Posts Tagged masculine

Working It Out Around Work

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…

After a special night in with CK, we woke in the morning to the sound of his alarm at 8:00am. It took him a long time to shut the alarm off, but I was too out of it to rouse him or reach over him to turn it off myself.

When we finally woke, we spent a good portion of the morning snuggling and kissing. He told me how happy he was and smiled. We tickled each other until the other protested enough to warrant stopping. We were constantly expressing our utter joy to each other. Everything he said felt extremely genuine. He always used the term “baby” to refer to me, and it made me melt every time. Either he heard me and was acting on it, or he was an extremely talented actor.

I finally managed to sneak away to hop in the shower. He was in the middle of doing laundry, so he had no clean towels, so he told me to use his on the door. I went into the bathroom. I was not feeling well the entire previous day. I was back to feeling uneasy, and I knew I needed to relieve myself. I did, and I immediately noticed how bad a smell I created. I quickly flushed and did my best to dissipate it. I turned the shower on before sitting down to mask any sounds I would create. Just as I hopped in the shower, CK came into the bathroom to offer me a fresh towel. I was mortified. I was sure he smelled the odor in the air. When he left the bathroom, he left the door open — I’m sure to vent the bathroom. There was nothing I could do about it, so I tried to forget it.

It was humorous because the night before, I was commenting on him burping and how I thought it was sexy. He was certainly masculine. I was tired of all these gay men acting like women. We’d also talked about farting in front of each other when he was at my place and how we were not at that comfort level yet. It came up again in jest while we were wrestling on the bed before my shower. He also playfully joked about picking my nose, but assure me he’d never do that, as well as going to the bathroom with the door opened — Another topic we covered when he was last at my place. It was fun that we could chat about such casual things. It showed me how real he was.

I finished my shower and came back to find him still in bed. I scooped him up and carried him to the shower. I didn’t want to be the reason he would be late. While he showered, he offered me a yogurt for breakfast. I made a few phone calls to shift a doctor’s appointment and ate while he got fresh. He returned to the bedroom and coaxed me to the bed to cuddle more before heading out to work.  “Just two more minutes,” he pleaded. I was fine on time for work. It was him I was worried about. But, if he wasn’t worried, neither was I.

The subway he took was right outside my office, so we walked together. Half way there, we held hands and joked about a few things. “One thing I must say about you. You certainly make me laugh. That you certainly do,” he joked. I was smiling from ear-to-ear. I told him I would try to swing by to see him after I went out to dinner with my team to say goodbye to a coworker. Ironically enough, she was headed to his agency. He would be inheriting one of my favorite coworkers. With that, we kissed each other goodbye. “It’s all downhill from here,” he added.

During the day, I texted him to tell him a funny story about my coworker. I also added, “I had such a good morning. I’m in such a good mood! This morning was perfect.” He responded, “I walked into the office on an invisible carpet of sunshine and rainbows :). ‘You fit me better than my favorite sweater.’ ” I can only assume that was a song lyric.

Later in the day, I had a brilliant idea. “After my dinner tonight, I was planning to swing by and see you and then take a car service home. Do you have any interest in coming home with me tonight to watch Revenge instead? I don’t want you to get tired of me yet, but I thought it would be fun for us.” After a few minutes, my phone lit up with: “Best. Idea. Ever… You. Revenge. Car service. Falling asleep in your arms. And your bed. Waking up with you. And your shower. #heavenly… Enchanted carriage? Check. Castle? Check. Gorgeous, charming and no doubt horny prince? Check.” Once again, he had me smiling from ear-to-ear.

After my work dinner, I made my way to his apartment. I called him to let him know I was on my way. The dinner had lasted longer than expected. It was now close to 11:00. When I got close, he texted me to meet him on the roof. I went up there, but he was nowhere to be seen. As usual, he was running behind.

Finally he joined me on the roof. I gave him a BIG kiss. I told him a little about dinner. He had the idea, since it was supposed to be a full moon (even though we couldn’t see it through the clouds) we could meditate. He was very cute about it. He told me about it in a very roundabout way, almost as if he was embarrassed by it. I told him I would love to do that with him but some other time. I’d already called the car, and I was sure it was already waiting at my office. He was disappointed, but I assured him we would do it another time.

