Posts Tagged Sex
Clark Kent and I tried to find a way to be together over the week, but it just didn’t seem to work out. We tried Wednesday, but he had to work late on a pitch. Thursday was out because he was supposed to be going to the hospital to visit his friend who just had his hip replaced. He didn’t even get to do that because work had him there late. We settled on spending Friday together once again.
Friday morning when I arrived at work, two of my team members were walking out of the building. I asked them where they were headed, and they told me to check out the shuttle flyover on the Hudson. I had nothing on my plate for the morning, so I joined them. We staked out a spot and waited for the shuttle to arrive. I realized this was something CK would probably love to see, so I texted him asking if he was checking it out. He worked near the Hudson River and could be there within five minutes. He was completely unaware, so I told him to hurry up.
Unfortunately, he missed it, so I sent him pictures. I made my way back to work and got started with another slow day at the office. I spent a better portion of the afternoon working on the blog to get things squared away for the rest of the Friday releases.
In the middle of the afternoon, CK texted me. “How’s your day going baby?” I told him it was great. “I scoped out the shuttle, and now I’m out to lunch with one of our old interns and the rest of my team. I also have some fun news to share with you.” I learned that morning; one of the girls from my team was going to work at his agency. I couldn’t wait to tell him since she was one of my favorite coworkers. “I could use some fun news,” he added. I replied and told him I was “so excited to see you!”
He replied, “Me tooooooooo. Can’t wait :). What do you wanna do tonight baby? I’m home. Left office early. Gonna go with [his friend] to see [his other friend] in Brooklyn. Can we please do something free/cheap, yet priceless/memorable? That’s the sweet spot I’d like to hit. Well, one of the sweet spots… and by no means the sweetest ;).”
I quickly responded, “Yes. Glad to hear you get to go see him! How bout movie/Revenge night on the couch? You can come to my city oasis. Popcorn, wine, ice cream…” He immediately shot back, “#purrrrrrrrfection. You have no idea how happy you just made me =].” And to add the icing on the cake, I told him, “And, I didn’t shave for you today.” He loved when I had stubble. He liked the way it felt against his skin and liked how I looked with scruff.
When he finished at the hospital and was walking to the subway, he called me. He spent more time there than he expected. His friend was released and they took him home to get him settled in. He needed to go home and freshen up, and then he’d make his way to me.
I’d been sitting around since 6:00 waiting for him to arrive. I prepped the fillet mignons and the chicken for the grill, peeled the carrots and put them in a pot, and I even baked a pineapple upside down cake. After that, I laid on the couch waiting for his call in my motorcycle gear. Around 10:15, I finally got a text from him. Apparently he wasn’t paying attention and rode the PATH back into the city to 33rd street. He was so engulfed in his book, he completely missed the stop.
I was slightly annoyed because I didn’t fully buy his story. The PATH doesn’t simply arrive at Hoboken and turn right back around. It sits there for at least a good ten minutes without moving. He was obviously doing something else before coming over. At 9:45, he tweeted, “I saw the movie before starting the book, and I gotta say, the adaptation translates incredibly well.” He was referring to the Hunger Games he was reading. He was supposed to be in Hoboken at 9:30. How was he tweeting from under the Hudson River? Sure, I was stalking him a little, but I was always waiting for him. I was trying to figure out where he was. He wasn’t aware I was checking out his Twitter account, and I wanted to keep it that way. If he was going to cut me off from Grindr access (he blocked me), maybe I could find another way to check in periodically. (Yes, I’m aware how psycho I sound!)
Finally, he made it. I arrived minutes after him to scoop him up on the motorcycle. No longer would we be taking the long way home. I was slightly annoyed and starving! I hadn’t even begun to cook yet.
When we parked the bike, I tore my helmet off and planted a big kiss on him. We continued to kiss on the street a few minutes before I persuaded him to come upstairs so I could work on dinner. I took everything to the grill and began to cook it while we lay in bed making out. When I started to strip his clothes off, he asked, “We’re going to have sex before we eat?” I explained things needed a little time to cook. “Not sex, but that doesn’t mean we can’t fool around first,” I added. With that I pounced right back on top of his naked body.
In the middle of making out I realized I needed to tend to the grill. I sprang out of bed, threw on a pair of shorts and ran outside. I caught it just in time before becoming a charred disaster. I gave CK a pair of shorts and a t-shirt to wear. We made our way to the kitchen and filled out plates. We sat on the couch and ate off the coffee table while we started Revenge. We’d already both seen it, but I was in the process of delofting my bed while doing so. Some of the show would still be fresh to me.
We spent the remainder of the night on the couch in front of the TV in each other’s embrace while the rest of my roommates and their friends prepared for a night on the town. It was such a nice change when they all vacated the apartment. We started to fool around a little on the couch, and eventually we made our way back to my bedroom, where some of the fun just began.
Warning: The following may be too graphic for some. We started slow, but things quickly progressed. Before long, I was penetrating him. He was incredibly loud and the window was open. I was expecting to hear one of the neighbors yell out. I was also afraid my roommate or her friend who was sleeping over would wake up. His moaning could have woken the building up. I was happy to learn the bed was holding up quite well and not making a ruckus this time. When he needed a break, the make out session resumed. Then things flipped and I found myself on my back with my legs in the air. Before long, he got excited and finished on my chest. I cleaned up, and we lay there a bit in each other’s embrace. “I really want you to shoot all over me like that,” he said. That was all it took. That psyched me out enough that all I could concentrate on was finishing. It was sure not to happen. After long, we were spooning. “Should I turn out the light?” he asked. With that, we dozed off intertwined like a pile of TV cables.
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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…
Life was good. I finally met a man who seemed to be too good to be true. We’d already been on three unforgettable dates, and things were only getting better.
Saturday morning, I said goodbye to Clark Kent when I dropped him off in the city. I wanted to spend every waking minute with him, but things were still fresh and young for us. It’d only been a week. I needed to stop my habit of diving in head first, or I could be in for a world of hurt. Saturday night, I made plans with friends to go out. One of the guys I swam with in college asked me to come by to pregame and then go to the bar with him and some other friends. It’d been months since a request like that came in, so I was ready and raring to go. By the time I got ready to go out after running all my errands, they moved things to the bar. I met the group at Black Bear in Hoboken. These friends are serious triathletes, so they never go out, and when they do, they go to bed early. I also encouraged my other friend P to join us.
