Posts Tagged strangers

The Calm Before the Storm

CK and I had a rocky night, but before we laid our heads on the pillows, we reconciled our differences. There’s no fight we couldn’t get over. We were truly in love.

The next morning, I woke up early to work out with CK in his rooftop gym. It was our first time up there, and we were finally going to workout together, or at least we both thought so. It turned out, we had different ideas of working out. While CK was on his cleanse, I too was trying to lose weight. That was only going to happen for me if I did cardio workouts. Lifting wasn’t going to help me shed any pounds, and that was the priority over bulking up. He wasn’t willing to join me for cardio, and I wasn’t willing to lift, so we worked out at the same time on opposite ends of the gym. When he finished, I was nearly done my three-mile run, sweating profusely from head to toe. I wanted to take off my shirt and use it as a sweat rag, but I wasn’t sure if that was P.C. in his gym, and there were others working out as well. When I finished, we rode the elevator back down to his place so we could shower and get ready for work.

As per usual, we showered together. This had become a regular thing for us. We rarely showered alone anymore. We weren’t always making out or having sex in there: It just seemed a better use of both our time to shower together. We were beginning to work out a system between us. Our routine was falling into place.

The one thing I slightly resented when sleeping over at his apartment was the lack of breakfast. It was getting expensive for me to continuously purchase breakfast every time I slept there. I made sure to provide him with the necessary items for breakfast, but we hadn’t seemed to get to that stage at CK’s apartment. I wasn’t going to make a stink about that. One thing at a time. I was happy he finally had all his boxes unpacked and a bed to be honest. Breakfast could be dealt with down the road.

We got ready and were out the door. We’d also managed to figure out we could commute together to work. Originally, he was walking to a different subway than I was, but after further investigation, I learned we could both catch the necessary subways from the same station, and it would be the same distance for CK. Every morning we walked together and said goodbye with a kiss on the platform. It was a simple routine, but I was already thoroughly enjoying our morning walk to work together.

That night, CK had to work late. I went home and went to free outdoor yoga on the pier in Hoboken with my roommate instead of CK. We were spending the night apart. He had to be at work early the following morning for a pitch. When I got home from yoga, I made dinner, watched TV and fell asleep in my bed alone after chatting with CK about his day.

I woke up early the next morning feeling lost. The man I loved wasn’t there. It was shocking how much of a difference it made having him in my bed. I didn’t sleep nearly as well as I did when he was present. It was like I was an infant all over again missing my mother’s heartbeat. I needed to feel him close to me to get a good night’s sleep. I forced myself to get out of bed and motivated myself for a nice morning run along the Hudson. I stopped to take pictures for Instagram of the city where I knew my boyfriend was still soundly sleeping.

I ran back home, finished getting ready and stopped by the allergist for my shot before heading to work. I was really committing to getting in shape and losing weight, so that afternoon, I took lunch at the gym. I wanted a six-pack again, and I wanted shoulders, arms and pecs I could be proud of again. When I finished, I was in a spectacular mood. I shot CK a text to remind him how much I love him. I was also horny from the endorphins running through my veins. I started to sext him, telling him all the things I wished I could do to him in the gym shower.

Warning: The following may be too graphic for some. That’s always been a fantasy of mine, however, I never had any desire to do it with complete strangers. In an ideal world, CK and I would go to the same gym. We’d walk in together, but not acknowledge each other while we were in the gym working out. When he was finished, he would head into to the lockers to shower. He’d strip down in front of me, not acknowledging my existence before strutting to the shower of his choice. I would follow just behind and slip into his shower stall and close the curtain behind me. We’d have sex under the hot water without causing too much commotion to attract attention from others. After finishing inside him, I would rinse off and leave the shower like nothing happened. He would finished washing up and recovering from our tryst while I got dressed and headed home like nothing happened to start making dinner. He would follow a few minutes behind, and the first time we would acknowledge each other would be at the door where I’d welcome him home from a hard day’s work at the office with a big kiss. We’d eat our dinner with big smiles knowing we have an epic sex-life. Some day…

So in shorter terms, I described this situation to him over text. When I first began, he thought I meant to text someone else. He must have thought I was cheating on him with someone at the gym. I assured him the texts were for him and reminded him how the conversation begane explaining that this was my fantasy. I also pointed out the irony of the situation and detailed how he was the one who sexted the wrong person, not me (just like the first day we started chatting and he wanted me to come over for sex).

That night, I had plans to see Porgy and Bess with my coworker, so I didn’t see him again. I think he felt a bit left out, but I’d been coworkers with this girl for over five years, and the two of us had never hung out outside work together. I also had to head to our Chelsea office to work early in the morning. I took the opportunity of being off the radar a bit to hit the gym again that afternoon, this time for a run on the treadmill. I began thinking about CK and I in the gym once again, but it would remain a fantasy.

