Posts Tagged awkward

Reset Button

After an arduous morning dealing with a nasty hangover and an overly energetic Hip, CK and I managed to finally emerge from our hibernation. But, not before we washed away the stink from the night before.

CK and I have been saving the planet for months now. Whenever we showered, we conserved water by showering together. We helped each other ensure all our crevices were clean. We brushed our teeth and got ready to face the world outside.

We decided to head toward Central Park, but we never quite made it there. Put an establishment like Shake Shack in front of three hungover guys who love to eat, and the rest of the world disappears immediately. We hopped in line and discussed at length all the food we were going to consume. Shakes, fries, burgers… The works! As we were paying, CK suggested we take our food to go and enjoy it outside. Hip and I agreed. When our food was ready we grabbed our shakes and sucked them down like someone might steal them.

We were out the door headed straight to Rockefeller Center. It was actually shaping up to be a nice day. We sat on the benches in front of 30 Rock Center and watched the tourists while we ate. In true CK fashion, he found a group of Spanish-speaking women who were visiting and needed help getting everyone in the group shot. I was simply happy to be out and about in the sunshine rather than being cooped up in CK’s apartment. It was a good distraction. Surprisingly, it was actually helping me get over my massive hangover. That, and the greasy burger and fries and a milkshake. While I was slowly getting over my hangover, I wasn’t quite getting over the night before. I suppose I was putting on a decent face, but deep down inside, I was hurting. I was appalled by how CK treated me after dating for three months.

When we finished eating, CK explored all of Rockefeller Center taking pictures as he moved along. Hip recently had hip replacement surgery, and he was starting to feel it. I kept him company as we sat playing Where’s Waldo in the crowd of people to find CK. When he circled back around, I hinted to him that we should go so Hip could get off his feet. He still had to head back to Brooklyn as well.

On the walk home, CK proposed we try to go to the concert again. I wasn’t so sure I was up for it. I told him we’d discuss it when Hip left since he already expressed his lack of interest in trying to go again.

When it was just the two of us again, we discussed things. Like I said, I still wasn’t quite over the night before, even if we did discuss it that morning and fooled around. When I got it all off my chest, we discussed the concert that night. CK was scheming to get in some way, shape or form. He was hoping to sweet-talk the ticket collectors into letting us in. I told him I would go, but I made no promises how long I would stay, and in full disclosure, I told him I certainly wouldn’t be the most energetic with the effects of my hangover still lingering.

We got ready and made our way to Terminal 5. When we got to the door, CK did all the talking, but it was no use. They weren’t feeling sympathetic at all. The person in line behind us, however, was. While CK was busy sweet-talking, I began chatting with the guy behind us in line. He asked if we needed tickets, and when I explained what happened, he offered us his two extra tickets at no charge. CK was still arguing with the ticket collectors when I finally got him to shut up. I handed them our tickets, and we walked in the door. CK had the most confused look on his face as I explained what happened. We immediately thanked the guy in line over and over and over again. It was truly a generous gesture — A serendipitous moment.

We made our way inside and both grabbed waters from the bar before finding a spot to watch the concert amongst the crowd. Our luck was really turning around, and CK was being extra sweet. It was like night and day from the previous night. I think it was then that I was beginning to forgive him.

When the concert started, I got a little more energy from the crowd. I suppose it was a little infectious. We danced shirtless and laughed and had a good time. Scissor Sisters really do put on a good show. They’re one of the most genuine bands I’ve ever seen perform. You could tell they were having as much fun as the crowd was. This was the final night on the final stop of their tour, and they played it out. There were even points where CK was on my shoulders with me jumping up and down. At one point, CK cut through the crowd like a razor to get to the stage as Jake Shears began crowd-surfing. He came back incredibly excited he touched his hand.

Throughout the night, there were guys aggressively grinding up on my a$$, but I ignored them. However, they started getting a bit more aggressive and overt. I didn’t need this. I was there with my man, and this was quite obvious for all to see. I gently pushed back and then took a big step forward so they could clumsily lose their balance and fall backward. After a few rounds of this, they got the hint I wasn’t interested nor a poll to rub their a$$ on.

At one point, I noticed the assistant of the guy I dated ever so briefly before meeting CK. It was a bit awkward after all. Things didn’t exactly end on good terms there. I avoided eye contact, but as he was leaving, he stopped to say hi. Surprisingly, it wasn’t awkward at all. I was glad to see he could separate himself from his boss’s issues. That being said, Monday morning, I’m sure he was right back at the office saying, “You’ll never believe who I saw last night!”

When the concert was over, CK was raring to go and wanted to go to a bar. I was spent. I barely made it through the whole concert. I could tell he was disappointed, but he did a good job of hiding it as he took me home. I was happy to see the CK I knew and fell in love with again. When we got back to his place, I was still feeling a bit of the infectious energy from the crowd, and CK was still in concert mode. We stripped down to get ready for bed, but instead of falling asleep, we had the most epic sex we’d ever had to date. It was incredible! It was exactly what we needed. All our frustrations and cares were gone. It was a bit mind-blowing. It was passionate love-making at its best. It was all there, and I was truly happy again.

