Posts Tagged proud


After much planning with CK‘s friend, Operation Diversion and Surprise was well under way. I successfully threw CK off the scent, even though that meant making him feel like none of his friends love him. I really did feel bad about that. CK truly cherishes the close friends he has. To feel that none of your closest friends care enough about you to spend the evening with you is a bit heartbreaking.

After ensuring CK would be surprised, I went back to work. I needed to get everyone in gear to ensure I would be able to leave in time to pull this surprise off.

As the end of the day was approaching, I was looking good on time. The man I loved was going to get the surprise he deserved.  When my day was ending, I contacted CK to tell him I was finishing up. I told him to come up to Chelsea Market in a cab, and I would hop in before riding up to his apartment.

As I was finishing up at work, I realized I didn’t get CK a card. I’d already bought him a birthday present. A week and a half earlier, I bought us tickets to see Once on Broadway for his birthday. We really enjoyed it, however, in the cab on the way home, we got into a big argument. It severely tainted the night. We were having a great night out, but it turned sour very fast. After some raised voices and a little pushing and shoving, I was ready to head home for the night, but better judgment kicked in. I wanted this night to be special. I wanted this to make up for ruining his “birthday” night out with me.

I quickly ran across the street to Chelsea Market to find a shop to buy a card. Luckily, I quickly found the perfect card for him. As we got more comfortable with each other, we began breaking wind in each other’s presence. It started off innocently enough, but it quickly escalated in days to the point of no inhibition at all. You can obviously see how appropriate the card was.

Just as I was coming back outside, CK pulled up in a cab. I was texting CK’s friend to talk timing, and it was working out well for everyone involved that we were running a few minutes behind. Apparently, all his friends were banking on us running late. They truly know us all too well. This was a big relief. I didn’t know how I would convince CK to hurry up and get ready if just the two of us were going out to dinner. I told him I had a reservation, but I didn’t want to raise suspicion.

We got back to his apartment, and got ready. CK wasn’t the only one getting a surprise that night. I was shocked when he got ready in record time. As we walked out the door, he commented, “Baby, we’re doing really well on time!” I agreed with a big smile and gave him a big kiss.

We walked a few blocks, and I still wouldn’t tell him where we were headed. When we got to Q2, I walked up to the door and opened it for him. He was very pleasantly surprised. “Baby! You picked this because we ate here when I moved in, didn’t you!? You’re so sweet!” I simply replied, “Yup,” as I motioned for him walk in ahead of me to discover his friends. Only problem was, he didn’t notice them. He began talking to the hostess to get us a table for two. That is, until I tapped him on the shoulder and pointed to the big table of all his friends.

I can honestly say, until that moment, I’d never seen CK so happy. He was purely ecstatic! Everyone stood and gave him a big hug. “I can’t believe it! You guys really pulled it off! No one has ever surprised me before,” he said as he was handed flowers. CK’s friend and I shared a sideways glance that simply showed how proud of ourselves we were.

The night was a blast. We all sat and had a lovely meal together. Everyone was happy and smiling and having fun. CK’s friend’s mother even called to sing him happy birthday over the phone. When we finished eating, we all made our way back to CK’s apartment a few blocks away to get ready to go out for the night.

After getting changed, we made our way to Therapy and Industry. We stayed out dancing until the lights came on and the bar shut down.  CK looked like he was having the time of his life all night long. We snapped a lot of pictures that night, and looking back, everyone was having a great time.

I think I successfully made up for the botched birthday present. Not only that, I accomplished one of my life’s goals of throwing someone a surprise present. I couldn’t think of a more worthy man than CK to receive that surprise. We all had a truly exciting night out together. I felt a little guilty for making CK feel so low that afternoon, but in the end, I think we gave CK, the man I love with all my heart,  a night he’ll never forget.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


One Giant Misstep for Mankind

Tuesday arrived, and that meant back to work after the holiday weekend. It’s always harder to get back into the groove when you’ve been away from the office for some time. Everything takes just a little bit more effort.

That morning, CK and I woke, and although we didn’t have sex, we certainly fooled around a bit. After showering together to conserve water 😉 we got out the door at a decent hour for once. This is quite an occasion for us. It’s normally tough balancing our responsibilities and our libidos, but at times, we manage to master the scale.

We both needed a bit of help getting through the day, so a Starbucks pit stop on the way to the office was essential. We hopped in the long line waiting to order a caffeinated beverages. I would have taken mine intravenously through a central line at the door if given the option. Alas, we filled the time with chatter amongst the two of us. That is, until one of my coworkers walked by.

This wasn’t just any coworker. This was a coworker I’d been on many pitches with. She is one of the biggest names in my agency, running a global piece of business across multiple agencies. Over time, she’d grown to be a fan of mine, but not without hiccups first. Days earlier, her husband entered the hospital with heart issues. This was the first time seeing her since we heard of the incident, so I wanted to giver her space. Anyway, enough back story.

She passed me with two coffees in hand, and we said hi to each other. She sat right next to where CK and I were standing in line. When her son came and joined her at the counter, she took a second to introduce me to him. We shook hands, and they went back to enjoying their morning. In the five seconds for all this to transpire, I panicked.

I am not “out” at work. A few coworkers know I’m gay, and I assume most/the rest suspect. But, in that moment, I didn’t know how to handle the introduction of CK. He was standing right next to me, and in my panic, I acted like he didn’t exist. I failed to mention him at all.

I didn’t want to say, “Oh hi! And this is my friend, [CK].” If he’d done that to me, I would have been quite offended. We were much more than friends. This was the man I was in love with, not simply a friend.

On the other hand, I didn’t want to say boyfriend. I didn’t think that was the moment I came out to her. When the time came for me to be courageous and stand up as who I am, I was a coward.

I try to be strong and proud of who I am, but sometimes I really disappoint myself. I have tried to keep some separation between my personal and work life, but standing there with CK next to me, I should have stood proud. It didn’t matter what I said. She knew who he was in the end anyway.

