Posts Tagged threesome

Spring Fling

SPRING! The first day of Spring finally arrived. We didn’t have a very rough winter, but I was certainly ready for spring. I had no work obligation, so I rang in the new season from the comfort of my bed watching TV.

About 1:00 am, I got a booty call. There was a guy I had been in touch with for over a year and never met. He was a very sexy Hispanic man who it seems swam in the same circle as me. This wasn’t just any random booty call, however. He was over at a friend’s place, and they were looking to have some fun.

They didn’t want to have a threesome in the sense I’d recently been in. They were more looking to watch porn and jerk together with some light fun. Things got particularly uncomfortable when he asked if I party. I am NOT into drugs mixed with sex. It’s not my thing. I was pretty clear about this. I don’t feel comfortable around it at all. I told them if partying was in, I was out. They were fine with that. They didn’t think I was coming, but in the end I agreed to come by.

I quietly snuck out of my apartment and hopped on the motorcycle. I made my way in the chill of the night over to Jersey City where his friend lived. When I got there, I couldn’t figure out where to enter the building. I finally found it when the Hispanic guy came down to meet me. I finally got to meet him in person. He was hot and was an impressive presence. He was well-built and very tall. I shook his hand and rode the elevator up with him.

When we entered the apartment, I was greeted by a gorgeous dog. It was the Hispanic guy’s dog, and he put him in the bedroom so he wouldn’t be a bother. It was a gorgeous apartment. The owner was sprawled on the couch in front of the porn playing on the big screen TV. I was introduced and removed my jacket. I was encouraged to make myself comfortable. All three of us began to strip. I wasn’t attracted to the owner of the apartment at all. He wasn’t attractive, and he had a very distant look in his eyes. He kinda creeped me out. I had my suspicions he had already partied. He had a beer in his hand, but I had a feeling that wasn’t the culprit.

Warning: The following may be too graphic for some. The three of us laid on the couch watching porn together exciting ourselves. Then the kissing began. I started kissing the hot one while the ugly one started kissing all over my body and began orally pleasuring me. He was constantly going deeper to the point of making himself violently gag. I was petrified he was going to vomit in my lap. I tried to concentrate on the hot one. He was very normal and enjoying himself.

The ugly guy was almost like a dog on me. He kept climbing on me, and I really wanted him to go away. The Hispanic guy kept making comments about him and to him. He, however, wasn’t speaking at all, only grunting. “She’s a big old bottom,” the Hispanic said. I fully understood that by him nudging his hairy a$$ toward me constantly, but I was not interested. He wanted me to penetrate him, but I was not going anywhere near that, even with a condom on. I was cordial to him, but I never purposely engaged him in any way. He kept getting in the way of me enjoying time with the hot one, whimpering by my face waiting to suck on my mouth.

A few times I contemplated leaving. I never did anything I wasn’t comfortable with, but I wasn’t really enjoying myself. Periodically, the porn would freeze to buffer, and the “dog” would have to fix it. It was a nice reprieve from him being all over me.

After some time, the hot one decided it was time for him to head home. He needed to get the real dog back and settle in for the night. If he wasn’t staying, neither was I. I stood and told them I was heading out as well. I started to get dressed. The ugly dog on the couch was confused by all this and still in a haze. The Hispanic guy asked if the other guy could give him a ride home. After some confusion, he agreed. I was very happy I wasn’t in that car. I wasn’t sure he’d be ok to drive. I waited for the other two to finish getting ready and dressed to head out.

The Hispanic with the dog told us he needed to go downstairs to let the dog relieve itself. I wasn’t thrilled with the idea of being left in the apartment with just him. I stood by the door, and the other guy got ready quickly. We ended up all riding down in the elevator together. When we got downstairs, we all said goodbye. I hopped back on the motorcycle, sped home and hopped in the shower.

When I got back to my apartment, I got a text from the Hispanic guy. “Sorry. I think my friend was into you. I felt kinda out-of-place. LOL.” I responded back after I got out of the shower, “Hey dude. Great body. Seem fun. No offense, but your friend isn’t really my speed. Sorry. Not sure if you had fun with me, but feel free to hit me up sometime.” That’s when I got the full story between the two of them: “Him and I hooked up when we first met and no more after that. Sorry if I came off rude. I had fun with you. Definitely. But, he was trying to have you for himself. I got the hint. He’s my bud, so I was trying not to f*ck it up. I wasn’t sure if you were into him or not. You were kissing each other. Plus I had my pup with me.” I explained to him the confusion: “I was more just letting him play. Didn’t want anyone to feel left out. LOL. I was trying to get more of you ;)” He told me, “I would chill again whenever.” I quickly responded, “Cool dude. You have my number. Anytime. Trying to go on a Grindr diet… Obviously failed tonight.” He finally added, “It’s cool. Had fun. Finish some other time. ;)” With that, I hopped into bed.