We walked to my office, and I took him up to show him around. I needed to grab my bag. He asked if we could get frisky, but I pointed out the cameras around the office. We made our way back downstairs and headed to Hoboken.

When we got back to my place, we immediately went into my room. We snuggled in bed for quite some time. We were also both quite excited to watch Revenge. We’d planned to watch it together, and I was quite excited.

It was really nice sharing the show with him. I knew how much he liked it, and I enjoyed it as well. I finally had someone to chat with about the show while watching. When it ended, we brushed our teeth, pulled up the covers and dozed off in each other’s arms. I was really starting to get quite used to this!

When we woke in the morning, there were copious amounts of fooling around, but no sex. It was incredible waking up next to him. From what he told me, he felt the same way waking up next to me. We enjoyed spooning and cuddling for a long time before we finally motivated ourselves to get out of bed. This was the first time CK spent the night on a work night. I made us breakfast while he showered.

He joined me in the kitchen to eat, and when I was finished, I hopped in the shower. We both got ready and walked out the door. As we descended the stairs, he pulled me aside to plant a big kiss on me. He commented on this being the first time we spent time together where sex wasn’t involved. “I actually enjoyed that it doesn’t have to always be a requirement. It’s a nice to have. Let’s just not make it a habit,” he said with a laugh.

With that comment, I started to really fall for him. We were on the same page completely. I loved sex with him, but I was actually reassured by the fact we spent the night together and didn’t have sex. It proved to me he wasn’t just into me for sex. Maybe there was something more…

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The One I’ve Been Waiting For

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!

Never before have I prefaced an entry by giving away some of the details of what’s to follow, however, I’ve received numerous comments from readers tired of reading my “sex journal.”

“Your blog used to be interesting when it was about your relationship with your ex bfs, but it turned me off when it became a sex journal,” wrote one reader.

We’re both on the same page here. I dislike writing about these trysts as much as you dislike reading about them. It’s bad enough I’ve lived them once, let alone having to live them all over again when I write them.

So, without further ado, I am pleased to present you a love story…

On a Wednesday morning in April, while on my way to work, I happened to poke around on Grindr a bit. There was a message from an interesting guy on there. We began to chat a bit while I walked. He seemed pretty cool. I was about to head underground, so I quickly asked him for his phone number so we could continue the conversation on the other side.

We chatted a bit over text, and I came to learn a few things about him. I explained to him I wasn’t looking for sex, so if this was his motive, he should move on now. I was there purely for dates and friends. He seemed okay with that sentiment, and the conversation continued for a bit. I tried to check his spontaneity and asked if he would be interested in drinks that evening. He couldn’t because he had to work late. That’s when I learned he worked in advertising. I explained to him, if anyone understood working late for a pitch, it was I. I explained I too worked in advertising. When he told me he worked downtown, I started guessing what agency. Ironically enough, he worked for my previous agency. He worked closely with one of my favorite ex-coworkers. We were really hitting it off and I was excited to meet him. We agreed to make plans in the near future.

Wednesday evening, I was on my way home from a mediocre date. I fired up Grindr on the bus ride home and noticed he was on. I messaged him to say hi. He and asked what I was up to. When I told him I was on my way home from work, he responded, “You’re kidding me! Let’s f*ck.” My heart sank immediately. I had such high hopes for him. I was crushed. “You don’t know who you’re talking to do you? This is [O.G.A.A.T.],” I shot back. He admitted to confusing me with someone else and began damage control. I think he immediately realized he lost any shot of anything with me, however, he still took the time to apologize profusely.

If you know me at all, you know I give second chances out fairly often. I decided to lay on the guilt a little bit, but also give him the opportunity to redeem himself. As I got off the bus, I picked up the phone and called him. His timing caught me at a vulnerable moment. I was turning my dating life around. I told him what he did wasn’t cool. Again he apologized. I told him I would turn a blind eye this once for one reason; a few days prior, I probably would have said the same thing on Grindr. I couldn’t hold it against him when I too had treated Grindr in this way. He fully comprehended what I was saying and promised not to let me down.

