Posts Tagged difficult
Another Monday. Another day at work. My staycation was officially over. Another day periodically checking Grindr.
I spent my vacation getting myself back. The only problem was I only repaired the physical me, not the mental and emotional me. I wasn’t on Grindr all day long, but I would periodically check it to see if anyone had messaged me. I was simply a Grindr fish. No longer would I be a fisherman.
I had a dermatologist appointment in the middle of the day. While walking to my appointment, I fired up Grindr. I was curious to see if anyone was scoping me out. I was also in a new neighborhood. I was hoping to find something new and unexpected. In the short window it took me to walk about twenty blocks, I’d managed to strike up a conversation with three different guys. All seemed to be quite level-headed. I told them all I was looking for dates, and all of them seemed excited at the prospect. It was difficult trying to keep three conversations going at the same time. I told them I was walking into my appointment and asked each of them for their phone numbers. I managed to pick up a lawyer, an actor and someone who worked for a magazine rating cruise ships. I asked each of them for their pictures to add to my roster and went to see my doctor about lightening up a scar.
When my appointment was over, I thought I’d make my walk seem shorter by checking messages on Grindr once again. A guy near my office was on and started messaging me. He seemed pretty hot and well fit. He was staying at a hotel near me and was anxious to give head. I told myself not to even continue the conversation, but once again, I found myself thinking with the wrong head. I entertained the idea and asked him what he was proposing specifically. He told me he had to catch a flight in a short while, but wanted some fun before leaving New York. I immediately knew which hotel he was staying at and his occupation. “You’re a flight attendant staying at the Radisson, aren’t you?” I asked. “Yea. How did you know?” he replied. “Not the first one I’ve talked to at that hotel. You guys love that hotel, and you guys love Grindr. So what exactly are you looking for?” I texted.
He asked me to come to his room. He would leave the door ajar. I would walk in, he would tear off my pants and just begin orally pleasuring me. I wouldn’t have to touch him or do anything to him. He just really wanted to blow someone. I knew better, but I still bit anyway. I figured, “What’s the harm?” Work had no idea how long my appointment would last, and it was a slow day at the office. I decided to take a detour, but I basically had to run to his apartment. Thank God I have long legs to get me there. He was anxious because his checkout was very soon.
I arrived at his hotel in time for an afternoon tryst. I hopped in the elevator and made my way to his room. I’d been here before. This wasn’t my first b.j. from a flight attendant at the Radisson. I really needed to stop making that a habit, but at the time, I was excited to get off in the middle of the afternoon. I arrived at his room, and the door was left ajar.
Warning: The following may be too graphic for some. I walked in and said hi. He immediately began lifting my shirt and sucking on my nipples. I lifted my shirt off, and he undid my pants. Just then, he turned to me and asked, “You’re really clean right?” I assured him I was. “You can never been too sure,” he added.
He began pleasuring me. After a few minutes, I made my way to the bed and laid back. I wanted to fully enjoy him. It wasn’t too long before he worked his magic, and I was able to conjure up exciting mental images. I shot in his mouth and all over his face and chest. He spit on my chest and began working on himself. Seconds later, he shot all over my leg. “Let me grab you a towel,” he said immediately. I wasn’t moving. I was quite anxious to get both of “us” off me.
I cleaned up and began to exchange small-talk with him. He was Austrian and was headed home that evening shortly after I would be departing his room. I needed to get back to the office, and he needed to finish getting ready for work. He told me how much he enjoyed himself, and with that, I made my way out the door.
Shamelessly, I had a smile from ear to ear. I was still high from the endorphins. It felt amazing. I was ashamed and proud in the same moment. I still knew I was broken inside and needed to stop having these trysts with strangers, but I was also enjoying my sexual liberation. Somewhere, there had to be a happy medium. It was up to me to find it…Follow @onegayatatime
Since I’ve been slacking, I’m going to make it up to you this week. Hope you don’t have a busy week, because you’ve got a lot of content coming your way!
For as long as I can remember, I was trying to nail down a date with a specific guy I met on adam4adam.com. He had the cutest smile that could light up a room (in case you haven’t noticed — and I’m just coming to this realization — I’m a sucker for smiles). He messaged a few times on a4a, but nothing ever materialized.
Months passed, but I could never seem to get him to meet me. He’d show a lot of interest, and then he’d disappear for a bit. Like the ocean, it was a constant ebb and flow with him. Finally, I just flat out gave up on him, and I didn’t hear from him again. When I broke up with Smiles, I went back through my saved messages and decided to hit him up and see if this time would be different.
Ironically enough, I learned he moved out of the city. He was originally from Connecticut, and he moved back home with his parents to save a little money. It seemed now he was interested in finally meeting me, just when it would be most difficult. We discussed many evenings as possibilities to grab a drink before we finally found a good day to grab lunch. Even then, we were playing things by ear.
