Everyone in this story is eighteen or older.
I was a nerdy kid back in high school, awkward and shy and too book smart. Needless to say, I wasn't very popular, especially with girls. I spent most of my time hanging out with my few friends and trying not to get bullied.
The most popular kid was the football team's quarterback, Todd Brooks, who was cruel to less popular kids. I always tried to avoid him, but sometimes he would catch me in the hallway and make fun of me while all the girls laughed. Girls really loved Todd. He had All-American good looks and a confident charm, and it was widely known that he had taken advantage of it by fucking every hot girl in school. Each one would try to go steady with him, but he never dated one for more than a few weeks before moving on.
I was the exact opposite, never had a girlfriend. Not that I was an ugly or fat guy, though. In fact I considered myself a pretty good runner. I didn't have the guts to try out for the cross-country team at school, but I ran several miles every afternoon, and I was proud of my speed and my endurance. Still, the furthest I had ever gotten was kissing some random girls at camp or other places away from school.
But that changed the first week of senior year, when we had a student transfer from another town. The first time she walked into my calculus class, my heart jumped in my throat. She was a gorgeous brunette with a cute button nose and beautiful eyes, and she had a firm, tight body to match. She was wearing jeans and a revealingly tight shirt that hid a round, firm pair of B-cup breasts.
In a great stroke of luck, she was assigned to sit next to me. At first, I didn't say anything, assuming that a girl that hot wouldn't want to talk to a nerd like me. But then I realized that she didn't know anyone yet, and that this was my only chance to talk to her and get on her good side before she found the popular group.
So I struck up a conversation with her. To my delight, she was eager to talk to me. Her name was Teri, and she had been a cheerleader at her previous school, but moved too late to join the squad here. So she didn't have any way to make friends.
The next few weeks seemed like a dream. Teri and I clicked, and started spending a lot of time together, even as her popularity started to grow and she hung out more with the popular kids. She wasn't talkative, but she was smart and sweet and laughed at my jokes.
We started hanging out after classes in a small field down the hill from the school, where we would talk for as long as we could before one of our parents called and demanded we come home. Finally, after a month, I built up the courage to kiss her. She returned the kiss, and we started officially dating.
But soon it became clear that kissing was all we were going to do. Teri said she was very conservative about fooling around, and didn't want to go any further than making out. Our dates would be fun but would end with a 20-minute kissing session in my car in her driveway and then her leaving. One time I tried to touch her breast over her shirt and she flipped out. "I'm NOT that kind of girl, Peter," she said, and grabbed her purse and got out of the car. It took an hour of apologizing the next day before she forgave me. After that I kept my hands to myself.
Still, it was the best time of my life. But it all changed once Todd came into the picture. It didn't happen suddenly. The first few times he saw Teri he ignored her or just smiled at her. But as she became known around the school and started hanging in the same social circles, I started to notice him take more of an interest in her. It wasn't anything troubling, I'd just notice him chatting with her for a few seconds in the hallway between classes as I was walking up to her, or sitting down next to her at the cafeteria while she ate with the popular kids.
She brought him up one day while we were on a date. "Do you know Todd Brooks? Our quarterback?" she asked casually.
"No, not really," I said. "He's actually pretty mean, he sleeps with all these girls and then breaks their hearts."
"Wow, he sounds like a jerk," she said. And that was that for a while.
I thought she would keep away from him after that, but she kept letting him hang around her. Soon she even started to respond to his attention. From across the cafeteria or hallway, I would see her smile and flirt with him, and when we were together she would start to bring up Todd more and more in conversation.
"He's actually sweet," she'd say. "A total jerk, but he's not bad. Just a horndog."
It was a slow process that made me suspicious that she was starting to be charmed by him. Looking back on it, I should have done something at that time, but knowing how prudish she was and how committed she was to me, I assumed that even if Todd tried to do anything with her, he would be swiftly rebuffed.
Then one day while Teri and I were sitting on the hood of my car in the field behind the school, I spied Todd and several of his jock friends walking up to us. Sometimes others students hung out in the field, but this was the first time I had seen Todd there, so I immediately knew he was up to something.
"Hey, Teri!" he said. "Whatcha doing here with Peter? He helping you with algebra?"
Teri giggled, which wasn't the reaction I was hoping for. "No, we're just hanging out," she said. "Enjoying the day!"
That could have been the end of it, but my wounded pride made me make a huge mistake. "I'm not just a math guy, Todd," I said. "I'm a pretty great runner, too."
"Oh, really?" Todd said. "Funny, I've never seen you on the track team."
"You don't need to be a jock to be athletic," I shot back. "I bet I'm faster than you, even."
Todd raised his eyebrows. "Really, you think you're faster than me? You know what this letter on my jacket stands for, right?"
I was thinking of something to say back, when Teri said, "Why don't you guys race to prove it?"
"Sure," Todd said. "Let's do it right now."
"Okay," I added, trying to sound confident. I wasn't really sure I could beat him in a race, but I couldn't let him call my bluff.
"Let's make it worth something, though," Todd said. "Winner gets a prize."
"Like what, money?" I asked.
"Sure, maybe. Or maybe you do all my homework for the rest of the semester," Todd said.
I was thinking about this when Teri broke in. "Hmmm..." she said, "how about the winner gets to see my boobs?"
