Posts Tagged awkwardness

Meeting the Hatfields

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…

Southern Drawl was very anxious to see me. Before our last date ended, he asked me, “So, when do you get to see me again?” It was a bit egotistical, but it was also a little cute.

I had plans with other guys for the rest of the week with the exception of my volleyball game on Thursday. We agreed to do happy hour after work on Friday to get the weekend started off right. He was going to the Frying Pan, a permanently parked barge on the Hudson River that doubles as a restaurant/outdoor bar, with a group of his coworkers. Apparently, he was comfortable enough to introduce me to them.

He was already there when I made my way across town to meet him. He worked right across the street, so there was a solid crowd present from work. I found them in the crowd and pulled up a chair to the table. Everyone was very welcoming and nice. They immediately offered me a cup of sangria, and I settled in. I joined the big conversation, and Southern Drawl and I had a few side conversations not meant for the table.

I wasn’t sure to what extent he was out to his coworkers, so I played a vague roll. I didn’t show any signs of affection or do anything that would be a severe tell. I had a good time.

When everyone was ready to go, we started walking. We were heading to his apartment, but we walked with the others until they peeled off to head in separate directions. It was then I was informed that this was a big deal. None of the other guys he dated had met his coworkers. Only one or two of them knew he was gay, so this was somewhat of a public coming out. I’m sure his coworkers would put two and two together if he was inviting a man to join them for drinks. It was flattering he was willing to do that with me.

Since before I met S.D. in person, I’d learned of his incredibly flamboyant and promiscuous roommate. We talked about him to quite an extent on the walk.

I could not have been prepared for his apartment when I walked in there. It was an utter dump! His roommate was lounging on the couch when we arrived. S.D. needed to change before we went out for the rest of the evening. I chatted a bit with his roommate, and he certainly had a strong unwarranted air of superiority. We didn’t get along, but we didn’t clash either. He was a non-entity to me.

Meanwhile, I made a comment about S.D.’s shoes, and I was ripped a new one. He went off on me how expensive they were and how dare I downplay them. I was dying to get out of that apartment, and S.D. was dragging his feet.

He told me his friends from back home in the south were going to be out on the Lower East Side since one of them worked at Brother Jimmy’s. We decided to pick a place in the neighborhood to grab dinner before drinking our faces off. We found a nice Italian restaurant, Pete’s Tavern and shared a delicious pleasant meal. Things were starting to feel comfortable with him. All the awkwardness melted away. We had great conversation and kept each other on our toes. The conversation was great, but I began to wonder if I was sexually attracted to him. When he sent pictures to me, I found him to be quite attractive, but since being with him, I didn’t get excited or aroused by him. We hadn’t crossed that bridge yet, but I wondered if when I came to that bridge, would I even want to cross it. On top of that, we hadn’t discussed positions since we first spoke on the phone. He told me he didn’t have much experience in the bedroom originally. He said he never really bottomed, but he may be willing to experience it. Since then, I got a different picture learning about the long-term relationships he’d been in. I wondered if they were sexless, or was he lying. We were two tops, and that was going to pose a problem as some point.

After we finished dinner, we walked to Brother Jimmy’s to meet his friends. He was excited to introduce me to them. They’d already seen pictures of me and predicted I was a far better man for him to date than the one he just let go. They already loved me before even meeting them, so it was my game to lose.

S.D. introduced me to them, and we hit it off pretty swimmingly. His best friend, a female, pulled me aside to talk and gossip. We chatted, and she expressed how much she liked me. “You’re just the right amount of gay,” I was told. I’d always thought that about myself, but it was still interesting hearing someone say this to me. Even the friend, the girl who was working behind the bar planted a kiss on me, right on the lips. It was a pleasant surprise. I was a hit!

S.D. also told me his friend from work, “his little buddy,” was joining us. This kid was gay and even lived with S.D. on the couch for a period. They were very close and best friends of sorts. When this kid arrived, I was introduced to him. He seemed very nice, and we exchanged small talk. Almost immediately, S.D. and he separated from the group and began chatting the night away. It was obvious to me S.D. had a crush on him. I wondered if the little guy just wasn’t interested in S.D. and that was the hangup for why they weren’t together. I felt incredibly neglected. I was getting quite drunk, and that usually peaks my emotional state. I was very close to walking out the door and going home without a word but better judgment kicked in.

After we watched someone who looked like Snookie do an amazing rendition of Adele for karaoke, I was ready to go home. I was drunk, and I was trying to see past how he ignored me. Even after all I drank, the bartender charged me seven dollars.  I’m still not 100% sure why, but I asked S.D. if he wanted to come back to my place and spend the night. I think I wanted to test our sexual chemistry. I wasn’t looking for sex. Clearly that wasn’t possible in the state I was in. I just wanted to get somewhat physical with him.

We made out way back to my place and quietly made our way to my room. We climbed into bed to spoon, and I passed out quickly.

Warning: The following may be too graphic for some. When we woke up in the morning, we started spooning and fooling around. There was a lot of heavy petting and oral pleasuring. It wasn’t long before he was straddling my chest fondling himself. It also wasn’t long before he excited himself so much he finished right on my chest. He asked for my permission, but I wasn’t expecting it to happen almost immediately.

We lounged in bed for some time before I made us breakfast. There was a bit of a schedule for the morning, however. My parents were coming into town for Easter weekend. I needed to get him out of there before they arrived. Just as we finished eating, I got a call from my parents. They were downstairs. I told S.D. to quickly get dressed and make his way down the back stairwell. He was fine with this, and we agreed we’d chat later on the phone. I hustled him out the door and kissed him goodbye.

