Senior Year Memories Ch. 26

I thought about it. "Just promise me... promise me that if this happens, that no matter what we'll be friends. I like all the sex I'm having, but I like the friendships more, and I wouldn't want to lose you."

She smiled at me sweetly, her voice barely a whisper when she said, "Thank you."

"Promise me?"

"Of course. I promise," Sarah replied.

I kissed her. "Then I'll think about it."

"Good," she said, rolling back onto her back and looking at the ceiling with me.

"I wouldn't mind that shower, though," I said.

"Yeah, ditto, I'm all kinds of sticky," she replied.

I grinned at her playfully. "That assfucking still on the table?"

"Let's get cleaned up first, but then... yeah, probably," Sarah giggled.

Putting my hands behind my head and smiling, I said, "Fuck this has been a weird, awesome party."

***

"Okay, girls, we can get the coordination of this working, this really isn't that hard, is it?" Dakota asked, hands on her hips and tapping her foot on the ground expectantly. The naked brunette with the slender frame, C-cup tits and bushy pubic hair looked commanding and intimidating, yet utterly gorgeous at the same time.

"Easy for you to say; you're just taking it, we're the ones doing all the work," Haley replied, arms crossed under her amazingly huge H-cup tits. The curvy and pale redhead was one of the few girls I knew bitchy enough to match up to Dakota's reputation, but even in her sass she seemed a little intimidated by her cheer captain. You'd have thought given the size of the strap-on she wore that she'd be the one in charge, but Dakota had a way about commanding a room when she was on.

And let me tell you, this time she was on.

"Well, I need to see what you've got, and so far what I'm seeing doesn't impress me one bit," Dakota said.

"Oh, relax, Dakota, we'll make it work. We always make it worse in the end," beautiful and busty dark-haired Kaitlyn said. Easily one of the most gorgeous women I knew (and fuck that was a competitive list), with her DD-cup tits and sweat-glowing body, she looked several different levels of hot, even with the large strap-on she was wearing.

"Don't you mean in my end?" Dakota quipped.

"My end too," Kaitlyn shot back, glancing at Haley.

Haley looked at me, licking her lips. "I'm ready. You ready?"

Even with my cock overtaxed by all the insane sex I'd been having lately, I was not going to turn down an opportunity this hot. "I'm always ready."

"Good," Dakota said, getting down on all fours. "Because this is a rare opportunity for you girls, and you better take it while I'm offering it."

Leaning her head on the floor, she reached back and spread her ass cheeks to show off her perfect, tight little hole. "One of you better shove a dildo up my ass while I'm offering, because this is a limited-time only sort of thing."

"Dibs!" Kaitlyn shouted, dropping to her knees behind Dakota before Haley even had a chance to realize what was happening.

"So not fair," Haley pouted. I'd heard a lot of girls claiming that things weren't fair these past couple days, and by experience I'd learned that those protests could usually be turned around with the right way of looking at things.

"Ahhh, fuck me..." Dakota hissed as Kaitlyn pressed the head of her lubed-up strap-on dildo into Dakota's ass. Since Dakota's ass was incredibly tight (something I knew from glorious experience) and the dildo was very, very thick, it made for a really nice watch.

"Take it, bitch," Kaitlyn playfully hissed. "You know that's how you've always wanted it, now take it like the bitch you are."

"Pissed that's not you?" I whispered to Haley.

"Beyond," Haley replied.

Carefully, I cupped her ass. "Well, it may not be like fucking Dakota's ass, but you'll at least get to fuck Kaitlyn's ass and really give it to her good."

"True," Haley said begrudgingly.

"And..." I said, sliding my hand between her amazing ass cheeks and pressing my middle finger against her tight hole, taunting, not enough to go inside, but enough to make her shiver. "...while the other two only have toys in them, you get ten inches of serious fucking cock inside of you, so in the end, wouldn't you say you're really the winner in this pile?"

"I got it!" Kaitlyn cheered as she bottomed out the strap-on inside of Dakota's ass.

"Lucky first try," Dakota whimpered, looking back in pained pleasure.

"You might be right," Haley said.

I pulled her in close, planting a long, deep kiss on her lips. When we broke, she looked at me dreamily.

"Okay, you're right," Haley said.

"I thought so," I replied.

