Posts Tagged tryst

The Calm Before the Storm

CK and I had a rocky night, but before we laid our heads on the pillows, we reconciled our differences. There’s no fight we couldn’t get over. We were truly in love.

The next morning, I woke up early to work out with CK in his rooftop gym. It was our first time up there, and we were finally going to workout together, or at least we both thought so. It turned out, we had different ideas of working out. While CK was on his cleanse, I too was trying to lose weight. That was only going to happen for me if I did cardio workouts. Lifting wasn’t going to help me shed any pounds, and that was the priority over bulking up. He wasn’t willing to join me for cardio, and I wasn’t willing to lift, so we worked out at the same time on opposite ends of the gym. When he finished, I was nearly done my three-mile run, sweating profusely from head to toe. I wanted to take off my shirt and use it as a sweat rag, but I wasn’t sure if that was P.C. in his gym, and there were others working out as well. When I finished, we rode the elevator back down to his place so we could shower and get ready for work.

As per usual, we showered together. This had become a regular thing for us. We rarely showered alone anymore. We weren’t always making out or having sex in there: It just seemed a better use of both our time to shower together. We were beginning to work out a system between us. Our routine was falling into place.

The one thing I slightly resented when sleeping over at his apartment was the lack of breakfast. It was getting expensive for me to continuously purchase breakfast every time I slept there. I made sure to provide him with the necessary items for breakfast, but we hadn’t seemed to get to that stage at CK’s apartment. I wasn’t going to make a stink about that. One thing at a time. I was happy he finally had all his boxes unpacked and a bed to be honest. Breakfast could be dealt with down the road.

We got ready and were out the door. We’d also managed to figure out we could commute together to work. Originally, he was walking to a different subway than I was, but after further investigation, I learned we could both catch the necessary subways from the same station, and it would be the same distance for CK. Every morning we walked together and said goodbye with a kiss on the platform. It was a simple routine, but I was already thoroughly enjoying our morning walk to work together.

That night, CK had to work late. I went home and went to free outdoor yoga on the pier in Hoboken with my roommate instead of CK. We were spending the night apart. He had to be at work early the following morning for a pitch. When I got home from yoga, I made dinner, watched TV and fell asleep in my bed alone after chatting with CK about his day.

I woke up early the next morning feeling lost. The man I loved wasn’t there. It was shocking how much of a difference it made having him in my bed. I didn’t sleep nearly as well as I did when he was present. It was like I was an infant all over again missing my mother’s heartbeat. I needed to feel him close to me to get a good night’s sleep. I forced myself to get out of bed and motivated myself for a nice morning run along the Hudson. I stopped to take pictures for Instagram of the city where I knew my boyfriend was still soundly sleeping.

I ran back home, finished getting ready and stopped by the allergist for my shot before heading to work. I was really committing to getting in shape and losing weight, so that afternoon, I took lunch at the gym. I wanted a six-pack again, and I wanted shoulders, arms and pecs I could be proud of again. When I finished, I was in a spectacular mood. I shot CK a text to remind him how much I love him. I was also horny from the endorphins running through my veins. I started to sext him, telling him all the things I wished I could do to him in the gym shower.

Warning: The following may be too graphic for some. That’s always been a fantasy of mine, however, I never had any desire to do it with complete strangers. In an ideal world, CK and I would go to the same gym. We’d walk in together, but not acknowledge each other while we were in the gym working out. When he was finished, he would head into to the lockers to shower. He’d strip down in front of me, not acknowledging my existence before strutting to the shower of his choice. I would follow just behind and slip into his shower stall and close the curtain behind me. We’d have sex under the hot water without causing too much commotion to attract attention from others. After finishing inside him, I would rinse off and leave the shower like nothing happened. He would finished washing up and recovering from our tryst while I got dressed and headed home like nothing happened to start making dinner. He would follow a few minutes behind, and the first time we would acknowledge each other would be at the door where I’d welcome him home from a hard day’s work at the office with a big kiss. We’d eat our dinner with big smiles knowing we have an epic sex-life. Some day…

So in shorter terms, I described this situation to him over text. When I first began, he thought I meant to text someone else. He must have thought I was cheating on him with someone at the gym. I assured him the texts were for him and reminded him how the conversation begane explaining that this was my fantasy. I also pointed out the irony of the situation and detailed how he was the one who sexted the wrong person, not me (just like the first day we started chatting and he wanted me to come over for sex).

