Posts Tagged lonely

FINALLY!

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…

Saturday had arrived, and it was St. Patty’s Day. I was out early in the morning to hit up the gym. I wasn’t going to find myself wasting another day lying around my apartment looking for sex. It was the true start to my staycation and to the new me. It was gorgeous outside, and I was motivated.

As I left the gym, I ran into K and one of my other friends. They were heading into the city to drink, but I wasn’t interested. I’d just come from the gym. I’m not a fan of day drinking to begin with. I said goodbye and continued on my way home. D’s girlfriend was up from Philly that weekend, so I texted them to see what they were up to. They were grabbing brunch and had no plans for the rest of the day. I told them I was bored and lonely, and if they thought of anything, I’d be game. I also called my old roommate to see what he was up to. He was studying for yet another test he had to take for work. I knew it was useless to try to convince him to do anything else.

Finally, D and his girlfriend decided to swing by. They came up, and we just lounged around chatting. She’d never been to my apartment before, so I showed her around. After some time, we decided to go for a drive and check some new cars for D to possibly lease. I was game, so we made our way uptown in the great weather to D’s car.

We decided to drive around Jersey City since there were a few nice neighborhoods I’d never explored. I was a bit curious, and the other two were as well. I also wanted to scope out a spot I had in mind for dinner that night with the guy I spoke to on the phone for two hours, Travel Agent. We drove by the cute cafe on the corner in an upscale neighborhood of Jersey City, The Hamilton Inn. I’d seen it a few times before and had been curious how it was. I pulled up the menu on my phone and suggested the idea to T.A.

He was still working, but he said it sounded like a good idea. We planned to work out the rest of the logistics later.

We drove around for quite a bit more before finally returning to Hoboken. They dropped me off at home. I hopped in the shower and began to get ready for the evening with T.A. I’d been texting him a bit and made a reservation at the restaurant for 7:00. When he told me it’d have to be later, I called and changed the reservation for 8:30. When the time came, he picked me up in his nice Audi. He was a good-looking guy. He wasn’t someone you’d stop on the street and say, “Damn!” but he was good-looking. We jumped right into conversation. It was fairly relaxed. I feel he may have been slightly uptight, but I tried to remain candid and relaxed.

The Hamilton was exactly what I was hoping for. It had a decent crowd, the food looked and smelled amazing, and we got a nice table to sit and chat with each other. The obvious and easy thing to decide was to order a bottle of Malbec to share. I still couldn’t help feeling he was uneasy about things. He just didn’t seem to relax. I tried to lighten things up and asked if he wanted to split an appetizer. He agreed, but it wasn’t terribly easy to pick something. He defaulted to me, and after discussing it, I finally decided on the pierogies with goat cheese appetizer.

We began by talking about where we grew up in more detail than we discussed on the phone. The conversation shifted to our jobs. I got to learn in greater detail what he does. I told him about my job, and slowly I began to realize I was monopolizing the conversation. He’d ask me a question, and I’d answer in detail. When I’d ask him questions, his answers would be short. I wanted to get to know him. He seemed like a decent guy.

The waiter returned and we ordered. I was debating between he risotto and chicken. I decided on the chicken, and he decided on the risotto.

We talked some more until our food arrived. Or should I say, I talked some more. I would never say it was a bad date, but I would also not say it was a great one either. We shared some of our meals with the other. It was a nice time. I was enjoying his company, and the food was delicious. I was looking forward to a second date so we could think of something more relaxed to do. Hopefully that would break him out of his shell.

We declined dessert since he had to get home because he had a big work project the following day. He expressed to me how much he enjoyed the date. I was happy to hear it. We split the tab and made our way back to his car. On the way back to my apartment, we passed another restaurant I was interested in trying. I mentioned it to him, and he said, “Maybe next time we should try there.” That was a very hopeful statement. If he was already thinking about next time, maybe he really did enjoy it too.

We stopped in front of my apartment, and he put the car in park. He leaned over and gave me a kiss. I pulled back and went in for a second. It was nice, and I wanted him to know I was interested. I told him, “Call me when you’re back from Mexico. Or, you can text/call whenever you like,” with a smile as I exited the car. He told me we’d be in touch.

After that, I heard nothing from him. He clearly stated his enjoyment and mentioned a second date. How was I not supposed to think he was interested? I sent him a text to tell him of my good time with him, but I got no response. I checked Grindr, and sure enough, he was online. Clearly he was ignoring me. I messaged him on Grindr as well. When a day passed and I heard nothing back, I decided he would either deny this or the “relationship” would be dead before it began. “I hope you’re not ignoring me. I thought you were a classier guy than that.” He had given me two different phone numbers, so I asked if I was texting the wrong number. Finally, he responds explaining he was busy and apologized. He told me he was interested in seeing me again as well.

However, after that, I didn’t hear from him again. I know when I’m not particularly interested in a guy, I don’t outright tell him that. However, I don’t talk to him about future dates to lead him on. It was very disappointing, but I wasn’t going to let one guy get me down. My Grindr diet was slowly working. I was back to concentrating on dates and not sex. Hopefully, with enough time, I’d find a good guy to settle down with — Someone to be the reason I delete Grindr forever…

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Shout From the Rooftop

Today is a Fast Forward Monday!!!  

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 spending the day with The Navigator at the beach and then sharing a pretty spectacular relaxing evening together, I slept great. There was a sexy naked man in my bed, and I knew just what to do with it. We fell asleep spooning each other. When I woke in the morning, I couldn’t stop smiling when I realized it wasn’t a dream.

I still had to bring myself back down out of the clouds to keep myself in check. This wasn’t going to last forever. I didn’t care. Right now, there was a man in my bed, and he needed to be cuddled.

