High School Sweethearts

I remember Kate as a cute girl with a personality so huge that it could be rivaled only by the size of her spectacular breasts. I’ll be honest. It was the breasts that first attracted me. What can I say? I’m a man. We met during our sophomore year of high school in a British Authors class that would have sent me straight into a coma had it not been for the fact that Kate sat directly in front of me. I can still smell the sweet aroma of shampoo emanating from the blond hair trailing down her back which barely whispered across the top of my desk. I can see the narrow curve of her strong shoulders and the outline of those magnificent tits peeking out from either side of her tiny frame. It was as if they were teasing me, playing peek-a-boo as she shifted in her chair.

It took me weeks to get up the courage to say anything more to her than, “Hi, Kate,” or to ask her how the swim team was doing. But such banality drove me insane. All I really wanted was to find just the right words to express to her how much desire I was filled with, and then take her behind the stadium and have my way with her.

I imagined myself there countless times, pressing her up against the cold, red brick façade and sliding my eager fingers into the front of her jeans, finding the forbidden pool of hot wetness there, and making her cum while pressing against her clit with my tongue buried deep in her mouth.

I suspected that Kate was a virgin. She was sweet, polite and funny. She dated a lot of different guys, but never for long. I suspected that when it came to sex, she was saving herself for just the right guy. I wanted that guy to be me. I can’t say that I was actually in love with her. I just wanted her. I wanted to get lost in her laughter, in her eyes, and in the pussy that I imagined was second to none. As I sat behind her each day, with my painful erection tucked awkwardly in my jeans, I could almost taste her. My mind played delicious tricks on me as I got lost in fantasies that seemed so real, of my tongue trailing down her torso, between those soft mounds that I so wildly desired, along her tight tummy and down to her moist slit, which I would have feasted upon without hesitation.

I could taste her. As her hair tickled my desk and filled my nostrils with the scent of rosemary and mint, I closed my eyes and I could actually taste her. I visualized her standing against that wall, legs spread, panties around her ankles, her hands pushing my head harder against her. I could feel her hips rocking into my face as my tongue peeled her labia like a grape, revealing the sweet molten prize that lie inside. She squealed. My hips rocked forward spontaneously and jolted me back to reality. I caught the hint of a knowing smile on Ricky Holden’s face which made my aching erection shrivel up and take its usual place against my sweaty testicles. God damn him!

Then came the day I dreaded. The day I saw her walking down the hall with Christopher Camp. Their arms were wrapped around each other’s backs and he had his hand placed in the back pocket of her Calvin Kleins. My heart sank. It would be impossible for me to fantasize about claiming her as my own now that she was with Chris. She looked happy, radiant in fact, as they strolled down the hall together, laughing and kissing. Thinking back to the short-lived nature of her previous relationships, I knew I had to formulate a plan. This shy, scared kid was going to have to become a man. I needed to find a way to worm my way into her life. I needed to get her to see me as more than the kid that sat behind her in British Authors. I needed to make her want me. If I could do that, I knew she’d leave Chris like she’d left all the others before him, and she would be mine.

I began acting out my plan by showing up for class early and hanging around outside the door until she appeared at the head of the hall. I would have my newest cassette playing in my walkman, set to the sexiest song I could find. “Hey Kate, take a listen,” I’d call to her as she approached, holding out my headphones.

“I like it,” I remember her smiling, as she bobbed her head in time to Prince’s Do Me Baby. Step one complete.

“Hey Kate, nice skirt. Is it new? You really rock it.” Was that a stupid thing to say?

“Thanks, Ben,” she replied with downcast, shy eyes and the hint of a blushing smile. I guess not. Step two complete.

‘Great job in the swim meet last night, Kate. I hear you got a personal best! That’s awesome. I’ll have to come to your next meet and cheer you on!”

“Thanks, Ben! I’d love it if you came.”

Step three complete.

I heard that Chris and Kate were on the rocks shortly after step three. Which brought me to step four. Complete.

Step five was the hardest. I had to make a move before one of the many suitors who’d been waiting in the wings could get to her. I felt them perched like buzzards in the trees, waiting for her most vulnerable moment. Each envisioned themselves as her white knight. Each wanted to swoop in and take Chris’s place. Fuck ‘em. That place was mine. I’d calculated my every move. Operation Ben and Kate was in full swing.

Back to step five. It was now or never. My palms were sweaty and shaking as I dragged them along my thighs. She was at the head of the hall again, headed toward class. Her eyes met mine from a distance and she smiled and waved at me. Her eyes actually sparkled with recognition and joy. Today was the day.

