Posts Tagged staycation

Leavin’ On a Jetplane

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.

He was very worried about STDs and HIV. I assured him I was clean. I also asked if I would be allowed to play with his manhood if I chose to. He enthusiastically said yes.

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…

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Spring Break Flake

This is my 300th post! You guys have been amazing! Here’s to many more to come!

I was particularly excited about my staycation because I was going to get to see Boston again. We made very tentative plans for him to come down for at least part of the week because he was on spring break from school.

As we got closer to the visit, Boston went dark on me. It was pretty standard for him to not return my calls. The only time I ever got to chat with him live was when I called on a Friday night when he was pregaming before hitting the scene. I understood he was very busy. It was his final year in school, and he had a lot going on. On top of classes, he was searching for an internship. He was even looking at a few places in New York City. I was very excited at the prospect of him being nearby, but I wasn’t getting ahead of myself.

I was more than annoyed this time because I was expecting him to visit or to have me swing up to Boston. I had to use the time off. I thought it would be a good time to try to see him. I’m sure he is reading this right now ready to kill me. He probably thinks this is a bit of a guilt trip, and it is. But, it is also part of the bigger picture for my week off. I made no plans because I thought I had some plans. Granted, even if I didn’t have those plans with Boston, I probably would have been doing the same thing — Lounging on the pier, going to the gym and having sex.

In early March, I tried to see if he was still coming to visit. “Gaah. Haven’t even thought about it yet. I’ve been drowning in work. I’ll know by next Wednesday though. That’s when midterms are over.” After that, complete darkness. I didn’t hear from him for a few weeks. I angrily texted him from the pier one day, “You could just text me back you don’t want to/can’t come…” After my vacation had come and gone, he finally texted me back: “Just got my phone back today. Lost it over St. Patty’s Day weekend. Will call you later tonight. You gonna be around?” Of course I would never receive that phone call. I did understand though. He was in college. I tried to put myself in his shoes, and I realized I wouldn’t have come down to visit either, however, I would have told him I wasn’t coming.

After time passed, I playfully texted, “As much as you suck for bailing on me, ‘A$$ Grab’ is not gay. He just showed up to the bar with a girl.” Surprisingly, he quickly responded, “Means nothing. And I didn’t bail on you!” I wasn’t going to let him get away with that. “Um. Yes you did. Just sayin’,” I added. He was quick to note, “We never had plans and this break hasn’t been conducive to going to NYC and back.” I pointed out our tentative plans and his lack of communication in his inability to come. I also pointed out that even though he lost his phone, there are other ways to reach out to me. I also expressed my disappointment in not getting to see him. It was something I was really looking forward to. He responded back saying, “Alright. I’m sorry. Been in Vermont all weekend and all break I’ve just been busy working, so I’ve been flustered a bit.”

Again, I understood, and I fully forgave him. I wasn’t going to hold a grudge for that. Time off when you’re as busy as he is can be precious time. I kept myself busy taking admiring guys on the pier in the sun in Hoboken as you see in this post.

I depend on him more than I should. The problem is I don’t have any gay friends. When I have something I want to share, I feel like I’m putting some of my friends out by talking to them about it. They just can’t relate, and I’m sure they’re tired of hearing it from me. I turn to him because I know he’ll give me sound advice, but also because I have no one else. This post may come across like I’m bitter, but that’s not the case. I truly appreciate Boston and everything he’s done for me. He’s a good guy.

We still good friends, and he still ignores my phone calls. But, I’m sure all that will change when he’s finally graduated and eventually moves down to New York. Or at least I can hope, right?

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FINALLY!

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…

Saturday had arrived, and it was St. Patty’s Day. I was out early in the morning to hit up the gym. I wasn’t going to find myself wasting another day lying around my apartment looking for sex. It was the true start to my staycation and to the new me. It was gorgeous outside, and I was motivated.

As I left the gym, I ran into K and one of my other friends. They were heading into the city to drink, but I wasn’t interested. I’d just come from the gym. I’m not a fan of day drinking to begin with. I said goodbye and continued on my way home. D’s girlfriend was up from Philly that weekend, so I texted them to see what they were up to. They were grabbing brunch and had no plans for the rest of the day. I told them I was bored and lonely, and if they thought of anything, I’d be game. I also called my old roommate to see what he was up to. He was studying for yet another test he had to take for work. I knew it was useless to try to convince him to do anything else.

