Dempsey asked me if I wanted to bet him $100 that he would win the art contest. I accepted the challenge, not knowing where I'd get the money should he win. But I felt confident in my abilities and no so much in his. It was a shock to me when I learnt that he had won top prize. The next day I was feeling panicky and worried that I'd meet him in the hallway. I did my best to keep a low profile but after a few days he caught up to me.

When I sheepishly said that I didn't have his money at the moment, he smiled and said we would have worked something out. "Like what?" I wondered. "Well you could give me a blow job, Ha ha", he joked. I blushed and became speechless. I looked down at his crotch and swallowed hard as I secretly thought there would be nothing I'd like more. He was so cute with his boyish good looks, athletic body and self-assured charm. I must have guessed my desire because he suggested we go to a quiet place in a stairwell where he "wanted to show me something."

"Look, I'll pay you the money. I just need a bit of time." "Shhh, relax don't worry about it, it's not a big deal", he assured me as he guided me to the stairwell. "there you see, no one around to bother us." He unzipped his pants. "Ever sketched a penis before? Ha ha. Pull it out and see what you think? I bet you'd like it" I nervously reached in his pants and pulled it out. His beautiful, soft, warm, uncut flesh filled my hand. It felt wonderful and mesmerizing and I began to stroke it slowly. "You won't tell anyone, right?" I asked, half pleading. "Oh no it'll be our little secret. So what do you think?" I blushed again and smiled shyly. "Nice", I said, "really nice"

He gently pushed my head down. "Take a closer look". I trembled as I took it in my mouth and started sucking. I felt him grow and I struggled to take him all the way to the base. As I sucked him harder, my mouth was stretched and flooded with the taste of precum. His moans encouraged me and grabbed his firm ass cheeks to suck him properly. Soon his beathing became shallow and could tell he was about to cum. I was overtaken by desire and sucked him wildly as my shyness and reserve dissipated.

I massaged his balls with my hand and the underside of his cock, below the head, with my tongue until waves of delicious cum poured into my mouth as he moaned and grunted. I stroked and kissed it, to milk the rest of his cum. I swallowed it more out of politeness than anything else. "Oh you swallowed too! That's awesome. You have a real talent for cock sucking" I was pleased that I satisfied him. I stayed kneeling in front of him as he put back into his pants. "So, I'll give you another week for you to give my my money" , he said. I froze. I thought my debt was forgiven. "If not you'll have to suck me again" Needless to say I didn't have the money the following week...