After our epic romp in the sheets, it was time for bed. We had plans for the following day, and we both had a very long and eventful weekend already. With that, we turned out the lights, and I fell asleep with CK nestled in my arms.

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This is Just the Beginning

The morning after my friend’s wedding, CK and I woke up in bliss. We started talking in hypotheticals about our own wedding. I’d never given any thought to my wedding since coming to terms with my homosexuality. I never had this great picture in my mind. It always just seemed like this big dream I’d never attain. But, now that I had CK, it was growing in possibility. I still didn’t imagine our picture-perfect wedding, but I did picture myself spending the rest of my life with him. I could see us old and gray together sitting on rockers on the front porch or going for our evening constitutional after a nice meal we shared at home on the sun deck.

Warning: The following may be too graphic for some. This isn’t exactly how I woke up. Before all this marriage talk, I awoke to warming, wet sensation in my groin. He continue this while I slowly woke and writhed with pleasure. I reached down and grabbed the back of his head while it bobbed up and down. Eventually, I grabbed hold of his hair and directed his head up to meet mine so I could kiss him. What a way to wake up. We continued fooling around in bed until we both finished.

I have had quite a few men in my life. Some of these men I’d dated for quite some time. CK was the first man to figure out how to make me finish every time. All that remained of my former embarrassing “condition” was barely an echo of a thought in the back of my brain. CK had often times mentioned to me how stupid my previous love interests were for letting me go. It was then I realized Broadway let me go when the sex started to deteriorate. Sex was a large part of our relationship, and when I found it difficult to finish, he lost interest in me. It made me question the relationship as a whole. Was the whole thing based on sex? Did he simply keep me around cause I was good in the sack? None of my previous relationships have instilled any bit of confidence in me, so I thought it better to not think about them anymore. I had something new and magical to concentrate my brain power on — There was no need to live in the past.

CK made me finish by manually stimulating my prostate. His magic touch is what kept our sex life alive and strong. By relieving this burden, I was able to concentrate more on other things, and I was able to relax. As a result, we had an incredibly healthy sex life. However, this comes with a price. No one likes to talk about it, but anal play can be awkward. Although I’d learned to relax, I was very self-conscious about things. I tell you this because I want to ease your fears about this. It gets messy. There are no two ways about it. There are ways to reduce this, and I highly recommend learning them. But, in the end, you both realize it’s no big deal and move on. I’m not saying this time was messy, but over the time I’d been dating CK, we both became comfortable with dealing with any situation that arose. There’s nothing a strategically placed small towel and a little soap and water can’t remedy.

When we finished in bed, we hopped in the shower and began to fool around more. We didn’t have sex because water is an awful lubricant! We washed each other from head to toe, making sure not to miss any of the nooks or crannies.

Afterwards, it was time for breakfast. I was being healthy, so I had yogurt. I’d decided to begin a new diet (and by diet I simply mean I was paying attention to what went into my face hole). I taught him how simple it was to make French toast, so he had that for breakfast. He was fascinated to learn how easy it was to make and enjoyed it even more knowing he made it.

I had made plans for us for the day to head to a friend’s for a barbecue. I made the mistake of assuming since we were in my neighborhood, I was responsible for entertaining us. We talked and decided to take the motorcycle out for a ride before we did anything. It was only when I mentioned we’d be dropping off food at my friend, D and K’s apartment that he learned about the barbecue. He wasn’t mad about it, but he didn’t appreciate not being consulted before plans were set. I apologized for being inconsiderate. I knew I was in the wrong and felt bad about it, but all was well.

We planned to film the motorcycle ride with CK’s iPhone similar to what we did on the bikes in Central Park, but it didn’t exactly work as planned. We rigged a contraption to record the ride, but the angle of the camera was toward the road. We’ll have to make a second attempt and post the video here when we get it down pat.

When we finished our ride, we went back to D and K’s apartment. There was a fun crew gathering, and I introduced CK to a few newbies he’d never met before. We spent the afternoon eating and having fun. The conversation was bustling between everyone, but the time came for us to head out. CK asked if we could go. He wanted me all to himself. I didn’t argue because I thought it was incredibly sweet of him. I was also happy to learn he liked all my friends and enjoyed seeing how well he fit in.

We went home and cuddled in my bed while watching a few more episodes of Game of Thrones. I made us fish for dinner, and when we finished, we made our way back into the city to spend the night.

While walking back to his apartment, he commented how he enjoyed taking the publicly more submissive role, cradling his hand in the crook of my arm. Being a guy who likes to protect and cuddle my man, I enjoyed being the more dominant role. We really fit well together, in every sense of a relationship. It’s as if we were meant for each other. When we finally got back to his place, we relaxed in bed with some Rachel Maddow. I was exhausted after a long weekend, so I didn’t last long before I dozed off cradling the man I love.

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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…

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Ladies and Gentleman, My Boyfriend

The morning after my “wild night,” I woke early. I was happy to realize I didn’t have a hangover, but I had a lot to do. I sat at my desk and went through circulars to make a grocery list, I went over my to-do list, I cleaned my bedroom, did two loads of laundry and sorted through my clothes to get rid of some of them. It was a very productive morning. The only thing I didn’t get done was to make it to the gym.