When I got to the bar, I sent CK a text to see what he was up to. He responded by telling me to come into the city and spend the night with him. Had he texted me a half hour earlier, I probably would have never entered the bar and would have gone straight into the city. I stepped outside to call him and explain. I really wanted to go see him since I couldn’t get enough of him, but P had just arrived. I didn’t want to ditch her. He fully understood. A small part of me wanted to ensure he wouldn’t get tired of me, so I thought some time apart would do us good.
I went back to the bar and had a good time with my friends. In true fashion, a half hour later, all but P made their way home to go to bed. It wasn’t even midnight yet. I told her all about CK and how amazing he was. I also told her about how I’d ended things with all the other guys. She kept asking things like, “Well, what about [X]? I thought you had a good date?” I explained to her that none of these guys were like my Superman. They didn’t measure up at all. She was impressed with my conviction and wished me luck, but she warned me not to get too far ahead of myself. P and I decided to go to another bar we enjoyed far more, Cooper’s Union, where we sit and chat while our favorite Hoboken bartender serves us.
Just as we were about to leave the bar, it started pouring. We agreed to call it a night instead. She hopped in a cab, and I made my way down the street home. I didn’t get far before I decided to run. I ripped off my soaking wet shirt and ran on my Cole Haans the dozen blocks home. When I got home, I texted CK to tell him about my “TV commercial-like sprint in the rain home.” (The Nike technology in Cole Haans really is amazing btw!). He responded back telling me how much he wished he’d seen me. He told me he was turned on by the mental picture. I achieved my goal. I knew exactly what I was doing when I sent that text to him. I wanted him to want me.

Sunday, I talked to CK, and we made plans for me to spend the night in the city. It made sense since he was so close to my office. I could bring clothes for work the next day and head straight there in the morning.
As the day progressed, the weather deteriorated. It was pouring. I made my way to his place around dinnertime soaked to the bone. I had my giant umbrella with me, but water-soaked my pants from the ground up. He stripped me of most of my clothes when I arrived, and we began fooling around immediately. This, of course, led to sex and some hot, sweaty fun.
I was happy to be spending a rainy night in with him. We had no plans and no obligations. We were simply going to cuddle in his apartment and watch something on his iPad. He offered to make me dinner, and I accepted. He told me his cooking abilities were limited, but he would whip up his specialty for me. I heard a lot going on in the kitchen while I sat in his living room. He wouldn’t let me help. He wanted to surprise me. When I came into the kitchen to give him a hug and kiss, I got my kiss but was ordered back to the couch.
Moments later, he brought me a plate full of salad with chunks of chicken and a tasty dressing. It was very good, and I enjoyed it thoroughly. That night, I would also learn of CK’s sweet tooth. We weren’t even done our salads before he was talking about dessert. He didn’t have anything in the apartment, but there was a bodega on the block. We would venture out into the rain to satisfy a craving for sweets. He offered for me to stay in the apartment and stay dry, but I insisted on coming with him.
We picked up Oreos, ice cream and some cheddar bread sticks and made our way back out into the rain. I was tempted the whole walk back to ask him to hold the umbrella while I ripped my shirt off and ran back to his apartment in the rain. The only thing that stopped me was that I’d have to stand in front of his doorman with no shirt on until he caught up, and I thought it might embarrass him. I chickened out! I was so disappointed in myself. I wanted to show him I didn’t take myself too seriously.
When we got back to his apartment, we dove into the ice cream and Oreos. He made each of us a bowl, and we cracked open the bread sticks. We sat in bed, and when we finished, we cuddled in front of his iPad watching Smash. Shortly thereafter, I dozed off in his arms. It was a perfect rainy night, and I truly looked forward to many others with him while I dreamed the night away.

The next morning, we fooled around before getting ready. While I showered, he made me a bowl of yogurt, fresh berries, honey and granola. It was delicious. He was really taking care of me.
Every moment made me fall for him more and more. We walked to my office together before he hopped on the subway, and I made my way inside. I was head over heels, and things were just starting. The possibilities were endless, and I planned to explore them all…
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On April 20th, my blog turned one year old. I didn’t even realize the milestone was coming up until I looked back at the calendar on a whim one day. I felt the need to celebrate, but I hadn’t told Clark Kent about my blog yet. How could I tell him I wanted to celebrate something I didn’t feel comfortable sharing with him yet?
Instead, I celebrated privately with messages from friends and readers on the blog and over social media. I also had a date night planned with CK.
I invited him to come out to Hoboken for an evening ride on the bike since we weren’t able to do so the previous Sunday. This would be the first time he came out to Hoboken and would see my place. I was quite excited. I came home for work early after a pitch and made sure my place was acceptable.
He had to work slightly later and had to swing by home before he came over. It was a Friday night, and he would be spending it in my bed. As time passed, I sat on the couch patiently awaiting his arrival as the clock ticked on. I had no word from him. I tried calling, but no answer. Where was he? What was he doing? What was taking so long?
Since I was a little broken from previous relationships, my mind began to get creative with where he may have been or what/who he may have been doing. Finally, I convinced myself to put those thoughts out of my head. They weren’t born of any behavior he exhibited. They were simply a spawn of his presence on Grindr. I needed to learn to trust again. The thoughts were gone, and all I could think about was seeing him.
He finally arrived in Hoboken around 8:00. I wanted to watch the sunset with him. The way it reflects off the city skyline is breathtaking, however, the sun had completely set. We’d be taking a ride in the dark.
I picked him up on the bike at the PATH, and we set off along the waterfront to the palisades of Weehawken. I wanted to show him a spectacular view while taking the bike out for a spin. He’d been so excited about it ever since he first learned of its existence.
I really relished having him ride behind me. He pulled himself in tight against me. It was incredibly romantic, and I loved how he wrapped his arms around me. I felt like a great protector.
When we got to the palisades, we parked the bike and took a short stroll along the cliff. We talked while hugging and kissing each other with the spectacular NYC skyline in our periphery. We happened upon a family taking pictures of each other with the city in the background. He offered to take the picture so everyone could get in the shot. I thought it was incredibly sweet of him, and I fell for him a little more at that moment. Every moment with him made me want him all the more. Again, I wouldn’t let myself get too wrapped up in him. It was still early. I didn’t even know if he was interested in a relationship, let alone one with me.
