Senior Year Memories Ch. 24

"Don't fuck with me when I'm horny," Sarah said, rocking against my face.

"Totally," Brooke said. I felt her reaching down, and a strange change in pressure on my cock before she added, "I think that needs a prize, and since this is all I got, I think it's worth it; whaddya say, Rookie? It's still got a tonna lube!"

"Only if Ryan puts it in," Sarah said, handing the prize to me.

Brooke's butt plug. If my mouth were less occupied, I'd have quipped about this being a sacred, rare honor held for only the highest of occasions, but since I couldn't, that joke's only for you, dear readers.

Sarah bent over to better present her ass to me, and if the sounds of smacking lips were any indication, she was making a fair feast of Brooke's bouncing tits. With her tight, winking asshole perfectly on display (and knowing just how perfect it was), I had no problem sliding the slick toy into her slowly, tantalizingly, making her enjoy every second of its insertion until it passed the most flared out bit and settled inside her tightest of holes.

She groaned in appreciation, then said, "Thank you Ryan... Brooke... that's... heavenly."

"Oh, this is fucking bullshit," Gwen proclaimed.

"All you gotta do is apologize to the Rookie," Brooke squealed, rocking her hips to take me from a slightly different angle.

"I don't apologize," Gwen said.

"Then you totally don't get fingerblasted!" Brooke declared. To help out, I crossed my arms across my chest defiantly.

"That's not fair!" Gwen exclaimed.

"It's an orgy, we all make our own rules," Sarah said.

"'cept for the no shoes in the house thing, that's Dakota's rule," Brooke said.

"Right," Sarah agreed.

Gwen grumbled. "Seriously, this is how it's gonna be? You're a guy down, you got a big cock, you honestly gonna tell me you'd rather these two tiny bitches take you on rather than have all I got?"

I nodded under Sarah's pussy, never once letting up in my onslaught.

"Fine. I'm sorry, okay? I'm just teasing the new girl, I didn't mean to be such a bitch and try to steal your thunder or anything. I was just having fun. Can I please join you two and fuck the nerd with you?"

"He's got a name!" Brooke said defensively.

"Fine, can I fuck Ryan with you?" Gwen said.

"Well, what do you think, Ryan?" Sarah asked.

I thought it sounded like a pretty disingenuous apology, but having dealt with a fair number of girls all across the bitchy spectrum, I thought there might be something that could be done with fair Gwen Savage. Maybe not now, but definitely some fun could be had later.

Kindly, I extended a hand for her to sit on.

"Finally..." Gwen grumbled, crawling over and onto my hand. "...the things I gotta put up wi-OH, FUCK!"

In spite of her being a bitch to my friends, I still wanted to give a good impression and fingerfuck her nice and good. The way she was gyrating needily on my hand and moaning without restraint, it sounded like it was working.

"See, it's pretty nice when you're nice, ain't it?" Brooke asked.

"Oh, fuck off," Gwen replied.

"Can we just... oh god... can we just shut up and enjoy this...?" Sarah said, echoing something that sounded pretty fucking nice to me at the moment.

Though there was still some brief grumbling and arguing, it wasn't much more than token at this point as the three ladies ground and rode, cooing and moaning and groaning and trying to get off. When I felt another pair of hands gently take my unused hand and stretch it out, sitting down on my fingers and settling a soaked pussy onto them, I wasn't too surprised.

"Thanks, Ryan," the kind voice of Jade Alvarez said. "For coming, for this, for everything..."

There's a good chance I might've given her a little more in the way of fingering than Gwen at this point, but it's hard to be sure.

Now, I'm not sure how many of you reading this it has happened to (and I doubt it's many, but if it has, hey, mazel tov to you!), but, while having four hot, naked girls on top of you at once is pretty fucking awesome, it's got its share of downsides too. Perhaps the biggest among them is how much like rubbing your stomach and patting your head it can be. When you're focused on getting four girls off, it can be hard to give every one equal attention, while focusing on my pleasure was next to impossible. Don't get me wrong, in my head I was in fucking heaven, but even with Brooke's best efforts I knew it would take some extra time and focus to get off.

Instead, my efforts were focused on the ladies above me, trying to guess which one would cum first.

That Brooke, with a squeal and a squirt and a lot of "yesyesyesyesyes!" was the first wasn't a surprise, since she'd been at it the longest.

