Posts Tagged boxer briefs
Nearing the End of My Rope
Posted by One Gay at a Time in Gay Dating on February 1, 2013
Tensions were high between CK and I. Nearly every night, we’d find something to argue about. Although it didn’t always result in an explosive fight, there always seemed to be some kind of noise in the background. The honeymoon was officially over.
When we woke in the morning, CK apologized for the night before, as did I. As we got ready for work, we both agreed underwear was not something we should be fighting about. After making us breakfast, we ate, showered together, got dressed and made our way to the PATH.
A day prior, CK got tickets to see Hot Chip in Brooklyn from a coworker . He asked if I was interested in going. We had already planned to head to Brooklyn to visit Hip since he was recovering from his second hip replacement surgery, so I said, “Sure. Why not?”
While we were at work, we nailed down plans via text and phone. Since I finished much earlier than he did, I hopped on the subway and made my way to his office. He wasn’t quite ready yet, so I asked for his coffee order and hit up Starbucks. I didn’t sleep very well the night before, so I needed something to keep me up and give me the energy to be a fun date.
While riding the subway out to Brooklyn, I asked CK if he requested the time off to join my family on vacation. He reacted to the question as if this was some big surprise. I’d only been asking him about it for a solid month. When he asked me to take time off and book a flight to Miami for his nephews birthdays, I did it without question. Now that I was asking him to take time off to be with me and my family, he didn’t think he could get the time off. I was p*ssed! I found it quite selfish. If he’d requested the time when I originally asked, we wouldn’t have gotten into the argument that ensued. As I said, we seemed to be fighting about everything.
The rest of the ride wasn’t pleasant. It grew to far higher proportions when we got off the subway. I wanted nothing more than to get right back on the subway and make my way home. I no longer had any interest in going to the concert, and I told him that. It takes two to fight, so I take half the responsibility, but he was being rude and treating me in a way I wasn’t willing to subject myself to. As a result, I skulked behind him as we walked through Prospect Park. As he yelled at me for not helping him navigate our way to the concert, I shouted back, “Fine. Just go without me! I don’t want to go anymore. I’m not going to have any fun.” I wanted nothing to do with him or Hot Chip.
I think he understood I was serious and responded by apologizing. “Can we just get past this tonight?” he asked. “Do we have to sacrifice our entire night over this fight?” I didn’t want to just put on a happy face and grin through it. I was angry, and to be honest, I wanted to go home out of spite. The concert was something he wanted to go to, and just as he didn’t put in the effort to come with me on vacation, I wasn’t going to come to the concert. I realized how unproductive this would be, so I agreed to go (not before numerous attempts to make my way back to Hoboken).
When we finally made it in to the concert, CK bought me a few beers, and we cut through the crowd to watch the concert already in progress. Surprisingly, I started to have a better time. Admittedly, I’d never heard of the band before we arrived, and I didn’t recognize any of their music. The fighting ended, and CK was being affectionate. We even made a few friends while moving from place to place among the crowd and managed to bum a smoke off some nice guys.
When the concert was over, it was far too late to visit Hip. I felt really bad considering he was the original plan and reason for the trip to Brooklyn. I wasn’t thrilled we sacrificed his visit for a concert, but in the end, it was CK’s decision.
On the walk to the subway, we found ourselves in a situation once again that birthed yet another argument. When we were a safe distance away from the situation, I began to calmly explain how p*ssed I was at him. Once again, he didn’t think it was a big deal and almost brushed it off as if I was overreacting. I didn’t care. To me, it was so much more. I told him explicitly how much I didn’t like these types of situations, and he completely disregarded those feelings. I don’t think he consciously acted in spite of my request — Quite the opposite. I don’t think he was thinking at all.
After arguing about the matter the rest of the way to the subway, I decided I wasn’t going to engage him in conversation any longer. Clearly I wasn’t getting through to him. We rode the subway with a large group CK decided to befriend. I wanted nothing to do with them. When he asked me questions or tried to introduce me, I simply ignored him. If he wasn’t going to take my feelings into consideration any longer, I wasn’t going to regard his either. I began to wonder if this was something we’d ever get passed. Maybe we were just inherently different. Maybe he would never be able to see things through my eyes. I began to think about what it would mean to end things. Obviously that would be my last resort, but I began to prepare myself for that possibility.
I was also in a tough spot because I was spending the night at his place. By the time we resurfaced in midtown, CK finally realized I was ignoring him. He started to get irritated by this, and yet another fight broke out between us. This time, I didn’t care. I went nuts. I didn’t care who saw us fighting or what they heard as I laid into him. We argued back and forth about the severity of the incident at hand for some time. He didn’t realize it, but as each of these incidents came up, my tolerance for them dwindled more and more. Toward the end of the argument, I think CK finally got a clear idea of the zero tolerance I had left. I’m not the most bending person (and that’s an understatement), but this was one sticking point I wasn’t going to bend on. I didn’t care how small the infraction. He had a choice, and he needed to pick me.
He finally understood my stance and apologized for everything. He didn’t think this fell under my umbrella of discomfort. He finally understood that nothing in this realm would be acceptable to me. We were able to civilly walk the rest of the way back to his place, but the conversation was certainly nonexistent.
When we got back to his bedroom, I brushed my teeth, stripped down to my boxer briefs and climbed right into bed. CK finished what he needed to do before bed and climbed into the opposite side of the bed. That night, we didn’t go to bed fighting, but there wasn’t a lot of love in the bed either.
