Senior Year Memories Ch. 37

(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 the ongoing plots.)

(Author's Note: As always, I want to give special thanks to fellow Literotica author Lil_kitty for her excellent work as my editor and acting as a second set of eyes on this chapter, and for letting me know what did and didn't work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories. And of course, I also want to thank my wonderful patrons whose votes, among other things, helped block some of the more intensely kinky moments of this chapter; you guys are fantastic, and your support and input really help make putting the series out this regularly possible.)

Previously, on Senior Year Memories: It's Valentine's Day, and 18-year-old nerd Ryan Collins is having a busy time of it. While he has plans to meet up with girlfriends Josie Wong and Brooke King at a motel room by the end of the night for their long-promised Valentine's surprise, he has chosen to spend the better part of the day wandering around town pleasuring women in need. As such, one by one he visits Alice Talbot, Rose Ferris, Jess Garza, Mallory Dourif, Fatima Hassan and Izzy Barnes, and gives them all orgasms. Then, while dropping off an olive branch in the hopes of rekindling his friendship with estranged best friend Tori McNeil, Ryan meets her mother (and his one-time lover), Lauren McNeil, and winds up pleasuring her as well. Heading home for a shower and dinner, Ryan finally entertains and has sex with busty beauty Brianna Roth after months of flirtation. Finally, Ryan made his way toward Josie and Brooke's motel room, only to find his girlfriends absent, and in their place the surprise they promised: Rachel McNeil.

(CONTENT WARNING: This chapter contains a fairly detailed scene involving fisting, so, if that's not your cup of tea, please be warned now instead of giving me shit in the review section later.)

***

When my girlfriends, Josie and Brooke, told me that they had a surprise for me on Valentine's Day, I was curious. When they said it involved them renting a nearby motel room, my interest was definitely piqued. I was genuinely curious about what kind of debauchery they had come up with that would require a venue change like this, especially when we had so many safe places already available to us where we could get up to trouble.

I thought that, hey, maybe they had something particularly kinky in mind, possibly something where a bunch of our friends would gather together for some fun like we had on New Year's Eve. That would have been pretty fucking awesome, though with the evening I'd just had with Brianna, it would certainly take every last bit of energy I had to deal with that kind of orgy.

Never in a million years would I have expected their surprise to involve Rachel McNeil sitting on the motel room bed in only a bright red, silky bra and panty set with neither of my girlfriends in sight.

"I'll take it from your silence that you missed me, which, yay, a girl always loves to see," Rachel said, amused, as she looked me over. "And that your girlfriends are damn good at keeping surprises."

That was putting it lightly.

I meant to say something to Rachel, but the simple sight of her in my presence again was... well, strangely intimidating in a way that silenced me.

Some of this came down to our history.

When we were kids and I was best friends with her little sister, Tori, Rachel had always been a real pain to Tori and me, making our lives hell seemingly just for the fun of it. In time, I'd grown to both fear and hate her. When she left for college, it seemed like a great reprieve, that Tori and I could finally flourish without Rachel's bitchy influence to knock us down.

This all changed this last November, when I'd met an older, freshly expelled from college Rachel who had seriously mellowed. Now 22 and with a promising future in cybersecurity, she had sought out her family in the hopes of making amends for her prior behavior. While her mother, Lauren, was skeptical, Tori was outright hostile toward Rachel's attempts at building new bridges. Normally this would have been something I'd have held Tori's side on completely (especially since we'd been sleeping together at the time), but with Tori recently in a new relationship of her own and unavailable a lot of this time, and Rachel reaching out to whoever was available, the two of us sort of connected.

We became friends, then very good friends, and then, quite memorably, we became more than friends this past Thanksgiving. Sex with her was... well, amazing, and emotional, and something we both knew to be dangerous but didn't give a shit about the consequences of. At least, we didn't give a shit until Tori walked in on us. After that, things kind of exploded (especially after Tori found out that I'd also slept with her mom, Lauren), and Tori's and my friendship went on ice for some time. It seemed the kind of thing that we'd never be able to come back from, but I'd recently had hopes that Tori and I could patch things up.