That Gwen came second... well, was a little bit more of a surprise, but not by much. I'd considered toying with her, keeping her for last to motivate her to be nicer, but realized that showing her what she could have if she really played ball would be an even better strategy. With my fingers buried deep in her steaming cunt, she came hard, writhing and moaning like a pornstar as her juices covered my hand.

Sarah was unsurprisingly next, and as usual when she cut loose she was a pure surprise for how much energy and vulgarity she brought to the table, riding and squeezing my head between her thighs as she screamed a truly impressive diatribe of expletives.

Late to the party but never late for a cum, Jade was last, a more subdued but no less pleasant orgasm.

The four of them disentangled themselves from me, allowing me to see again, and to kiss four absolutely lovely ladies. Sarah kissed sweetly, Brooke perkily, Gwen quite nastily, and Jade long and lingering. The beautiful Latina with the caramel skin, curvy, lean body, DDD tits and lusciously large ass was someone I owed a lot to, and one I didn't mind making out with a bit.

"You taste good, though that's probably Sarah, isn't it?" Jade asked, amused.

"Probably," I confirmed.

"I want to have a lot more fun with you before we're done here," Jade said, her voice husky and full of promise.

"That can be arranged," I said.

"Hey, get in line; that cock's still hard and you ain't the only one who wants a ride," Gwen said.

"Yeah, I'm, like, happy and all for what I got, but I really wish you'd filled me with cum for how much you got me goin' there, Ryan," Brooke said, jacking my slick cock. "We gotta do something about that."

"HEY, GUYS, CAN ANYONE, LIKE, HELP ME HERE!"

The plea for help came from the hallway leading further into the guest house, from a 5'4", petite Asian girl. Completely naked, I could see every inch of her tanned, tight body, from her A-cup tits with their dark, pointed nipples, to her toned abs and the trimmed landing strip of dark hair leading to her engorged and clearly wet pussy lips. Her face, with her big dark eyes, tiny nose and full lips, all framed by shoulder-length black hair, would undoubtedly have been cute at the best of times, but for now appeared quite distressed.

Possibly because her hands were cuffed behind her back.

"What's up?" Brooke called out to the newcomer.

The new girl, antsy and bouncing from side to side on her feet, said, "Dakota's been, like, edging me for forty-five minutes now, gettin' me close, then stopping, then she just let me go! She said she was punishing me!"

"Well, you have been late to practice a lot lately," Kaitlyn said.

"Yeah, but, I'm super horny and ready to burst, and I can't touch myself like this! Can't somebody help me, please?" the new girl pleaded. Her eyes were wild, and she shook with anticipation.

"IDEA!" Brooke shouted excitedly, running over to the girl and bringing her over to me. "This is the best cock in school, between him and us, we'll get you off nice and hard and lickety-flickety-split! If that's, like, okay with you two?"

The girl looked to me, and I to her. I asked Brooke, "Is she eighteen?"

"I wouldn't be here if I wasn't," the girl grumbled hungrily.

"Then I'm fine if she is," I said, rather enjoying the view of the girl's lithe body.

"I am," the girl said. "Can someone get me out of these cuffs?"

Jade looked at them. "No quick release on these love cuffs; well, isn't that nice and safe? I'd have thought Dakota would have more sense than that."

"I don't care about the keys, just, someone help me get on him?" the girl asked.

Like the oversized sex toy I sort of felt like lying on the floor, I stayed put while Brooke and Sarah led the handcuffed girl to me, helping her kneel down and straddle my cock. I reached down, helping angle my cock for better penetration, and as it pressed against the new girl's tight, wet lips, I was worried for a second that it wouldn't fit. I'd been with some tight girls before, but this might have been my limit.

Even with that, she was quite determined. Gritting her teeth with determination, and with Brooke's and Sarah's coaxing, the girl settled down slowly, the head of my cock finally breaking through and disappearing inside of her.

"Holy shit!" she exclaimed.

"I know, it's, like, totally awesome, right?" Brooke said, kissing this girl delightedly.

My cock was in heaven, and as this girl settled down more onto me, her eyes pinched shut in concentration as mine couldn't look away from the sight of my cock spreading her pussy obscenely, some of my best friends helping her through this... I thought this might well have been a pretty perfect moment.

Then she settled down entirely, the last of my cock buried deep inside of her. Her eyes now open, the girl looked at me with a truly radiant smile.