CK was very upset. We’d had a discussion about my poor introduction skills over the weekend, and then I pulled that stunt. I knew instantly he was upset, and I knew I failed. I started to talk to him about it, but I could tell he was fuming. We talked about it for the rest of the time we were in Starbucks, with the exception of the moments we stood in silence because of the tension. As we walked to the subway/my office, the conversation continued as I explained what happened and how I panicked. I also explained that I wasn’t making excuses for myself, and this was something I needed to get over. I am going to be gay for the rest of my life.

In the end, he understood and accepted my apology. I asked for his patience. I have only been out for two years. He, on the other hand, has many more years on me being openly gay. I even went as far as to publicly chastise myself in Twitter that day to show him how sorry I was. Earlier in the weekend, we discussed opening our relationship up publicly to Twitter. I’d admired how @AustinWilde and @AnthyRomero send each other messages and love across Twitter. I wanted to share that with CK. We started sending each other messages publicly expressing our love for each other. When he sent out the message, “@Onegayatatime baby, i love you,” I melted a bit. As a joke, I responded, “Who is this?” He didn’t appreciate the humor, and immediately deleted the tweet. From the other room, I discovered this and asked him about it. He was angry, and I began to cry. That message meant the world to me. It was the first time he expressed his love for me in a public forum, and it was gone. Or at least I thought so. I did, however, manage to save it by screen-grabbing my phone before it was gone forever. We both took a step back and realized what happened and how much we loved each other and moved on.

That day, CK met my old coworker who left to go work at his agency. After meeting him, she reached out to me to tell me how cute he is. I was thrilled. She’d heard me talk about him quite a bit when I first met him, and now she finally got to meet him. After messing up the morning, failing to share my joy and the love of my life with a current coworker, at least I could share it with a previous one.

That night, we discussed going to an event together, but in the end we didn’t go — I think possibly out of anger for the morning. We spent the night apart. I filled my free time with a late night run. As I ran along the waterfront in Hoboken, I wondered what he was up to in the city. Any time we were separated, I wondered what he was doing with a twinge of suspicion. It was hard not to. Guys in my past treated me poorly, so my self-esteem was very low. The thought of me not being enough for him was not so far-fetched, however, I just left these at suspicions. I never acted on them or accused him of anything. They were simply figments of my imagination…

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


Sexual Exploration

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…

Friday afternoon, I was talking to J, one of my closest friends. We swam together in college, and I can actually say I think we’ve grown closer with each other now than we were back then. He’s a great guy and I cherish our friendship!

I recently had the pleasure of attending his wedding, but before that, we had a little chat:

He asked if I wanted to see what he bought his future wife for their honeymoon. Before he sent me a link to The We Vibe, vibrator for couples to use together, he included my typical warning message: WARNING: The following post may be too graphic for some. I thought this was hysterical, and I was proud of his level of comfort in regards to his sexuality. Apparently, he’d been dying to say that to me for some time. From there, a whole new conversation spawned.

He told me of his extensive toy bag. When I told him I owned none myself, he responded, “DUDE! You gotta get toys!” I really never saw a need for these. I was enjoying the “toy” God gave to every man I brought into my bed.

Then the conversation took a turn. “Ahhhhh, perfect time for me to ask you opinion…” he said sending me this link: It was to a prostate massager for men to hit their G-spot. “Thoughts?” he added. My head immediately went to the Tickle My Tush book I’d received months earlier for review. I told him to remind me the next time he was in Hoboken, I’d lend it to him. He told me, “Been looking at the Aeneros. Clearly for me, but I’m butt hesitant.”

I was proud of him for even considering the idea. The butt is a region many straight men fail to explore because it is seen as taboo. It is an entirely new erogenous zone that should be explored, even by heterosexual couples.

They’d explored this idea in the past. She was comfortable, but he wasn’t. “It’s not a gay thing — Just uncomfortable,” he typed. I told him not to be hesitant, but I also encouraged him to explore alone before engaging his future wife.

I explained to him how I’d never really explored back there myself before coming out. Of course I’d used a finger in the bathtub to see how it felt, but I could never get over the uncomfortable sensation. I never derived pleasure from that region, with the exception of oral pleasure. “I don’t really get off from traditional penetration,” I told him. “It gives me nothing. But… I have had great experience with a finger… It can be more directional and targeting, and I have gotten off from that fairly often”

He told me, “See, we tried finger like years ago — Freaked me out… Didn’t/couldn’t relax. Haven’t tried it since” I immediately added, “You need to get comfortable yourself alone first. Then, you’ll be more relaxed.”

Somehow we got sidetracked, and we began exchanging thoughts on different brands of lube. I’ve always used water-based because I care more about my sheets and don’t want stains. He suggested using a towel and explained how much better silicone is. He even went into the chemistry of it (which is his background). I knew why he liked silicone better, but when he would be on the receiving end of silicone, he might not have the same feelings about it after learning of its lingering effects.

Soon, we were back on track. I asked him if he had a tub. I explained: “Some day… take a bath…  warm water… and relax. Lay back in shallow water with your back on the bottom of the tub, legs up on the brim. Gently penetrate with your. It takes A LOT of getting used to. You need to feel like your pushing out to allow things to gently come in. You’re going to feel like your going to sh*t yourself… You probably won’t. It’s a natural urge you need to combat. It’s def. awkward — No question about it. It’s just a matter of getting to know a part of your body you’re not used to engaging.” I told him the book I was lending him would talk all about it.

He responded, “Fair enough. Makes sense too.” I told him I would bring the book to his wedding in a week. He asked if I could please wrap it up before doing so. I joked at the idea of simply putting it in the box of cards in hopes his mother was the first to get to that. He added, “I appreciate this. You have a hell of a lot more experience than I do.’’ I replied, “Yes and no.” I reminded him how I was never really a bottom, but I was certainly exploring that a lot more in my current relationship. “Clark Kent and I have a very healthy flip relationship,” I supplemented.

He retorted humorously, “Didn’t say you were an expert (I do read you blog), but you know a hell of a lot more than I do.