Birthday Sex
Posted by One Gay at a Time in Gay Dating on July 31, 2012
We did it. CK‘s friend and I pulled off a successful surprise (who from now on will be named Hip). Never before had CK been surprised on his birthday, and I was thrilled to be the first (with a lot of help) to do it. He had dinner with friends, dancing til close… What more could he want?
Of course you don’t think I forgot the most important part of the night. When CK and I got home, I was his for the taking. He had me for his every wish. After we said goodbye to the crew, we quickly walked home to truly celebrate the occasion. Hip was with us since he lives in Brooklyn. He was crashing on CK’s couch, but that wasn’t going to stop us from having fun. We said goodnight and closed his bedroom door — Time to get down and dirty.
I stripped down to my boxer briefs and removed CK’s clothes until he was before me in his briefs. I led CK to the bed by hand and pulled him down on top of me. His warm sweaty body felt amazing against my skin. Immediately, we began kissing each other all over our bodies. I could never quiet get enough of his soft supple lips. They brought me comfort like a cozy couch on a cold rainy day. Alas, my lips said goodbye to his as they made a journey across all the contours of his body. I explored every nook and crevice. Sometimes he would squirm because it tickled, and sometimes he would melt with pleasure. My lips found their way to the mountains retreat of his backside. This was one of my favorite places to linger, and oh did I linger.
The squirming continued, but this time, it wasn’t because it tickled. This time, it was pleasure overload. This continued for some time before we changed things up. Ck started his own exploration expedition with his lips on my body. I was laying on my back and his lips were tracing the insides of my thighs until I felt an incredible warming sensation. Every inch of me was in his mouth and he pushed deeper and deeper. Even though Hip was out on the couch, I couldn’t control my vocal expressions of pleasure. CK felt amazing.
From there, CK wanted to top, and who was I to deny him that. I immediately turned over onto my stomach, arched my back, and raised my hips into the air. I was never big on bottoming, but since I met CK, I was converted. No longer did I dread the act. With him, I found great pleasure. I was at ease and thrilled to know how much my man was enjoying my body. As he pushed deeper and deeper, I could feel his gently massaging my prostate. Gentle at first, until he began thrusting deep inside me. My moans grew uncontrollably, as did his. He was truly enjoying his birthday present. This was a man I loved deeply, and I wanted nothing more than for him to be happy. As his moans grew louder, I felt a warmth expanding deep inside me. There is something incredibly sexy and intimate about this act. Whenever this happened between us, I felt we were truly one. This was the man I wanted to spend the rest of my life with. Sure, I know that’s insane to say after a few short months, but I was hopelessly in love.
We adjusted and passed out in each other’s embrace. I felt so incredibly safe in his arms. My dreams were always much more vivid when I slept in CK’s arms.
The next morning, we woke up as Hip knocked on the door. CK was quite awake, but I was still groggy and couldn’t fully open my eyes. We chatted about how much fun the night before was. I was slowly waking up, and CK and I couldn’t keep our hands off each other, even with Hip sitting at the foot of the bed. His hands were quite active under the covers. Once he discovered my morning wood, there was no stopping him. “Baby! You’re so hard!” he exclaimed into my ear with great excitement. He was like a child with his toy.
When he left us to use the restroom, CK decided he wasn’t quite done having fun. He climbed on top of me straddling my legs and began gyrating back and forth. He slid to the side so he could get me wet with his mouth before returning to straddling me. It wasn’t long before he reached his hand back to raise me to a vertical position while he slid me inside him. It felt amazing. He continued to gyrate with me inside him and the comforter draped over his shoulders. I certainly wasn’t going to protest. It was a bit exciting and my slight exhibitionist side was awakened.
I did feel slightly awkward with Hip in the bathroom a few feet away, but then a big part of me didn’t care at all. I was very comfortable with Hip. I no longer considered him CK’s friend — He was my friend too. We grew even closer after throwing CK a surprise party.
When Hip emerged from the bathroom, even though CK stopped gyrating, he immediately knew what he was witnessing. It wasn’t a full minute before I pulled out and we laid next to each other again. I managed to reach down and find my boxer briefs on the floor to pull on while we all sat on the bed chatting.
Eventually, we all emerged from CK’s fortress of solitude. We were finally ready to face the day, even though it was a Saturday, and there wasn’t much day to face. From there we had no plans, and to me, that is a perfect Saturday with my man.
“I Love You”
Posted by One Gay at a Time in Gay Dating on June 27, 2012
No matter how many times it happened, I never grew tired of waking up next to CK. The night before concluded with the most passionate lovemaking we shared to date. Everything felt amazing!
It was late in the morning, but I was still reeling from our late-night romp. I could only dream every time would be like that from there on out. Warning: The following may be too graphic for some. When I woke him with my kisses, he ran his hand down my torso until he noticed my morning excitement. He grabbed hold and squeezed, expressing his delight in his discovery. He pulled the sheets down, followed shortly by my boxer briefs. As his head bobbed up and down between my legs, I let out moans of pleasure. What a way to wake up!
Apparently, neither of us got enough the night before. We were both still excited about how amazing it was. It made me excited and hard just thinking about it. We both wanted a sequel.
He climbed on top of me, and we began passionately kissing. Of course, things escalated from there. It wasn’t long before I had him on his back, and I was deep inside him. The sex was great that morning. It wasn’t quite like the epic romp we had the night before, but it was great. We flipped, and he had his way with me.
