Senior Year Memories Ch. 19

(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: After Thanksgiving dinner turned disastrous from an ill-considered tryst and ruined his friendship with longtime best friend, Tori McNeil, 18-year-old Ryan Collins was in a dark place. Fortunately, he had good friends who wanted to get him out of that dark place. A talk with Tori's older sister (and also Ryan's one-time lover), Rachel, helped him ground himself, while a discussion with long term fling, goth princess Josie Wong, led to the two of them finally admitting that they loved each other. The true turning point came when, by coincidence, Josie and cheerleader Brooke King each sent one of their friends to cheer Ryan up and help him get his head on straight. Josie sent band geek and kinky sex fan Hope Harris, while Brooke sent a fellow cheerleader, the busty Latina Jade Alvarez, who'd had her eye on Ryan for some time. After some hesitation, the promise of a naughty and nice threesome full of oral, anal and light bondage led to Ryan figuring himself out and vowing to do something incredibly nice for every woman he's had sex with this year. Though the list is long, with the help of his friends Ryan aims to achieve this monumental task before Christmas. Will he succeed?

***

I never had a ton of money growing up. I'd never go so far as to say I was poor, because I knew how fortunate I was; between the settlement after Mom died and how hard Dad worked, I led a pretty good life with a nice home in a nice town, but I wasn't one of those kids with a bottomless credit card who could just go around spending money however they wanted without needing to worry about the consequences. I biked around town and didn't beg Dad for a car (well, not often anyway), was almost certainly headed to Regan Hills Community College after graduation, and I knew that if I wanted something I either had to save up for it or wait for my birthday or Christmas.

When I came up with my plan to spread holiday season joy to the admittedly long list of women I'd had sex with since senior year began, I knew that I'd be running through my meager savings in a hurry if I didn't get creative.

Thankfully, I was more than happy to get creative if it meant more moments like getting thrown shirtless against the wall of 18-year-old Izzy Barnes' bedroom.

"You're not much to look at, but if you're half as good as the stories I've heard, I don't give a shit," Izzy said, licking her lips, painted to match the bright blue of her choppy, short hair. At 5'2" and fairly petite, she was a tiny girl with a round, pretty face with bright blue-rimmed glasses, multiple piercings in her ears and a small black stud in her nose. Her tight "Glory to Arstotzka" t-shirt was cut high enough to show off her modest B-cup tits well and enough of her toned abs to reveal her belly button ring, while the long flowing skirt she wore was a colorful mess of bright and clashing fabric patches I was pretty sure she made on her own. Considering it matched the wild collage of game posters and toys on the shelves that lined her room, it fit her.

I'd have said something witty in response, but with the wind nearly knocked from me for how hard she threw me, words were hard to come by. Thankfully, Izzy Barnes was someone who was never at a loss for words.

"I mean, it's not like your ugly or anything like half the guys I pwn after they send me dick pics thinkin' that just 'cause I'm a girl and I game that I wanna see their fleshy bits, everyone says you're a good guy inside and that's a pretty sweet and fucking rare thing these days when you got a lot of guys spouting a lot of vile shit just 'cause it's the only way they can get attention, and you're not like half bad on the outside if in a boring kind of way, but you almost got some abs there which I heard are from a cheerleader? Forget which one with all the rumors flying around out there, but, you know, could be fun," Izzy said, almost so quickly I couldn't catch everything she said.

To say I didn't know Izzy Barnes very well was an understatement. Though we traveled in similar circles around Regan Hills High School, I mostly knew her from the number of multiplayer games she relished killing Tori and me and pretty much anyone else she could find from Regan Hills in. Going to her for this favor was one that felt like a long shot at first, but that her screen name was 69golden_hand69 told me it was one worth taking. I asked around with the girls who'd said they'd help me with my mad December plan if any of them could connect me with Izzy, and found help from one of the people I'd least expected: Brooke King.

I knew that she'd been spending a lot of time hanging out with (and probably fucking) nerds lately, but that she'd gotten in good enough with Izzy Barnes to make this kind of introduction, well, that took me by surprise.