I thought back to my first time. “It was very different and awkward. It took a lot of getting used to. And, when someone told me about the push thing, it got a lot better. And, then when I read it in the Tickle My Tush book, it confirmed that for me. She describes it very well,” I detailed.

“You know this is goin’ in the blog right?” I asked. “It won’t say J — Just a male friend. But, I’m very proud of you!” He responded, “Hmmmmm. Go for it. This is J. You don’t have to keep it anonymous. I’m not scared. I don’t mind. Just give me a heads up right beforehand. A healthy sexual appetite and willingness to explore are healthy things.”

“But again… I’m very proud of your willingness to explore without worrying about social connotations. This is definitely a longer conversation I want to share sometime,” I added. We agreed to revisit this topic again when we both had more time…

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


Comedic Timing

Every morning I woke up happier than the day before. I had an amazing boyfriend who would only make my day brighter. On top of that, I had an amazing new bed. I couldn’t believe the different a solid platform bed made over a standard metal frame. I slept so well, I slept through my alarm. I woke Wednesday morning at 9:00am. I was going to be late for work!

When I got to work, I solidified my plans with CK for the evening. I was planning to run home after work to pack an overnight bag, but after texting with CK, I learned he was planning to spend the night at my place. We would meet at his place before hitting up the show. He was hoping to get home by 7:00. As the day progressed, he informed me he would be lucky if he could leave work by 8:00. I decided not to run home. Instead I hung at the office and write a few blog posts.

When 8:00 hit, he headed home, and I made my way over as well. He was going to hop in the shower, so he told me he’d leave the door unlocked. When I got to the door, it was locked. I buzzed, and he answered in his briefs. I ran and threw my arms around him, and we had a five-minute makeout session. He was a bit sweaty and told me how gross he was. “I smell like balls,” he added. We both fell to the bed in tight embrace and began rolling around the bed.

I was so happy to see him. I had missed him, but seeing him made it seem all the more extreme. I was downright giddy. We playfully rolled around the bed kissing each other all over. CK proceeded to continue to bite me. I told him to stop.

I finally laid down the law a bit. I told him how much it hurts. I explained that nibbling was okay, but the biting was starting to leave black-and-blue marks. He calmed down a bit. He then proceeded to attempt to pin me down so he could playfully put his smelly balls on me. I playfully resisted and protested. Luckily for me, I’m stronger than him. Finally, he made his way to the shower. I sat on the couch reading until he emerged. We fooled around a little more before finally making our way to snag a cab to the Lower East Side.

When we got to the event at the Upright Citizens Brigade, I realized this was something organized through work. It was a packed house. It was difficult to maneuver through the full bar, especially with my work bag and CK’s overnight bag. That’s when he kinda let me have it. He pointed out just how much he hates carrying a bag around. He originally wanted to swing by his place on our way to my apartment. I suggested bringing his bag with him since we’d already be downtown. He also pointed out to me how he wanted to drop his bag off at my apartment when we were walking through the festival that Sunday, but I didn’t make that happen. I offered to carry his bag then, and I offered to trade bags with him at the event since mine was very small and light.

In the end, it was fine. He got over it and thanked me for taking care of his bag while he grabbed us drinks. We were seated shortly, and it wasn’t that much of an inconvenience.

The show was hysterical. I recognized an old coworker in the crowd and someone I went to college with on stage. He was the best of the whole lot. I was very impressed. It was nice to do something fun with CK.

When the show was over, he was ready to head out into the rain. We grabbed Mexican at a restaurant around the corner. It was very good and we have a good time sharing a bunch of tacos and flan. We talked about how we met and how lucky we were to find each other. We also talked about the hot bartender. I noticed him when we arrived but didn’t mention anything. It took CK until we were ordering dessert to notice and pointed it out to me. He was surprised to hear I’d already noticed him.

We hopped in a cab to the PATH and made our way to my apartment. We barely made the train. I didn’t know he needed to buy separate trips for the PATH from the MetroCard, so I quickly scanned my card for him while holding the train doors open so it couldn’t leave.

As we walked to my place, I opened my umbrella, and he asked if he minded if he locked his hand on my arm. Again, I felt slightly uncomfortable, but I needed to force myself to get used to it. This was my life. There’s no changing it. I was curious what made him ask that. Was I that bad at hiding my unease? I told him it was fine. He also wanted to see if he could figure out the way back to my place without help. I was impressed when he pulled it off.

When we got to my apartment, we went straight to my bedroom. It was late, so we both stripped down to briefs and boxers. It was nice to lay in his warm embrace finally. It really made my night. It wasn’t long before we started fooling around. This of course led to sex. “Do you want to f*ck me?” he asked. I expressed me strong desire to, but then he flipped it on me. “Can I f*ck you?” he added. I agreed, and we got it on. (I was very happy to see the bed hold up so well and not make a sound. It truly was a worthwhile investment.)

We both lay there incapacitated for some time before he asked if I wanted to f*ck him. “When I get feeling back in my legs, maybe,” I said. In the back of my mind, I was saving my turn for the morning. I’m always horniest then, and it’d been a while. I knew it would feel amazing.

Instead, we started to watch Revenge. About ten minutes into the show, he was gently snoring. I woke at 4:00am to find the TV and lights still on. I turned them off and tucked us in under the comforters.

Waking in the morning to his smiling face in mine was priceless. We kissed immediately, and I felt amazing. I really liked CK! He was everything I needed in a man. I didn’t have one single complaint about him at that moment. He was spectacular.

Warning: The following may be too graphic for some. After a lot of cuddling and snoozes, he began blowing me. It felt great, but I was really hoping for penetration. Finally, positions shifted, and I found the great pleasure of being inside him.

The time came to get ready for work. He needed to be there by 9:00 and put me in charge of making sure that happened. He went into the bathroom for some time before he emerged and asked if I wanted to join him in the shower. I obliged his request. Who could turn down such a sexy man with hot water streaming across his body?

We ended up leaving the apartment slightly late. I flagged us a cab to make up for some time, and we managed to catch the PATH just as it was about to embark. I kissed him at Christopher Street station and said goodbye.

