The girl who wouldn’t touch me in high school [MF]

I couldn’t believe it when I saw her at the one bar in our hometown, with a group of her friends, some of whom I recognized, some of whom I didn’t. The girl who tortured me for the entire four years of high school. She always flirted with me, we studied together all the time, it was to the point where my mom assumed we were dating. But we weren’t, we very much weren’t, and it was a bit of a shock to my mom that I had to invite someone else to prom.

In high school, Kendall was the perfect girl – beautiful, rich, and smart. She was in all the AP classes with me, that’s how we came to study together. Me, I was a nerd, to my core. I may not have looked like one, per se, but I was, no doubt about it. I read history books for fun, I devoured baseball statistics like I was Bill James. She wanted my help for her homework, and I was naive enough to think she wanted to hang out with me otherwise.

I wasn’t a bad-looking guy in high school, tall and skinny, with blond hair that fell down over my ears in an unfortunate haircut because my mom said it looked good and no one ever told me any better. But I was so awkward around girls, it was painful, looking back. School dances, while I still went, were rough experiences, and I didn’t do any better with girls the rest of the time.

So when a girl like Kendall, by far the smartest of the popular girls, asked me if I wanted to study with her, of course I did. Girls like her didn’t talk to guys like me, except she seemed different. She was more intellectual, less ditzy, she seemed to have more substance. That being said, it didn’t take me long to realize that this friendship was one where I helped her get good grades and she provided me some social capital by associating with me – nothing more. And I was naive enough to keep doing it. I thought if she could just get to know the real me, she’d see through the bullshit high school social dynamics.

But that never happened. She dated a string of popular boys, spending most of senior year with the football team captain, a good-looking guy and a hell of a football player, but not much up there, you know? And then we graduated and that was it. She went off to USC and I went off to an Ivy League school, and she checked in on me a few times freshman year, but we soon fell out of contact. I think I’d seen her once or twice, max, since we left for college.

But there she was, standing at the bar, in all black down to her black booties, her brown hair falling down her back, over her leather jacket. I hadn’t seen her in years, but it was unmistakably her. I couldn’t forget that doll-like face with the piercing brown eyes, the full lips, and her nose, thin with an uplifted tip. When she smiled, it was that same infectious smile with which I’d fallen in love naively, all those years ago. She hadn’t changed, just gotten more beautiful as her features matured and she filled out her body. Even in her mid-twenties, she was still as thin as ever, but her Instagram pictures showed me that she’d gotten amazing, full tits and a toned, round ass, both of which seemed impossible, given the size of her waist.

I was home for the holidays, and I was out with a friend, watching the Warriors game (this was the 73-win season), and we needed to get a couple more beers, so I offered to go to the bar to get them. That night, I wore a navy Barbour jacket over a gray hoodie, with dark skinny jeans and Stan Smiths. I got to the bar and ordered us a couple more Sierra Nevadas when I heard a familiar voice.

“Oh my god, Paul, is that you?”

I turned and there she was, flashing that infectious smile, pushing a lock of hair back behind her ear. She hugged me.

“It’s been so long!” she said. “How are you?”

“I’m good,” I said, shaking my head in disbelief. “Just home for the holidays.”

“How’s your family?”

“They’re good, nothing ever changes with them. What are you up to these days?” I asked her.

“Just living in SF, got a job in tech. Nothing fancy.” She looked at me quizzically, “I feel like you’re not around here.”

I ran my hand through my hair. “Yeah, no, I live in New York,” I told her matter-of-factly. “Finished law school, got a job out there.”

She looked impressed. I shrugged, trying to appear as casual as I could, “I miss California, you know, but I love New York.”

“So you’re a lawyer, huh?” she asked. I nodded. “I hear that’s a lot of work,” she said inquisitively.

“Oh, it’s not so bad as people make it seem. I get everything done. I worked in our SF office this week.”

Even in this conversation, her demeanor towards me wasn’t like anything she’d ever been before, even if it was years ago. See, I’d definitely grown up in those years. My frame had filled out, and I managed to fit time in the gym every day into my busy schedule. My jawline had hardened, and my facial hair had filled in enough to let me leave a healthy amount of stubble on my face. And most importantly, I’d learned how to dress and cut my hair. I wore it longish on the top and short on the sides. I looked different, and I acted different too. I’d grown up. It sounds stupid, but I knew I belonged in a conversation with a woman like her, rather than only being there by virtue of her charity, which is how it used to be.

We caught up for a couple of minutes, then she said she had to get back to her friends.

“But it was so nice to see you!” she told me. “It’s been so long! Let’s be in touch, your number is still the same, right?”