The following day, I asked him if he would be interested in drinks Friday for happy hour. He immediately agreed that would be a great idea. When Friday arrived, we made more definitive plans. Since I was done work before he was, I offered to come down to his neighborhood. I just told him to text me when I should start walking down there, and he did. I texted him when I got the bar, but he was still working. I told him I’d hang out by the bar for a bit. I walked a block to Starbucks, got a coffee and wrote a blog post. I needed a kick in the a$$, considering it was a Friday night after a long week. When nearly an hour passed, my patience was at its end. This guy was not winning me over by any means. I was a block away from the PATH and very tempted to just leave. Just as I was closing my laptop, I got a text from him. He was on his way.

We met on the street in front of Employees Only. He’d never been before, so I led us inside to order a round of drinks and find a wall to lean against. He apologized for taking so long and explained what was going through his head. He was working on something late and told the editor they’d need to pick it up again on Monday. He’d already used up one of his chances with me. If he messed this one up, there’d be no redemption. I thought it was cute, and I loved his honesty. We talked about our jobs and our shared favorite coworker. I told him about my coworkers and how we’d be excellent fodder for a reality show. (I really work with a circus of a crew, but I love them!)

We were really hitting it off. Everything just felt so easy. He was also incredibly easy on the eyes. I felt I was a bit out of my league here. He was five years my senior, gorgeous, smart, witty, well spoken, had a solid job, etc. Basically, he was the full package. I already knew he had a healthy libido as well, so we’d probably be fine there.

After two rounds of drinks, he took the opportunity to kiss me. I can’t tell you how much I loved that kiss. He was a real man, and he kissed me. I was crazy swooning. We decided to make moves. In our conversation, I was talking about what I do in my free time and mentioned the pier I lounge on directly across from the Christopher Street pier. He suggested we take a walk out there before grabbing a bite to eat somewhere.

We walked holding hands to the end of the pier. He took my bag, set it on the ground with his own, and we walked to the railing. He stood facing the water and pulled me in, wrapping my arms around him. It was incredibly romantic. While we talked, I nuzzled his neck. Things were so easy with him. There was no drama. There were no games. There was just us. I couldn’t believe an hour earlier I was ready to abandon our date and go home.

He turned around and hiked himself up so he was sitting on the railing dangling over the river. I was between his legs with my arms wrapped around him while we chatted. I decided to tell him how new to the game I was and tell him my coming out story. I figured I might as well get that out of the way, because if it was going to scare him off, I figured it was better sooner rather than later since I’d already grown so attached to him. He was totally cool about it. This is also when I learned our age difference of five years. Obviously I was fine with that considering Smiles was nine years my senior. He was cool with that as well.

As we walked to find dinner, he told me about his coming out story. It was interesting and not all that different from mine. I learned he was bisexual through college, which actually was reassuring to me. I liked men that had experience with women as well. It wasn’t a necessary skill I needed to see them utilize. I just liked knowing they’d experienced women as well and realized they were more attracted to men. It also generally proved to produce more masculine men, which I’m far more attracted to. I also learned in that conversation he was a cancer survivor. I didn’t know how this guy could get any better. He was like Superman.

The date was off to an amazing start. We were walking hand-in-hand to find dinner somewhere, and I didn’t want the date to end. I was on cloud nine. I think I floated the whole way. We finally arrived at a spot I was quite familiar with, Frankies 570. So familiar, in fact, I’d been there a few days prior. The date was just beginning. I couldn’t wait for the next course…

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On A Sexual Roll

I have a generous amount of vacation days, as I did a very good job negotiating when I was hired at my job. I don’t, however, have friends who share the same luck. They can either take the time off and have no money to travel, or they have money, but can’t get away from work. On top of this, being single leaves me only with the option to travel – Alone. I don’t enjoy this. As a result, I build up all these vacation days and never use them.

When the new year arrives, I have until the end of March to use up all the days I carried over. As a result, I start giving myself four day work-weeks and have staycations. I decided to take Monday off after the local holiday in Hoboken. As per my usual, I woke up horny and turned to Grindr. I tried to get one guy I’d been flirting with to come to my place. He lived in the city in Harlem, so no matter how hard I tried, he was not going to come to Hoboken.

After him, I went through a ton of Grindr guys trying to find someone to come over for some morning fun. None were biting. I turned Grindr off after what I’m sure was over an hour of surfing, and hopped on the computer. I thought I would give adam4adam a shot. I had messaged a few guys, but I wasn’t getting a response. That was until I found one guy who is 26 and worked in the area.