When we finished, while we laid in the bed together, he took hold of my head and said, “[O.G.A.A.T.], I love you.” Even though I suspected it was coming, nothing could have prepared me for that moment. No man had ever told me they loved me before. I knew he meant it. I stared deep into his eyes — Deep into the eyes of the man I loved too. “I love you too, Babe,” I added. We hugged strongly and kissed passionately. It was an incredible moment, and I began to cry a little. He reacted by comforting me. I think he was a little panicked. He didn’t know how to deal with that, but that didn’t really matter. We were in love. That was all that mattered.
Because of this and the sex, we were very late for our plans to meet P on the pier. When showered up, ate something and packed our bags for the pier. P was there waiting for us when we arrived. We apologized for being delayed and hinted at the reason. She gave a giddy laugh and scolded us.
P and CK decided to hit up one of the food trucks/ice cream trucks after a while. They came back with all sorts of things and an ice cream sandwich for me. While they were gone, I played with P’s dog, Baby, and I texted the rest of my friends to see who was up for a day on the pier. A few responded explaining they’d be on their way shortly.
I told the other two everyone’s whereabouts and plans. CK asked about my sister, but I told him she hadn’t responded to my text. He was very concerned with her perception of him. They’d only met for a short while at the Hoboken Arts and Music Festival a few weeks earlier. Even when prompted, she still had no opinion. This worried him.
After some time, my friend G joined us. I also got ahold of D and his girlfriend. They were in the city for brunch, but they would join us on their way back home.
CK and I decided we wanted to have some refreshing cocktails to go with our small picnic of snacks. Just as D and his girlfriend were arriving, we made our way to the liquor store to get some prosecco. I had a great idea to mix this with a few flavors from Rita’s Italian Ice.
While we walked, CK and I discussed him meeting my parents. They were coming into the city in early June for a Broadway show and dinner. I wanted him to meet them. I invited him to the dinner a few days earlier. I explained to him my sister’s reaction to his invitation, as well as my parents. My parents had no issue, but my sister thought it was too soon. In telling CK this, I realized I made a big mistake. He immediately expressed to me, “OKAY! Now, I’m definitely not coming!”
“WHAT!?” I protested. I was not happy with that. I was very excited for him to finally meet my parents. I’d met his mother, and it went swimmingly. On top of this, he meant a lot to me. I wanted my parents to know this. They’d never met any of the guys I’d dated in the past. In my protest and explanation, I think I was able to bring him back around.
We grabbed two bottles of prosecco and made our way to Ritas. We got watermelon and mango peach ice to mix with the prosecco. We planned to make refreshing summer drinks for all.
As we walked back to the pier, he still didn’t give up on the fact my sister wasn’t joining us. He was harassing me to invite her, but because of her snarky email telling me I shouldn’t invite my boyfriend to dinner, on top of other things, I was annoyed with her. Then I checked my phone when I went to invite her and realized I’d already done so when I reached out to the others. She didn’t respond. I told CK this, and his guilt was alleviated.
When we got back, we shared our drinks with everyone in improvised vessels since we forgot to get cups. Everyone was talking and having fun. CK was fitting in nicely. I loved seeing him with my friends and how he interacted with them. He passed my friend test swimmingly. I care a lot about them, and if he could’t hang with them, it wouldn’t last. He was able to hold his own and impressed me to no end.
When the sun was going down, everyone was ready to head home, including CK and I. We made our way back to my apartment, telling each other how much we loved each other along the way.
We decided to plant ourselves on the couch and watch Immortals for the evening. We ate dinner and cuddled on the couch until it was time to head back into the city to his place. We didn’t plan for him to stay over. It was very late, but he had nothing for work the next day. Since he was close to my office it only made sense to spend the night there.
We got to his apartment and got ready for bed immediately. I brushed my teeth and climbed in between the sheets. It wasn’t long before I dozed off, but I was thrilled to be in his arms. I never got tired of sleeping with him, and hopefully, there would be infinite nights in the future we spent the same way.
Follow @onegayatatimeFast Forward
Posted by One Gay at a Time in Gay Dating on June 6, 2012
Sunday morning, I woke to find myself sleeping next to a gorgeous man once again. How lucky was I – Two nights in-a-row spent in the arms of Clark Kent.
The night before, CK asked me to promise to get him up and on with his day at an am hour. I agreed. When I woke, I glanced at the clock. It was 9:00am. My alarm wasn’t set for another forty-five minutes. I rolled over and pulled CK into my tight embrace, cradling his entire body with mine. We fit together like intricate puzzle pieces. We became so entangled in each other, we jokingly called it forking. I didn’t fully wake him. He let out a tiny groan of pleasure when I pulled him in tight.
This, of course, wasn’t enough for me. I wanted more. No, not sex – Body contact. I began to remove his briefs, and he willingly aided my attempt. I followed suit and removed my own boxer briefs so our bodies would be pressed against each other skin-to-skin. I enjoyed his touch so much. He felt amazing. I fell asleep in this position until my alarm woke us at 9:45. He asked me what time it was, and I told him. His only response was, “Too early.” He grabbed my arm, rolled to his other side, and pulled my arm around him fully engulfing him.
He was such a sweetheart. We cuddled for quite some time. Periodically we’d switch positions when one of our arms would lose feeling. This was always accompanied with a myriad of kisses.
