Tales of a Chronic Premature Cummer

"I'm going to fuck you hard and deep until you're begging me to stop." I pressed send on the message and watched it go from sent to delivered to read.

"Oh fuck yes! When can you come over?" That's what he sent back to me.

We had been talking on Grindr for barely twenty minutes when the conversation slipped into sex. He was the one to bring it up first. God was he cute, at least based on his profile pic and the ones he sent me. He was apparently 5'3" tall, weighed 125 lbs, considered himself a twink, was on PrEP, and loved bareback sex. I was on PrEP as well, but I also I preferred using condoms. I mean I think sex feels better without them, who doesn't? Nothing beats the feeling of sliding raw in a tight hole, but the condoms made me last longer, which is something I desperately needed.

"I need to shower first then I can come over and give you the fuck of the decade." God, why did I play it up so much? I have never once given anyone the fuck of the decade, let alone the fuck of the week. Every time I've been with a guy, it was over almost as soon as it began.

For a while, I thought I just wasn't cut out to be a top and switched to bottoming, but that only seemed to exacerbate the issue. When I was topping with a condom, I could hold onto my jizz for at least a minute, maybe two, but when I was being fucked, with that pressure on my prostate, I would cum without even being touched in barely 30 seconds. And once I came, bottoming started to hurt way to much to continue.

"I'll be waiting." He then sent me his address, "Here's something to think about when you're in the shower. 😈"

A pic popped up on my screen; it was a POV shot of him being fucked from the perspective of the top. I could see his entire body tensed in pleasure, every muscle was exposed. His legs were elevated and you could see the base of the thick cock that was fucking him. He had a look of utter ecstasy on his face.

I felt myself immediately get rock hard, and the fabric of my trunks pressed against my cock, which was enough to cause a spurt of precum to stain my Calvin's. Fuck. What did I just get myself into?

"Wow. That's hot!"

"Thanks. This guy's got a great dick. Nice and thick and long, at least 9 inches. Biggest I'd ever taken."

Well, there was another thing I had to be nervous about now; he'd been fucked by at least one really big dick before. I wasn't small by but I did not measure 9 inches.

I didn't know how to respond to that, so I just typed, "Jesus."

"Lol. Yeah it was big. What can I say? I like big dicks." A few seconds passed before he sent this, "How big are you exactly?"

"I don't know." That wasn't true; like every other guy, I've measured my junk, "Like 6.5 inches." Maybe on my best day.

"Oh ok. That's fine. That'll get me there. Plus your super sexy; that always helps. Lol"

"Ok good. I'm going to go jump in the shower now. I'll text you when I'm on my way."

"Great! See you soon!"

I stood up from my bed and headed into the bathroom. I disrobed and stared at myself. I guess I was kinda sexy. Not tall but not short, about 5'9". I had a decent body; it was obvious I worked out. Wavey brown hair, blue eyes, symmetrical face. Now if only I didn't cum faster than a teenager on prom night. I stared down at my dick and he stared back up at me. It was at full mast, with a drop of precum leaking out of the top, "are you going to cooperate with me today?" Probably not.

I walked over to the shower and switched it on. My cock was still rock hard. I should probably jerk off, right? Get that initial nut out of me; maybe that would alleviate the sense of urgency my cock seemed to have.

I stood over my phone and opened Grindr again. I pulled up that hot pic he sent to me. God he was so sexy. I gripped my cock and imagined myself as the big dick top that was inside him. I started slowly moving my hand along the length of my shaft.

I could almost feel the sensation of sliding into him. The feeling of that tight little hole wrapping itself around the head of my dick. The pressure of sliding in and the release of getting passed that first ring of muscle.

My hand had involuntarily started to move faster thinking about how warm and wet his hole would be. I could hear his moans as I started to pump my dick in and out of him.

The cum had already started rising up and I was right at the point of no return. My breath had become ragged and my arm was moving frantically at this point. And just as my passion was reaching its peak, I released. Spurt after spurt of long thick cum ropes shot straight up, some even hitting my face. I let the euphoria of the ejaculation wash over me as I began to regulate my breathing.

Wow, I was covered in cum, as was my phone, the counter and floor. Shit. I really needed that.

I ran a towel across myself and my surroundings to try and soak up all my jizz. I had cum so much.

It would have felt so much better to have shot that inside him, but hopefully masturbating before hand would make for a better fuck session.

I threw the towel into the laundry pile and stepped into the warm water of the shower.

After drying off and throwing on some clothes, I messaged him, "on my way."

"Great! Can't wait for that cock to be inside me."

I was hard again just at the thought. Fuck. I was really banking on that masturbatory cum here.

I got to his apartment, parked my car and opened Grindr, "I'm here."

It was a twenty minute drive to his place and I was hard the entire time, and no matter how much I tried willing myself to think of something else, my mind kept going back to that super hot pic of him getting fucked. I had switched into a pair of Andrew Christian briefs and this poor pair was almost filled with precum at this point. A small wet spot had even started to form on my jeans, right at the end of the visible penis line poking through them.