Around 11:00am, CK called. I didn’t want to call him because I was afraid of waking him. I knew he wasn’t a morning person. I was happy to hear his voice. He told me he needed to do laundry and wouldn’t come to Hoboken until about 2:00. I was fine with that. It allowed me to finish what I needed to get done for the morning.

I planned to head over to the Hoboken Arts and Music Festival around 2:00. That’s what I told P and my sister. As I was walking out the door, he called to apologize for running late. He was just walking out the door to hop on the PATH. Obviously he wasn’t going to arrive at 2:00. I told him I’d be at the festival, and I would make my way to him when he arrived.

I managed to find P, my sister and her friend without much effort. P had her dog, Baby, with her and needed to find her water. I told them I needed to make my way to the PATH to get CK, and they were welcome to join me. They all followed. We waited at the PATH for some time before he finally arrived. It was close to 3:45 before he finally arrived. He was running late as usual. I happily introduced him to the three of them, and we made our way back to the festival to find lunch.

Before he arrived, I had a worry in the back of my head. We were used to showing affection openly, but not in Hoboken. I still wasn’t out to everyone I knew around town, and I had my reservations about PDA. I was trying to get over it. There was no reason I shouldn’t feel comfortable being myself. But, I can’t lie. I was very nervous.

That being said, I greeted him with a hug, and we spent a large portion of the day holding hands and our arms around each other. This was a first for me. I did relax a bit and began to let my guard down.

We found the steak sandwiches I’ve gotten many years in the past and hopped in line. My old roommate (also my favorite roommate) was making his way toward us, so I told him where we were. I introduce him to CK, and he reminded me I’d met the girl he was with in the past.

As we ate, we walked uptown chatting. He mentioned wanting to do something special for my birthday that Friday. He asked if I’d be able to get out of work early, and I told him it shouldn’t be a problem. All I knew about this surprise was that it would cater to my adventurous side. I thought it was incredibly sweet of him to plan something special for me.

When we reached the north end of the festival, I was ready for dessert. I hadn’t passed anything along the way I really wanted, so I decided to hit up Ralph’s for some cream ice. I ordered the peanut butter cookie dough, and we shared it. It was utterly amazing.

P, my sister, her friend, CK and I were all heading to City Bistro to grab a drink on the rooftop bar since it was such a nice day. We found a seat and relaxed. I could tell one of the guys on the roof was making comments about CK and I, but I didn’t care. I continued resting my hand on his leg or putting my arm around him. I noticed two guy I thought might be gay and informed CK of the “Pickle game” I’d learned from Boston in Miami. We agreed they were gay.

The time came for us to head out. CK wanted to go for a ride on the motorcycle, and I needed to start dinner. We had to stop at ShopRite on the way home for supplies, and it was a bit of a walk home. CK wasn’t happy, but he did it — Not without complaining most of the way.

When we got home, we cuddled in bed for a few minutes before I told him I wanted him to help me with dinner. As I put the beef roast in the oven, I asked him to slice the potatoes for the scalloped potatoes on the mandolin. I warned him quite pointedly to be careful since the blade was so sharp, and I’d already cut myself pretty severely on it once, as did my mother. When he was cutting the last potato, he sliced his finger pretty badly.

I immediately ran to his rescue. He was bleeding pretty bad, but not enough for stitches. He sliced off a small piece of the tip of his thumb. He was now the third person to cut themselves on that mandolin (Him, my mother, and myself). He couldn’t believe how well I was handling the blood. I told him I was a lifeguard for seven years and had my own share of accidents involving a lot of blood. “Awww. Baby, you’re my lifeguard,” he said. I bandaged him up, told him to hold his arm above his head, gave him some painkillers and told him to sit on the couch. Maybe asking him to help was not a good idea. I thought it would be romantic, but it turned out tragic.

When dinner was ready, we ate in front of the TV. He raved about how good dinner was. We watched the shows I normally record on a Sunday night. It was really nice to have him fit so nicely into my routine. That was a sign our relationship had a solid foundation.

When we got tired, we made our way to my bedroom. He must have been really tired, and he kept dozing off. I wanted sex, but it was quite obvious that wasn’t going to happen. It’d been quite some time since we had sex, but I would have to settle for some cuddling instead.

He was out cold, so I brushed my teeth and came back to bed. I must have roused him, because he too got out of bed to brush his teeth. We turned out the light and fell asleep in each other’s arms.

It’s rare to find me happier than when I wake up next to him. It’s impossible not to have a smile from ear-to-ear. Warning: The following may be too graphic for some. As per usual, he began to give me a bl*wjob. It was one of his favorite morning activities. He told me he wanted me to finish for him. This is an immediate killer for me. I begin to concentrate on that alone. (I really need to see someone about this!) After a while, I told him it was time to shower. I scooped him up and carried him to the shower. He began bl*wing me outside the shower as well. I was too distracted in the bathroom, so I grabbed his hand and led him back to the bed. He felt amazing, and when he began teasing my boys with his tongue, I used my hand to get me over the edge.

“Baby. You taste so sweet today!” he told me. I was a bit shocked to hear this considering N told me I tasted awful. This made me like CK so much more in that moment. Seconds later, he exploded all over his own abdomen. It was incredibly hot to watch.