I hadn’t completely fallen for him. Why was this time different? There was nothing holding me back this time. Nothing, except myself. I was protecting myself. I didn’t bring my baggage with me on this trip, but I did bring my smarts. I knew it was too early to dive in with him. I wanted to build this the right way. If you rush the foundation, the building will collapse in due time. If you take the time to build a strong base, it can last a lifetime. I wanted to take my time. I was in no rush. Sure, I’m 28, but I still had a lot of my life in front of me to love, lose, and find love once again. I was proceeding with cautious optimism.
I think my caution goes back to our early interactions in which he propositioned me to come over for sex. I knew then and there I was dealing with a different kind of animal. Maybe he could be tamed. Maybe not. Only time would tell, but until I knew he could be tamed, I would protect myself.
The cuddling and kissing continued for some time. When my alarm rang again at 10:30, we were both a little more awake. Warning: The following may be too graphic for some. He began, as he did many times, orally pleasuring me. He loved worshiping me in that way. I certainly wasn’t about to complain. I also made sure to return the favor. I know I’m pretty good, but it wasn’t as easy for me – He was a definite challenge. He was well endowed, and at times more than I could handle. He would get a little overzealous with his hands and my head, and I would find the need to pause to ensure I didn’t suffocate.
We continued to play in bed until there was a natural pause in the action. I suggested we hit the shower. I attempted to find a way to toss him over my shoulder. I knew I could pick him up, but tossing him like a sack of potatoes was a different story. I failed. I told him I was holding up my end of the bargain to get him moving before noon. He protested and said, “Not yet. Just two more minutes,” and pulled me in to cuddle more.
Warning: The following may be too graphic for some. We started to kiss again. Finally, he said, “Shall we?” I replied, “We shall.” With that, I scooped him up and carried him to the bathroom. We hopped in the shower, and I took the bar of soap and washed his entire body. I used my own body to build up a lather as well until I found myself grinding on his backside and him bending over moaning in pleasure. Things never escalated from there to full penetration, but the didn’t need to. What we were doing was hot enough. He took the opportunity to wash me as well, and while he was crouching, he also took the opportunity to orally pleasure me. We then continued to rinse ourselves off before drying off and getting dressed for the day.
I had small plans for us that morning. I knew he’d be thrilled to take a ride on the bike. It was a gorgeous day outside, and I also knew a money saving breakfast would also be welcomed. I used all my eggs the day before, and the only real option I had left was cereal. I had a Living Social deal to use up at Sonic. What a perfect way to use it. It was a five-minute ride away, and it would be nearly free.
We hopped on the bike and off we went. We ordered our breakfast and sat. While we waited for the food to arrive, he asked if it was alright that he call his mother back. She’d been calling periodically over the weekend. They talked about his apartment search. He also mentioned me by name and told her how amazing I am, especially since I cook. I was shocked. He’d already been talking to his mother about me!? What else did he tell her about me? His mother put his nephew on the phone and they chatted for a minute. It was incredibly adorable. I was so turned on seeing his reaction to talking to his nephew.
When the food arrived, he hung up and ate. We shared our ice creams, feeding each other periodic spoonfuls. While we ate, he shared his tweeted comment on his Foursquare check-in with me: “Meal: cost-effective + tasty, but the company I keep: priceless + delicious.” He got a phone call from his friend who was just released from the hospital. After more than a few times of trying to end the conversation he was finally successful. His whole mood changed. When we finished eating, we stood, and he said, ”So I wanted to fully discuss what it was I said I wanted to chat with you about.” I was under the impression we’d already done that. Now, I was worried.
“I really enjoy spending all this time with you. You’re amazing. I really enjoy being with you. And, if I had to put a label on it, I’d say we’re dating. That being said, I think we should still be able to date other people. And, I should recognize you probably noticed I blocked you on Grindr, and that was by design. It’s a policy I have because if you try to call me, and I don’t pick up. Maybe you see me on Grindr and your mind will start to come up with scenarios.” At this point I acknowledged my awareness of this and told him how I felt about it. He continued, “I’ve done it, I’m sure other do too. And, I also should tell you, there’s a friend I’ve also been seeing since the beginning of the year. We see each other about once a month, go out to dinner, and then, well, we’ve done more than friends things.” I stood there not speaking through this whole thing. I just listened and nodded in my own confusion. “This is only going to work if we have communication and are honest with each other. I just wanted you to know,” he added.
I thanked him for his honesty, and he added, “Once again, please just be patient with me.” I assured him I was in no rush. Again, I had no idea where this was coming from.
He then pointed out how one of his loyal followers liked his comment on Twitter. He explained to me how he was kinda a hero on Twitter. He’d received comments from guys who found the confidence to change their lives based on some of the things he’s said. This was my moment. I told him I had a similar situation, and I had a secret I was waiting until the right time to tell him about it. I explained how I had a blog and received emails of a similar nature. I told him one day I’d share my alter ego with him, but it was like reading my diary, so not just yet. He seemed to be happy about the idea and accepting of my delayed full explanation.
I was still a little taken back by what he said. Part of me appreciated the honesty and part of me was confused by it all. Regardless, we hopped on the motorcycle, and I dropped him off at the PATH to head home. As I said goodbye, I told him to call me later to tell me how the search went. I didn’t think too much about what he said the rest of the day. There would be plenty of time for all that.
That night, as I was climbing into bed, I got a text from CK: “Are you awake?” Seconds after replying, the phone rang. He did call as he promised. I’d begun to think he’d forgotten. He really just called to say goodnight. He’d fallen asleep and napped most of the evening. He was tired and ready for bed as well. I told him, “Now I will be going to bed with a smile on my face.” He replied, “Aww, baby, that’s sweet! Me too. Sweet dreams!” With that, I laid my head on the pillow with a smile across my face.
