, I’d say it was a good day for Boston.

When we got back to Hoboken, we got dressed to go out and went to my friend K’s for a bbq. We were skipping the house party, but were going to meet them at Drom.

Likewise, N had plans for the night. Originally, he told me he was going out to dinner with friends and they didn’t know if they were staying in the city or coming back to Hoboken. To me, this meant straight friends. I figured i received no details because he wasn’t out to his- fellow diners. I was wrong. As the day went on, I received more details. He was going to dinner with eight gay men, and then it evolved into them going to Industry, a gay bar.

I asked him if it was an issue if we met up at Industry until Boston’s friends went to the lower east side. He told me to come. When Industry had a long line, they decided to go to Ritz, not my favorite bar. Boston and I finished at the bbq and headed to Ritz. On the walk there from Port Authority, I expressed my concerns about N and the night. I told him how shady it felt since he was being somewhat secretive. When we arrived, N’s phone was dying. I tried calling and texting to no avail. We went into the first floor and couldn’t find him anywhere. We tried upstairs to no avail as well. Finally, he texted me back. He was outside to smoking and trying to find us.

When he finally came back in, he was a drunk sweaty mess. I was way too sober to be there. I get very uncomfortable in gay bars for some reason. So, I ordered four straight vodka shots, two of which were for myself. He began to grind his ass in my crotch, and I liked it! This was the first time we could dance together and not create a total scene. A good portion of the night from then on is a blur for me. I got very drunk so I could tolerate the heat and the club and have blacked out a few bits.

When Boston got a text from his friends, we decided to leave. N told me he was coming with us. I was very pleasantly surprised. Boston and I went outside while N said goodbye to his fiends. When ten minutes passed, and he didn’t come out, I went back into the bar. As I was walking up the stairs, I noticed him talking to someone. Men were passing between us going up and down the stairs, but just then I saw him lean in and kiss this man. My heart shattered into a million pieces. In that millisecond, I felt my world crumbling around me. I know it was just one little kiss, but the fact that he was talking to another man, exchanging numbers and kissing broke my heart. I was crushed.

I didn’t know what to do other than run. I turned and sped down the stairs. He must have seen me at that instant because he chased after me. He tried to spin me around by grabbing my shoulder, but I flung my arms into the air and shouted, “Don’t touch me!” All that went through my head at that point was how many other guys were you grinding on and kissing before I arrived at the bar? We never had the exclusive conversation, but at that point, he was sleeping in my bed almost every night. We were in a relationship, even if it wasn’t defined.

He tried to calm me down on the street, but I was making a scene. I didn’t know what to do. When I get heated I get loud. He asked me to have a conversation and stop shouting, but I couldn’t be calm. I couldn’t be rational. I was enraged. Somehow, he managed to calm me down and convince me it was just a peck on the cheek in passing. Out of my inebriation, I let it go, and we went to the next bar. I felt awful. Boston was standing across the street witnessing this whole scene uncomfortably waiting for us to meet up with his friends at Drom.

In the cab ride, I decided I would pretend it didn’t happen for the night. Boston was only in town until the morning. I would deal with the situation later. I needed to entertain my good friend.

Boston lost his ID the night before, so when we attempted to enter the bar, the bouncer was not cooperative. Finally, when I shoved $40 into his hand, he let us in. After we each paid the $12 cover (on to of the $40), we came to realize Boston’s friends already left. The scene was dead. When I realized there was no chance in hell I was going to have fun the rest of the night, we grabbed a few drinks, and I volunteered to go on the hunt to find Boston a man to have fun with. We asked him what his type was. He explained. Then, N asked him if he was a top or a bottom. (This really had no relevance to the situation, and I think N took advantage to satiate his own curiosity.) When Boston was reluctant to elaborate, N said, “I’m a total top, but I love it when he puts his dick in my ass.” This was news to me. Especially since it never really fully made it there. It was just confirmation he was pumping Boston for information because he had a crush on him.

At one point, N and Boston walked to the bar to get drinks while I went to the restroom. Days later, Boston recounted for me the following exchange: N firmly gripped Boston’s ass and said, “How do you get an ass like that? So tight and firm. I’d really like to put my dick in there.” Had I known this happened that night, I would have left the bar with Boston and that would have been the end of it.

When we were all thoroughly exhausted and bored, we hopped in a cab back to Hoboken. No sooner we were in the door, and N was passed out face down on my bed in his underwear. This raised a whole new red flag in my brain. He was donning the sexiest underwear I’d ever seen him wear. His back was freshly shaved, his chest was cleanly shaved and he had a new haircut. All those are fine, but who was he expecting to see his underwear at a gay club. He spent the entire day getting ready for this night out. He never spent that much time primping to see me. Everything was starting to add up. From the business trip I took on, N was quickly distancing himself and seeking relationship freedom.

I went back out to the kitchen to chat with Boston. He immediately said, “OK! What happened!? What did you see!?” I explained to him the kiss, and in typical fashion, he dealt me the truth. He explained how N manipulated me that night as he watched from across the street. He told me to trust what I saw and trust my own instincts. We talked for at least another hour after that.

N’s phone was sitting there the whole time as well. I picked it up and was about to look through his Grindr messages because I wanted to find the closure I needed to tell him it was over. I couldn’t trust him anymore, but if I had proof, I would be able to get over it myself. Boston convinced me how bad that idea was. I put the phone down without pushing a button. To this day, I still regret not looking. It’s completely out of character for me to not trust someone and read their phone, but it would have delivered me the closure I needed.

At that point, I was exhausted. Physically and emotionally. That night I was delivered a heavy blow to the gut and needed to sleep to forget about it even for one instant. Boston went to the couch, and I begrudgingly went to share my bed with the man I had seen kissing another man. I laid down with my back to him and tears streaming down my face. I was crushed by what happened. I had no idea what to do. I still had very strong feelings for him, but couldn’t turn a blind eye. It isn’t who i am. I’m no one’s fallback or second best. However, I did know it was certainly not going to be a fun morning for him either…

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Handing in My Gay V-Card

I struggled with covering this topic so early in my blogging, but it fit in the timeline now. While I never get deep into specifics, if you are uncomfortable with the topic, I suggest you stop reading further through this post…

Something that always scared me was losing my gay virginity!

I mean, I’ve seen penetration in porn more times than I can count. Still doesn’t mean I had any clue what to expect. I was also never one to play around the back door — Never really an area of thrill for me, so it remained neglected. You also hear stories of girls popping their cherries and the pain they felt — I had a feeling that it would be similar for a guy.

I can’t recall how far into the relationship we were when penetration finally occurred. A little over a month maybe.

We decided to spend a night at my place. It wasn’t planned or anything we discussed specifically ahead of time. It just sprung from the passion of the moment. He took charge since this was my first time and obviously not his.

He was a very good candidate to take my V-card. Well hung, but not something that scared the sh*t out of me.

I tried to just relax. I have to say, it went much smoother than I expected. No searing pain. An interesting feeling having your prostate poked for the first time, I must say. This is where the pleasure stemmed — not the actual insertion itself. It certainly wasn’t my favorite part of sex (I love foreplay most) but still enjoyable. I felt closer to him than ever before. The care in his eyes made me feel at ease.

The next morning, we flipped, and he let me have my way with him. Big weekend for me! Two firsts in a matter of hours… I definitely enjoyed this more than receiving. While this became the typical horizontal arrangement, we shared all aspects of sex with each other over time.

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