I rolled over and pulled him close to me. He was still slipping in and out of sleep. As he woke up, we picked up just where we left off the night before. Everything we did was fun. We were constantly ribbing each other and joking around. When we ended laying face to face, I said to him, “I just want to climb up to the roof and shout, I love my best friend, [The Navigator]. Boop!” as I reached my finger out and tapped him on the nose (an homage to Super Bad).

We both laughed for some time. We continued to cuddle all morning. I didn’t care if I stayed in bed all day. I was happy.

We were interrupted by a call from his roommate. I’d already learned he was a really good friend, and he liked to placate his friends. While he was on the phone, I took out my camera and snapped a few pictures of him lying naked in my bed. I don’t think he realized what I was doing because he had his back to me, but I wanted some souvenirs to take home with me.

Turns out, his roommate wanted to go to the grocery store that afternoon. They share groceries, so he regrettably turned to me and told me he had to go with him that afternoon before we went hiking. I was very disappointed, but I wasn’t going to make a stink about it. I quickly hopped in the shower and got ready for the day while he packed up his things and got dressed. As we walked out the door, I pointed out the Marilyn Monroe portrait saying, “My week with Marilyn.”

I drove him home and dropped him off. I was already sad to see him go even though I knew it was a matter of hours before I’d see him again. I grabbed some lunch and made my way back to the pool. I relaxed with some light reading. I needed to finish off the Tickle My Tush book so I could write my review.

When most of the afternoon passed by and some noisy kids arrived at the pool, I texted him to see how he was progressing. He was on his way home, so I decided to go get ready to go hiking and make my way over to his place.

I pick him up, and we take a short drive to the base of the mountain. I grab my camera and we make our way up the trail. When we get to a decent height, he suggests we climb back down part way and hit up another trail that had a much better view. We were having fun just being together. On our way back down, he pointed out a shack along the trail: “I wanted to surprise you, but this is going to be where we live when we get married. :)” While he said this, he took hold of my arm. I knew he was completely kidding, but it was also a sweet gesture.

When we got to the top of the other trail, we had quite a view. We could see LA and Burbank off in the distance. He took my camera from me and took some pictures of me. Again, I thought this was a sweet gesture, as were many things he did. He was just very conscientious. You didn’t have to ask him to do things; he just anticipated it. I was falling for him more and more every minute, but I still maintained my mental state.

I then turned the camera on him and snapped a few pictures. I wanted to remember the great guy I met in LA. I hoped we’d remain friends even after I returned to New York. It would certainly be nice to have a friend on the West Coast. Maybe I could even come back to visit some time.

We climbed back down the mountain and made our way to Burbank. We joked about PDA. We both agreed we weren’t really into it, but at one point he casually reached out his hand and grabbed my junk while looking the other way. I pointed out to him that just because he wasn’t looking at it doesn’t mean other people wouldn’t see it as well. We both laughed and continued to joke about other things. We walked around for a little bit and grabbed some ice cream. He was cold, and I was trying to do my best to keep him warm without making him feel uncomfortable. That’s when he broke the bad news to me.

He’d already prepared me for the possibility he’d have to go to work that night at 1:00am. He was on call, and they hadn’t gotten back to him yet. He needed to go home and nap before that shift started.

My heart sank a little. He wouldn’t be spending the night in my bed again. I needed to be a big boy about it though. I drove him back to his apartment and said goodbye. We talked about seeing each other the following day since it was my last day there; I had a flight out at 10:00pm.

I returned to my hotel room and watched TV in my bed. I knew he was napping, but it was make or break for me to ask him if he would come with me for my ride up the Pacific Coast Highway. After debating for some time, I decided to text him: “Lonely here without you already 😦 haha. What are the chances you’d wanna ride up the PCH with me after work tom?” I really didn’t want to take that ride alone. I loved his company, but I seriously feared a disappointing answer.

The Navigator wouldn’t let me down like that: “LOL. I know. I wish I were cuddling with you!!!!! That sounds like a swell idea.” I was thrilled. I was prepared for the worst, and I got the best. I was looking forward to tomorrow’s road trip so much more now that I had my Navigator! “Marylyn Misses you too,” I added.

Shortly after that text, he requested I send him some pictures of myself. “You’re most handsome ones,” he added. “Whom are you showing me to now?” I asked. Apparently, he wanted to show off his “super long first date” to his roommate and his other friend.

I was pretty crazy about him, but reality wasn’t absent from my brain. It did, however, bring a big smile to my face to know he was showing me off to his friends. It made me feel special and gave me hope I would have a longtime friend from what started as weak Grindr banter…

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Late Night Snack

After my tryst with the Armenian and the Asian, I decided to order some real dinner. This was the last night I was on the company dollar, so I ordered some room service. While I waited, I chatted with the guy who wanted to come by later in the night. I sat and ate my meal in bed with just the TV to keep me company. I was feeling lonely, which is such a strange emotional state to be in considering I’d just shared one of the most intimate acts with two other men.

When midnight arrived, I started texting my late night snack. I asked him what he thought his E.T.A. would be. He told me it was still up the air, but he was definitely coming by. He was out with friends and would swing by on his way home.

Finally, around 2:00am, he texted he was finding parking and would be by shortly. Ten minutes later, I had a knock at the door, for the third time in a matter of hours.

He was a very nice polite black man who was anxious to spend some time with me. He seemed very young and innocent. We chatted a bit while sitting on the bed before any action began. It was getting late, and as rude as this sounds, I was ready to get it in and go to bed. I wanted a nightcap so I could doze off soundly till the morning.

Warning: The following may be too graphic for some. We had A LOT of foreplay and prep before anything happened. He really wanted to cuddle for a long time before we could even get frisky. I was almost ready to call it quits and ask him to leave. It was getting late, and I was getting tired.