Follow @onegayatatimeSticking to the Plan
Posted by One Gay at a Time in Gay Dating on May 4, 2012
I had a Friday to myself, and I wasted it on hookups. I could have been doing something productive like going to the gym or grocery shopping, but instead, I spent the day inside trying to line up sex.
There was one man in particular who I’d exchanged messages with on adam4adam.com. He was a well-built guy with a sexy body. He had a nice amount of body hair, great muscles and a spectacular behind. We’d talked about hooking up a few times, but we’d never seemed to line our schedules up. I messaged him, but he didn’t respond.
I continued to search for other guys on the computer when he finally responded. He didn’t read my message until it was too late. We exchanged phone numbers, and he called and told me he had a lot of errands to run before his mother’s birthday the following day. He wasn’t able to see me until later, but suggested we Skype in the meantime. I had nothing to do, so I agreed.
He was even good-looking with bed head on the computer. I couldn’t imagine how sexy he was in person. Seeing him on the computer was just making me hornier, if that’s even possible. I tried so hard to convince him to come by before his errands and do them later. All he needed to do was time-shift his day. He kept telling me the only way it would work is if I came to his apartment. I couldn’t because it was raining, and I don’t ride the motorcycle in the rain. We pushed back and forth for some time to no avail. Of course there was some teasing with body parts on camera while all this was going on. I couldn’t wait to feel his sexy body. Alas, he had to go, so I said goodbye and we made tentative plans for later. I told him when I came by, he’d certainly have to wear his jockstrap for me. He gave me a disclaimer. He was up for almost anything, but he was not up for full penetration the first time meeting me. I was a little disappointed, but understandable.
That’s when I turned to the Mexican guy in the previous post. He was willing to come by right then, and I needed a release. I had immediate regret after that encounter.
Later in the day, my old roommate texted and asked if I was interested in meeting up for happy hour. After being cooped up in my apartment all day, I thought that sounded like a spectacular idea. No one ever invites me out for drinks either. It’s usually me doing the inviting, so it was a special treat. I texted the burly man from my morning Skype session to tell him I’d have to postpone. He called immediately protesting. I told him other things came up, and I wouldn’t be able to come by. He didn’t stop persisting to try to persuade me otherwise. I told him he could have solved the whole thing had he come by earlier in the day.
The clock reached 6:00, and I hadn’t heard from my old roommate. I reached out to burly man to see if he was still available. Indeed he was. I agreed to come to his place a few miles from my apartment. He told me he would be waiting for me in bed wearing nothing but a jock and would leave the door unlocked for me to just walk in.
I drove over there and texted him when I got to his neighborhood. I tried the door, but it was locked. I called him to tell him, and he said his upstairs renter must have left and locked the door behind him. He told me to back away so he could unlock the door. I did as I was told and gave him a minute to get back to his bed.
Warning: The following may be too graphic for some. I came in, undressed down to my boxer briefs and began kissing his back while pressing my body against his. It was as great as I imagined. His a$$ looked incredible in that jockstrap! I could barely resist him. We had a lot of fun together. There was a lot of groping, heavy petting, kissing, sucking, licking, biting, rubbing, etc. It was great. I was really enjoying the jockstrap as well. I was grinding on his backside, almost penetrating him, but never fully entering him. He really enjoyed it and was pushing me further, but in the end, he stopped himself.
He was begging for me to finish, and he brought me to the edge many times. He started orally pleasuring me. He thoroughly enjoyed this, and it was turning me on since he was enjoying it so much. Eventually, I finished in his mouth and all over my abdomen, and he loved it. He began to use his hand to pleasure himself. I helped by applying pressure to different areas until he finished all over his abdomen. We’d chatted about how each of us shoots on Skype, and it was interesting how different and how similar we were. His description was pretty spot on for what actually happened.
We both just laid there a minute and enjoyed the feeling pulsing through our bodies. I still couldn’t get over how amazing his a$$ was. I wanted to penetrate him so bad, but I knew that would have to wait for another day. He hopped out of bed and handed me a towel to clean up. While I stood there, I met two of his cats. They were very cool. This guy was quite into animals. He had a huge saltwater fish tank as well. He ran to the restroom while I got dressed. I also took the opportunity to snap two pictures. He came back and got dressed as well.
He walked me outside and chatted a bit while he smoked a cigarette. He didn’t live in the best of neighborhoods. An old woman so strung out on something walked by, and he engaged her in conversation for quite some time before finally offering her one of his cigarettes and sending her on her way. He told me about how his mother lived next door and his family’s ties with the city. He was a really nice guy. I could see myself seeing this guy again some time. He told me he was also kinda seeing some guy, but it was very casual and nothing serious. He mentioned the desire to see me again sometime, but we didn’t set up anything concrete.
