I Slept With My High School Crush And She Had No Idea Who I Was


My friend Joe had been trying to set plans to go out in celebration of his job promotion all week until we finally landed on a Friday night at a local club. Since my apartment was only a few blocks away, everyone drove to my place and we walked over.

I was never a big drinker, but I promised Joe that I would celebrate with him for his night out; and to Joe, “celebrating” did not involve being sober. There was a light chill out, so a few of us brought jackets. I decided to tough it out in a black dress shirt — with the sleeves rolled up, no less — and jeans.

Once everyone checked their coats, we headed to the bar, where Joe immediately instructed the bartender to line up six shots of Fireball. “No, man, I’m good on shots,” I told him. “Dude, what the fuck? You said you were drinking tonight; don’t puss-out,” he snapped.

“I am, I just don’t want to take shots; let alone shots of Fireball.” Trying to negotiate, Joe made a counteroffer, “OK, just do this round at least.” I reluctantly obliged, forcing down the disgusting cinnamon-flavored concoction.

The DJ started playing and the girls were pulling Joe and Vinny to dance. “C’mon, baby, dance with me!” Denise begged Joe. “Not right now. Go with Zach; that fucker always likes to dance.” Denise and Allie looked over at me, and I happily obliged.

Somewhere between “Uptown Funk” and “Sugar,” I spotted an incredibly attractive blonde just over Allie’s shoulder. It was tough to get a good look at her between the strobe lights, but it was good enough to see that she was extremely good-looking.

I saw her make her way to the back bar, so I asked Allie and Denise if they wanted something to drink. “Vodka cranberry,” Allie said. “Long Island,” Denise said. I maneuvered my way over, then pulled up next to the blonde. I recognized her instantly.

She didn’t have to tell me, but her name was Jillian, and she was the object of affection of every guy at my high school, including me. Blonde hair, gorgeous blue eyes, year-round tanned skin, head cheerleader; something out of a Nicholas Sparks novel-turned-movie.

We talked a little bit in high school, but we never hung out socially.

“Vodka cranberry,” she ordered. The bartender looked at me, but I paused for a second. “Sorry about that — a bay breeze, a Long Island, and uh, um, a vodka cranberry,” I said, looking at Jillian.

“Good choice,” she said, looking back. “You’ve got good taste,” I said, smirking. “Are those all for you?” she inquired. “The LIT is mine, the bay breeze is for my friend, and I just planned on holding the vodka cranberry until you were done with yours.”

It was a complete risk, but I figured I had nothing to lose.

She laughed, in a good way.

“So what, you just planned on giving your friend their drink, drink yours and then come find me when you saw I was done?” she said, playfully. “Well, you’re right on the first two, but I was hoping you’d like to dance — if your friend doesn’t mind, that is,” I said.

“What makes you think I’m not here with my boyfriend?” she said, tilting her head and squinting her eyes above a small smirk. “Four things: For one, no girl comes to a club alone. Secondly, you would’ve flat-out said you had a boyfriend. Thirdly, if you did have a boyfriend, he should be up here getting your drink for you.”

“And the fourth?”

“You’re still standing here.”

She chuckled, then told me to drop the drinks off to my friend and meet her. “By the way, I’m Jill.” Part of me as hoping that she actually knew whom she was talking to, but when she made her introduction, it was obvious she had no idea. Rather than burst the bubble, I smiled and shook her hand. “Zach.”

We danced for about four or five songs before the DJ started working in the throwback slow jams. I was about three-quarters of the way through the Long Island when “Poppin” started mixing in and I tossed it out to pull her closer.

Our legs locked in between each other’s and our hips were swaying to the beat, the sexual tension kept rising with every second we kept our lips off one another. The DJ mixed in “Pony” by Ginuwine, and I almost instantly wrapped my forearm around her waist and pressed her body against mine until we were nose-to-nose.

I leaned in and kissed her neck as she gripped the side of my shirt once my lips touched her. I went a little higher, kissing her just underneath her ear and I could feel her breathing heavily into mine. I pulled back to look her in the eyes. I slid my right hand down the small of her back to grab her ass and she took a deep breath.

Her ass tightened in my hand and her eyes were screaming at me to kiss her. I pressed my lips against hers, then twirled my tongue around hers. Her hips were gyrating against mine, so I asked if she wanted to leave.

She bit her lip, and nodded. I told her my place was nearby, so I told her to let her friend know while I told the girls that I was leaving. I hailed a cab outside of the club and gave him the address. I was doing my best to be on my best behavior until we got there, but she kept biting and licking my ear, making the task that much more challenging.