Finally, D and his girlfriend decided to swing by. They came up, and we just lounged around chatting. She’d never been to my apartment before, so I showed her around. After some time, we decided to go for a drive and check some new cars for D to possibly lease. I was game, so we made our way uptown in the great weather to D’s car.

We decided to drive around Jersey City since there were a few nice neighborhoods I’d never explored. I was a bit curious, and the other two were as well. I also wanted to scope out a spot I had in mind for dinner that night with the guy I spoke to on the phone for two hours, Travel Agent. We drove by the cute cafe on the corner in an upscale neighborhood of Jersey City, The Hamilton Inn. I’d seen it a few times before and had been curious how it was. I pulled up the menu on my phone and suggested the idea to T.A.

He was still working, but he said it sounded like a good idea. We planned to work out the rest of the logistics later.

We drove around for quite a bit more before finally returning to Hoboken. They dropped me off at home. I hopped in the shower and began to get ready for the evening with T.A. I’d been texting him a bit and made a reservation at the restaurant for 7:00. When he told me it’d have to be later, I called and changed the reservation for 8:30. When the time came, he picked me up in his nice Audi. He was a good-looking guy. He wasn’t someone you’d stop on the street and say, “Damn!” but he was good-looking. We jumped right into conversation. It was fairly relaxed. I feel he may have been slightly uptight, but I tried to remain candid and relaxed.

The Hamilton was exactly what I was hoping for. It had a decent crowd, the food looked and smelled amazing, and we got a nice table to sit and chat with each other. The obvious and easy thing to decide was to order a bottle of Malbec to share. I still couldn’t help feeling he was uneasy about things. He just didn’t seem to relax. I tried to lighten things up and asked if he wanted to split an appetizer. He agreed, but it wasn’t terribly easy to pick something. He defaulted to me, and after discussing it, I finally decided on the pierogies with goat cheese appetizer.

We began by talking about where we grew up in more detail than we discussed on the phone. The conversation shifted to our jobs. I got to learn in greater detail what he does. I told him about my job, and slowly I began to realize I was monopolizing the conversation. He’d ask me a question, and I’d answer in detail. When I’d ask him questions, his answers would be short. I wanted to get to know him. He seemed like a decent guy.

The waiter returned and we ordered. I was debating between he risotto and chicken. I decided on the chicken, and he decided on the risotto.

We talked some more until our food arrived. Or should I say, I talked some more. I would never say it was a bad date, but I would also not say it was a great one either. We shared some of our meals with the other. It was a nice time. I was enjoying his company, and the food was delicious. I was looking forward to a second date so we could think of something more relaxed to do. Hopefully that would break him out of his shell.

We declined dessert since he had to get home because he had a big work project the following day. He expressed to me how much he enjoyed the date. I was happy to hear it. We split the tab and made our way back to his car. On the way back to my apartment, we passed another restaurant I was interested in trying. I mentioned it to him, and he said, “Maybe next time we should try there.” That was a very hopeful statement. If he was already thinking about next time, maybe he really did enjoy it too.

We stopped in front of my apartment, and he put the car in park. He leaned over and gave me a kiss. I pulled back and went in for a second. It was nice, and I wanted him to know I was interested. I told him, “Call me when you’re back from Mexico. Or, you can text/call whenever you like,” with a smile as I exited the car. He told me we’d be in touch.

After that, I heard nothing from him. He clearly stated his enjoyment and mentioned a second date. How was I not supposed to think he was interested? I sent him a text to tell him of my good time with him, but I got no response. I checked Grindr, and sure enough, he was online. Clearly he was ignoring me. I messaged him on Grindr as well. When a day passed and I heard nothing back, I decided he would either deny this or the “relationship” would be dead before it began. “I hope you’re not ignoring me. I thought you were a classier guy than that.” He had given me two different phone numbers, so I asked if I was texting the wrong number. Finally, he responds explaining he was busy and apologized. He told me he was interested in seeing me again as well.

However, after that, I didn’t hear from him again. I know when I’m not particularly interested in a guy, I don’t outright tell him that. However, I don’t talk to him about future dates to lead him on. It was very disappointing, but I wasn’t going to let one guy get me down. My Grindr diet was slowly working. I was back to concentrating on dates and not sex. Hopefully, with enough time, I’d find a good guy to settle down with — Someone to be the reason I delete Grindr forever…

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On A Sexual Roll

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…

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