Posts Tagged happy hour
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!
Never before have I prefaced an entry by giving away some of the details of what’s to follow, however, I’ve received numerous comments from readers tired of reading my “sex journal.”
“Your blog used to be interesting when it was about your relationship with your ex bfs, but it turned me off when it became a sex journal,” wrote one reader.
We’re both on the same page here. I dislike writing about these trysts as much as you dislike reading about them. It’s bad enough I’ve lived them once, let alone having to live them all over again when I write them.
So, without further ado, I am pleased to present you a love story…
On a Wednesday morning in April, while on my way to work, I happened to poke around on Grindr a bit. There was a message from an interesting guy on there. We began to chat a bit while I walked. He seemed pretty cool. I was about to head underground, so I quickly asked him for his phone number so we could continue the conversation on the other side.
We chatted a bit over text, and I came to learn a few things about him. I explained to him I wasn’t looking for sex, so if this was his motive, he should move on now. I was there purely for dates and friends. He seemed okay with that sentiment, and the conversation continued for a bit. I tried to check his spontaneity and asked if he would be interested in drinks that evening. He couldn’t because he had to work late. That’s when I learned he worked in advertising. I explained to him, if anyone understood working late for a pitch, it was I. I explained I too worked in advertising. When he told me he worked downtown, I started guessing what agency. Ironically enough, he worked for my previous agency. He worked closely with one of my favorite ex-coworkers. We were really hitting it off and I was excited to meet him. We agreed to make plans in the near future.
Wednesday evening, I was on my way home from a mediocre date. I fired up Grindr on the bus ride home and noticed he was on. I messaged him to say hi. He and asked what I was up to. When I told him I was on my way home from work, he responded, “You’re kidding me! Let’s f*ck.” My heart sank immediately. I had such high hopes for him. I was crushed. “You don’t know who you’re talking to do you? This is [O.G.A.A.T.],” I shot back. He admitted to confusing me with someone else and began damage control. I think he immediately realized he lost any shot of anything with me, however, he still took the time to apologize profusely.
If you know me at all, you know I give second chances out fairly often. I decided to lay on the guilt a little bit, but also give him the opportunity to redeem himself. As I got off the bus, I picked up the phone and called him. His timing caught me at a vulnerable moment. I was turning my dating life around. I told him what he did wasn’t cool. Again he apologized. I told him I would turn a blind eye this once for one reason; a few days prior, I probably would have said the same thing on Grindr. I couldn’t hold it against him when I too had treated Grindr in this way. He fully comprehended what I was saying and promised not to let me down.
The following day, I asked him if he would be interested in drinks Friday for happy hour. He immediately agreed that would be a great idea. When Friday arrived, we made more definitive plans. Since I was done work before he was, I offered to come down to his neighborhood. I just told him to text me when I should start walking down there, and he did. I texted him when I got the bar, but he was still working. I told him I’d hang out by the bar for a bit. I walked a block to Starbucks, got a coffee and wrote a blog post. I needed a kick in the a$$, considering it was a Friday night after a long week. When nearly an hour passed, my patience was at its end. This guy was not winning me over by any means. I was a block away from the PATH and very tempted to just leave. Just as I was closing my laptop, I got a text from him. He was on his way.
We met on the street in front of Employees Only. He’d never been before, so I led us inside to order a round of drinks and find a wall to lean against. He apologized for taking so long and explained what was going through his head. He was working on something late and told the editor they’d need to pick it up again on Monday. He’d already used up one of his chances with me. If he messed this one up, there’d be no redemption. I thought it was cute, and I loved his honesty. We talked about our jobs and our shared favorite coworker. I told him about my coworkers and how we’d be excellent fodder for a reality show. (I really work with a circus of a crew, but I love them!)
We were really hitting it off. Everything just felt so easy. He was also incredibly easy on the eyes. I felt I was a bit out of my league here. He was five years my senior, gorgeous, smart, witty, well spoken, had a solid job, etc. Basically, he was the full package. I already knew he had a healthy libido as well, so we’d probably be fine there.
After two rounds of drinks, he took the opportunity to kiss me. I can’t tell you how much I loved that kiss. He was a real man, and he kissed me. I was crazy swooning. We decided to make moves. In our conversation, I was talking about what I do in my free time and mentioned the pier I lounge on directly across from the Christopher Street pier. He suggested we take a walk out there before grabbing a bite to eat somewhere.