He was a good-looking guy, as per his profile pictures. We began exchanging messages. He unlocked his pictures, and I got a glimpse of his face finally. He was a very sexy, light-skinned black man. He had this college jock look about him, and I was very turned on. His body was fit, he was clean-cut, and his smile was utterly adorable.

I asked him if he’d be free later to swing by. He had a light day at work since his boss was out of the office. We discussed logistics since he worked in neighboring Jersey City. He could either take a cab or the light rail to my place. I gave him all his options, and we made a plan for him to come by around 4:00. I learned he was usually a top, but he was willing to bottom for me. This was extra exciting to me, because I had greater hope he’d be a more masculine man than most typical bottoms.

When he arrived, I was immediately taken back by how sexy he was in his work clothes. Then I noticed his incredible blue eyes. He looked just like Michael Ealy. He was very masculine and had on slacks, a dress shirt, a tie and an incredible smile. He wasn’t nervous about this at all, which I found to be very sexy. I led him into my room, and he immediately began undressing himself. I liked his matter-of-factness — His “I know the drill” style. I sat on the bed talking to him as he undid his tie, stripped off his shirt, removed his shoes and took off his pants.

Warning: The following may be too graphic for some. The man had an amazing body. I was very pleased. I could tell he takes good care of his body, and I was ready to ravage it. I wanted to touch every inch of his milk chocolate colored skin. I was still sitting on the bed in my gym shorts and tank top when he unexpectedly took off his boxer briefs as well. If I wasn’t already excited before, now I was rock hard. He walked toward me as I stood and removed my clothes as well.

He was a well gifted man, and once we were both fully undressed, we laid on the bed with him on top of me making out for a bit. He had amazing lips and knew how to use them. He had a strong body, and I enjoyed wrapping my arms around him. It was hot! We began to fool around and explore each other’s bodies.

Ater some making out and mutual oral pleasure, he got into position for me to use some of the techniques I’d read in Tickle My Tush. I knew he was normally a top, so I took the time to make sure he was fully ready and not rush things. I was enjoying myself as well. He seemed to be really enjoying himself as well from the sound of things.

That’s when I reached over the edge of the bed to my nightstand and grabbed a condom and some lube. He was face down on the bed in front of me, and the real fun was about to begin. I really enjoyed being up against his body and feeling him. He may not have been a bottom, but he sure was passionate in the bedroom and knew how to use his body. The sex was great, and eventually he finished. Seconds after that I too pulled back and finished. It was very hot! I grabbed a towel to clean up his back and the sheets below while we exchanged a few more kisses and expressed our enjoyment with each other.

Just as he undressed like he knew the drill, he began to get dressed. I learned he was heading back to work. I was surprised because he lived in the city. I assumed I was a pit stop on the way home. I felt bad for him he had to return to the office, but I didn’t regret inviting him over. I had a great time with him and would certainly be willing to have him swing by again sometime.

I walked him to the door and gave him another kiss goodbye. He was such a polite gentleman. I could tell him momma did a good job raising him. He thanked me, to which I replied, “Thank me!? Thank you! That was great! Anytime you want to do this again, you know how to reach me.” And with that, he was gone.

In the coming weeks, we’d try to do it again, but he was having a busy week. I could tell he was more than just a hot body, so after that, I asked him if he’d ever be interested in grabbing a drink sometime, but I got no response. Perhaps he will just remain a fond memory of a day off…

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No Day at the Beach

For one, I was really enjoying the company of my new friend, The Navigator. Secondly, the weather was amazing. I couldn’t have been happier to be away from the cold weather on the East Coast.

Contrary to my plan, the weather wasn’t fully cooperative. The closer we got to the coast, the cloudier and colder it got. I didn’t care how cold it was, I was not putting the top on the convertible back up. I did, however, turn the heat up. That kept us cozy while we acclimated to the new weather pattern.

We drove around for a little before finally finding a parking spot. We walked to the beach, and we spread out the blanket I asked him to bring. He sat down, and he started pulling out the other provisions he brought — A bottle of Sprite, a bottle of Absolut, and some snacks and granola bars. I think I was falling in love. He was spontaneous and courteous. I added the provisions I grabbed at the gas station to the pool.