One minute later, I threw on flip-flops and went down to greet my parents. They didn’t make a single comment about the guy leaving my building. I had yet another celibate weekend in front of me, and this was a good thing.

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

Leave a comment

Lazy Morning

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…

 

Smiles and I had a very special night together sharing dinner in my apartment. We went to be happily in each other’s arms after being away from each other for some time. I’m not entirely sure why, but I felt he’d finally come around to me.

The next morning, we woke up late. I knew I had a very light workload that day, so I was in no rush to wake up. I was also feeling frisky. I tried to seduce Smiles with a back rub. I instructed him to roll on his stomach as I lifted his shirt and began massaging his back. He commented on how my hands can completely cover his back from end to end. This was one thing my big hands specialized in, so I was content putting them to good use. I began to reach my hands under him grasping his pecs in a sensual manner.

The massage didn’t last long and the seduction failed to the grumbles of Smiles’ stomach. I should have remembered that was his first priority in the morning.

We went into the kitchen and brewed coffee while I made us steak and eggs (some of the left over beef from the night before). He continuously hugged my while I cooked. Cooking at the stove for a sexy man while he wrapped his arms around me — What more could I want?

We sat at the kitchen counter and ate while we chatted a bit about what we had to do the rest of the day. I also caught Smiles up on some of the events going on around the world since he didn’t have cable and wasn’t the best at staying informed.

After breakfast, we returned to my room. I needed to get ready for the office, and Smiles needed to get dressed to head home to begin his workday. We started to make out a bit until I pulled him towards the bed. “Do you want to have sex?” he asked. I giggled with a big grin and replied, “Of course. Why do you think I was trying to seduce you before? I always want sex.” That was also my subtle way of letting him know I wanted to have more sex.

During the summer of 2010, after my breakup with N, I was having a lot more sex. I decided to be more economical with my condom purchases and bought a forty pack. I kept them in my nightstand drawer next to the bottle of lube I purchased. Smiles had been in the drawer before, and I’m sure he’d noticed the quantity. But, he never said anything about it until now. He made a comment on how many I had. “Does it intimidate you?” I asked. He simply replied with a “No.” I then gave a not so subtle comment hinting about how I’d like to have more sex. “Well, we could just use them all, and then there won’t be so many,” I exclaimed. Apparently, our conversation about the state of our relationship gave me the confidence to speak my mind when it came to our relationship going forward.

Warning: The following may be too graphic for some. I was already on my back with him on top of me, so I could only assume he wanted to top this time around. I topped the last time, so I only thought it fair to receive this time. I slipped the condom on him as he made a comment questioning whether I was doing it right. “[Smiles]. This isn’t my first condom, obviously,” I quipped.

I lubricated myself and laid back. I hadn’t thought much about my inability to finish with Smiles in quite some time, but I was going to try a new technique this time around. I was going to completely relax and try to enjoy every minute of it. I usually derive no pleasure from bottoming, but for some reason, this time it was working. He felt great, and I could tell he was enjoying himself as well.

I was getting very close as I pleasured myself while he penetrated me. Just as I was about to climax, he said, “I going to cum.” I quickly responded, “Me too.” And with that, as close as I was, I was a mile away from finishing. In that split second of him distracting me, I lost it. I could feel my muscles quivering just before he said anything, but it was gone. Now, it was top of mind, and I knew it wasn’t going to happen.

Smiles would have been so happy. He’d wanted to make me finish for so long, and he would have been the first to do so from topping me. Alas, it wasn’t meant to be. When it didn’t, I could see him looking into my eyes with compassion. The sex was great. There was no pain or awkwardness. I wanted to show him how much I enjoyed it, but I couldn’t. My mental block got in the way once again.

After we relaxed and kissed a bit, he suggested we clean up in the shower. He was getting ready to hop in, and I told him I was coming in with him. My shower has two shower heads and a seat. Everyone that has seen my shower has made sexual comments about it, and I was going to finally get some use out of them.

I wanted to have some more sensual time together, and when I hopped in, Smiles began to wash me. I was very turned on by this. When he finished, I tried to do the same for him, but he wasn’t interested. He rinsed off and hopped out of the shower to dry off. I watched him as he toweled off, and immediately got extremely aroused. He put lotion on his face with his towel on the floor while I pleasured myself in the shower at the sight. When he left my bathroom, I beckoned him to come back in the shower and help me finish. I wanted him to be a part of it. He climbed in and I pressed myself against his back while I tried to finish. Once again, failure.

When we ran out of hot water, we hopped out. He finished applying lotion and brushing his teeth while I masturbated on my bed. I needed to finish somehow or work was going to be hell for me! He came and joined me in the crook of one my arms while I pleasured myself. FINALLY, it came. I thought of him dropping the towel in the bathroom, and it set me off. I was disappointed it wasn’t a direct reaction to something Smiles did, but I was relieved he was there to witness that it was possible and that my climax was something pretty special 😉 .

We quickly finished getting ready and walked to the PATH with my roommate chatting the whole way. The conversation wasn’t as free-flowing between us as much as when it was just the two of us. I wondered if Smiles had issues with PDA and public discussion. It just felt a little awkward.

When we got to his stop, I gave him a peck on the lips to say goodbye. I thought about that morning all day. I was happy to finally finish with him in the room, but I wished it came at Smiles’ hand. I think it would have been an ego boost for him and a big step forward for the two of us. However, it was progress — Baby steps. This something I was going to conquer, hopefully with Smiles’ assistance.

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

8 Comments