"Okay, bend over, bitch, your ass is mine," Haley said, kneeling behind Kaitlyn and pushing her down against Dakota's back. With little gentleness, she pressed her large, lubed dildo against Kaitlyn's ass and slid it right inside. Though Kaitlyn was one of the most accomplished girls I knew at taking it up the ass, her eyes still went wide at the sudden invasion.

"FUCK, HALEY! A little romance, next time?" Kaitlyn insisted.

"Oh, whine, whine, whine," Haley mocked, leaning over and kissing her friend. "You and I both know this is how you love it. And besides, I called dibs earlier on Dakota's ass."

"Are we really having this conversation about dibs rules now?" Kaitlyn asked.

"If I weren't pinned to the floor, I'd be happy to help judge!" Dakota said.

"Well, you are, so fuck off," Haley said.

"I'm so over these one-time-only offers," Dakota grumbled.

Looking up at me expectantly, Haley said, "So... ready?"

Now I was licking my lips. "Definitely."

I knelt down behind her, rubbing lube onto my cock as I hungrily eyed the sandwich of gorgeous, naked cheerleaders in front of me. As always in moments like this, I took a second to thank the charmed kind of life that had led me here, but rather than linger on the unlikelihood of it all, I was focusing more on Haley's ass.

I slid my cock between her ass cheeks, taunting her, teasing her a little, enjoying my position of power and how I got to play it.

"Stop teasing, please?" Haley asked.

"Yeah, we're at an orgy, not a rom-com," Kaitlyn said.

"And I'm not gonna be on the bottom forever!" Dakota said.

I rolled my eyes. "Fine, fine," I said, pressing in against Haley's tight hole. She winced pleasurably as I worked my way inside, gasping when the head popped in and groaning out loud as I fed my huge cock into her ass. As always, sliding inside of her tightest hole was heaven, so tight and hot and eager, and feeling my balls brush against her pussy was enough to make me groan.

"So, everybody bottomed out?" Dakota asked, to all of our confirmation. "Alright, then start a rhythm. Everybody work together and finger the girl in front of you; I know it'll be hard, I know it'll be weird, but if we pull it off, it'll probably be fucking amazing, or at least something to boast about. Everybody ready?"

When we all answered her positively, Dakota said, "Then let's get down to business, bitches!"

Though establishing a rhythm where all three of us could effectively fuck the ass of the girl in front of us while fingering them, we were motivated to make it working. Soon, we were all a groaning, moaning mess, dancing a strange dance that we were the only ones privy to all the moves of while other girls around us fucked and cried out and watched us curiously.

If this was business we were getting down to, it was a kind of business I could get to liking.

***

I loved a good 69. This shouldn't be new to anyone who's read this far. I love the give and take of it, I love the taste of a good pussy, and I love a good blowjob. Put all those together and you've got one of the world's most perfect sex acts in my humble opinion.

Of course, there are many perfect sex acts, so if I were forced to rank them I'd probably look like a lunatic, so since I'd rather not do that I think I'd rather describe how much fun I had 69ing Rose Ferris in the midst of the New Year's Eve party.

After a lot of hot and heavy encounters, a laid-back encounter was just what the doctor ordered, and laid back was Rose's usual running speed. A tight bodied hipster with wavy, platinum blonde hair streaked with blue, a firm pair of C-cup tits, and some of the nicest lips I'd ever encountered (both up top and down below), I always knew I could relax when Rose was around. With a little help on the inside, we'd crashed this party together, though I realized too late that I hadn't spent nearly as much time with her as I'd wanted to.

I meant to change that.

Eating her delicious, shaved pussy while she deepthroated my cock seemed a good way to get started there. She tasted good, she felt good, and as long as we were taking our time on each other, we could both catch our breaths and let time in the party pass by. When I came looking for her after my anal orgy with Kaitlyn, Haley and Dakota, I didn't tell her what I was looking for, but she knew right away.

Rose Ferris always had a way of knowing.

When so many girls would've been all set for wearing me out, she was content to take her time, and oh did I mean to take my time with her.

Already she'd cum on my face twice. I thought she'd try to return the favor, but she played with my cock unhurriedly, suckling, licking and kissing it as if it were a delicious treat, occasionally dipping down to take my entire length down her throat before going back to her toying. Even in this relaxed a state it was rather frustrating, but only in the best way.

