I never imagined that picking someone's pocket would get me laid. I was for the most part straight in the sense that I would only screw girls. Over spring break I went to Daytona with a girl three years my senior (I was 20 back then!) with the only intention of drinking and fucking. That for sure happened, but in spite of my companion's experience I did not quite have the pleasure that I expected. Yes I had several orgasms, but somehow they were not as fulfilling as my masturbations where I would please myself shoving vegetables up my tight ass.

Yes, you read right, VEGETABLES. My favorite was Mr. Zucchini, not only could I model the thing to resemble a nice hard cock but also learned that by striping the skin off, the thing would be naturally lubricated. Perfect fit for a college student on a budget. No need to buy expensive gadgetry that would be hard to figure out. Boy that thing went in like butter...I'm getting a precum stain in my shorts just thinking of it.

Upon my return I found my roomy Claude already there. He was not able to square out anything for the break so he had stayed in town. I was not sure what he did, but I knew hadn’t had sex. I could tell because he was already cranky. We had been roommates since junior year and never applied to a frat house or moved out given our tight economies. Over the years I had notice his package. Not an ordinary thing.

I had seen it through his skinny jeans, resting over his right leg. That made me think he either used boxer shorts or nothing at all. The meat was there hanging on the side and in more than one occasion I did the "pull the towel trick" at the showers, just to glance at him naked. Believe me the real thing was better than its silhouette, and that miserable Spring Break he had just had, gave me my opportunity.

We started to make loose conversation and I told him about my week. Some of the details did have an effect on him as I saw his dick hardening from under his baggy shorts. I talked about a lot of things and dared him that he would not notice if I picked his pocket. Very competitive he was, and took the bait.

I stood behind him and told him I had three chances to get my hand inside his right pocket without him feeling anything. The first time was all clumsy on purpose and I stroked the back of my hand against his dick's head. I was sure he wore nothing underneath!!! He did not react negatively to it so I went a second time. Now, much closer to his back, I slid my hand very slowly making it a point to get my fingers to just brush his head again.

I asked, “Did I lose?”

“Not yet,” he answered.

Liar, I thought. I kept it there and felt wetness on my fingertips and softly I put my fingers around his shaft through the pocket's liner.

“Did I lose?”

“Oh no, not yet,” was his answer, so I stroked him gently while I put my other hand through his waist to caress his balls. His dick was completely erect and his balls dangled freely on top of my hand. Now he did say that I had lost and asked me what was the penance.

Vote: Total Votes: 11 Steamy (1 vote) Hot (2 votes) Blazing (3 votes)

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