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Senior Year Memories Ch. 30

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A cheerleader, a girlfriend, a new face & a new status quo.
27.6k words
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124.4k
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Part 32 of the 48 part series

Updated 02/09/2024
Created 04/18/2018
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(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 know it's been a while, but I wanted to thank you for your patience while I dealt with some necessary issues while battling my writing burnout. I hope this chapter proves worth the wait. On top of everything else, I want to give special thanks to fellow Literotica author and SYM reader Lil_kitty for many excellent ideas and acting as a second set of eyes on this chapter, for letting me know what did and didn't work and that I wasn't completely crazy for how long this chapter turned out to be. Thank you very much!)

Previously, on Senior Year Memories: The first week back after winter break has been busy for 18-year-old Ryan Collins, from a quickie in the library with slutty library aide Marie Halpern, to the curious affections of many of the school's female teachers, and the challenges of balancing tutoring three of his classmates. Much of this came to a head at the offices of the school's newspaper, when Ryan chatted up beautiful and kind assistant editor Nica Dubois. Though their conversation started with working on Ryan's articles, it soon progressed to hot sex in the dark room, where Ryan was happy to help Nica face some of her demons about sex. Returning home, Ryan was surprised to find bubbly blonde cheerleader Brooke King waiting for him, and even more surprised that she was there to profess her love for him, made more complicated by Ryan's love for her and for his absent girlfriend, Josie Wong. With an uncertain future, Ryan has much to consider.

***

What do you do when someone tells you they're in love with you?

Well, in the ideal event that they're someone you want to be in love with you, you tell them you love them back, cheer, and reap all the rewards that come with having someone you love love you back.

If it's someone you'd rather steer clear of, then let them down however you can and get as far away as you can before things get any worse.

These are the kinds of situations our parents tell us about, the ones movies and songs and epic poems are written about. They don't tell you what to do when someone tells you they love you when you're in love with someone else, especially when you love them too.

This is why I had trouble sleeping the night after Brooke King told me she loved me. The blonde cheerleader with the ever-present pigtails, a love for the color pink and one of the freakiest minds I ever knew when it came to sex had slowly become my best friend over the past few months, and my feelings for her had only gotten more confused as the year went on. Before this year, Brooke was one of those people I'd just never talked to, we were just so different, but with this being the year of one thing leading to another, this was where I was stuck.

I loved Brooke, that much was clear. I also loved Josie Wong, my beautiful and equally dirty goth girlfriend. I hadn't seen her for weeks since she left with the rest of her family to visit her sick grandmother in Hawaii, and maybe that had weakened my resolve, made it more possible for me to follow up on bad instincts.

This didn't feel bad, though. That was the fucked-up part of it, I think. Loving Brooke felt every bit as natural as loving Josie, but it was still undeniably a problem.

Lying in bed, wakefulness came upon me slowly as I came to the morning after I found Brooke sitting sorrowfully on my front porch. I had flashes of the night before, of pleasure and melancholy as Brooke and I talked, then had sex, then talked some more, then had more sex before turning in for the night curled up next to each other in bed. I'd hoped that between the two of us that we'd be able to put something resembling a plan together, but this was uncharted territory for both of us.

I tried to focus on the brighter moments of that night, of the way Brooke's face looked when she came while riding me, how utterly tight she felt as I took her from behind, but the reality of what we faced had a way of intruding into the fantasy that there was nothing amiss in our world.

I didn't want to fuck anything up. That was the long and the short of it. I didn't want to fuck anything up, but it felt like I had no choice that wouldn't fuck things up for someone. I had this image of teetering on the edge of a cliff, just waiting to go over and lose the best people I'd met this year. I didn't want to do that. I just wanted everybody to be happy, but that just didn't seem to be in the cards, and in a year where I'd already had the fallout of what happened with Rachel and Tori I was not looking forward to another disaster.

Until then, I could still wrap myself in the warm and comforting blanket of denial. Denial, and Brooke in the bed next to me. Just being around her always had a way of lighting up my life in the past, and her being here now was the only thing keeping me from losing my mind.