“Yeah, yeah, of course,” I nodded. “That would be great.”

Normally, those words combined with that enthusiasm means the person is entirely bullshitting, saying that to extricate themselves from a conversation, with zero intention of following up. And past history with her told me that she couldn’t possible mean it.

But I don’t know, there was something about her this time that made me think that she might just mean it. She seemed genuinely interested in hearing about my life and she hadn’t immediately reverted to treating me like the immature nerd who was obsessed with her. She’d treated me like a man.

The next day, I got a text from a number I didn’t have saved, “Hey :) it’s Kendall, remember me?”

Okay, so she hadn’t been bullshitting. Over the next few days, we texted back and forth, and the messages were very flirty. I loved that I was flirting with this beautiful, smart, successful woman, the fact that we’d known each other in high school was merely incidental – a starting point, not relationship-defining in any way.

That Saturday, the night before I was going to leave back to New York, I got a text from her, “Hey, my friends and I are going out in SF tonight, I know you’re home, but you want to come into the city and meet us?”

Fuck, no, I thought to myself. That invitation was an invitation to go out, but it sure seemed like the invitation to so much more. That was my chance, I’d thought about her all the time since I saw her a few days before, and it could’ve been a reality. Except, that night was my brother’s birthday, and my mom had made plans for us. There simply wasn’t enough time to get through that and make it to SF in time to see her.

So, with great regret, I sent a text back, “I’m so sorry, but I can’t, it’s my brother’s birthday and my mom has plans that I can’t skip…”

I immediately got a sad face and text asking how long I’d be in the Bay. I again regretfully had to say that I was leaving the next day, I had to get back to work.

That elicited another sad face and a message saying that’s too bad. I know, I told her, and I threw out a line that I figured would never get any bites, that if she was ever in New York, to please hit me up.

Surprisingly, we stayed in touch over the next few months. Not every day, mind you, but a decent amount. We’d complain about our jobs, send each other Snapchats, swap interesting going out stories, just general staying in each other’s lives. Every Snapchat I got, every Instagram post of hers I saw, I was reminded of how beautiful she was.

And then on a Monday in May, I got the text I’d hoped would come, but didn’t think ever would.

“Hey, it’s last minute, but I’m gonna be in New York later this week for work. You around? I’d love to see you”

“Hey! Yeah, of course. Let me know when you’re here, we’ll get together”

She was coming on Wednesday, so we made plans to get together on Thursday after work. Thursday I wore a suit to work, which I don’t normally do. I wore my navy suit which brought out the color in my eyes, and I made sure to get my brown shoes shined at lunch.

I finished my work at 8:00, we’d already established it might be kinda late. I asked her if she wanted to grab dinner, or drinks later. She said dinner would be great. So it was a date date then, even better.

We met at one of my favorite restaurants in the city, an upscale Italian place in the West Village. I got out of the Uber and there she was, standing on the sidewalk outside, waiting for me. She was simply stunning, in a white blazer over a dark blouse with flowers on it, tight light jeans, and suede booties. Her hair fell down her shoulders, with the slight curl at the end that I figured had taken her a little while to perfect.

She smiled when she saw me get out of the Uber, that smile that made men fall in love, her pink lipstick bringing out the color in her cheeks. She tucked a bit of hair behind her ear and smiled modestly, the motion exposing a diamond earring.

“Hey,” she said, her tone matching the warmth of the evening.

I hugged her, “It’s nice to see you. Let’s go inside.”

We sat down upstairs and each got a glass of wine. We took our time with the food, each having a couple glasses of wine, and got to really catch up in a way that we hadn’t in the bar in our hometown or over text.

She’d dated a guy her last couple of years at USC and tried to make things work long-distance when she moved up to SF, but in the end, just hadn’t seen him as the guy long-term for her. I told her honestly that I hadn’t really dated anyone since I moved to New York, I could’ve sustained a relationship with my job, but I wasn’t sure I could start a relationship.

Our conversation flowed easily and naturally, there wasn’t any awkwardness at all. She made me laugh, she made me smile, she made my cock hard in my pants. And from what I could see of her, I made her laugh and smile too. When the check came, I got the sense that she wasn’t ready for the night to be over. I sure wasn’t.

“It wouldn’t be New York if our night ended at 9:30, now would it?” I asked her as I signed my name on the receipt.

She smiled, “No, it most certainly would not.”

“Let’s go then.” I had a lounge in the East Village that was perfect for an occasion like this. We Ubered over there, ordered drinks, and sat next to each other on a couch, continuing our conversation into each other’s ears. Her perfume smelled intoxicating, and I could feel the warmth of her leg against mine and the light touch of her hair on my neck as she leaned in.