We sat next to each other commenting on how much the weather deteriorated and chatting about some of the surfers. We were among sparse company. The only other people brave enough to hit the sand that day were the surfers we both scoped out.

We relaxed and the conversation from the car continued. He talked about his family and his background. I learned he was a Jehovah’s Witness. He wasn’t very passive in his faith either. He had the prestigious honor to attend a bible college in Brooklyn. While there, through a slip up, it was discovered he is gay. He was excommunicated from the religion and has very limited contact with his family.

My heart was breaking to hear this sad story. He was an incredible man for surviving all that, and even more impressive for his comfort telling this to virtually a complete stranger. I told him about my religion, and my new outlook on it. I told him about my conversation with my mother on Christmas Eve, even though it was nothing compared to what he went through.

As if his story couldn’t be more complicated, I learned his brother is also gay and struggling with his religion. He was actually finding men online and hooking up with them at rest stops until he was nearly caught by police. His brother chose to take a different route in dealing with this. The Navigator tried to suppress his homosexuality with the aid of his religious elders, but came to accept who he is. His brother was not as fortunate to have the mental confidence to know himself. He was going through conversion classes to help him become heterosexual. They were trying to brainwash him. My skin was crawling at the sound of this.

After leaving his religion, he moved around a lot. One move was for a man, but obviously that didn’t work out. He’d been in LA for roughly a year and was still settling in.

I was really enjoying his company. We took turns making trips to the restroom, and when he stood to walk away, I took the opportunity to check him out. In the back of my head, a voice was screaming, “Be careful! You’re on vacation. You can’t fall for another West Coaster!” My heart was not going to be so easily convinced. I was cautiously proceeding. I really liked this guy. If he lived in New York, we’d definitely be dating. He was just what I was looking for. A masculine man who had his life together and knew what he wanted in life.

When we sufficiently froze our a$ses off, we hopped back in the car and made our way back inland. While we drove back to Glendale, I realized I’d already used up all my condoms and almost all the lube. I would need to stop for provisions along the way, but it wasn’t going to be easy with The Navigator with me. I decided to stop at a CVS. While he looked for the bathroom, I looked for the condoms and lube. I told him I needed to buy sunscreen, which I did, but that was very low on the priority list.

When I finally found what I needed, I realized they were under lock and key. I had to push a button that made the announcement, “Assistance needed in the family planning department.” Family planning couldn’t be further from what I was looking for. The irony was killing me. As Broadway always joked, “Butt babies don’t live.” I wondered what I’d done recently to deserve this karma. It was going to be nearly impossible to pull this off without him seeing what I was purchasing.

Someone came to unlock the case, and he turned his head in an attempt to give me my privacy. That was long gone. I grabbed what I needed and quickly walked to the checkout counter. Of course, when I arrived, there was a long line. I took my place in line behind an old man and hoped The Navigator was still looking for the restrooms.

I was next in line. Maybe I was going to get away with this after all. It wasn’t in the cards for me. The old man in front of me was taking FOREVER! Every second that passed was nerve-wracking. I didn’t want him to see what I was purchasing because it may have been perceived presumptuous.

Just then, he walked up behind me. My cover was blown. I tried to hide the products in the crooks of my crossed arms, but there’s a really good chance he saw what I had. Of course, this was also the moment the next register opened up. I walked up and purchased my items. I paid, and we walked back to the car without mentioning what I bought at all.

We talked the whole ride back to his apartment. When I turned onto his street, he turned to me and said, “Sooo, do you want to hang out some more?” Without hesitation, I shouted, “Yes!” He asked if I want to go back to my hotel room and hang out, and I agreed that was a great idea!

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The Navigator

In my Grindr surfing, I’d hit up more than a handful of guys. I struck up a few conversations and blocked a few I wasn’t interested in, but since I don’t pay for Grindr Xtra (I refuse to pay for the service on principle), there were a lot of guys floating around my screen in no man’s land. I casually kept a conversation going with a handful since I’d be there a few days and wanted to keep my options open.

On in particular didn’t really stand out from the crowd. We had weak conversation going — Just the pleasantries. “Hey. What’s up? What brings you to Grindr?” etc.