Within minutes, we pulled up to my place. The ride was a little over five bucks, so I gave him a $10 and got out of the cab. The second we walked through my door, she pinned me against the wall.

I slid my hands into her back pockets as we kissed, then lifted her up and turned around so that she was now against the wall. Still wrapped around my hips and kissing me, she started unbuttoning my shirt without looking at a single button.

When she undid the last button, she pushed the shirt over my shoulders and down my forearms. I put her down and took her hand, guiding her to my bedroom. She sat me down on the side of the bed, then proceeded to removed her shirt and wiggle out of her jeans in what seemed like slow motion. She stepped toward me and pulled my tanktop over my head, tossing it behind her once removed. She lifted her leg onto the bed, then lifted the other so that she was now straddling me in nothing but her bra and underwear.

I wrapped my left arm around her as my right hand slowly glided along the middle of her back while kissing her neck. I gripped her tighter as I unhooked her bra and slid it off her body.

I turned and tossed her onto the bed as I sat up to grab a condom out of my nightstand. Jill started undoing my belt and jeans as I reached over. Once my clothes were off and the condom was on, I leaned in to kiss her. I started to slowly thrust against her pussy until she reached down to stroke my cock before sliding it into her.

She let out a long, deep sigh, then wrapped her legs around me. I grabbed her left hand with my right and continued to slowly thrust. She kept breathing heavily and gripping my hand harder through the first few strokes, so I made sure to keep going slow until she was more relaxed.

When the pressure of her hand eased up, I started going deeper in her. She broke her hand from mine and grabbed the back of my neck to pull me down and kiss me. “You can go harder,” she whispered. I grabbed her left leg and placed it on my right shoulder before complying with her wishes.

Rather than muffle the sound of her moans by kissing her, I moved my lips up and down her leg, allowing her sighs and groans to fill the room.

Remembering her cheerleading background, I pushed down on her leg until it was sandwiched between us and we were nose-to-nose again. “What about the other?” she sighed. “You’re right. How inconsiderate of me.” I reached down and pulled her right leg up until I was sitting over her with her legs by her ears and her ass in the air.

“Now fuck me,” she commanded. I smacked her ass with my right hand, causing her to twitch, slightly. I kissed her, while tugging on her bottom lip as I pulled away.

I grabbed her ass with both hands and proceeded to fuck her deeper and harder. Her sighs turned into groans; her groans turned into moans; and when I found my rhythm, her moans turned into screams.

She reached her right hand around my neck and yanked me down to kiss me. I stuck my left hand out to keep balance while keeping my right hand clenched to her ass. “Oooh, right there,” she moaned. “Right there,” she groaned. “There,” she panted. “There. There. There!”

I could hear the vibrations in her breathing as she came.

Both of our chests were glistening with sweat. She ran her tongue along my neck before biting down, and for whatever reason, it turned me on. “Mmm you taste good,” she whispered. “Do it again,” I demanded. “Are you going to cum?” she asked. “Yes, but not before you do that again.”

As soon as she pressed her tongue against my neck again, I started to thrust harder. The slower her tongue rolled along my skin, the harder I fucked her. I heard her whisper in my ear, “Cum for me.” I was panting now. “Cum. For. M—,” and she bit down on my neck as I started to cum uncontrollably.

Both of us struggled to catch our breath afterwards, as we lay side-by-side. I looked at her, already knowing the answer. “Water?” “God, yes,” she panted. I started to sit up and she climbed on top of me and pushed me back down to the bed. “Where are your manners? Ladies first,” she smiled, leaning down to kiss me.

Neither of us wiped the sweat off of our chests, so when we walked to the kitchen, there was an extra chill in the air. She hollered from the hallway, “Ah, can you grab a sweater or something? I’m freezing.”

I headed back to the room, sifting through my closet. As I reached the end of the wardrobe, I reached in and grabbed something. I tossed a red sweater on and walked into the kitchen.

She was facing the window looking outside, so I came up behind her and placed a jacket over her shoulders and hugged her. I could see her reflection in the window that he eyes were closed and that she was smiling.

“Oooh, that feels nice!” she said. “Me, or the jacket?” I said. “Well, both, but more so the jacket,” she cracked. She slid her arms through the sleeves, which is when she opened her eyes and saw the distinct maroon and white lines — our high school colors — around the cuffs.

I saw her eyes look down at the colors, as she started piecing it together. “Wait a minute…” she said. She pulled the inside of the left lapel and looked down to find “Armstrong” stitched over her left breast.

She turned around, quickly, then looked at me as if she was seeing me for the first time that night. I guess, in theory, she was. Thought Catalog Logo Mark

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