That night, I had plans to see Porgy and Bess with my coworker, so I didn’t see him again. I think he felt a bit left out, but I’d been coworkers with this girl for over five years, and the two of us had never hung out outside work together. I also had to head to our Chelsea office to work early in the morning. I took the opportunity of being off the radar a bit to hit the gym again that afternoon, this time for a run on the treadmill. I began thinking about CK and I in the gym once again, but it would remain a fantasy.

When I finished work, I went to my volleyball game, came home to shower and made my way into the city to spend the night in CK’s bed. We’d spent a decent amount of time apart considering we’d been spending every waking minute together outside our workdays. I was thrilled to see him and even more ecstatic I was sleeping with him that night. After a late-night romp, we dozed off in each other’s arms. When we woke in the morning, we hit the gym once again. Alas, we worked out on opposites sides of the gym once again.

When we finished, we continued our routine of getting ready for work and were out the door. That night, after work, I ran home and grabbed my things for the weekend. We had a big weekend coming up, and I had to pack for many different options. It was EXTREMELY frustrating because I wasn’t sure what we’d be doing, I wasn’t going to be home again until Sunday at the earliest, and it was Pride Weekend. I asked CK for help on what to pack, and he was of no use. The fight was quickly escalating over the phone, and my frustration level was at its peak. I wasn’t used to going to gay events and circuit parties, and I was feeling a lot of pressure. This was a burden I’d been carrying around for weeks, and the moment of truth was arriving. This was going to be my first full Pride Weekend, and I had no idea what I was about to get myself into. I was scared sh*tless!…

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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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Late Night Snack

After my tryst with the Armenian and the Asian, I decided to order some real dinner. This was the last night I was on the company dollar, so I ordered some room service. While I waited, I chatted with the guy who wanted to come by later in the night. I sat and ate my meal in bed with just the TV to keep me company. I was feeling lonely, which is such a strange emotional state to be in considering I’d just shared one of the most intimate acts with two other men.

When midnight arrived, I started texting my late night snack. I asked him what he thought his E.T.A. would be. He told me it was still up the air, but he was definitely coming by. He was out with friends and would swing by on his way home.

Finally, around 2:00am, he texted he was finding parking and would be by shortly. Ten minutes later, I had a knock at the door, for the third time in a matter of hours.

He was a very nice polite black man who was anxious to spend some time with me. He seemed very young and innocent. We chatted a bit while sitting on the bed before any action began. It was getting late, and as rude as this sounds, I was ready to get it in and go to bed. I wanted a nightcap so I could doze off soundly till the morning.

Warning: The following may be too graphic for some. We had A LOT of foreplay and prep before anything happened. He really wanted to cuddle for a long time before we could even get frisky. I was almost ready to call it quits and ask him to leave. It was getting late, and I was getting tired.

There was a lot of kissing. A lot of heavy petting. A lot of licking and sucking. Finally, he was ready and got into position for me to penetrate him. I could tell this wasn’t a guy who gave it up to just anyone. Normally, I’m really into the foreplay and making out, but I’d already had my engine warmed up earlier that evening. In fact, the car had been taken around the block a few times.

I’d saved my climax for him and quickly learned this was a big mistake. He was very bad. We didn’t go for very long because I really wasn’t getting anything out of it. Finally, I stopped and rolled onto my back. I tossed yet another condom in the trash and started taking care of myself. He laid next to me and asked me to finish on his chest. I obliged his request, and he followed suit shortly after.

I knew he was going to be a lingerer. I tried to cut that off at the pass. I humored him for a short bit of time before I finally spoke up and said how I needed to get to bed. It was past 3:00am. It was time for him to go! He got the hint and got dressed. While he did so, he asked if we could hang out again while I was in town. He told me how much he enjoyed himself. I didn’t shoot him down, but I didn’t exactly give him the answer he was looking for. I told him I’d have to see what my schedule allowed for. I told him I was trying to get the most out of my vacation in L.A.

With that, I said goodbye, shut the door, showered all the men of the night away, and climbed into bed to dream about the sunny sandy beach I would be visiting the following day.

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The Horror!

Touchdown! After a long flight of writing a lot of blog entries, I finally landed in San Francisco. I was very happy to be away from New York. This was forced time to clear my head. It would be impossible to try to find a guy for a date from thousands of miles away, and I needed a break. Don’t get me wrong, I want a man to call my own, but the process of finding one is exhausting.

I rode to my hotel with a very chatty driver. He had lots of questions and comments for me. Many of the comments referred to women and our “shared” desire for them. I didn’t have the heart to tell him I was gay. I just let him continue talking. It wasn’t that long of a ride.

I got to my hotel, and took my good ol’ time getting to the office. They didn’t know exactly what time I landed, and I’m sure they wouldn’t have any work for me yet anyway.