When I woke, I called Hertz and confirmed they would be picking me up that morning to take me to the lot. A woman drove me while I chatted some more on Grindr. Of course, when I got there they upsold me: “My only compact is at the car wash. You can wait, or for $10 more a day, you can take the convertible.” “Sold!” I exclaimed. I was like a kid in a candy store. I immediately put the top down and sped off back to my hotel. I couldn’t wait to hit the beach!

While I ate my breakfast in the hotel restaurant, I continued to poke around Grindr. I had plans to go to the beach that day, but I would be returning in the evening. Maybe I could find someone to hang out or hit up the bars.

The guy I’d briefly chatted with the previous evening messaged me once again and said, “Good morning.” We talked about what we had planned for the day. I mentioned my plans to hit up the beach when he replied, “What time should I be ready.”

A huge smile lit up my face. “How bout now?” I quickly shot back. Much to my surprise, he was just as serious as I was. “I have a few errands to run, but I can be ready at 11:00,” he added. That was in a half hour. “Perfect. I just got back from picking up my rental, and I’m eating breakfast now. Shoot me your address, and I’ll swing by around 11:00 to get you,” I said.

I gathered my beach things, hopped in the car and sped off to pick up my beach buddy. When I arrived in front, I called him, and he came out. I had only seen a few pictures, but was pleasantly surprised that he was a masculine good-looking man. This was going to be a good day!

We introduced ourselves, and I thanked him for joining me. I immediately asked him if he knew the area and told him my plans to go to Manhattan Beach. He agreed that was the best idea, but told me he had no idea how to get there. I told him he’d be playing navigator while I drove.

We talked casually about our different and similar Grindr experiences. This guy was real. He was very open about things and seemed very smart and very savvy. The longer the conversation drew on, the more I liked this guy. It was an extremely risky move to pick a stranger up in a car and spend the day with him, but it was really paying off. For once, luck was in my favor.

I learned a lot as we drove to the coast. He told me all about his job and what he wants to be doing in the future. I told him about my job, and he asked a lot of questions. He really wanted to know the intricacies of my day-to-day. It was quite apparent we were both really digging each other, and the conversation was so casual like we were friends for years.

On top of it all, he was chivalrous and super sweet. Everything he said came with a gentleman’s tone. He wasn’t self-centered, and from the stories he told, I could tell he was a popular, well-liked guy.

This was turning out to be a pretty great trip, and I was just getting started…

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Highs and Lows

I had been on OKCupid only a short while before I met Smiles. I met only one person from the site, LES, and that was already after I met Smiles. I have to say, I’m not that big a fan. Every search I did produced few candidates I was willing to entertain. No one was good-looking, and no one had exciting profiles. It reaffirmed for me why I originally was so against dating sites. I felt like it was full of desperate men.

Rarely would I receive a message for a worthy candidate, but when I did, I would quickly respond and dry to stir up some dialogue.

I started chatting with a nice southern boy from North Carolina who moved to the city in the previous few months. He seemed like a really genuine guy who wasn’t into the scene or fully out. I was very attracted to that. The southern boys always brought a little extra something I always liked. They were mannered and real men.

We messaged back and forth on OKCupid for some time before we exchanged phone numbers. One night, he asked if I could chat. I asked him for his gchat or AIM name. He responded, “No. I meant on the phone.” To which I responded, “Sure.” We spoke on the phone for an hour that night. I really got to learn a lot about him. He was volunteering a lot of information about his upbringing and his company and where he is today. He told me how he hates gay bars. He even took the time to tell me about his “hetero life partner.” That’s what he calls his best friend and roommate he left behind in North Carolina when he moved up here. Apparently they were completely best buds, however, nothing sexual ever transpired between the two of them. It was sexy to hear him speak about such a masculine love with his friend. I was really liking what I was hearing, and the fact that he wanted to call gave him so many bonus points in my book. I even told him that last bit of information, which I think he really appreciated.

In the morning, things switched to texting. He was horny and asked me to send him some more risqué pictures. I was onboard. I was all the more happy he asked actually. It proved to me he had a healthy libido, especially in the morning, which is when I’m at my horniest. We exchanged a few racier pictures and went to work. We made a commitment to each other to try to find some time to go out on a date in the near future. I couldn’t wait. He was not only sexy to look at and hopefully to touch, but he was also sexy and masculine in his personality.

