Last May I found myself in another predicament. Once again, it was my own fault, but what happened was both exciting and unnerving.
One afternoon last May, the sun was shining bright into my office window as 4pm came and went. May 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 Craigslist personals.
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, and it was posted in the casual encounters section of Craigslist. 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.
“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, thick, 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 wonder 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’m not 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 copied the address. I logged into my personal email, 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 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. “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 May, 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.