When I got to work, I was already missing him. The previous night, he mentioned his disappointment in not being able to be around for my birthday. I told him I understood. His mother was coming into town. I thought it was very sweet of him to be disappointed, especially since I don’t really celebrate my birthday. I sent him a text to let him know I missed him. He responded telling me he missed me too, and he was having a very productive and good morning. I was happy for/proud of him.

I was really falling for him. I even took a moment out of my day to update my status on Facebook to reflect my new status. I couldn’t be certain where things were headed after only a month, but if things continued the way they were going, I certainly was onboard! Maybe I would finally find love.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

Leave a comment

Flip the Crazy Switch

I woke Monday morning to find myself all alone. After spending nearly forty hours straight with CK, it’s no wonder I felt alone. Two mornings in-a-row I woke in the embrace of an amazing man who made me utterly happy.

Utterly happy until I became utterly confused. I still had no idea where the conversation came from Sunday afternoon. He peppered the weekend with some of the thoughts he had about taking things slow, but this conversation came out of nowhere. I was not putting pressure on him to put a label on things. I never mentioned anything of the sort. I wasn’t even becoming clingy or stalkerish.

Almost always, he was the one to pick up the phone and call. I would send the periodic text message, but I was always sure to do so sporadically. Since Wednesday night, when he mentioned the need to talk to me about something in person, I’d been walking on eggshells. I was also slowly preparing myself for just this type of news.

I had lots of questions. A large part of me wished he never brought up the subject. Who was this other guy? How does he fit in the picture? So far, all I knew about him was they met around the beginning of the new year, they would see each other about once a month and go out to dinner as friends, and they would do things as more than friends. We were not exclusive. I’d known him for two weeks. I never had that expectation. A part of me knew that wasn’t the case the moment he blocked me on Grindr.

The fact that this was a policy made sense on paper, but when you look at the emotional collateral damage that policy has, it seems absurd. If he was so happy with me, why did he need to be on Grindr at all? Was he still getting sex out of his system? Fine. Not happy about it, but I get it. But a time will come when he’s going to have to $hit or get off the pot. I don’t wait around forever. My timeline, if anything, has shrunk after guys like Smiles stringing me along for three months. There would come a time when I would have to be enough for him, or I would be nothing for him.

I have to say, I was a little shocked with how well I was handling this. I was so proud of how much I’d grown. Normally this kind of information would make me a nervous wreck. My mind would be closing gaps between spotty information with whatever it chose to create. Maybe my suspicions would be on point. Maybe they’d be way off base. Maybe I’d make another assumption and cheat on him like I did with N. That was not going to be the case this time. I was stronger. My expectations were far more realistic. I was not following A’s advice of continuing to keep up a roster, but he was. I was okay with that. But there comes a time when you have to settle down and narrow the field to one. Who knew when that would be?

It was so contradictory as well. That afternoon, I received a text from him saying: “Baby, I can’t get you outta my mind. And, I’m totally ok with that. Hope you’re having a good one xoxo.” It’s obvious he was interested in me.

After an awesome workout at the gym, I left feeling confident and happy. It was a good workout. I kept thinking about how I wanted to look good for CK, but also, if things didn’t work out, I’d be a sexy man waiting for the next guy to sweep me off my feet. This is what was different about me. I wasn’t emotionally putting all my eggs in one basket.

I came back to my office and chatted with J on gChat. I told him the situation, and he was just as perplexed as I was. He saw the same picture painted I did. He also came to the same conclusion: “I have no idea how you should proceed,” he said. It was then I decided the best thing for me was to ignore the conversation completely. We weren’t at that place yet to have that talk. I wasn’t going to face what he told me until I needed to, which J pointed out to me would be in about two to three weeks based on my typical timeline. I agreed that around one to one and a half months in, I would get restless and need answers.

That evening, I was writing blog entries. I picked up the phone numerous times to call CK, but better judgment kicked in for once. I put the phone down, after stalking his Twitter account a little and went back to writing. That’s when I received a call from CK. He was at a work event and took the time to call. We made tentative plans Sunday morning for me to spend the night either Monday or Tuesday. I had been curious if he’d call and if our plans would stick. Indeed they did. He asked if he’d see me the following night. He had tickets to a Johnnie Walker scotch tasting. Little did he know how good friends Johnnie and I am. He asked if I’d be his plus one and suggested we grab dinner and go back to his place after. I agreed, and he asked if he could call when he got home later in the evening to give me more details. One thing I have to give him credit for, he was incredibly considerate and when he said he’d call, he always delivered. That is until that night. He never did call. I’m not going to lie when I say my imagination was already getting the better of me. However, I couldn’t make any assumptions.

This time, I would be brave and speak my mind. I wouldn’t wait two more months at the sake of a failing relationship just so I had something to hold onto. No. This time would be different. This time I knew what I wanted, and I was going to get it – If not from him, than from a more deserving man.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


From Metropolis to Hoboken

On April 20th, my blog turned one year old. I didn’t even realize the milestone was coming up until I looked back at the calendar on a whim one day. I felt the need to celebrate, but I hadn’t told Clark Kent about my blog yet. How could I tell him I wanted to celebrate something I didn’t feel comfortable sharing with him yet?

Instead, I celebrated privately with messages from friends and readers on the blog and over social media. I also had a date night planned with CK.

I invited him to come out to Hoboken for an evening ride on the bike since we weren’t able to do so the previous Sunday. This would be the first time he came out to Hoboken and would see my place. I was quite excited. I came home for work early after a pitch and made sure my place was acceptable.

He had to work slightly later and had to swing by home before he came over. It was a Friday night, and he would be spending it in my bed. As time passed, I sat on the couch patiently awaiting his arrival as the clock ticked on. I had no word from him. I tried calling, but no answer. Where was he? What was he doing? What was taking so long?

Since I was a little broken from previous relationships, my mind began to get creative with where he may have been or what/who he may have been doing. Finally, I convinced myself to put those thoughts out of my head. They weren’t born of any behavior he exhibited. They were simply a spawn of his presence on Grindr. I needed to learn to trust again. The thoughts were gone, and all I could think about was seeing him.

