To boil down the situation I found myself in, Maddy Perez was the captain of the cheer squad and the most popular girl in my grade, most likely the whole school.
Meanwhile, Nate Jacobs was the captain of the football team despite being a junior and definitely the most popular guy in school.
They started dating last year, becoming the equivalent of a power couple, whatever that amounted to in high school.
Though the cracks started showing within a few months of them being together, soon followed by their first official breakup, then they got back together, and then they broke up, over and over and over again.
Right now, it was clear from how the two of them were behaving that they had just broken up and were both desperately trying to make the other jealous and angry.
I found the whole thing pathetic, but I was more than happy to play the hand I had been given.
After all, there was a reason why Maddy was the Captain of the cheer squad.
To say it plainly, Maddy was beautiful, but specifically the kind of beauty that everyone could appreciate.
She had dark raven hair that came down to her shoulders, full lips, tan skin, dark brown eyes, and a slim but curvy build, barely reaching 5’3.
Of course, out of all her physical attributes, the real thing that gave Maddy her charm was her confidence.
I could see it in the way she moved her hips side to side and ran her hands up and down her body.
It wasn’t in an effort to draw attention to herself, because Maddy understood that she didn’t need to do anything to get anyone’s attention other than existing.
Which is exactly why I needed to be different from everyone else.
Slowly, I stopped moving to the music, and it only took a second for Maddy to glance back at me with a frown, “What are you doing?”
“I’m bored,” I muttered with a sigh as I glanced away from Maddy, “I thought your boy would have made a move by now, not just stand over there in the corner.”
“Wait, you wanted to fight him?” Maddy looked at me as if I was crazy, and she was right too; I very much was.
“Would have been more memorable than just dancing,” I admitted with a shrug.
“What, was it not exciting enough for you?” Maddy asked with a cutting tone as she turned around to glare up at me.
I smirked, “You’re not the first girl to throw some ass on me.”
Maddy paused for a second, and I saw her glance outside before looking back to me, “Yeah, you ever go swimming with any of those girls?”
“Good,” Maddy said with a note of finality as she grabbed my wrist and turned around, carving a path through the house that had us pass right by Nate, who stared her down with an obsessed look in his eyes.
Reaching the poolside, Maddy reached down and pulled off her pink halter top and skirt, revealing the matching set of pink lingerie beneath.
Instead of admiring her body, I acted as if nothing had changed and started to undress myself, reaching down and pulling off my hoodie and tank top, revealing the physique I had spent all summer crafting.
Even without looking, I could feel Maddy’s eyes on my body as she snuck a glance that I pretended not to notice as I undid my belt and stepped out of my jeans, leaving me in just my boxers.
Again, I felt Maddy’s gaze on me, but this time she lingered for a breath longer, no doubt noticing that I was blessed with more than just chiseled abs and broad shoulders.
Ignoring her again, I instead turned to face the pool and, with two quick steps, dove into the water.
Letting my moment carry me into the middle of the pool, I floated for a second, enjoying the silence and weightlessness, before I stood up and breached the water.
Hanging my head, I reached up and pushed back my hair that had come loose from its bun.
With my vision clear, I looked back and found Maddy still standing next to our clothes, staring at me with those dark eyes of hers.
That was when I let myself fully appreciate her body, slim and curvy; her hips supporting a nice round ass that I couldn’t help but picture sinking my teeth into.
Even her chest, which was on the smaller side, I wanted to squeeze, kiss, and tease until she broke down in my arms.
I then looked back up into Maddy’s eyes, making sure that I knew that she had noticed me checking her out, and I didn’t give a damn.
“You getting in or are you gonna run off with my clothes and leave me out here?”
“Why would I do that?” Maddy asked sarcastically as she started walking towards the stairs leading into the pool.
“I don’t, maybe to get back at me for calling you boring,” I guessed as I watched Maddy walk gracefully down the stairs, the water moving further and further up her body until she pushed off and dove beneath the surface.
I watched her beneath the water as she glided towards me, swimming languidly with her slender legs gently kicking behind her.
When she was less than a foot away from me, Maddy came up, and I got to watch as the water slid off her smooth skin and through her dark hair, leaving it slicked back and her face completely bare.
Wordlessly, she reached out and wrapped her arms around my neck while mine went around her waist, “Am I still boring you?”
“Why do you care what I think?” I countered with a sly grin even as I pulled her closer, “I thought this was about making your ex jealous?
It’s working, by the way.”
Maddy glanced over her shoulder and found Nate staring back at her through the window, making her smile, “Well, do you know what would really make him jealous?”
“That depends,” Maddy said, her voice dropping into a sultry octave as her legs wrapped around my waist and she pressed her lips next to my ear, “Would you fuck me right here and now?”
I was honestly surprised by how quickly my boxers went from breathable and supportive to constrictive and painful as every drop of spare blood in my body shot straight into my dick.
“I’m not sure you want to do that,” I replied, taking Maddy by surprise, as I doubted anyone had ever responded with anything but an overly enthusiastic yes, “Most girls already have a hard enough time handling me even after I make sure they’re…ready.”
Maddy scoffed and rolled her eyes, “Boy, that’s some straight bullshit.
What, you got seven maybe eight inches and think you’re some sex god-”
I interrupted Maddy as I grabbed her ass, pulled her flush against me, and watched as her eyes went wide.
Now it was my turn to whisper in her ear seductively, “Try twelve.”
Before Maddy could respond, my lips found the nape of her neck and gave her a tiny bite, making her gasp involuntarily as she flinched, inadvertently pressing herself against my hardness.
“Ow, what the fuck?
That hurt!” Maddy swore, but as my fingers and lips continued to explore and roam across her skin, I started to hear a distant voice in my head, whispering Maddy’s unspoken wants and desires, finally giving me the chance to put my theory to the test.
One of my hands left Maddy’s ass and instead moved up her back, gently cupping the back of her head as I pressed my lips against hers with a tenderness that I knew caught Maddy by surprise.
I could tell at first she wasn’t a fan of it; I was kissing her like a lover, not some guy she just wanted to hook up with to make her ex jealous.
But I persisted, and as the seconds trickled by, I felt Maddy start to lean into the kiss, tilting her head to the side and letting our lips lock.
She started to grind against me as well, and even underwater I could feel the heat pouring off of her pussy.
Unable to resist, my hand left Maddy’s ass and dove between us, quickly reaching the front of her panties only for Maddy to grab my wrist and pull away from the kiss, “What is this freshman year?
I asked if you wanted to fuck!”
“Fine, I was just looking out for you, but if you’re that eager, guess I don’t need to be concerned.”
With a sharp tug, I pulled down my boxers, freeing my hard-on that came to rest against Maddy’s stomach, dragged down through the water by its impressive weight.
“Fuck.”
Maddy’s swear was one of disbelief and shock, whispered under her breath and certainly not something she meant to say aloud.
But decided not to say anything, I was too preoccupied as I pulled Maddy’s panties to the side and lined up the head of my cock with her pussy before thrusting forward with my hips, sinking the first three inches of my cock into Maddy’s tight, warm depths.