There was shifting in the bed next to me, enough that I was stirred closer toward consciousness. I rolled over, hoping to wrap an arm around Brooke, but found her side of the bed strangely empty.

"Brooke?" I muttered, wiping the sleep from my eyes.

"Not even close."

That voice snapped my eyes wide open. It was impossible, it had to be a dream, but if it was a dream it was the most vivid dream I'd ever had. I looked around the room, caught her sitting on the edge of the bed. In my waking state, she was a dark angel, dressed from head to toe in a long black coat, with choppy, jet black hair cut back to the same pixie length she had when I first met her and a pale face. Her lips, painted black, curled in an amused smile at me.

Josie.

"You're real," I said in wonderment.

"Uh, last time I checked, yeah, I was real," she said, scooting a little more in my direction.

I sat up and, overjoyed, instantly leaned into her and hugged her tightly. She hugged me back enthusiastically. "Why didn't you tell me you were back?"

"It's called a surprise, and I wanted to drop a big one on you," Josie said, kissing me. Fuck, I'd forgotten how good it felt to kiss her. Part of it felt grim, like I was betraying her by not being completely honest right now, but it felt too good to tell her right now.

"Mission accomplished," I said.

"I thought you'd think so," she replied, smiling. "You know, I've really missed you."

"The feeling's mutual," I said, wanting to keep the conversation flowing. "How's...?"

"Grandmother? Recovering, but well enough that she can take care of herself with the help of her local friends. She's a tough old lady," Josie replied.

"Good," I said, dancing around a subject that was coming into much clearer focus whether I wanted it to or not. I had a hard time meeting her eyes, something she caught on to quickly.

"Brooke's not here," Josie said, her tone cautious. "But she'll be back in a little while."

"She will?" I asked, confused and more than a little frightened.

"My family and I, we got in early, and I came over as soon as I could so you and me could... reconnect. I found Brooke getting ready to go out for a jog, and... well, we got to talking," Josie said.

"Oh?" I asked, feeling as if my heart was beating so hard it might explode. "And what did you talk about?"

"You know, girl stuff, this and that," Josie said. "And about how she loves you, and you love her, and how bad she felt about all of it with you and me."

That was it. That was the sound of the other shoe dropping, the sound of my heart exploding, the sound of everything in my life falling down around me.

Fuck.

I started, "Josie, I can-"

"Ryan, if you tell me 'I can explain', I'll scream. I'm not here asking for an explanation," Josie said, standing up and taking off her long coat. She wore her usual outfit of a dark, tight tank top that showed off her nice round tits, short black skirt, fishnets and boots. Her pale, perfect skin with her slight collection of tattoos and strategic facial and navel piercings was on full display, enough to get me a little hard. If I'd been any less terrified, I might have asked her how she spent a couple weeks in Hawaii without getting a tan, but if anyone knew how to stay consciously pale, it was Josie.

"You're not?" I asked.

"This isn't one of those things that needs... explanation, it needs discussion. Brooke's gone out to grab us some coffee and breakfast, and when she comes back, the three of us need to have a serious talk. I saw that your dad isn't in... should we expect him anytime soon?" Josie asked.

"No," I explained. "He's in San Diego getting some of his dinosaur fossil collection appraised; he'll be out all weekend."

"Good," Josie said simply. "Then the three of us can have a nice, long discussion, like adults, about what happens next. Until then..."

Josie reached down to the hem of her tank top and pulled it up over her head, revealing her bare D-cup tits to me. I knew these breasts well, from the tattoo under her right tit of Chinese characters that said "If you can read this, then you speak Chinese", to her pierced left nipple and its shiny metal bar, and whatever timidity my cock had completely disappeared. It was rock hard in all of its ten-inch-long, very thick glory.

Josie undid her leather skirt and dropped it to the floor, revealing a similarly dark thong. "...we've only got a little while before Brooke comes back, and I want you to fuck the shit out of me before she does, okay?"

I gulped, but I couldn't be tempted away from an offer like that. "Okay."