Rachel, though... even in her self-imposed exile up in Portland, Oregon, she and I stayed friends. We regularly talked (and had cam sex, because we're only human) via Skype, and she had become one of my closest friends and confidants. When there was something in life I needed advice on, Rachel was the person I would go to, the person I knew I could always talk to and give me some "been there, done that" experience to help me through a problem. Our relationship had evolved into something uniquely intense that was difficult to put my finger on, but one I found myself thankful for every day.

So, yeah, seeing her here was a bit of a shock, but one that set my system alight as I drank in the sight of her. At a lean 5'2", she may not have been the most physically impressive person at a glance, but every second you looked at her, she wowed and tantalized.

Maybe it was her general punk aesthetic, with her choppy, short and glossy red hair, her nose ring, or her dark eye makeup and lipstick. Her lively green eyes looked at me seductively through dark eyeliner and shadow, lively underneath her glasses, while her lips curled into an amused smile.

Maybe it was that much of her pale, creamy skin was overtaken by interlocking, elaborate tattoos that covered her upper chest, back, sides and stomach, or the sleeve that took over her entire left arm. Smaller, more random ones dotted her legs and right arm, and it looked like she'd added several new tats since she lived in Portland.

Maybe it was all this... or maybe it was the fact that she was sitting here, unannounced, in a lacy red bra that barely held in her perfect C-cup tits, and a matching thong that looked positively delicious on the hint of her ass that I could see.

Maybe it was a lot of things that set my heart beating rapidly and made movement feel impossible. All I could do was stand there and stare at the gorgeous woman sitting on the bed of this cheap motel room in complete and utter awe of what was happening, looking like a complete and utter mute idiot.

I had always hoped that I would see Rachel McNeil in person again, but didn't expect it to happen anytime soon. She was a busy woman leading her own life, why should I expect to see her in the coming months or years? And here she was, with me... fuck, what was I going to do?

"Ryan? Hello? Have you hit your blue screen of death? Because you look like you've hit your blue screen of death. I know it's a rough place to be, but if you're in the mood to snap out of it, I'd really be happy to catch up with you," Rachel said, smiling, but I could sense the nervousness hiding in her voice behind her playfulness. Was this difficult for her too? How could it be? How could someone as together and confident and beautiful as Rachel McNeil be nervous in front of me?

"Ryan?" she repeated, her voice sharper and sterner in a way that summoned the old Rachel I'd feared, but with enough softness that I could recognize the new Rachel I'd come to know.

As if snapped from a deep hypnosis, I confidently closed the distance between us quickly, wrapping my arm behind her back to pull her in close, before I kissed her passionately on the lips. Unlike the last time we were together, there was no sadness or frustration. There were none of the issues made difficult by family problems that popped up around the holidays, none of the tension of wondering whether or not Tori would find out that I'd had sex with her mother and sister... no, this was just months of buildup, of eagerness and raw, animalistic need all being released at once.

I leaned down over her, and the two of us made out as only two lovers who'd been separated by great time and distance could. She felt exactly like I remembered her, but somehow better, her skin soft and responsive to my touch as she pressed her body to mine, demanding more. She moaned into my lips as we kissed, perhaps one of the most sublime sounds I'd ever heard.

"I did miss you," I confirmed, coming up for air and smiling at her. My breath was already ragged, my heart pounding. Fuck, I never thought it would feel like this for doing as little as we currently had... but here I was, nervous and excited like it was my first time again.

"I knew it," she said smugly, pulling at my shirt until it was over my head and tossed aside. Rachel looked me up and down appreciatively, and was it possible that I saw her mouth drop open in some pleasant surprise?

"You've been working out," Rachel said, running her fingers lightly up my abs and to my chest. My muscles wouldn't have me on the cover of a magazine anytime soon, but with the workouts Brooke and Peter and a handful of my other friends had put me through, I was definitely a lot more impressive than I'd begun this year.

"Yeah. That a problem?" I asked.