When I finished work, I went to my volleyball game, came home to shower and made my way into the city to spend the night in CK’s bed. We’d spent a decent amount of time apart considering we’d been spending every waking minute together outside our workdays. I was thrilled to see him and even more ecstatic I was sleeping with him that night. After a late-night romp, we dozed off in each other’s arms. When we woke in the morning, we hit the gym once again. Alas, we worked out on opposites sides of the gym once again.

When we finished, we continued our routine of getting ready for work and were out the door. That night, after work, I ran home and grabbed my things for the weekend. We had a big weekend coming up, and I had to pack for many different options. It was EXTREMELY frustrating because I wasn’t sure what we’d be doing, I wasn’t going to be home again until Sunday at the earliest, and it was Pride Weekend. I asked CK for help on what to pack, and he was of no use. The fight was quickly escalating over the phone, and my frustration level was at its peak. I wasn’t used to going to gay events and circuit parties, and I was feeling a lot of pressure. This was a burden I’d been carrying around for weeks, and the moment of truth was arriving. This was going to be my first full Pride Weekend, and I had no idea what I was about to get myself into. I was scared sh*tless!…

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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.

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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.

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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.

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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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Asian Sensation

Today is another Fast Forward Friday!!!  

Hope you are enjoying these. It will help bring the blog a little closer to real-time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!

Back to your special edition of One Gay At A Time…

After a relaxing afternoon of fine food and poolside tanning, I’d already wet my appetite with some Armenian. It was a speedy delivery, and I enjoyed it. But, it left me still desiring more. If I was going to do this, I was going to do this. I was going to fully take advantage of my hotel room.

I hopped back on Grindr and decided to have some Asian delivery as well. We chatted a bit, and he sent me some pictures. I don’t typically go for Asians, but I liked his eagerness and spunk. He was hungry, and I still had an appetite.

After exchanging pictures and chatting a bit, I told him to come by. I showered to get the smell of sun screen and Armenian off me while I waited for him to arrive. I was already feeling like a bit of a hustler, but I also wanted to give myself a high-five in the same turn.

When he arrived, I answered the door and he came in. We chatted a bit on the bed before finally making a move and making out with him a bit. Slowly but surely, I got him naked. He was eager to please, and I really appreciated that. I think he cared more about how much I was enjoying it than he did himself.

Warning: The following may be too graphic for some. We tried numerous positions with each other. We never did anything really complicated, but I could tell this guy liked to have fun — And we were. However, I think he was enjoying it far more than I because he finished in no time flat. He really loved to bottom, and it showed.

I didn’t finish, but I couldn’t keep going after he finished. I’d have him in pain in a few minutes if I kept going. We laid there next to each other chatting a bit more about what we did for a living and where we lived. I was still really horny and I wanted to keep going. I knew my body was capable of rallying the troops again after at least two hours since the Armenian. I wanted to keep going.

I gave him some time to recover while we chatted. When I thought enough time had passed by, I asked if he wanted to go again. I asked if he was able to rally the troops again. He said, “Sure. If you wanna go again. Pretty sure I can do it.” I proposed we move things over by the window. I was feeling quite adventurous now. I was on the 19th floor. I knew it wasn’t likely we’d be spotted, but the chance of it happening made the sex that much more exciting. He agreed with a grin from ear-to-ear.

We moved to the window with both his palms pressed against the glass and his legs spread. We had a really hot time with my arms wrapped around him. It was one of the most fun positions/situations I’d been in. With a fresh condom, we went at it again. This time, I wanted to see him finish. I used my hands to pleasure him while he moaned loudly. I wondered if my “neighbors” would hear us. He finished on the carpet below as he let out a loud moan, but sadly I wasn’t quite there yet. I continued to attempt to see if I could finish, but something just wasn’t quite there. I couldn’t concentrate, and I knew this was a lost cause.

I’d already been talking to a guy who asked if he could come by late night. I decided to stop trying and save up for the next guy’s arrival. He turned around and expressed his gratitude and told me how hot that was. He cleaned up and got dressed, and I said goodbye to yet another guy whose name I didn’t even remember.

I was such a whore! I’d just been with two strangers in the same evening, but I told myself I was on vacation. I justified it in my mind by telling myself when I returned to New York, I was going to be a good boy. I gave myself a weekend pass and decided to get it all out of my system. The maid at the Hilton was certainly going to have a large pile of towels to clean up in the morning…

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Deep Pockets

Since deciding to end things with Smiles, I’d already been on one date and had one hookup. I certainly hit the ground running. I felt slightly guilty all this was going on before we even had the chance to formally end things, but then again, things never really formally began between us.

I wasn’t wasting any time either. I had been talking to a really nice guy on adam4adam.com and set up a date to grab drinks with him after work Friday evening. It was a bit awkward because this was truly a blind date.