We went back to the shower and cleaned up. That morning, we joked about water sports. He threatened to pee on me in the shower. I told him if he did, I would certainly be returning the favor. When I saw his warm stream hitting my feet, I delivered on my promise. Both of us immediately got weirded out, and that ended immediately. “Yea. That’s definitely not going to be a thing!” I exclaimed. He nodded his head in sever agreement. Afterwards, I bandaged his finger once again and gave him a band-aid for the road.

We got ready and made our way to the PATH. I had to say goodbye to him in Hoboken to get my allergy shot, and he hopped on the PATH.

Monday, he called me as I was picking out a wedding card at CVS. He wanted to know if I was still in the city so we could meet up for a bit. I’d just gotten off the PATH five minutes prior. He was hopping elevator, so he told me he’d call me when he got up to his apartment, but I didn’t hear back from him.

I sent him a picture message of a t-shirt saying “I would cuddle you so hard.” He didn’t acknowledge the message. When I called later that evening, he seemed weird. He told me he was reading Hunger Games and sounded like I woke him up. The conversation was very short and awkward, so I just said goodnight and went to bed.

We made plans for Tuesday, but work got in the way for him. I proposed getting together Wednesday night at my place for Revenge again instead. I also left work early to pick up my new custom-made bed. I was so excited! I brought it home and assembled it. It was amazing. I sent him pictures, and he responded, “Can’t wait to break it in!” He also asked me if I would be interested in a show at the Upright Citizen’s Brigade. I told him that sounded great. Later Tuesday night, I texted him, but got no response until 12:30, just after I dozed off.

The question of fidelity did cross my mind for a hot second. I wondered if we needed to have the exclusivity conversation or was that covered under the can I be your boyfriend conversation? It wasn’t that I didn’t trust him, but my mind can run wild at times. I was just going to keep it in the back of my mind until I decided whether it was necessary to bring it up…

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Boyfriend Material

From early on, I learned of CK’s affinity for comic books. When I started seeing more and more trailers for the new Avengers movie, I knew it would be a big event for him. I was curious to see if he’d want to go with a group of his friends or would this be something special he’d want to share with me.

I’m pleased to say it was the latter. He asked me if I was interested in seeing it, so we made plans for Friday’s premier. I was also pleased to learn I would be meeting two of his close friends who would be joining us. We bought our tickets early in the morning, as they were already beginning to sell out.

After work, I went home and packed an overnight bag to take with me back into the city. I met CK at his apartment an hour before the movie. We cuddled and chatted a bit before making our way to the theater. As we got into the elevator, I noticed a sprig of hair dangling in front of his face. He really looked like Superman, and I loved it. This is where the Superman nickname came from. Just as I was noticing this, he ran his hands through his hair, messing up the sprig. That’s when he called me out for not commenting on his haircut. He had it cut after work that evening and was legitimately mad I didn’t comment on it, and he let me know it. I told him how I noticed the sprig of hair, but apparently that wasn’t enough. I needed to verbalize. I apologized profusely. I felt really bad. He eventually forgave me, but he was still a little putout.

I thought we had plenty of time, but he seemed worried about timing. He was trying to flag down a cab to cut across town, but none were available. When he spotted a pedi-cab, we hopped in and shot across town. He was like a little kid in a candy store. He was shouting at passersby and snapping pictures left and right. He took a lot of pictures of us kissing each other, in which I always look AWFUL!

We met his friends in line for the movie. CK introduced me, and I tried to make small talk. They weren’t the friendliest of characters, but they were far from cold. CK was still hyper.

CK and I split off to grab drinks for all of us at Dunkin Donuts. We grabbed donuts as well. While putting a straw in one of the large iced teas, I spilled it everywhere on the counter. The whole store came to a halt for about 5 minutes while the cleaned it up.

When we got back to the line, his mother called. While talking to her, he mentioned how the day of her arrival is my birthday. He also mentioned wanting for the three of us to try to do dinner.

Finally, we got into the theater. We got great seats, and I peeled off to get popcorn, candy and soda. But first I needed to relieve myself. I didn’t want to have to go in the middle of the show. One of CK’s friends came out to concessions with me. After using the restrooms, we stood next to each other not speaking more than ten words. It was a bit awkward.

I thoroughly enjoyed the movie. It was awesome, and I really enjoyed seeing CK so excited. The cuddling the accompanied the movie was also a nice addition.

As we were leaving the theater, CK ran toward the mini arcade. He wanted to play the two-person Terminator game. We put in our money and began shooting. It wasn’t long before one of his friends mentioned their desire to go. CK shouted at them encouraging them to play a game. He wasn’t having any of it. “I think we’re just gonna go,” he responded. CK convinced them to wait until the game was over. We left with them and said goodbye at the curb. They were tired and ready to go home. CK and I hadn’t eaten yet, so we were trying to figure out dinner.

As we walked to grab food, CK pulled my arm around him over his shoulder. People were commenting left and right. I was surprised. This wasn’t my first sign of gay PDA in NYC. I never experienced this before. Some of the comments were negative or simply mocking. Others were actually positive. Hell. We’re two good-looking guys. Why not?

