Posts Tagged bottoming

High Anxiety

After my amazingly awful date with CK, we went home and went to bed. Waking up the next day with him in my bed was my true heaven. Not a day went by I didn’t appreciate waking up next to him, whether in his bed or my own. We were growing inseparable, however, that night we would spend apart.

When we woke, we couldn’t keep our hands off each other. Since we didn’t have sex the night before when we got home, we were both particularly horny. Our sex was becoming so much more than sex. We started making love. We started becoming one. This was something completely new to me. I have had sex with more than a handful of guys, but I never felt the connection CK and I have in the bedroom. We share a strong unbreakable bond as a couple, but when we’re making love, it feels like we could move mountains.

We spent the morning being lazy. That night, I was taking my roommate to J’s wedding. I’d planned to take her before I even met CK. Part of me wanted to pull her aside and ask if she minded if I took CK instead, but another part of me wasn’t sure I was ready for that. I wanted to be ready for that, but it was a big step. Just thinking about it, I could feel the eyes of the people around the room watching us — The two ‘mos dancing up a storm. I know I shouldn’t care about that. I know I need to get used to that, but I wasn’t quite sure I was ready yet.

We watched a few episodes of Game of Thrones while I got ready for the wedding. When the time came for me to head out with my roommate, I had a conversation with CK about his plans for the night. He was planning to hit up a circuit party. I was incredibly uneasy about this. I’d never been, but from the pictures and the stories I’d heard from others, as well as from CK’s own mouth, I was very apprehensive about the whole idea. I trusted CK, but then again, I didn’t. We’d only known each other two short months. Who’s to say he wouldn’t pop X and grind up on some guy all night? Who’s to say he wouldn’t fool around with said guy in the bathroom? Who’s to say he wouldn’t go home with said guy? We were growing very close, but I had no idea how CK would react to the temptations placed in front of him. All these thoughts, and many more, were swarming in my head. But, in spite of all this, I tried to be cool. I had to learn to trust CK. My baggage was not his fault. I would never tell him I didn’t want him to go without me. Hell, I didn’t even want to go myself, even if I was available. It would purely be his decision, however, that doesn’t mean I wouldn’t be a nervous wreck about the whole thing.

When the time came to say goodbye, I simply gave him some parting words gently expressing my concern. “Behave tonight,” I added. “What does that mean?” he asked. I simply just repeated myself. He knew what it meant, but he wanted me to prescribe for him exactly where the line was drawn. The thought of him in another man’s arms made my heart palpitate and beat uncontrollably. It gave me incredible anxiety to picture him sweaty and shirtless with his tongue in another man’s mouth. I wouldn’t be there to hold him back, and my imagination was running wild to fill in the blanks. Because of this, and because I didn’t want to seem psycho to him, he would have to define behaving. It didn’t instill confidence in my mind when he asked me “Well, what exactly is naughty?” If he had to ask, there was a good chance he’d cross the threshold of my comfort zone. I feared for the life of my relationship with CK. I was jealous of faceless men, and he hadn’t even walked in the door.

When I commit to a relationship, I commit fully to it. There are no other guys for me. That doesn’t go to say I don’t notice/admire a hot guy walking by, but I won’t ever act on my admiration. I won’t smile at him or wink. I’ll simply admire him as a gorgeous specimen of a man. I have had my transgressions in the past, but I have learned from these mistakes. I have committed to my man, and he is who I am with. This is incredibly frustrating because I have a very traditional view of a relationship, and the majority of other gay men have quite the opposite. To many of them, boyfriend just means the guy the spend more of their time with than the other guys they see/have sex with. I digress…

Between my regret of not taking him and his going to what I equate to a rave without me, I was an anxious nervous wreck. I kissed him goodbye as we dropped him off at the PATH to head back into the city. My roommate and I sped off to the wedding location and arrived just in time.

It was a gorgeous ceremony and the reception was a blast! I nearly cried watching J tear up as his gorgeous bride walked up the aisle. I pictured myself in his shoes with CK coming to meet my arm and knew I would be a complete mess. I tear up now just writing about it. There were parallels between this wedding and my relationship with CK as well. It was a marriage between a white bread dude and a Puerto Rican fireball (CK is Cuban). For instance, the ceremony was bilingual, as I imagine a ceremony between CK and I would be.

