Posts Tagged briefs

Surprise Ending

When I got home from my dinner date with Smiles, I sent him a text asking if I could spend the following night with him at his place. I wasn’t sure if he’d already passed out, but I never got a response. I was hoping he’d answer me before I left for work in the morning so I knew if I should bring clothes for work the next day.

My office party was that Wednesday night at the Greenwich Village Country Club. We weren’t able to bring guests, but I was hoping I could see Smiles following the party. I wasn’t all that into it and was willing to leave early if need be.

Wednesday morning arrived, and I still had no answer. I decided to be on the safe side and bring clothes regardless. Maybe he’d answer me midday. When I didn’t get an answer, I asked the question again in a text.

He responded with an apology. He didn’t realize he didn’t respond the night before. “Yes. You can spend the night.” I explained the party, and he told me he had happy hour plans with his wealthy client friend and his partner.

For me, the office party was not all fun. Every year I get wrangled in to help with a few elements of the night. I performed my duties and then had fun drinking and dancing with my coworkers. It was a really good time — Better than I expected. However, I was more looking forward to seeing Smiles.

I texted him to see what he was up to. If he was still out, I was going to meet up with him. He told me he was wrapping up drinks and heading home shortly. I told him I would be leaving the party shortly as well and would come by.

I said my goodbyes and collected my coat. I wasn’t that far from his apartment, so I decided to walk. While I walked, I called his phone just to make sure he was home. I called about 10 times in a row with no answer. I sent text messages and heard nothing back as well. I wasn’t sure what to do, but I decided to continue on to his place. Finally, just as I was nearing his block, he picked up. His phone was on silent in the other room, but he was home.

He buzzed me in, and I came upstairs. I gave him a big kiss hello. I wasn’t drunk, but I was properly tipsy.

We talked about happy hour and the party while we hopped into bed. I undressed and hopped on “my side” of the bed, and he slid into his side.

Just recently, I made the switch back to briefs periodically. I decided I looked good in them since they showed off my legs — The same legs Smiles loved to compliment. So I knew what I was doing when I laid on my back in just briefs while talking to him. We chatted a bit before he made a big move. My seduction worked.

Warning: The following may be too graphic for some… As I laid on my back in my briefs, he started groping my crotch as he rolled over partially on top of me to make out. This was a bit out of character for Smiles, but I like it. Apparently he liked what he saw and went for it. I could get used to that.

Things got more heated and passionate and the clothes came off. I thought this was going to be the extent of our romp in the sheets, but apparently he was ready to escalate things. He proposed sex. I was a little apprehensive because he was still recovering from surgery. I didn’t want to further injure him. He detailed his limitations; he couldn’t top and he couldn’t put his legs up. I was still worried I may hurt him, but if he was good for it, I was game.

With that, he put a condom on me, and he climbed on top. It didn’t take long before I lost it. I’d been drinking the better portion of the night, and that really wasn’t helping at the moment. “I always lose you in this position,” he said. I found that ironic, because that was the position Broadway and I so often found ourselves in.

“Have you ever done poppers? he asked. I told him I’d never done them myself, but I’d witnessed them used. He told me it increased blood-flow and would produce one of two effects. Either it would make the problem worse or it would solve it. I figured it was worth a shot, so I agreed to partake.

He opened his nightstand drawer and pulled out a small vial. He held it up to my nose as I inhaled. Sadly, it had a negative effect.

“Let’s try one more thing. Stand up. It may help the circulation,” he told me. So I did what I was told. Magically, it worked. He turned, and I pressed my chest against his back. He lubed me up and bent over the bed, and we went at it. Finally, we were having great sex, even if it did get off to a rocky start. Apparently, he also was enjoying it as he finished on the floor. Just as he did, he turned around and said, “I wish I could make you cum.”

And it was over… I was close to finishing, but him pointing that out to me made me lose it immediately. My mind switched over immediately.

He walked to the shower, and I laid in the bed. I wanted to hop in the shower, but that wasn’t physically possible based on his setup. I thought we could have more fun and maybe I would finish. When he came back, I took off his towel and pulled him into the bed. I told him not to say things like that because it was a sure fire way to make sure I didn’t finish with him.

We cuddled for a bit, just laying in each others’ arms. Just as he was about to get up to go brush his teeth, I asked him if I could ask another question. I wanted to ask him where we stood. I wanted to know what I was to him. However, as he walked away, he responded, “No.”

I was a little crushed. I went from being so happy to finally be having great sex to utter disappointment. How was I supposed to be in a relationship with him if I couldn’t express how I was feeling.

He came back, and I was already prepped for bed. I curled up facing the wall ready for sleep. I wanted him to read my body language and realize how much I closed off, but I don’t know if he got the hint.

That night I had a dream about Smiles. I specifically remember him in the dream saying to me, “You know I like you, right?” It was the reassurance I wanted in reality, but this was a figment of my imagination. It was just that – A dream.

For the rest of the night, I didn’t sleep well. I tossed and turned like the inner turmoil I so wanted to release.

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Sexy Eyes

After seeing Sexy Eyes on the street with my roommate, I decided to make him a priority. He not only impressed me, but also my roommate. She wanted to date him . He was charming and funny and had a smile and sexy green eyes that gave me butterflies.