I sped off on the motorcycle back home to shower and get ready to go out and meet up with friends. The only friend interested in going out was P. We agreed to hit up one of my favorite local spots where I know the owner, and he takes good care of me, Cooper’s Union in Hoboken. We had a relaxing night drinking and sitting at the bar. I told her about how I was getting out of control, and it was then I decided I was going on a Grindr diet. This had gone on far too long. I was realistic enough to know I couldn’t quit it cold turkey, but I also knew it was a great temptation for me. I was going to try to steer clear. I would only go on to see if someone messaged me. I would no longer cast out a net and would no longer have it running on my phone all day. I needed a break. I was addicted, and it was time for me to ween myself off the drug…
Follow @onegayatatimeChelsea Comes to Hoboken
Posted by One Gay at a Time in Gay Dating on April 25, 2012
My Friday off was certainly an eventful one. I spent the better portion of the afternoon planning and participating in my first real threesome. I was already starting to judge myself and question all my recent behavior. A large part of me knew this was not who I was. I was completely acting out, but another part of me realized these were my gay “formidable years.” I never hooked up with guys in college while all my male friends were taking girls home from the bar. This was my wild time. Basically, I was giving myself license to have emotionless sex for sport.
That being said, I was still searching for the guy who would get me off Grindr and be the reason to settle down. I’d already gone on one good date with Chelsea. He asked what my plans were for the evening. I told him I had none since I had the day off, and he asked if we could do something together. I didn’t feel like doing anything crazy or going out, so I requested a lazy night in and suggested he come to my place. “Cuddle night?” he replied. “Definitely,” I said.
I still felt a little disgusted with myself for my afternoon behavior, but I also hoped maybe he could help distract me. He would certainly be something to get my mind off it. I took all my sheets off my bed and threw them in the washing machine. I hopped in the shower once again. I needed a cleanse.
I texted him back and told him I would make us dinner, and we could watch a movie. He agreed that sounded like a great idea, but he told me he’d already eaten. I made myself something quick before he came over.
“Do I have to come back to NYC late by myself?” he added. I told him he could certainly spend the night. In fact, I would very much enjoy that. He tried to convince me to come into the city, but I wasn’t about to budge. I’d already done one date in his neighborhood. I didn’t want to go into the city that evening since I wasn’t already there for work. He painted a better picture of what I was asking him to do: “Mind you, I don’t even go see my friends in Brooklyn. So this better be scoring me some hefty points! Haha! LMAO. You can ask my friends how much of a NYC snob I am. I’m like who? What? Why? Do I need a passport? And does Jet Blue fly there?” I quickly responded, “This isn’t my first rodeo. You’re not the first guy I’ve stolen out of the city.” Every guy I’ve convinced to come over to Hoboken has fallen in love with it and become an advocate. I am slowly introducing the NYC gay community to the great city of Hoboken one gay at a time :).
He agreed to stay over, as long as we agreed to behave. I told him I had no problem with that, and I appreciated him wanting to take things slow. I was very surprised by this, considering we met on Grindr, and I learned he’d done the hookup thing more than a handful of times.
When he arrived, I got him some comfortable clothes to wear, and we settled in on the couch with a few refreshments. We went through the guide trying to find a movie to watch. Finally, we settled on Drive, with Ryan Gosling. We laid on the couch with him in my arms the entire film. It was nice to snuggle with a man. It was very romantic. We both thoroughly enjoyed the movie, and when it was over, it was decently late. We decided to head to bed.
I found it adorable he didn’t take his shorts and shirt off when we went to bed. I don’t exactly sleep naked, but I have a hard time sleeping with clothes on. I find them restricting. I stripped down to my boxer briefs and encouraged (playfully removed the shorts I lent him) him to get comfortable before spooning with him a little. He warned me about getting too fresh, but I told him to relax. “I’m just trying to cuddle, not rape you. Stop fussing,” I jokingly stated. He did relax, and we got into a comfortable spooning position before finally dozing off for the night.
That night, neither of us slept very well. He was a thrasher and constantly woke up. I didn’t mind too much because I didn’t have anything to do the next day but lounge around. It was nice change to be sharing my bed with such a sweet guy. This had potential, and we certainly weren’t rushing things…
Follow @onegayatatimeOn A Sexual Roll
Posted by One Gay at a Time in Gay Dating on April 18, 2012
I have a generous amount of vacation days, as I did a very good job negotiating when I was hired at my job. I don’t, however, have friends who share the same luck. They can either take the time off and have no money to travel, or they have money, but can’t get away from work. On top of this, being single leaves me only with the option to travel – Alone. I don’t enjoy this. As a result, I build up all these vacation days and never use them.
When the new year arrives, I have until the end of March to use up all the days I carried over. As a result, I start giving myself four day work-weeks and have staycations. I decided to take Monday off after the local holiday in Hoboken. As per my usual, I woke up horny and turned to Grindr. I tried to get one guy I’d been flirting with to come to my place. He lived in the city in Harlem, so no matter how hard I tried, he was not going to come to Hoboken.
After him, I went through a ton of Grindr guys trying to find someone to come over for some morning fun. None were biting. I turned Grindr off after what I’m sure was over an hour of surfing, and hopped on the computer. I thought I would give adam4adam a shot. I had messaged a few guys, but I wasn’t getting a response. That was until I found one guy who is 26 and worked in the area.
He was a good-looking guy, as per his profile pictures. We began exchanging messages. He unlocked his pictures, and I got a glimpse of his face finally. He was a very sexy, light-skinned black man. He had this college jock look about him, and I was very turned on. His body was fit, he was clean-cut, and his smile was utterly adorable.
I asked him if he’d be free later to swing by. He had a light day at work since his boss was out of the office. We discussed logistics since he worked in neighboring Jersey City. He could either take a cab or the light rail to my place. I gave him all his options, and we made a plan for him to come by around 4:00. I learned he was usually a top, but he was willing to bottom for me. This was extra exciting to me, because I had greater hope he’d be a more masculine man than most typical bottoms.
