Spring Break Memories

(Usual Disclaimer Time: All the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time (often in regards to a character's proportions), please remember it's all in good fun.)

Author's Note: This story requires a little explanation before we get too deep into it. Spring Break Memories is a much-requested spin-off miniseries from my long-running Senior Year Memories, taking place between chapters 50 and 51 of that tale. All of you who have read that far in the story will hopefully enjoy the continuation of various storylines and returning characters, but as for the rest of you, I want to let you know now that it is NOT necessary to be a Senior Year Memories expert to enjoy this story. I'm doing my best to write it as both a continuation, and a story that will stand on its own for the reading pleasure of those who might not want to go through all 50+ chapters of the main series. I like to keep things light, fun, thoroughly cliched and more than a little unrealistic, so I hope you all enjoy!

Further, I would like to thank the readers whose votes helped determine some of the action of this story and picked the majority of the girls who would make appearances in it, particularly this chapter's leading lady, the one and only Kaitlyn Pruitt; you guys are, as ever, the best!)

***

Spring Break had flown by so quickly, I'd barely noticed it was finished by the time I'd gotten there, but as the calendar rolled down and school crept up on me again, I prepared to bid a bittersweet adieu to the holiday. While previous school Spring Breaks had mostly meant me just hanging around the house while everyone in school had all of their adventures, this year *I* got to be the one having the adventures, and I fucking loved it. I'd spent the past six days getting up to all sorts of fun with Haley, Olivia, Sabrina, Tori, April, Sarah and Alice, and I knew that the memories we made together would be ones that I'd hold onto for the rest of my life.

Nevertheless, that bittersweetness still remained as we reached the end of this final Spring Break I'd spend at Regan Hills High School, but even that feeling couldn't take me from the excitement of that final day, either.

Because my *final* Spring Break adventure meant I'd get to spend my time with 18-year-old Kaitlyn Pruitt.

Kaitlyn was the girl who'd started it all, this year, and to say I owed her everything was a bit of an understatement. Though we'd been friends when we were younger, we'd drifted apart with time as she became beautiful and popular (and a bitchy, mean girl of a cheerleader at that) and I just got to be more of the pale, skinny nerd I'd always been. We'd only really reconnected earlier this year when I was asked to tutor her in history, and when she'd thought it might be easier to seduce me rather than engage in tutoring, well... in short order, she was impressed by the size of my cock, took my virginity, and set off a chain of events that had led to my debaucherous senior year. I'd had so much sex and made so many new friends all because of her trying to get out of history tutoring, and even if it had its speed bumps along the way, I wouldn't have traded anything for the life that she'd introduced me to.

Since she was the one to begin everything, it only seemed to make sense that we finish out Spring Break together, even if I didn't necessarily have an idea of what she had in mind. She had been purposefully vague and mysterious (a trend, admittedly, of several of the girls I'd spent my Spring Break with), only letting on to the fact that it would be late in the day, and would be the kind of memory that I'd never forget.

Knowing Kaitlyn, I didn't doubt her for a second.

***

It was well after 9 pm when Kaitlyn finally came by to pick me up, shooting me a text to meet her out in front of my house. Not knowing what I was in for, I kept it simple, tossing on a graphic tee, jeans and shoes and making my way out to meet her.

It was a warm night, one that felt closer to summer than to the spring that it was, and one that I breathed in richly. Memories of Spring Break rolled through my mind, of lust and good friends and adventure, memories that brought a smile to my face and made me wish that this experience never had to end. It was as those memories took another turn toward the bittersweet that I saw that familiar car pulling up, and I walked up to meet Kaitlyn with a renewed spring in my step.

Seeing her had a way of doing that to me, after all.

I dropped into the passenger seat beside her.

Smirking at me, Kaitlyn said, "Hey."

"Hey," I replied, looking on her in some awe.