"Great! Don't knock. My dog hates it. Let me put her away real quick. Hang tight." He then sent me his apartment number and told me, "come on up. The door's unlocked. Just let yourself in. I'll be naked, face down, ass up on the bed." And with that message came another pic. A selfie of him taken with his face looking up; the camera was positioned high above his head so you could see his entire exposed back in the perfect "fuck me" arch and his bare ass was in the air.

My dick leapt at the photo, rubbing against the wet stain, causing more precum to be released.

Fuck, I was turned on.

I stepped out of the car and headed up to his apartment.

The door was unlocked like he had said; it was a nice place actually. White walls, black doors, and well furnished. Guy had taste.

I turned a corner and there he was, ass up. I couldn't see his face but his body looked just as good as his pics.

"Wow your ass looks phenomenal." My dick was aching to be freed now.

"Thanks." He turned his head around and faced me. Yup it also matched the pics. Fuck this man was gorgeous. "Now get over here and fuck it!"

I took a big breath and headed toward him, throwing my shirt and slipping my shoes off along the way. I was situated right behind him when I dropped my jeans and got my first look at just how thoroughly drenched my underwear was in precum. I got out of those as well and my dick sprang free, hard as a rock. My dick head slid across the smooth skin of his ass and the sensation nearly sent me over the edge. I already knew this was going to be a very quick fuck, even for me. I could feel my skin burning red from embarrassment just at the thought of how humiliating it's going to be.

I decided to prolong this experience as much as I could. I knelt down, my face centered right behind that perfect ass! I spread his cheeks with one hand and reached around to his member. It was smaller than mine, maybe five inches or less, which made me feel a bit better about my size. I leaned in and slowly started to lick his hole while simultaneously sliding my hand along his shaft. I was tentative at first, everyone had a different level of sensitivity when it came to rimming and I didn't want to jump straight to the rough stuff. I got a bit more aggressive with it when I heard a small "fuck yes," escape his lips. At least I could do something right.

He tasted great and the longer I was rimming him, the more aggressive I was being with his hole, soft bits, slapping his ass, all while jerking him fast and faster; he moaned and groaned and occasionally screamed "fuck yes!" I was getting very carried away in this process, and I was loving every minute of being between his cheeks.

It went by almost unnoticed but my cock was twitching and leaking, getting harder and harder, as I was tonguing him. I finally realized how much it was aching and how rigid it had become when he pulled my hand off of his cock and said, "I need you inside me ...now!"

I let out a sigh; I knew what was about to happen. It had happened so many times before. I stood up, positioned my cock against his puckered pink hole, and then I slid my thumb in first. "Fuck man! You're incredibly tight! Let me just... there it is.", I had found his prostate and started to gently massage it.

"Oh god! Oh fuuuuuuuuuck!!" His breathing was becoming more erratic; I was clearly doing something to him that he liked. I spent a few minutes playing this game, adding a finger then another, "Get. Your. Cock. Inside me!"

Well, no more delaying it; I pulled out my fingers and asked, "Where are the condoms?"

"No. No no. Please. I want to feel u inside me, nothing between us. Please."

God damn!

I pressed my dick in. There was some resistance at first, but I heard him let out a moan and everything loosened up. The head of my cock was now through, and I could feel it throbbing from the tightness. I took a moment to try to compose myself and extend this experience.

Without any warning, he pushed back and my entire cock was suddenly inside him. He felt amazing. Better than I could have ever imagined, but with that one simple motion, I was at the edge of no return.

A groan escaped my mouth as I tightened every muscle, trying my hardest to hold back.

No no. Not this time. Hold out. Come on. Not this time.

It was too late though. There was no stopping it now, "I'm sorry."

And as I relaxed, a tsunami of ecstasy washed over me; it was the best orgasm I had experienced in months. And it took only 3 seconds to achieve. I felt myself filling up his hole, spurt after spurt.

I fell on top of him as I came, and spent the next few seconds just trying to catch my breath; my cock was already starting to grow soft.

God this was just as humiliating as I thought it would be. What a fucking loser!

"Well, I don't know whether to be turned on or offended."

"Fuck I'm so sorry." I stood back up and my dick slipped out of him, and a deluge of cum followed after, "shit!"

"God damn it! You came so much." He reached behind and tried to catch as much of it as he could and made a b-line to his bathroom without saying another word.

"I...I guess I'll just get going!" I started gathering up my clothes. I really wanted nothing more than to leave and block him and never think about this day again!

He was back in his bedroom now, "Wait! Wait! Say, in like a half hour, would u be able to go again?"

"Probably. You're willing to try again?"

"Sure. But I have another guy that wanted to come over today; not as sexy as you of course but definitely hot. Do you like groups?"