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Ass

(Usual Disclaimer Time: Even though this story almost entirely takes place in a high school setting, 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, please remember it’s all in good fun. This story is highly serialized, and though it’s not 100% necessary to have read the whole story up until this point to enjoy the content of the chapter, it’s definitely advisable to understand some of the ongoing plots.)

(Author’s Note: I’d like to again thank MisterWildCard for acting as a second set of eyes on this chapter and for his honest editing and fantastic suggestions. Please check out his story, “Brooke’s Wild Ride” in Erotic Couplings, as it acts as a canonical side story to Senior Year Memories starring Regan Hills High’s favorite blonde cheerleader.)

Previously, on Senior Year Memories: 18-year-old Ryan Collins’ quest to do something nice for each of the nineteen women he’s had sex with this senior year before Christmas has continued at a swift pace. With assistance from cheerleader Jade Alvarez, Ryan got a discounted gym membership to athlete and aspiring Ninja Warrior Noa Kanzaki. Not long after, his offer to tutor more students pleased Mrs. Lynn to no end (as did his cock). The true challenge came when Ryan sought to reunite cheerleaders Brooke King and Haley Campbell with their former friend, ex-cheerleader Rose Ferris. Though the other girls had once shunned her for quitting the team and becoming a hipster, with some convincing from Ryan, the other girls reconsidered their opinions and made peace with Rose. Naturally, because this is that kind of story, a hot foursome ensued. With seven names remaining on his list for good deeds, who will Ryan help next?

Names Remaining on Ryan’s Christmas List: Addison, Jade, Josie, Kaitlyn, Mallory, Nadia, Sophie

***

From September to November of the year I’m chronicling, I had sex with nineteen women from and around the periphery of Regan Hills High School, and by December I’d come to know a lot of them in different ways.

Like Brooke King, some of them were new friends.

Like Kaitlyn Pruitt, some of them were old friends made new again.

Like Mrs. Lynn, some were longtime crushes.

Like Rachel McNeil, some of them were old enemies made new friends.

Like Tori McNeil, some of them were old friends made… well, not friends anymore.

Like Josie Wong, some of them had even become more than friends.

I knew a lot of the girls I’d been with quite well and considered more than a few of them very close. If it weren’t for the weird incest vibes, I’d even say I felt like a lot of them were family, but since that’s a little weirder than I mean to go, I’ll just say that I was really good friends with some fine women, and couldn’t have been happier for it.

The tricky thing, though, was that I didn’t know every girl I’d been with all that well. Sometimes it was because they were just a passing encounter, while other times it was just a matter of lousy scheduling and not being able to see any of them again. While there was nothing wrong with this, it did create some particular problems when trying to do something special for each of those nineteen women.

Take Addison Gonzalez, for instance.

That the 18-year-old cheerleader and homecoming queen was gorgeous was undeniable. The short, lean Latina had a kind, beautiful face with deep, friendly brown eyes and a bright smile that she loved to use often. With curly black hair that fell about to her mid-back and soft brown skin, she had a face made for magazine covers. Her body, however, was made for porn, with a tight, dancer’s build, E-cup tits that she loved to have touched and an even bigger ass. I’d had sex with her on Homecoming while she wore her gown, sash and tiara, and found her to be a kind and enjoyable lover.

The problem was, unlike many of the girls I’d been with this year, I never really spent any serious time with her after Homecoming. I knew she was a kind and gentle person from reputation and what little time I spent with her, that she had lousy taste in boyfriends (if Kyle Bowman was any indication), and that she was friends with Kaitlyn and loved to throw parties and have fun with the rest of the cheerleaders, but beyond that she was a mystery. When I wanted to get her a gift during my mad Christmas plan, I thought it would be an easy task, one where I’d just have to ask one of my many Christmas co-conspirators from the cheerleading squad who could give me an idea of the sort of big thing she’d like.

The problem with that was, well, that most of them weren’t of much help either. Jade and Rose were never particularly close to Addison, and though Brooke and Kaitlyn were closer, the most they could tell me was that in many respects, despite her outgoing exterior, Addison was a fairly private person when it came to what she really liked.

If I wanted to know what Addison kartal escort would have liked, it came down to asking her myself.

Still, when I went to her house and found myself with her in her bedroom and its walls pretty much plastered with posters for Disney movies and princesses, I didn’t quite expect the answer she gave me.