"I mean, I always liked skinny guys... but this isn't a bad look for you, not at all, especially if you've been working on your stamina as well," Rachel purred, her deft fingers suddenly working at my belt.

"I have," I replied, confident.

"Fantastic," she replied, eagerly continuing to try to tear my pants off.

Looking down, I found myself not wanting to break the moment but feeling the need to address a matter of practicality. "This... will be a lot easier if I get my shoes and socks off first."

"Do it," Rachel growled, undoing my belt, and just as easily unbuttoning and unzipping my pants.

"I'm doing it, I'm doing it," I said, taking a waddling step back so I could bend over and untie my shoelaces. I'd managed to get my right shoe and sock off okay, which did feel impressive for my eagerness and shaky hands, but the left shoe wasn't behaving. I'd fucked up the knot somehow, or just couldn't manage it with all my shaking, and so ultimately I simply tried ripping it off.

This was a mistake, as in my enthusiasm, I sent myself spilling backwards onto the floor, quite hard. I did, however, get my shoe off, so that was something.

"Holy shit, Ryan!" Rachel half-yelled, half-laughed as I lay on the floor entangled in my own pants.

Kicking them off until I was wearing only my underwear, I leapt to my feet and exclaimed, "Don't worry! I've got it!"

Still laughing, she replied, "Good... but maybe you should get over here before you find some way of killing yourself before we're able to 'catch up.' I'd really rather not answer to your girlfriends for accidentally killing you on Valentine's Day before they had a chance at you."

"That's probably smart," I said, climbing onto the king-sized bed beside her. Rachel slid over to accommodate me, smiling at me with a nervous eagerness that I rather well understood.

I wrapped my arms around her, pulling her close to me and savoring the skin-on-skin contact. I could feel my own flesh breaking out in goosebumps, her pulse quickening as we were physically close for the first time in months.

"So, I gotta ask, because if I don't ask, I know it's just going to be a weird tension between us where one of us is going to wonder if the other will do something, so, I'm just gonna ask now," I said.

"That was a lot of words to say nothing, but, I'm here for it," Rachel replied.

Shaking the nerves off, I said, "Do you wanna just cuddle and talk, first, or do you wanna... you know..."

"Fuck like wild animals let off their chains?" she suggested.

"Yeah, that," I replied, happy that she was the one to put words to it.

Rachel bit her lip gently, then looked away, thoughtful. "You know I love talking with you... and it's not like I haven't had *any* fun over the past few months away, but... I've been thinking about you for a long time, Ryan. I want to catch up and talk with you, I really do, but since I've been thinking about this for a long time, I'm really, really fucking horny, and would like to do something about that before we get to talking, because I don't know if I'll be able to adequately listen and form coherent thoughts that would line up with any human language while I'm thinking about how good that cock will feel buried deep in my pussy."

I let her words marinate for a moment before I responded. "So, we fuck like wild animals off the chain first, then talk?"

"Then fuck like wild animals let off the chain again, yeah, that was definitely my plan. My hope, anyway," Rachel replied, nodding enthusiastically, grinning like the cat that ate the canary.

I found that grin quite delicious to kiss, as the two of us made out with a greater ferocity than before. My hands were on her, her hands were on me, and we went after each other like we were starving because, in many ways, we were. We'd had our cam sex to be sure, and plenty of intense conversations, but to be in the same room as each other with no threat of family bursting in, smelling, tasting, *feeling* each other... it was like we were two addicts for each other who were finally getting their fix.

I can say with some certainty that her hand found my cock first, gripping it and rubbing it through my underwear. I, however, managed to one-up her by quickly sliding my hand under her thin panties, my fingers quickly finding her shaved pussy. She was already quite wet, but I was pretty sure I could do even better as I fingered her outer folds.

"Oh... fuck yeah..." Rachel moaned, kissing me deeply as I still teased her outer sex. "That's the good stuff... that's what I'm talking about..."

"I've only just started touching you," I said back, teasing.

"Yeah," she retorted. "But it's still fucking good, okay?"