I knew where this night would end, but it didn’t mean that I wasn’t a little nervous to take this next move. My arm around her head, I gently tilted her face up to mine as I leaned down and kissed her, those full lips warm and wet against mine. She returned my kiss with no hesitation, and I felt her hands reach up and grasp the sides of my face as our tongues danced against each other. The chemistry was there instantly. You ever kiss someone and from the first touch are on different pages? We were the opposite of that, it was as if sparks were flying from the moment our lips touched.

“Wow,” I pulled away from her and took the final sip of my drink. I kissed her again, and whispered into her ear, “I think the next drink should come at my place…”

“Yes please,” she whispered back. I paid the bill, and we were on our way.

Soon enough, I was opening the door of my apartment, holding her hand as I led her inside.

“This is a nice place,” she said, impressed. “This is not some bachelor pad. You’re like a real adult in here.”

“At least I try to be,” I admitted. I took her coat and hung it up, she walked over to the window and looked out it, enjoying my view of the city.

“You must pay a fortune for this place,” she said in amazement.

I came up behind her and stood against her, feeling her round ass against my crotch, my hands reaching up to lightly massage her shoulders as I stood over her.

I laughed. “Believe me, I do. You live in San Francisco and even you might not believe it,” I whispered in her ear as I kissed her neck softly.

“Mmm,” was all she moaned in response. I could feel her ass start to grind against me, my cock growing with every move she made. I kept up what I was doing, my hands rubbing her shoulders, my mouth exploring her neck, my stubble scratching her skin.

“Mmm, Paul, that feels so fucking good,” she let out quietly. I slid my hands down her body, reaching forward to squeeze her tits and pull her body even closer to mine, sliding them further down to grasp her hips. By now, my cock was rock hard in my pants against her. Still grasping her hip with one hand, I reached one hand up and grabbed her hair with one hand, titling her head back to the ceiling as my kisses dove forward to her collarbone and chest.

“Yes, ahh,” she let out a long, deep exhale. I spun her around, my body pressing her against the windows. The coolness of the glass was refreshing on the warm, early summer evening as two bodies pressed against each other. Still with one hand in her hair and the other now grasping her round ass, I leaned down and kissed her. Each new kiss was better than the last as we explored our chemistry with each other. Incidentally, AP Chemistry had been the subject she struggled with most in high school, but in this moment, that was neither here nor there.

I reached the hand on her ass up to feel one of her perfect tits through her blouse. Now with both hands, I unbuttoned the blouse, my fingers niftily sliding it down her arms. I reached behind her back and did the same to her bra, letting it too fall to the floor.

I took a step back and appreciated her body as I unbuttoned my own shirt. Those tits, impossibly large and perfectly round, firm yet with the bounce of a still-young woman. Her stomach, flat as a board, punctuated by her belly button piercing. Her waist a man’s dream, her sides diving in to form little inverse triangles before jumping back out for her wide hips and round ass. And that face, gorgeous as ever, her eyes staring hungrily at me as I took my time unbuttoning and shrugging myself out of my shirt.

I knew what she was looking at. This wasn’t the body I had in high school. I wasn’t a model or anything, but I’d filled out my frame. I always had broad shoulders, but in high school, I was a stick otherwise. Now, those shoulders had some muscle to them, and my chest and abs reflected my time in the gym. I even had a tattoo on the inside of my arm that I never would’ve thought of getting in high school.

I’d lied a little when I said I was done with work at 8:00, it could’ve been 7:00, but I spent that time in the gym, betting that I’d have this exact moment later. She grew tired of looking at me, and stepped forward to embrace me again, reaching her hands up and running them through my hair as she kissed me.

I took her hand and led her to the bed. She saw my tattoo, “What’s this?!”

I laughed, “What? I can’t have a tattoo?” I paused, “It’s for my grandma.”

She looked at it closely, “That’s sweet. It fits you, actually. I like it.”

She smiled up at me. I kissed her and we both reached for each other’s pants simultaneously, them first, and then her black lace panties and my briefs. There was no need to move our hands, I reached for her pussy, finding it dripping in anticipation of my fingers. As I slide them inside her, she moaned and reached for my cock, stroking it softly.

With a gentle motion, I pushed her down onto the bed and crawled over to her, her pussy glistening even in the dim light. She moved to kiss me, but I put a finger to those beautiful lips, instead kissing her neck again, she lifted her head to give me more room. I kissed down her chest, taking my time, before I finally got to her tits.

