Senior Year Memories Ch. 21

"Good?" she asked, rocking her hips back and forth on my cock. Her pussy lips rubbed up against me and, even in my softened and oversensitive state, felt pretty good. I knew she wanted to bring some more life from me so I could fuck her properly, but even with her impressive skills it would take a moment or two.

"You know it," I said, pointing to the cum on her tit.

Giggling, she scooped it, and the trail on her chin, up in one finger and sucked it down luxuriously. "Better than the high school slut I tasted on your cock?"

"How'd you know she was a high school slut?" I asked, curious.

"I didn't, 'til you confirmed it," Mrs. Lynn said, arching an amused eyebrow.

"Oh," I replied.

"So, better or worse?" Mrs. Lynn taunted, wiggling her ass from side to side and making those luscious tits of hers jiggle ever so wonderfully.

Since I never liked to compare the girls I'd been with when I was with another (except maybe for the occasional pillow talk fun with Josie), I played it diplomatically. "You know, when you're doing that on top of me like that, I don't think it's a fair contest, exactly."

Mrs. Lynn laughed, then leaned down on top of me. Her breasts pillowed against my chest, she spoke in my ear in a husky voice, "What can I say? I enjoy winning."

She could have pressed the matter and maybe even gotten me to break, but instead she leaned in for a kiss. Though I could still taste my own cum faintly on her lips, I didn't mind one bit. Making out with Mrs. Lynn, her naked body pressed against mine, our hands roaming over each other, it was one of the greatest pleasures in life and I wasn't going to argue about any element of it.

After all, it made staying after school all the more worthwhile.

I'd come to Mrs. Lynn's classroom after school, unannounced, to bring her my Christmas good deed, namely the offer to take on and help tutor a couple more students. Though tutoring Kaitlyn had so far involved more hot sex than tutoring, her grades in Mrs. Lynn's history class had improved sharply, and since I knew students excelling made Mrs. Lynn look better to the administration, I wanted to do whatever it took to help her out. It would stretch my admittedly limited free time even thinner, but it would be worth it to make her happy.

This was supposed to be one of the easier, less strenuous tasks on my Christmas list, the one that would allow me to put most of my mental focus toward figuring out just how I'd deal with the mess of people I had to arrange the next day (and think over all of the ways it'd likely explode). I was supposed to go in and get out, no more than a few minutes, tops.

One look at Mrs. Lynn, though, told me that that was out of the question.

As was often the case when I entered her room after school, the shutters were soon drawn and the door locked, and our clothes flying off as she took control. I made my pitch, and she accepted with wild enthusiasm and, well, once we got on top of her desk I think you know how the rest of it turned out.

"You don't think I'm being a bitch, do you? You know I actually like almost everyone here... it's just sometimes, I need to fucking vent," Mrs. Lynn said, taking a break in our makeout session without ceasing her gyrations against my hips. Her efforts were doing pretty well, as I was already beginning to reharden.

"If you are, I think you're doing it just to have some fun because you lead a stressful fucking life and you need to cut loose somehow. Between a bunch of students who drive you crazy, a husband who neglects you and kids of your own? I think you're entitled to be a bitch every so often," I said.

Mrs. Lynn smiled, kissing me nice and deep. "You may be a dirty boy, but you're also very sweet. Thank you, as always, for the perspective."

"Any time," I said, kissing her back.

Smiling, she got off of me, sliding off the desk and pulling me to the edge. Taking my juice-slickened cock between her tits, she pressed them together and gave me a slow, sweet tittyfuck that would have me hard again in no time.

"Still, it doesn't solve your problem," Mrs. Lynn said.

"What problem is that?" I asked.

"High school girls. Don't get me wrong, they're nice and fun and have some really tight bodies, but if you only fuck them, your experience can only go so high. Spend some more time with older women, however, and you'll learn so, so very much more," Mrs. Lynn said.

"I have a lot of fun with you, and I think I've learned a lot from you," I said, without acknowledging that I'd had some more fun with both Tori's mom, Lauren McNeil, and our school's librarian, Mrs. Sullivan, both older women whom I'd had an amazing amount of fun with.

Looking down at my now completely hard cock, Mrs. Lynn kissed it and got up. "Come on, bring the lube and bend me over Chloe Marcus' desk."