After taking the picture, I told him about my desire to prank tourists in NYC. I would offer to take a picture of them. Just as I was about to snap the picture, I would turn as if to run. When they began to chase after me, I would turn around and snap a picture. It would give them a great experience and a fun story to tell for the rest of their lives, and they’d have a picture to accompany it. He thought this was brilliant and commented on his desire to do this himself.
That’s also when I told him about my life’s to-do list. I told him I wanted to share it with him later because it spoke volumes about me.
We made our way back to the bike and decided to grab dinner back in Hoboken. I knew of a great spot everyone had been telling me to check out but had not been to yet, Bin 14. We rode down the hill from the palisade and made our way back to Hoboken along the river.
I found a spot to park, and we walked to the restaurant holding hands. I wasn’t yet comfortable doing this in Hoboken, but it was something I needed to get over. I would be gay for the rest of my life. If I wasn’t okay showing affection in public, I was in for a lot of headaches going forward. Since we didn’t have a reservation, they asked if we minded sitting outside. I preferred it actually. However, this posed a new situation for me again. We would be street side, and if I wanted to show affection, all of Hoboken could see — Or at least that’s how it felt.
Slowly but surely, I got over this. I was rubbing his knee under the table and exchanging kisses over our meal. I didn’t care who was looking. I still felt a little self-conscious, but I was proud of myself for getting over this.
After discussing wine at length, we agreed upon a nice bottle of Malbec. It took us some time to figure out how to order from the tapas like menu. We still hadn’t figured out our sharing dinner groove, but it was fun to learn this together. I came to find we shared a lot of the same tastes and likes. It also helped we were both share quite an adventurous palette. We ordered a few plates and told the waiter we would continue to order until we had our fill.
The food was great, and the conversation was even better. I was still getting to know him, and I was mesmerized by his smile the entire meal. I was gaga for this guy. If it turned out he wasn’t interested in pursuing a relationship with me, I was going to be heartbroken. I was past the point of protecting myself. I’d already cracked the candy shell. Now, I was in his hands.
We declined dessert, and I made sure to give the waiter my credit card to pay the bill before CK even had a chance to think about it. This date was going to be my treat. I liked this new system. With all the other guys I dated, we both threw down our credit cards and split everything. This felt more like dating and more like a relationship. Each date felt special because one of us was treating the other to it.
We hopped back on the bike and rode back to my apartment. When we got there, it was already fairly late, so we headed straight to my bedroom. I was just finishing removing my shoes when he shoved me backward onto my bed. Since it was up on risers, the bed shifted to the side and collapsed. He was so scared he’d broken my bed, but I assured him it was already an issue. This had already happened with N once before. I’d already been searching for a new sturdy bed not on risers, and this would be the impetus that forced me to address the issue with much more vigor.
We fixed the bed as best we could and continued to make out. It’d been a week since we were last together, so of course we were both horny for each other. I hadn’t had sex since we last saw each other, but I wasn’t sure I could say the same for him. We hadn’t crossed the monogamous relationship bridge yet, and I had no right to ask that question yet. We’d only been dating a week. One step at a time I told myself.
Warning: The following may be too graphic for some. Regardless, we found ourselves naked, and I was grinding on his backside. Our passion was elevated to a new level, and we were all over each other. I couldn’t get enough of his body — It was purely amazing. I’d never been with someone so handsome, so sexy, so fit, so sexual. He was like nothing I’d ever experienced before.
Eventually, he reached behind himself, grabbed hold of my manhood and directed it in until I found myself deep inside him. Amazing sex ensued until we both had our fill.
I was incredibly happy once again. I had a man who could come to dinner and hold a great conversation, and a man who could satisfy all my sexual desires. He was the best of both worlds.
With that, we cleaned up and climbed back into bed. I was happy to finally be sharing my bed with him. This would be the first time in a long time my California king was being put to good use. We fell asleep in each other’s arms. He was my little spoon. Throughout the night, we changed positions many times, but never fully woke up. We slept great.
When we woke in the morning, CK had to head back into the city to begin apartment hunting. He’d been putting it off and needed to put his nose to the grindstone. We stopped for a delightful breakfast at Ganache while we got to know more about each other. When we finished, we rode through the Lincoln tunnel into the city. I couldn’t drop him in front of his building because there was a parade going up his street, so we said goodbye to each other in front of the Empire State Building. I couldn’t think of a more romantic way to begin my Saturday…
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It was happening. I was falling for this great guy who managed to find me on Grindr. Who would have thought? I was still quite unsure how he felt about me, but I still had no luck finding a single fault in him.
I was prepared to take things slow with Clark Kent. I saw no need to rush things. Dating all these men in NYC helped me relax and enjoy things in real time. I didn’t need to think about what was coming next. I only needed to think about what was happening now. I was enjoying his company immensely.
That being said, I needed to tie up some loose ends. I had no desire to see any other guys while seeing CK. He was great, and he kept my attention. I didn’t want to wander and philander. I wanted him and him alone.
The first loose end to tie up was Southern Drawl. It took me two weeks to realize he wasn’t right for me. He’d gone home to the South to visit family, and it offered me a necessary reprieve from him. He sent me a few pictures from down there and a few texts. I responded in turn, but they were very short. When he asked how my day was going, I responded with what I’d done that day. “Well thanks for the play by play. Enjoy the rest of your week. Let me know if you wanna hang out again when I get back,” he responded. I wasn’t going to take that lying down. “Whoa! Where’s the hostility coming from?”
He apologized and explained he didn’t mean it that way. “How bout enjoy the rest of your week, and I look forward to hanging with you sometime when I get back 🙂 xoxo,” he added. I told him we only knew each other a short period of time and warned him not to get ahead of himself. I was using this turn of events to drive a rift between us.
He texted: “Well, that was a joke, but point taken. Wow! So I’ll go back to your statement from a few months ago. Ball is in your court. Otherwise, you won’t be hearing from me.” I reminded him to recall who picked that ball up again in the end. Then came the clincher: “Well, I guess I dropped it cause I’m being drunk and stupid again. Oh well. That ‘let’s not get ahead of ourselves’ $hit just irked me. So Grindr away, do your thing and hit me up if you want to hang out sometime. No hard feelings if not. I’ve learned my lesson about guys in the city and was a dumba$$ to think you could be different. But that’s my fault, not yours.”
