My First Grindr Hooup

I had slowly been working up my courage on Grindr. At first just lurking with a blank profile. Then adding my stats: male, 20, 5'8", 145. Then adding a bio: sub bottom looking for right now. Then adding butt and body pics.

So far I had chickened out at each stage. Ghosting people who messaged me. Ghosting people who asked for pics. Ghosting people who asked for face pics. Ghosting people who sent me their location. I would flake, and then get frustrated that I flaked. Over and over.

Until one night I found a profile of a couple looking for a bottom. Both were fit guys in their 40s. Their bio said they were a happy couple, both tops, who occasionally like to rent a hotel room and find a nice bottom to fuck. If this had been my first time on Grindr, I would have simply admired from afar, fantasized about a hookup, jacked off, and called it a night.

But I was tired of my constant backing out. And my roommate was out of town, so I wouldn't have to make up some story about where I was going. And downtown, where their hotel was likely to be, was within walking distance to me. Stress from school had me so worked up I was ready to burst. I knew I really wanted this. I needed this. So I decided that I would cross any barriers necessary and finally make this happen.

We messaged back and forth. I sent them my artfully crafted thirst trap pictures proving that I deserved the "bubblebutt" tag. Both of them were surprisingly tall and muscular. Just seeing their shirtless pics made my skin and face flush. They asked for a face pic. Something I never sent before. But I had made the decision.

Of course, for them, it was no big deal. They simply messaged 'handsome' and eventually sent me a location and a time. 'One of us will meet you in the lobby at 9:30pm.'

It was only 7:30pm when I got that message. Two hours to kill. Two hours to let my horniness simmer. I tried to distract myself with tv and video games, but my eyes kept drifting toward the time and my mind kept imagining the possibilities. So I spent too much time preparing, using my douche and riding my dildo. The hardest part was not touching my dick. I knew that if I masturbated and came, I would lose all motivation and bail out yet again.

Eventually, it got to 9:00pm, so I walked out of my apartment with a little backpack full of condoms and lube. It was a nice night and I made it to the hotel at 9:15pm. Instead of awkwardly sitting in the lobby, I walked around a bit more. I thought it would relax me, but it just filled me with even more anticipation. I was almost shaking when I finally decided to push my way through the lobby at 9:31pm.

It was empty. I looked around and accidentally made eye contact with a receptionist.

"Can I help you?" she asked.

No thanks, I thought, I'm just here to get railed by two men twice my age, thanks.

I managed an articulate "Uhhh", when, thankfully, one of the men walked out of the elevator, saw me, and waved me over. He was tall, dark skinned, and had a big smile and an energetic demeanor. He motioned toward the hotel bar.

"Can I get you a drink?" He asked.

"Oh, well, I mean I would like that, but..."

"Right, of course. Should we just head up then?"

I nodded. We waited in the elevator. When it came it was empty and he motioned me to go first. I did and he gave me a quick tap on the butt. That shocked me stiff, in more ways than one.

When the elevator started moving up, he told me to relax and rubbed my shoulders lightly. It was probably pretty obvious that I was inexperienced. I tried my best to calm down, but his strong hands made my heart race.

We made it to his floor and he showed me to his room. Inside, his partner was sitting on the bed. He was a little shorter, a little stouter, and with light skin. He seemed glad to see me.

I was surprised by how fast everything started. I don't know what I expected. A drink, maybe. Chit-chat for a bit, perhaps. But no. They simply led me to the middle of the hotel room and then, instantly it seemed, I was overwhelmed by four hands feeling my body and two mouths kissing me all over and whispering in my ear. They stripped me down right away and took turns feeling me up and admiring me. One of them even insisted that I spin and twirl and pose for him. They were both still fully clothed which made me feel kind of silly but I was so utterly turned on I would have done anything at that moment. So I did my best to seem like a supple, sexy, boy toy for them.

They then had me lay down on the bed. One of them started making out with me hard, while the other started eating me out. They were both so big and muscular and aggressive, but also patient and considerate at the same time. A lot of "does that feel good?", "do you like that?", "is that ok?" I could only muster little groans and "mhmms" in response. I felt simultaneously overstimulated and secure.

Finally, they got off of the bed and started to disrobe. They were even more muscular than in the pictures. Both of them wore thongs with equally impressive bulges. One of them indicated that it was my job to remove their underwear, so I did what I was told and got on my knees in front of them. I did my best to slide the underwear off in a tantalizing, seductive way (though I probably failed). When I pulled the first thong down, I could not believe the size of the monster was packed into that thong. My eyes must have been fully wide open when I looked up at the taller guy.

"I was surprised you didn't ask how big it was," he said. He was right. I didn't ask for dick pics. I didn't even ask how big their dicks were. From some pictures, I could guess that they were packing, but I didn't realize how big. The second guy decided not to wait for me and pulled down his thong to reveal a dick even thicker and nearly as long.

I didn't have much time to process this before I had hands gripping my hair and dick deep in my throat. They made out with each other while both of their dicks were in my face. They took turns using my mouth and throat for a few minutes before one of them picked me up and put me on the bed. When I was bent over in doggy position on the bed, one of them had me continue giving him a blowjob while the other prepared my ass. He lubed me up and started fingering me. Just two fingers had me shivering and tensing.