I was right. When I arrived at the office, they had no work for me the entire afternoon. This worked out quite well. It allowed me to update the blog and go for a nice long delicious lunch I didn’t have to pay for. When the workday was coming to a close, I made my way back to my hotel.

I’d been on Grindr all day hunting for a guy to either meet for a drink or have some fun with. Nothing was turning up. I recalled the last time I was out there. Originally, I had the same luck. That is, until I picked up signal from San Francisco. No such luck that day.

I thought about the other weapon in my arsenal. I could pull up adam4adam.com and see who was in the area. I managed to find a few sexy men to message. It was only a matter of time before one of them messaged me back. A few did, but many of them were flakes. A few of them were unattractive as soon as I saw their faces as well. I asked a few to hang out, and the ones only interested in sex, I proposed coming to my hotel. Some of the guys on Grindr offered bl*wjobs, but I was looking to get it in.

One guy was very willing to make the journey to my hotel, and he was a bottom and looked pretty sexy. I told him to come by and gave him the details. I had one failsafe. They would not be able to come up to my room without me picking them up from the lobby. If I was unsatisfied with what showed up, I could hop back in the elevator and shut the door. That’s terrible, I know, but you never know what will show up when push comes to shove.

I was doing it again. I ended a relationship and simply fell back into old habits of hooking up outside of a relationship. I wasn’t thrilled with myself, but I was giving myself a free pass while in San Francisco.

I would have to put off dinner until after my evening tryst arrived. I was hungry, but I wouldn’t have time to get dinner before he came by. When he arrived, I collected the man from the lobby. He was a good-looking Aussie.

We got up to my room and talked about where we were from and our stories. He sat on the bed and talked with me. He seemed like a pretty cool guy. He was a bit of a vagabond. I liked his traveling experience. I was envious of it.

When the moment was right, we both went in for a kiss. This was followed by LOTS of kissing. Lots! He seemed quite nervous. I was trying to get him to relax a bit. I took my time with him gently feeling his body. He was a good kisser. This was a good sign.

Slowly I began peeling off some of the many layers he was wearing until we were both naked. He had a decent body. He was skinny, but not exactly muscular and defined. The kissing became more passionate and the petting grew heavier. When we were pretty far along, I whispered in his ear, “I want to be inside you.” He responded the same sentiment, so I reached for the condom and lube I had in the nightstand drawer.

Warning: The following may be too graphic for some. Now I know I say this in a lot of posts, but this time, it may be too graphic for even those who are normally turned on by my warnings. Just be forewarned. Don’t say I didn’t tell you so!

I inserted myself inside him. He felt great. He seemed to really be enjoying himself as well. We were about two minutes in when something didn’t feel quite right. I took a whiff of the air, and immediately knew what was wrong. I looked down in horror, and it was all I could do to keep myself from vomiting all over this man.

I immediately pulled out and hustled to the bathroom. We both knew what was wrong. I tossed the condom in the trash and began scrubbing myself. I casually suggested a shower. I was trying to maintain my composure so this man wouldn’t feel worse than he already did. This was horrific, but I still had the man’s ego in the back of my mind.

He suggested I go first. I’m not sure why. All I could think about was his uncomfortable state while I showered. He made his way to the toilet and took care of himself while I washed up in the shower. When I finished, I left the bathroom so he could do whatever he needed to do.

I was still a little shaky and trying not to think about what just happened. I’d encountered this before, but never to this extent.

When he emerged from the bathroom, you could have knocked me over with a feather. He actually suggested we keep going. I was speechless. I didn’t know what to say. At this point, I no longer had the man’s feelings in mind but only my own sanity. I told him, “No. I think I’m done for the night.” He didn’t stop apologizing. “Don’t worry about it. It happens. Part of the territory,” I reassured him while he got dressed.

And then, when I didn’t think this man could surprise me any more than he already did, he suggested we grab food since he hadn’t eaten anything yet either. “No. I think I’m just going to order room service or something but thanks,” I added.

Just as he was walking out the door, my phone rang. It was San Francisco. I explained to my departing guest that I needed to take the call and gave him a wave goodbye. I couldn’t wait for him to be out of my sight so I could stop thinking about what happened.

“Helloooooo. How are you? Are you Grindring?” he said as I picked up the phone. All I could think in the back of my head was, if you only knew! I simply replied, “I’m single. I can do whatever I want.” We talked about our schedules for the week and planned a night we could grab a drink together. He suggested we meet in The Castro since I didn’t make it up there during my last visit. Once our plans were solidified, I hung up and tried to figure out what to do for dinner.