I had my out. I wasn’t going to let him talk to me like that. I wasn’t going to try to foster a relationship with someone who made such accusations. We’d known each other two weeks, and I was already getting drunken rants. This wasn’t a good sign of what was to come.
In my book, he was done. I deserved an apology, and until I got one, I wasn’t going to communicate with him. I was going to give him a day to apologize. Just when I was about to inform him he’d killed any chance with me, he texted, “Had a rough night last night. Whiskey on the river. Bad combo.” This was an excuse, not an apology — Unacceptable. Two days later, I responded, “Still waiting for an apology. You were way out of line, and I did nothing to deserve your assumptions!”
He apologized profusely and cited more reasons why he’d been so harsh. “You’re an incredible guy, but if you never want to hang out again, I get it. But, for the record, I did miss talking to you and stuff this week,” he texted. He still seemed to be making excuses for himself. I didn’t respond. A day later, he said, “So, I guess that’s it then, huh?”
I was done with him. I told him from the start I don’t play these games. It seemed to be his mode of operation. I simply replied, “I think we should try friends for a bit. I get that you were drunk, but drunk minds speak a sober heart…” He asked if we could talk and tried calling me. I texted back telling him I was still at work, which was the truth. He started playing the martyr and going off on me. I told him to stop being so melodramatic. When I left work to grab dinner before returning to the office, I called him.
We talked for about a half hour. I explained to him all the things he did and how they were wrong. He didn’t even realize all the things he was doing. I pointed out how he was unloading all his baggage on me and how unfair that was. I did nothing to deserve that. I proposed we take a big step back and work on a legitimate friendship first. In reality, I was pretty much done with him. I was purely being polite. He was a decent guy, but he was a little broken.
He wasn’t satisfied with this and wanted to redeem himself, but I gave him an ultimatum. I said we could either be friends, or we could be nothing. That was his choice. It all depended on his future actions toward me.
As time progressed, and I was too busy to hang out with him when he asked me to, he began getting very snippy with me. I suggested a happy hour drink, but that went south fast. His sarcasm came out in full force until I said, “On second thought, maybe that was a bad idea.” I pointed out to him how combative he was toward me and said obviously this wasn’t going to work out between us. I gave him my work address so he could mail me back the sunglasses he borrowed from me. I didn’t even want to have to go through seeing him again. He’d gotten on my last nerve.
He told me how hurt he was by the whole thing, but I pointed out to him it was all of his own doing. He never treated me with trust and respect before he even had any reason to doubt me. I wasn’t going to take any more of his crap. I’d already dealt with enough. He couldn’t understand how his going off on a drunken tirade toward me was such a deal breaker. “It just doesn’t add up,” he said.
He was clearly hurting. I know this because he typed it out in black and white. “I’m miserable right now,” the text read.
He told me to delete him from my phone and he planned to delete me from his. In another instance, he said, “And for the record, I’m truly upset. You’re one of the good ones. And I’m a piece of $hit to write off apparently.” He wasn’t going to guilt me into liking him again. It was OVER!
That left two other loose ends to tie up. I had been meaning to text the Jersey City athlete for some time. He seemed like a really nice guy, and we got along great, but he was no CK. I needed to be fair to him and let him know what’s up. I texted him and said, “Hey dude. I def owe you a text and an explanation… I had a great time with you that one night, but at the same time, I’d also just met someone. I want to let you know I think you’re a great guy, but things have progressed. And, I want to give this a shot. I hope you understand and don’t take it personally! And I apologize since this message is long overdue!” He responded quickly, saying, I completely understand. I’m in a similar situation myself actually. When it rains, it pours, right?” I was happy to hear he was cool with things. I added, “LOL. Yes. Glad to hear. Maybe we can hang out again sometime and build a friendship?…” He responded, “I’d like that.”
After that, we chatted a few times on Facebook. I asked him how things were going with his new man, but learned the guy simply stopped responding to him. Turns out it was one of my neighbors. We still haven’t found time to hang out as friends, but I’m sure it will happen sometime. I need to have a gay friend nearby these days…
Middle Eastern and I hadn’t seen each other in quite some time. He’d text periodically to see how I was doing, but we made no plans to see each other. I was still a little put off from the time he told me he’d come over and never did.
At one point, he asked if we could hang out again. I told him that would definitely work. I was not opposed to hanging out, but that would be all that transpired between us. No more sex. No more intimacy. We’d purely be friends. It wouldn’t be easy, because we did have a great deal of fun in bed, but I had faith I could do it.
The time came for me to tell him I’d met someone else. “So anything new?” he texted one day. “Actually, yes. I’ve recently started dating someone. Been trying to figure out a way to bring it up… I hope you understand,” I responded. Immediately, he shot back, “Well, I’m definitely happy for you :). And I’m glad you told me. Kinda stung a little, not gonna lie about that.”
I felt really bad. I did like him a great deal, and I didn’t want to hurt him. There was no easy way to tell him, so honesty would be the only way to go. “Sorry! Hence my hesitation. You’re a great guy, and I hope we can be friends!! You kinda disappeared on me. Seemed like you met someone else. I put myself out there and met someone…” I added. He expressed how he was really happy for me and pointed out it just wasn’t meant to be. I told him he deserved someone young and fun and told him I really meant it about being friends. “Maybe. When I get over you. Of course I wanna be friends with you. We discussed grabbing a drink sometime, but that still had yet to happen. Some day we’ll find the time to hang out and become good friends.
And just like that, all loose ends were tied up. It wasn’t easy, but it was over. Now, I could concentrate all my efforts on the new man in my life — Clark Kent. The man who cut the roster down to one.
We tried to make plans to see each other during the week, but it never seemed to work out. Instead, we’d have to wait until the weekend to see each other again. It wasn’t easy, but it would have to do. I didn’t want to do anything to scare him off. I was too infatuated to lose him already. I would be patient. I would wait for things to happen naturally. I would finally do things right, and hopefully, by putting everything I’d learned from all the men I dated, I would find true love.