He finally arrived in Hoboken around 8:00. I wanted to watch the sunset with him. The way it reflects off the city skyline is breathtaking, however, the sun had completely set. We’d be taking a ride in the dark.

I picked him up on the bike at the PATH, and we set off along the waterfront to the palisades of Weehawken. I wanted to show him a spectacular view while taking the bike out for a spin. He’d been so excited about it ever since he first learned of its existence.

I really relished having him ride behind me. He pulled himself in tight against me. It was incredibly romantic, and I loved how he wrapped his arms around me. I felt like a great protector.

When we got to the palisades, we parked the bike and took a short stroll along the cliff. We talked while hugging and kissing each other with the spectacular NYC skyline in our periphery. We happened upon a family taking pictures of each other with the city in the background. He offered to take the picture so everyone could get in the shot. I thought it was incredibly sweet of him, and I fell for him a little more at that moment. Every moment with him made me want him all the more. Again, I wouldn’t let myself get too wrapped up in him. It was still early. I didn’t even know if he was interested in a relationship, let alone one with me.

After taking the picture, I told him about my desire to prank tourists in NYC. I would offer to take a picture of them. Just as I was about to snap the picture, I would turn as if to run. When they began to chase after me, I would turn around and snap a picture. It would give them a great experience and a fun story to tell for the rest of their lives, and they’d have a picture to accompany it. He thought this was brilliant and commented on his desire to do this himself.

That’s also when I told him about my life’s to-do list. I told him I wanted to share it with him later because it spoke volumes about me.

We made our way back to the bike and decided to grab dinner back in Hoboken. I knew of a great spot everyone had been telling me to check out but had not been to yet, Bin 14. We rode down the hill from the palisade and made our way back to Hoboken along the river.

I found a spot to park, and we walked to the restaurant holding hands. I wasn’t yet comfortable doing this in Hoboken, but it was something I needed to get over. I would be gay for the rest of my life. If I wasn’t okay showing affection in public, I was in for a lot of headaches going forward. Since we didn’t have a reservation, they asked if we minded sitting outside. I preferred it actually. However, this posed a new situation for me again. We would be street side, and if I wanted to show affection, all of Hoboken could see — Or at least that’s how it felt.

Slowly but surely, I got over this. I was rubbing his knee under the table and exchanging kisses over our meal. I didn’t care who was looking. I still felt a little self-conscious, but I was proud of myself for getting over this.

After discussing wine at length, we agreed upon a nice bottle of Malbec. It took us some time to figure out how to order from the tapas like menu. We still hadn’t figured out our sharing dinner groove, but it was fun to learn this together. I came to find we shared a lot of the same tastes and likes. It also helped we were both share quite an adventurous palette. We ordered a few plates and told the waiter we would continue to order until we had our fill.

The food was great, and the conversation was even better. I was still getting to know him, and I was mesmerized by his smile the entire meal. I was gaga for this guy. If it turned out he wasn’t interested in pursuing a relationship with me, I was going to be heartbroken. I was past the point of protecting myself. I’d already cracked the candy shell. Now, I was in his hands.

We declined dessert, and I made sure to give the waiter my credit card to pay the bill before CK even had a chance to think about it. This date was going to be my treat. I liked this new system. With all the other guys I dated, we both threw down our credit cards and split everything. This felt more like dating and more like a relationship. Each date felt special because one of us was treating the other to it.

We hopped back on the bike and rode back to my apartment. When we got there, it was already fairly late, so we headed straight to my bedroom. I was just finishing removing my shoes when he shoved me backward onto my bed. Since it was up on risers, the bed shifted to the side and collapsed. He was so scared he’d broken my bed, but I assured him it was already an issue. This had already happened with N once before. I’d already been searching for a new sturdy bed not on risers, and this would be the impetus that forced me to address the issue with much more vigor.

We fixed the bed as best we could and continued to make out. It’d been a week since we were last together, so of course we were both horny for each other. I hadn’t had sex since we last saw each other, but I wasn’t sure I could say the same for him. We hadn’t crossed the monogamous relationship bridge yet, and I had no right to ask that question yet. We’d only been dating a week. One step at a time I told myself.

Warning: The following may be too graphic for some. Regardless, we found ourselves naked, and I was grinding on his backside. Our passion was elevated to a new level, and we were all over each other. I couldn’t get enough of his body — It was purely amazing. I’d never been with someone so handsome, so sexy, so fit, so sexual. He was like nothing I’d ever experienced before.

Eventually, he reached behind himself, grabbed hold of my manhood and directed it in until I found myself deep inside him. Amazing sex ensued until we both had our fill.

I was incredibly happy once again. I had a man who could come to dinner and hold a great conversation, and a man who could satisfy all my sexual desires. He was the best of both worlds.

With that, we cleaned up and climbed back into bed. I was happy to finally be sharing my bed with him. This would be the first time in a long time my California king was being put to good use. We fell asleep in each other’s arms. He was my little spoon. Throughout the night, we changed positions many times, but never fully woke up. We slept great.

When we woke in the morning, CK had to head back into the city to begin apartment hunting. He’d been putting it off and needed to put his nose to the grindstone. We stopped for a delightful breakfast at Ganache while we got to know more about each other. When we finished, we rode through the Lincoln tunnel into the city. I couldn’t drop him in front of his building because there was a parade going up his street, so we said goodbye to each other in front of the Empire State Building. I couldn’t think of a more romantic way to begin my Saturday…

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


Southern Hospitality

After my lukewarm date with the doctor, I was ready to get back out there in search for a man.

I’m happy to report, which I’m sure some of you may have suspected otherwise, I was doing a great job of staying off Grindr. Granted, it was a short period of time, but I was thoroughly proud of myself. I felt like I’d joined GA. Every day not having meaningless sex was another day of Grindr sobriety.

Tuesday after work, I arranged another date with Southern Drawl. The last date was a bit crazy. Footsie under the table. Shenanigans in the bathroom. I was curious if he’d be able to behave this time or would he be looking for another quick trip to the bathroom.

