The Big Dick Bet that Backfired

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Ağu 7, 2022 // By:analsex // No Comment

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I accepted a biggest dick bet online and things got a little out of hand. The moral of the story: Think twice before you enter a big dick competition.

Last month I found myself in another predicament. Once again, it was my own fault, but what happened was both exciting and unnerving.

It was a Friday afternoon, and the sun was shining bright into my office window as 4pm came and went. This is a quiet time for my workplace, so most of my colleagues had already slipped out of the office and headed home. After a full day of work, my brain was pretty fried, but for some reason I wasn’t eager to sit in traffic. So I pulled out my phone, made sure it was off the company network, and pulled up the local personals website. I’m never sure what I’ll find when I do this, or just what my intentions are. 99% of the time I’m just a voyeur, browsing these posts to see if any of them involve real people like me.

Most days, the list is full of prostitutes and trolls. Once you sort out the professionals, you are typically left with old men looking for young men (or ANY men), and all the guys seem to want to bend over or blow someone. That is par for the course, but sometimes there are diamonds in the rough. On this particular day, after about a half-hour of browsing, I wasn’t finding much. I was about to shut it down and grab my car keys when I hit the refresh button on my phone’s browser. I don’t know why, but I do that sometimes. I think my greatest rush is when I see someone who just posted, and they are not a pro or a troll. Someone who is having a horny moment, like me, and has decided to reach out to see what happens.

The phone’s browser spun its wheels for a few seconds, and then refreshed the page. About three posts from the top was a new post that caught my eye. “Big Dick Contest” was the title. There was no picture for this post, but the location was right near my work, so I clicked on it with curiosity.

The post popped up right away, and suddenly I had a lump in my throat. It read,

“Who would like to drop by and jerk off? I like to show off my cock to another dude, talk about pussy, compare dicks see who’s bigger, talk junk – just dude stuff on the down low. Must be masculine, straight or bi guys only. I’m tall, late 40s, athletic, friendly, straight but open-minded, kinky. Send age, location, basic info (height, weight), face picture preferred. How about a big dick contest? Biggest dick wins a prize. What should the prize be?”

Now, let me pause for a moment to describe myself. I’m a professional, normal, guy-next-door kind of guy. Happily married, attractive, in decent shape, with a nice dick. I’d say it is a good seven inches with great proportions and a nice thick head. No complaints about size, but I won’t crack anyone open either, if you know what I mean.

Every once in a blue moon, I like to wander over to the bi-side of things just a little. So the thought of stopping by this guy’s place and jerking off sounded strangely alluring to me. “On the down low” is just my style, as I like to keep my adventures safe and to myself. I don’t consider myself to be gay, but fun is fun, and I’m an open minded guy. And for some reason, I have always enjoyed oral sex, both giving and receiving, man or woman. Is that what they call an oral fetish?

Back to the moment: I read the post a few times, and something about it was getting me excited. One hand was on my phone, the other was rubbing my cock though my pants. Thank goodness everyone else had gone home, as I was sporting quite a chubby as I mulled over the post. I clicked the “reply” button on the post, and wrote a reply:

“Hi. I’m a mwm, working nearby. Your post has me thinking, what should the prize be? I’m nicely hung, and not too afraid of losing. What if we bet $50? Either way, we both win if we can both jack off. For some reason I’m really horny this afternoon. But I’d need you to be very discreet. I promise I am.”

Before I could think better of it, I hit send. I immediately wished I hadn’t. What was I thinking? I don’t know this guy. The butterflies in my stomach were palpable. I tried to calm myself down, thinking about the odds of a reply. This guy probably has fifty replies, I told myself. I didn’t include a photo, which means I was unlikely to get much attention in his email. Within a minute or two I had calmed down, and started to pack up my things to head home.