P.S. I still don’t have my sunglasses…
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Sunday, I made plans with my Superman — My Clark Kent. I was very excited and could hardly wait.
I barely knew him, but I could already tell we were quite a match. On top of that, we weren’t even done the first date before he planned to see me again. It was his suggestion for us to catch The Hunger Games Saturday morning while we had breakfast.
I texted him and invited him to come over to Hoboken. We would take the motorcycle out for a ride before the movie. I ran a lot of errands that morning in anticipation of his arrival later in the afternoon. As the day progressed, the weather looked like it would cooperate less and less. The sky was covered with clouds and the wind picked up significantly. It looked like it would rain any minute.
I texted CK and suggested we hold off on the ride, and I just come into the city to see the movie. It would make things less complicated, and it would give him something to look forward to in the future.

He agreed with the new plan. I met him at his apartment with plenty of time to catch the movie. He suggested we hit up the rooftop since I didn’t get to see it the first time I was there. How could I say no to that? When I got to his apartment, we went directly up to the roof. We spent time checking out the sights, cuddling and taking pictures like we’ve been a couple for a year already. I was crushing hard!
We sat and talked, and he suggested we catch a later showing so we could relax and not have to rush to the theater. I wasn’t going to object to anything at this point. I was so happy. I was just going to go with the flow.
We finally made our way to the theater. He insisted on buying my ticket. I protested since there was no reason I couldn’t pay for myself, but he continued to insist. He wanted this to be his treat. I relented, but was sure to pick up the tab for the pretzel bites and soda.
We made our way into the theater and got great seats. Almost immediately, the PDA began between us. It wasn’t gag yourself PDA. We were simply holding hands or caressing each other’s arms. It was my kind of PDA. I was quite enjoying myself!
When the movie was over, we made our way to the street and discussed the film while we walked. This was his second time seeing the movie. He expressed interest in reading the book, and I strongly encourage him to. I was already part of the way through the second book in the series of three.
We held hands while we walked and at times put our arms around each other. I could hear a lot of people making comments, and some even began to shout or hoot and holler at us. A few of the comments were jeers and a few were shouts of support. This was not something I was used to, but it was something I would have to learn to shrug off. I’d walked through the city being affectionate with other guys before, but it never gathered this type of reaction. At one point, CK acknowledged the comments, asking, “Are they still honking at us?” I told him I thought so, and we kept walking. Frankly, I was a little surprised by it all. We were in midtown west — Smack dab between Chelsea and HK, two of the gayest neighborhoods in NYC. I had a feeling a lot of the commenters were out-of-towners, and many of them were young guys.
When we got away from the crowds, he commented how he liked how I was into the hand holding. “Not all guys are into it. I’m glad you like it,” he added. I told him I liked little signs of affection, but I wasn’t into the far more obvious public displays. I told him I’m not much for making out in public.
He also mentioned the idea that had we planned better, I could have brought clothes to wear to work the next day and spent the night, however, he was happy we weren’t taking things for granted. He was happy with the pace of things, even though he wouldn’t have been opposed to sharing his bed with me.
We stopped by Pinkberry on the way back to his rooftop as per his request. We ordered ice cream and shared spoonfuls with each other as we walked up the street. When we got back to his place, we headed straight to the roof.
We laid on one of the outdoor couches together and got comfortable while we ate our ice cream. We talked for a while before we ended up making out. Things stepped up to the next level when he undid my belt and began orally pleasuring me with one eye on the door. It was risky but I wasn’t fully exposed. I liked his passion and excitement. I’d finally met my match in terms of a decent, normal guy with a healthy sexual appetite.
After some time, he asked, “You wanna continue this downstairs in my apartment?” I told him I was totally game, and we descended the stairs.
Warning: The following may be too graphic for some. It wasn’t long before we were both naked in his bed. There was significant foreplay before he asked if I wanted to penetrate him. I was completely engulfed in our passionate romp and nodded my head in definitive agreement. “Yes! Like no other!” I added.
Then, I’m not sure how things switched so quickly, but as I was grinding on his backside, and stopped to put on a condom, he turned to me and said, “Can I f*ck you?” A long time ago, I made a rule for myself I would not bottom for a guy unless we were in a relationship. It wasn’t something I really enjoyed, so only special guys would receive the privilege. I had very strong feelings for him. I wanted to share something special with him already. I could hear A’s voice in my head telling me no sex until the third date, but that voice in my head was no comparison to the passion of my other head. After all that thinking, I said, “Yes.”
Like that, he started making out with me, and he had me on my back. While we were making out, I set the open condom down on the bed. He was already putting it on. I thought he was going to top me after I topped him. I didn’t realize I was giving up my position first. I was a little disappointed, but I let it happen anyway.
I told him it was a very long time for me since any guy had been inside me. I told him he’d have to go VERY slow. He began to slide in when I gripped his leg and implored him to stop. He told me to relax and just hold it there, but I insisted he pull out. I needed a break before we could continue. I know he thought it would be better if he simply held it there, but I was being painfully stretched. He wasn’t exactly a small guy — Quite the opposite. He pulled out, and I could see the disappointment on his face. He thought that was it, but I wasn’t giving up that easily. I just needed a second to relax again. He began kissing me in a caring way. It was as if it was his way of saying, “I never want to hurt you again.” When I regain composure, I directed him to begin again. Delight spread across his face at this news.
This time was much easier. He slid in with no problem, and began gyrating. It’d been some time since my prostate was stimulated like that, so part of it was discomfort and part was unexplainable pleasure. I never finish from bottoming, but I always have a full-body experience. I rarely can walk afterwards — Not because I’m so sore but more so because my legs go limp.
He continued until he was close, pulled out, ripped off the condom and shot all over my chest. It was very hot to watch him explode with gratification. He expressed how great everything felt, and we both laid there incapacitated. He told me how awesome he thought it was that I would flip so readily and let him top me. I told him I thought it was the best way for any healthy relationship. Both partners get to experience it all. Even though I didn’t always enjoy bottoming, I found it to be the ideal situation.
We cuddled for hours after that. We even dozed off for a period. When I woke, it was two am. I checked the schedule for the next PATH and made sure I was on it at 2:30. I said goodbye to him with a very passionate kiss, and we talked about when we’d get to see each other next. It was clear I couldn’t get enough of him. Now, the question was, did he feel the same way about me?