There was a lot of kissing. A lot of heavy petting. A lot of licking and sucking. Finally, he was ready and got into position for me to penetrate him. I could tell this wasn’t a guy who gave it up to just anyone. Normally, I’m really into the foreplay and making out, but I’d already had my engine warmed up earlier that evening. In fact, the car had been taken around the block a few times.

I’d saved my climax for him and quickly learned this was a big mistake. He was very bad. We didn’t go for very long because I really wasn’t getting anything out of it. Finally, I stopped and rolled onto my back. I tossed yet another condom in the trash and started taking care of myself. He laid next to me and asked me to finish on his chest. I obliged his request, and he followed suit shortly after.

I knew he was going to be a lingerer. I tried to cut that off at the pass. I humored him for a short bit of time before I finally spoke up and said how I needed to get to bed. It was past 3:00am. It was time for him to go! He got the hint and got dressed. While he did so, he asked if we could hang out again while I was in town. He told me how much he enjoyed himself. I didn’t shoot him down, but I didn’t exactly give him the answer he was looking for. I told him I’d have to see what my schedule allowed for. I told him I was trying to get the most out of my vacation in L.A.

With that, I said goodbye, shut the door, showered all the men of the night away, and climbed into bed to dream about the sunny sandy beach I would be visiting the following day.

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My Adult Book Report

Warning: The following may be too graphic for some. It is of a sexual nature. Proceed with caution!

A few months ago, the fine folks at Tickle Kitty approached me. It seems bestselling author and sex educator, Dr. Sadie Allison published her fifth book, Tickle My Tush: Mild-to-Wild Analplay Adventures for Everybooty. They offered to send me her latest paperback that helps men and women learn the true pleasures of the under-explored “seat of love” for review on my blog.

I enthusiastically accepted the offer, and anxiously awaited its arrival in the mail. I wasn’t entirely sure what I was getting myself into, but how bad could it be? I’m gay. If I had an aversion to anal play, I’d be a very lonely man the rest of my life. Maybe I could learn a thing or two from the book as well.

I wasn’t the only one anxiously awaiting my new book. My roommates were also waiting with bated breath to see what the book was all about. When it finally arrived, we all passed it around paging though to see what exciting new tips we could learn.  After we’d all had our fun like immature high school students in the locker room, I took the book back and began reading it.

Tickle My Tush is a light-hearted fun look at anal sex for mainly heterosexual couples, however, a homosexual man can learn a lot from this book. Dr. Sadie covers a lot of material in this quick read — The 14 chapters of this book cover everything from safety and heinie hygiene to toys, strap-ons, and positions of pleasure. And, Dr. Sadie takes a light-hearted approach by using playful language instead of some complicated medical jargon no one understands or uses.

This book does a wonderful job removing the stigma from anal play/sex. I can think back to when I was first experimenting with homosexuality, I wanted nothing to do with anal play. I watched it in porn, and it really just seemed like something I didn’t need. I could think of many other things I could do to satisfy my sexual urges. It was something I saw as overwhelming and uncomfortable. Frankly, I was scared of it. If you find yourself in that position, reading this book will answer a lot of the questions and will clear up a lot of the misconceptions you may have.

What I really like about this book is that it pushes straight men to open their minds and their bottoms to the idea of anal play with their female sex partners. I enjoy sex, and even as a “top,” I enjoy many of the pleasures my bottom has to offer. Having your prostate stimulated for the first time is a mind-altering experience. Many straight men don’t realize the potential their bottoms have for pleasure. I would hope books like these remove the stigma and open their minds to anal play. This book also removes the stigma for women to explore. It takes away the idea that enjoying anal sex makes you dirty or a slut. It’s simply exploring all the pleasures you body has to offer.

As you read, the book certainly gets more adventurous. It starts with safety, hygiene, anatomy and the basics and moves through finger, oral, genital, toy and strap-on pleasures.

One of my favorite chapters is 6: Sensual Booty Massage. It has always been something I’ve enjoyed. “As an often overlooked erogenous zone, those two cheeks are always eager for sensual arousal from kneading, squeezing, kissing, licking, spanking, gentle biting, father-light touching — or simply calming moments of warm-handed stillness. Why stop at the cheeks? Lustily arousing the hips, waist, small of the back, inner thighs and A-spot can add thrilling new dimensions to your lovemaking.” Some are tried and true methods I’ve been using forever, and some are a few new methods I’m dying to try.

Some of Dr. Sadie’s advise is spot on! One of my favorite parts of the book acknowledge the problem I have relaxing during sex. It’s the root of my inability to climax at times. Her best advice — UN-focus.

This book is a great read for the anal play beginner. I can think back to the guy who inserted himself with great force inside me with no preparation whatsoever. I ran out of the room in pain. I can think of the virgin who allowed me to penetrate him for the first time and how scared he was until he learned how much he loved being penetrated. I’ve been with a few newbies in my days, and there is a lot they can learn from this book. On top of it all, the illustrations that ensue are purely erotic. I think they are my favorite part of the book!

There are a few things in the book I disagree with on some level. For instance. in regard to the question, “Do you really need an enema before anal sex?” Dr. Sadie says no. But, after a few of my own horrific experiences, I HIGHLY RECOMMEND IT.

Overall, I must say, I didn’t learn a whole lot from this book I didn’t already know. That is because the first guy I slept with was a very good teacher, and I have a curious mind that has been satiated by experimentation. But, not everyone is as lucky as I am. If I had this book from the start, it certainly would have made for many less awkward situations. The thing I most learned from the book was anatomy. In fact, I often refer back to it to make sure I am giving my man the most pleasure I am capable of.

