Posts Tagged undid my pants

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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Why Do I Make Such Poor Decisions?

Another Friday, and I used up yet another carryover vacation day. This one would kick off a staycation lasting over week long. I was beholden to no schedule and no one.

Once again, I woke up horny and turned to my go-to. I fired up Grindr and began to search for someone to satisfy the animal within. When over an hour passed by and had no luck, I turned to my computer. I checked adam4adam.com for any messages. I had a few, but no one seemed to be around for the day. I cast out a net to see what was out there. I began messaging some of the guys who lived in Hoboken and the surrounding area. Some of the guys were online, many were not.

After some time, I got some responses. I exchanged messages with a few guys, but they were all preoccupied or messaging me from work on their phone. This was turning out to be a bust, and I’d already wasted hours doing this. Geez, what was I doing with my life! But, I was still horny. Rather than turn to porn and finish myself off, I continued to search.

Then, out of the blue, a guy, who had messaged me many times before, sent me a message. He was horny and looking for fun. His profile was pretty bare, which is why I’d rejected him so many times before. However, this time I was a bit “desperate.”

I responded to his message and learned he lived close by. We talked about what he was looking for. I learned he was a “hungry bottom.” He was looking for some no-strings-attached action, and I was too. I told him to come by my place.

Half an hour later, he buzzed my apartment. When I answered the door, I was a little shocked. He was much smaller than he looked in the pictures. This is not at all what I was expecting. I don’t mean to sound racist here, only descriptive. He was a tiny little Mexican boy. He told me he was 29, but he looked about 18.

This is where I go wrong. Where I should be able to say, “Sorry. I don’t think I can do this,” I don’t because I feel bad they came all the way to my place. Why is this when the nice side of me decides to show its face?

I tell him to come in and show him to my bedroom. He immediately asks me again, “Are you clean?” I reassure him of my negative and clean status. I was a little relieved by his paranoia – It made for a stronger argument that he himself was clean and afraid of contracting something. At least I knew this guy was safe.

Warning: The following may be too graphic for some. With that, he undid my pants and began orally pleasuring me. He had a mint in his mouth, and this was certainly a new one for me. Everything tingled. I’m still not sure if this was a good thing or a bad thing. I’m also still not sure if he did it on purpose, or if he just happened to be concerned with his fresh breath.

After a short while, he turned around and began to grind his a$$ in my crotch. He asked me to get a condom and lube. He was bent over the foot of my bed while I penetrated him. He thoroughly enjoyed it. He told me to keep going until I finished. “I’m here to serve you,” he added. “I want you to finish inside me.” I wasn’t sure this was a request I could fulfill. I have enough of a problem finishing without the added hindrance of the condom’s desensitizing nature. I alternated between penetration and self stimulation to see if I could manage to finish, but it was no use. Finally, with the right combination, I ripped off the condom and finished all over his back, accidentally hitting him in the back of the head with a shot. He began to spread it around when I told him I would get him a towel. He didn’t seem to mind nor need one, but I insisted on wiping what was left of my DNA off his back. He was going to find it to be an incredibly uncomfortable ride home in the car if I didn’t.

He turned and asked if he could suck on my toes. I’d never had that request live in person before, but I was game. After my toes were thoroughly bathed, while he pleasured himself to no finish, he collected his clothes and got dressed. I saw him to the door, and with that, he was gone.

I felt so disgusting. I didn’t waste one more second before jumping in the shower. Everything I did was safe, but I still felt incredibly dirty. I needed to wash the shame down the drain as well. I found myself asking the question once again, “What the f*ck are you doing!?” I decided then and there I wasn’t going to turn this into a trend over my staycation. I was going to turn things around. This staycation was going to be all about me bettering myself. I was going to eat right, relax, read, tan, go to the gym… No more was I going to call random guys for sex. I needed to move on and stop giving myself excuses.

This was a fine plan. Now I just needed to stick to it!

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Check That Off the List

Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.

This post is embarrassing. It is now especially embarrassing because a few readers have commented about my promiscuous ways, but nonetheless, I will report the incident honestly and to my best ability. I, in no way shape or form, condone the following behavior. An early warning as well – this post will be graphic.

For some time, I’d been speaking to a few guys on Grindr who happened to be tops. When we both learned we were the same position, discussion turned to other options, such as bringing in a third. We were both really attracted to each other, but neither was willing to bottom for the other.

Many men dream about the threesome. Straight men fantasize about it constantly, and I assume it’s a big gay male fantasy as well. The only difference is gay men probably act on it and achieve it far more often. It certainly isn’t, however, easy to pull off. You have to organize three different mens’ schedules and also take into consideration their taste in other men. We all know how finicky gay men can be.

I woke up Friday with no agenda and morning wood. I wanted to take care of it, but I also wanted to act on my recent fantasy of a threesome. I started with one of the most promising guys who I’d discussed this with before. He wasn’t getting back to me. I began going through more than a few permutations trying to find 2 guys willing to participate who weren’t occupied with work.