When she got me close again, close but not quite there, I decided to push things a little further. I slid two fingers inside of her pussy and another in her ass, thrusting them, curling them, pushing her to the edge and then well over it as she pulled her mouth off my cock and cried out in orgasm yet again. Her sweaty, shaky body sliding against mine was one of the most perfect feelings in the world, and I couldn't help but take great pride in what I could do for her.

"Okay, Ryan Collins," she said, panting for breath. Rose climbed off of me, only enough to turn around and then re-straddle my hips, taking my cock into her perfectly tight, hot and wet slit. "I'd say that's enough teasing."

"I'd have said that a while ago," I said, groaning with pleasure. "But this is a good way of making it up to me."

Slowly, she began to rise up and down on my cock, keeping her pace slow and distinct. "I thought you might agree."

Rose bit her lip, riding me deliberately and looking so completely beautiful as she did. I was unused to seeing her without her fedora and sunglasses, but at some point in the past few hours she'd completely just given up on them. Getting a rare opportunity to look her in the eyes, to see that complete and effortless confidence that made me like her when we first met.

I pulled her down toward me, enough that I could suckle on one of her perfect nipples. I flicked the hardened nub with my tongue, nibbling on it just slightly enough to make her moan.

It did the trick.

Rose smiled down at me, rocking her hips harder as she bounced on my cock. Not too much, not too fast, she didn't want to speed up what we'd started, but it was enough to tell me she was having fun.

In that spirit, I wrapped my arms around her and rolled on top. She looked up at me, no doubt fully expecting that this was when I was just going to go to town on her. Then I smiled, keeping the slow, deliberate pace. It wouldn't be enough to get me to cum right away, but I was in no hurry.

"Ah, you know how to treat a girl right," Rose said, grinning with satisfaction.

"Josie seems to think so," I replied.

"And what exactly are her thoughts on your orgy activities?" Rose replied, wrapping her legs around me and urging me forward a little more.

"She thinks they're hot. I think that's why she's trying to outdo me. She set up a gangbang with a bunch of people she met in Hawaii last night, looked like she had a great time," I said.

"And you don't have a problem with that?" she asked.

"Why would I?" I asked, thrusting into Rose for emphasis. "I'd have to be a major hypocrite if I had a problem with Josie having sex with whoever she wants when I'm... you know..."

"I know," Rose said, squeezing my cock with her pussy.

"We have each others' hearts. That's what matters, in the end. Who we fuck around with when we aren't together... well, that's just fun, isn't it?" I proposed.

"That it is," Rose purred, urging me on a little harder. "So, do you think she's going to beat you?"

I laughed. "I've my doubts, but I've also learned better than to underestimate her."

"A wise strategy," Rose laughed back, turning her head to the side. "Oh, look, we've an audience."

"I don't care about an audience," I said, only looking down at Rose, only wanting Rose here and now.

"Not even a greatly jealous-looking Gwen Savage without a partner in the world seriously trying to not watch us and touch herself?" Rose mused.

Admittedly, this probably would've been a great sight. Gwen Savage was a trashy blonde and one of the least pleasant cheerleaders here. Like all the others, she was unusually hot, but her pushy attitude toward my friends made me resistant toward her advances. I was interested in having sex with her before all this was over, but until then I was more than happy to make her work for it.

"Tempting," I said, quickening my pace slightly. I was ready to burst, and that necessitated a little more movement, something that Rose was all the happier to encourage with her legs wrapped around me. "But I'd rather keep making her jealous by cumming inside of you.

"Oh, Ryan Collins," Rose purred, "You really know how to make a girl feel SPECIAL!"

She yelped as I came, covering my groan as I pumped her tight cunt full of cum. It was an exquisite kind of pleasure, one I would never want to end as I kept pushing into her, filling her with everything I had. When it slowed, with me out of breath on top of Rose, I kissed her tenderly. It was an act she was happy to return.

Smiling slyly, I asked her, "Is Gwen still watching?"

"Uh huh, though it looks like she's on the hunt for a vibrator," Rose replied.

With some thought, I said, "Good."

Though not the funniest joke in the world, it was enough to make us both share a private laugh.

***

When you're at an orgy, sometimes it's best to join in, and sometimes it's just best to watch and see what was going on. Come across a sight as perfect as Cleo Price and Sasha Pearl locked in a passionate embrace and you'll understand the benefits of just letting something beautiful happen.