We walked holding hands to the end of the pier. He took my bag, set it on the ground with his own, and we walked to the railing. He stood facing the water and pulled me in, wrapping my arms around him. It was incredibly romantic. While we talked, I nuzzled his neck. Things were so easy with him. There was no drama. There were no games. There was just us. I couldn’t believe an hour earlier I was ready to abandon our date and go home.
He turned around and hiked himself up so he was sitting on the railing dangling over the river. I was between his legs with my arms wrapped around him while we chatted. I decided to tell him how new to the game I was and tell him my coming out story. I figured I might as well get that out of the way, because if it was going to scare him off, I figured it was better sooner rather than later since I’d already grown so attached to him. He was totally cool about it. This is also when I learned our age difference of five years. Obviously I was fine with that considering Smiles was nine years my senior. He was cool with that as well.
As we walked to find dinner, he told me about his coming out story. It was interesting and not all that different from mine. I learned he was bisexual through college, which actually was reassuring to me. I liked men that had experience with women as well. It wasn’t a necessary skill I needed to see them utilize. I just liked knowing they’d experienced women as well and realized they were more attracted to men. It also generally proved to produce more masculine men, which I’m far more attracted to. I also learned in that conversation he was a cancer survivor. I didn’t know how this guy could get any better. He was like Superman.
The date was off to an amazing start. We were walking hand-in-hand to find dinner somewhere, and I didn’t want the date to end. I was on cloud nine. I think I floated the whole way. We finally arrived at a spot I was quite familiar with, Frankies 570. So familiar, in fact, I’d been there a few days prior. The date was just beginning. I couldn’t wait for the next course…Follow @onegayatatime
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 @onegayatatime
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.
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.Follow @onegayatatime
Friday arrived, and I was starting to nail down plans with Smiles for the night. He had things to do all day, so we planned to grab dinner and then head to his friend’s birthday party.
This meant I had time to kill after work. My good friend A asked me to grab happy hour drinks with her. She recently moved our of Hoboken into the city with her boyfriend, so I was already seeing a lot less of her. We were due for a catch-up.
She picked a place in the Flatiron District that’s known for their happy hour. We cozied up to a spot at the bar and chatted about our new situations. It had been a while since I caught her up on the status between Smiles and I. I took her for a ride on the roller-coaster ride of emotions I’d been through. She gave me advice on how I should proceed and things I should watch out for. After five years, she knows me quite well and can predict a lot about me, so I’ve come to listen intently to what she says.
She also took the time to talk about the new challenges she faced moving in with her boyfriend. I tried to give her my two cents for what it was worth. My biggest advice to her was to pick her battles. On the things she could let go, she should, but on the things she really cared about, she should make a stink. That way, he would realize with more poignancy when he was doing things that got under her skin.
In the middle of our conversation, Smiles called to discuss dinner. He chose a place about two blocks from where we were drinking, and we agreed to meet in a half hour. When the time came, and A and I had our fill of cocktails, we walked to the restaurant Smiles chose. I coerced her into coming along to meet him since none of my friends had the opportunity yet.
I introduced them to each other, and Smiles invited her to join us for dinner. A had plans to meet her boyfriend for dinner, and I could tell she was looking for a quick exit, so she agreed to sit with us for a few minutes. She was already running late. I appreciated her making the extra effort, and gave her the out she needed. I told her to get on her way.
After she left, the conversation with Smiles was slightly forced and awkward. I was having a hard time breaking through and there were periods of silence. I learned he was feeling very sick and his stomach was bothering him. He had issues with his appendix, and it was inflamed and bothering him again.
Now, I was worried. I genuinely cared for him and my paternal instincts kicked in. I was worried for his safety and said, “Don’t be a hero on me here. If you aren’t feeling well, we can go at any time. Don’t soldier on on my account.”
“Thank you for your concern, but I’ll be fine,” he replied.
The rest of the meal was pleasant, but quiet. I reached my hand under the table to rub his knee to try to make a better connection while we chatted. That, and I was still worried about his condition.
When we finished dinner and desert, we had some time to kill. Smiles walked around the neighborhood looking for a massage parlor (legit, not sexual) in which to kill time before the birthday party. We couldn’t find one still open to take advantage of, so we hopped in a cab and made our way to the party.