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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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Monday morning I woke up. Since I wasn’t wasting so much time messaging guys on Grindr, I felt so much freer. I had no idea how much time I spent searching and complimenting guys on their torsos in hopes they’d see something they’d like and allow me to ask them out on a date.
I was also thrilled since I got to sleep in my own bed the night before. My parents came to visit for Easter weekend, and I gave them my bed. Sunday night, they offered to get themselves a hotel room so I could get a decent night’s sleep for work Monday. After I dropped them at their hotel with my sister, I came home and passed out. I love my parents, but I was happy to have my place back again. I’d spent the weekend playing tour guide. It was exhausting.
Even though I wasn’t sending out messages on Grindr didn’t mean I wasn’t checking them. I fired it up to see if my prince charming would ask me out on a date. I found quite the opposite. I blocked a fair amount of guys before I found an interesting message. I spent the weekend being celibate. One of the guys on Grindr seemed pretty normal and chill. We began to chat a bit before he offered to blow me. Like that, I was back in it. I had done such a good job of staying away from the simple Grindr stranger hookups, but I was horny after a weekend of being good. I made an exception of course and accepted his offer to blow me. What harm was there? I could enjoy myself before work and have a great day. “Sure,” I said in reply.
I gave him my address, and he drove over to my place on his way to work. I quickly hopped in the shower. He buzzed, and I called him up to my apartment. I quickly dried off and got dressed. When he got to the door, I brought him right into my room. I was wearing gym shorts and a tank. We made our way to my bed, and I sat down. Just then, he looked at me and said, “Sorry bud. I’m just gonna go.” With that, he turned around, sped out my door and left without another word.
I felt so rejected. What was it about me that scared him off. He made it all the way to my bedroom before darting. Was I that repulsive? Why the sudden change of heart!? I felt so dejected! My self-esteem shot down to an all-time low. This had never happened to me, and I suppose it was karma for all my Grindr trysts. It was bound to happen at some pont. I thought about all the times I wanted to do what he did and didn’t. I’d always regretted not standing up and walking out, but suddenly I no longer regretted it. I would have put those guys in a tailspin like I was going through. I did have to respect him honesty however. It was a catch 22.
I was horny from the thought of getting off before work, so I quickly finished myself off and got ready for work. I was disgusted with myself for bending my new rule, especially since I didn’t get anything out of it. Served me right!
That night I had a date scheduled with a guy I’d been chatting with for over a year. We met through Grindr and tried to grab drinks before I met N, but when I started dating him, things fizzled out. We chatted periodically on AIM, but nothing ever materialized. I even contemplated making a career shift to event planning, which this guy did, but we were never able to get together to talk about it. We simply kept it to a digital relationship. When things with Smiles ended, I began to look back at the guys I’d been chatting with. I hit him up and asked him out.
We made plans to meet at Ariba Ariba after work for margaritas and a bite. During the day, I stalked him a bit on Facebook. I noticed he was a camera whore. He took so many pictures in so many gay bars. He was totally a part of the scene. He was a fixture. I worried this would be a roadblock, but I was still optimistic. Maybe I could learn to love it.
I arrived ahead of him and waited on the corner. When I saw him arriving, I noticed how attractive his smile was, followed by how short he was and how “fun” he dressed. He was very cute. We awkwardly said hi and made our way inside. He asked if I was hungry, and I told him I hadn’t eaten, so we agreed to grab dinner on top of drinks. We were seated at a tight table and settled in.
We mainly began talking about work. It was very awkward. Considering we’d chatted so often online, you think we’d have been able to jump right in — Not the case. There were so many awkward pauses. I was struggling to find topics to talk about with him. He wasn’t exactly spurring the conversation on.
We started to talk about TV and what we watch. I thought that would be a safe topic and would spur further conversation. That only led to learning we had very different entertainment tastes. He watched a lot of Bravo TV like Housewives of… and other shows of the same ilk. I was more into the mainstream network TV. I wanted to have more in common with him, and I could tell he did too based on comments, but it was a bit of a struggle. I asked so many more mundane questions followed by mundane answers.
We ate our meals while we talked, but it was far from a great dinner. It was pleasant. The food was good, but there was no flow to the date. I was ready for it to be over. I was a bit disappointed since I thought we’d get along swimmingly. We just didn’t have good chemistry.
When we finished, we paid the bill and made our way out. We began walking through Hell’s Kitchen south together. He lived that way, and I was headed to the bus. When we got to a shop along the way, Tagg, he needed to run in and grab something for a friend’s birthday. I went in with him since I had nowhere to be. We had some fun chatting about random things in the shop. He made his purchase, and we continued south. When we got to his intersection, we exchanged a kiss goodbye, and he made a comment about hanging out again sometime. I agreed, but in my mind it would be under a friendly premises.
We texted afterwards, but was pleasantries and formalities. We exchanged that we each had a nice time, but that would pretty much be the end of us.
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In a strike of luck, in terms of my desire to turn my dating/sex life around, the timing of a family trip could not have been better planned. My parents, my sister and I were heading to Virginia to visit my aunt, uncle and cousins. The purpose of the trip was to see the cherry blossoms in Washington DC.
It was a fun trip. I got to see my cousins’ girlfriends and their children, many of which for the first time. Even though the cherry blossoms had already fallen due to an early bloom, it was still nice to get away and relax.
While driving back to New Jersey with my sister, I began attempting to line up dates with all the guys I’d been talking to before I left. As far as going on dates, the trip came at a bad time because it put a roadblock in the momentum. I kept up with the texts from the southern boy I’d gone on one date with so far. We were trying to line up a second date, as well as a few first dates with some other men I’d chatted with.
I got back to town on a Monday afternoon and tried to dive right into the dating. One of the guys I’d been chatting with was a doctor I met on Grindr. We exchanged pictures. He was very good-looking, very well-spoken and very charming. His response to my picture was, “Matthew McConaughey party of one?!” I was incredibly flattered, and suggested he consult with an optometrist friend. Although he had some promise, I wasn’t all that excited to meet him. I was going in with an open mind, but the fact that he was a doctor was somewhat of a turnoff. He would have no time for me, and I have come to realize I need someone who will be around and spend time with me.