"Good," she purred, crawling up over me on the bed, kissing me and giving me full access to her body. I ran my hands over her perfect tits, squeezing them, massaging them, running my fingers over her hard, dark nipples and enjoying the way it made her groan. My hands quickly moved on though, finding her round, full ass and latching on, squeezing what I knew to be Josie's favorite part about herself.

"Oh, you've missed that ass, haven't you?" she said, reaching down under the blanket, one of her small, strong hands snaking underneath my underwear and grabbing my cock. "I've missed this, too."

She pulled the blanket back and tore my underwear down in one smooth move, leaving me naked in bed, and her most promisingly in her thong, fishnets and boots almost on top of me.

"Lie down," she commanded. Missing her so badly she could've gotten me to do pretty much anything now, I did as she said. She crawled up on the bed with her knees beside my head and turned around, then straddled my face. Her amazing ass was above me, the only thing between my lips and her mouthwatering asshole a thin strip of fabric.

Reaching back to pull the thong aside, Josie revealed her tight hole to me and said, "Open wide..."

Josie sat down, settling her weight on my face and her asshole on my mouth. Having been in this position plenty before and absolutely loving being back here, I dove in without hesitation. My tongue worshipped her tight hole, licking and sucking, probing inside. Sharing a bed with her like this, even if it was so abrupt and unexpected, was something I couldn't even begin to describe how happy it made me.

"Fucking hell, I've missed this," Josie said, writhing around on my face. I reached around front and began to finger her pussy as she rode my face. She was wet, and I hoped to get my mouth on those lips sooner rather than later, but I knew better than anyone that when Josie set her mind to something, she was going to get it.

"You and me, we've been fucking around like crazy while we had an ocean between us, but it's not the same, is it? You went to an orgy, I got gangbanged, but at the end of the day it's just not the same as being here with each other, is it? We're just two perfect little sluts, made for each other and best when we're together, but better than that, we actually like each other, too. Do you have any idea how hard it is to find a guy you're sexually compatible with when you got a sex drive and imagination like mine, *and* like to hang out with too?" Josie asked me.

I answered her, but the words were probably unintelligible through her ass.

"What was that?" Josie asked, distracted. "Oh, yes, silly me. It's not fair that I talk to you and keep your mouth full, is it? Well, perhaps I should even things up..." Josie said, leaning down and inhaling my cock to the root. Her shift in position brought her dripping pussy to my face, and I dove in with equal fervor.

Now, normally when I'm in the midst of a 69, I always find it to be a slow, intimate act, the kind that brought two people together on a different level than traditional sex as we focused on each other's' pleasure, but this was different. This was frantic, intense, both of us trying to get the other ready for something we didn't fully know, yet. I tongued her clit hard as she sucked me deeper and deeper, her lips and throat heavenly and oh so tight.

Josie took her mouth off my cock and climbed off of my face. She turned around to face me, still kneeling on the bed and looking down at me.

"I've missed you, Ryan. I've missed talking with you, being in the same room with you, your cheesy fucking jokes and the way you're still somehow surprised by all the action you're getting this year, which to be honest stopped being surprising a while ago. I've missed this cock," Josie said, reaching down and wrapping her hand around my throbbing pole. "I've missed feeling you inside of me, and how you could make me feel better than any other guy I've ever been with... but most of all I've missed you."

"I've missed you too, Josie. You don't know how much... no, you do know, don't you?" I asked.

"I do," Josie replied, swinging her leg over me and squatting over my cock. I saw a great internal debate going through her mind as she debated what, precisely, she wanted to do with me, her hand drifting the head of my cock back and forth between her pussy and her ass indecisively. In the end, she decided on pressing my thick head into her pussy lips, groaning loudly as she settled all ten inches deep inside of her sloppy cunt.

"That's what I'm talkin' about," she practically cheered, looking down through the valley of her cleavage at our conjoined genitals. "That... that is perfection."

"None of the guys at the gangbang this big?" I teased.

Josie squeezed me with her pussy. "Most of 'em weren't. One of 'em was close. Another was bigger, I think, but he didn't know how to use it for shit. They were all fun, though."