There were few things in life I wouldn't have done after hearing the phrase "bring the lube", so I was up in a flash. I retrieved the small bottle of emergency lube I kept in my backpack.

As was often the case when we got together, Mrs. Lynn, wearing nothing but her high heels and one of the sexiest damn smiles on Earth, was slightly bent over Chloe Marcus' desk, her luscious ass sticking out at me invitingly. Though Mrs. Lynn had a habit of trash-talking a lot of the problem students in school when she was stressed, it always amused me to no end that she reserved the greatest wrath for blonde know-it-all Chloe Marcus, who was more annoying than anything else. We'd fucked over Chloe's desk enough times that I was impressed nobody was ever able to tell what happened against it.

Still, if she wanted me to fuck her ass over Chloe Marcus' desk again, I wasn't going to complain.

I stood just behind her. She smiled down appreciatively at my cock and said, "Lube up. I want you in my ass soon, and I want you to make me fucking scream like a banshee, understand?"

"Always," I said, squeezing lube onto my hand and rubbing it into my cock.

"Good," Mrs. Lynn said. She continued, "Back to what we were talking about, I've enjoyed our time together immensely, but I don't want you thinking that I'm the only game in town when it comes to top shelf MILF. There are a lot of other women in this town, in this school even, who should enjoy your talents too..."

I slid my slicked up cock between her ass cheeks, teasingly pressing it up against her tight, puckered hole. Cooing softly, she squeezed me with her ass cheeks, urging me onward. I pressed forward, pushing my cock into her tight, puckered hole. The moment I broke through, burying several inches inside of her, I think both of our moans nearly drowned each other out.

"Oh I'll never tire of how good this feels," she moaned.

"Amen," I said, reaching behind her and cupping her tits, feeding several more inches of cock into her tight ass.

"...just so you know, I've got some friends who could use the help of a guy like you. Someone sweet and considerate and hung like a horse and who knows what to do with such a gift. I know you're only, oh fuck, that's nice, get it in there deeper... I know you're only doing favors right now for the lovely ladies you've been with this year, but if you're ever interested in spreading the pleasure to some hot, older women, let me know and I can set you up. I can set you up oh so fucking nice," Mrs. Lynn moaned.

I'd buried the entire length of my cock in her by now, and though her face was a twisted grimace, it was one of those rare grimaces of ecstasy I knew so well.

"The offer's tempting," I grunted, slowly withdrawing a couple inches and slamming back home in her. "And I'll probably take you up on it, but right here, right now, I've got a lot on my plate, and I want to fuck you and only you. Maybe later we can talk about your friends, but right now, I'm going to fuck your ass so hard your eyes will roll back and you won't walk right for days."

"Good answer," she moaned, leaning back to kiss me as I began to fuck her ass even harder. "But we will talk about this again!"

"If... you... insist!" I grunted, grabbing her by the hips and pounding her tight little hole nice and hard.

It may not have been what I set out to do today, and there was every chance that it'd tire me out more than I wanted to for what I had to do the next day, but if it meant doing a good deed for Mrs. Lynn and fucking her amazing ass as hard as I could, then a little tiredness the next day was a chance I'd have to take.

***

"If I told you you ought to relax more, Ryan Collins, would you listen to me, or would you come up with some excuse that sounds noble but is mostly a very solid excuse for you to be dipping your wick in as many girls as possible?" Rose Ferris asked as she sat behind me on the couch, massaging my shoulders with her delicate-looking but deceptively powerful hands.

I thought about what she said while enjoying her efforts, then said, "It'd be a really good excuse. Well worded, probably with a fair bit of truth in it."

Rose laughed. "Oh, I'm sure it would be, I'm sure it would be. At least pace yourself when you're fucking around as you do, or maybe stretch some between sessions? Yoga does work some miracles..."

"I'll take it under advisement," I said.

"Hey, take it from an ex-cheerleader slut, stretching does wonders," Rose replied.

That she was knowledgeable in this field, I had no doubt.

Sitting on the floor of my living room wearing a t-shirt and sweatpants while Rose sat behind me, massaging my shoulders while we both looked up at the half-decorated Christmas tree, it was a distinct and very nice form of relaxation. I'd invited her over here for, well, the good deed I meant to do for her (among others), and while we waited on the other components to arrive I'd enlisted her help in decorating the Christmas tree. With her artful eye and commanding nature when it came to projects, she took charge and had done a pretty damn good job with the lights and ornaments Dad and I normally wouldn't know what to do with.