I finished myself off and passed out. I didn’t set an alarm since I had nothing to wake up for early in the morning. This post should have been titled I have no willpower. Hopefully the next day I would be able to stick to my new diet.

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Chelsea Comes to Hoboken

My Friday off was certainly an eventful one. I spent the better portion of the afternoon planning and participating in my first real threesome. I was already starting to judge myself and question all my recent behavior. A large part of me knew this was not who I was. I was completely acting out, but another part of me realized these were my gay “formidable years.” I never hooked up with guys in college while all my male friends were taking girls home from the bar. This was my wild time. Basically, I was giving myself license to have emotionless sex for sport.

That being said, I was still searching for the guy who would get me off Grindr and be the reason to settle down. I’d already gone on one good date with Chelsea. He asked what my plans were for the evening. I told him I had none since I had the day off, and he asked if we could do something together. I didn’t feel like doing anything crazy or going out, so I requested a lazy night in and suggested he come to my place. “Cuddle night?” he replied. “Definitely,” I said.

I still felt a little disgusted with myself for my afternoon behavior, but I also hoped maybe he could help distract me. He would certainly be something to get my mind off it. I took all my sheets off my bed and threw them in the washing machine. I hopped in the shower once again. I needed a cleanse.

I texted him back and told him I would make us dinner, and we could watch a movie. He agreed that sounded like a great idea, but he told me he’d already eaten. I made myself something quick before he came over.

“Do I have to come back to NYC late by myself?” he added. I told him he could certainly spend the night. In fact, I would very much enjoy that. He tried to convince me to come into the city, but I wasn’t about to budge. I’d already done one date in his neighborhood. I didn’t want to go into the city that evening since I wasn’t already there for work. He painted a better picture of what I was asking him to do: “Mind you, I don’t even go see my friends in Brooklyn. So this better be scoring me some hefty points! Haha! LMAO. You can ask my friends how much of a NYC snob I am. I’m like who? What? Why? Do I need a passport? And does Jet Blue fly there?” I quickly responded, “This isn’t my first rodeo. You’re not the first guy I’ve stolen out of the city.” Every guy I’ve convinced to come over to Hoboken has fallen in love with it and become an advocate. I am slowly introducing the NYC gay community to the great city of Hoboken one gay at a time :).

He agreed to stay over, as long as we agreed to behave. I told him I had no problem with that, and I appreciated him wanting to take things slow. I was very surprised by this, considering we met on Grindr, and I learned he’d done the hookup thing more than a handful of times.

When he arrived, I got him some comfortable clothes to wear, and we settled in on the couch with a few refreshments. We went through the guide trying to find a movie to watch. Finally, we settled on Drive, with Ryan Gosling. We laid on the couch with him in my arms the entire film. It was nice to snuggle with a man. It was very romantic. We both thoroughly enjoyed the movie, and when it was over, it was decently late. We decided to head to bed.

I found it adorable he didn’t take his shorts and shirt off when we went to bed. I don’t exactly sleep naked, but I have a hard time sleeping with clothes on. I find them restricting. I stripped down to my boxer briefs and encouraged (playfully removed the shorts I lent him) him to get comfortable before spooning with him a little. He warned me about getting too fresh, but I told him to relax. “I’m just trying to cuddle, not rape you. Stop fussing,” I jokingly stated. He did relax, and we got into a comfortable spooning position before finally dozing off for the night.

That night, neither of us slept very well. He was a thrasher and constantly woke up. I didn’t mind too much because I didn’t have anything to do the next day but lounge around. It was nice change to be sharing my bed with such a sweet guy. This had potential, and we certainly weren’t rushing things…

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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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Is This A Porn Shoot?

After meeting the ginger, I was talking to a very attractive resident of Martha’s Vineyard who is originally from Russia. He is very attractive and very sexual. I attempted to invite him to meet us at the beach or come out with us to the bar for two straight nights, but he declined every time.

Instead, while out to dinner one night before hitting the bar scene, I came across a guy on Grindr who happened to be at the same restaurant. He seemed nice enough. When we finished our meal, I walked up to the bar to meet him and introduce myself. My friends weren’t far behind. It took all of three seconds to realize I would not be interested in this man from New York City.

As soon as he opened his mouth, it was quite evident he was a big ol’ mo. He is a 6’4″ ball of flaming queen. I couldn’t get out of there soon enough. Of course, I was too polite to simply walk away, and we exchanged numbers. And, just my luck, he was heading to the same bar my friends and I were going to. I did my best to hustle my group along except one of my friends stepped in to “help me out.” She didn’t quite realize how uninterested I was in this guy.