We texted back and forth to nail down plans. As the workday was ending, I asked him what he wanted to do. He responded, telling me, “I honestly feel like I need a quiet night in. A bit drained here but would definitely like to have you over for drinks and conversation if you are up for that?” It was a bit unconventional, but I told him I was game. He gave me his address, and we set a time at 9:00pm.
I made my way into the city, bottle of red wine in hand, and walked to his apartment. I called Boston, and he shocked me by picking up. I wanted to hear how his birthday went and catch up. He further shocked me with a story involving an on-duty officer and himself that made me so proud. It was nice to hear Boston letting loose.
As I walked up to his apartment, I hung up with Boston. He lived in a very nice building. He answered the door, and we exchanged hugs. He had a gorgeous place. I came in and made myself comfortable on the couch while he opened the bottle. I felt quite overdressed when I noticed him in sweatpants and a t-shirt. I was jealous. I removed my shoes and sat Indian-style on the couch.

He was far more attractive than his pictures. His tight t-shirt showed off his chiseled body, and his face and smile looked very similar to Taye Diggs. I was slightly mesmerized.
It wasn’t long after we began talking that he let his guard down. The flamboyance came bubbling up, and it was really turning me off. I immediately lost my attraction for him. I could see us being friends, but I could never date someone like that.
We sat on opposite ends the couch talking the whole time. I learned about his job and what he does in his free time (which wasn’t much since he didn’t have much of it). He told me his specialty, and that dominated a majority of the conversation from then on out. Ironically, his specialty was relevant to me, and we got on the topic of safe sex and HIV for over and hour. It was incredibly educational on two levels. I learned a few things about HIV transmission and the disease itself, and I learned how little I know about the stuff I was so cavalier about days prior. I thoroughly enjoyed our talk, but I wasn’t attracted to him as a potential man to date. I would, however, love to keep him around as a friend.
It was late, and I needed to go home. He needed to go to bed. He walked me to the door, and I said goodbye with a kiss. He pulled back and made a comment on how he wished he’d only done that sooner. He really liked it and came back in for more. He was a good kisser too. I walked to the PATH and then walked home, and it took me a while to get there.
The next morning I noticed a text from the doc. “Off to sleep here, but just wanted to say thanks for an awesome date! I really had a great time meeting you.” I apologized for my lack of response and told him I was at the allergist to getting poked with various things to find my allergies. We exchanged small talk on the subject, and the conversation fizzled out. That was the last I’ve heard from the good doctor…
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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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Things with Middle Eastern certainly weren’t leaving us holding hands skipping down the beach. I really liked him, but I never really saw the potential for a strong relationship with him. I would like to think I wasn’t leading him on. I would like to think he was well aware we were casual and enjoying each other’s company. But, who could be sure what’s going through someone else’s head?
I invited him to come over for dinner Tuesday night after work. A part of me was horny, and he is really great in bed. Another part of me wanted his companionship — Just someone to watch TV with and cuddle. He was in class and would come by a little later. This worked out because it would allow me time to make us food.
When he arrived, we immediately went into my bedroom and fooled around. We didn’t have sex, but there was a lot of kissing and groping and cuddling. He told me about his day, and I got him caught up on what was going on in my life since I’d last seen him. When we had our fill, I tossed him a pair of my shorts to put on, and we made our way back out to the living room to eat and watch TV. I learned he’d already eaten, and I made a plate for myself, and we sat on the couch watching TV.
When my roommates made their way to bed, and it was getting later, I turned off the TV and led M.E. to my bedroom. We hopped into bed and watched some more TV before we were no longer watching because other desires took over. Warning: The following may be too graphic for some. The kissing and heavy petting led to stronger desires. I grabbed a condom and lube, and we went at it. It was extra passionate this time, We were thoroughly enjoying each other. We went through many permutations of positions. Every one was better than the last. His body felt amazing, and he seemed to really be enjoying it.
I was disappointed he never finished with me, but I fully understood. I’m not quite sure he did. “I don’t know how to explain it. It’s like I have a full-body experience, but I never cum,” he expressed. I told him I knew exactly what he meant. I never brought it up myself, because I knew that was the exact opposite of a solution. In all the times I’d been with him, he never finished. He told me it was nearly impossible for him to accomplish after I penetrated him. We both went to bed that night without finishing. The sex was so great I didn’t feel the need to finish myself off. I was also hoping for some morning nookie, so I knew I would be hornier if I left it til the morning.
In the middle of the night, he did something that woke me up. I glanced at the clock and saw it was nearly four am. He began grinding against me and grabbing hold of my member. He was massaging his backside with it. When I woke, I began to engage in this activity as well. I was grinding on him until all of a sudden I found myself inside him. It was pure bliss. We both enjoyed this in the spooning position for some time before finally withdrawing and going back to sleep.
In the morning, we woke to the sound of my alarm. I had to go to work. He didn’t have any obligations that morning. As I predicted, I woke up hornier than ever. The middle of the night sex had my engine revving extra hard. We engaged in a lot of foreplay. I started orally pleasuring his backside before climbing on top of him and penetrating him once again.
This time, I did not reach for the condom. I know this isn’t the smartest. I let passion get the better of me. In the back of my mind, I trusted him. I didn’t think he was having sex with anyone else. I also know I’d done a lot to make sure I was protected with all the sex I’d recently engaged in. I had no signs of an STD and no reason to believe I contracted HIV.
We let out synchronic moans of pleasure. It felt amazing. We had lots of sex before he needed to take a break. He caught his breath as we exchanged how much we enjoyed sex together. When he was good again. He laid on his back while I lifted his legs up on my shoulders. I enjoyed looking into his eyes and kissing him while we had sex. He was pretty amazing in bed, and I loved his passion. We stopped when he needed a break again.
I didn’t want to be late, but I still wanted to continue the fun. We hopped in the shower and bathed every inch of each other’s bodies. I was still incredibly horny, and I knew I wouldn’t be able to concentrate at work if I didn’t finish. I tossed him down on my bed and pulled his towel off. We got right back into it for a bit before I withdrew and finished myself off. He was thrilled. He really enjoyed all of it, but I could see there was something else going on there. I knew we didn’t discuss the lack of protection, and it needed to be brought up. I was in a rush to get to the PATH to go to work, so I made a mental note to call him later to discuss.