Just before I grabbed my keys, I refreshed my email on my phone, and nearly jumped out of polatlı escort my skin. The reply showed up at the top of the screen, bold type and all. The butterflies were back. I clicked on the email, not realizing that I was holding my breath. The email was short and to the point, and he wrote, “Hey. Are you really hung? I’ve only had this competition twice, but I’ve never lost. $50 is a fine bet with me. When can you come over? Discreet is perfect.”

Now I had done it. What started as a curiosity had turned into something interesting, and crazy. What was I going to do? I thought about just deleting the email and going home. That is certainly what I should do.

But for some reason I didn’t. I think it was the competitive side that got the best of me. Instead, I hit reply, and wrote, “I don’t think I’ll lose. I have a nice big cock. Why don’t we make it really interesting? The winner gets to choose between the $50 or a blowjob. I’m safe, totally disease free, and would need you to be the same. I’m not too worried, and could use a good release today. I can leave now, where are you? I’m Jack, btw.”

I fired off that email with my head buzzing. That was ballsy, to say the least. I think I was secretly hoping that I would deter him by upping the ante. That way I could just go home, back to my normal routine, without feeling like I had walked away.

But it wasn’t to be. Within a few minutes, he replied again. “Ha hah. Hi Jack. I’m Steve. I’m pretty confident too. Not sure about a blowjob, as I don’t know you, but $50 will buy my drinks tonight!”

He gave me directions to his apartment complex, and told me he would meet me by the mailboxes in ten minutes. And there it was. I had committed, but anonymously. His apartment was only a few minutes away, but I didn’t have much time to think it over. Was I really this crazy? This adventurous? I should really just go home. He doesn’t know who I am, and no harm no foul, right? Right.

I quickly grabbed my keys and bag, and headed to my car. My head was buzzing with excitement, and pre-cum leaked onto my boxers as I walked. When I got to my car and started driving, I found myself quickly at an intersection in more ways than one. If I turned right, I went straight home. A left turn would take me by his apartment. I sat at the stop sign, trying to figure out what I was going to do. A short honk from behind brought me out of my fog. Much to my surprise, I turned left.

Two minutes later I was pulling into his parking lot, and walking nervously to his building. The mailboxes were out front, and nobody was there. “Good,” I thought. “He had second thoughts, and he isn’t coming.” That means I’m in the clear, and I can send him a grumpy email wondering why he was such a wimp.

Relief mixed with something else as I walked up to the mailboxes. I looked around, and didn’t see anyone. “I should just leave,” I said to myself, but for some reason I lingered.

“Hey bud!” I heard him before I saw him. “Are you Jack?”

I nodded as I saw a tall man strolling down the steps of his building. My hands were suddenly in my pockets, and my mouth went dry. Steve was about six inches taller than me, but about my age and in pretty good shape. I’d guess 6’4″, about 200. He stuck out his hand and said,

“I’m Steve. Still want to do this?”

I nodded again, and he smiled wryly.

For some reason, I wasn’t feeling so confident anymore, but I followed him back up the stairs to his penthouse apartment. It was a nice place, and clearly a bachelor pad. A big screen TV, clean kitchen counters, and a big leather sofa in the main room greeted me. He smiled again and offered me a beer. I took the cold can of beer and popped the top as we both sat down on the couch.

“Do you do this much?” he asked.

Nope, I shook my head.

“Me either. But I’m bored and could use the company, and for some reason I thought I’d do something crazy today.”

His words made me feel better, like this was a little less crazy than I feared. We engaged in some small talk about the weather, how nice it is around here in the Spring, and how well the local college basketball team did in the tournament last month.

After a few minutes, he said, “Well, should we get to the bet?”

I smiled and said, “Now or never, I suppose. Let’s do it.”

With that, he stood up, unbuttoned his jeans and unzipped. As he dropped his jeans to his ankles, I came face to cock with what was clearly a pursaklar escort much bigger package than I had planned on. His cock was at least 9 inches, thick and masculine. I instantly knew I was on the losing end of this one.