Sitting next to Kaitlyn had a way of making me feel underdressed no matter what either of us were wearing, but looking the way she did tonight made me even more acutely aware of this feeling. The 5'3", raven-haired beauty had a tight body from years of dance and cheerleading and lightly tanned skin that came with a certain familiarity of lounging around by the poolside. Tonight, it seemed like she was trying to figure out how little she could get away with wearing, as her barely there cutoff jeans looked like little more than underwear (even with her black thong sticking out of the top) and did little to hold in her full, round ass, and a stylish black top that did a remarkable job of holding in her impressive DD-cup tits. She was showing enough skin that this outfit honestly probably could've qualified as a swimsuit, showing off her shapely legs, tight abs and enough cleavage that it could probably be seen from space. Top it off with her model gorgeous face, full, pouty lips pursed in a cocky little smile and expressive brown eyes that sparkled with mischief, and I was hard already at just having a glance at her.

Then again, the mere *thought* of Kaitlyn would often get me nice and hard, so that was probably not the most exceptional moment to note.

As I buckled in, Kaitlyn took off, driving us down the darkened roads of Regan Hills with an amused, focused look on her face. Unable to help myself, I slipped a hand between her legs and squeezed her thigh. With a pleasant little moan, she parted her legs for me, giving me better access to grope her while she drove.

"So... am I gonna get any clue about what we're doing tonight?" I asked.

Grinning cockily, she replied, "Well, we'll be fucking by the end of it, if that's what you're worried about."

"But there's always sex by the end," I replied, squeezing her thigh playfully.

"True, but that's still the only clue I'm gonna give you," Kaitlyn continued, chancing a glance over at me before she turned her attention back to the road. "So, you have a good Spring Break?"

"Yeah, I won't lie, mine was pretty great. How about you?" I asked.

She shrugged. "Parking myself in a bikini by one body of water or another while listening to Mom and my stepdad pretend that they're not arguing and wondering whether or not they're going to last past the end of the year, so, about the usual."

I knew Kaitlyn's mother, Cassandra, well, as she had often looked after me back in the day, and I'd be lying if I said she hadn't been one of my earliest crushes. At the beginning of senior year, I never thought I'd see Mrs. Pruitt again, but when Kaitlyn reentered my life, our paths crossed yet again, and as things tended to do this year, well, Mrs. Pruitt and I did make each other's acquaintances again. *Intimately*. That I had hooked up with Mrs. Pruitt a number of times over the course of senior year certainly complicated matters with how I felt about the Pruitt family, not that I regretted any of what we had done, but it did make some moments with Kaitlyn awkward in their own unique way, especially when she'd bring up her parents' relationship.

"Sorry," I replied.

"Nothing to be sorry about," Kaitlyn said, shrugging again. "Like I said, it's about the usual, and it's not your fault... these problems go back before you came into the picture again, if that's what's on your mind."

She shot me a little, knowing smirk, that at once gave me a little surge of anxiety and relief. Kaitlyn teasing me about how I occasionally fucked her mother was nothing new, but she certainly liked to have her fun with it. While her mean girl tendencies had mostly disappeared as we had become better and better friends, she did like to show her claws off every so often. It was never as pointed or as cruel as it used to be, so when she pulled this sort of act these days, I couldn't help but feel a strange attraction to her.

Not that there was much that could be done to make Kaitlyn *un*attractive to me. She had always been one of the most physically beautiful people that I knew, and as we'd forged a new kind of friendship, one that started with sex and had become something more, we had become strangely integral elements to each other's senior experiences. Even if we weren't together, and likely never would be a couple in the traditional definition, the two of us were inextricably linked in a way neither of us could avoid, the chemistry between us electric whenever we were in close proximity to each other.

I tried to resist the urge to grope her while we were driving, but that kind of trying was futile when they came as sexy-looking as Kaitlyn. I reached over to her, squeezing one of her tits playfully, groping and massaging her through her top.

"Mmm, fuck... you know I'm driving, right?" Kaitlyn moaned, conspicuously not asking me to stop.

"So?" I asked, continuing to squeeze her tit. "I've fingered Brooke before while she's been driving, she has no problem with it."

"Yeah, well, you and I... fuck... we know better than most that Brooke's a unique kind of slut," she explained, arching her back slightly to press her breast against my hand. "She can do things most other people can't."

Smirking, I replied. "You want me to stop?"

"Fuck no," Kaitlyn replied, grabbing my hand and slipping it into her cleavage. "But if you're gonna grope my tits, do it skin to skin... feels so much better with your hands... fuck."