Our group split, and half of us went to the bar — The other half went home to bed. The Grindr guy and his straight friends followed shortly behind us. All the straight guys began hitting on the girls with me. I put a pylon between the Grindr guy and I so I wouldn’t have to engage him on conversation further. He started to chat with one of my female friends while I stood in the background and made myself as unattractive as possible. My friends and I were trying to see who could look more pregnant. Classy, I know. When we all finished our one beer, we moved on, but not before Grindr Guy grabbed me and tried to plan a beach trip for the following day. He was going to text me where they were, and we were expected to join them. That never happened.

So, just when I didn’t think I could dive any deeper into casual sex, I come to surprise even myself. The following morning, I was chatting with a good looking guy from Boston who was very discreet and had a girlfriend. He was looking for some action. I was only half interested. I was still trying to make things happen with the Russian. We were heavily flirting and exchanging pictures. He asked if I found any other hot guys on the island. I replied, “I’ve yet to see any serious talent since I’ve arrived.” I wasn’t about to share the Russian with him. That’s all I needed was for him to scoop him out from under me. He was very interested in me, but explained he was already making plans with another guy to have some fun in the woods.

At that point, he proposed the three of us get together. I didn’t know how to react. He already established he was not interested in sex but was looking just to fool around — “circle jerk” as he put it. I cautiously agreed to participate but needed more specifics before I would feel completely comfortable. At that moment, the Russian started responding.

I tried to see if he was interested in meeting up that morning instead of the party in the woods. I would go for a run to his place and spend some time there before anyone was even out of bed. That’s when I found out he was going to be the third party in the circle jerk. It’s also when the guy with the girlfriend started scolding me for trying to steal the Russian away from him. I explained I had been talking to him for some time. He of course called me on my earlier comment about the island’s lack of talent. It was slightly awkward, but we got passed it.

I learned the other two had already chosen a spot in the woods to meet. It happened to be 3.5 miles from where I was staying. I also learned I had slightly less than a half hour to get there. I threw on shorts, shoes,  popped in my iPod and took off towards the site. I arrived shortly after the other two. The spot they chose was a construction site in the middle of the woods. It looked like a giant sinkhole.

When we all gathered, we tried to find a place to get out of site. I vetoed the original plan of walking into the woods, namely because I didn’t want to spend the rest of my vacation covered in poison ivy rashes. In the center of this hole in the ground were construction vehicles. Although they were the center of attention from all sides of the site, we managed to duck between them and get out of site.

(Just a warning, the following may get graphic) Almost immediately, the other two dropped their shorts to their ankles and began to jerk off. I followed suit. Every began to participate and aid each other in different combinations between the three of us. I was dripping with sweat from my long sprint, which surprisingly was a turn on for the other two. It brought me a little more attention as well. This was the first time I participated in anything with more than one other, so I was slightly intimidated. However, it was easier to relax a bit because I knew it wasn’t going to escalate to penetration. We all had our fun and eventually finished ourselves off in succession. I was on quite a high. Between hooking up in public, doing it with two guys, the run, and climaxing, I was in a different world. I had no idea how I was going to make the run back home. My legs were weak.

We decided it wasn’t a good idea to linger, especially the paranoid guy who had a girlfriend. He split off and the Russian and I casually walked back to the highway. He offered to give me a ride, and I graciously accepted. This would also help cut down on the time I was away. We had casual conversation the whole way back about our inability to connect with just the two of us earlier in the week and the other guy’s situation playing both sides of the fence. He dropped me near the house I was staying at, and we agreed to touch base later about hanging out.

I ran back to the house and hopped right in the shower. While I stood in the shower, I thought back on the morning’s events. It played out like a Sean Cody gay porn. The only thing missing were cameras. Everyone was just waking up and getting ready for the day. It wasn’t even the weekend yet, and I already had my first ginger and my first three-some. Who knew what the rest of the trip would bring. Only time would tell…

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2 Can Play That Game

N and I were talking sporadically, but it was almost as if we weren’t in a relationship. He was working in the city that day, and sent me a text message asking what time I was heading in. I was getting in the habit of waking up and getting to work earlier. I still didn’t have my appetite and wasn’t eating breakfast in the morning, which bought me more time. I was also enjoying the distraction of work that kept me busy. I told him I would be heading in at 8:30. He said he wouldn’t be ready by then. I didn’t have to be in at a set time, so I waited for him.

Finally, at 9:15 he emerged from his apartment. Had I known he would take so long, I would not have waited, especially if I knew what was to follow. The conversation on the walk was very distant and awkward. We spoke as if we were already broken up. Most of the time, he was buried in his phone. Maybe he was on Grindr, but at this point, I didn’t care. I was too, and I was getting bites. When we were half way to the PATH, he pulls back and says, “Wait! This is telling me the bus is a better option for me to get to work.” Apparently we wouldn’t be going into to work together after all. I waited around for an awkward five-minute walk. He mentioned his need to stop at the ATM but would also needed exact change. Since I’m the overly generous person I am, opened my wallet and handed him a bus pass. He commented, “You would have this in your wallet.” Not even a thank you. I felt like one of his discarded used tissues. I allowed him to take advantage of my generosity, and I hated myself for it.