In the meantime, I was also talking to a guy I met on who I’d been messaging on and off for over a year. Between every relationship, this guy and I would exchanges flirty messages and pictures, but nothing would ever transpire. It was so frustrating because I found him to be very hot. He’d get very flirtatious, but never follow through or agree to meet me. Now I was making some ground. This time around, he seemed genuinely interested. I’m not sure what changed, but I was going with it. He was coming back home after a weekend away, and we were texting the entire ride back. When he got home, we continued the conversation on Facebook with a lot of banter and playfulness. He was really coming around on me. I continued to propose a date, but it wasn’t the easiest. He was open to the idea, but I couldn’t get him to lock down on a specific time and location.

A lot of our conversations revolved around sex. Again, after the dry spell I went through with Smiles, I was happy to hear it. I also knew he had a great job, as he had his doctorate and was using to teach at a college and work at a clinic. He really seemed like the full package. From looking at his Facebook pictures, I could tell he loved to travel and he loved to have a good time. He also lived close to me. I felt like this time, I had it in the bag.

That night, I found a guy on Grindr. He was visiting, and the host he was staying with was away. He knew no one and wanted to go out. I was already contemplating going out, so I convinced my roommate to join us at the bar for casual drinks. We met him on the walk to the bar, and when we did, I was shocked. He was tiny. I’m 6’2″, and he was easily 5’2″. My roommate immediately whispered a comment to me. Then he opened his mouth and the queeniest voice came out. I was so turned off, but I couldn’t be rude.

We awkwardly sat and chatted at my favorite bar that night. It was dead, so there wasn’t even anything to distract from the incompatibility. When my roommate and I had our fill, we decided to head home. The little munchkin followed us home. He asked if he could come over, and I agreed. It was a moment of weakness. I was horny, and I thought he could be fun.

BOY WAS I WRONG. He was beyond a stage five clinger. After some making out and heavy petting, he spent the night. The next morning, he told me the only way we could have sex is if I could see him the next night. Foolishly, I agreed. It was bad. No. Let me rephrase. It was awful! I couldn’t get rid of him fast enough. I kept laying it on thick how much I needed to get to work, and finally I scooted him out the door.

This was just gay karma coming back to bite me in the ass. I never should have led him on. From the bar, I should have had the balls to just send him home and take care of myself. This is where my penis gets me into trouble. Soon enough, he’ll learn his lesson…

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Unexpected Lovin’

All week long, I was still reeling from my date with Prince Charming. He was really everything I was looking for in a man. Mature, driven, sexy, interesting, masculine… the list goes on. However, I couldn’t limit myself to just him. I needed a distraction or I would end up driving him away. Pillow seemed to have fallen by the wayside. Not sure what went wrong there, but I wasn’t going to put any more effort into chasing him down. After coffee with the midtown trainer, I realized the potential we had for compatibility. He seemed like a really great guy. On top of that, he was texting me asking when we were going to finally go out again, which is always a good sign. Apparently I made a good first impression.

We agreed to go out for dinner that Wednesday. He chose an Italian restaurant, Il Melagrano in the neighborhood between his gym and apartment. When I arrived, he was already sitting at a cozy table at the back of the establishment. I apologized for being slightly tardy, and we got to it.

We chatted a bit about what we were going to order, and then turned the conversation to our days so far. He had a very busy morning, while I had a day mainly filled with surfing the internet. When that conversation got stale, I brought the conversation back to something we spoke about on our first “date” — His skydiving trip. He was very excited, and we joked about all the possibilities of things going wrong and what he could do about it. When age came up, I could see he was uncomfortable with how much younger I was — Seven years. I told him not to think about it and to judge me on my actions and words and not my years on the planet. We changed topics of conversation periodically from working out, to work attire, to the Tough Mudder, to Fire Island, his dog and so on…

When our meal arrived, we continued the conversation. I feel as if I was doing a lot of the talking because he finished his food much sooner than I. When I realized this, I started asking more questions and did less of the talking myself. The conversation flowed well over our single glasses of wine, but it wasn’t 100% fluid. At one point during the conversation he mentioned his studio apartment: “Well, you’ll see it some day when it’s not a complete mess.” It was nice to hear, because it showed promise of another date and signaled to me he was a gentleman.