After one of the toasts, I even sent CK a text saying “Te amo con todo mi corazón.” (I love you with all my heart). I was really missing him and wished he was by my side.

When the time came to head home from the wedding, I said my goodbyes and reveled in the love and joy I witnessed between J and his wife. I hoped I would get to the blissful place they were someday. In the car on the way to the hotel, I called CK. I figured he’d already be at the circuit party or wasted or high, but I needed to try. As the phone rang, all my anxiety rose back to the surface. I certainly was not prepared for what was about to happen next…

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One Fine Day

After not sleeping for more than four hours, Friday night, I slept like a log. I was out very quickly and slept straight through to the morning. I was also starving. After not having a full meal the night before, I was feeling ravenous.

I went into the kitchen and began heating our Greek dinners from the night before in the oven. I returned to the bed to fool around with CK while they heated. He was waiting for me with open arms. I dove right into them. I loved waking up with him. It made my day begin so much better.

We continued to fool around and hug and kiss. Rolling around in the sheets with him was a perfect way to begin our day. When the food was heated through, I plated our meals and brought them to bed. We watched TV on his iPad while we ate our brunch. It was very tasty. I loved eating dinner food for breakfast.

Later that morning, I realized I forgot my toothbrush. I needed to go out and purchase one. I got dressed and made my way to a nearby bodega while CK got dressed for the day. I also popped into Starbucks for a Mocha Cookie Crumble Frappuccino. It was a gorgeous day, and I was happy to be outside. With delicious coffee in hand and a new toothbrush in my pocket, I made my way back to CK’s apartment.

I texted CK to get a move-on since it was so nice out. It was already after noon, and I wanted to take advantage of the nice weather. He finally had a weekend he wouldn’t have to stress about finding a new apartment, and I wanted to get some much-needed sun.

We made plans for him to show me his new apartment on the way to Central Park. CK finally got ready, and we decided to walk there. It was so nice out, I wasn’t about to get on the subway, nor did I want to pay for a cab.

We came upon a street festival on Ninth Avenue on the way. It seemed like fun, but it was a little overcrowded. I was anxious to see his new living quarters and hit up Central Park. With blanket in hand, we cut through the crowd to get to his street. Just before we got to his apartment building, we happened upon a cute garden society park. We decided to scope it out along the way. When we finally got to his building, it turns out we weren’t able to see his apartment. His new roommate never left a key with the front desk. The doorman wouldn’t let us up to see the roof-deck either. We didn’t fight it. We left and made our way to the park.

When we got there, Sheep’s Meadow was packed. There was little real estate left for us to put down a blanket. He laid down and took off our shirts so we could get a little color. We talked about a myriad of things while hugging and kissing each other. We made sure not to make a spectacle of ourselves, but we were enjoying each other’s company.

When a little boy walked by us and waved at us, he turned to me and said, “Awwwww. He’s so cute. Let’s get one!” I laughed, but deep inside, I melted a little. I could just picture how awesome a father he’d be. I looked forward to a long future with him, and the thought of us raising a child didn’t scare me in the least. I was excited! I agreed down the road it would be great to raise a kid, but I suggested we get a dog first. At that, he wanted to go shopping for a dog for me. I explained I am not able to take care of a dog. I lead too active a lifestyle, however, if the time came where we’d move in together, I would certainly love to get a dog together.

We spent a good portion of the afternoon lying around chatting. When CK was finally bored with this, he suggested we rent bikes and take a ride around central park. I thought this was a great idea, so we packed up and found some bikes to rent.

This was an incredibly shady transaction. I felt like I was buying drugs. We talked to about five different guys before we were given a bike that may or may not have been stolen. He asked for one of our licenses. Neither of us felt comfortable doing this because we weren’t sure we’d ever see the same guy again, let alone our licenses. He agreed to let us have them without the collateral. A simple fist bump sealed the deal. I guess we look like trustworthy guys.

