Where it happened: Her house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
The summer that I was 16, I fell head-over-heels in love with a girl named Sara. It didn’t matter that she didn’t appear to have any feelings for me, or that she was, at the time, only 12 years old. I was obsessed.
Sara was beautiful, undeniably beautiful, could-be-a-model beautiful. Her face was adorable. Fair skin, high nordic cheekbones, pale blue eyes – I couldn’t look away. She lived across the street from us, and a few houses down. She, along with many of the neighborhood kids, would come swim in our pool almost every day, where I was usually responsible for watching over the younger kids. She was the same age as one of my sisters, and they sometimes played together. I tried to find something, anything, to talk to her about, but couldn’t seem to hit on anything.
Sara’s best friend, who usually came to the pool with her, seemed to be just as infatuated with me as I was with Sara. Also 12 years old, her name was Kasey. Kasey was a fellow music obsessive, and spent the summer asking me about bands I was into, shows that I had seen, if I was getting any better at playing guitar. Fortunately, Sara would come along whenever she wanted to come into my room to listen to music. The three of us spent many hours in my room, still in wet swimsuits, listening to The Smiths, The Pixies, Depeche Mode, The Cure, Peter Murphy, The Replacements. Kasey was thrilled. Sara often seemed bored. I was simply enthralled with Sara, excited that she was in my room.
As the summer went by, it became more and more obvious that Sara just wasn’t into me. It took a stray comment from my sister that “Sara has a boyfriend now,” for it to really sink in. I was a romantic, and was crushed, thinking I’d never recover. I was moody. I sulked in my room. I cried myself to sleep at night.
I was over her in a matter of weeks.
School started again, and I became interested in newer friends, newer interests. I turned 17. And as the school year went on I discovered, to my surprise, that while I hadn’t given Sara a second thought, I actually missed Kasey. I missed all of our easy conversation, playing and talking about music, making fun of people behind their backs, almost finishing each others’ sentences. Kasey was funny and mature and smart, especially for her age, and I couldn’t believe I’d taken her friendship for granted, while obsessing over Sara. I was ashamed to admit that, while I’d memorized Sara’s phone number, birthdate, everything about her, I didn’t even know where Kasey lived. I really missed her.
One hot day during Spring Break in April, I was at the park, playing basketball half-heartedly with a friend. I saw two girls walking toward the swings, and became excited when I realized one of them was Kasey. She was with another friend – one I hadn’t met. Shortly after, my friend had to leave, and I hung around by myself, shooting baskets, until Kasey’s friend left, then I went over and sat next to Kasey on the swings, said “Hi”, started catching up.
We soon hit it off just like we had the summer before. She mentioned that an older cousin of hers had given her a mixtape that she thought I might like. Did I want to come to her house and listen to it with her? Of course I did.
We walked to her house, which turned out to be not far from my house. On the way, I realized what I, like an idiot, hadn’t noticed the previous summer – that Kasey was beautiful. Her reddish brown hair went perfectly with her somewhat freckled face, chubby cheeks, pale skin. She was wearing shorts, and I watched her legs, admiring them, and her bare feet, becoming grass-stained as we cut through yards. The previous summer, I’d written off Kasey as fat. And yes, she was somewhat fat, although now I realized that she was just a little fat, nowhere near obese, and that on her, it was actually kind of cute. She had turned thirteen, and suddenly was, to me, absolutely beautiful.
We finally made it to her house. Her parents were both at work, so we had the house to ourselves for awhile. In her room, Kasey started the mix tape, and we sat on the bed side by side. She convinced me I needed to take off my shoes so I could sit all the way on her bed. Then she just pulled off my socks for the fun of it.
We sat side by side, listening, talking, starting to flirt more and more. This was the very early nineties, and she had one of those snap-band bracelets, that we were playing with, snapping it on each others’ wrists. Once, after she snapped it on me, she let her hand linger near mine, and I almost instinctively just held her hand. We held hands for a few minutes, when I felt bold, and leaned in to kiss her. She felt wonderful.
We kissed slowly and tenderly, lying side by side. At some point, side one of the tape ended with a loud click, making me jump. We just kept kissing, and caressing. Kasey started caressing me beneath my shirt, and sort of pulled on it, hinting that she wanted to take it off. I lifted my arms and she pulled it off of me.
I was still nervous, and naive, and wasn’t sure whether I should make a move for more. Kasey started playing with the waistband of my shorts, and then just asked “Aren’t you gonna undress me?”
“Oh yes.” So I did. Quickly and clumsily, it seemed, we were both naked. In my inexperience, I proceeded to essentially grope Kasey everywhere, trying to feel her everywhere, kiss her everywhere. She caressed my penis, kissed me on my neck, and face, and just let me enjoy her body.
Eventually, Kasey rolled onto her back, and I climbed betweeen her legs, and tried to enter her, but had some difficulty at first. I tried again, and Kasey helped me, and with a slight adjustment in our position, she was able to guide me inside her. Kasey was tight, I was excited and inexperienced, so to be honest, I didn’t last long, but I kept thrusting as long as I could after my release, until I softened completely, listening to Kasey reach her climax just after me.
We rolled to our sides, and just sort of held each other for awhile, not knowing what to do. Finally, Kasey said “I gotta pee,” and went to the bathroom. When she came back I took my turn in the restroom, and walked back into Kasey’s room, where she was lying on her bed, still naked. I lay next to her. A few minutes later, she got up, walked to the boombox, and turned the tape over, starting the other side. I watched her, thinking I could enjoy just watching her naked all day long. She lay next to me again, and we listened to Side 2, still naked, just kissing and cuddling for a long time.
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