He had two pictures on a4a, but neither was clear and one didn’t include a face. When I asked him to send me a better face picture, he told me he didn’t like taking pictures of himself. Of course a red flag raised in my mind, but I had nothing to lose either. If I arrived and the guy was unacceptable, I was right next to the Port Authority bus terminal. I would be home in no time with little of my time wasted.

We agreed to grab drinks at Arriba Arriba in Hell’s Kitchen. It was conveniently located between his apartment and my office, and like I said, it wasn’t far from my transportation hub to go home.

As I left my office and began walking north, I was quite nervous. I’d never been on a true blind date before. I’d at least seen pictures of their faces, but this time I had no idea what he looked like. I joked with him, “Not gonna lie. Not sure what you look like… Haha.” It didn’t take him to respond: “Sorry mate. Don’t like taking pictures of myself. We will find each other… haha. You can ask me to leave once you see me and how ugly I am. Lol.” I didn’t care all that much at this point for the picture. I was already going in blind. I replied, “No apologies needed. Just tellin’ ya you’re gonna have to find me…”

I waited for him on the street corner. I put that time in a good location to good use. I surfed Grindr in HK for any new prospects. I know some may say that is classless considering I was waiting for a date, but I’m not in HK all that often anymore, and there is more talent in that neighborhood than where I work. He finally arrived and approached me. I asked how his trek to HK was, and we went inside to find a table.

When we learned we could only stand at  the bar since we weren’t ordering food, we decided to go elsewhere. I was at a bit of a loss because I hadn’t been in the neighborhood for some time. I didn’t know of a good place for us to go for a drink. Luckily, this guy was good on his feet. He suggested Eatery, and we were off.

We grabbed a seat at the bar and ordered a few rounds of drinks. We chatted for a long time about a myriad of things. The whole time, he kept his ball-cap on. Beyond the fact that he should know it’s bad manners, especially since he was an older gentleman, I was also worried there may be no hair under there. I’m not shallow, and looks are not everything to me. But, if he was balding without shaving his head, I wasn’t sure I could deal with that. (Smiles shaved his head and I was obviously okay with that).

We talked about our upbringings. He lived a bicoastal lifestyle, living in California and South Carolina. He also was shipped off to boarding school in Switzerland, where his grandparents lived. I grew up on a farm and went to public school. We had quite the education/socio-economic divide before. This is one thing I‘m not sure I am capable of getting past. I’m sure if it was the right guy, I could handle him coming from wealth, but it’s something that makes me quite uneasy. He came from money, and a lot of it.

I also learned he leads a very lavish lifestyle. He told me about his plans to purchase a house in Barcelona. He’d recently traveled there to scope out some places. He also told me about the $200,000.00 loan he gave a friend and was never paid back because the friend died and left his only possession, his apartment, to someone else. He told me about his lavish trips to the Caribbean islands recently. The list goes on.

Ironically enough, he wasn’t talking about all these because he was trying to impress me (Or at least it didn’t come off that way, which is fine). It simply came up in conversation or I coaxed them out with questions. I just felt uncomfortable with our socio-economic differences. I don’t really aspire to the position of kept man. I want someone who will share the financial burdens with me equally. I know a lot of people would love to find someone rich to marry, but money means very little to me when it comes to love. I think like I would constantly feel like less of a man if I had everything provided for me constantly, and I contributed far less to the relationship. Maybe this is something I will learn to get over in time, but for now, it makes me uneasy.

I learned how he continued to build his wealth and his professional relationship with a family in Canada. He told me about all the businesses he was involved in, and I started to worry he was another Smiles — Too much on his plate to commit to a real relationship. I also learned he wasn’t out to many people in his life, even after he’d been in a nine-year relationship with a man who left his wife for him. It ended when the man cheated on him while he was away on business. I wasn’t sure how I felt about him still being in the closet. He’d experienced too much and was far too old to still be in denial of his true self. I wasn’t sure I wanted a “project” at that age.

Drinks quickly turned into dinner. We stayed at the bar and made friends with the waitress. She was super sweet and very interested in chatting with us. Over our meal, we conversed more, and I learned we share a lot of the same morals and interests. We had similar outlooks in life.

He also became much more physical as the night progressed. He constantly had his hand on my leg rubbing my thighs and caressing the back of my knee. I started to do the same. Periodically, he would stand and give me a big ol’ bear hug. It was sweet. I liked knowing he was a passionate physical man. I needed that after Smiles constant distance.

Six hours later, we were ready to leave the bar. He decided to walk me to the bus. I thought when we exited the restaurant we’d exchange a kiss and go our separate ways. He was a true gentleman and walked me to the Port Authority. Not only that, but he walked me to my gate to wait for my bus and stood there waiting with me. It was midnight, and he was being a total sweetheart. He stood anxiously next to me as if he didn’t know what to do or how to close the date. He wasn’t really out, so I had a feeling a goodnight kiss in front of a large group of strangers was out of the question. When my bus arrived, he said goodbye and we agreed to be in touch.