We took the bikes and sped off on our ride. We did a complete loop of the park. CK broke out his iPhone and started using Video Star again to film us while riding. It was a lot of fun, until he dropped his phone along the way (However, this added greatly to the actual video that resulted from the footage). The phone survived unscathed, and we continued on. We rode around for about an hour before taking the bikes back. Many times we joked about running off with our new bikes, but we didn’t want the bad karma.

I was feeling peckish, so we made our way to Whole Foods to pick up a snack to eat before heading back to Hoboken for dinner. I had another Living Social to use up. We made our way back to his place before heading to the PATH. I left my bag there, and we made our way to 1 Republik. I called P along the way an encouraged her to join us. When we got to the door, we were denied because I was wearing flip-flops and CK and I were both wearing shorts. I’m sure if we stood and argued about going in for dinner, they would have made an exception, but I was in a good mood from an awesome day. I didn’t want to argue.

We decided to hit up Four L’s instead. We grabbed a table, and the three of us had some spectacular drinks and a few plates of food. We had fun people watching and judging the others making scenes in the bar.

When we finished, CK and I were ready to go home. P was disappointed because I think she wanted to hit up the bar, but I wanted to go home and do sex with my boyfriend.

We walked holding hands and having fun the whole way until CK stopped abruptly. He pulled me in and told me he had something to tell me. Just then, I let out the biggest fart I possibly could. My comedic timing was finally on point. We both busted our sides laughing. When I encouraged him to tell me what he wanted, he wouldn’t budge. I regretted the fart slightly, because I think I ruined what I believed was meant to be a beautiful moment. I highly suspected, based on his actions, he was about to tell me he loved me. I ruined it with a fart. I would have to wait until the next time he got the urge to express this. I’d already told him I was close to saying it, but I hadn’t said it yet. I was anxious if to learn if I was right about what he wanted to tell me then.

When we got back to my apartment, CK and I made our way to my bedroom. Warning: The following may be too graphic for some. He wanted to penetrate me, and I obliged. I wasn’t the biggest fan of bottoming on my back, so I turned onto my stomach and raised my hips into the air while he prepped. He was inside me, and it felt great. I loved feeling his body against mine while he kissed the back of my neck. Just before he was about to finish, he pulled out and shot all over my back. He grabbed me a towel, and we laid next to each other enjoying the lasting effects of sex.

When he asked if I wanted to penetrate him, I jumped on the opportunity. I really wanted to fall asleep inside him. He agreed to this, so we got into the spooning position. I lined up and slowly slide inside him while hugging him from behind. This felt great.

Of course, there would be no sleeping. This simply escalated to sex, but it was the best sex we’d had to date. I was penetrating him in the spooning position at first, but before long, I rolled over on my back, and he was on top of me while I was still inside him. It was unbelievably passionate. We changed positions many more times after that, one of which was the reverse cowgirl. I loved every second of it. He was making me feel things I’d yet to feel with him. It was inconceivable!

That wasn’t meant to be what happened, but neither of us complained. We both went to bed that night happy men. Not only did I get great sex, I also suspected my boyfriend truly loved me. I’d have to wait for confirmation on the latter portion, but I was still on a high from great sex regardless. I would sleep rather soundly that night with the most amazing man I’d ever had in my bed.

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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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PR Independence

I had a lot to think about since PR left. Was he really what I was looking for after all? I learned things the hard way over the past few relationships. I’d stayed with too many men for too long after I saw the writing on the wall. I didn’t want to repeat past mistakes.

Was I jumping the gun? Should I give this a shot? There were so many questions and no answers.

I began to build a pros and cons list in my mind.

I didn’t want to lose a great guy, but I was so tired of wasting my time with guys who just weren’t a fit for me.

CONS

He enthusiastically showed me pictures from his ski trip with his buddies in which everyone dressed in drag. They went all out with wigs, heels and bras among other things. I had a strong feeling I was not going to fit in with his friends. He also was a big fan of gay bars. He went on and on about his desire to go to Griffin in NYC on Sunday nights. It is apparently a huge gay party everyone on the scene knows about — News to me. This is not my thing, but I’m not made of stone. I would be willing to be flexible, but if this is the norm for him, we were going to differ greatly. Sadly, he may be “too gay” for me.

