The best weekend of my life started out simply enough. I drove the six hours separating mine and my best friend, Mary's, colleges and stayed at her house for a nice, long, holiday weekend. And I was determined to get laid.
I arrived at Mary's house Friday night with plenty of time for catching up, dinner, and drinks in her living room late into the night. We were surrounded by her roommates and friends allowing me to get to know some new people. See, she lived in a 5 bedroom mansion off campus where each room was rented out by someone. And one of those people was a guy named Keith.
Keith was the perfect guy as far as I was concerned - tall, big build, and almost completely silent. I must admit, I had always had a thing for shy guys and I think the quietness is part of the reason. They aren't loud or boisterous and they don't prattle on and on just to hear themselves speak. But they appreciate bolder people and when they do speak up, listen carefully, because it matters. I could tell Keith wasn't stupid, for he listened attentively and laughed at all my jokes, but he was a man of few words. I knew the chances of my first attempt on my first night in town working out were slim, but I had to try. He had the looks and right temperament, now I had to see if he had the last major requirement, a big dick.
Flirting with a shy guy takes a certain finesse that I had perfected during my highschool years after several failed attempts, of course. Afterall, it is through failure that we grow. With a guy like Keith, you have to take control but not overwhelm them so much that your scare them off, and you still have to give them some room to feel like they had a hand in steering things along. That was key. Even a shy guy needs to feel like a man and it can't feel like charity or they'll never go for it.
After a few failed attempts in highschool, I had perfected my technique with Charlie, a shy nerdy guy who was in all AP classes by our Junior year. After getting assigned to a project together, I made sure to flirt with him in the library, a place he felt most comfortable and in his element. Sure, I touched his arm when talking to him, gave him the doe eyes, the basics. But it was asking him to get the books on the high shelf that really did it. He needed to feel needed, and so I showed him I needed him. As I stood in front of him, facing the book shelf, he reached above me to grab some random book I had pointed out, and I could feel his hardening cock brush against my butt. That's when I knew this was my chance. I thrust my tush back, just a little bit, pressing into his cock more. I gasped in fake surprise while suppressing a moan. I whipped around with pretend horror in my eyes. The fear in his was definitely real.
"What is that?" I demanded to know.
"Um, um I'm so sorry!" he sputtered nervously, dropping the book he had grabbed for me. I stared into his big brown eyes and let my expression soften.
"Oh sweetie, you can't help it." I cooed, bringing my hand closer to his growing bulge, but careful not to touch it yet.
"May I?" I asked. Dumfounded, Charlie gave a little nod. I rubbed his bulge gently while showing my appreciation. I could tell he was big.
"Wow, you have a big cock. And you want me to play with it?" I asked, sounding honored.
"Oh my God, what is happening?"