“Fuck!” I thought. “How could I have been so stupid?!?”

My heart beat even faster, and the buzzing in my ears was more intense. I stood up, unzipped, dropped my jeans to the floor, and whipped out my seven inch cock. By now it was growing fast, and oozing more pre-cum.

“That is a nice cock, friend,” Steve said, “but I think I got ya this time.”

I agreed, and being a good sport, I reached down to my ankles to grab my wallet out of my back pocket.

“50 bucks, right?” I said.

“Hold on now,” Steve said, “you said winner gets to choose between the money and a blowjob.”

There it was. My hubris kicking me in my own ass. I gulped, and once again found myself choosing between two roads. Steve seemed like a decent fellow, so I was sure I could make my excuses and just pay him the $50. Or, I could keep my word, and offer him the choice.

“Yeah,” I mumbled, “that’s what I said. What’ll it be, Steve?” I nearly whispered it, and couldn’t believe those words came out of my mouth. Stupid pride! What was wrong with me?

“Hmmm…” he said, “it has been a while since my girlfriend left town. Well, I suppose you best get to it, Jack.”

His smile told me everything I needed to know. He wanted the blowjob!

Its not that I’ve never, or think it is a bad thing. Dicks are great, and blowing them is fun. Its just that I didn’t really know Steve, and this was crazy. More to the point, his dick was really big. How does one suck something so large? I had never come close. But autopilot takes over in these situations, doesn’t it? I dropped to my knees, and he approached. I put my hands behind my back, and bent forward to take the tip of him into my mouth. His moan was instant, and intoxicating.

“That’s it, Jack. You are a little cocksucker, aren’t you?”

I mumbled my agreement into his cock as I tried to take more of him into my mouth.

“Oh yes, suck it Jack,” he crooned. “And play with your dick, you cocksucker. A good cocksucker jacks off as he sucks cock.”

He was more into it than I expected, and faster than I realized. His cock was growing now, and its weight and size were starting to freak me out. I could barely keep him in my mouth, and I was doing all I could to keep my teeth off of him. This was going to be tougher than I thought. That’s when things got a little out of my control.

Steve put his hand on the back of my head (why didn’t I notice that his hands were that big?), and moaned as he pulled me onto his cock. Immediately his dick was banging against the back of my throat, but I felt like I had barely made any progress on it.

“Oh yeah, that’s it Jack. You’re my cocksucker now, aren’t you? Jack your little cock for me as you suck a real dick, Jack.” Steve was really getting into it.

I was in over my head. I never considered myself a sub by any stretch of the imagination, but clearly he was dominating me in a primitive way. Here’s the weird part. I expected to be pissed, and to just walk away, but instead I was more turned on than I can remember. The conflicting emotions in me were like competing tsunamis. My pride and sense of self were screaming at me to get up and get out of there, but I was also so incredibly aroused by the situation that I felt my knees were rooted to the carpet.

Then Steve pulled out his cock, and slapped me with it.

Right between my eyes. Hard.

It was degrading, but all I did was open wide and wait for him to come back to my mouth. When he did, the smile on his face was slightly wicked as he told me to open up. In that moment, I knew that I was going to see this through.

My own cock was screaming at me now, and I stopped jacking off for fear of cumming. I focused on blowing him as best I could, but he was getting really hard now and my jaw was starting to hurt.

“Come here Jack,” Steve said, “you look like you’re getting a sore jaw, and I have a great idea.”

Steve pulled his cock out of my mouth (why did I miss it?), and sat back down on the couch. I stayed on my knees, and waddled over to him and pulled his jeans off of his feet. I put myself between his legs, and went to blow him some more.

“Lick my balls, Jack,” he said, “suck them into your mouth.”

And so I sincan escort did. I was grateful for the break, but also felt drawn back to his cock. But instead he jacked off slowly with his right hand as he grabbed my head with his left and guided me to his balls. At this point I was eager to please, and he moaned loudly as I rolled my tongue around his ball sack and then took one ball and then the other into my mouth. I licked up and down his shaft, never quite getting to the top to take him back into my mouth.