I kissed everywhere but her nipples, teasing her, she strained to bring them to my mouth. Finally, my tongue touched her nipples lightly, one then the other. She moaned again, the teasing relieved. I continued down her stomach, until I reached her slit. I ran my tongue up and down her lips, only adding to the wetness.

I flicked her clit with my tongue and I felt her twitch. I enclosed it in my mouth, my tongue running back and forth over it, starting slow but building in pace, as I slid two fingers into her. As my pace built, she started to moan louder and grind her pussy against my tongue. As she got close, I sped up even faster, reaching my hands up to twist her nipples between my fingers as she squeezed my face between her thighs, her hands pulling my hair, her body spasming into an orgasm. I looked up and she was shaking, her back arched, hair splayed across the bed, head tilted back.

She looked down at me and pulled my face to hers, “Fuck, Paul, that was so good.”

Kendall pushed me off of her so I was lying on my back up against the pillows. “My turn,” she told me, grabbing my cock in her hand. She licked around the head, she licked up and down the sides. I was practically jumping in anticipation, I’d never had a woman tease me like that. Finally, mercifully, she took me in her mouth, those sexy lips opening to take me in. She slid me deep into her mouth, easily taking about half of my seven inches. All I could do was throw my head back and enjoy.

“Wow,” I told her as I pulled her up to kiss me, my hands clasping her ass. “I didn’t think you could be any sexier.”

“Got a condom?” she asked.

“Top drawer.” I pointed to the bedside table. She tossed one to me, I rolled it on. She kissed me, one hand caressing the side of my face, my hands grasping her hips and slowly sliding my cock into her.

“Ahh,” we both let out as we adjusted to each other. She felt amazing – warm, tight, wet for me. She bounced herself very slowly on me, flipping her hair across her face, then holding onto my shoulders.

“Yes, yes,” I moaned quietly as she sped up, leaning over so only her ass moved, twerking up and down on my cock, her hair and those wonderful tits in my face, my hands ostensibly holding her hips but really letting her do the work. She varied the tempo, speeding up and slowing down, taking me in long, deep strokes, moaning all the while.

She sat up, flipping her hair behind her head, arching her back to stick that perfect ass out, and reaching down, her hands pressing into my chest. Still holding onto her, I let her grind her pussy on me, my cock filling her, her clit sliding across my skin.

“Fuck, Kendall, that feels so good, don’t fucking stop,” I told her, leaning forward to take her nipples in my mouth. Her response was a series of unintelligible moans as her lips gripped my cock tight. Every inch of her was perfect, I was in absolute visual and sensory heaven. She kissed me, her hair forming a cave around our joined mouths.

Now it was my turn. I pulled her all the way down to me, my arms wrapping around her back, her hands grasping my face as we kissed. I thrust into her from below, my cock slamming into her round ass. As I sped up, her face broke away from mine and she moaned, “Yes yes yes Paul yes!”

Faster and faster I went, her moans got louder and louder. So did the slaps of my body against hers and my grunts from the exertion. I reached down and slapped her ass, hard, which only made her moan louder. I pulled her back up so she was straight above me, still fucking her hard from below.

And that was the sight that did me in: me holding her tight body over me, my cock thrusting in and out of her pussy, her tits bouncing wildly with every thrust, her face contorted in pleasure, her moans filling the room. I felt myself getting close.

“Oh god, oh god,” I repeated, and with a loud grunt, I finished, filling the condom with my cum, her body twitching with every spurt. I pulled her down to kiss me, and this kiss was wet, sloppy, and desperate in the way our mouths attacked each other. We just lay there on each other, catching our breath, our hands intertwined, intermittently kissing each other.

“Wow, Kendall, that was incredible,” I said. I smiled up at her, “I’m really glad you came to New York.”

“You’ve sure been a generous host.” She smiled back, her hands gripping my face, her beauty not marred in the slightest by the sweat on her brow and in her hair.

“And not bad in here, either,” she added, biting her lip at me.

She got introspective, “You know, in high school, while we were studying, I don’t think I imagined being in your apartment in New York City having just had amazing sex.”

I raised my eyebrows, “No, I don’t think that would’ve been too likely. I sure thought about it though.”

“You were cute back then. I’d say you grew up, ” she laughed and kissed me.

We got out of bed and threw on sweats. She looked simply incredible wearing one of my t-shirts and her panties, her hair messy from sex. It was late, and we soon fell asleep, the lights of the city flickering through the window.

Source: reddit.com/r/gonewildstories/comments/7jzkhy/the_girl_who_wouldnt_touch_me_in_high_school_mf