“Revenge?” I asked.

She nodded. “You asked me what I wanted, and what I want is revenge.”

“I heard you, I just didn’t expect… revenge to be part of your vocabulary,” I said.

She sat down on her bed, smiling that winning smile. Wearing a pretty blue dress and a very fluffy pair of slippers, she looked perfectly comfortable and at ease, not someone who was, well, asking for my help with revenge.

“I’m a cheerleader. I’m the Homecoming Queen. I’m *not* stupid,” she emphasized.

“I never said you were, I just thought…” I waved my arms around at her room.

She looked around, then rocked her head side to side slightly. “Okay, I can understand where you’d get some of that idea.”

“And you being really nice,” I said.

“There’s that, too,” Addison said.

“So, you’ll understand why it might catch me off guard that you’re looking for revenge?” I asked.

“I wasn’t looking for it. Not until you came in here. Until you came in here, I was a girl with a problem she didn’t properly know how to deal with, but now? Now I have you, who wants to help me, and a mutual enemy we both hate,” Addison said.

Though I was confused for a moment, that moment wasn’t a long one. “Kyle Bowman.”

“Kyle Bowman,” she repeated, patting the bed beside her.

My last encounter with Kyle Bowman was at Homecoming, and it was a bit of revenge of my own in response to him assaulting me a few days before. With the help of Kaitlyn, Brooke and Tori, I was put in a position at Homecoming where I could humiliate him by having sex with Addison, his girlfriend at the time and the Homecoming Queen to his Homecoming King. Couple his humiliation with the reveal of some of his low level criminal activities and, well, expulsion was easy to come by. Last I heard, he was at some private school back east where rich parents sent their problem kids.

Was wrapping myself up in the fucked up world of Kyle Bowman something I wanted to do again? Did I really want to press my luck by helping Addison seek revenge on him?

I sat next to her. “Talk.”

She sighed. “There’s not a lot to talk about, but I’ll try to make it quick anyway because… yuck. After he got expelled, Kyle was texting me like crazy, trying to apologize and forgiving me for fucking you and telling me about how everything was a frame-up, but it wasn’t, was it?”

“Well, we did frame him up, but it was for stuff he actually did, so I’m not sure what the official wording would be,” I admitted.

Addison nodded. “Sounds right. Well… I thought I could ignore him. Block his number, change my number, but he kept finding a way in, kept trying to contact me and… I just hoped he’d lose interest, but he turned out to be a lot more persistent than I thought. He was… he wasn’t the guy I thought I liked before. He started saying things. Vile, personal things. The kind of things, like… it made it feel like he thought that just because we had sex before, he felt he had a right to control what I did with my life, that he had some sort of claim over who I was just because we’d been together. He wanted to make me feel like less of a person because I wasn’t the girl he wanted me to be, and…”

She trailed off unhappily, but it was easy to pick up where she was going. I said, “…and after a while it became difficult to not believe him, even in just some little way?”

Addison nodded. I said, “Kyle’s got a way of doing that.”

“I don’t want to let him have that kind of power over me. I don’t want his words, or the pictures and videos he’s been sending of him with all these random girls… I don’t want any of them to have any power over me, because I don’t want that son of a bitch to take up any of my thoughts anymore. So, that’s why I’d like your help for a little revenge,” Addison said, standing up from her bed.

“What do you need from me?” I asked, eager to help.

Addison smiled. “Something you’re uniquely qualified to provide.”

Reaching up, she pulled off the shoulders of her dress, dropping it to the floor around her ankles and revealing herself to be quite deliciously naked, save for her comfy slippers.

Sensing where this was going, my cock twitched in anticipation.

“I’m listening,” I said, smiling.

Sauntering over to her desk nearby, she toyed with her phone for a moment and propped it up so it was facing the bed.

“He thinks he can break my spirit by screwing random girls, well, I want to show him that not only doesn’t it work, but that two can play that game. I want you to fuck me as hard as you’ve fucked any girl in school, to make me scream, and believe me I intend to scream. I’m going to scream about how lousy a lay that maltepe escort bayan bastard was and about how you’re so much better, and about how he means absolutely nothing to me. I could fake it if I have to, but I know you’re good, and I know you can make it so, so real,” Addison said, her hands dropping to her pussy and fingering her sweet, moist lips. My mouth watered at the sight, and it was now decidedly uncomfortable to sit still with how hard my cock was.