We stopped at Charley’s Grilled Subs for cheesesteaks before heading back to his place to eat them in front of his iPad (aka, TV). When we got back to his place, we smoked a little, stuffed our faces, and watched the first episode of Smash. I’d seen it already, but I wanted to share it with him since I knew he’d like it. I fell asleep about three quarters through the show. Eventually, he too fell asleep. When he woke, he turned off the lights, and we pulled up the covers and dozed off.

Sadly, I couldn’t sleep in. My parents were coming into town to see War Horse and grab lunch. I needed to leave his apartment at 10:00am. I still needed to get them a parking pass in Hoboken. We woke to my alarm. I set it early to allow for ample cuddling.

While we were lying there, he said to me, “I know this is completely unnecessary and not something I need, but I’m going to ask you anyway. I want to know if I could be your boyfriend?”

I have no idea the look that must have been on my face. I was shocked. I did not see that coming, but I immediately said yes through an enormous grin. “Bet you didn’t see that coming!” he added. “No. No I did not,” I responded. I told him how utterly happy he makes me. I told him I thought it was a great idea!

I really don’t think he realizes how happy he makes me. I was beaming for the rest of the morning. He asked if he should order us breakfast, but I told him he didn’t need to do that. I told him I’d rather spend the time cuddling than eating since I didn’t have much time before I needed to leave. We began to fool around, which led to grinding. When he turned around and asked if I wanted to f*ck him, I told him I want nothing more, but I couldn’t. I needed to walk out the door in fifteen minutes. I could tell he was disappointed, but so was I. We cuddled some more before I had to say goodbye.

As I walked to the PATH, I had a smile from ear-to-ear. He made me so happy. I started texting friends to inform them of my new status.

I began to wonder a little if it bothered him my parents were coming into town and I wasn’t introducing them to him since he was so keen to introduce me to his mother. His mother lived much further away, so it somewhat made sense, even if it was early in the relationship. My parents would be back by at least June. I could introduce him then. I just hoped he wasn’t hurt I never mentioned it.

Either way, I wasn’t going to worry about that. I was too happy to car. For the first time in my life, I had a boyfriend!

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Never-Ending Date

I’d begun an amazing date with a spectacular man, and I couldn’t wait for what was to come next. Although I had been to Frankies 570 multiple times before with multiple dates, this time was special. I had an amazing guy to share a meal with. Ironically, my meal from days prior was so good, I ordered the same the again.

Conversation over dinner we great. It flowed like water downhill. We were both very flirtatious and chatty. On many of my other dates, there were long awkward pauses, but not on this one. Everything was just so easy. When I excuse myself to go to the bathroom, he leaned in requesting a kiss first. It was incredibly sweet and adorable. I really liked this guy. He was everything I was looking for.

I was just taking extra care to make sure I didn’t get ahead of myself. I had a history of falling for guys who would hurt me or not be interested in pursuing anything further. While in the restroom, I looked in the mirror to keep myself centered. All I could do was smile at my reflection like a giddy schoolgirl.

When I returned to the table, the conversation picked back up where we left off. My hand was on his leg under the table. His body language was very positive.

Our meals came, and we shared them with each other. Both of us were very happy with our selections. When the meal ended, we agreed to order a dessert to share. We got the crème-brulee. I dug my spoon into it and fed him a spoonful. It felt incredibly romantic. He smiled as his mouth closed around the spoon. We finished dessert and began to chat about what to do next. He was dancing around what I can only assume were his true motives. He said, “We can go have more drinks.” I interjected, “I don’t want to drink anymore.” “We can drop our bags at my place and go out. We could grab Pinkberry…” he added. I cut him off at the pass saying, “You can stop dancing around it. We can go back to your place.” He immediately smiled and agreed that was the best idea.

I wasn’t thinking we were going back to his place for sex. I knew there would be making out and a lot of heavy petting, but I wasn’t planning to give it up that easily. We hopped in a cab back to his apartment. He asked if I wanted to go to the roof, and I told him I would default to him. We were on his home turf. He could run the show. I picked the bar and restaurant. It was his turn to drive. Before we got to his place, he warned me of the condition of it. He informed me he lived like a frat boy.

When we got to his place, we stopped in his apartment on our way to the roof. I didn’t think he was as bad as he let on. We began making out on the bed. This, of course, led to many other things. Slowly but surely, clothes started landing on the floor in scattered piles. Eventually, we fond ourselves naked and engaging in a myriad of sexual acts, but penetration would never occur.

He was a very passionate man. I have found it nearly impossible to find a man whose intellect, wit and sense of adventure outside the bedroom matched their passion in the bedroom. He was a diamond in the rough. I wasn’t going to let this one go without a fight.

I noticed he was very into music. It was like he needed a soundtrack. I liked it. Every minute I was learning something new about him, and it was all making me like him even more.

We never made it to the roof. We ended up passing out on top of each other’s naked body. In the middle of the night, we both woke up. It was around 2:00. He offered for me to stay. I was under the impression that was already happening. I assumed I would just stay the night. We cuddled some more, and he turned out the lights.