It probably explained Izzy's energy as she ran her hands over me, pulling my head down so we made out furiously.

"Can you tell I like fun?" Izzy continued, smiling up at me sweetly. Before I could answer, she was making out with me again, pressing me against the wall as her hands found my pants.

"I-"

"Yeah, fuck, you got a nice package there, let's see if it's as awesome as what I keep hearing about. I got my doubts, but what I'm feelin' here, my doubts may need to suck it," Izzy said, rubbing her hand up and down my jeans-clad cock before dropping to her knees in front of me. Her tiny, nimble hands quickly undid my belt and zipper with impressive speed, pulling my pants and underwear down around my ankles. She was so close that my cock in all of its thick, ten-inch glory almost bopped her on the cheek as it sprung out, an act that actually made her giggle.

"Oh, this is going to be fucking sweeeeeeeeet!" she said, darting her tongue from between her bright blue lips and licking the head before nearly attacking my cock as she took it between her lips.

Now while I can't adequately explain just what Izzy did with her mouth for how rapid she was moving, I can say that it felt fucking amazing. The way she sucked, swirled her tongue and just took almost my entire length with each stroke was something close to awe inspiring. Watching my massive cock stretching her tiny little lips to the max as she bobbed up and down with near blinding speed, I had to put my hands on her head just so I could slow her down enough to savor the sight of her enthusiastic blowjob.

I'd long thought that Brooke was my most energetic sex partner, but if Izzy kept up like this she may have given Brooke a run for her money.

"Okay, I love a blowjob, you love a blowjob, everybody loves a good blowjob but I'm not here for a fucking blowjob, am I? No, the answer's no, the blowjob's just to warm you up, not that it looks like you need much warming up (thank god, better than most guys I know), but you never know if you're gonna need some warming up and, where was I... right, sex!" Izzy exclaimed as she let my cock go, standing up in front of me so quickly I'd have thought she'd glitched into existence.

Izzy pressed me back against the wall with one last powerful kiss before letting me go, darting over toward her bed. She pulled her shirt off with one practiced movement, as quick and purposeful as anything else she did but miraculously avoiding pulling off her glasses with the violent movement. Her firm tits popped free, both of them centered with a nice, silver dollar sized nipple so erect they just begged to be sucked on.

"You like my titties? I know I don't stack up well next to a lot of other girls at school who seem to be on some weird sort of growth hormones that make like half the student body way above the national average, boy are they gonna have fun later in life when their lower backs give out on them, but-"

"They're beautiful," I said, stepping close to her.

Izzy laughed. I was pretty sure that was a good thing. "Beautiful! Beautiful he says! A three syllable word, that officially makes you better than any guy who's ever asked to see my tits on Twitch. I don't show 'em to them, by the way, gotta romance me a little first or come with high recommendations (which has served me well with some seriously nice cock and pussy out there), and let me tell you you come with high recommendations and I've got it on good authority you ain't half bad at the romancing thing. I don't have a whole lotta time for romancing right now, got a quick tourney in a few with some asswipes who don't think a girl can take 'em down, but if you wanna romance my pussy a bit with your face before we get started with that cock, I won't say no."

"You have heard how much I like eating pussy, right?" I challenged, stepping out of my pants so I was now fully naked before her.

Izzy smiled. "Oh I've heard, but it's best not to assume what with that whole ass of you and... you know what, we all know the assume phrase, don't gotta get hung up on the clichés more than we need to."

With that, she hooked her thumbs into the elastic of her skirt, pulling it down to reveal two things that I'd already assumed to be fairly likely.

First, that much like her opinion on bras, Izzy Barnes also didn't wear panties.

Second, that the patch of hair above her pussy was also dyed bright blue. That couldn't have been comfortable, but it fit her entirely.

Now clad only in knee high red and white striped socks that she made no moves to take off, Izzy twirled around daintily on her feet, sticking her nice, round little ass out at me.

"Like my butt?" Izzy asked, looking over her shoulder at me. She reached one hand back, smacking it playfully, before reaching back with both hands, parting her cheeks slightly. "I know I don't have the greatest boobs in town, but I've always been proud of my butt. It's nice and round and smackable. You can smack it too if you want..."

