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This will really be two stories, each separate from the other. One from his viewpoint, and one from hers. Let me know what you think! This is the second one...
I kept seeing this guy around campus. He was clearly admiring me, but would look away and not stop walking whenever I would try to smile or encourage him to stop and chat. I knew his name was Ryan from a class we had together. One day he saw Megan and me at a local fast food place. Megan was my BFF, and we went everywhere together. "There's your admirer" Megan smiled, even as Ryan ducked out the door. "Maybe he'll put up a 'missed connection' ad," she joked. "Then you can actually get to talk to him." Earlier that week in Sociology class we had discussed the "Missed Connections" section of Craigslist and what it represented to society. It had been a boring lecture, but it ended up serving a purpose, I suppose. The next afternoon, Megan and I were laughing about the whole missed connections idea again, and I pulled it up on a whim. Boy, was I surprised when I saw the ad. I clicked on it, and we both read it. "That's YOU!!" Megan squealed. "OHMYGOD, he REALLY did it!" Even though I was really surprised to see it, I told Megan I was going to respond. After that it didn't take long until Ryan and I hit it off and were conversing regularly via email. We both had reasons why we couldn't be obvious about anything that might happen, so we limited our conversations to email. One day over lunch, I told Megan, "Enough of this playing around. I'm going to see if he's serious", and sent Ryan a message that said simply, "Free all afternoon and night. Let's meet somewhere private."
His reply was almost immediate. "I know just the place. A prof asked me to house-sit while he is on vacation this week." It included the address and said he got out of class at 2, which would work, since mine lasted until 3, so I sent back, "K. C Ya there!" "Kelli's gonna get some, Kelli's gonna get some!" Megan grinned at me. "It's about time you quit being so uptight!" "Yeah, yeah, you're just jealous 'cause I can live without it for more than week" I laughed back at her. We exchanged some more friendly banter for a while before heading on to class.
Despite my bravado with Megan, I was still sort of apprehensive. I had heard thru the athletic grapevine (I was there on a golf scholarship) that Ryan was 'well endowed'. No specifics, but he was said to be 'significantly above average'. And me, I had always been a small girl. No medical issues or such, I was just one of those people who weren't very big. I was pretty well built, however, with perky B cups which were the perfect complement to the rest of my 4'10" frame, and I seemed to notice guys looking at my ass whenever I walked around campus. I found out later that Ryan thought I was pretty much the perfect woman.
Part of what made me apprehensive was that I had only been with two guys, and the first one had been one of those 'well endowed' types. I had been 15 years old at the time and a naive freshman in high school. He was a senior named Sam, and just acknowledging that I existed was a big deal to me, so when he took an interest and started talking to me I was smitten. One day after school I heard a knock on the door and looked out the window to see Sam standing there. I wasn't supposed to have company since my mom wouldn't be home for two more hours, but like I said, I was smitten. I opened the door, intending to only talk to him right there, but before I knew it I was showing him the upstairs game room. I remember saying something about the pool table and starting to turn around when he grabbed my arm and spun me back to him, leaning down and kissing me as my body pressed into his. I was frozen with a mixture of fear and excitement as his hands roamed my body, electrifying me at every touch. I didn't know what to do our how to react, so I just kept kissing him, not really aware of all that was happening, though at some level I knew what was happening. Some part of my mind even thought I should stop it, but the tingling in my body overruled that part. I put my hands on his, meaning to stop him, as he grabbed the button of my jeans and started to undo it. However, he simply slowed down a little, moved my hands aside, and went back to my jeans, unbuttoning them and pulling the zipper down. I was starting to tremble as he pushed them and my panties downward, almost to my knees. He broke the kiss then and moved around, nibbling on my neck before whispering in my ear, "Relax, it's going to be good." I felt his arms around me then, leaning me back and lowering me to the carpeted floor next to the pool table. I just clung to him and let him lay me down. When I was on the carpet he quickly slipped my shoes off, before grabbing the cuff of my jeans and tugging them off, followed by my panties. He lay on top of me then, kissing me again while his body parted my legs. I had never been with a guy and didn't really know what to expect. Again I realized that I should stop this, but I just lay there and let him continue.
I had a tense moment when I almost did stop him when he raised up on his knees pushed his pants and briefs down, exposing his considerable length. I found out later he was 9 inches, but at the time I only knew that he looked bigger than the pictures I had seen of 'average' guys. However, just as I opened my mouth to say something, he dove forward and kissed me again, even as he was reaching between us. I gasped as I felt him touch my virgin pussy, stroking his fingers up and down my slit, finding me wet, before lodging the head of his cock between my outer lips, pressing against my opening. He began pressing his hips forward then, attempting to drive his cock into my body. However, I was so tight that he ended up pushing me across the carpet. I let out a short cry every time he pushed forward. I even tried to brace myself, but there was nothing for me to grasp on the game room carpet, and so I just kept sliding as he continued to move forward and push his cock toward me. After a few brief moments, I felt the top of my head hit something, and realized I had moved all the way to the wall and was now lodged against it. Realizing this, Sam reached down and lifted my knees toward my shoulders, bracing me against the wall and pistoning his hips forward, finally gaining some leverage. "Oooooowwww!" I cried out as his cock began to force its way into my super tight opening. The heat and pain were intense as he slowly wedged himself into me, going deeper with each push and pressing me hard into the wall now. Now I really wished I had stopped him earlier, but I couldn't manage words at this point, and so simply endured the large spike that was being driven into my formerly virgin body. Just when I thought I was going to break in half, I felt his hips meet mine as he pressed the last inch inside me. I let out a gasp as he finally quit pushing for a moment. "Good God you're tight!" he said thru clenched teeth, "I've had other virgins, but you're the tightest pussy I've ever been in!" With this he began to stroke his cock in me. Even as wet as I was, with his size it was still difficult for him to move in me, but eventually he got a rhythm of short strokes going.
.... There is more of this story ...