They asked if I was ok and if I was good to continue. I said yes, of course, though it probably came out more like begging than like giving permission. Then the shorter one put on a bright red condom, lubed up, and slowly started to press against my asshole.

I was still blowing the taller guy, but my mind was spinning with the image of the giant dick at the precipice of entering me. The moment he broke the barrier, I gasped hard. The taller one moved his body so that my smooth chest was against his broad one. He kissed my neck and whispered reassuring words as I tried to relax. The shorter guy was very patiently going slightly deeper with gentle, careful shrugs. The taller man beneath me grabbed my hair. I heard things like "That's right", "Relax", "You're doing so good", "Good boy", "Yes, babe, just like that", as the man behind me kept thrusting deeper and deeper.

And deeper. The muscles in my chest and arm flexed hard. My shyness and timidity had so far repressed any significant groans or yells, but a particularly deep thrust made me squeal with pleasure. Though it may have sounded like a cry of pain, since the thrusting stopped and they both asked if I was ok.

"Yes! Yes! I'm great! Please keep going!" I said. Probably too loud and too enthusiastic. But I was finally here. A fantasy I had had since the hormones of puberty were released into my body and my brain designated boys as the kinds of humans to be sexually desired.

The thrusting slowly returned and steadily ramped up. Each deep thrust brought with it a wave of pleasure. Each deep thrust broke down a wall of inhibitions. I started groaning louder and louder. Moaning gibberish. Begging incoherently.

This thrusting, with encouragement from his partner, loosened my ass and turned my brain to mush. The taller man decided that it was his turn. He lay down on his back, with his huge cock erect, wrapped, and awaiting me. My legs and arms were shaking as I stumbled my way into position, with help from the shorter man. I straddled the monster cock and the two of them both held me and eased me down. I was so loose and ready that it was only a few seconds before I was able to sit with his entire cock in my ass. He then wrapped his arms under mine and grabbed my shoulders.

I felt totally under his control as he drove his hips into me. He slowly increased the pace, but kept a smooth rhythm. My moaning grew louder and louder. It felt like my entire body was sizzling and sparking from being overloaded with pleasure. His grunts and groans and moans were driving me crazy. Without breaking rhythm, he told me to get ready. "I'm going to fuck you hard and cum," he said. I thought to myself, yes, please, please cum for me! I tried to say it as well, but his hard fucking had apparently overloaded my brain and I only managed to moan incoherent nonsense. His final flurry of huge, hard thrusts sent me over the edge. Half the hotel must have heard my screams. With one final thrust, he drove himself into me, and gripped me so hard my shoulders were bruised the next day. I felt utterly, totally fucked, and on top of the world. By the time he loosened his grip, my body was as rigid as a ragdoll. He moved me into a position where I was laying against him.

Then the other guy moved into position. He raised my legs over his shoulders and slowly slid his thick dick into me. At this moment I felt so utterly used. One muscular man held me in place while I was properly fucked my another. Mere moments after I thought I had felt the pinnacle of pleasure, I was proved wrong. I felt like I could barely stay conscious with all the pleasurable sensations being pumped into my brain.

Then an entire new feeling hit me. It started as just a small tingle nowhere in particular. Then it felt like it was weaving its way through my whole body until it reached my dick. My dick, small, flaccid and flopping in rhythm with the thrusts of a dominating man, started feeling so good. So, so good. Shockwaves started running through my body. My brain was overloaded. Completely cooked. I could barely process anything. Then I realized what was happening. Oh my god, oh my god, oh my god, I thought. I tried to yell out, but only moaned. I tried again, but just gasped and squealed. Finally, I was able to get a sentence out.

"You're gonna fuck the cum out of me!" I yelled.

When I yelled that, I first saw surprise on his face. Then eagerness. He started ramming me harder. "Yeah, yeah," he said, "Cum for me little boy."

With that, I lost voluntary control of my body. His hard thrusts would have launched me off of the bed if not for the other man holding me in place. I emitted a final, long groan as ropes of cum flew from my penis. My dick was flopping so much from the hard fucking that cum flew in all directions. It was all over my body and I could feel some hitting my face. And it just kept coming out. I had never cum so much. Right when it felt like all the cum was finally out of me, he grabbed me hard and hit with a final deep thrust. He pressed his hips hard into me and I felt folded in half. Squeezed between the two men who had both fucked me until they came.

After he took his dick out of me I felt empty. And dizzy. The two of them got off of the bed. I went to move, but my legs felt like jelly. I simply rolled over onto my stomach.

"How do you feel?" one of them asked.

I mumbled something unintelligible.

"That good, huh?"

"Amazing," I managed to say.

I felt a firm slap on my ass. The two of them started talking to each other, but I don't know what they said. Their voices were already fading. My mind was barely attached to the physical plane. And I let my brain succumb to sleep.

I'm not sure how long I was out -- probably only a few minutes -- before one of them politely nudged me awake. He asked if I wanted to take a shower. I told him yes. Luckily, the shower was big enough for the three of us, so we showered together.

I wish they would have invited me to stay over. I wanted to fall asleep nuzzled in between those two beautiful men. But, while this had been the best night of my life, they had probably had dozens of nights just like this one. So, after a couple of goodbye kisses and ass pats, they sent me on my merry way. Though I tried to act normal on my walk home, I expect that my face was beaming.