As I rode home from the date, I wasn’t entirely sure what I thought of him. He became more attractive as the night went on, but I wasn’t sure if that was his personality or the alcohol stepping in for average looks.

I had a lot to think about. It was clear to me he was interested in me. The next day, he texted to see if I was interested in catching a movie that evening. I told him I had plans to hang with friends locally, but if they fell through, I’d let him know. When I decided to keep my plans, I texted him to let him know. He wasn’t all that concerned considering he had hopped on a flight to Boston to hang out with friends and go to a party. Yup, hopped on a flight that day. He obviously didn’t have a planned flight considering he asked me to go to the movies — Unless he was planning to fly me to Boston to do so…

That night, while out with my friends, I called Boston. He told me some of his new exciting war stories, and I told him of my trepidations about Deep Pockets. He told me I was nuts to write him off based on financial differences, so I decided to see where things went over the next week or so.

We texted a few times more, but interest wasn’t strong on either end as the text messages slowly came to an end. I was on to the next prospect…

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Short Goodbyes

Still thrilled about a spectacular weekend with Smiles, I began a new week.

Monday passed by without me seeing Smiles again. I did speak to him however. We spoke while I walked home from work. He still had a migraine, and I tried to console him. I wished there was something I could do for him, but I was powerless.

He had a work event that evening, so he soldiered on. His migraine was lessened, but he still wasn’t 100%. I knew it was going to be a long night for him.

He called when the event was over to say hi and check in on me. I always relish his phone calls just to say hi and ask me about my day.

I explained to him I was watching the first Twilight movie. It happened to be on TV that night, so I made it a point to watch in an attempt to catch up to the current day release of Twilight: Breaking Dawn pt. 1. I was also able to find the second and third installments in the series on the guide over the next few days. Smiles seemed excited to see the movie, so I was putting in the effort to get onboard. I have to say, they’re certainly not amazing cinema, they’re not unbearable either.

I asked him to wait to see the movie together in the theater. He agreed. After talking about the series, he realized he’d never see the third installment, Twilight: Eclipse. I told him I would keep it on my DVR, and we could watch it together before hitting up the newest in the theater.

We were also coming up on Thanksgiving. I struggled with the thought of inviting him to come home with me. He is from and his family is still in Florida. I knew he wasn’t planning to go home, but I wasn’t sure if he’d have other plans. The thought of inviting him came from numerous places. I felt we were comfortable with each other, and I knew he would stand well with my family. He was very good at getting along with strangers, and I knew he could win them over, especially since this would be the first time they’d learn about my homosexuality. I knew it would have been a little early in our relationship to ask him to come home with me, and this is the main reason why I didn’t. I didn’t want him to think I was a little psycho.

In the meantime, I learned he finally did make plans for Thanksgiving. He was going to a few friends’ homes out on Long Island in the Hamptons and on Fire Island. I was happy he found some special people to spend the holiday with, but was a little disappointed I wouldn’t be spending it with him.

Before I went home, and he split for Long Island, I wanted to see him again. I suggested we grab coffee or something quick because I knew he would be quite busy with work leading up to our departures on Wednesday. He told me we’d have to play it by ear, but he would make a concerted effort to work it out.

I was worried I wasn’t going to see him before the long holiday weekend. We’d spent other weekends apart, so this shouldn’t be that big of a deal, but to me it was. I wasn’t spending the holiday with him, so I wanted the next best thing.

Tuesday evening I had a dermatologist appointment to have an ingrown hair taken care of. We were going to attempt to meet after as long as time allowed for it in his schedule.

It turned out he was able to meet. In the rain, I made my way to Lyon to grab a drink with him before he was going out to dinner with business colleagues who were in town for the week.

This was the first time I’d see him following a workday in which he interacted with clients. He looked very smart and super cute. It was all I could do to keep my hands off him. He was happy to see me, but I could tell he was pretty exhausted from a long day. We ordered some small dishes because I was ready for dinner, and his dinner wasn’t until 10:00 or 11:00. The conversation was nice, and we discussed our plans for the weekend. He also expressed concern for the incision on my abdomen from the dermatologist. When we finished, we paid the bill and began to walk towards the PATH/his subway.

We popped into a fun travel amenities shop to check out some of the cool things we noticed in the front window.

We walked a little further and reached his subway. He began to descend the staircase, and I called after him to explain I wouldn’t be joining him since it didn’t take me near the PATH. He walked back up a few steps and gave me a quick kiss as he said goodbye.

It was very unceremonious and not very romantic, but I decided to concentrate on the fact that I got to spend time with him at all before he left.

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