When we woke in the morning, things weren’t awkward at all. I felt very comfortable with him. We talked about how we didn’t have sex and how that made us both happy. We didn’t need to rush things. I mean, I was spending the night on a first date, but I was happy true sex didn’t occur. I was also thrilled he was the type of guy who would just bring that up and not keep it inside for fear of saying the wrong thing. He spoke his mind. I needed to get back to that. Being with him might help me get back to that.

He was amazing. There was no question about it. We were both starving and decided to get dressed to hunt for some breakfast. We stopped by a few places before finally settling on Jimmy’s American Grill and Bar. We grabbed a table outside and picked up the conversation where we left off the previous night.

I let my freak flag fly. I felt so free with him. I told him all about me and my idiosyncrasies. I explained my Christmas Bash and all the work I put into it. He referred to me as Martha Stewart, and I expressed my hatred for that referral. I didn’t like that my cooking and entertaining had a feminine connotation. I told him I was more the Nate Berkus type. He laughed and agreed it was a better reference. I told him about my crazy coworkers and how we would make an amazing reality show. I told him about growing up on a farm. Everything I could think of, I brought out. He loved it all! I learned about where he grew up and his career in advertising. Every word made me like him more and more. He also told me about his friends. They texted him while we were eating to ask him to come to brunch 2.0.

Somehow, we got on the topic of The Hunger Games. I was reading the books, and he had already seen the movie. I told him I was looking forward to seeing the movie. He told me he would go see it again and asked if we could go see it Sunday. You could have knocked me over with a feather. He was already planning date number two before date number one concluded. I was thrilled and immediately accepted.

He walked me to the PATH to say goodbye before heading downtown to meet his friends at Elmo. We kissed each other goodbye and gave a long lasting hug. There was a homeless man panhandling next to us who said, “Get a room,” through a smile. He began laughing, and I started to crack up since I was the one facing him. I said to my amazing date, “That made my day.” Immediately, he replied, “You made my day.” I was in heaven. I said goodbye and went down the stairs to the train.

Later, I learned from checking his Twitter that when he checked in at dinner on Foursquare, he wrote, “Easy conversation + tasty food + hot boy = great date on a Fri night (@ Frankies 570 w/ 2 others)” and the next day at brunch, “When last night’s date becomes this afternoon’s brunch date (@ Jimmy’s American Grill & Bar). He really did like me. I was just finding it hard to take. It was like a dream. I couldn’t really believe it. I didn’t want to get too excited because I didn’t want to get hurt. But, honestly, who gives a f*ck. I was happy, and that was all I cared about.

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Another Boring Date

Tuesday night, I was happy to be home. My date with S.D. wasn’t bad, but it helped me realize he wasn’t the guy for me. We had too many differences of opinion.

I noticed on my calendar Broadway‘s birthday had arrived. I made sure to call him to wish him a happy birthday, but he didn’t answer. If I recalled correctly, he was in California for a vacation. I left him a message and told him to call me when he had a free second. I didn’t hear back from him for over a week. I was a little disappointed, however, we still maintain a friendship. His friendship is important to me.

On my walk to work Wednesday morning, I checked my Grindr messages. I began to chat with one guy, but that’s another story for another day…

I had a date planned that Wednesday with a guy I chatted with on OKCupid, but he ended up bailing on me at the last-minute. This time, I had no one waiting in the wings. I debated just lying low and going home after work, but another part of me didn’t want to waste a free night. I thought I’d reach out to my current roster to see if any of the guys were free to meet. I figured I might as well get a first date out of the way while I had the time. I was really looking at dating like a job. This was bad policy, but with someone like me who has a busy schedule, you gotta do what you gotta do. I sent out feelers to the guys to see who was available to grab a drink after work.

Ironically, two of the guys responded. One was in Hell’s Kitchen and the other lived in Jersey City. I wondered if I could schedule them both in the same night. Hell’s Kitchen would work out because I could just take the bus home, and Jersey City could work if he came to Hoboken to grab a coffee or a drink when I got home later. I wasn’t all that psyched about the guy from Hell’s Kitchen, so I assumed it would be a short date and work out.

The first guy picked a nice restaurant, Pier 9, at the north end of Hell’s Kitchen to grab a drink and maybe an appetizer. It just so happened to be right across the street from his apartment. We met just inside the restaurant. I wasn’t excited by what I saw. He wasn’t unattractive, but he wasn’t attractive either. That being said, I wasn’t writing him off based on looks.

He was a regular here. He knew a lot of the wait staff, and they took good care of him. We grabbed a seat and began to chat.

The conversation was pretty relaxed. We both decided to order wine, and since it was happy hour, we split a bottle at half price. We also noticed a great edamame appetizer on the table next to us and ordered that to split while we got to know each other. It was a very nice place, and the wait staff was super sweet to us. They could tell we were on a date and treated us as such.

We talked about our jobs, our families, life in the city, etc. It was nice conversation. Nothing was forced or awkward, but there was no spark either. He seemed like a really nice guy, and we agreed on a lot of things. I could see us getting along really well, but more in a friendship capacity than a dating one. I could see him being a good date for Sunday morning brunch to talk about the weekend and talk about guys.

