Senior Year Memories Ch. 24

"Maybe," I agreed, squeezing her ass with both hands.

"For what I gotta say, I need to keep a clear head, so maybe don't touch my pussy for a little while. Eat my ass, though, and, well..." she trailed off.

"Way ahead of you," I said, crawling up onto the bed and sliding between her legs. I parted her marvelous ass cheeks with my hands, getting a good look at her tight, puckered little asshole, and unhesitatingly dove in, licking and sucking her forbidden entrance.

"Mmmm, that's really good," Kaitlyn purred, looking back at me appreciatively.

Taking my lips from her hole, I said, "You wanted to talk?"

"Right," Kaitlyn said, "Get eating, I'll talk."

"Roger that," I said, diving back in.

"I know you and Rose are planning on crashing Dakota's New Year's party, and a few of the girls and I thought that someone should prepare you for what you're getting into. So, I'm here, preparing you while I get a really nice rimjob. I'm having a good day today, honestly," Kaitlyn said.

Right. That. I'd been told about some of the wild parties the cheerleaders had for some time now, with most of them sounding like truly impressive all girl orgies. I would be a definite outsider in the midst, but with the number of friends I'd made on the cheer squad, it didn't sound like that big a deal to me.

I replied, "What do I need preparing for? I know you guys, I know about Mouth Parties, I know-"

Reaching back, Kaitlyn shoved my face back into her delectable ass, and I was all too happy to continue pleasuring her.

"You know some, but you really don't know how things work when it comes to high and mighty cheer captain Dakota Lewis. You've heard about the New Year's Party, but you didn't know that it was gonna start on the 30th, did you?" Kaitlyn asked.

She was right, I didn't know that.

She continued, "Dakota's parents are out of town for New Year's, and since she loves overdoing things almost as much as she loves being a heinous bitch goddess, she's starting on the night before New Year's Eve. All of us who're coming, we get there then and we're gonna have us a sleepover on the 30th, and then pretty much party all day the 31st. You've never really been to a party before, have you?"

I thought about it. Homecoming was the closest I'd ever come, and that wasn't really a party (even though what happened afterward felt pretty close). It'd be a marathon, but with a bunch of naked cheerleaders on hand, that was a sacrifice I'd have to make.

"I'll manage," I said.

"You'll have to, because shit gets intense there. I don't know who in all is coming for sure, but Brooke, Jade, Haley, Addison and Rose I know for sure, including you. I'm really trying to talk Sarah into coming, part of her initiation, ya know? She's waffling, but if you could help any, that'd be great; she's a real hot little slut, I'd hate for her to miss out on something like this," Kaitlyn said.

"I'll talk to her. She's shy, but she wouldn't want to miss something like this. She's a real freak in the sheets as you know," I said.

Groaning almost nostalgically, no doubt thinking of the threesome she, Sarah and me had had earlier in the month, Kaitlyn said, "Oh, I know. Keep doing that thing with your tongue, feels fucking good."

I had no intention of stopping doing that thing with my tongue, especially with the way Kaitlyn's body was tensing. I could feel her body tightening, smell and feel the moisture coming from her cunt. I knew that she had a lot to say, and I was glad to hear it, this being my first party and all, but I was hoping I'd get to fuck her again real soon.

"It's the girls you don't know that're gonna be there, they're the ones you gotta worry about, 'cause they can take you off guard if you don't know what you're getting into," Kaitlyn said.

"I gotta worry?" I asked.

"What'd I tell you about keeping on with your tongue?" Kaitlyn asked.

"Sorry," I said, continuing as I was told. Kaitlyn wasn't nearly so bitchy as she used to be, but the moments when it came out during sex were, admittedly, fun sometimes.

"Mmmm, right there, yesyesyes," Kaitlyn hissed, smiling back at me prettily. "Now I'm not saying you need to worry about all of them. Sasha Pearl... she's a sweetheart. Kinda tall, skinny redhead, you got a thing for redheads, right? She's got big glasses and is kinda the nerd in our group, but don't underestimate her: get her horny and she'll destroy your fucking cock."

I didn't have a particular thing for redheads (even if I had fucked Haley and three women in the McNeil family), but that wasn't to say that what Kaitlyn said wasn't enticing.