When he arrived, I was immediately taken back by how sexy he was in his work clothes. Then I noticed his incredible blue eyes. He looked just like Michael Ealy. He was very masculine and had on slacks, a dress shirt, a tie and an incredible smile. He wasn’t nervous about this at all, which I found to be very sexy. I led him into my room, and he immediately began undressing himself. I liked his matter-of-factness — His “I know the drill” style. I sat on the bed talking to him as he undid his tie, stripped off his shirt, removed his shoes and took off his pants.
Warning: The following may be too graphic for some. The man had an amazing body. I was very pleased. I could tell he takes good care of his body, and I was ready to ravage it. I wanted to touch every inch of his milk chocolate colored skin. I was still sitting on the bed in my gym shorts and tank top when he unexpectedly took off his boxer briefs as well. If I wasn’t already excited before, now I was rock hard. He walked toward me as I stood and removed my clothes as well.
He was a well gifted man, and once we were both fully undressed, we laid on the bed with him on top of me making out for a bit. He had amazing lips and knew how to use them. He had a strong body, and I enjoyed wrapping my arms around him. It was hot! We began to fool around and explore each other’s bodies.
Ater some making out and mutual oral pleasure, he got into position for me to use some of the techniques I’d read in Tickle My Tush. I knew he was normally a top, so I took the time to make sure he was fully ready and not rush things. I was enjoying myself as well. He seemed to be really enjoying himself as well from the sound of things.
That’s when I reached over the edge of the bed to my nightstand and grabbed a condom and some lube. He was face down on the bed in front of me, and the real fun was about to begin. I really enjoyed being up against his body and feeling him. He may not have been a bottom, but he sure was passionate in the bedroom and knew how to use his body. The sex was great, and eventually he finished. Seconds after that I too pulled back and finished. It was very hot! I grabbed a towel to clean up his back and the sheets below while we exchanged a few more kisses and expressed our enjoyment with each other.
Just as he undressed like he knew the drill, he began to get dressed. I learned he was heading back to work. I was surprised because he lived in the city. I assumed I was a pit stop on the way home. I felt bad for him he had to return to the office, but I didn’t regret inviting him over. I had a great time with him and would certainly be willing to have him swing by again sometime.
I walked him to the door and gave him another kiss goodbye. He was such a polite gentleman. I could tell him momma did a good job raising him. He thanked me, to which I replied, “Thank me!? Thank you! That was great! Anytime you want to do this again, you know how to reach me.” And with that, he was gone.
In the coming weeks, we’d try to do it again, but he was having a busy week. I could tell he was more than just a hot body, so after that, I asked him if he’d ever be interested in grabbing a drink sometime, but I got no response. Perhaps he will just remain a fond memory of a day off…
Follow @onegayatatimeHalf Day Fun
Posted by One Gay at a Time in Gay Dating on April 12, 2012
Monday at work, I received a email from UPS notifying me a delivery attempt was made. When I arrived home Monday night, I had a notice on my door from UPS. They’d been there earlier in the day and attempted to deliver the leather chair I ordered. No one was home, but luckily the driver gave me his cellphone number so I could call him when I got home. I called him, and he delivered my chair around 7:30 at night. (I love my UPS man!)
I’d already informed work I’d be taking a half-day to accept the chair, so I kept those plans. It would allow me to take care of a few things after my emotional trip to LA.
Since I didn’t have to get up early Tuesday morning for work, I decided to reach out to a guy I’d been chatting with for quite some time on Grindr. I was very apprehensive because he was so young. He is 22 and is still in college. I told him straight up my hang-up with his age. That being said, I still agreed to meet him, but I explained it wasn’t an ideal situation.
When we first talked on Grindr, he was looking mainly for a hookup. He had an amazing body, but I was making an effort to calm down with the hookups. I told him I was looking for something more substantial. He was very interested in this response, but he already showed his cards. I knew he was there more for sex. We agreed to meet up for a drink sometime, and I went to bed.
Tuesday morning, I let my hormones get the better of me. I woke up horny as usual, and I found him on Grindr once again. I asked him if he wanted to come over. The conversation quickly morphed into sexual territory.
We both talked about a few fantasies, and I quickly learned he had an adventurous side. I was very turned on, so I told him to come over. He explained he needed to shower but would be up for coming over. I too showered in anticipation of his arrival.
While we talked about our fantasies, we discussed a little fun when he arrived. I told him how hot it would be if he undressed in the hallway before entering my apartment while I watched through the peek hole. He was more than enthusiastic about this and agreed.
When he arrived at my apartment, I buzzed him in. He came to the door and did exactly as we discussed. I was so incredibly turned on watching from the other side of the door. When he was left in his boxer briefs, he knocked. I let him in and led him to my room. We chatted very short bit before we started making out. He stripped me down to my boxers as well, and we embraced each other while we made out on the bed.
He had a great body — Plenty of muscles and lots of definition. He had the cutest smile as well! Warning: The following may be too graphic for some. This escalated, and the boxers ended up on the floor. I couldn’t keep my hands off him. He was the best looking guy I’d been with in a long time. He was also one of the best kissers I’d been with since I can remember.
Before he came over, we chatted about positions. He told me he usually was a top, but he wanted to bottom for me. He told me he had little experience in the area, but wanted to try it out with me. As things escalated, I whispered in his ear my desires and asked him if I should get a condom and lube. He enthusiastically said yes.