We were there for a decent chunk of time. The date lasted about an hour all said and done. We finished the bottle and the appetizer and decided it was time to head out. I could tell he didn’t find a strong connection there either. I had to initiate the goodbye hug, and there certainly was no feeling behind it. This would make things easier. We left with the same expectations of not hearing from the other much after we parted ways.

As I walked to the bus, I started texting the guy from Jersey City. We’d talked more than a few times before. We’d become Facebook friends, and I was supposed to see him on Hoboken St. Patty’s when he was attending the gay party across the street from my apartment, but he never made it. I asked him to an unconventional date. I lined it up for him to come to my place and just relax with a glass of wine. He agreed that sounded like a great idea, so he came over shortly after I came home. We were finally making time to meet up in person…

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Check That Off the List

Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.

This post is embarrassing. It is now especially embarrassing because a few readers have commented about my promiscuous ways, but nonetheless, I will report the incident honestly and to my best ability. I, in no way shape or form, condone the following behavior. An early warning as well – this post will be graphic.

For some time, I’d been speaking to a few guys on Grindr who happened to be tops. When we both learned we were the same position, discussion turned to other options, such as bringing in a third. We were both really attracted to each other, but neither was willing to bottom for the other.

Many men dream about the threesome. Straight men fantasize about it constantly, and I assume it’s a big gay male fantasy as well. The only difference is gay men probably act on it and achieve it far more often. It certainly isn’t, however, easy to pull off. You have to organize three different mens’ schedules and also take into consideration their taste in other men. We all know how finicky gay men can be.

I woke up Friday with no agenda and morning wood. I wanted to take care of it, but I also wanted to act on my recent fantasy of a threesome. I started with one of the most promising guys who I’d discussed this with before. He wasn’t getting back to me. I began going through more than a few permutations trying to find 2 guys willing to participate who weren’t occupied with work.

Finally, I found one, and we both began to hunt for that elusive third. There were many roadblocks, and lots of waiting to hear back when questions were posed. I thought I had it all worked out, when one of the guys went dark on me. I was very disappointed because I thought I found the perfect combination. One top (me), one bottom, and one vers. When the bottom got a flat tire, it all went to $hit. All this juggling really made me realize why this never happened before.

After much discussion about who could host and who wouldn’t host, I managed to get my original group together, but not without issue. I had to ride my motorcycle into New York City to pick the bottom up. He wasn’t comfortable coming out to Hoboken alone, and the other guy wasn’t willing to host strangers. Strange to think he had no problem hopping into bed with strangers, just as long as it wasn’t his own. I rode in and picked him up. It was slightly awkward, but it all fell right into place. He hopped on the back of the bike, and we rode off to my place.

Warning: The following may be too graphic for some. We arrived before the other guy. I didn’t know the rules, but I was looking to wait for the vers guy to arrive before we got started. The bottom wasn’t so patient. He wasn’t the best looking man in the world, but he had a great body. He started kissing all over me until he undid my pants and started orally pleasuring me. He was quite good. He undid his pants as well and revealed a generous gift. He asked me if we could go to the bedroom until the other guy arrived. I encouraged him to wait since he was only a few blocks away.

When he arrived, the bottom walked to my bedroom and began to undress. I brought the vers guy into my room, and he and I began to undress. I wasn’t as thrilled with him. He looked much better in his pictures, but there certainly wasn’t anything wrong with him. You can’t win ‘em all. I laid on the bed in my boxer briefs while the other two joined me and began rubbing me all over and kissing me. I felt like a king. Everyone was there serving me, and it felt great!

Then the underwear was removed on all parties. There was lots of rubbing, kissing, sucking, etc. After some time, I broke out the condoms and lube. I was horny and ready to get started with the real fun. After using his poppers, the bottom was ready and eager, so I penetrated him while he orally pleasured the vers. Then the vers came to my side of the bed. We’d already discussed I wasn’t bottoming, but he thought I could be persuaded. I told him sorry, but no. I backed off and let him have a turn with the bottom.

This guy was incredibly awkward. He looked like he was having a seizure. His sex was spastic and crazy. On top of that, he was very particular and insisted I use the condoms and lube he brought. While he was inside the bottom, I climbed on top and penetrated the vers. This was not the easiest sex position by any means, and it did not last long. The logistics of three people getting the same rhythm are nearly impossible. It’s obvious in porn when this happens, they are doing it for the camera and certainly not for pleasure.

We swapped positions a few times and had already gone through a substantial amount of condoms. If one thing was certain, I was going to be wrapped up at all times! Finally, I suggested we move things to my shower.

We went through a few permutations of positions in the shower before I told them I simply wanted to watch them while I took care of myself. The bottom protested. I could tell he was very annoyed by the vers and wanted me more. When we ran out of warm water, we all toweled off. The bottom needed to excuse himself. He was feeling light-headed. He made his way out to the living room in his towel.

I was left with the spaz in my room, and I wasn’t thrilled. We tried a go at it for a short bit, but I was much more interested in the guy sitting in the living room. We stopped and moved things out to the living room after closing all the curtains. The bottom was feeling better, so he was eager for me again. He hopped on the chair and asked me to go again with him.