Of course, this didn’t happen. He had to cancel on me. However, he proposed raincheck options. He agreed to meet me for a drink one night after work on his way to Grand Central to hop on Metro North to CT. I did some research to find a bar that would be convenient for both of us. We set a time, and I told him to meet me at Annie Moran’s by Grand Central Station.
I was already having reservations about this guy. Was this how it was going to be all the time. Quick rendezvous before he went home? I finished work before him, so I decided to walk there instead of taking a subway or cab. It was raining lightly, so I broke out my umbrella, however I wasn’t walking alone. I had Grindr to keep me company while I walked. I’m such a whore. I was already looking for the next date before this one even got off the ground. But, it’s what you gotta do if you have an aversion to gay clubs. I stood outside the bar paging through profiles while I waited for him to arrive. He too was walking from work, and he worked about fifteen blocks away.
Just before he walked up, he gave me a call. I told him where I was, and when he saw me he hung up. As he walked towards me, he wasn’t quite what I was expecting. It wasn’t a bad thing; he was just smaller than I originally thought. We greeted each other with a handshake, and with that made our way into the bar. He offered to buy me a drink since I’d been waiting for him. I was in charge of watching our bags and trying to find a piece of real estate to stand/sit and chat.
He came back with the beers, and we dove into conversation. It was slow going at first, going through the standard order of questions. As he talked about his job in fashion, I noticed a bit of flamboyance coming through. I wasn’t thrilled, but it was far from a deal breaker. He was certainly cute (although he looked much cuter in his pictures before he cut his hair shorter).
We talked about family, work, his moving back home, where I live and grew up, commuting nightmares, etc. It was nice. I couldn’t quite tell if he was all that into me. I was starting to think he thought I was too “straight” for him. But, as the conversation progressed, his body language began to change. I realized he may have just been nervous. Once he relaxed, I could tell, he was flirting a little heavier. After the first beer, he asked if I wanted another. I gladly accepted. I figured he was going to dictate the end of the date since he was the one who had to catch a train. He told me all about his curfew and how he’d have to take a taxi if it got past a certain hour; his parents would no longer pick him up.
We talked about watching sports on TV and participating in them. Somehow skiing came up, and I told him my story about the first time I skied and how well I did. When the group next to us lef their table I snatched it, while he got us a third round of drinks. The date was going well, or at least I thought so.
While we sat, he took the opportunity to touch my leg periodically. I love that. It’s a surefire sign of interest. I returned the favor as well. I could tell there was a lot of sexual energy between us as well. We were both feeling it. We talked more about what we do for fun when we’er not working. He told me about his old apartment and how he still comes back into the city to do rotating dinner with friends at their respectful apartments. There were slight awkward pauses, but that can be warranted on a first date.
When he finished his third beer, he told me he had to be running for his train. I thanked him for picking up the tab, and I told him I would pay next time. “If there can be a next time,” I added. I walked him to the doors of Grand Central and said goodbye. He was lingering, and I could tell he wanted a kiss. I wasn’t sure his position on PDA, but I decided to go for it. I wanted a kiss, so I was going to get one. I leaned in with my arm behind his back and gave him a nice quick kiss goodbye. We agreed to find time to see each other again soon as we parted ways.
On my ride home, I took the opportunity to text him and let him know I thought he was cute. He told he had a great time, but also told me how he’d locked himself in the bathroom on the train. It was a really funny story, and I was happy to hear he had such a great sense of humor and easy-going personality. He told me he wanted to grab lunch later in the week, and I agreed. We would figure out a time that worked for us both. I was already looking forward to it…Follow @onegayatatime
Today is a Fast Forward Monday!!!
My apologies to those who have come to expect Fast Forward Fridays. I have been traveling for work/pleasure, and I got caught up in things. I haven’t had a chance to write the second post, so I’m making up for it today. 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…
After missing the opportunity to finally meet my online friend after almost a years time chasing each other around, the day finally arrived when I was scheduled to finally meet him in the flesh. This was well overdue, and I was quite excited. I wasn’t about to get ahead of myself, but the suspense had been building up for quite some time.
We discussed where we would go for drinks or dinner and finally settled on Charritos, a Mexican restaurant I’ve been to on numerous occasions. In fact, this wasn’t the first date I took there. We planned to meet at 7:30. I knew the place didn’t take reservations, but it was a Monday night on a holiday weekend. I figured everyone was home getting ready for the coming workweek. It also wasn’t the nicest night, as snow was in the forecast, so I thought we’d be alright.
When I arrived, I was immediately proved wrong. I stood in front waiting for him to arrive noticing every table (all 8 of them) filled with diners. Finally, he arrived, and we attempted to go inside out of the cold. Even this proved difficult since there was nowhere to go once we were in there. While we waited for a table to clear, we awkwardly chatted.