We texted during the day to lock things down. I proposed The Breslin. I’d always loved their food, their drinks and their ambiance. He shot the idea down because he said the place was always full of hipsters. I had always been a fan of Sala 19 in the Flatiron District, so I proposed we go there for dinner. It worked out well because it was halfway between our offices. He agreed.

I had to wait at work for him to finish. When he did, I made my way south to meet him. I met him on the street corner, and we walked to the restaurant.

Dinner was very nice. He was well-behaved, and the conversation was good. I told him about my allergist appointment, and he told me about his day. We talked frankly about our last date. We discussed what went on. I learned he’d never done anything like that before. I was also learning about the guys he’d dated since living in New York City. When we originally spoke on the phone, I was under the impression he was new to the gay world. I thought he’d never really dated anyone before. Now, I was learning about all the guys he dated in NYC, as well as the guy he dated through college that he said I so strongly reminded him of and resembled. It was a bit unsettling.

In the middle of dinner, he told me he’d ended things with the guy he was seeing. He explained they’d only been seeing each other for two weeks, and things were never that strong. When I probed him to ask if he left the other guy because he met me or if he did it because he wasn’t satisfied with the previous guy, he told me it was the latter, but part of it was also due to meeting me. A big red flag went off in my head. Would he leave me for a better model?

I still wasn’t sure about him. I liked talking to him. I liked being with him. He was smart. He was nice. He wasn’t flamboyant, however, I wondered if maybe he was too “straight.” He was a bit homophobic. I’m not the most open about my sexuality. I’m not out to everyone at work. I don’t openly advertise my sexuality. However, if he wasn’t comfortable with himself, how could we be comfortable with each other. I couldn’t be sure about him. Was he right for me? I had no idea. Only more time could tell. I was keeping a distance as we moved forward. We had a connection, but was it strong enough to last? Was it what I wanted?

In our conversations, his southern entitlement shined through. It was an incredible turnoff. Where was the southern charm I’d seen so many times in movies. When I think of the ideal man, I think of Matthew McConaughey. He definitely has an ego and self-confidence, but he also exudes charm and sexuality. His confidence is not in your face, and he seems down-to-earth. Southern Drawl fit the other Hollywood archetype — The Southern plantation owner. He had an air or superiority that was hard to swallow. Many times, he laughed off these comments, making them seem like a joke, but I wondered if there was really something deep down that was more genuine. I wasn’t ready to date a snob. That $hit wouldn’t fly with me. I wasn’t going to let him get away with it, and I’d already started calling him on it.

When we finished eating, we split the bill and walked north to the PATH station. I said goodbye to him ont he street with barely a hug. He was uncomfortable exchanging a kiss with me in front of a city of strangers. I wasn’t thrilled by that.

On my ride home, I questioned why I was continuing to see Southern Drawl. He was definitely interested in me, and I was still intrigued by him. I wasn’t ready to write him off just yet, but I didn’t see a lot of promise or potential. I would continue to see other men and continue to see him until I was ready to make a definitive decision.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


Revisiting the Past

Relationships aren’t easy. No matter whether you’re friends or lovers, each relationship is accompanied by its own set of issues. When you introduce sex into these relationships, things get exponentially more complicated.

Tuesday, I engaged in unprotected sex with M.E. It happened in the middle of the night in the passion of a moment, however, there is never an excuse. People’s lives are at stake. I tell you about the poor decisions and the mistakes I’ve made because I hope you can learn from them.

From that morning on, I was on damage control. I’d already talked to him about what transpired between us, and we agreed to get tested and share our results to ensure we were safe going forward. I called a doctor’s office and made an appointment that Wednesday following work to have an STD test.

As I walked into the doctor’s office, I noticed a few other men sitting in the waiting room. I had never been to this facility before. I was curious if they were there for the same thing I was. I began to wonder what was going through their heads. Were they petrified? Were they already infected? etc. I myself began to worry a little. I wasn’t particularly worried until I walked into the waiting room. There was nothing I could do at that point, so I tried to calm my nerves. The only good part about this was it made me quite ready to fill a cup with my urine sample. They also drew blood and told me to call in three days for my results.

Now, it was the waiting game. I couldn’t do anything and would have to wonder for three days.

That night, I had plans with P to go see Silence, The Musical. After my tests, I walked all the way downtown to meet her for dinner near the theater. Dinner was very nice. I got her caught up on all the latest action in my life. She’s always incredibly supportive, even when I make poor life choices.

We went to the show, and about two minutes in, I noticed how attractive one of the male actor/dancers was. It was a small theater, and any time he was on stage, I couldn’t take my eyes off him. When they came out for curtain call, he caught my eye, and we made eye contact. There was a bit of an awkward moment, but I was crushing a bit.

I wasn’t intimidated because I’d already dated someone who worked on Broadway. This was Off-Broadway. I didn’t think twice about what I was about to do. That night, when I got home, I decided to do some research (and when I say research, I mean stalking). I pulled out the Playbill and looked to see if I could find him on Facebook. Much to my surprise, he was on there. I decided to message him. What the hell, why not? What did I have to lose?

I’m sure you’re wondering who this is, and I really hope this doesn’t come off incredibly creepy. I myself can’t believe I’m about to send you this. (And, something tells me I may not be the first).
First off, I came to see Silence tonight and thought you were incredibly cute and incredibly talented. Your mother must be so proud.
Second off, I have no idea if you’re single or even gay. But gay or straight, single or taken, I’d love to strike up a conversation with you. On the flip side, I fully understand if this makes you uncomfortable. 
Anyway, with nothing to lose but a little dignity, I thought I’d give it a shot. Hit me back if you’re interested in chatting some time. If not, enjoy the flattery…

Then, I noticed he was a friend of Broadway, the guy I dated for ten months. I pulled out my phone and texted him to see what their relationship was. His response was, “Who is that?” I explained who he was and how they were Facebook friends. “Oh yes. We audition together. HOT!! You dating?” I told him, “No. I just cold called him on Facebook after seeing his show… LOL. We’ll see what happens. Think I creeped him out?” He felt I did creep him out, but I explained how I had nothing to lose.