Dr. Sadie does an excellent job giving you the basic tools you need to be confident, succeed in anal play in the bedroom and know you can enjoy the untapped pleasures your bottom holds. She gives you invaluable tips that help get you in tune with your partner. She answers a lot of the embarrassing/uncomfortable things that may arise with anal play so that when you encounter them in the bedroom, you can proceed past them without the interrupting the fun. So buy it — Read it — And for heaven’s sake, try out all the new things you learn with someone you feel truly comfortable with. You’d be surprised what exciting new experiences you can unlock.

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Welcome Back?

Sorry for the late post… Had a very busy morning at work…

 

Since that fateful night on December 31st, 2011, I’ve had my eye on a certain someone. He was also attending the party I went to on New Year’s Eve.

Throughout the night, I talked to him a fair amount. He seemed like a really nice guy. For a solid twenty minutes, he and I were the only ones in the living room until more guests arrived. We got to know each other fairly well. My original thought on him was he was too young, but the more I got to know him, the more I learned how mature he was. Obviously age had nothing to do with maturity. I learned that the hard way with Smiles. I wasn’t going to rule him out just because he was 22. It also helped he was very attractive. He had both the jock look and the intelligent look about him. It was very sexy.

I didn’t want to jump the gun however. I somewhat embarrassed myself that night, and I wasn’t sure if he took notice. I decided to wait until the dust settled, especially since he knew Smiles though a mutual connection, the party’s host. Before my trip to San Francisco, I laid the groundwork. I informed him of my breakup with Smiles on Facebook. He sent his condolences.

Now that I was home, I was ready to dive in and see if I could ask him out on a date. I sent him a Facebook message that Tuesday: “Hey dude. I know this kinda comes out of left field, but I thought you were a pretty down-to-earth guy when I talked to you on NYE. I was wondering if you’d be interested in grabbing a drink sometime…?” I don’t know why, but I felt very vulnerable doing this. It’s crazy. He’s five years younger than me. Why was I so intimidated? All I could do was wait for an answer.

That night, he finally responded: “I am flattered, but I am kinda seeing someone. Happened right after New Years actually. Doesn’t mean we can’t chill as friends.” My hopes were dashed. I’d been plotting and planning this whole thing out over time to find out I missed the boat. I was kicking myself, but there was nothing I could do. It is what it is.

I needed to graciously respond, and secretly hoped I could meet him as friends, and he would realize how much of a catch I am. Maybe he’d let things fizzle out with the other guy. The door wasn’t closed, even though it was beginning to shut. There was still a glimmer of light — A glimmer of hope.

“All the good ones are… haha… but yes.. Chill as friends works for me too. Always lookin’ for friends as well. Shoot me your #, and maybe we can find a time to hang/grab a drink…” I responded.

Sadly, I wouldn’t hear back from him again. Three weeks later, I tried to see if he would be interested in meeting up, but I got no response. If he was truly interested, he would have responded. I was learning to stop pursuing men who didn’t return an interest in me. It never worked out in my favor, and it just caused me greater frustration. If there were interested, they’d be as excited as I was to message/call/text. It wouldn’t matter about waiting two days before calling. If someone is interested, they won’t care about any of that. They’ll just be thrilled you connected at all.

I was beginning to feel very disappointed and lonely. I had no promising prospects on the horizon. As time goes on, this dating thing is getting harder and harder. Everyone thinks gay dating in New York City is a cinch but far from it. It is so incredibly hard to date in this city. The gay men here certainly don’t do anything to make it any easier.

Warning: The following may be too graphic for some. In the meantime, I was back on local Grindr. I found a guy who lived very close to my apartment who wanted to be dominated and wanted to muscle worship me. I hardly think I’m the muscle worship worthy type, but if that was what he wanted, why not give it to him. I went over to his apartment. He was a bit awkward, but I wasn’t there to find love. I was simply there to satisfy a primal need. I thought I would be able to play the part. I thought I could say all the things a dominant top would say, but in the end, I think I sounded ridiculous. It’s not who I am. It wasn’t awful, but I don’t think either of us were getting out of it what we thought we would. It took me a long time to finish with him, as usual, which didn’t exactly make for a smooth evening. When I did, it was worth his wait. However, because of the nature of my climaxes, he had to run to the kitchen and grab a bottle of Resolve and a paper towel to clean up a spot on the carpet when I overshot his chest.

He came back to the bed and we laid next to each other chatting a bit. I learned he knew the other awkward hookup I had in the same building. Apparently they were friends. I specifically asked him not to mention me, which of course spurred a whole new line of questions. I knew this was going to come back to bite me in the a$s. It was only a matter of time before the 40 year-old started messaging me again.

With that, I got dressed and made my way home on my walk of shame. Luckily it was cold out and it helped me clear my head. What was I doing? This isn’t me. This isn’t what I’m looking for. Why am I doing this? Yes, we all have needs, but I should be putting more energy into finding the right guy instead of Mr. Right Now.

I thought about all the other guys floating around out there on my roster. Was it even worth it to revisit with long-time online friend after our failed date? Maybe the southern boy I was chatting with would finally find the time to meet up. The guy who came back on the roster after almost a year was still a possibility. I needed to plan drinks with him. My Asian neighbor friend from Grindr was still asking me to grab dinner sometime, but he doesn’t drink, so I didn’t see us being very compatible. There was the very sexy, very compatible guy I found on Adam, but he wasn’t responding to any of my messages anymore. I needed to cut him from the list.

I needed to get back in shape and concentrate on building a better me. Ironically enough, I was hitting the gym regularly again. For so unknown reason, I was looking for N there every time I went. I don’t know why, but something inside me wanted to see him there, even though I wanted nothing to do with him. I needed not only to close that chapter, but also to toss the book to someone else and forget about it.