"After her, though, yeah, you got some serious bitches to worry about. Like Gwen Savage. You know her, right? Trashy blonde, always wears too much makeup, would take a minor miracle to pull off her headphones out of class or cheer, has tits almost as big as mine? She may look like just another dumb blonde, but don't mistake her, she may be a little dumb, but she's tight. And greedy. Start fucking her and she'll hold onto you and never let you go until either she's worn you out or you've worn her down. Now, I know you're good, but that bitch can take even you out," Kaitlyn said.

Now that was a warning. One I was still looking forward to confronting, but definitely something I was ready to find out about in more detail.

"And then there's Cleo and... you know what, wait a second, this is bull, I need some cock and I need it now. Get naked and lie down, I'm gonna fucking ride you," Kaitlyn said, pushing me away. She sat up in the bed, pulling her shirt off and revealing her beautiful, bare tits to me, while I tried to set a speed record for getting naked and lying down.

Since I was already rock hard and Kaitlyn was ready and waiting, it didn't take long before she crawled on top of me and settled the entire length of my cock deep in her slick cunt.

"Oh god, I'll never get bored of this," she hissed, looking down at me with a look of contented superiority.

"The view's pretty good from this end too," I said, reaching up and squeezing her nipples gently. Smiling sweetly, she leaned over and kissed me hard. If she had a problem with me having spent a good long while making out with her ass not but a minute before, you wouldn't have been able to tell for how vigorously we made out. We stayed like that for a while, but soon she sat up on me, grabbing my hands and placing them on her ass as she began to ride me.

"Oh yeah, fuck, god you're so fucking big, so hard, I love it, I love it, I love it!" Kaitlyn yelled. I didn't know how much the girl across the way could have heard from her room, but if she was listening, Kaitlyn would have been hard to ignore. "Fuck yeah, fuck yeah, fuck yeah! Now... fuck... where was I?"

Wracking my brain for an answer that seemed to disappear the harder she rode my cock, I answered, "Cleo?"

Kaitlyn perked up, never once breaking pace as she fucked me. "Right! Cleo Price! You've had her in class, right?"

Not that I ever had talked to her, but I had seen her. Cleo Price was hard to miss. A dark-skinned black girl with her hair usually done in a set of long microbraids, at just a shade over six feet tall of nearly pure muscle with F-cup tits and wide hips, she was as imposing as she was beautiful.

"I've seen her around," I grunted.

"Well, she's one of our bases, the strong girls who lift our tops or toss our flyers, the tinier girls like Brooke and Riley and Kitty (those two aren't coming, so sad, you'd have had fun with them), and when she gets naked and started, god help you if you try to stop her. The girl's a machine and she'll fuck you so hard you won't be able to walk right for a week afterward," Kaitlyn said.

I nodded. "Death by snu-snu, got it."

"What's 'death by snu-snu' mean?" Kaitlyn asked.

I blinked up at her. Sometimes I still had to remind myself that there were still many things about Kaitlyn and me that were still very, very different. I said, "It's a classical reference."

"Ah," Kaitlyn said, as if that explained everything. "Well, even if you're prepared for 'death by snu-snu', you still won't be ready for Dakota motherfuckin' Lewis."

Now, I'd been hearing about the horrors of cheer captain Dakota Lewis for a few months now without ever having had the opportunity to meet her myself. Our classes never lined up in such a way, and given the different social circles we traveled in she was pretty much a complete mystery to me. I knew a lot of the girls on the cheer squad liked to talk shit about her, that she was a serious control freak, and that she threw the occasional cheerleader orgy that nobody had anything bad to say about. That gave her, well, an interesting legacy as far as I could tell.

I mean, if she let Sarah onto the team, she couldn't be that bad, right?

Slamming her hips down onto mine with impressive ferocity, Kaitlyn continued, "No matter what you do, no matter how hard you try, Dakota will always find herself on top just where she likes it. She likes to dominate and fuck people over if it means getting what she wants, and if she wants to cum, you better deliver or prepare to face the consequences. You think I used to be a raging cunt? You ain't seen nothing until you've seen Dakota motherfuckin' Lewis."

Given the way she was bouncing on my cock, I was inclined to believe pretty much anything Kaitlyn had to tell me at this point. When she slowed, though, rocking her hips to only take a few inches of me at a time, looking down at me with that beautifully smug look only she knew how to pull off so well, I was driven close to madness.

"There's one advantage you've got, though, that might help you tame the bitch," Kaitlyn said.

"What's that?" I groaned, wanting desperately to start fucking again.