Sadly, I never heard back from him. It just wasn’t meant to be.

Much later that night, I received a text from the guy I had sex with when I cheated on N. We’d been texting a bit recently after noticing each other on Grindr. He asked if I was up. I replied, and he asked if he could come over. Apparently, I was getting a booty call. It was about 11:30, but I didn’t see the harm. After all, I did fantasize about the first time we had sex quite often. It was something my mind went back to many times. This isn’t because of the cheating. It was simply because the sex was that good.

He came over, and I could tell he’d been drinking a bit. He immediately commented on how crazy it was that my new apartment looked exactly like my last. He began taking his shoes off before hopping on the bed with me. He immediately began making out with me interspersed with conversation. He never got closure with how messed up things ended between him, N and myself.

He wanted to talk a lot about him. I would have been fine if N never even came up in conversation. I learned they got together once after I told him to take a hike. It was hysterical how much their accounts of this encounter were completely different. The only commonality was how much disdain they had for each other. At one point he mentioned how dirty N was. I asked him to clarify as in physically or as in naughty. He then went on to describe a particular body part that would only have been encountered during sex and how disgusting it was. He then went on to tell me they never had sex. He told me N just gave him a blowjob and he finished on his face. He pointed out his surprise I ever dated N. N’s account of the story was they met on the street. After seeing him, he couldn’t believe I would hook up with someone so ugly, let alone cheat on him with someone of that caliber. All I could do was laugh my a$$ off in my head. These two were ridiculous. I was so happy I cut things off with both when I did.

After the N conversation concluded, he really wanted to have sex with me. He mentioned how amazing it was the last time we hooked up, and he told me he hadn’t had sex with a man since the previous summer. I told him how hot it was last time we hooked up and how I referred back to it many times in my mind. With that, the clothes began to strip off.

Warning: The following may be too graphic for some. We were intertwined in each other’s embrace making out. I found myself lying on my stomach with him on top of me. I knew he would try to penetrate me, but I wasn’t game for that. The last time he did that, I sprang from the bed because he did it with no preparation and full force. I wasn’t about to let that happen again. He tried and tried, and I never relaxed to allow entry. I think he got embarrassed with his fumbling, and he made a comment. I complimented him and told him he was too large for me. We switched positions, much to his chagrin, and now I was the one on top. He was on his back, and I put his legs up on my shoulders.

He told me how much he enjoyed me inside him because I hit his prostrate just right. With that, I slipped inside him. It felt amazing. It was just as good as the last time I played over and over again in my mind’s eye. He loved it too. After a short while, he finished on his abdomen. Seconds later, I alerted him I was about to finish. He replied, “I want you to shoot inside me,” and I did. For me, this was a first, and it felt incredible.

I’m not sure why, but I had no problem finishing this time. It completely came naturally and without over thought. I felt amazing and incapacitated all in one. We lay there next to each other speechless for a minute before even moving or talking. We were in euphoria.

When that wore off, I became the topic of conversation. N told him about the blog when everything went down. He told me he read part of it and still didn’t understand why I wrote it. He also asked this story not make an appearance, but I find it too important to exclude. He pointed out I was looking for a boyfriend, and that was not what he was looking for at all. He pointed out how I was going about things all the wrong way if I wanted to find love. I explained to him all my trials and tribulations and what I was looking for in the end. He fully understood.

Then he made a comment about how stupid we were to not use a condom. I agreed. I’m sure he was far more worried about the situation than I was since I finished inside him. Apparently, with everything I’ve been through, I still didn’t learn my lesson. I wasn’t being responsible.

This was my wake-up call. I’d hit rock bottom. I’d gotten so reckless with my life. I needed to stop before I did something that could end my life. What was I doing? How could I be this stupid? This wasn’t how to find love — Having unprotected sex with the guy I cheated on my ex with. No more excuses. No more Grindr hookups. No more strangers. If I wasn’t finding love, I would be single and celibate for some time until I got myself under control. This was my turning point.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,


Leavin’ On a Jetplane

Another Monday. Another day at work. My staycation was officially over. Another day periodically checking Grindr.

I spent my vacation getting myself back. The only problem was I only repaired the physical me, not the mental and emotional me. I wasn’t on Grindr all day long, but I would periodically check it to see if anyone had messaged me. I was simply a Grindr fish. No longer would I be a fisherman.

I had a dermatologist appointment in the middle of the day. While walking to my appointment, I fired up Grindr. I was curious to see if anyone was scoping me out. I was also in a new neighborhood. I was hoping to find something new and unexpected. In the short window it took me to walk about twenty blocks, I’d managed to strike up a conversation with three different guys. All seemed to be quite level-headed. I told them all I was looking for dates, and all of them seemed excited at the prospect. It was difficult trying to keep three conversations going at the same time. I told them I was walking into my appointment and asked each of them for their phone numbers. I managed to pick up a lawyer, an actor and someone who worked for a magazine rating cruise ships. I asked each of them for their pictures to add to my roster and went to see my doctor about lightening up a scar.

When my appointment was over, I thought I’d make my walk seem shorter by checking messages on Grindr once again. A guy near my office was on and started messaging me. He seemed pretty hot and well fit. He was staying at a hotel near me and was anxious to give head. I told myself not to even continue the conversation, but once again, I found myself thinking with the wrong head. I entertained the idea and asked him what he was proposing specifically. He told me he had to catch a flight in a short while, but wanted some fun before leaving New York. I immediately knew which hotel he was staying at and his occupation. “You’re a flight attendant staying at the Radisson, aren’t you?” I asked. “Yea. How did you know?” he replied. “Not the first one I’ve talked to at that hotel. You guys love that hotel, and you guys love Grindr. So what exactly are you looking for?” I texted.