I was spinning my wheels. I was constantly Grindring, and it was getting me nowhere. I was still feeling a little angry for letting Smiles take advantage of me. I thought back to all my relationships and realized how each of them let me down. N, San Francisco, Smiles… I didn’t need any of them anymore. They brought nothing positive to my life. It was time to drop that baggage. The only one I wanted to keep around was Broadway. Since we’ve broken up, we’ve managed to remain friends. I turn to him for advice, and he is always there for me. He’s a good friend and I truly appreciate him. I can’t understand why they all couldn’t be that way. I’m thrilled we’re still friends and want that with all my exs, but if they weren’t going to make that possible, so be it.

I needed to get to a better place. I wasn’t in a dark place, but I was certainly stuck in this constant gray area. I was walking around in a cloud. I was wasting my life away searching for a guy in all the wrong places. If I wasn’t happy, I wasn’t going to find anyone. I just needed to figure out how to change things. It wasn’t going to be easy…

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Put Me In Coach

It was obvious things were strained between Smiles and I. For quite some time, our relationship was on the decline. He was distant, closed off, and not very engaged, and I wasn’t happy.

I tried to stick it out with him. I tried being patient and understanding. He was a good guy, and I could see there was a great guy under all this. But, I had reached my limit. I knew I deserved better. It was time to move on.

Wednesday passed without communication from Smiles, so I sent him a text in the middle of the afternoon. “It’s apparent you’re trying to put distance between us. Can you possibly find time to discuss things with me in person? Thanks,” I typed.

He responded ten minutes later with: “I can this weekend. I’m up at 5:30 and in bed at 12:30 and not a lot of time in between. This weekend will be a littler better but not much. I will make something work though.”

Wow! It was all I could do to restrain myself from responding, “Thanks for squeezing me in!”  How could he!? After three months of dating, he couldn’t sacrifice a gym session to take the time to talk to me like a man. What a coward! It was completely disrespectful and painted a clear picture of Smiles’ true feeling for me. I doubt he ever truly cared for me. He simply enjoyed not being lonely.

I’m no one’s lap dog. I was back in the game. In my mind, we were all but broken up. It was inevitable. There was no coming back from this, especially since the relationship wasn’t the strongest to begin with. I’d been through yet another failed relationship with a man who simply wasn’t that into me. My confidence was pretty much shot. What was it about me they couldn’t seem to embrace? I’m not pathetic enough to say what was I doing wrong, but I also knew I may be something to turn these men off.

Regardless, I was back in the game. I needed to put myself back out there. Some people would argue I needed some time to be single and to figure myself out, but I know myself well enough. I didn’t need time to heal from this one. I did need to have some fun. It’d been a long time since I had passionate active sex, and I was hungry for it.

After my last breakup, I went wild over the summer. I hooked up with a lot of guys and expanded my sexual horizons. It was both a good thing and a bad thing. I didn’t want to go back to my old ways. I already learned how unfulfilling it was. There was no need to repeat old mistakes. But I wasn’t going to completely limit myself. I was “single” for all intents and purposes.

I had been talking to a Latino on Grindr for a bit of time. He seemed like a really nice guy, and we had a lot in common. Latinos aren’t really my type, but I’m an equal opportunity dater. N was of Latino background, and we got along well enough in the beginning.

We set a date for Thursday night to grab a drink at a local Hoboken bar, Trinity. He lived in neighboring Jersey City, and I convinced him to drive over since I didn’t have a car — It was a bit cold for the motorcycle.

He arrived before me, and found a spot in the corner of the bar. It was a good spot since we could talk without a large crowd of spectators. I shook his hand and introduced myself. He did the same, and I immediately recognized an accent of some sort. I asked him where he is from.

He told me of his roots in Venezuela and asked about my upbringing. I told him about my time growing up on the farm and how I came to live in the shadow of New York City.

We’d learned about our shared interest in volleyball and talked about that for some time. He was much more of an amateur than myself, but it was nice to find someone who had an interest in it.

We somehow got on the subject of coming out and families. He told me he’d been out of the closet since he was eighteen. He asked when I came out, and I proudly told him I was fresh and new. I told him I’d only come out about a year and a half ago. The expression of shock and disappointment on his face said it all. I knew the date was a failure. We chatted a bit about it, and I could tell he was not thrilled with the idea of my being a “new gay.” I tried to explain to him I wasn’t new. On the timeline, it may seem short, but I did a lot in that short period of time. I grew in leaps and bounds and had relationships of all sorts with varied men. For the first time in my life, I was trying to vaguely paint myself as a recovering whore.

When I think back about this, it was a dumb idea. If it was something that bothered him, I should have accepted that and moved on. I didn’t need to end the date then and there, but I shouldn’t have tried so hard so early to be what he wanted. I should have just been myself. This may be why I get involved with men that aren’t truly interested in me.

Somehow our discussion morphed into the topic of sex with women. He’d never been with a woman, but I have. I was just adding water to the fire with every sentence. We talked about the local gay dating ring, Grindr and the like. It was an interesting conversation, as we the entire date, but I doubted there would be a second.

When we finished that drink, I paid the bill and offered to walk him to his car. When we got there, I went in for a kiss. It was pretty bad. We pretty much crashed into each other with a forceful peck. I’m not sure why I kissed him if I wasn’t all that interested in him. I think it’s because I’ve been out of the game for some time, and I just felt like it was what I was supposed to do.

As I walked home, I checked my phone to find out one of the guys I’d met from Grindr months ago was moving to Hoboken. We’d been in touch sporadically since we originally met. He was just coming off a really rough breakup, and I was just starting things off with Smiles. I met him in hopes of making a new gay friend. I needed those as much as I needed lovers. He’d invited me to go out a few times, but I was never able to due to other plans. Now we’d be neighbors, and hanging out would be much easier. I was just what I needed to come back into my life at that moment.