That was an easy enough request to comply with. I held my hand in her cleavage for a moment, squeezing and groping one of her breasts, before I slid it around the front and slipped it underneath the thin fabric of her bra. Kaitlyn moaned softly as I snaked my fingers in deeper, teasing her nipple which hardened quickly to my touch.

"That about what you were looking for?" I asked, grinning at her smugly.

"Yeah... yeah, that's about right..." Kaitlyn purred, looking over at me for a moment with a lustful smile before turning her attention back to the road. "You can keep doing that, too... just don't get too excited; we have something important to do once we get to where we're going."

"And that is...?" I asked, trying to coax more details out of her by squeezing her nipple.

"You'll find out," she replied, biting her lip and rocking her hips in her seat as the pleasure of my touch was clearly doing some darkly delicious things to her.

I did the best I could with her, but all credit to Kaitlyn for holding a secret, because I truly had no idea of where we were going until we'd nearly gotten there. I was able to figure out that we were heading up to the hills, which only raised my curiosity; as I've mentioned before, it's a common joke in town that Regan Hills isn't all that hilly, and those hills that were there were mostly where the rich families in town lived. I'd come up here earlier in the week when I spent my day with the stacked redhead Haley Campbell, but Kaitlyn taking me here was a bit of a surprise.

"We're gonna go visit Haley?" I asked, curious.

"I'll give you a spoiler there: no, we're not visiting Haley," she replied, smirking. "Not that I haven't been wanting to sit on that bitch's face for a while now, but... no, that's not where we're going."

With a knowing grin, Kaitlyn added, "Tonight... tonight we're going to make ourselves *legendary.*"

Now, this was a perfectly mysterious thing for her to say, and if she wanted to keep it a mystery, she probably could have, but once I put her words together with the winding roads that I could somewhat recognize, I knew *exactly* where she was taking me. I didn't know if where we were going was necessarily the place for us to be legends, since it was kind of a place all Regan Hills High kids went at one point or another before they graduated, but as it was one of those places I hadn't expected I'd ever be popular enough to find reason to head to, it still took me by surprise that Kaitlyn was leading me here.

Nevertheless, I was more than a little excited that we were headed to the Regan Hills water tower.

A massive, white water tower that loomed at the top of one of Regan Hills' few actual hills, it had been many a year since it actually had any water in it, now serving more as a beacon to those who came to town with it's blocky black letters welcoming people to REGAN HILLS. As it hadn't been lit up at night almost as long as it had had any water in it, it was a popular location for people to drive up to and get high or laid at... but for the brave among us seniors of Regan Hills High, the tower also held something of a rite of passage. To those brave enough to climb the ladder up to the catwalk that encircled the water tower, it was traditional for graduating seniors to graffiti their names somewhere on the tower.

The tower looked down upon us ominously as Kaitlyn drove past a number of 'DO NOT ENTER' signs, parking at the small lot at the water tower's base. Unexpectedly for the end of Spring Break, we were the only car actually here tonight, which either meant some good fortune on our part, or Kaitlyn had put out the word for people to stay the hell away. Whatever the reason was, I was glad for it, as I was glad to have any time with Kaitlyn to myself.

Finally parked, Kaitlyn pulled my hand out from under her top and smiled at me. "Ready to live a little dangerously?"

Truth be told, the size of the tower up close was more than a little intimidating, but with Kaitlyn here with me, any true fear had a hard time taking hold inside of me, replaced by an eagerness to take on this new adventure.

Kaitlyn took off her seat belt, reaching to the seat behind her and pulling out a couple pairs of work gloves and a magic marker.

"Gloves?" I asked when she passed me a pair.

"The ladder can be a little rusty, these are so you don't mess up your hands," Kaitlyn explained.

I put them on. "Climbing a rusty ladder so we can make ourselves legendary... yeah, that definitely sounds like living dangerously."

"I've done this before... trust me, it's safe. Well, *pretty* safe, so long as you don't do anything stupid. You aren't planning on doing anything stupid, are you?" she asked, smirking as she slipped her own gloves on, quickly pocketing the marker.