He gave me a ride to the PATH, and I kissed him goodbye. When I got to the other side of the river, I’d received a text from him expressing his concern. He wasn’t worried, but he just wanted to discuss it. I explained to him I too had been meaning to bring it up, and I’m glad he did. I told him I’d always used protection with anyone else I’d been with, and he needn’t worry. I told him I trusted him, and after it happened in the middle of the night, I let my guard down about it in the morning. I told him I was going to get tested in the next few days so both of us could be certain he had nothing to worry about, and he told me he planned to go as well. He told me the last time he had been tested, and I told him mine. I had a strong feeling I had nothing to worry about with him, so scheduling a test felt more routine than anything. He’s a bit younger, so I’m sure he was worrying a bit more. I wanted to be sure to get results as soon as possible so I could give him peace of mind.
He was a good kid, and I really enjoyed being with him. I never wanted to do anything to hurt him. After we chatted over text, he told me he felt a lot better and wasn’t so worried. I apologized for putting him in that situation, and I told him we should discuss things after we both got our results back. I found it to be a very healthy conversation we probably should have had earlier, but I was happy we had it.
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Superman Returns
Posted by One Gay at a Time in Gay Dating on May 30, 2012
Sunday, I made plans with my Superman — My Clark Kent. I was very excited and could hardly wait.
I texted him and invited him to come over to Hoboken. We would take the motorcycle out for a ride before the movie. I ran a lot of errands that morning in anticipation of his arrival later in the afternoon. As the day progressed, the weather looked like it would cooperate less and less. The sky was covered with clouds and the wind picked up significantly. It looked like it would rain any minute.
I texted CK and suggested we hold off on the ride, and I just come into the city to see the movie. It would make things less complicated, and it would give him something to look forward to in the future.
He agreed with the new plan. I met him at his apartment with plenty of time to catch the movie. He suggested we hit up the rooftop since I didn’t get to see it the first time I was there. How could I say no to that? When I got to his apartment, we went directly up to the roof. We spent time checking out the sights, cuddling and taking pictures like we’ve been a couple for a year already. I was crushing hard!
We sat and talked, and he suggested we catch a later showing so we could relax and not have to rush to the theater. I wasn’t going to object to anything at this point. I was so happy. I was just going to go with the flow.
We finally made our way to the theater. He insisted on buying my ticket. I protested since there was no reason I couldn’t pay for myself, but he continued to insist. He wanted this to be his treat. I relented, but was sure to pick up the tab for the pretzel bites and soda.
We made our way into the theater and got great seats. Almost immediately, the PDA began between us. It wasn’t gag yourself PDA. We were simply holding hands or caressing each other’s arms. It was my kind of PDA. I was quite enjoying myself!
We held hands while we walked and at times put our arms around each other. I could hear a lot of people making comments, and some even began to shout or hoot and holler at us. A few of the comments were jeers and a few were shouts of support. This was not something I was used to, but it was something I would have to learn to shrug off. I’d walked through the city being affectionate with other guys before, but it never gathered this type of reaction. At one point, CK acknowledged the comments, asking, “Are they still honking at us?” I told him I thought so, and we kept walking. Frankly, I was a little surprised by it all. We were in midtown west — Smack dab between Chelsea and HK, two of the gayest neighborhoods in NYC. I had a feeling a lot of the commenters were out-of-towners, and many of them were young guys.
When we got away from the crowds, he commented how he liked how I was into the hand holding. “Not all guys are into it. I’m glad you like it,” he added. I told him I liked little signs of affection, but I wasn’t into the far more obvious public displays. I told him I’m not much for making out in public.
He also mentioned the idea that had we planned better, I could have brought clothes to wear to work the next day and spent the night, however, he was happy we weren’t taking things for granted. He was happy with the pace of things, even though he wouldn’t have been opposed to sharing his bed with me.
We laid on one of the outdoor couches together and got comfortable while we ate our ice cream. We talked for a while before we ended up making out. Things stepped up to the next level when he undid my belt and began orally pleasuring me with one eye on the door. It was risky but I wasn’t fully exposed. I liked his passion and excitement. I’d finally met my match in terms of a decent, normal guy with a healthy sexual appetite.
After some time, he asked, “You wanna continue this downstairs in my apartment?” I told him I was totally game, and we descended the stairs.
Warning: The following may be too graphic for some. It wasn’t long before we were both naked in his bed. There was significant foreplay before he asked if I wanted to penetrate him. I was completely engulfed in our passionate romp and nodded my head in definitive agreement. “Yes! Like no other!” I added.
Then, I’m not sure how things switched so quickly, but as I was grinding on his backside, and stopped to put on a condom, he turned to me and said, “Can I f*ck you?” A long time ago, I made a rule for myself I would not bottom for a guy unless we were in a relationship. It wasn’t something I really enjoyed, so only special guys would receive the privilege. I had very strong feelings for him. I wanted to share something special with him already. I could hear A’s voice in my head telling me no sex until the third date, but that voice in my head was no comparison to the passion of my other head. After all that thinking, I said, “Yes.”
Like that, he started making out with me, and he had me on my back. While we were making out, I set the open condom down on the bed. He was already putting it on. I thought he was going to top me after I topped him. I didn’t realize I was giving up my position first. I was a little disappointed, but I let it happen anyway.
This time was much easier. He slid in with no problem, and began gyrating. It’d been some time since my prostate was stimulated like that, so part of it was discomfort and part was unexplainable pleasure. I never finish from bottoming, but I always have a full-body experience. I rarely can walk afterwards — Not because I’m so sore but more so because my legs go limp.
He continued until he was close, pulled out, ripped off the condom and shot all over my chest. It was very hot to watch him explode with gratification. He expressed how great everything felt, and we both laid there incapacitated. He told me how awesome he thought it was that I would flip so readily and let him top me. I told him I thought it was the best way for any healthy relationship. Both partners get to experience it all. Even though I didn’t always enjoy bottoming, I found it to be the ideal situation.
We cuddled for hours after that. We even dozed off for a period. When I woke, it was two am. I checked the schedule for the next PATH and made sure I was on it at 2:30. I said goodbye to him with a very passionate kiss, and we talked about when we’d get to see each other next. It was clear I couldn’t get enough of him. Now, the question was, did he feel the same way about me?
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