When we arrived at the party, I was slightly overwhelmed by the crowd. I’d never been to a party so heavily skewed male in my life. I learned the birthday boy was gay, which answered a lot of questions for me.
We found a comfortable spot to plant ourselves and each grabbed a drink and something to nosh on. We made a friend and chatted with him a bit. He was an extremely jacked and cut black man who is an interior decorator. It was interesting hearing him talk about his occupation, all while looking at someone who looked like a personal trainer.
After some time, this man turned to us and said, “Oh. Are you two together?”
Both their eyes focused on me. The pressure was on. I didn’t know what answer Smiles was looking for, but I saw this as an opportunity to gauge his reaction. I tilted my head slightly to the side nodding and said, “Yeah.”
Our new friend called attention to and questioned my head tilt heavily. I pointed out we didn’t know each other all that long. I still look back and wonder if Smiles was actually looking for me to say yes. I still wonder if he was being distant because he thought I wasn’t fully invested in our budding relationship. Of course I wanted to say yes, we were dating, but I didn’t know where his head was at the time. I didn’t want to scare him off by being overzealous.
We were nearing the time to head out for the night, but I needed to use the facilities first. That was particularly a challenge because the bathroom was being used by a few to sign a birthday book photo album. Finally, I gave up and assumed I could go when I got back to Smiles’ apartment.
We went downstairs and hopped in a shared cab with one of the female guests from the party. As we progressed, I learned I would not be going back to Smiles’ apartment. My destination was the PATH to go home. I was slightly shocked and annoyed. It was a Friday night. Why wasn’t I being invited back to his place. I know I’d never been there before, but this was a bit ridiculous. It was around midnight, and I was dreading my trek back to Hoboken.
He hopped out of the cab with me. We said goodbye on the street with a quick kiss, and I was on my way home. I’m not gonna lie. I was hurt. I felt rejected. There was only so much rejection I could take.
As I walked, I pulled out my phone. I called Boston, but of course, he was still ignoring my calls. I left him yet another voicemail. I also called my new friend to see what he’s been up to. No answer either. Finally, I texted the Principal. It’d been a while since we chatted, so I thought I’d given him enough space. We began texting, but I told him I’d have to continue the conversation on the other side of the river.
While waiting for the PATH, I nearly p*ssed my pants. The train going into the city dropped off a tranny who felt the need to flirtatiously wave at me and say hi. When it finally arrived, I leaned my back against the wall and closed me eyes to concentrate on something other than my bladder. Two women were in front of me on the crowded train, and around a turn, one fell into me. They started arguing with each other and engaged me in conversation. Though not stated outright, I learned they were a lesbian couple, and they were hot. We had a long conversation, and when we arrived at the Hoboken stop, they invited me to come hang out with them. They had no idea my preferences fall in the men category, and they were inviting me back to their place. I used my bladder as an excuse and said goodbye. It was early enough, but I was not in the mood to play.
While speed walking home, a very large black girl grabbed my arm, pulled me towards her, and shouted, “TAKE ME HOME WITH YOU!” I ripped my arm free and continued to walk home, all the while texting with the Principal. I was flirting slightly, but not to the point of crossing the line with him. I missed talking to him and our flirtations. I really did like the guy, but the distance was still killer.
When I got home, I relieved myself and hopped into bed. I was disappointed I was there alone, but I opened up a whole new can of worms with the Principal. He still wasn’t over me, and I just scratched open that scab again. I even went as far as to pull up Grindr again for the first time in over a month.
It was just my luck. The one I wanted to be spending my night with just sent me on my way, while everyone I didn’t want anything to do with seemed interested in me.
Furthermore, I wouldn’t be seeing Smiles the following day. Originally I was planning to go to a horse race in New Jersey and invited him to join. When the day was approaching I was no longer interested in going and sold my ticket. I was hoping to spend the day with Smiles, but I learned he was going to Six Flags with friends — without me. I understand he has a life of his own, and I don’t have to spend every waking moment with him. But at this stage in our relationship, I wanted to spend more and more time with him. I certainly would have invited him on a fun trip such as the one he was going on. Apparently, he didn’t feel as strongly for me. A clearer picture was being painted for me. Maybe he just wasn’t that into me.
I realized things weren’t going as smooth as I would have liked, so I set myself on entertaining other ideas…Follow @onegayatatime