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Dating Kelly Part I
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Add: 5 August 2015 / 11:57
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I am 25 years old, married, and completely in love with my wife. We have a baby on the way, and this is the first of a series of true stories about our teenage years together, starting with when I first asked her out. If you're just looking for sex, you won't find it yet, not for a few more parts.
When I was 16 years old I lost my virginity. I was always pretty shy, despite my ability on the athletic fields of high school, and the musculature that resulted from being a quarterback, wrestler, track runner and pitcher in baseball, not to mention all the weight lifting and cardio that went with it. Being the shy kid meant that I didn't have girlfriends through my sophomore year in high school. By the time I was a junior I was starting qb on varsity and had come out of my shell enough that I had girls I was friends with, but I still shied away from girls I wasn't friends with.
To begin, I'll describe myself. Back in junior year I was 6’1", and, as stated above, muscular and well built. I had shaggy light brown hair with natural blonde highlights and dark brown eyes. I also had a pretty large cock, about 8 inches long. As I said earlier, I was shy around girls and one of the few girls I was friends with was my next door neighbor Kelly. We had known each other for years, since her family moved in in second grade. Now we were 16 at the start of our junior year, and I was in love with her. She was a cheerleader, about 5'6", and had long dark blonde hair, c-cup breasts and an ass that looked incredibly sexy in the thong bikini she wore when we would swim in my house’s pool. She had perfect skin and an amazing figure, but the thing that got me was her eyes. Her eyes were dark blue, and when I looked in them, I felt like I was looking into the eyes of an angel.
As it is with the beginning of every school year, there was the homecoming football game and dance to think about. I was highly confident in my abilities on the field, as I had played many games before and was battle tested, but the dance worried me. As an upperclassman and as the quarterback of the football team, I was expected to bring a date, but I was so shy around girls that the thought of asking someone literally made me want to throw up.
I was sitting at lunch with my best friend Joey, who was not as good of an athlete as me but was very funny and a good actor-most importantly, he was great with girls. He told me he was planning to ask Kelly to the dance, and the look on my face told him I was upset at that idea.
"What's the problem?" he asked.
"C'mon dude, you know how I feel about her."
"I know that, but so does Tony".
Tony was, to put it lightly, an asshole. We had been friends in grade school, but when I made quarterback of the freshman team and he didn't make the team at all, his jealousy got the better of him and he started looking for ways to embarrass me. He knew about my feelings for Kelly, and he knew about my shyness towards girls. I knew that he wouldn't miss asking her out just to crush me, so I knew I had to act. I was going to ask her.
That night was a warm early October evening, and Kelly was babysitting her little sister. When I got home from practice that Wednesday (it was a long weekend) I saw her playing with the toddler in the back yard. Even though I was sweaty and smelled like a locker room I decided to head over before I lost my nerve.
I hopped the fence cleanly, but tripped over a sprinkler head and fell. Great. That's me, Mr. Smooth. I got up and brushed off my white muscle shirt and athletic shorts. I walked up behind Kelly, who was wearing tiny jean shorts and a blue tank top so tight her tits were practically popping out.
"Hey JJ".
Kelly's voice broke me out of my trance and I remembered why I was there. The moment I did I wished I hadn’t, because I got shaky knees. Real macho, right? Here I was, a 6’1" star high school athlete nearly pissing himself over asking a girl to homecoming.
I found my voice. "Hey K-Kelly", I stuttered.
"What's up?" she asked.
"Oh um ah nothing really I just came to talk".
"Oh? About what?"
"Nothing in-in particular".
"Really? Cuz that's not what Joey said when I talked to him after school".
Damn. She knew.
"Well, um, what I really came to ask about is ahmm...I'm sure you know that um homecoming um is um coming up and I don't know if ah you um had plans or um anything but if you didn't I was w-w-wonder-w-w-w-wondering if-"
I was cut off by Kelly pulling my head down close to hers and kissing me, really soft and sweet. When we broke the kiss I looked kind of stunned. She smiled at me and said, "I would love to go with you".
Relief flooded through me. 
"Thank God. I was worried you wouldn't want to".
"JJ,I know how shy you are, and I know that almost every girl in the school has had a crush on you at one time or another. I've had one for a long time. I also know that you have a crush on me".
"Was I that obvious?"
"No, but I do notice you staring occasionally when I'm in a bikini. And Joey told me."
I was going to need to have a talk with him.
"But you've had a crush on me?" I asked somewhat incredulously.
"JJ, have you ever looked at yourself in a mirror? Everything about you is amazing. Your hair, your eyes," she slid her hands under my shirt and felt my abs. "Your body. And at the same time you're incredibly sweet and humble, and I think it's so cute how shy you are. It’s like you're a puppy".
She smiled again, took out her hands from my shirt and put them against my cheeks. She kissed me again, this time letting her tongue barely part my lips.
"Eeeeewwwwww" came a voice.
Kelly broke the kiss, looked down and smiled.
"Sorry JJ. Emma’s at that age where boys have cooties".
"It's ok. I need to go shower anyway. I smell like a locker room."
Kelly laughed. "Yeah, you do. But don't worry. I kinda like it. Makes you seem manly".
With a wink she gave me a big hug with her boobs squished between us, then I turned to go. When I looked back, she had bent down to pick up Emma, giving me a great view of her ample cleavage. I stood and watched her enter her house. At the doorstep, she bent over to pick up one of Emma's toys, causing her short shorts to slip down a little, showing her hot pink thong. I went inside then and took my shower, masturbating several times to the sexy pictures of Kelly in my mind. Afterwords I was drained but elated. I had done it.
To be continued...
Thanks for reading! This is my first story to feel free to comment and critique it. I welcome all constructive criticism. I will also take suggestions for new fictional stories (i.e. not involving Kelly or our dating-not part of this true series). Thanks!
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