I sidled up behind her, resting my cock in the valley of her ass cheeks. Reaching around so I could cup her breasts with one hand and finger her pussy with my other, I looked down at Izzy and planted a hot, heavy kiss on her lips.

"While it's definitely smackable, I think there's a lot better things we can do with that ass than just smacking it, don't you?" I whispered, my voice low and promising.

Izzy smirked up at me. "Fucking romantic, I knew it. Come on, let's get on the bed so you can eat my fucking pussy before you fuck me, got it?"

"Yes ma'am," I said as she bounced on over to her bed. I had to admit, she was very right about her ass being smackable, and as she darted onto the bed I couldn't help but swat her one playfully.

Izzy squealed delightedly as she went from being on all fours to rolling on her back, spreading first her legs, then her pussy lips as her fingers worked her soaked little pussy furiously. "Now that's what I'm talking about! Fuck, you might just be a winner after all! Come on and get up here and let's see if you're all you're cracked up to be."

I licked my lips as I eyed her wet, pink little pussy with the blue thatch of pubic hair pointing down at her pussy.

"Well, I've always been one to go for the high score," I said, putting some exceptional cockiness in my voice I thought she'd like.

Izzy rolled her eyes at me. "Gaming sexy talk, yeah, big no no."

"Sorry."

"Don't say sorry, you couldn't have known since we don't know each other all that much anyway and we probably won't get to know each other with what we're gonna do next but maybe a bit more after, I just don't like mixing business and pleasure any more than I have to, and I'm not so high on retro-gaming anyway, so, big no no all around, but all is forgiven, get over here and fuck me with your face already, I got a schedule to keep and I'd like to cum at least twice before we're done here since I'm pretty sure you're good for it," Izzy said, not losing pace with her fingering for even a second. She moaned softly, looking up at me so invitingly and silently for the first time since we'd really started talking this afternoon.

With her pussy looking so delicious, how could I say anything but, "No problem."

I dove in with a vigor that I thought Izzy would appreciate, licking and sucking on her almost unbearably sweet pussy, fucking her energetically with two fingers while I focused much of my attention on her clit. By the way she cooed and squealed, cupping her breasts and pinching her nipples, I knew that this was an approach she definitely enjoyed.

"Oh god yes, fuck me with your face, right there, like that, like that, okay, you're exactly as advertised. I've had people lie to me and oversell shit and guys who say they'll eat you out really good and then all they'll do is just lick you a coupla times, ask if that's enough and then stick their cock in, but you , I can already tell you love yourself some pussy. Eaten a lot of cunt, haven't you?" Izzy asked.

With false modesty in my voice, I said, "I've been known to partake every so often."

"Ha!" Izzy spat back as I went back to work on her pussy. "Every so often would have you still fumbling around and I don't take you for that much of a prodigy, and don't even get on about your AP classes, right there, fuck, that's nice, god, keep going, no, you don't get to boast of being a prodigy, you got experience and experience is a fucking epic thing, I'd take someone who's been around the block and truly leveled up (and yes I know I used a gaming euphemism, do as I say, not as I do and all that) and knows what they're doing over some fumbling amateur any day, and, and..."

Her words began to flee her as I kept eating her out. I could tell that she wanted to keep talking, and I knew that it was a minor miracle to get her to shut up like this. Don't get me wrong, I enjoyed her running commentary, but if I was taking her words from her it meant I was doing something right. Her body tensing, her skin covered in goosebumps, her sentences became scattered words, her scattered words soon becoming vague, primal sounds interspersed with the occasional word.

"Good... fuck... there... you got it... there... fuck... fuck... close... close...closecloseFUCKI'MCUMMING!!CUMMING!! FUUUUUUUUUUUUUCK YEEEEEEEAH MOTHERFUCKER!!" Izzy cried out as her thighs tightened around my face and an impressive flow of liquid spurted from her. I did my best to lap all of it up, but with a flow as heavy as hers my face was soaked in no time.