We are both tops. I am willing to play ball with a guy I’m in a relationship with, but I get no pleasure from bottoming. That’s not to say he wouldn’t also be willing to trade positions. But, if we both prefer it, it’s probably going to become a problem down the road for us. This was a very frank conversation we needed to have to establish expectations.

I wasn’t thrilled that he didn’t have a full-time job. I wasn’t writing him off because he was unemployed. He was in a long-term relationship with a man, and when that situation changed, he needed to find something. He fully realized what he was facing, but I just don’t know if I’m cut out to date another guy trying to get back on his feet. I put in a lot of work emotionally supporting Smiles until things ended. I really don’t want to come off as elitist at all, but I also wasn’t thrilled with the jobs he was applying for. I never did ask if he went to college, but I got the feeling he didn’t. I wondered the financial stability we would attain if we forged a long-term relationship. He was applying to jobs that I could have done over summer break from college. They had odd hours, and there was a good chance we’d see even less of each other.

PR was a good-looking man, but he wasn’t something you would double-take. I was attracted to him, but some of his physical attributes left something to be desired. I know he was making an effort to get back into the gym, as evidenced when we went together, but was that just because of me or because he really wanted to be in shape. I worried he may be habitually lazy.

Lastly, he was moving back home. Home was at least a half hour drive away, and I don’t have a car. This was going to make seeing each other even harder. I wanted someone who was going to be around when I wanted/needed him.

PROS

PR is only a year older than me. Finally I found someone in my own dating pool. We could share many pop culture references and understand them fully.

He is one of the sweetest guys I’ve ever met. He always had my best interests at heart and took great care of me. He was chivalrous and loyal. He exhibited many of the qualities I really look for in a man. It seemed I’d finally met my match in the dedication department. I knew I could trust him to be faithful and love me for a long time.

He was passionate in the bedroom. Recently I’ve put more emphasis on my needs in the bedroom. I took a major back seat with Smiles in the sack. I needed someone who could truly exhibit the passion I required between the sheets. He certainly fit the bill.

He is easy-going and always up for a good time. I could spring a fun trip on him, even a day-trip, and I know he would be onboard. I lead a very active lifestyle and need someone who can keep up. I had a feeling he could.

Overall, I was leaning towards the cons pile. It seemed to be the stronger argument. They seemed to outweigh the pros this time, and for once I was going to trust my gut.

I had a hard time deciding what to do. I spoke with Boston on the phone, and he told me I would be ill-advised if I went out with him on Valentine’s Day misrepresenting my true feelings. I thought I would have been breaking his heart if I called the night off. I thought it better to go out with him and tell him some other time I didn’t think things were going to work out. He told me I had a tough decision to make, but I needed to deal with it delicately. My friend D told me I shouldn’t cancel on him the day before Valentine’s Day. He suggested going on the date and explaining things later. He was worried PR made plans already, and I would be ruining them completely.

In the end, I finally decide I just don’t want to go. I am so tired of pretending with guys. I need to be more honest. If I feel a date is going south, I need to speak up and stop being so damn polite. I decided to tell him my feelings, but I also did it as a coward. I sent him a text…

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A Perfect Weekend

PR and I had a lovely dinner and topped out night off with a scary movie marathon. When we were sufficiently scared and tired, we went to bed.

I purposely turned off my alarm that night because there was nothing pressing to wake up for in the morning. We could sleep in and enjoy each other’s company in my uber comfortable bed.

I liked sleeping with PR. We snuggled and cuddled before finally dozing off. He didn’t wake me throughout the night with tossing and turning like so many others do. We slept well together. Of course, in the morning, we shared more than just cuddling or spooning.  There was still plenty of snuggling, but things escalated to a new level with the discovery of his matching morning libido. We didn’t have “sex,” as in we didn’t have penetration, but we did just about everything else.

Warning: The following may be too graphic for some. While our mouths went wild exploring every inch of each other’s bodies while our hands enjoyed the touch of skin in symphony. I was constantly lingering at his back door as well. I was testing his limits. I wanted to see how comfortable he was with me back there.

