1. The Big Dick Bet that Backfired


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

    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. As he dropped his jeans to his ankles, I came face to cock with what was clearly a 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?!?” For some reason, my heart ...
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