He asked me to come to his room. He would leave the door ajar. I would walk in, he would tear off my pants and just begin orally pleasuring me. I wouldn’t have to touch him or do anything to him. He just really wanted to blow someone. I knew better, but I still bit anyway. I figured, “What’s the harm?” Work had no idea how long my appointment would last, and it was a slow day at the office. I decided to take a detour, but I basically had to run to his apartment. Thank God I have long legs to get me there. He was anxious because his checkout was very soon.

He was very worried about STDs and HIV. I assured him I was clean. I also asked if I would be allowed to play with his manhood if I chose to. He enthusiastically said yes.

I arrived at his hotel in time for an afternoon tryst. I hopped in the elevator and made my way to his room. I’d been here before. This wasn’t my first b.j. from a flight attendant at the Radisson. I really needed to stop making that a habit, but at the time, I was excited to get off in the middle of the afternoon. I arrived at his room, and the door was left ajar.

Warning: The following may be too graphic for some. I walked in and said hi. He immediately began lifting my shirt and sucking on my nipples. I lifted my shirt off, and he undid my pants. Just then, he turned to me and asked, “You’re really clean right?” I assured him I was. “You can never been too sure,” he added.

He began pleasuring me. After a few minutes, I made my way to the bed and laid back. I wanted to fully enjoy him. It wasn’t too long before he worked his magic, and I was able to conjure up exciting mental images. I shot in his mouth and all over his face and chest. He spit on my chest and began working on himself. Seconds later, he shot all over my leg. “Let me grab you a towel,” he said immediately. I wasn’t moving. I was quite anxious to get both of “us” off me.

I cleaned up and began to exchange small-talk with him. He was Austrian and was headed home that evening shortly after I would be departing his room. I needed to get back to the office, and he needed to finish getting ready for work. He told me how much he enjoyed himself, and with that, I made my way out the door.

Shamelessly, I had a smile from ear to ear. I was still high from the endorphins. It felt amazing. I was ashamed and proud in the same moment. I still knew I was broken inside and needed to stop having these trysts with strangers, but I was also enjoying my sexual liberation. Somewhere, there had to be a happy medium. It was up to me to find it…

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

Leave a comment

Connecting the Dots

Just because I said I wasn’t going to hit up Grindr constantly in search of sex from strangers didn’t mean I couldn’t satisfy myself with guys I’d already been with. This way they wouldn’t be strangers.

The last time I visited the bar manager in Hoboken, I had a great time. He had an amazing body, and we both really enjoyed each other. Wednesday, when I woke, he happened to be around. There had been a few days I suggested we get together, but he was always heading out-of-town for something. This time, he was available. There was a small snafu. He was sick. He had a sinus infection, so he was worried he’d get me sick. I told him it would be alright. We would simply avoid kissing each other. He told me to come up to his place, and he’d break out the glory hole again.

This visit was pretty much the same drill as my last visit to his apartment. He left the door unlocked. I was to walk in, undress, and saunter up to the hole in the sheet hung in the bathroom doorway. He was waiting for me on the other side. I hopped on my motorcycle and made my way to his place. I did as I was told.

Warning: The following may be too graphic for some. I removed my shorts and inserted myself into the opening. Immediately, he grabbed hold and began to orally pleasure me. It felt amazing. I wasn’t fully into the glory-hole thing, but it was making it a little more exciting. It wasn’t long before I pulled the curtain back once again. We started kissing each other all over each other’s bodies and swapping back to him on his knees. He was wearing his hat, which I’d already knocked on the floor so I could grab hold of his long flowing hair and his boots. It was an incredibly sexy look for him, and he knew it. I couldn’t keep my hands off his body.

He turned around and began grinding his backside against my crotch. I was incredibly turned on and excited. It felt so great to simply have his back pressed against my chest with one hand pulling across his chest so keep him close and the other pleasuring his impressive manhood. We continued this action until he was so excited he finished all over the bathroom floor. Everything felt amazing, and I was very close to finishing myself. However, this didn’t happen.

Once again, we moved things to the couch. He was all over me and everything felt incredible. I wanted to finish for him so badly. He was awaiting it with great anticipation ever since I first fooled around with him. We played for quite some time, and I kept losing my erection and gaining it again when I would pleasure his endowment. Throughout the whole visit, we were incredibly tempted to kiss, and came close many times, but at the last second withdrew again.

When a large period of time passed, he threw in the towel. He had to get on with his day. He was disappointed, and I was too. Not only disappointed, but also embarrassed. I wanted so much to please him. I wanted to give him exactly what he was looking for, but I came up short.

He walked into the bathroom and threw on a pair of sweatpants. As he walked, I could see his manhood swinging back-and-forth. It was such a turn-on. This is one thing that will always get my engines revving! He loved walking around with his package easily visible as well. It was something he was proud of, making it all the more sexy. I walked up to him and grabbed hold of it. I wish this was something I could do on the street. It would be so hot!

As I got dressed, I made a point to look around a bit. When I last left his place, I suspected he lived with his partner. I indeed confirmed my suspicion when I noticed there was only one bedroom. I also tried to casually scope out the pictures on the wall. The apartment was not decorated like two random roommates living together. It was definitely the residence of a loving couple. I felt a pang of guilt. This guy seemed like a good guy. I was disappointed in him for cheating on his lover. I didn’t know the dynamic between the two, but I never liked seeing infidelity. I wasn’t passing judgment, but I was putting myself in his mate’s shoes. I was a partnered man’s affair. Now I knew why we never had full penetration.

I said goodbye and made my way home. This would be the last time I would see him. I wouldn’t be the last time I chatted with him. He happened to sign on to Grindr about a week later. I was checking to see if I received any new messages and messaged him just to say hi. He was in Miami. I asked him if his man came with him, and he told me he was at home. Without knowing it, he slipped up and confirmed to me he had a man in his life. I pointed out to him how I caught him in a slip-up. When he originally mentioned the guy, he told me it was his roommate. He acknowledged his lie, and I told him we were cool. I had no hard feelings. It was his life, not mine. I then realized he was probably on Grindr down in Miami looking for a new piece of tail. I told him to enjoy himself, and with that, I said goodbye to him for probably the last time.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ,

Leave a comment