“So, Ryan, what do you say about helping me with a little revenge for Christmas?” Addison asked.

Looking her up and down and taking in her massive, sweet tits, I’d have been a fool to say anything but “yes”. Even so, when she spun around, showing off her juicy, round ass, squeezing her bountiful flesh in a way that would’ve raised the dead, I thought my answer to be a pretty easy one.

I unzipped my pants and pulled out all ten inches of my thick, hard cock. “I’d say: Merry Christmas.”

***

There were few joys in life I found greater than spending a nice, quiet moment hanging out with my girlfriend, Josie Wong. It was still something worth marveling at, that I could so freely use the term girlfriend, and that it in no way interfered with my social life as long as I didn’t interfere in hers. I never really expected that I’d have a girlfriend in high school, let alone a curvy goth princess who could make me laugh as hard as her (and whose ass I found particularly hypnotizing), but here we were, and here I was, possibly one of the luckiest guys on Earth.

Sitting in a quiet booth with her on the second floor of Marsters’ Secondhand Books, waiting for our drinks (and someone in particular) to arrive, I was feeling pretty good. After being all too happy to help Addison with her video to get back at Kyle, I only had six names left on my Christmas good deeds list. It was strange, reaching the end of such a long road, but it was a road I was looking forward to the end of.

I didn’t know that, sitting here and talking with Josie, that I’d soon discover a complication that would change how the latter half of this year would go. Like many such discoveries in life, you don’t know at the time how major something’s going to be until its impact is fully felt, and this one was definitely one of those. I still had a few moments of blissful unawareness, sitting around and feeling the holiday spirit and a strong sense of love for Josie Wong without anything adding further complication.

I knew that she looked a little nervous, and I figured that it was just a matter of time before she told me why.

“So… there’s something we gotta talk about,” Josie said.

There we go.

“What’s up?” I asked.

She bit her lip nervously, then let out her breath in one heavy sigh. “Ah, fuck it. I know we’d talked about spending most of winter break together after you’re done with all your Christmas plotting, but…”

“But what?” I asked.

“…well, I’m not gonna be here for winter break after all,” Josie said.

“You’re not?” This hit me in the gut far more than I expected it would. I didn’t have any claim on her time, but I was really looking forward to having some good time with her and nothing else on my plate in the coming weeks.

“My grandmother on my dad’s side, she’s going in for cancer surgery right after Christmas-“

“Shit, I’m sorry,” I interrupted.

Josie shook her head, a slight smile building on her lips. “Don’t worry about it; she’s tiny and frail-looking, but the bitch is indestructible. This would be round four with cancer, and she’s gonna kick it’s ass again.”

“Sounds like you admire her,” I said.

“The toughest lady I know? Yeah. Yeah I do. But that’s beside the point; the point is that Mom and Dad want to take us to spend some time with her while she goes through surgery and recuperates, which is gonna be a couple weeks. Maybe longer. I love her, but I don’t really wanna go for that long,” Josie said.

A couple weeks, maybe more, without Josie Wong. It said a lot for how close we’d grown that I wasn’t looking forward to this at all, and that I knew I’d miss her terribly. Sure, we could probably text and Skype, but I liked having her close. I liked to touch her, the sound of her laugh, to make her cum in her own powerful way…

“Will we still have Christmas Eve?” I asked, hopeful that at least some of our plans might still come together.

“Of course. I know I’ve got something I’d like you to unwrap and have some… fun with,” Josie said, running her foot up against my leg, her voice full of promise.

“Sounds promising,” I said. We’d had some discussions, nothing heavy or serious yet, to expand our horizons and maybe get a little (or a lot) kinky with our Christmas gifts for each other. I had an idea that I was a little nervous about, but one that I thought might prove fun.

I finished, “I’m still working on your present, but I’ve got a line on it for tomorrow.”

“Goodie,” Josie said, licking her full, painted black lips. I escort pendik really, really wanted to take her then and there, I’m not gonna lie, but I still had enough propriety to keep my head together and not do something that’d completely embarrass myself.

No, I’d save that enthusiasm for private, later.

“So, where’s this not-really-a-vacation gonna be?” I asked, trying to lighten the conversation further.

“Hawaii,” Josie admitted.