She leaned over, crushing her breasts against my chest as she whispered in my ear, "I don't think she's ever fucked a cock as big as yours. I've told her about you before, and believe me when I say she's interested. Whip out this monster, and I think she'll be putty in your hands. You'll tame the bitch, and we'll have us a happy fucking new year."

As if emphasizing her point, she squeezed my cock oh so daintily with her pussy, no longer moving, but just prodding, urging me on to do what she wanted. Kaitlyn liked to toy with me and her friends, and though I'd become accustomed to it in her unique trickster way, when it put me in this state of sexual frustration, a dam was guaranteed to burst soon.

I was past the point of no return at this point, desperately needing to cum. Growling, I wrapped my arms around Kaitlyn and rolled over so I was on top of her. She squealed with glee, wrapping her legs around me as I pounded into her like my life depended on it.

"Fucking nice, fucking nice, like that, yes, yes, yes!" she squealed.

"Want me to do your dirty work?" I grunted. "Want me to tame her like I tamed you?"

"Nothing tames me, I just, got... some... new... perspective!" Kaitlyn yelped as I slammed into her.

"Then I'm gonna give her some new perspective too. If she wants this cock, I'm gonna give it to her, and I'll make her scream so fucking loud the whole town will hear!" I roared as I mercilessly fucked Kaitlyn.

"I wanna see! I wanna hear! I wanna know you, oh fuck, I wanna know you got her to chill the fuck out with that giant fucking cock!" Kaitlyn yelled.

"It'll happen, but first, I'm gonna make you cum!" I said, fucking her more determinedly.

"Only as hard as I'm gonna make you cum!" she taunted back, squeezing me and rocking her hips in time with me as I kept giving her everything I had.

For a moment, we looked into each others' eyes in complete understanding, an understanding that we sealed with a deep, passionate kiss, a kiss only broken when Kaitlyn shuddered against me and cried out.

"FUCKING HELL, YES, YES, YES, I'M FUCKING CUUUUUUMMING ON YOUR BIG FUCKING COCK!!"

Her pussy squeezed me so tightly, pushing my already extreme pleasure over the edge as I came inside her. Wave after wave of sweet, draining pleasure hit me as I pumped my cum deep inside her pussy, feeling like I was draining my entire body into her.

Panting heavily as we both came down, I kissed her one more time before rolling off and laying down beside her.

Breathing heavily, Kaitlyn looked at me dreamily and said, "You know, I think we're pretty good at this."

Trying not to think about how loud we were, and if we were being overheard next door, I said, "I think you're right."

"So, ready for the party tomorrow?" Kaitlyn said.

I laughed. "Maybe if you don't drain everything out of me first; something tells me I'm gonna need to train for this one."

Teasingly, she poked me in the side, "You'll do fine. Though I wouldn't mind an ass-fucking before I went on my way."

She knew just how to keep me interested. I looked down at my twitching cock. "Give me a few minutes, and then you're on. I've still got that box of sex toys you guys gave me for Christmas; there's some good stuff in there. It's under my bed if you want to play around while I get hard again."

"Awww," she said, kissing me hard. "You know just how to treat a lady right."

Getting up on her hands and knees and turning around to look under my bed, giving me a perfect view of her stretched out pussy lips dripping both of our cum down her thighs, I muttered to myself, "Now to see if I can treat a whole lot of ladies right."

***

In spite of its name, Regan Hills wasn't quite as hilly as its name might imply. What few hills it did have, however, tended to be where the richer end of the populace lived. As a kid who grew up smack dab in the middle of middle class suburbia, this wasn't exactly a part of town I frequented or even wanted to frequent, but the occasional exception had to be made.

Attending a nearly two-day long cheerleader orgy, for instance.

It was early evening on December 30th, and I sat in the passenger seat of Rose Ferris' car, looking on in some awe at the large house-but-not-quite-mansion that Dakota Lewis called home.

"You will never find a more wretched hive of scum and villainy," I muttered, thinking I was only loud enough to hear it myself.

"We must be cautious," Rose said in her painfully sexy, husky voice, finishing my quote.

I looked back at her, and as ever when in her presence I found myself sublimely impressed that I had someone so effortlessly cool in my life. "God, you're awesome."

Pushing her sunglasses up her nose, Rose replied, "This isn't news to me, Ryan Collins."

