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?"
"Oh Charlie, you're so silly. See, the truth is, I've had a little crush on you for some time. But it looks like you have a BIG crush on me" I smiled as I grasped his cock harder through his jeans.
"Oh my God" he groaned, closing his eyes. "Is this a trick or something? Are you going to go tell everyone I'm a pervert now?"
"No I'm going to suck your dick now." I said matter of factly and moved in to kiss him deeply on the lips. If he had misgivings about my intentions, I surely lay them to rest when I let him feel all of my desire in that kiss. Our lips smashed together and our tongues intertwined. His hands were in my long curly hair as I worked to undo his belt and jeans. I moaned into his mouth as his grip on my hair tightened. He broke our kiss to look around, still scared something bad was going to happen.
"Relax, nobody is here but us and Mrs. Mirchin up in the front. We'll just have to be very quiet." I whispered while sucking in his ear lobe. His cock jumped in my hand.
"Mm you like that, huh? Do you like when I do this?" I asked and lowered myself in my knees so I was eye level with his large, 9 inch cock, now looking painfully hard as it stood at full mast. I used my soft lips to slather him all up and down the sides, making him shudder. I stared up into his eyes, enjoying every expression of disbelief, appreciation, and pure pleasure that played across his face. when I finally sucked him into my mouth, I thought he was going to cum right then and there. But to his credit, he held off. He told me later that he practised edging a lot when he jerked off by himself, so despite this being his first time having his cock anywhere near a girl, he was able to hold his own long enough to get sucked by me, and then fuck me to orgasm over one of the study tables before he finally blew his load in my mouth.
After that, we'd sneak away to the barely-used library everyday until summer break to fuck and we never got caught. We dated and fucked through our senior year as well, but when it came time to leave for different colleges, we decided to break it off and start our new adult lives untethered. And I'm glad we did because I had been having a blast. I chatted up guys in the library all the time and while nothing ever lasted more than a few fuck sessions, my pussy was happy as could be.