I made sure to take things VERY slow. I was treating him as if he was a virgin — Not my first. It took a little time, but after a short bit, he was very much enjoying himself. I could see waves of goose bumps flowing over his body. It was incredibly sexy. I’d finally found a match for passion in the bedroom. He had the right mix of intimacy and sex, and I was thoroughly enjoying myself.
It became necessary to take a break so he could catch his breath. We talked while he relaxed, mixed in with some more passionate kissing. After some time, we made our way to the edge of the bed and tried a new position, which we both thoroughly enjoyed. It’d been a long time since I was with a man in which I felt our bodies become truly one.
When he had his fill and couldn’t take anymore, we laid next to each other and pleasured ourselves. For once, it didn’t take me too long before I finished. He made a comment about being impressed, but was unable to finish himself. I immediately pegged him as someone who had the same problem I did.
We laid there for some time cuddling. I took a lot of time to take in his smile. It lit up his entire face. He was very cute. He is of a Middle-Eastern decent, which I would never say is my type, but I was really attracted to him.
This guy was one of the few who would be a repeat offender. He too expressed his desire to see each other again as we both got dressed. I was still incredibly turned on watching him stand naked in my room while he put on his clothes. I wasn’t just attracted to him sexually. I could tell he was a special guy. I was attracted to him on an emotional level as well. I just worried about our compatibility. I’ve been out in the workforce for nearly six years now. He still hadn’t even graduated college. I’m not one to discriminate based on age, but I do discriminate on life stage. This would either be a guy who expanded my horizon, or proved my rationale — Only time would tell…
Follow @onegayatatimeLate Night Quickie
Posted by One Gay at a Time in Gay Dating on April 11, 2012
Sunday night in LA, I took quite a blow to my heart. I tried to prepare myself for the inevitable goodbye, but I didn’t get to say goodbye. I’d driven all over LA trying to connect with The Navigator, but he wasn’t responding.
I faced facts and drove to the airport. I had no idea what else to do with my time, so I just drove to the car rental lot and returned my car. I figured I could at least use some time at the airport to blog a bit. I sat int he airport diner and ate my dinner alone.
My flight home was awful. First off, it was a redeye. I was set to land at 6:00am Monday morning. I had to go to work later that day so I tried my best to sleep on the plane. It was also awful because I was crammed in a widow seat towards the back of the plane. My airline status with United got me nowhere. I barely fit in my seat, and I wasn’t able to stretch out and walk around because the two men next to me were sleeping the entire flight.
I managed to sleep for two hours, but woke up after that. I had no feeling in my ring and pinky finger of my left had. Apparently I slept on it funny. When a fair amount of time passed, and I never regained feeling, I became worried. Maybe I had a blood clot or maybe I’d done some nerve damage. I tried to think about other things and distract myself, but I really started to get worried. I took out my laptop and did some more blogging, but even that was a challenge with two numb fingers. I was really starting to worry, but the feeling didn’t return the rest of the flight. (Four weeks and a doctor appointment later, and I finally regained feeling — I had a nerve impingement — Cubital Tunnel Syndrome).
I was exhausted all day at work Monday. I’d only gotten a few hours sleep on the plane and about one hour in my own bed before work. When I got home after work, I was still horny from my rambunctious trip. I was on Grindr, and a cute guy from the city wanted to come over for some fun. I didn’t turn him down since he was hot and said he’d wear his jockstrap.
When he arrived, I realized he was a redhead. He also had a slight Hispanic accent. He was also quite a presence clocking in at 6’4″. He was not born in America, but had been here a majority of his life. He was decent on the eyes, but nothing you’d run to your friends about. When he arrived we went straight to my room. He slowly got undressed and comfortable until we were both laying on the bed, me in my boxer briefs and him in a jockstrap.
Warning: The following may be too graphic for some. I found the jockstrap very sexy. I’ve always been attracted to the athlete types and find locker rooms to be one of the sexiest places. They just turn me on. Always have.The jockstrap really gave him the leg up in my book. He was looking for a hot top, and I agreed to fill the position, literally. I broke out the condoms and lube, and we have a good time. Sometimes it was a little weird and awkward, but sex is never perfect! He really seemed to be enjoying himself. I did as well, but I could already tell this guy was going to linger. He was a gentle spirit. This would be no wham bam thank you man. I was going to have to sit through some pillow talk.
He started talking about his grandmother and how she is sick. He was flying home the following day to see her before she passed away. It wasn’t looking good. I started to feel bad for him, but then my emotions became distracted when he mentioned things like sleeping with her in her hospital bed. He looked like he was ready to cry, but all I could think about was this strange layout in a hospital room. I understood he was close to her, as she was responsible for raising him, but some of the things he was saying with his accent seemed very strange to me. There was obviously a cultural divide.
After we chatted some more, and he asked if he could use my shower. Now he was really pushing it! I obliged the request, but after that, he was gone.
He showered and toweled off. He began to get ready to go home. He talked about getting together again when he got back. He mentioned how heartless a lot of the other guys he’d hung out with were, and how sweet I was. He said how much he liked me. He wanted this to be an ongoing thing of friends with benefits. He told me his real name and that the name he gave me, Keith, was completely made up. Someone was a little paranoid. I felt like I found a stray puppy who wanted to follow me home. There would never be a next time, but I told him to hit me up when he got back from visiting his grandmother. After about three weeks, he did of course text, and I of course did not respond.
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 
Check That Off the List
Posted by One Gay at a Time in Gay Dating on April 24, 2012
Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.
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.
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!
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.
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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