Finally, I found one, and we both began to hunt for that elusive third. There were many roadblocks, and lots of waiting to hear back when questions were posed. I thought I had it all worked out, when one of the guys went dark on me. I was very disappointed because I thought I found the perfect combination. One top (me), one bottom, and one vers. When the bottom got a flat tire, it all went to $hit. All this juggling really made me realize why this never happened before.

After much discussion about who could host and who wouldn’t host, I managed to get my original group together, but not without issue. I had to ride my motorcycle into New York City to pick the bottom up. He wasn’t comfortable coming out to Hoboken alone, and the other guy wasn’t willing to host strangers. Strange to think he had no problem hopping into bed with strangers, just as long as it wasn’t his own. I rode in and picked him up. It was slightly awkward, but it all fell right into place. He hopped on the back of the bike, and we rode off to my place.

Warning: The following may be too graphic for some. We arrived before the other guy. I didn’t know the rules, but I was looking to wait for the vers guy to arrive before we got started. The bottom wasn’t so patient. He wasn’t the best looking man in the world, but he had a great body. He started kissing all over me until he undid my pants and started orally pleasuring me. He was quite good. He undid his pants as well and revealed a generous gift. He asked me if we could go to the bedroom until the other guy arrived. I encouraged him to wait since he was only a few blocks away.

When he arrived, the bottom walked to my bedroom and began to undress. I brought the vers guy into my room, and he and I began to undress. I wasn’t as thrilled with him. He looked much better in his pictures, but there certainly wasn’t anything wrong with him. You can’t win ‘em all. I laid on the bed in my boxer briefs while the other two joined me and began rubbing me all over and kissing me. I felt like a king. Everyone was there serving me, and it felt great!

Then the underwear was removed on all parties. There was lots of rubbing, kissing, sucking, etc. After some time, I broke out the condoms and lube. I was horny and ready to get started with the real fun. After using his poppers, the bottom was ready and eager, so I penetrated him while he orally pleasured the vers. Then the vers came to my side of the bed. We’d already discussed I wasn’t bottoming, but he thought I could be persuaded. I told him sorry, but no. I backed off and let him have a turn with the bottom.

This guy was incredibly awkward. He looked like he was having a seizure. His sex was spastic and crazy. On top of that, he was very particular and insisted I use the condoms and lube he brought. While he was inside the bottom, I climbed on top and penetrated the vers. This was not the easiest sex position by any means, and it did not last long. The logistics of three people getting the same rhythm are nearly impossible. It’s obvious in porn when this happens, they are doing it for the camera and certainly not for pleasure.

We swapped positions a few times and had already gone through a substantial amount of condoms. If one thing was certain, I was going to be wrapped up at all times! Finally, I suggested we move things to my shower.

We went through a few permutations of positions in the shower before I told them I simply wanted to watch them while I took care of myself. The bottom protested. I could tell he was very annoyed by the vers and wanted me more. When we ran out of warm water, we all toweled off. The bottom needed to excuse himself. He was feeling light-headed. He made his way out to the living room in his towel.

I was left with the spaz in my room, and I wasn’t thrilled. We tried a go at it for a short bit, but I was much more interested in the guy sitting in the living room. We stopped and moved things out to the living room after closing all the curtains. The bottom was feeling better, so he was eager for me again. He hopped on the chair and asked me to go again with him.

There was something that really turned me on watching the other two guys have sex. I pulled out and encouraged the vers to join in again. I wanted to sit on the couch and finish while I watched them. The bottom wasn’t happy about this because the vers was bad at sex. All three of us were on the couch when I finally finished on my chest. The vers reached climax as well, but the bottom seemed content with stopping before he finished.

The vers guy almost immediately began to get dressed, noting he had to get back home to finish work. The bottom was going to head back in with him so he wouldn’t get lost, but the vers wasn’t willing to wait for him to get dressed. The bottom asked me to ride him back onto the city, but I told him I would give him a ride as far as the PATH. From there on, he was on his own.

We chatted a bit about how spastic the other guy was. Neither of us were thrilled with him, but it is what it is. The bottom got dressed and hopped on the back of my motorcycle. When we got to the PATH, I gave him directions for getting back home.

I sped off home. I was in need of a serious shower. Since the morning’s activities began, I felt incredibly dirty.

If you’re considering a threesome, I strongly encourage you to think it out first. Don’t just jump into it to satisfy some great fantasy you’ve seen many times in porn. If you have the constitution for it, then by all means, do what makes you happy. But, if you’re thinking twice, I strongly suggest you leave the fantasy to your mouse clicking.

There was nothing sexy about what happened. It did not live up to the fantasy I had originally dreamed of. It was awkward and at times laborious. I needed to wash away the shame and guilt I felt, but it was no use. Those would stick around for at least the remainder of the day.

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