He even mentioned his interest in bottoming for me, but it wasn’t going to happen immediately. He needed to warm up to it first; rightfully so, considering it’d been years since someone penetrated him. I was willing to be patient. I was just concerned that it would happen at all. His willingness to play ball in down the road was reassuring.

It was late when we finally motivated ourselves to get out of bed. I think it was our grumbling stomachs that finally inspired us to make moves. I cooked us another breakfast while he sat on the island chatting with me. I was getting used to having him around, and I liked it. He was a very caring and sweet guy — A hopeless romantic much like myself.

After we ate breakfast, we cuddled a lot on the couch. I was still horny from the morning romp and started to get frisky, pulling down his shorts and exposing his ass. He was getting a little bashful since we were in front of my apartment widows with the street below, but chances are no one was able to see him. At one point, I even completely removed his shorts. It was cute watching his bashful squirm. I was starting to get off on it.

We decided to go to the gym, so we finally picked ourselves up off the couch and went to the bedroom to get ready for the day (now that it was about 3:00). Of course we didn’t simply get changed and head to the gym. We got frisky once again as I pulled him onto the bed. He certainly wasn’t complaining.

My motivation to have bigger biceps finally overtook my sexual desires, and I suggested we finally get ready for the gym.  He went home to change, and I got dressed. He was starting to take a long time, so I told him I’d just see him there — I was on my way.

I nearly finished my workout before he arrived. It was slightly awkward cause I wanted to kiss him when I saw him, but I didn’t want to make a scene. We had plans to go to a Super Bowl party together, so I told him I was going to head home to shower and get ready. I implored him not to doddle since I didn’t want to arrive at the party after the start of the game. He assured me he’d be ready in time.

Once again, he was running behind, but after hopping in a cab, we arrived at the party just in time for kickoff. A lot of my friends were there, so I introduced him to everyone. This was going to be a test. He would he interact with my friends? Would he be outgoing? Would they like him? I care a lot about what my friends think of the guy I’m dating. I was trying out a new strategy this time around. I was introducing him to them much sooner than guys past.

The whole time, I sat next to him on the couch watching the game, I wanted to hold his hand or have him sit in front of me in my arms, but it wasn’t that kind of party. I would keep my hands to myself. I wanted to jump his bones the whole time we were there. I was showing restraint however.

When the game ended, we walked home with D. The majority of the second half, I kept expressing my desire for cake, so we decided to stop at the A&P and grab something. D got some cake as well, and since he lived nearby, we made a pit stop at his place to relieve our bladders and snag a bite of his cake.

PR came back to my apartment to share the carrot cake I bought for us. While we walked, he asked me the most forward question any guy on a date has ever asked me: “Have you ever had any STDs?” I paused for a moment in shock. I indeed did, and it was an embarrassing story. I wanted to know if he equally shared in my shame before I would volunteer that information. He told me he did, so I explained the time I contracted chlamydia. He then recounted the story of the time he got crabs. It was a bizarre but interesting conversation.

While we ate cake, we discussed zodiac signs. We looked up each of ours and checked the compatibility. I don’t believe in that sort of thing, but it was fun and something to pass the time. We moved things to the couch to relax and discussed everything. I told him about all my exs and he told me about all his. We sat there talking until we realized it was 2:00am. I asked him if he was going to stay the night, and he graciously accepted.

Sleeping with him just felt so right. I was happy to have him there. He was a good guy, and I was really enjoying his company. I liked where this was going, but his future was a little uncertain. He was applying for numerous jobs and attempting to figure out a more permanent living solution. For the meantime, we were meshing so well, and I was enjoying every minute of it.

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Juggling Act

Over the course of time, I began talking to a guy who’d been in and out of my life for almost a year. I think I started talking to him on Grindr first. We then found each other on adam4adam.com. Finally, we became Facebook friends.

You would think with all this contact, we’d be best friends or lovers by now, but that wasn’t the case. Whenever I was between guys I was dating, I would once again hit him up. He was very attractive and seemed to have a very level head on his shoulders. I really wanted to get to know him better, but I got the feeling I was going to have to pursue this one. I wasn’t going to win him over overnight.