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What Doesn’t Kill You Makes You Stronger

Sunday afternoon, I tried to see if Smiles would want to do something fun the following day since I didn’t have to go to work. Sadly, he had work to do. He was trying to build up a company from scratch, and it is a lot of hard work, so I understood. What I didn’t expect was he would be busy he wouldn’t be able to find the time to pick up the phone and call or text.

Monday passed with me planted on the couch watching TV all day while surfing adam4adam.com and reactivating my Grindr account. I was just seeing what was out there, but as the afternoon progressed, I started to think toward the future while examining the past.

I realized I wasn’t happy. I equated my relationship to the struggle of Sisyphus, a king punished by being compelled to roll an immense boulder up a hill, only to watch it roll back down, and to repeat this throughout eternity. I was constantly putting work into the relationship only to find I wasn’t receiving much benefit from it.

I had given Smiles more than his fair share of chances to finally woo me, and he failed. I enjoyed his company, and he was a very nice, successful, good-looking man, but the time had come to move on. It just seemed he wasn’t that into me, and I realized I deserve better. Since I had been on the journey to this conclusion for quite some time, I wasn’t that broken up about it. I’ve had varied reactions to the end of relationships in the past. I moved on with closure after my mutual breakup with Broadway. I had slight some minor cardiac scarring after I ended things with San Francisco. I was a wreck when things went south with N — Losing ten pounds in a week (Not proud of that).

This epiphany wasn’t all that earth-shattering for me. Things had been on the decline for some time. This certainly didn’t come out of the blue, so the blow was lessened.

I actually started to get slightly angry about things. I felt used. I recalled asking Smiles on our first date why he was on Grindr, and he had mentioned he was lonely. I realized I was someone to pass the time for him. I was someone he could go to dinner with so he didn’t have to eat alone. I was someone he could have the occasional romp in the sheets when he was in the mood. I was a seat warmer. He never had any plans to forge a relationship with me, and this made me really feel used.

I wanted more. I deserved more. And I was going to find more. I started searching once again on a4a and Grindr. These are clearly not the best place to find Mr. Right, but it couldn’t hurt to try. Once again, it was just going to be a lot of work.

On top of it all, our sex-life was minimal. As a result, I was horny. I was hungry for some good sex. Over the summer when I was having my wild time, I felt I started to really hone my craft. I had numerous guys constantly hitting me up for seconds, thirds, and more. It was great for my ego, and I craved a really good romp in the sack.

That’s when I turned my efforts toward Grindr. I wanted to find a local guy with a hot body. I knew it wouldn’t be easy from past experience, but maybe some new hotties moved into the area in the three months I’d been away. I started talking to one guy for quite some time. We even started to Skype with each other while I watched TV. He lived very close and had a really nice body. He was Asian, which doesn’t quite get my engine roaring so there he wasn’t a relationship prospect, but we could at least start on a friendship. We face-time chatted most of the evening. I gave him full disclosure on the situation. We even discussed him coming over to hook up, but in the end I decided to be good.

Afterall, I still hadn’t officially ended things with Smiles yet. It wouldn’t be right. I’d already betrayed that relationship once, I didn’t need to do it again, not matter how resolved I was about its end.

I got an offer from a man I’d had a tryst with in the past. He begged me to come to his apartment, but it was cold outside, and it was getting late. I had work the next day, and I needed to go to bed. I told him I’d take a rain check.

My new friend went to bed, and I continued to figure out a way to satiate my libido. I figured I would hit up some old friends in my Skype contact list. One of the sexiest men happened to be online. He lived in South America on an island, and I wanted to do bad things to his body. It was amazing. I loved camming with him. The only issue was he had a big thing for me. He always begged me to be his boyfriend, no matter how many times I told him it couldn’t happen because we are so far away. He begged me to come visit, but I told him I couldn’t afford the flight. I wasn’t about to fly to South America for a booty call. But if he lived anywhere close, I would have been over there in a second!

I convinced him to have a little fun on camera until I finished. As usual, it sapped all the energy from my body, and I jumped into bed and dozed off without a thought left in my head.

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Not Every Day is Eventful

After I learned my lesson with cheap haircuts and learned how much more I can spend on top of the original cost to have them fixed, I decided to pay more attention to who was cutting my hair.

The opportunity arose for me to purchase a Living Social for the New York Shaving Company for a haircut, a shave and free shaving cream for $36. I jumped at it because I was about due for a cut. My hair had grown in considerably since Smiles and I had the barber fix it in Brooklyn. The location of this establishment was also an added bonus — Not far from Smiles’ apartment.

I decided to get a new cut before New Year’s Eve, so I made an appointment for Wednesday night following work. I figured I would get cleaned up and then visit Smiles before heading home for the night. We’d texted during the day and I told him of my plan to get a cut and shave and told him I would try to swing by after since I was in the neighborhood.

I have to say, I was really impressed with the place and they did a great job. I was quite uneasy with the cut immediately following because it was so short. It was shorter than the last time, which was a bit of a change for me to get used to. Now I was going even further. It also made me realize the chill outside since I was far less insulated from the bitter cold that night.

As I walked through the streets of SoHo carrying a side table in a large box I’d ordered and shipped to work, I pulled out my cellphone and called Smiles to see if he was home. My hand and face froze in the bitter cold as we I waited for the phone to ring, but I got no answer. After two short rings, it went to voicemail. I knew he’d “sidebarred” me.