“Hey Kate. Can I talk to you before class?”

“Sure,” she responded without hesitation. “Do you want to walk with me?”

She was making this easy. We walked away from class and back toward the main hall.

“How would you feel about skipping class today?” I inquired, not exactly sure what I had in mind. I just wanted to be with her and not spoil the connection that I felt we were certain to make.

The look on her face was one of intrigue. “Okay,” she answered and strode alongside me as we exited the building and ambled toward the stadium.

My chest ached with nervous anticipation. After several minutes of small talk, which was so easy with her, I decided that the time was right.

My feelings poured out in waves, spilling across the front of her dress and grass beneath our feet. They lay before us for her contemplation. She didn’t seem surprised. She didn’t seem revolted. Things were going well as she turned to face me.

“Are you asking me to be your girlfriend, Ben?” she asked quite directly.

“I’m not sure what I’m asking, actually,” I said, gazing down at the grass. “I don’t want to be your next ex-boyfriend. I really like you. You make me feel things that I’ve never felt before. When I look at you…” I paused, considering my words carefully, “My body responds. My chest gets kind of tight and my stomach gets a bit jittery. You do things to other parts of me too,” I smiled, speaking with the halting uncertainty of a high school kid.

I looked up to gauge her reaction. Would she be flattered, or would she slug me?

“What other parts?” she smiled wickedly, sensing my discomfort and forcing me to confront it. Oh, she was deliciously wicked. I hadn’t expected that.

We were now behind the stadium. The red brick wall that I had fantasized about was there. She was standing there in front of it. My erection grew instantly, just like it had as I imagined this exact scene from my seat in British Authors class.

I looked down toward the obvious bulge in my pants. Her eyes followed suit and she was transfixed.

“Ben,” she whispered, and raised her intoxicating blue pools to stare into my penetrating black ones.

My body lurchced instantly into hers and she fell back against the bricks, breathing heavily. Her eyes fell closed and her lips parted as I braced myself against the wall and pushed my erection into her pelvis. She whimpered as I pressed against her and her hands roamed greedily over my pecs and around to my shoulders. Was this really happening? Was I making out with Kate Whitman? I had never felt so close to cumming without actually masturbating before. She felt so good beneath my palms. Her lips tasted like watermelon and I was growing rabid to know what her pussy tasted like. Would that be going too far?

She answered that question for me as she unzipped her fly and let her jeans fall to her feet. She grabbed my hand and forced it into the front of her panties, just like in my fantasy. I was stunned. This stuff never happened to guys in real life. Never! And yet there I was, wiggling my fingers inside of the hottest, wettest and softest pool I would ever have imagined. My hips rocked uncontrollably now, slamming against her as my fingers pushed up inside of her, hitting her g-spot with very little effort. She bowed at the knees to meet my dexterous thrusts. Her wetness pooled around my fingers and ran into the palm of my hand. I could smell her. Hers was the first pussy I had actually touched and smelled. I wanted to taste it so badly. My cock was throbbing relentlessly in my jeans. I needed to take them off and set it free. What would that lead to? Would I be able to stop myself from plunging my painfully engorged cock into her and fucking her hard against the wall? I wasn’t sure. My desire was beginning to take over my body and it scared me. How far should I go? How far did she want me to go? Only a few months earlier I didn’t even have the courage to speak to her. Now it was possible that I could be losing my virginity to her, and taking hers in the process.

A strong, elongated moan emanated from my chest.

“Take your jeans off,” she commanded, as she set to unbutton them.

Sweet fucking Christ, she made this so easy. Maybe I’d been mistaken. Maybe she wasn’t a virgin. This was awfully forward and confident for a girl that had been saving herself. I hated myself for hesitating, but I had to know.

“Kate, are you sure?”

She smiled seductively and her eyes grew wide with eager consent.

“Have you done this before?” I asked, stroking my cock now as it bounced out of my boxers.

“No, but I want to. You make my body feel the same way you said I made yours feel. So let’s do something about it.”

“What about a condom or something?” I asked, my good senses starting to interfere.

She looked as if I had startled her into reality as well. “Oh, Ben,” she sighed, “I…I…”

“It’s okay, we can do other things for now,” I smiled, trying to reassure her, though my insides were quaking and my cock was ready to jump off my body and beat me to death for denying it the intense pleasure of fucking her.

“Can I stick my dick in your mouth?” I asked her, not sure if she would consent or be revolted.