On the surface, the two of them couldn't have been more different. Sasha was a willowy, pale redhead, tall and gangly and carrying a modest pair of C-cup tits, with a goofy smile, freckles and large glasses. Cleo Price, on the other hand, was a muscular and tall black girl, curvy and fit with a big ass and even bigger F-cup tits. Sasha was timid but full of sexual energy, while Cleo was aggressive to a point where she easily hid how nervous she could be around guys.

They probably wouldn't be the kinds of people who'd hang out together if they weren't on the same cheerleading squad, let alone doing this with each other, yet here they were just utterly going to town on each other. They were kissing and caressing each other, eagerly licking at each others' necks and nipples while each had a hand buried between each others' thighs, fingering the other girl like crazy. It seemed like they were in competition with each other for who could make the other cum the most, and at the moment it appeared Sasha was ahead about 4-2, not that Cleo was complaining.

While they had their own little slice of heaven on the blanket they did this on, I just sat nearby watching and slowly jacking my cock, thoroughly enjoying the show. Occasionally they'd look over at me and smile, giggling softly to each other before continuing to go at each other. They made no effort to make more of a show of it for my benefit, and I wouldn't have asked them to; their fun was their fun. They didn't ask me to leave, though, and that was enough to keep me there, watching and masturbating, trying to figure out what my next move was going to be.

"That cock looks like it could use some attention."

That, for example, was a fine next move.

"I won't say no if you're offering, Jade," I said.

Jade Alvarez stood beside me, her mouthwatering pussy with its field of jet black curls around it almost at my eye level. If I wanted to lean over and lick it, I could have, but I was rather more interested in taking in her body. A Latina with soft brown skin, a round ass and some of the softest, tastiest DDD tits I'd yet encountered, she looked down at me with that prettiest of pretty smiles and nodded.

"I'm offering," she said. Her body was slick with sweat and her hair, long and black and silky, was a mess. She had the look and the smell of a girl who'd just been fucked a lot, enough that it made my cock twitch more for her in hope and anticipation.

"Then how do you want it?" I asked.

She answered me simply by walking over to me, standing over my cock and kneeling down. I entered her easily, her pussy as warm and familiar as coming home, and I let out a contented sigh as she settled herself entirely on my ten inches.

"This is nice," she purred, kissing me sweetly. "Though if we can, you know, rotate some so we could watch those two, I'd like that."

I did as she said, rotating just enough that both of us could watch Cleo and Sasha fuck each other silly while she rode my lap. Her tits, so juicy and tempting, bounced in my face, and given an opportunity like that I couldn't help but latch my lips onto the first nipple that got close enough. Between the pussy on my cock, the nipple in my mouth, and my hands on her perfect, juicy ass, you could say I was pretty content right then.

"So how's your first orgy treating you?" Jade asked, groaning as she fucked me.

I let go of her tit. "Really, you want to ask me while I've got my mouth full?"

She laughed. "You can fill it again. I just wanted to... damn that's some nice cock... just wanted to see how you're doing."

"How do I feel like I'm doing?" I asked.

Jade's attention was on Sasha and Cleo, both of whom looked like they were on their way to some pretty earthshaking orgasms. "You feel like you're having the time of your life."

"Well..." I groaned. "I am."

"Never thought you'd see something like this a year ago, did ya?" Jade asked.

"Oh, I thought I'd see it. I just thought I'd be watching something like it on Pornhub or something," I admitted.

Jade began riding me harder as it looked like Sasha and Cleo were about to cum. "Well, I'm glad you're here, and not just because you've got the nicest cock in school, but, because I like to see it when good things happen to good people. And, whatever mistakes you've made this year aside, you're a pretty good person, Ryan."

With Jade being one of the most genuinely kind people in school, the only appropriate response I had was, "Thanks."

"You're welcome," she said, kissing me again. It was a nice, long kiss, our tongues gliding against each other tentatively at first, then more enthusiastically as we began to make out harder.

Squeezing my cock with her pussy as she bottomed out on me, Jade said, "You know... if you're looking for a kiss at midnight, I'd be more than happy to steal you for one. I know I'd have to get in line, but-"

"There's a line to kiss me?" I asked.

Jade nodded, fucking me slightly harder, "You're a well-hung guy who's good at fucking, is kind of cute and is really nice at an orgy with only girls; you bet your sweet ass there's a line. I know Dakota, Kaitlyn, Sarah, Haley, Brooke, Cleo and Rose all got designs for you, but if it's up to me, I'd like to steal you for that midnight kiss, get the new year off to a good start. What do you think?"