As ever, Rose was a refreshing presence, radiating an air of casual cynicism and genuine compassion that usually made her one of the best people I'd found I could talk to. Though her style was a distinctly hipster form of eclectic, with her mismatched (and some would say "trying too hard") clothes, fedora and sunglasses, she was still stunningly beautiful, with wavy, platinum blonde hair streaked blue, the fit body of a former cheerleader, and a cute face. Though I couldn't get enough of her body (especially her C-cup tits and miraculously tight and round ass), it was her smile that always commanded my attention. It was bright and confident, tired and world-weary yet always capable. It was a smile I never got tired of, and one I always looked forward to seeing.

Looking up at her and not seeing her smile... well, that was always some cause for alarm. She didn't look distressed or worried, but with her usual confidence not making a full appearance, it had me curious.

"You alright?" I asked.

Her smile flickered, but didn't make a false return. That was another thing to love about Rose; she wasn't one much for false pretenses.

"Switch places with me, and I'll gladly tell you," she said.

"Sure," I said, climbing up onto the couch while she slid to the floor, then between my legs with her back to me. I gripped her shoulders and worked them the best I could, hopeful that I was doing justice to the massage she'd just given me. Given the low groan of pleasure that came from her throat, I was pretty sure I was going in the right direction.

"I'd be lying if I said I wasn't nervous, Ryan Collins," she said.

"Which makes sense," I replied.

"Nervous about what's before me, but even more nervous about your sitcom level machinations," Rose said with only the slightest venom.

"It'll work," I said, hoping I believed myself.

"Will it? Because while I'm not one much for stale jokes and laugh tracks recorded of people who've been dead for decades, I've watched a sitcom or two in my time, and I'm going to be honest with you: any time a zany scheme, which your machinations would definitely qualify as, comes in to play, it almost never works out. In fact, such zany schemes based on deception, however well-intentioned they may be, often have a way of making things much, much worse than they were in the first place," Rose said.

"It's not like I'm inviting two girls to prom without telling them that I'd invited each other," I joked.

"You're saying you'd tell them?" Rose asked.

"Of course. I have every intention of showing up to prom with a girl on each arm," I continued to joke.

"I'm being serious, Ryan Collins," Rose grumbled.

I sighed, then thought seriously about what she said, and though her words struck a chord, they were nothing I hadn't already thought about since I began this Christmas project.

"I know that I'm taking a lot of chances, but I want you to understand that I've thought through all the consequences. However it goes, I want you to know that I am more than happy to take all of the responsibility and whatever shit comes out of this. I'll do everything in my power to make sure that none of it splashes back onto you if it goes south," I said.

"Well, that's certainly something," Rose replied.

"But, call it my own sense of seasonal optimism, but I don't think it'll explode. Maybe it will a little, at first, but I think everything's going to go quite well once we really get to talking," I said.

"And you're basing that on?" Rose asked.

"Hope. The power of Santa or Jesus or Krampus or whatever you believe in. The immense luck and contrivances my life has worked off of this year that, so far at least, haven't guided me that wrong yet," I said.

"Considering that you've been doing this Christmas extravaganza as a form of penance, pardon me if I don't entirely share your faith in your improbable luck," Rose said.

"Well..." I trailed off. She did have a point there. I'd had a lot of strange luck this year that had led me to a number of great places, but almost as many bad ones.

Kyle Bowman.

Losing Tori's friendship.

I could hope as much as I wanted to do that this mad plan would work, but there was every plan it might explode and make things worse. As much as I wanted it to blow back on me, I couldn't control all the variables, I couldn't guarantee that it wouldn't come back and bite Rose as well.

"I'm sorry. Do you, uh, want me to cancel? There's still time to stop this, I think," I said.

Rose sighed, lowering her sunglasses just enough to rub the bridge of her nose. "No, I'm sorry. You're trying, which is a lot more than most people are doing these days. Most people are content to just let things lie as they are, letting the bad stuff grow and never letting the good things gain strength. You're trying to do something good for me, for all of us really, and for that I should be thanking you, not condemning you. What you've initiated is a confrontation that's needed to happen for far too long and that I've avoided out of a complacent fear, and you've convinced me to face it. I only hope you're able to convince the others."