Rose was, as ever, a sight to behold. Dressed in her usual mishmash of hipster clothes, including distressed jeans that were barely pants anymore and a fedora, she was undeniably gorgeous. Soft, full lips curled into an intelligent smile that lit up her already gorgeous face, framed beautifully by her wavy, platinum blonde hair highlighted with blue streaks. Though she hadn't been a cheerleader for some time, she kept her body tight, with firm, C-cup tits and a nice, round ass. I'd have loved to hang out with her if just for how hot she was (and how intense a fuck she was), but it was her personality that easily made her one of my favorite people to be around. Always bright, always aware, always unhurried and unworried, she just had a natural cool to her the likes of which I'd always wanted but was never able to cultivate.

"How are you so relaxed right now?" I asked her.

She shrugged. "Well, firstly because this den of vipers is one I'm intimately familiar with."

"A lot of whom you haven't seen in a while and still might hate your guts," I said.

Rose mulled this over. Her quitting the cheer squad to follow her art was still a sore point among many of the cheerleaders as far as I knew, but she'd made inroads with a number of them during my Christmas Good Deeds spree.

Finally, she said, "Perhaps they might, but with allies such as mine, the distraction you'll no doubt cause, and everything my most capable tongue and fingers are skilled in... I believe most will forgive sooner rather than later, wouldn't you agree?"

I couldn't speak for the others, but from personal experience I knew that Rose Ferris could get me to do pretty much anything she wanted me to do if she only asked.

"And what's the second thing?" I asked.

"Pardon?" Rose replied.

"When I asked you about why you weren't nervous, you said 'firstly', which generally seems to indicate there'll be a 'secondly' and possibly more afterward," I said, wanting to keep this going for a moment or two more to steady my nerves.

Rose laughed, clearly knowing what I was doing. "It would typically indicate such a thing, wouldn't it, Ryan Collins?"

"So, is there a secondly?" I asked.

"Of course."

"Because you've got me on pins and needles."

"Patience is a virtue, you know," Rose chided.

"And I think you're being a tease," I replied.

"Fine, fine, you win. If you wish to know my 'secondly', it's simply this: this is hardly my first orgy."

Though I'd hoped for a more profound answer, I nodded as this made sense. "Kaitlyn already gave me her warnings about the people inside..."

"Good of her to do that," Rose agreed.

"...but... well, can you tell I've never done this before?" I said.

"And you need some orgy etiquette advice?" Rose asked.

Exhaling and grateful that she was able to get the answer right away, I replied, "Yes, please."

Putting her hand on my thigh pleasantly, she said, "There's not much to it, really. Don't force yourself into a spot where you're not wanted, but if you are wanted and just don't feel it, feel free to say no. Don't tire yourself out right away, since this is a marathon, not a sprint, and don't be afraid to take chances. You may not always hear 'yes', but if you don't ask, you'll never know whether you could've had the fun you wanted or not. And hydrate. Can't stress that one enough. Hydrate like crazy, and use the bathroom when you need to."

That... that all sounded practical. It didn't eliminate the butterflies in my stomach, but it did set them at ease.

Well, most of them, anyway.

"This would be the point where I'd recommend considering an orgasm to take the edge off," Rose said. "But, given your anatomy, I imagine you'd be better off holding off on an orgasm until you're ready for the big show, Ryan Collins. You'll want your cum, almost as much as the most delightful sluts inside will."

I was hard as a rock, and would have really enjoyed a good blowjob from Rose to take the edge off before going inside, but her point made sense.

"Still, should you be in need of something to help you focus before we call up fair Brooke, I can think of an idea or two..." Rose said, unbuttoning her jeans and showing me her pale blue panties. Her eyes sparkled over the edge of her sunglasses, and as if she didn't give me enough of an indication of what she wanted already, she bit her ever so luscious full lower lip.

When I first met Rose, I found out she had a thing for being fingered in public (or close to public), and though it never ceased making me a little nervous, I knew it thrilled her to no end. Thinking that a nice fingerbang might be as good an appetizer as any for this evening, I looked over each shoulder, checking and double-checking that we were alone. Satisfied that this empty street (or empty enough street, if you didn't count all the other cars parked in front of this house) was clear, I leaned over and kissed Rose.

She kissed me back, smiling against my lips, completely unhurried as she reached over and playfully stroked my erection through my jeans.

"You're bad," I groaned, reaching over to cup one of her breasts through her shirt, before dropping my hand between her thighs.

"I am many things, Ryan Collins," she teased. "And bad is a fairly subjective term. If you wish to call me names, might I request a little more precision?"