As I licked down, he moaned and pushed me lower. Soon I found myself licking his perineum, just below his hairy balls. He jacked harder and faster, and his moans were getting louder. And with that, I was happy. I would have rather been blowing him, but his pleasure was pleasing me.

It was then I did something I never thought I’d do. Steve didn’t say a word, but he leaned back, picked up his feet and put them on the couch, and shifted down. He kept jacking his cock, moaning loudly and smearing his pre-cum all over his head. With his left hand, he grabbed the hair on the back of my head and pushed me down even further.

“That’s it, Jack. A true cocksucker aims to please, right? You can do it, buddy.”

I soon realized what he wanted. My nose was pressed into his perineum, and the scent of his ass poured up from his spread ass cheeks as his balls sat on my forehead. He had just showered, so I wasn’t as repulsed as I expected to be. Maybe it was because I was truly his cocksucker in that moment, but I tentatively stuck out my tongue and flicked it across his puckered anus.

What the fuck was I doing? This was absolutely nuts. But at the same time, I was nearly cumming from the rush.

Steve moaned louder than ever, and said “YES!” as he pushed my head in farther. I crouched low and got under him, and started rimming him like I knew what I was doing. I licked around the outside of his anus in circles, driving him wild.

He let go of my head, and to my amazement, I stayed put. I started long strokes with my tongue, up and down his ass crack. As he started jacking off faster and moaning even more, I went for it. I used my hands to pull his ass as far apart as I could, and I drove my tongue deep into his ass. Probing, licking, loving his ass, I was lost in it. I could feel him squeezing my tongue with his muscles, and he was in heaven.

“Fuck, Jack!” he squealed, “You really are my cocksucker, aren’t you!?!”

I moaned affirmatively into his ass as I tried my best to please him. His moaning was coming faster now, and soon his ball sack started to rise.

With a shock, he grabbed my hair and pulled me off of his ass in an instant. He pulled me up on my knees, and stood quickly off of the couch, all the while jacking off furiously.

“Ohhhhh Jack, I’m coming buddy!” he shouted, as he pointed his huge, glistening cock right at my face.

I was held fast by his left hand as his right hand furiously pumped his cock. He didn’t realize it, but he could have let go and I wouldn’t have moved an inch. I could see his cock grow even bigger, and his torso flushed red as his orgasm built.

“Ahhhhhhhhhh…YES!”” he shouted as the first ropes of cum spurted out of his cock and onto my face.

The first shot hit me right between the eyes. I instinctively opened my mouth wide, all the while keeping my eyes fixated on his cock. The second and third shots hit my nose and my mouth, respectively, and then a few more rounds oozed out of him. He let go of my head, and I quickly took his cock gently into my mouth to suck out the rest of his cum. His knees shook a little, and then I opened up as much as I could and took him deep into my mouth. He moaned a quiet, soft assent of pleasure as I cleaned him up, then used my finger to clean off my forehead and lick his cum off my hand.

I hadn’t even realized it, but I had cum too, without even touching myself. That never happens to me, and I had to wonder why I was so into this. I settled back onto my heels, and Steve dropped back down to the couch. We each grabbed our beers, took a few swigs, and then started laughing.

“Well, that was the best bet ever!” he said.

I agreed, and admitted to myself that I was glad he didn’t just grab the fifty bucks. As the moment faded, we both came back to reality. Steve brought me a towel, and I cleaned him up first and then myself. With regret, I took one last lick of his beautiful cock, and slipped it back into his boxers.

We talked for a bit, more small talk but also more intimate. And then I told him I had to get home, and he walked me out. I haven’t seen him since, but he has my email. I hope he never emails me again, and at the same time, I can’t wait.

*Many thanks to Laurel and Manu for editing assistance!*

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