After coffee and desert, I walked him home. The conversation on the walk was much more jovial and relaxed. I felt very at ease with him. When we got to his apartment, I was ready to say goodbye on the street, but he invited me in to his lobby. We started making out and things began to get heavy. He backed himself up against the wall and pulled me in closer. His hands were all over my body, including down my pants, and I was seconds away from him having my shirt completely off. At that point, he paused long enough to hit the elevator button, signaling an invitation upstairs.

From the look of him, he was tipsy off the one drink we had at dinner. I wasn’t expecting to move this fast, so I was a little caught off-guard. I liked this guy and debated if I should be doing this with him already, but I just went with the flow like I usually do. When we entered the apartment, I got to meet his dog. She was very cute and friendly. He put her in the bathroom so she wouldn’t bother us while we got busy.

Seconds after I sat on the couch, he ripped my shirt off. At least I knew he was attracted to my body. Him being a personal trainer, I was self-conscious about my body. His was nothing short of spectacular, so I was hoping I’d live up to his standards.

We moved things to the bed, and both of us had our pants around our ankles. We were doing some heavy petting and grinding. It was a good time, but once again, I was having second thoughts about this. After some more fooling around, he finished. I wasn’t able to join in the fun as my head was a bit distracted. And then, on top of that, I was worried he’d wonder if there was something wrong with me or if I wasn’t attracted to him. Neither was the case. It’s just something that has always been adversely affected by mental distraction.

While he went to clean up, I began to put my pants back on. He already established he was getting up around 5:00am to go for a run and had a 6:00am client. I knew he wouldn’t want me to linger for small-talk. He came back and sat next to me with the dog at our feet. She already took a shining to me after I gave her an extensive belly rub, but when he went to give me a kiss, she started making noise. At this point, he made a game of it and started testing her, scolding her between every kiss until she didn’t make a sound.

At that, I gathered my things and said goodbye with a kiss. I walked down to Port Authority to take the bus home. Normally, my MO. was to text immediately and tell him how much I enjoyed the date, but this time I waited to see if he texted me the next day to see if he was interested, especially since the night didn’t end exactly smoothly. Only time would tell…

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Human Resources Part II

This is a follow-up post to the earlier “Round 2” post…

HR and I were finally able to set a time to go on a second date.

This time, we agreed to go to Industry, a popular gay club in Hell’s Kitchen, after work. I had never been before, but this was happy hour on a Monday, so my fear of gay clubs was a little easier to get over.

I walked uptown to his office and waited for him to finish his workday. When he came down, I noticed he obviously changed his clothes. He wore a suit to work every day, and today, he was wearing very tight brown pants and a polo shirt. He looked gayer than a $2 bill. Yes, I know how bad that sounds.

Thinking back, I think it was then I realized we weren’t a match. Maybe that makes me shallow, but I’m really more into masculine guys. However, I still didn’t completely write him off.

We got our drinks and found a comfortable couch to relax on in the back of the bar. We talked casually, facing each other. I was trying to convey a more flirtatious body language. I could tell he was doing the same. After some time passed, I placed my hand on his leg when talking to show my interest.

Out of the blue, one of the drag performers began practicing “her” sets. Drag queens make me feel very uncomfortable, but I’m cool with them as long as they don’t try to interact with me. I don’t need to be a part of the show. When I thought it couldn’t get more awkward, the drag queen came on in nothing but a feather boa barely covering the necessary parts. HR and I discussed drag queens and our feelings about them. I respect them and their choice. I admire their confidence in themselves and their apathy towards others’ judgement.

We talked more, but then the night began to get a lot more physical. At one point, I just went in for the kill. We were facing each other, and I took the opportunity to kiss him. After our missed opportunity to kiss last time, I decided one of us needed to make a move. I usually never have the courage to do so, but tonight, I was properly lubricated and just went for it.

We spent a majority of the rest of the night kissing and cuddling. He had his hand in the top of my polo and was rubbing my chest. He expressed how much he enjoyed it, and said, “Even if you tell me to stop, I don’t think I will. Your chest feels too good.” I was enjoying it, so he had no complaints from me.

Before we knew it, it was 11:30. I couldn’t believe how late it was, and I needed to get home. He both walked over to 9th Avenue, kissed, said goodnight and went our separate ways.

I expressed how good of a time I had that evening, and we talked about seeing each other again…

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