She began bouncing up and down on my cock, taking much of my cock with each stroke. I'd forgotten how good she felt, and sincerely hoped I'd never forget again, because as ever Josie was absolutely amazing. Tight, hot and so completely enthusiastic, she fucked me as hard as she could without even breaking a sweat, looking down on me with a face masked by lust and love, a sweetness hiding behind a perfectly cultivated dark exterior. If she had a problem with what Brooke had told me, and her, she wasn't letting it show, but if there was a fire hiding in her eye, one that was trying to reestablish a former status quo and remind me of what we'd had before, well I wouldn't have been surprised.

"I'd tease you, ask you if you had any cunts as perfect as mine, but you'd tell me something about how all the girls out there each bring something special to the table and that you just feel grateful to share this experience with them, wouldn't you?" Josie asked.

Honestly, I replied, "Something like that, but if there was such a thing as sexual perfection, your pussy would probably be up there."

"Good non-answer," Josie replied, bouncing even harder. "Motherfucker, fuck I want this, give it to me, fuck me hard! Fuck me harder! Keep fucking me... I haven't cum in days, do it, fuck me, fuck me, make me fucking cum, Ryan, fuck me and make my slutty little cunt cum, fucking... FUCK YEAH, I'M CUMMING, I'M CUMMING ALL OVER YOUR HUGE, FUCKING COCK!!!"

Josie was good to her word, cumming hard on top of me, a gush of juices from her juicy cunt splashing into my pubic hair. She cried out and cursed, sounding more a beast than a beautiful, sweet young woman as she got out some necessary pressure relief on top of me. She kept going, riding it out even past the point where she should have been putty in my hands, her eyes closed tight with pure ecstasy that threatened to set me off inside of her.

When the endorphins finally hit her, she opened her eyes drowsily and looked down at me pleasurably.

"Okay... so it may have been a few days since I've cum," Josie said without any hint of apology. I wouldn't have wanted her any other way.

"I guessed something like that," I replied, smiling and squeezing her tits. She leaned down and kissed me, and I kissed her back. I wrapped my arms around her, holding her close to me while we made out. My cock, still so hard and in desperate need of release, remained buried pleasantly inside of her slick cunt, but I meant to do more than just leave it there.

Gently, I pushed Josie off of me and got up on my knees, grabbing her by the hips and rotating her so she was on her hands and knees. Her pussy and asshole were once again temptingly exposed to me, and though I was torn by my choice, I ultimately decided on the easiest path and buried myself right back in her pussy.

"Awww, I wanted you to fuck my ass," Josie pouted.

"In time," I said, grabbing her hips as I began to fuck her properly. "There... there is time, right?"

"All the time you want. I'm not going anywhere," Josie said.

That comforted me, even if there was something in her tone I couldn't fully read.

While she may have ridden me with a sense of sexual desperation, now that I was behind her it was my turn to do the same. I had missed Josie for the weeks that she was gone, and needed her more than I knew. My hips were a blinding blur as I drove into her, fucking her with everything I had and some of what I didn't have. Her pussy gripped my cock and held me in, which was necessary given the wild pace of my thrusts.

"That's it, that's what I've fucking needed, come on, fuck me, fuck me harder, keep fucking that slutty little cunt until you've filled me up with everything you've got!" Josie wailed, dropping from her hands so she could reach back and finger herself while I fucked her.

I was less eloquent, breathing heavily and grunted as I gave my girlfriend everything I had, fucking her down into my bed as we reached our natural and utterly messy conclusion.

Neither of us could last very long like this. Josie came first, once again, crying out into my mattress as her pussy clamped down on me and set me off. I slowed my pace so I could fill her up, but as I came and came hard, it felt like she'd drained every drop of fluid, every ounce of my being, from my body.

Panting from the exertion, I finally pulled my cock from her sopping cunt, unleashing a small river of juices onto my comforter. I'd have worried about this, but I was more concerned with not falling down on top of Josie. I managed to land just beside her, our faces inches from each other. Her hair and makeup were an utter smeared mess from such an insane fuck, but her smeared lips were smiling with pride.

I returned the smile. "Fuck, I love you."

She leaned over to kiss me. "I love you too. That was... wow."

I laughed. "I may have gone overboard. A little."

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