“Winter break in Hawaii? Beaches and sun and surfer dudes? You sure you don’t really wanna go?” I teased.

Pulling the top of her black coat open wide enough to show some of her pale, creamy cleavage, Josie sarcastically said, “Yeah, I really look like the beach bitch type, don’t I?”

I laughed. “Point.”

“Though I wouldn’t mind getting gangbanged by some ‘surfer dudes’; might be about the only thing I could do that’d keep me from missing your cock for a few minutes,” Josie purred.

I knew I should’ve been jealous at the image, but it was hard not to instead be turned on by it, to be honest. “Well, if you swing it, be sure to send pictures.”

Josie raised an eyebrow. We’d talked plenty about my exploits with other girls since we’d sort of become an item, but hadn’t really talked much about her being with other guys. That I was every bit as encouraging of her as she was of me seemed to take her by surprise, but not in a bad way. (And for those of you who love to speculate, no, this isn’t what caused the complication with us; that’ll come up in a few chapters.)

Finally, she said, “You’re on.”

“Good,” I replied.

“And you better tell me every juicy fucking detail of what kinda trouble you get up to while I’m gone,” Josie said.

I laughed again. “You know I will.”

Josie was not to be quieted that easily. “I want pictures. I want descriptions. I want tales that’ll make me want to fuck you into unconsciousness when I get back. I want-“

“I hope I’m not interrupting a… private moment?”

We both looked up to see the barista from the coffee shop downstairs standing nearby with our two drinks and an amused grin on her face. With most of the baristas working here, that would have been an embarrassing moment, but when that smile belonged to the beautiful face of Mallory Dourif, that was something I could live with. Tall, willowy and beautiful with soft, pale skin, a light dusting of freckles across her cheeks, bright blue eyes and a shaved head, she was an unconventional beauty but undeniably one of the prettiest girls in senior class. I’d been with the beautiful cosplayer a couple times in October, and though I hadn’t spent nearly as much time with her since as I would’ve liked, seeing her brought a familiar stirring in my pants.

“You aren’t. Nothing more than usual anyway,” Josie said.

“Hey,” I said to Mallory.

“Hey,” she replied, sliding into the seat next to me. “You said you wanted to see me when I was on break? Well, I’m on break. What’s up?”

I’d come up with a whole speech about what I meant to do for Mallory and why, but when someone who can be as blunt as Josie Wong is sitting next to you (and is an integral part of the plan), things have a way of getting a little off script.

Before I could say anything, Josie said, “You hear about how Ryan’s been doing his own naughty and nice thing for Christmas? Making a list and checking it twice, getting presents for all the girls he’s screwed and all that?”

“I could’ve said that,” I whispered to her.

“Yeah, but it’d have taken a while; I just helped you break the ice,” Josie replied easily, smiling so cutely I couldn’t hold anything against her.

Blushing slightly, Mallory replied to Josie’s question, “Some. I’d heard rumors, that something bad’s happened to you, but I didn’t really think much of them. What happened? Are you alright, Ryan?”

Though mildly annoyed with Josie, I said, “Yeah, it’s… it’s a long story.”

“Well… I’m sorry to hear you’re having some rough times. If you ever want to talk with someone with an intimate knowledge of rough times, I’m here,” Mallory said, placing her hand on mine for a moment.

“Thanks,” I replied. I turned to Josie. “Do you wanna finish this, or can I?”

“It’s all yours,” Josie said, sipping from her coffee and sighing contentedly.

I returned to Mallory. “So… yeah, I’ve been doing something for every girl I’ve been with, and-“

“You don’t have to. For me, I mean, if that’s why you’re here; if you want to for everyone else, you can, that’s for you, but there’s nothing I need, honestly. Thank you, though, for thinking,” Mallory said.

“I want to, though,” I said, squeezing her hand back. “Good people deserve good things, and you’re about as good as they come.”

Mallory blushed.

“You should at least hear what it is before you turn it down,” Josie suggested.

Mallory bit her lip, her eyes cast to the side as if in deep thought. Finally, she said, “Okay. I’ll hear what you have to offer before I say anything, even though I’m probably still going to say no.”

“But you’ll wait ’til you hear me before saying no?” I asked.

“I’ll wait,” Mallory said.

I took a deep breath, hoping I could pull this off. “So… how much, on average, would you say cosplaying glamour shots go for?”

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