However, I was upset for not, because a minute later, he called me back. He apologized for hitting the wrong button when picking up the phone. He was trying to run around to get ready because he was meeting a friend for drinks. I tried to see if he’d be home for another five minutes, even if all I got to do was say hi and give him a kiss, but alas, he was already running late. I was disappointed I wouldn’t get to see him. He did promise to call me later that night before going to bed.

I course corrected for the PATH and made my way back to Hoboken, but not before texting a few other friends to see if they’d meet me for dinner at the Village Pourhouse in Hoboken. I had a Groupon I needed to use up, and it was late. I didn’t want to go home and cook dinner. I also didn’t want to be alone. After not getting to see Smiles, I felt a little lonely.

I quickly stopped home and dropped off the table. I said hello and goodbye to my roommates and made my way to the Pourhouse. D and K decided to come meet me for dinner. It was nice to see them and catch up. I hadn’t seen them in some time.

After dinner, I went home and watched TV. The time came for me to go to bed, but it would be without a phone call from Smiles.

I went to work the next day and learned Smiles was attending the opera that morning from his Facebook status. Considering he took me to the opera a few weeks earlier, I was curious who he was there with. I started to become suspicious, but I had no grounds.

Then I felt quite guilty when he called me during intermission to see if I was available to step away from “work” to grab lunch. I was thrilled. He never did this sort of unplanned thing. I told him it wouldn’t be an issue at all, and we picked a place to meet. It looked like my prayers of him finally asking me on a date were answered.

I decided to take him to Kyo Chon. I’d gone there before on a friendly lunch with a guy I’d met on Grindr and rather enjoyed it. It wasn’t that great this time around. I could tell Smiles wasn’t all that happy with it either. His wings were a little hotter than he could handle. He started sweating in front of me.

After we finished out lunch, Smiles was on the lookout for ice cream. He pulled out his phone to search for it. We walked to a Baskin Robins, but he wasn’t thrilled with the idea. I told him about the Ben & Jerry’s in Macy’s Herald Square, and he was much more content with the idea of that as long as time allowed for me to continue to be away from work.

I took him on a mini tour of Macy’s after we got ice cream to scope out some of the areas. I’d always liked the 1½ floor there. It’s the “designer” floor, and the people there have always taken great care of me, acting almost as a personal shopper. He was turning his nose up at the commercialism of it as if they weren’t “real” designers. I don’t buy all my clothes there, but to me, all I needed was the Ralph Lauren section to keep me happy.

Smiles was talking about his need to revisit his energy specialist, but he was debating whether to go home and go later because he needed a nap. He called to see the hours and learned he’d have to kill an hour somewhere or come back up to midtown later. I invited him to come up to my office to kill time. I wanted to show him our penthouse in the shadow of the Empire State Building, but he had decided on the nap.

I said goodbye to him and he hopped on the subway south.

That night I went out with friends. I thought about Smiles while at the bar and decided to text him, but got no response. I was being a good wingman to a friend that night, so I concentrated my efforts on that.

He texted me back in the am to tell me he stayed in for the night studying. He planned to go shopping for the day, and I didn’t hear from him for the rest of the day. I called him because I wanted to discuss our plans for New Years, but I got no answer. We messaged each other on Facebook briefly that night to tell me he was going out with a friend. I still didn’t know quite what we were going to be doing to close 2011. I didn’t need to know for any reason, but I was curious what was in the plans.

This was another night he’d be going out with his friends and I mine. I started to think about that. He’d never invited me out for his boys’ night out. He never asked about my nights out in Hoboken with my friends. If we were in a relationship, we’d be meeting each other’s friends at this point, but that wasn’t the case. It seems we weren’t in a relationship at all. All the pieces were coming together, but I wouldn’t get the final piece until New Year’s Eve. That would be my gauge on how to proceed. It appeared my timeline had a new distinct end. Or would it be a beginning?

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Visit From the Closet

As I watched my roster shink over the summer, I began to revisit old friends. Adam4adam.com came back into my daily routine. I noticed I received a message from a 28 year-old guy who was still in the closet. His profile read: “Just lookin around, new to hookin up with guys and not out at all, so not really sure where I’m at right now. I do know I’m definitely extremely discreet and expect the same. Other than that, just playin it by ear.”

I knew this guy was going to be a delicate dance. His picture looked pretty good, and I was interested, so I reached back out to him. We exchanged a few emails about our current situations and talked about how fresh we both were in the gay world. I think that’s what he was looking for. Throughout every conversation we had, he stressed his need for discretion. I explained, “I spent 26 years in the closet. If anyone knows discretion, it’s me.”

We never made any plans during any of our initial conversations, but on a random Friday night, I found myself not interested in going to the bar. I had the apartment to myself, and I was bored so I hopped on a4a to check my messages. He happened to be online at the time, and I happened to be very horny, so I told him to come by. He had to shower and drive to Hoboken, but he was game.

This wasn’t my first rodeo. I was finally comfortable with these situations (not that that’s a good thing), and I realized I didn’t need to put in so much effort. When he arrived, I was sitting on the couch in gym shorts and a tank watching Jurassic Park. I poured us both a drink, and he joined me on the couch. We had casual conversation for a bit. Surprisingly, he made the first move. He put his hand on my leg when we were talking and left it there. As the conversation progressed, we stopped paying attention to the movie and began making out on the couch. Shortly thereafter, I pulled him over so he was straddling my lap, and we began an intense and fun make-out session.

When things got heated, and we were down to our boxers, I took his hand and led him to my bedroom. The boxers came off and the real fun began. We both had fun exploring the other’s body. He certainly was no Adonis, but he had a tight body nonetheless. I was enjoying myself, and he seemed to be as well.