"I can be pretty persuasive," I said, confidently working out a knot in her neck.

"It'll take more than a slick tongue and a thick cock to heal these wounds," Rose said, before adding, "But I'd like to see you try."

The doorbell rang. Rose tensed up in my hands.

"You aren't by any chance expecting anyone else today?" Rose said, her voice equal parts skeptical and hopeful.

I shook my head. "Dad's out all weekend and I'm not expecting any deliveries."

The doorbell rang again and again, each time more urgent than the last.

"Then I guess it's time," Rose said.

I stood up. "We'll make this work."

"Here's hoping," Rose said, little confidence in her faint smile.

Straightening my clothes out and taking a deep breath, I walked to the door. This was something I could do, and for Rose and the others this was something I had to do. I'd pulled off a few Christmas miracles already, and this would hardly be the biggest of them, but it would sure as hell be one of the most difficult.

I took a breath and swung the front door wide open.

"Merry fucking Christmas, Ryan!" Brooke King announced proudly from the doorway.

A tiny and cute as a button cheerleader with a petite build, lightly tanned skin, brilliant blonde pigtails and a nice round butt that stood out in contrast with her small A-cup tits, she was one of my longest held and most energetic lovers I'd come to know this year. A ball of pure energy and, on the surface at least, the perfect cheerleader stereotype, she was also one of the filthiest fucking girls in the entire school who'd led to some of my more memorable sexual adventures. She'd been part of my inner circle of trusted confidantes helping me out with my Christmas plan, but I'd had to keep her out of the loop for this part. She'd foregone her usual pink clothes today in exchange for a tight and revealing green Christmas elf outfit, cut low to reveal what little cleavage she had and with a skirt high enough you could see her bright red panties just above her red and green striped knee socks.

She wasn't alone.

Standing next to her was her exact opposite number in the wildly curvy redhead, Haley Campbell. While Brooke was bubbly and effervescent, Haley was surly and the poster child for a resting bitch face. While Brooke was tiny and petite, Haley was half a head taller than her and the very definition of voluptuous, with wide hips and a nice, juicy ass that formed a near perfect hourglass shape with her absolutely insane H-cup tits. With pale skin that complimented her long, straight red hair and ruby red lips, she'd have been a knockout if it weren't for the perpetual bitchy sneer on her face (though she still looked pretty fucking amazing) that always made her look like she thought she had somewhere better to be. Dressed in a sexy Mrs. Claus sort of outfit that on her body was even more insanely revealing than Brooke's costume, she was utterly mouth-watering.

Save for sharing bright green eyes and both being cheerleaders, the two girls couldn't have been any more different. That would make today an exceptional challenge, but one I was willing to undertake.

"So, are you gonna fucking let us in or are we just gonna stand out here freezing our asses off?" Haley asked, tapping her foot impatiently.

There was the Haley Campbell I more or less knew.

"Oh, come on, Red, have a little Christmas spirit why don'tcha?" Brooke said, chiding her friend.

"Come on in," I said, ushering both of them inside. They were both clearly expecting some sexy fun off the bat, and I knew I had to nip that one in the bud if we were going to accomplish what I wanted to. "Before we get much further than the foyer, there's something I ought to tell you two..."

"Ooh, is it a surprise? I, like, totally love surprises!" Brooke exclaimed, wrapping her arms around my neck and kissing me on the cheek.

"I don't," Haley said.

Brooke rolled her eye at her friend. "Don't mind Red, Ryan, she gets all sorts of cunty this time of year, but she'll be bouncin' on your beast in no time. So, what kinda surprise do ya got for us, huh?"

I laughed nervously. "About that..."

***

I never got the full story of what happened when Rose quit the cheerleading squad, but from what I was able to put together from details culled from Rose, Kaitlyn and Brooke, it was ugly.

Very ugly.

Rose had been one of Regan Hills High School's best cheerleaders, and pretty much the only one who wouldn't take shit from head cheerleader Dakota Lewis and stop her when she was on one of her many power trips. While Dakota could intimidate even the likes of Haley, Rose always knew how to shut her down with the slightest effort. Because of this, Rose had gained this impossibly cool image among the other girls and became the kind of person that a lot of them looked up to.