I shook my head. This sounded like one of the more damnfool ideas that I had ever considered doing for the sake of a pretty girl, but that didn't change the fact that it was one of the prettiest girls I knew who was asking me this. I was pretty sure there was nothing I would ever refuse her, and I doubted I was going to start tonight.

"Alright... lead the way," I said, stepping out of her car.

I looked up at the water tower, finding it more impressive and imposing with every passing moment. Though I rationally understood that it probably wasn't more than 50 or 60 feet tall, from down here it looked like it stretched up into the night sky. It seemed impossibly high, the low creaks coming from it as the cool night air reacted to it sounding like the wild, violently loud sounds of rending metal in my overactive imagination. I looked to the nearest support leg, the one with the enclosed ladder attached to it, and I could swear that the faint sheen of rust I saw on the white painted ladder meant that it was corroded to a point of collapse. Suddenly, in the dark of night, this looked like the worst idea in the world, the stupidest thing that anyone had ever considered, how had I been talked into doing something this foolish and-

SMACK!

Kaitlyn playfully swatted me on the ass, walking beside me and looking up at me with a bright, cocky little smile.

"I'd apologize, but your ass looked good, and I don't think that's any reason to apologize for," she said, quickly pulling me in for a kiss before continuing, "You ready?"

What was I afraid of again? "Let's do this."

***

Since I'm here writing this now and am decidedly not a ghost, I won't bore you with all the details of how I didn't die, and will just say that the climb up to the tower's outer catwalk (about halfway up the full height of the tower itself) was relatively uneventful. Kaitlyn went up the ladder first, giving me a great view of her ass in those tight cutoffs, and when you're focused on staring at something like that, the dark and the possibility of the entire water tower collapsing beneath us seemed remote and far away, though the fact that the ladder had an enclosed safety cage surrounding it certainly did much to improve my spirits.

Once we got onto the catwalk, my legs suddenly felt much sturdier, and with a hand on the railing for support, I could trust the stability of this ancient structure more and more. I looked out over town, seeing the lights of Regan Hills seeming so small and far away, and yet so *alive* at the same time, bringing out great feelings of home and belonging that brought out an unexpected warmth from within me. Looking around at the tower itself, I saw its side graffitied with hundreds... hell, *thousands* of signatures from generations of past Regan Hills High School seniors, decades of history unfolding before me. It was a heady feeling, and that I was here with Kaitlyn made it all the more surreal an experience.

I shouldn't be here... at least, the *old* me shouldn't be here. The Ryan Collins who'd begun senior year was an inconsequential nobody, but now... fuck, being here with Kaitlyn like this felt strangely right. Even if it felt hard to believe sometimes, I'd earned my place here, and I felt honored to be taking part in this ritual with Kaitlyn, one of the most beautiful girls in school, and someone I was happy to call one of my best friends.

"Come on, this way," she said, cocking her head with a confident little smirk. "Let's find a good spot up front."

I followed her as she led me under the large black letters that spelled out our town's name.

"It's better up front? I'd have thought that would all have been filled up by now," I said.

"I thought the same, but even for all the people who've made it up here, I think a lot of them freak out when they see town and just go around back thinking they won't be noticed... but, fuck it, nobody can see us from up here, and you don't get legendary by signing the back, do you?" Kaitlyn proposed.

That made sense. "So, where'd you sign it last time? You said you came up here before, right?"

She laughed. "Yeah... yeah, I came up here. It was around... early October, I wanna say? Dakota wanted to get the whole cheer squad up here... most of us made it, a few chickened out before the big day and said they had other plans, and when we got to the ladder, another couple girls decided that they didn't want to go up... but still, most of us climbed up here, doing our big, stupid, senior year kind of thing, and we did it. Most of the girls went around back, some hung off on the sides and found their own places, but Dakota, Brooke, Cleo, Gwen and me... we all found ourselves a spot under the R and made ourselves fucking legendary. And tonight, we'll find one for you to join in on this, too."

All of this made sense to me, and though I could feel that same psychological fallacy worrying that we'd be seen, given that the tower wasn't particularly well lit, I knew we were every bit as in the clear as she claimed we would be.