At one point, he asked if I wanted to attempt penetration, but added a big disclaimer about his complete lack of experience in that realm. He was skeptical it was actually going to happen, and because of his comment, I knew it wasn’t. If that was going to be his first time, it certainly would take more prep. Five seconds after my initial approach, our suspicions were correct. He apologized, as he did a lot in bed. He was embarrassed by his lack of experience, but I actually found the role of teacher satisfying. I wasn’t the first guy he slept with, but I also wasn’t at the end of a long list, that’s for sure.

I often think back to everything I learned from Broadway and how absolutely patient he was with me from the start. I always try to embody that when dealing with someone new to the gay world, both in the bedroom and out.

When we realized penetration wasn’t going to work, we moved back to foreplay. After we both finished, we cleaned up and laid next to each other talking. I wasn’t thrilled with this. I wanted to have sex, not a long dialogue about being a closeted gay. However, I’d never be so rude as to say that or scoot him out the door. He was fresh, and I needed to be gentle with the delicate situation. I was also trying to find someone I could call on regularly for sex instead of random new guys all the time, so I didn’t want to do anything to mess this up. We talked for a half hour before he realized how long we’d been chatting. We got dressed and went back out to the couch to watch TV.

He sat down and I laid my head in his lap. It felt very comfortable, and I certainly didn’t mind that. He pet my head while we talked and watched TV. Eventually I fell asleep in his lap until he woke me to tell me he was heading home. I apologized for dozing off on him, but he was actually quite delighted it happened. I walked him to the door and kissed him goodbye.

He was a really down-to-earth guy and a big sweetheart. I liked him, but not enough to want to date him. And, the whole still in the closet thing was not something I wanted in a relationship.

Going forward, I was still searching for my unicorn, but in the meantime, he would become my go to on those lonely horny nights…

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Bon Voyage

Memorial Day was approaching quickly, and I had no plans. Anything I did at this point was going to be a staycation. I checked with my neighbor, and his plans were to go down to the shore for the holiday weekend. He left that Friday and came back the following Monday.

I was in the midst of trying to find new roommates and a new apartment. I scheduled multiple showings with my broker to see apartments that day, all the while trying to monitor craigslist to see if I got any hits for prospective roommates. Needless to say, I was stressed.

I really needed a distraction from my crumbling home life. My apartment is for sale and could be bought any second, and both my roommates were moving out. I felt all alone. I went for a long hard run since it was such a nice day. I figured I could at least put the nervous energy to good use. But when I finished my run, my anxiety returned.

That night I had a BBQ and invited a bunch of my friends over. One of my best friends since moving to Hoboken, her roommate, 2 other girls they brought into the group, and one of the girl’s male friends visiting from San Diego all came with wine in hand. My sister and one of my other good friends, K, also joined the party with ample supplies.

The BBQ was nice and got my mind off things for a time, but it was still in the back of my head. I posted to facebook my unhappy status, “Feeling very alone right now.” North Carolina read this and immediately texted me.

“Feeling pretty down? What’s wrong? I’m feeling pretty alone myself right now…”

We exchanged texts. He was missing the man he met while on vacation in Florida. I explained my roommate situation. He jokingly said that he’d move in, but wouldn’t be able to until July 1. He explained that his gay roommate was making very inappropriate passes at him, and it was making him very uncomfortable. He sent me some of the messages, and my jaw nearly hit the floor. I called his bluff and told him to move in. This wouldn’t be the first time he was slated to move in.

We talked back-n-forth for some time, and I convinced him to come out to the apartment for a BBQ the following night. I invited my sister, K, D, and his girlfriend L as well. We had another great time with food and wine all night. After we ate, my sister, K, and NC all went out to the bars. We bounced from dead spot to dead spot, the whole time bonding with NC.

We talked about Grindr and our hookups and the guys we were pursuing. We talked about winging for each other and how great it would be to live together. We also chatted about the status of my relationship with my neighbor, a coworker and previous hookup of his. At the time, they were not getting along. Both of them thought they were better than the other, and their egos were getting the better of them. NC told me I was a gook-looking guy, and I could do much better than him. He told me about the night they hooked up, which I would later find was contradictory to the other party’s recollection of the night. However, I was really happy with where the situation was headed, but I wouldn’t relax until he signed a check.

He ended up spending the night in my roommates room. When I got him settled in, and went to my room, I noticed he never closed the door. He is a very attractive man, and I definitely had some sexual attraction to him, but he was going to be my roommate. I don’t sh*t where I eat. I wasn’t going to make a move. I laid in my bed wondering if I would hear a knock at my door. But none came, and I drifted off to sleep.

The next morning, he woke and had to be back home early. He borrowed a T-shirt, and we walked towards the PATH. I was meeting some of the girls from the first BBQ night. As we walked, he sounded 99% committed to moving in. He had to make sure he could get out of his current place first. As we went to say goodbye, I extended my hand for a handshake, but he pulled me in for a hug. It was a very nice gesture and was very appreciated.

Memorial Day was spent lounging on the pier in Hoboken trying to get some color. My neighbor and I had been texting most of the day, as he was on his way back from the shore. Before heading home, he came and met me at the pier. We sat and chatted a bit, and he talked with many of my friends.

That night he came over for dinner and spent the night. It was very nice getting to see him after being away. We had a nice time both in bed and out.

That Wednesday I was slated to go to Memphis for an important business trip. After him being away, I wanted to see him the night before my business trip. I knew I’d be gone for the next 2 days and would be stressed. I wanted to get some quality time in with him.

The next morning, I finished packing while he got ready for work. We said goodbye and decided we would talk later in the day. He was very supportive and sent me texts wishing me luck on my trip. This was really starting to feel like a strong relationship.

P.S. North Carolina would eventually not move in because he got a job with a consulting firm and moved back home to save money until he got placed on a project… Fool me once, shame on me. Fool me twice, shame on you!

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