Joe’s Crab Shack was a block away and was one of the few places still open at that hour. I decided to go there. This would be the second mistake of the night, as this was the worst seafood I’d ever had. I couldn’t finish it. I was literally wiping the seasoning off the crab legs with paper towels, and I still could barely tolerate them.

If this was a sign of what was to come from my San Francisco trip, I was going to lock myself in my hotel room when I wasn’t at work. The positive was, it certainly couldn’t get much worse…

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What Doesn’t Kill You Makes You Stronger

Sunday afternoon, I tried to see if Smiles would want to do something fun the following day since I didn’t have to go to work. Sadly, he had work to do. He was trying to build up a company from scratch, and it is a lot of hard work, so I understood. What I didn’t expect was he would be busy he wouldn’t be able to find the time to pick up the phone and call or text.

Monday passed with me planted on the couch watching TV all day while surfing adam4adam.com and reactivating my Grindr account. I was just seeing what was out there, but as the afternoon progressed, I started to think toward the future while examining the past.

I realized I wasn’t happy. I equated my relationship to the struggle of Sisyphus, a king punished by being compelled to roll an immense boulder up a hill, only to watch it roll back down, and to repeat this throughout eternity. I was constantly putting work into the relationship only to find I wasn’t receiving much benefit from it.

I had given Smiles more than his fair share of chances to finally woo me, and he failed. I enjoyed his company, and he was a very nice, successful, good-looking man, but the time had come to move on. It just seemed he wasn’t that into me, and I realized I deserve better. Since I had been on the journey to this conclusion for quite some time, I wasn’t that broken up about it. I’ve had varied reactions to the end of relationships in the past. I moved on with closure after my mutual breakup with Broadway. I had slight some minor cardiac scarring after I ended things with San Francisco. I was a wreck when things went south with N — Losing ten pounds in a week (Not proud of that).

This epiphany wasn’t all that earth-shattering for me. Things had been on the decline for some time. This certainly didn’t come out of the blue, so the blow was lessened.

I actually started to get slightly angry about things. I felt used. I recalled asking Smiles on our first date why he was on Grindr, and he had mentioned he was lonely. I realized I was someone to pass the time for him. I was someone he could go to dinner with so he didn’t have to eat alone. I was someone he could have the occasional romp in the sheets when he was in the mood. I was a seat warmer. He never had any plans to forge a relationship with me, and this made me really feel used.

I wanted more. I deserved more. And I was going to find more. I started searching once again on a4a and Grindr. These are clearly not the best place to find Mr. Right, but it couldn’t hurt to try. Once again, it was just going to be a lot of work.

On top of it all, our sex-life was minimal. As a result, I was horny. I was hungry for some good sex. Over the summer when I was having my wild time, I felt I started to really hone my craft. I had numerous guys constantly hitting me up for seconds, thirds, and more. It was great for my ego, and I craved a really good romp in the sack.

That’s when I turned my efforts toward Grindr. I wanted to find a local guy with a hot body. I knew it wouldn’t be easy from past experience, but maybe some new hotties moved into the area in the three months I’d been away. I started talking to one guy for quite some time. We even started to Skype with each other while I watched TV. He lived very close and had a really nice body. He was Asian, which doesn’t quite get my engine roaring so there he wasn’t a relationship prospect, but we could at least start on a friendship. We face-time chatted most of the evening. I gave him full disclosure on the situation. We even discussed him coming over to hook up, but in the end I decided to be good.

Afterall, I still hadn’t officially ended things with Smiles yet. It wouldn’t be right. I’d already betrayed that relationship once, I didn’t need to do it again, not matter how resolved I was about its end.

I got an offer from a man I’d had a tryst with in the past. He begged me to come to his apartment, but it was cold outside, and it was getting late. I had work the next day, and I needed to go to bed. I told him I’d take a rain check.

My new friend went to bed, and I continued to figure out a way to satiate my libido. I figured I would hit up some old friends in my Skype contact list. One of the sexiest men happened to be online. He lived in South America on an island, and I wanted to do bad things to his body. It was amazing. I loved camming with him. The only issue was he had a big thing for me. He always begged me to be his boyfriend, no matter how many times I told him it couldn’t happen because we are so far away. He begged me to come visit, but I told him I couldn’t afford the flight. I wasn’t about to fly to South America for a booty call. But if he lived anywhere close, I would have been over there in a second!

I convinced him to have a little fun on camera until I finished. As usual, it sapped all the energy from my body, and I jumped into bed and dozed off without a thought left in my head.

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