Posts Tagged lawyer

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…

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

Leave a comment

Harvard Law’s Review

After meeting the police officer and the southern gentleman, I was on a roll. I was getting through my roster of men with ease. Monday was no different — I scheduled in a new one, “Harvard.”

I picked him up on Grindr one late night in the city. He was a very attractive lawyer who seemed pretty normal and very masculine. He went to the gym a lot, so his body was tight, and he seemed like a genuinely nice guy. We exchanged numbers shortly after we began talking on Grindr. I texted him a few times while on vacation with my family to make sure he was still thinking about me periodically while I was gone. He was another guy I thought had a lot of promise.

The night before, while waiting for the bus to meet the southern gent, I called Harvard. He picked up, and we chatted a bit. I told him about my vacation and he told me how similar his family is. He had a trip coming up in a few months and felt the same way about it that I did about mine. It was easy to talk to him. He sounded great too. No flamboyance at least. I was looking forward to meeting him in person. I thought to myself, “Maybe a phone call should be a new part of the screening process before the first date. I could eliminate a few bad apples this way.”

On the walk home from my date with the souther gent, we texted each other. He managed to slip in a comment about how much he liked my body. I certainly appreciated the compliment and threw one right back in his direction.

We scheduled a date that Monday evening at Blockheads, and outdoor Mexican restaurant. This would be my third date in two days — I was speed dating over the course of a few days. I arrived early, so I put our name down and sat to read Chelsea Handler’s My Horizontal Life until he arrived. (She’s part of what inspired me to write this blog, so I thought I should at least read her books).

When he arrived, we were seated immediately. We had a nice table for two on the rim of the crowd. A few birds flew around our feet, and he started to freak out. I get weirded out when pigeons do it, but these were tiny little birds, not the flying rats I want to punt every time I see them. Now, I’m not judging, but it was a bit excessive. He freaked out and told me how much birds skeeve him out, but I was still a little weirded out by how much it bothered him.

I started to size him up. He looked like his pictures and he filled out his polo very nicely. Great arms and a great chest. I could tell he was a regular athlete who hit up the gym. This is important to me since I am so active. I need someone who can keep up with me.

We started on the small talk. We chatted about college, family, vacation, where we grew up, what we did for fun. It was almost as if he was reading from an interview script. The conversation was alright, but it certainly wasn’t relaxed. I was a little turned off because everything he said had a slight air of superiority to it. He was trying too hard to impress me, and if there’s one thing that turns me off with people, it’s that. He even wore his pretentious college ring. He was a nice guy, but I couldn’t take the high brow attitude.

In between all this, the waiter came by to take our drink orders and then our dinner orders. Every time he came by, Harvard started flirting with him. It was obvious this guy was a ‘mo, but he wasn’t even attractive. The waiter is supposed to flirt with you for a good tip, not the other way around.

We both enjoyed our meal and continued the “interview” while we ate. He told me about his “type.” I fit the mold perfectly as far as physical looks went, but I have a feeling he was looking for a younger or more subservient guy. We would butt heads, and I think he was looking for a guy he could rule over.

When the date ended, we hugged goodbye. We didn’t even talk about follow-up. We both knew there were no fireworks there. On my walk home, I texted him, “It was nice to meet you.” He responded, “likewise.” After that, it was simply on to the next guy on the list…

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

Leave a comment

Was that a Date?

I first downloaded Grindr as I was pushing back from the gate on my flight to San Francisco for business. Upon my return, I often played around with it at work. Early in my Grindr experience, I found a VERY sexy torso to strike up a chat with. The guy seemed very level-headed and not simply interested in hooking up. I also discovered he worked across the street from me.

But, when I asked him to hang out, he got very shy. He told me he was very picky and wasn’t that interested in meeting someone. I asked if he would grab a drink after work sometime, and he kinda let me down easy. Periodically, I messaged him after that just to say hi, but I never got much of a response. It was disappointing. Finally, I gave up.

Then one day, out of the blue, he messaged me. He asked if I had just been in Bryant Park sitting on a park bench for lunch. I was impressed and thrilled he recognized me without having met me. Ironically enough, I was on a lunch date with someone from adam4adam.com.

We chatted about the chances of him picking me out of a crowd in the city. I brought up the idea of getting a drink together. A month passed by since the last time I asked him. This time he was ready to play ball, maybe since he saw me in person? Not exactly sure. Either way, I convinced him to send me both his number and a picture of his face. At this point, I’ve had so many guys’ numbers in my phone, I needed some way to keep them straight (the first sign I was becoming a whore). My strategy was to get pictures of them to attach to their contact profile. I’m much better with faces than names.

A week later, on a whim, I sent him a text asking if he would be interested in grabbing lunch that very afternoon. I knew it was a long shot since it was such short notice, but why the hell not. Much to my surprise, he agreed. I had to run into a meeting, but would be able to meet immediately following since my work for the day was pretty much over. I told him to pick a spot. He told me he’d get right on it.

We met in the square between our offices and walked to KyoChon for some excellent wings. I had never been there before, so he explained all the ins and outs to the place. We took our food and grabbed a table upstairs.

He was great company. The conversation started immediately when I met him. The whole walk over we chatted about careers and how we got where we are today. The conversation still flowed while we ate. There were no awkward pauses or hiccups. I was very comfortable with him. He also had a great smile, something I’m coming to find is a weak spot for me. Ironically enough, he looked like Boston, had the same name as him, and he recently moved to NYC from Boston. The resemblance was a little uncanny, but I moved past it quickly.

I had a lot of respect for him. He left a very successful job at a law firm to come to NYC to find himself. He wanted a new job, but didn’t know what he wanted to do. He just knew he wasn’t going to find himself in Boston. Right now he was working in marketing, but that also wasn’t exactly what he wanted to be doing. He was still on the path to clarity.

We also talked about therapy. He was seeing a psychologist from time to time to talk through issues. He told me most people don’t realize it’s covered by most insurance companies to go for periodic sessions. He explained how it’s been a good outlet for him to get his head straight. I didn’t see him as a crazy person. I actually saw him as more sane for having such a healthy respect for it. I began to entertain the idea myself. My friends are my therapist. I have abused many of my friends in this respect and turned to writing a blog to alleviate some of that burden. Maybe a therapist was what I needed.

This was truly a quality guy. A guy I really wanted to get to know. I knew I would need to take it slow with this one. I didn’t want to come on too strong and turn him off right off the bat. We walked back towards our offices and said goodbye with a nice handshake. He turned and said, “This was good. We should definitely do it again!” I was very happy. I passed the test. Also, was this a successful “date?” It didn’t quite feel like it was a date going in, but maybe it was a lunch date by the time we were done. I was looking forward to our next.

As time passed, I didn’t push the issue of a second “date.” I also became distracted with other guys, but one day, while going through my contacts, I discovered him again. I shot him a text asking if he’d want to grab lunch again soon. He told me he was out-of-town for the week, but we would touch base when he got back the following week. Only time would tell if we’d figure it out…

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

1 Comment