For some reason, this time around was a little different. He was much more receptive to my advances. When the conversation would die down, I would prod him about losing interest. He would deny it and pay a lot of attention to me. He was constantly asking for me to send him pictures of myself and sending me compliments. It was nice to have a man tell me I was attractive.

We spent many evenings chatting on a4a and Facebook. I got to know a lot about his sexual side through those conversations. They would start innocently enough about our typical lives and somehow they’d always segue into our sex lives/desires. I was okay with this because I wanted a good man with a healthy sexual appetite. This was something I’d come to learn as of late. I needed to stop sacrificing good sex for a decent guy. I needed both.

I was also trying to juggle him in with the other guys on my roster. It is always such a challenge to get gay men to commit to anything. They never seem to want to be locked down to anything. I would schedule a date, and sure enough they’d always cancel or postpone. I was really getting tired of flakes running my social life. When my Friday night date cancelled, I tried to see if he was free for a drink.

I wasn’t able to meet him when he was free. He already had plans to go to Sugarland, a gay club in Brooklyn with a friend. He reported to me about his night with texts and pictures. Apparently he wasn’t having the best time and told me it was “Indian night.” Not his cup of tea. Since we couldn’t meet on Friday, we agreed to try for Saturday night.

It was going to be tough however. I was supposed to be attending my sister’s birthday gathering at a local bar. He had plans to go into the city. We agreed to try to meet up later, but who knew if that would come to fruition. He said, “I may head into the city, but we’ll both probably be out late… Let’s keep in touch and see where we are at later.” Of course, we’d never find each other that night. He still insists he sent me text messages to meet up, but I never received them.

Instead, when I got home, I texted my new “friend with benefits” to come by. I even volunteered to let him spend the night so he wouldn’t have to walk in the cold. He agreed and came by.

We had a great night together. He was really a passionate lover. It’s too bad he was so old. Instead, we’d simply just take care of each other’s physical needs.

At 6am, we woke and fooled around some more. Again, we never had sex because we are both tops, but he did mention the possibly of bottoming for me in the future.

At 8:30, he left to go home to get ready for church. I stayed in my bed and went back to sleep.

When I woke up later, I told him and my new southern friend about my upcoming work trip and how I really wanted to meet them before I went away. The southerner had to pass because he was helping move a good friend into her apartment. We agreed to grab dinner Monday, Martin Luther King Day in the evening. Hopefully this date would finally come to fruition…

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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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Sexy Eyes Pt 2

Things were finally starting to look up for me. I met Sexy Eyes for coffee, and we really hit it off. On top of that, I spent the night in his bed. The compatibility was there on both the emotional and the physical. We both shared active lifestyles and had a lot in common. I was really enjoying the idea of dating him. He seemed like a great guy. Aside from Sexy Eyes, Smiles also showed an interest in continuing to get to know me. We only met for a short period of time over a drink, but he was willing to take more time to learn more about me.

Even though I saw Sexy Eyes twice that Thursday, they were both unplanned dates. We had a planned date that Friday, and I saw no reason to cancel it.

I spoke to him throughout the day to make sure we were still on. He had volleyball again that evening. He invited me to join. In fact, he strongly encouraged me to do it. It was open gym play, and he wanted to play with me. I was very intimidated because he had been playing the better portion of his life. I’m good, but I’m completely amateur. I’ve never had any formal training and have only played recreationally. That doesn’t go to say I wouldn’t play with him in the future, but I wasn’t thrilled with the idea of jumping into that just yet. I’d only just met him (I say that as I am now thinking in my head about how we already had sex).

After work, I went home and relaxed for a bit. He was occupied until about 10:00, so I watched some TV until it was time to shower and get ready. I hopped on a bus into the city to meet him for dinner and was running a little late. I thought since I was late he’d be ready by the time I got into the city. That wasn’t the case. When I texted him to tell him I was at Port Authority, he told me to come up to his apartment until he finished getting ready. I walked up to his apartment and arrived just as he was finishing up.

