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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! The second one should be up in a day or two.
Campus, Ryan's tale...
Her name was Kelli. I finally found that out after admiring her around campus for several weeks. We had exchanged a glance or two and a smile here and there, before I saw her with a friend at one of the local fast food places. Earlier that week in Sociology class we had discussed the "Missed Connections" section of Craigslist and what it represented to society. That was a boring talk, but it served to get me thinking, and later that evening I put an ad up about seeing her at the food place and having some classes together, with just enough info for her to recognize me. I was really, really surprised when the first email came thru! I didn't think she would ever read my ad, much less respond to it. However, it didn't take long until we 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 emails, until the day her message simply said, "Free all afternoon and night. Let's meet somewhere private."
My heart was thumping as I typed a hasty reply. "I know just the place. A prof asked me to house-sit while he is on vacation this week." I gave her the addy and told her I'd be there non-stop after 2, when my last class of the day was over. The simplicity of her reply was enough to start my cock hardening, "K. C Ya there!"
I got to the house a little after two, grabbed a quick snack, and settled in with some TV. I knew Kelli was in class until almost 3, so I had a few minutes to relax. Our email conversations had left little doubt that this afternoon would be a sure thing for me. I only had one problem to overcome now, but it was a a rather large problem that could derail things before they ever got started. You see, Kelli was a small girl. Her B cups were the perfect compliment to her 4'10" frame, and she had just enough ass curve to make guys notice her whenever she walked around campus. She was perfectly made, in my opinion.
The problem with that was that my cock is, well, huge. As in bigger than her forearms huge. It's 11 1/2 inches long and proportionally thick. I wasn't even sure it would fit inside her at that point, even if she was willing to attempt it. I hoped she would, but I felt like I owed it to her to explain, and even show her if she wanted, and then let her decide if she wanted to attempt it or not. I knew there was a risk that she would back out, but it was a chance I had to take. I'm not that big, or tall, of a guy, so most girls (and guys) are pretty shocked that my cock is so large.
Once before, I had sort of 'tricked' a girl into trying my monstrous size, and it hadn't turned out very well for either of us. I had basically went down on her missionary, keeping my cock out of her hands and sight until she was good and wet. I had then moved up, still blocking her view, and entered her. Unlike some guys with large cocks, I have never had a problem getting to my 'full hardness', and I was fully hard that night as I entered Karen. She was ok at first, but rapidly reached her limit as I pushed into her. I managed to get a little more than half my length into her before she stopped me, complaining that it was 'too big' and wanting me to take it out. I backed out some, then fucked her for a little using only about half my cock, which she still had trouble taking. Her whimpering wasn't really pleasurable, and I found myself concentrating on just getting there. I had inched a little deeper into her by then, but she didn't respond well. "Ow! Ow! Stop! I can't take anymore! Stop now!" she almost whined. Thankfully for me, my concentration had worked. I pulled my cock out of her pussy and then, before she could register what I was doing, I leaned forward and stroked my cock a time or two, unleashing a torrent of cum on her. Most of the first blast splashed into her open mouth, taking her by surprise, and the next few spurts covered her neck and tits before she rolled away. As the last of my cum dribbled out, I wiped my cock with her sheets, pulled my pants on, and left without ever saying a word.
As I remembered that rather bad experience, I knew I didn't want things with Kelli to go that way, and silently hoped she wouldn't be scared away by the size of my cock. As I was thinking about how to gently approach the subject, I heard a light tapping on the door. I opened it to find Kelli standing there in a red tank top and grey workout pants, with her long brown hair pulled into a pony tail. I was stunned by her simple beauty, and just stood there speechless for a moment. "Can I come in, or are you going to do me on the porch in front of God and everybody?" she said and smiled.
"Oh, yeah, sorry, comein" I stammered, and moved out of the way. I closed and locked the door and turned, intending to follow Kelli into the living room, and almost ran into her. As I stopped, she reached up and grabbed my neck, pulling me down to a passionate kiss. I put my arms around and started to pull her to me, then realized my rapidly hardening cock would be obvious to her if I did so, and I didn't want her to learn about it that way. Reluctantly, I broke the kiss and held her away from me a bit. "What is it? Is something wrong? Did I do something wrong?" she asked in a flurry. "NO! NO!" I quickly reassured her. "I just have to share something with you first. Only, I don't really know how to."
"What is it?" she asked. "You don't have some kind of disease, do you?" She looked worried as she asked this. "No. No diseases," I said, "unless you count abnormal size." She looked puzzled, so I pressed on, hoping for the best, "I'm uh, very large, and I feel like it's only right to tell you, so you can choose if you want to, um, keep going."
"What do you mean, very large?" she asked, and then glanced at my crotch. "Oh." She considered a moment before continuing, "Well, how big can it be?" With that she reached out and grasped my cock thru my sweat pants. I heard her gasp of surprise as her hand encountered my cock. She looked up at me. "Is it as big as it feels? I'm not sure I could take it" followed almost immediately by "Can I see it, before I have to, um, decide?"
"Yeah, sure" I replied, already mentally preparing myself for her to decline. Lost in that thought, I was somewhat surprised when I felt her grasp my sweats and pull them down. Since I didn't have any underwear on, my cock sprang free and almost hit her in the face. "Oh my God!" I heard her murmur. She reached out with both hands and started to slowly stroke my cock. "It's HUGE!" she said, looking up at me. "It's ok. We don't have to do anything. I don't want to hurt you. Please don't feel obligated to try." I said. "It's really ok. I'm used to it."
"I don't know if I would ever forgive myself if I DIDN'T try you on!" Kelli said, much to my surprise, before continuing, "Just as long as you promise me one thing." She stood, still slowly stroking my cock, looking into my eyes, waiting. "Anything, just name it" I replied.
"Just promise me you'll stay in control." Seeing my puzzled look, she went on, "Promise me you won't get carried away and hurt me, especially if I can't take it all." She blushed at this, the redness rising up from under her shirt into her neck and face like a spreading fire. It made her absolutely irresistable! "Of course!" I said. "I would never hurt you! I promise!" "Tell you what, let's go upstairs to the bedroom, and you can start on top" I said, "That way you can control how much, how fast. Sound good?"