“Okay,” she grinned, but I sensed a bit of reservation.


“Mmm, hmm.”

Kate dropped to her knees, gazing up at me and placed her warm hands on my hips, guiding me forward.

“Let me know if I’m doing it right, okay?” she asked sweetly, like child that needed approval.

“I will,” I said, my voice catching as her lips parted over the head of my dripping cock.

The precum didn’t seem to bother her. It was almost like lipstick as she rubbed my tip across her full lips. I could see them glistening with my juices and it turned me on in ways that I had never contemplated.

If this was her first time, she was a fucking prodigy! Her mouth was warm and cavernous and she slid my cock over her smooth tongue and pulsed the inside of her cheeks against my shaft. Her saliva pooled quickly and dripped from her mouth as she held me tight, sliding up and down the aching pole with varying speeds. She sucked nearly my entire cock into her mouth and I could feel it hitting the back of her throat. I wanted to shoot my hot cum down her throat. Would she allow that? Did I need to ask permission? I wasn’t even sure what the protocol for dick sucking was. My fingers were entangled in that soft blond hair. I guided the depths of her oral talent with my hands, pushing her as deeply onto my cock as she could stand. Her hand wrapped around my balls, and she massaged them and tickled them. It was as if she were trying to milk and suck the cum right out of me. It wouldn’t be long. I wanted to hold out, but I knew I couldn’t. Anxiety engulfed me as I felt the cum rising up my shaft. I wanted to spill it into her mouth. I wanted her to suck it up and swallow it. That would be so fucking hot.

I started grunting and panting like a wounded animal. “Oh, Kaaaaatttteeee,” I groaned. “You’re going to make me lose it.”

She didn’t look up, yet she sucked harder. I looked down and saw her free hand playing with her pussy. I felt the hum of tiny squeals reverberating on my cock as she sucked me off.

“Kate, Kate, I can’t….stop…it…here…it…cooooommmmes,” I moaned so loudly it might have drawn attention to us.

She pulled off just as the juice shot forth in copious squirts and dripped from her cheek and chin.

I guess it would have been a lot to expect a first timer to swallow it, but for a moment I really thought she might. I pulled a wad of tissue from my backpack and helped clean her up.

“That was awesome!” I almost shouted. Looking back now, it seems such a juvenile response. But hey, I was kid.

She smiled with a glazed look on her face. That’s when I noticed that her fingers were still pulling at her pussy.

“Oh Kate,” I sighed, feeling a little guilty for ignoring her pleasure until now. “Let me help you, baby.”

I gently pushed her onto her back and stretched out next to her in the cool grass. My palm cupped her and I could feel the intense heat radiating from between her thighs. I gauged my technique by the look on her face and the throaty sounds she made as I wiggled and pushed against her clitoris. Her hips rose against my fingers and she lost control of her breathing.

“I want you to have an orgasm,” I said in a husky voice that was barely recognizable. “Do you think that’s possible?”

“Yes, I think so,” she sighed with her eyes clenched closed, “just keep doing that.”

I obeyed her commands, not knowing exactly what to expect.

My fingers slid between the folds of her labia now, coated in sticky, thick moisture. I spread her thighs farther apart and rose to kneel between her legs.

“May I kiss you, Kate?” I asked permission, though I’m certain it wasn’t required.

“God, yes!” she almost screamed as I set to work on devouring her.

The taste was somewhat salty but rather appealing. I found that the art of eating her out came as naturally to me as breathing. I might have been put on earth to lick this girl’s pussy. It seemed quite logical and plausible at the time.

My tongue found its way inside of her, but it didn’t take long to discover that the best reaction came when I flicked the underside of my tongue rapidly against her clit. My tongue damn near cramped up, but as her hips rose one last time and she squealed like a dying rabbit, I knew I had her. Her body shuddered against my stubbly chin and I looked up to see her stroking and pulling at her erect nipples. I had given Kate Whitman her very first orgasm.

Who knows? Maybe I did love her after all. To this day, I can still see her smile and the sparkle in her eyes. I can still see the hint of her bosom peeking out at me in British Authors class and I can still taste the fresh, salty juices of the magnificent pussy that she opened for the first time to me.

Our twenty-five year class reunion is just around the corner. I can’t help but wonder if she’ll be there and what she’ll look like. Will she remember me? Will she remember that afternoon, playing hookie and sucking my cock behind the stadium? After all these years, she still makes my cock ache. And my heart too…just a little.