"Oh, yeah, btw guys, Ryan Collins, Alyssa Nguyen; Alyssa Nguyen, Ryan Collins," Brooke said, almost as if we were supposed to exchange a handshake instead of me being buried balls deep inside of her while she was handcuffed.

It said a lot about the year I was having when I realized right then that I hadn't gotten her name before we started, and that this was the first time I'd almost had anonymous sex.

"Hey," I said. "It's, uh... nice to meet you."

"You too," Alyssa said, looking down to where our crotches met. "Holy crap... you've got a nice cock."

"Well, you've got a nice pussy," I said.

"Thanks," Alyssa said, smiling bashfully.

"Hey, guys, say cheese!" Brooke exclaimed, taking a picture with my phone. Though our faces probably looked more baffled than sexy, I doubted this would be the only chance I'd get to take a picture with Alyssa Nguyen over New Year's.

"Alright, pictures are nice, and all, but, that doesn't, like, change my situation any, so, if you guys wanna, you know, help me get off or anything while I ride him, I wouldn't say no," Alyssa said.

Appearing at her side, Rose said in her take-charge voice, "Well, you guys heard the woman! We've an orgasmic rescue mission; who's ready to take the call?"

Impressively, the answer seemed to be: everyone.

For all the arguments and infighting and differing personalities the cheerleaders had among them, it seemed that Dakota's machinations had enough to get them all moving. Seeing ten gorgeous, naked women piling up around and behind and beside Alyssa as we fucked, watching them lend their hands, mouths and dirty words whenever their hands and mouths couldn't reach. With hands on her tits and more reaching down to play with her pussy as she fucked me (while I kept my hands on her hips to help balance her), Alyssa looked like she was in heaven. In the rare moments where she wasn't kissing one of her friends, her moans were high and full of absolute pleasure. Though I was more along for the ride on this encounter, I was happy to help and absorbing absolutely every bit of this singularly insane moment as something I wanted to never forget.

It didn't take long for Alyssa's first orgasm, powerful and screaming to tear through her body with her friends' efforts, and though her tight pussy squeezed me almost painfully, it wasn't enough to stop me from helping everyone along. Whatever she'd been building up for the last 45 minutes or so with Dakota's edging and teasing came out explosively as a gush of her juices covered my cock.

While this would have been a fine moment to start letting her come down, her friends weren't going to let her go that easily. Though there may have been a brief moment of slowing, of sympathy and kind strokes, of giggles and sweet kisses, they redoubled their efforts in no time, going at Alyssa again, starting her up and making her cum on my cock a second time.

Then a third time. Then a fourth.

They were insatiable, and only let her go when she was crying almost deliriously from the pleasure.

"Thank you, thank you, thank you everyone!" Alyssa exclaimed, before one final, conclusive cry of "Fuuuuuuuuuck!!"

Though all the attention was rightly on Alyssa with me acting as a bit of an oversized sex toy for this "orgasmic rescue mission", a couple did look down at me with some sympathy.

"You haven't cum yet, have you, Ryan Collins?" Rose asked me.

"Not bad," Cleo admitted, looking me up and down, her dark eyes still skeptical over the whole picture of who I was, but definitely intrigued.

"That's so much better than 'not bad', you don't even understand it," Alyssa said with starry eyes, looking down at me and smiling brilliantly. "Thank you, thank you, thank you Ryan for helping me! I really, really, really needed that and you were super sweet for holding on there and just letting me ride you. If you gotta go, lemme know and you can, like, cum in me, I don't mind one bit!"

Now, when you're buried balls deep in a cute, tight Asian cheerleader and she offers to let you fill her pussy, well, that's an opportunity you seriously need to consider taking. I mean, I barely knew this girl, and that definitely gave me some hesitation, but the way she looked down at me so cutely, her smile so sweet and genuine, I was pretty sure I wanted to get to know her more.

I began, "I think-"

With a jangle and a slight thud, a small key ring landed on my bare chest. The keys were almost so small as to be insubstantial, but they were no doubt the perfect size for the cuffs that bound Alyssa's hands behind her back.

"I leave the room for a little private time, and I find you've snuck a deserter and a boy into my party? If things are always going to get this interesting when I turn my back, I ought to turn my back more often," a firm voice said from the edge of the room.

I knew who it was even if I didn't already know the voice. Rose casually turning to confirm the speaker's identity, though, certainly helped.

"Hey, Dakota Lewis. What's up?" Rose said with perfect calm.