Giggling and squealing with glee as I did my best to help her come down properly from her orgasm, Izzy cooed appreciatively, running her hands through my hair.

"THAT is EXACTLY what I wanted, thank you so fucking much, you don't even know it, fuck, sorry, I squirt pretty badly sometimes when I cum, that's not a problem, is it? Doesn't look like a problem. I mean, you clearly picked up a lot of XP with the whole eating pussy thing, you've probably met some squirters before, but, still, sorry, and thanks, fuck that was nice!" Izzy exclaimed enthusiastically (though I was growing certain that she didn't have a tone that wasn't enthusiastic), pulling me up on top of her and kissing me repeatedly.

"Okay, so, that was fun, lots and lots and lots of fun, but we both know what you really came here for, right?" Izzy said, stroking my cock and pointing it at her pussy.

"Well, you're gonna be the one doing me the favor, so I'm really here to do whatever I can to please you, but, yes, I was hoping sex was on the table," I said.

"Oh, it's more than on the table..." Izzy replied, pressing the head of my cock against her pussy lips, then arching her hips so it pressed inside of her. "...it's in me! Also, holy fuck that's big!"

"I get that a lot," I grunted, pressing several more inches inside of her.

"Oh, I better be getting a lot of that too, fuck, I can't tell you, god, how long I've been looking for a nice big cock that won't treat me like shit for being a girl who likes video games, keep going, keep going!" Izzy declared, biting her lip and urging me forward, burying slightly more than half of my cock now inside of her.

"I'm going!" I said, sliding slightly more into her.

"What're you taking your time for, I'm not made of fucking tissue paper! I want you to fuck me now fucking fuck me!" Izzy urged.

With one final thrust, I buried the last of my ten inches inside of her. Her eyes went wide, her mouth dropped open in shock, and she howled a beautiful, animalistic roar of surprise and pleasure as my balls rested against her ass. I've said it before and I'll say it again, but this has always been a favorite moment of mine, that brief moment after I've buried my cock in a woman and she understands the full magnitude of what she's taken on. There's always that brief moment of shock, but then the pleasure kicks in where she smiles and is truly looking forward to fucking what I have to offer.

That this moment was one of the few things in the world that could quiet Izzy Barnes for even a moment made me feel nothing but pride. Being that she was Izzy Barnes it didn't last long, especially when she wrapped her legs around my ass and pulled me in closer, but it was one I meant to savor as I really started to fuck her.

"Oh god, yes, fuck, fuck, keep fucking me, like that, you know what to do and you're doing it, fuck, fuck, fuck, Brooke was right, I didn't want to believe it, I couldn't believe it, but Brooke was right, how can she be right about anything, fuck!" Izzy moaned while I pounded her.

"She's smarter than she looks. Smarter than anyone knows," I said.

"She'd have to be to know this, to know you, to make sure everybody knows, FUCK!" Izzy squealed. My hips were a blur by this point, my breath ragged as I fucked her as hard as I could. I knew we were on a timer, but I was pretty sure sex with Izzy would have been this frantic even if we had a full day ahead of us.

I was beginning to lose my breath after a few minutes of this, but thankfully Izzy had enough breath for both of us. Hell, she might have had breath enough for five or six of us and even Brooke to spare. She rolled me over so that she could ride me, sitting fully on top of my cock as she bounced up and down. It never ceased to amaze me how many tiny girls could take so much cock, nor did watching my entire length disappear into those stretched out pussy lips.

"You like the show, don't you? You look like a guy who likes to watch a good show, and lucky for you, I like to put on a good show. I like an audience almost as much as I like talking and you can tell how much I like talking, so tell me, all honesty, how do you like the show?" Izzy asked as she bounced in my lap. As she was also furiously rubbing her clit with one hand and squeezing her right nipple with her other, I could think of only one good answer.

I grabbed her hips and helped her slam down onto my cock. "You put on a great fucking show."

"I know it," she said arrogantly, not stopping her bouncing.

Between the physicality of our union and how fucking great her pussy was feeling, I was getting pretty fucking close.