1. The Big Dick Bet that Backfired


    Date: 7/24/2015, Categories: Reluctance, Author: Jack1Toffe, Rating: 2, Source: LushStories

    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 ...
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