Though my view of this dreaded cheer captain was blocked by a wall of luscious, bare flesh, I could sense the girl prowling around the edge of the room.

"I see that you've earned back the hearts and minds of the other girls on the squad, Rose. Good for you," Dakota said, even though there was very little in her voice that sounded pleased with the turn of events. "Have fun, enjoy the party. I'm more interested with the boy on the floor with his pants around his ankles and, though I can't verify it from my current stance, presumably his cock stuffed up Alyssa's cunt."

Dakota walked around the edge of the wall of cheerleaders so that I could fully see her.

At once, she was exactly what I expected and nothing like I expected. Though lying on the floor made her 5'8" stature tower over me, that she was wearing her formal blue and white Regan Hills Pumas cheerleader outfit threw the intimidation factor off slightly. With blue, knee-high socks, a short blue and white-striped skirt, I knew she had long, toned legs. The top did little to flatter her breasts, and the long-sleeves and immaculate gloves were more sterile-looking than enticing, but it was her face that was truly confusing for the bogeyman image I'd been given. Her face was perfectly pleasant, ordinary even, in a pretty sort of way. Her dark brown hair hung just past her shoulders, while her soft blue eyes sparkled with something I couldn't adequately pinpoint. With high cheekbones dotted with freckles, a faint tan and a broad smile, she looked, well, like a cheerleader, not the monster from the depths the other girls made her out to be.

With arms crossed across her chest, Dakota drummed her fingers on her elbows as if considering her next move. She looked down at me curiously, as so many girls who'd heard about me without ever knowing me seemed to. It was that look I'd gotten to understand so well of, 'You're the guy?'

"Ryan Collins?" she said.

"Yeah," I replied.

Her smile twitched up a little more, only slightly. "Dakota Lewis. I've heard a lot about you. Let's talk. My room, main house, three minutes."

As quickly as she'd entered the room, Dakota disappeared. I looked around to the others nervously, settling my eyes on Kaitlyn. With a simple, short nod from her, I knew it was time.

It was time I finally got to know Dakota Lewis.

***

When preparing for conflict, it helps to go comfortable, and to that end I washed myself up a little in the bathroom and pulled my pants (if not my shirt) back on before making my way over to the main house. All the while, the girls around me gave me tips and warnings, making it all the more overwhelming. This didn't help my comfort.

Nor did my erection. After playing around with Rose in the car, then fucking both Brooke and Alyssa without cumming once, I was rock hard, and my balls felt like they were about to explode at any moment. Whatever reckoning I was due to have with Dakota, I hoped that it would involve some release.

After some stumbling around her house trying to find where exactly her room was, I made it with perhaps ten seconds to spare. The door was closed, but left open a crack, just enough to offer privacy while still being welcoming.

Taking a deep breath, I opened the door and stepped inside.

"Would you kindly close the door behind you? All the way?" Dakota asked from the depths of her room. She sat in a chair at her desk, looking away from me.

Without hesitation, I did as I was told. Smirking, I joked to myself in a low voice, "You know, there are better ways to control my actions..."

"Seeing as how my name isn't Atlas and this isn't Rapture (though this room has seen its share of that latter word), I've no doubt you're absolutely correct on that matter," Dakota said.

If she wanted to surprise me, well, mission accomplished. It was this that made me take in her room, which seemed more ornate an ornate library with a bed in the middle than the traditional cheerleader's bedroom I'd become accustomed to. Bookcases full to bursting with titles on almost every topic imaginable covered nearly every wall, save for the space dedicated to her trophy case and the few bare patches of wall she'd deigned acceptable for pictures of her accomplishing her many achievements.

Dakota spun her chair around to assess me. "Now, tell me... do you see yourself as the hero of this tale?"

"What tale?" I asked.

"The one you call your life. The one which all our lives have intersected with in one way or another today," Dakota responded.

This was taking an interesting turn. It wasn't one I was fully prepared for, but it was one I thought I could handle. "Usually. Not always. Sometimes... sometimes I've made mistakes. Sometimes I've done unheroic things. Things I'm not proud of. So, maybe I'm more my own protagonist, most of the time, rather than a hero, but aren't we all the protagonist of our own story."

"Those who are aware of their own self-destructiveness might disagree, but I see your point. So, you don't come to me today a hero?" Dakota asked.

"No," I replied.

She smiled. It was not a friendly smile. "You say you don't come the hero, yet why do I expect you're here like all the rest?"

"All the rest? Of what?" I asked.