There was something that really turned me on watching the other two guys have sex. I pulled out and encouraged the vers to join in again. I wanted to sit on the couch and finish while I watched them. The bottom wasn’t happy about this because the vers was bad at sex. All three of us were on the couch when I finally finished on my chest. The vers reached climax as well, but the bottom seemed content with stopping before he finished.

The vers guy almost immediately began to get dressed, noting he had to get back home to finish work. The bottom was going to head back in with him so he wouldn’t get lost, but the vers wasn’t willing to wait for him to get dressed. The bottom asked me to ride him back onto the city, but I told him I would give him a ride as far as the PATH. From there on, he was on his own.

We chatted a bit about how spastic the other guy was. Neither of us were thrilled with him, but it is what it is. The bottom got dressed and hopped on the back of my motorcycle. When we got to the PATH, I gave him directions for getting back home.

I sped off home. I was in need of a serious shower. Since the morning’s activities began, I felt incredibly dirty.

If you’re considering a threesome, I strongly encourage you to think it out first. Don’t just jump into it to satisfy some great fantasy you’ve seen many times in porn. If you have the constitution for it, then by all means, do what makes you happy. But, if you’re thinking twice, I strongly suggest you leave the fantasy to your mouse clicking.

There was nothing sexy about what happened. It did not live up to the fantasy I had originally dreamed of. It was awkward and at times laborious. I needed to wash away the shame and guilt I felt, but it was no use. Those would stick around for at least the remainder of the day.

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Late Night Quickie

Sunday night in LA, I took quite a blow to my heart. I tried to prepare myself for the inevitable goodbye, but I didn’t get to say goodbye. I’d driven all over LA trying to connect with The Navigator, but he wasn’t responding.

I faced facts and drove to the airport. I had no idea what else to do with my time, so I just drove to the car rental lot and returned my car. I figured I could at least use some time at the airport to blog a bit. I sat int he airport diner and ate my dinner alone.

My flight home was awful. First off, it was a redeye. I was set to land at 6:00am Monday morning. I had to go to work later that day so I tried my best to sleep on the plane. It was also awful because I was crammed in a widow seat towards the back of the plane. My airline status with United got me nowhere. I barely fit in my seat, and I wasn’t able to stretch out and walk around because the two men next to me were sleeping the entire flight.

I managed to sleep for two hours, but woke up after that. I had no feeling in my ring and pinky finger of my left had. Apparently I slept on it funny. When a fair amount of time passed, and I never regained feeling, I became worried. Maybe I had a blood clot or maybe I’d done some nerve damage. I tried to think about other things and distract myself, but I really started to get worried. I took out my laptop and did some more blogging, but even that was a challenge with two numb fingers. I was really starting to worry, but the feeling didn’t return the rest of the flight. (Four weeks and a doctor appointment later, and I finally regained feeling — I had a nerve impingement — Cubital Tunnel Syndrome).

I was exhausted all day at work Monday. I’d only gotten a few hours sleep on the plane and about one hour in my own bed before work. When I got home after work, I was still horny from my rambunctious trip. I was on Grindr, and a cute guy from the city wanted to come over for some fun. I didn’t turn him down since he was hot and said he’d wear his jockstrap.

When he arrived, I realized he was a redhead. He also had a slight Hispanic accent. He was also quite a presence clocking in at 6’4″. He was not born in America, but had been here a majority of his life. He was decent on the eyes, but nothing you’d run to your friends about. When he arrived we went straight to my room. He slowly got undressed and comfortable until we were both laying on the bed, me in my boxer briefs and him in a jockstrap.

Warning: The following may be too graphic for some. I found the jockstrap very sexy. I’ve always been attracted to the athlete types and find locker rooms to be one of the sexiest places. They just turn me on. Always have.The jockstrap really gave him the leg up in my book. He was looking for a hot top, and I agreed to fill the position, literally. I broke out the condoms and lube, and we have a good time. Sometimes it was a little weird and awkward, but sex is never perfect! He really seemed to be enjoying himself. I did as well, but I could already tell this guy was going to linger. He was a gentle spirit. This would be no wham bam thank you man. I was going to have to sit through some pillow talk.

He started talking about his grandmother and how she is sick. He was flying home the following day to see her before she passed away. It wasn’t looking good. I started to feel bad for him, but then my emotions became distracted when he mentioned things like sleeping with her in her hospital bed. He looked like he was ready to cry, but all I could think about was this strange layout in a hospital room. I understood he was close to her, as she was responsible for raising him, but some of the things he was saying with his accent seemed very strange to me. There was obviously a cultural divide.

After we chatted some more, and he asked if he could use my shower. Now he was really pushing it! I obliged the request, but after that, he was gone.

He showered and toweled off. He began to get ready to go home. He talked about getting together again when he got back. He mentioned how heartless a lot of the other guys he’d hung out with were, and how sweet I was. He said how much he liked me. He wanted this to be an ongoing thing of friends with benefits. He told me his real name and that the name he gave me, Keith, was completely made up. Someone was a little paranoid. I felt like I found a stray puppy who wanted to follow me home. There would never be a next time, but I told him to hit me up when he got back from visiting his grandmother. After about three weeks, he did of course text, and I of course did not respond.

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