On my way home that night, I began texting immediately. He was all but begging me to stay in the city that night with him, but I insisted I would not let my roommate walk home alone at that hour of the night. He heavily respected my decision, but also attempted to persuade me to come back on another bus after I walked her home.

Instead, I promised we would go out the following Friday. That still didn’t satiate him. He wanted to know why we couldn’t meet Thursday. I explained I had my volleyball league Thursday nights, so I would be unable to meet up. I figured he would understand being quite the volleyball player himself.

That of course was a lie. I scheduled a meeting with a guy from OKCupid. It was an interesting scenario. The guy reached out to me originally, but after chatting a bit, I came to learn he was seeing someone. He was just looking for friends. I didn’t buy it of course, but if that’s what he really wanted, I was game. I need gay friends. We scheduled happy hour drinks for Thursday evening after work.

On top of that, I scheduled another date with a guy I met on Grindr a week prior. Between these two, there would be no time to meet Sexy Eyes.

When the OKCupid friend had to bail because of a follow-up job interview, I decided to see if Sexy Eyes was available for after work coffee. I figured we could sit and chat and get to know each other a little better.

He bit. He was extremely excited to see me. Immediately following work, I walked down to the Starbucks closest to his office. He works at a financial law firm and would not be finished for the evening. He was, however, able to step out for about an hour to chat.

The conversation was mainly dominated by him, but it was good nonetheless. We talked for about an hour before I told him I needed to head home for volleyball (my other date). Our date ended with a few smooches and a hug. I was really feeling this guy. We shared a lot in common, he was older and had a respectable job, he was very good looking, he was fun to be around… The list goes on. As I walked away, he texted me telling me he wanted to kiss me more, but didn’t want to make a scene near his office. He begged me to come back into the city after my “volleyball game.” I entertained the idea in my head, but I made no promises. Who knew how my next date would go?

I met the next guy at a bar near the Christopher Street PATH station, but that will have to be tomorrow’s blog entry, because as you may have suspected, I wasn’t quite done seeing Sexy Eyes that evening. After my second date, I went home, showered and changed, and hopped on a bus back to the city. Sexy Eyes was just finishing up his own volleyball workout as I was getting to Port Authority.

We agreed we’d go out somewhere, but made no plans. When I arrived at Port Authority, I called him to find out the plan. He told me he just got out of the shower and needed to finish getting ready. He gave me his address and told me to come to his apartment. We would make a decision where to go from there.

When I arrived, I told the doorman who I was there to see, and he let me up to the apartment. I was greeted at the door with a very nice kiss, and we chatted while he finished getting ready.

Somehow, we both ended up in his bedroom just as he finished getting ready. He sat on the bed in front of me, lifted my shirt and began kissing and licking my entire torso. It felt amazing.

Between kisses, he asked if I wanted to go out or just stay in. I didn’t need to verbally answer because I was already removing his shirt. I hadn’t had sex since Labor Day. I won’t say I was a big ball of horny, but he was a very attractive and seemed very interested in me and not just my body. I wanted him. Bad.

(Warning: The following may be graphic for some) Shortly after, he was undoing my belt and unzipping my pants. He was thrilled to learn I submitted to his request to wear briefs. I never wear them, but if a man requests it and thinks I look sexy in them, who am I to disagree? He then pulled down my briefs and opened his mouth and felt amazing. It had been a while since anyone did anything with my body besides my own two hands, so I was completely enjoying the moment.

Things got hotter, and we both ended up on the bed in numerous positions. Throughout the course of our time in bed, he started playfully biting me. I’m not gonna lie. It hurt! I went along with it because they were quick, and I have a high pain threshold. But, I wasn’t entirely into it. This was something that may have to be resolved down the road. At the peak of the passion, I was inside him, and we were both thoroughly enjoying ourselves. He finished during the act, and shortly after, I finished myself off. As per usual with the guys I’ve been with, he was impressed with my finale. Something I’ve learned to take pride in based on the reception it usually gets.

He beckoned me to come join him in the shower to clean up so we could snuggle in bed. After the shower, we laid in bed together and watched the late night news. It was getting very late, and I was constantly dozing off. After realizing this, he suggested we turn off the TV and go to bed. After all, we both had work in the morning, and he had to be up earlier than I did.

The next morning, we woke at the same time. He hopped in the shower while I read over emails from his bed. When he got out, I hopped in for my turn. He told me he would probably be gone by the time I got out. I was instructed to take my time and just pull the door shut behind me on my way out. I thanked him and kissed him goodbye.

That evening, it was affirmed for me the biting had gone too far. All day at work, my chest was sore where he bit me, and when I came home and got undressed, I looked like I was abused in certain spots.

That morning, I walked to work with a smile on my face. It was a good night, and I met a good man who seemed to be interested in me. Over the few months I’ve been out and single, I’ve learned my lesson not to count my chickens before they’ve hatched. Maybe I’ve become slightly jaded in the process, and this bothered me. But, this was something I needed to start doing so I wouldn’t get my hopes up and get hurt in the end.

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