Before we headed our separate ways, he told me he was going to watch the fireworks with his family at his aunt’s house that night and would probably be staying there. We would not see each other that night. 

While watching TV on the couch, I began to get horny. I decided to text the man I had sex with a few weeks earlier. He was a good lay, and I figured why not? I texted, “Hey man. Wanna come over?” He responded pretty quickly. He was out with friends but would stop by later. He added, “I not a whore or anything either, but I had fun last time with you.”

This is also the exact moment N texted me asking what I was up to because he was on his way back from his aunt’s house. In my passive aggressiveness, I told him watching a movie and chatting online. In the meantime, I texted the man from Grindr and informed him I would have to cancel and apologized. I got no response from N, so I asked if he was just checking up on me or if he was interested in hanging out. When N replied telling me he was just checking up on me, I immediately texted Mr. Grindr and told him to get his ass to my place and apologized for the confusion.

When he arrived, we went out to the balcony to hang out for a little bit and smoke. At this point, he started asking a lot of questions about N. When I asked him “What gives?” he explained someone meeting many of my descriptors had been texting him for some time now. He spoke up because when we met the first time, I was upfront and told him I was involved with someone. At this point, he offered to show me the messages he received. It was really none of my business what the exchanges were between them, but I graciously accepted the offer. What I saw next was just the dose of reality I needed. N had been asking this guy to hook up many times, even sending him pictures of his dick (with his face in the shot). So much for just talking! The icing on the cake was he was messaging him that night. He was playing back n forth between the two of us. That was the ultimate slap in the face. While he was sitting there in front of me, N was still texting him. 

I knew better than to leave notifications on my phone when Mr. Grindr came over. I had a feeling N would text again, and I didn’t need a distraction. I was horny and was annoyed with N’s games. Mr. Grindr and I had an extensive conversation about the situation at hand. I apologized profusely for bringing him into the mess and came clean about using him just for sex. He actually was a good guy and I started to look at him as more of a friend than just a hookup. He didn’t need to tell me about N’s sexting, but he did. I greatly appreciated his candor.

With that, we headed inside to my bedroom. As we did, I glanced at my phone. I had three text messages from N asking if I was feeling better, asking how my chatting was going, and finally asking again what I was doing. Mr. Grindr looked at me and asked if it was N. I said yes as I put the phone down and lunged at him.

We had sex and it was good, but we needed to take a break. When we did, we discussed things again, but the conversation was more about the relationship between he and I, not involving N. He even asked, “Should I tell him to come over?” I loudly protested how bad an idea that was. I don’t know if he meant in the sense of a three-some, but I thought me meant more to confront him on his indiscretions. I told him it wasn’t my style to make a public spectacle of things. That type of action was not proper, not matter how much N was playing games.

At that very moment, Mr. Grindr got a text notification. He said, “That’s one of two people. Either my roommate or him.” I told him he didn’t need to look for me, but if he wanted to look for himself, that was his business. He looked, and sure enough, it was N asking him to hang out still. I got GREAT satisfaction out of this. Not only was N home alone with just his hand, but after trying to manipulate both of us, I got the guy. The two of them never had the opportunity to meet. Both were closeted and had roommates. They had nowhere “safe” to hookup.

Mr. Grindr’s morals kicked in at this point, and he decided it best if he went home. I tried to convince him to stay and chat further (and also finish what we started), but it was no use. He insisted on leaving. If I wasn’t feeling guilty enough for dragging him into this mess, now I felt downright awful. As he left, I walked to the window to watch what he did. I was curious if he was going to try to meet N. He walked to the corner of my street, looked at his phone, and looked toward N’s apartment. He paused a moment as I said out loud to myself, “Don’t you dare!” Just then, he turned and walked home. “Good boy!” 

After about a half hour, I responded to N’s texts. I told him my appetite was returning and the online chatting was just Facebook. I then played dumb and followed up with, “Did you need something?”

The next morning I woke up to a text from N saying, “I wanted to see you.” What a prick! He didn’t want to see me. He wanted to get off! And, he didn’t care if it was Mr. Grindr or I. This cut deep, but my anger provided a sufficient band-aid for the time being. To me, it was his worst transgression. Even if they never met, he had every intent to do so. He even went as far as covering his bases by texting me should their plans fall through again. It was over. We were done. I do not stand for anyone treating me this way. After 26 years of single life and tormenting myself, I wouldn’t stand for this behavior! I deserve better! This was the wake-up call I needed, but this was just the beginning of my transformation back to my old self.

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