He answered the door, and we exchanged a kiss. He pulled back quickly and scolded me for not having a close enough shave. I get irritated if I shave every day, and that day was an off day. He complained about his face being sensitive and fear of breaking out. I partially understood, but a larger part of me recognized he was just being a prima donna.

I sat casually on the couch which he finished up. I felt very relaxed and comfortable with him. I was constantly joking with him and making witty comments. It was fun verbally sparring with him. That is alway something I enjoy.

Finally, it was time to go to dinner. We talked about the different options since it was already 11:30. I defaulted to him since it was his neighborhood, and I didn’t even know what would be open at that hour.

We ended up at the Renaissance Diner in Hell’s Kitchen. We sat outside the restaurant and chatted while we waited for our food.

I noticed a trend with him. Every time we had a conversation, it was monopolized by him. He was interesting to listen to, but he was also 75% of the conversation. It wasn’t easy to get a word in edgewise. The conversation was also heavily interrupted by the judgmental comments he made at every passerby. If he wasn’t ripping their outfit to shreds or looking indignant because someone glanced at him, he was ripping apart their walk or the way they looked. He was being entirely over judgmental, and it didn’t look good on him. He even made a comment about how I dress “straight.” He informed me my polo was a bit too loose. “You have a nice body. You should show it off more with a tighter shirt,” he noted. I thought my shirt was actually quite small, and I had no interest in dressing “gayer.”

The meal drug on for some time. It was getting late, and I either needed to go home following dinner, or I needed to get up early the next morning because I was going back to my college for alumni weekend. Finally, after dinner and the endless cup of tea he ordered, we got the check and walked back to his place.

When he told me to get comfortable and ready for bed, I determined I was spending the night. We hopped into bed under the covers, each in our underwear, and turned out the lights. We started kissing and cuddling until he pulled me over and rolled me on top of him.

At that moment, he informed me “tonight it’s your turn,” meaning, I was going to bottom for him since he bottomed for me the previous night. I made a hard stance and informed him that would not be happening. I told him I don’t do that just for anyone, and I have to be dating a guy for some time before I’m going to give that up (since I really get nothing out of it on my end).

He was NOT a happy camper. He even got out his phone to go over the semantics of what I originally said on the subject. Apparently, in a text, I said, “I only bottom for a guy I’m dating.” I guess in his mind, after coffee and two dates, we were dating — Not the case with me.

He started to pout and was getting very combative and confrontational because I wouldn’t bottom for him. “Whatever. It is what it is,” he exclaimed. I laid there for a minute, and finally said, “Do you want me to go?” He replied, “Where are you going to go? It’s 2:00 in the morning.” I told him I would go wait in Port Authority for the next bus back to Hoboken. He said, “If you want to go, go, but I’m not asking you to leave.” That was a clear indicator I should have gotten dressed and left, but selfishly I needed sleep. I had alumni events the next day, and spending the night standing in Port Authority was not something I was interested in. Instead, I curled into a ball and laid as far to the edge of the bed as possible with my back facing him.

When I woke in the morning, it was a half hour before my alarm was set to go off. I quietly got dressed and was ready to walk out the door. I wasn’t sure if he was awake, and I didn’t know how to address our current situation. I was willing to give him a second chance if he was willing to be understanding on the topic. I stood over him to see if he was awake until finally I reached out and touched his leg. He jumped up and I said goodbye. He picked his head up to give me a kiss and said, “I’ll talk to you later.”

With that, I left. There was no way in hell I was going to be the one to make first contact. He treated me like a common hookup and demanded I give it up to him when he knew I wasn’t comfortable with that. Granted he was willing to do it for me the night before, but that was a choice he made. I did not force anything upon him.

On my walk to the bus, I played around on Grindr, answering my messages and seeing who was awake to pass the time. Ironically, this is the last time I would be on Grindr for some time, but I needed something to distract myself from the sh*t-show I was living.

Of course he never called or texted after that morning. It just proved to me it wouldn’t have been a good relationship, and I was happy to get out when I did. I didn’t need that kind of drama in my life, and I certainly wouldn’t miss it. Over the course of twenty-four hours, the relationship between us completely soured, and I would have to go back to the roster to find a more suitable candidate…

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