"Well, you ain't seen nothing yet," I said, tugging at her panties with my free hand. I couldn't get enough leverage in this position to actually pull them off completely, but Rachel was eager enough that she could easily arch her back and pull her thong from her ass. It pooled around her thighs, and sitting up, I was able to pull it down to her ankles, then tossed it away.

"Fancy underwear today," I mused, looking hungrily down at her full, pink pussy lips. My mouth watered at the sight, taking in her pale, flushed skin, with tattoos only a matter of inches from her sensitive cunt. There was so much I wanted to do with her that I barely knew where to start.

"It's Valentine's Day... if there's any day for me to go glam, it's today... you do like it, right?" Rachel asked.

"I like it off of you," I joked back.

She rolled her eyes. "Pretend I'm a girl who likes wearing pretty things and compliment my somewhat expensive underwear in kind?"

I grinned, reaching down and stroking her now bare pussy lips. "I think they look fucking hot on you."

Rachel shivered from the contact. "Yeah, but you can do so much more without them, I'll grant you that."

"See?" I said, gently rubbing her again. She looked up at me, biting her lip and needy, as I continued stroking her pussy, now quite wet and very hot.

Without breaking eye contact, I pressed my fingertips briefly inside of her steaming folds, rocking them from side to side slightly, before taking them from her steaming cunt. They were slick with her juices, and I brought them to my nose. First, I took a long, lingering sniff, remembering the utterly intoxicating, thoroughly primal smell of Rachel McNeil's pussy. Then, with my fingers now shaking slightly, I sucked her juices from my digits. My eyes lidded over as I once again got to take in her familiar sweetness, enjoying as it overpowered me. My cock stiffened even harder than it already had, my eyes lidded over.

Fuck, she tasted good.

"Shit, you make that look good," Rachel said, toying with the clasp at the front of her bra. Unlatching it, she released her C-cup tits, with her firm, suckable, and bright pink nipples standing out proudly. Grinning at my no doubt dumbstruck reaction as she pulled off her bra and tossed it aside, she reached up to grab her breasts, playing with her nipples.

"I taste that good?" she continued.

"Better," I said, my voice husky with want.

"Good," Rachel replied. "Gimme some."

I smirked, pressing my fingers gently into her folds again. "No problem."

Satisfied that I had acquired enough juices on them, I pulled my fingers from her pussy and brought them to her mouth. Rachel suckled at them, not breaking eye contact with me as she removed every bit of juices from my fingers with her lips and tongue. Her eyes fluttered briefly, and a low, slow moan built in her chest, but she managed to keep staring into my soul as she sucked her juices from me. It was a powerfully erotic sight, something she had to be fully aware of, for when she let my fingers go, she smiled up at me broadly.

"Again," Rachel said in that cool, confident voice she could manage so well.

I did as she asked, fingering more of her juices from her dripping cunt and feeding them into her mouth while she watched me. It was an unusually hot sight, seeing her getting more and more turned on as I simply fed her her own juices, but I had to say, it was getting me hard as hell, too. After already cumming twice today, I felt like I had just been given a day's worth of energy anew at this sight alone.

Rachel clearly saw the effect this was having on me, and unhesitatingly acted on it. She sneaked her nearest hand under the waistband of my underwear and found my cock, wrapping her small hand around it and trailing up to the tip. Once she found the head, her thumb quickly found my precum and spread it around, soon moistening my cock and making it easier for her to jack me.

My moans soon joined hers as we stayed like this, pleasuring each other, teasing slowly without any need or desire to rush. The fevered pitch of our initial meeting had passed, and now it was about making each other feel good.

Of course, a quality handjob like that has a way of bringing the fevered pitch back in no time, and soon, without even being aware of my actions, I found that I was humping up into her hand.

Rachel smiled at me, then spoke in a sickly-sweet tone. "Awww, poor baby, do you need something more for your cock than my little old hand?"

I growled at her in something that was a mix of primal need and annoyance by how much that tone reminded me of how she used to taunt Tori and me back in the day. I knew that she was a better person than that now, but the way she grinned, I could tell she was trying to get a reaction out of me.