This was surprisingly difficult. He seemed so incredibly flirty online and charismatic, and the man standing in front of me was a very shy reserved individual. I couldn’t get over it. Where was the guy I’d been chatting about my body and sexual interests in detail? Where was the flirt?
We talked about work and the weather. It was a struggle to find a topic to discuss. Everything felt forced. It wasn’t awful, but it certainly wasn’t what I expected.
Finally we got a table and sat. After we ordered, we started to chat a bit more. I asked most of the questions. He always responded in detail, but he never asked a question in turn. That may have helped the conversation flow much more freely, but it wasn’t there. I had to volunteer all my information. I feel awkward talking about myself when I wasn’t asked to. It was as if I was interviewing him for a job.
One topic we got on was siblings. I don’t know why, but that topic has been coming up more and more frequently on my dates. I’ve actually noticed it and tried curbing it. I learned about his siblings as well. It was nice to hear he came from such a similar family dynamic.
We talked about his job as well. I was very intrigued by it. He told me all about his schooling, his specialty in the field relevant to the gay community, his boss, the clinical work he does… This was really shaping up to be quite the catch of a man. He was very sweet and thoughtful. However, our chemistry was not mixing AT ALL! It was so disappointing. On paper he looked so good. Online, he seemed a sexual match for my libido. In person, he was a mouse. Night and day from my expectations.
After quite a while, the waiter basically asked us to leave. There were people waiting for a table, so they kicked us out. I was more than a little p*ssed, because I thought it was very unprofessional and rude, however, it was time for the date to conclude.
We’d already talked about him coming over to my apartment before the date. I was still very sexually attracted to him. I wondered if he’d relax when he was out of the public eye. As we walked outside, I asked him where he parked and told him I’d walk him to his car. I was hoping for a signal along the way to show his interest. I thought he’d drive me to my apartment and come up.
I thought we’d at least say a proper goodbye. I was hoping for a kiss considering all I could think about during the meal was how good his lips would feel. When we got to the car, I stood on the sidewalk, and he walked to the front passengers panel in front of the rearview mirror. That would have been fine. I may have even used the car as a backboard for a strong kiss, BUT there was also a chopped off parking meter between him and myself. Yes. A metal pole about four feet tall was between the two of us. I don’t think he could have strategically showed his lack of interest any more other than to simply get in the car and drive away.
We said goodbye, and I told him it was nice meeting him. He said, “Likewise.” That’s when I grew some balls and took what I wanted. I moved forward, reached my long arm over the pole, hooked it under his arm around his back, and pulled him in for a kiss. It wasn’t a long kiss or a makeout session, but I certainly wasn’t going to be satisfied with a peck.
And with that, I turned and walked home in the flurries falling from the sky. I was still a little blown away by the lack of spark during the date. I wasn’t even ready to go home. I decided to stop by my friends’ place on the way home and say hi.
I came in and we caught up on what’s going on with each other before I told he and his wife about my awkward date. He was a little baffled by it as well. He couldn’t understand what was going on. He really loved the parking meter pole story as well. I was so nonplussed.
I sulked home after saying goodnight to my friends. When I got home, I was curious to see if he was back on a4a. Surprise! I was right. I wasn’t going to get past this immediately. I needed to ask him about what happened.
“Surprise, surprise. Look who’s on here,” I messaged him. We chatted a bit awkwardly about the date. He messaged me back: “I was waiting for you to ask me to come back.” He wanted to come back to my apartment. He even brought his c*ck ring and poppers with him. I was so confused, and I made that clear to him. He wasn’t aware of his mixed signals, nor was he aware of the pole. He just thought I wasn’t interested since I walked him to his car. It was all a big misunderstanding. “I had a good time. I thought the conversation was nice,” he added. That doesn’t make up for the awkward date however. That just cleared up the mixed signals at its close.
Just to satiate my curiosity, I told him we would have to try to fix what went wrong when I got back from my work trip to San Francisco. He agreed, so we kept in touch over the next week.
I decided to see what was going on with the southern guy. He texted me to see how my weekend was, so I picked up the phone and called him. Again, we talked for almost an hour while I packed. This completely made up for my awkward date. I was really looking forward to getting back so I could finally meet him. Hopefully this one wouldn’t be as big a disappointment.
In the morning, I had a message from my new southern gentleman caller. He was asking for a picture of my “morning excitement” we’d discussed previously. I denied his request and told him he’d have to wait to see the real thing. This was my way of getting him on the ball about meeting up with me.
I also got a text message from my friend and recent neighbor. It was very sweet of him to do so. I needed to make it a priority to hang out with him when I got back to New York.
All that would have to wait on the backburner… The following day, I was headed to San Francisco for the week for work. Waiting for me were two men. One I attempted a long distance relationship with whom I would meet for a cocktail. The other, a great confident and online friend whom I was extremely excited to meet in person, especially in the bedroom…Follow @onegayatatime