Senior Year Memories Ch. 40 – Erotic Couplings – Free Sex Story

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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 the ongoing plots.)

(Author’s Note: For this chapter, I want to thank all the fans who helped vote on and design the star of this chapter, Katie Park, as the newest SYM Girl. 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.)

Previously, on Senior Year Memories: After some initial worries about how it would affect their newfound reconciliation, 18-year-old Ryan Collins joined his best friend, Tori McNeil, on a double date at the local mall. Although there was tension in the air, the two continued to make up well, while Ryan’s girlfriends, Josie Wong and Brooke King, and Tori’s girlfriend, April Martel, got along splendidly. As the date wound down, Brooke called upon Ryan’s help to aid one of her cheerleading friends, Kitty Stein, in helping cheer up her best friend, fellow cheerleader Riley Richardson, who is recovering from a bad breakup around Valentine’s. Ryan is all too eager to help the pair of ultra-petite cheerleaders, first with kindness and then with the power of mind-blowing Sex, as he sees February coming to a close.

***

I know by now that if you’ve read this far, you’d probably think that any time I used the phrase “study group”, what I actually meant was “Sex“, and I’ll admit that that’s not all that far from the truth. A lot of study sessions had broken down into Sex with the girls I was studying with pretty quickly without much of any actual study actually occurring, which, while fun, occasionally had the side effect of threatening my GPA.

With February rolling to a close, and finals coming ever closer, actual study groups were becoming more and more important with every passing day.

Even if not all the people I studied with might not have always agreed.

“This is fucking bullshit!” Mia Roth bemoaned, dropping her science notebook on the floor and angrily rubbing the bridge of her nose. “I’m never gonna get this!”

Four of us lounged around the modest bedroom of Sarah Kent surrounded by books, laptops, tablets and notebooks, with Mia sitting at the foot of the bed with her head in her hands. The busty, tattooed and pink-haired emo musician tried to keep her usual mask of anger intact, but it was impossible not to notice the fear sneaking through too.

This wasn’t the first time I’d seen the pressure of senior year coming to a close getting to someone, and I knew it wouldn’t be the last.

Pushing away from her desk, Sarah swiveled on her chair to face her friend. “Only some of it’s bullshit, and you are gonna get this, Mia… you just gotta breathe. Relax. Take a step back and maybe punch something. Just nothing in here, alright? I like my stuff.”

The sweet, tiny girl with the wavy blonde hair pushed her horn-rimmed glasses up her nose and smiled comfortingly. As with anyone who had Sarah flash such a warm smile at them, Mia was given some ease.

“It just feels like I’m not getting it… like my head is a sponge that’s already full of water, and if I want to put anything new in there, I have to squeeze out whatever else is in there, and that’s what fucking sucks,” Mia bemoaned.

Sprawled out on the bed in her best black tank top and short leather skirt, my beautiful, goth girlfriend, Josie Wong, silently slid over to her friend and began massaging Mia’s shoulders.

“That helping?” Josie asked.

Groaning softly, Mia answered, “It’s not hurting.”

“Good,” Josie replied, looking at me for backup. While I’m sure that she would have probably wanted me there stuffing Mia’s holes as a way of distracting her away from her study despair, I was, at this point anyway, actually trying to find some semblance of keeping it in my pants for the sake of keeping us on task.

I took off my own glasses, rubbing the bridge of my nose briefly before replacing them. “We’ve been going at this hard for a while; maybe it’s time for a study break?”

“Who doesn’t like a good study break?” Sarah said, standing up and stretching, her tight t-shirt riding up her even tighter abs. “Stretch it out, clear the mind for a few minutes, then we can come back and attack these science books like we mean it!”

“I already meant it the first time around,” Mia said miserably, looking up at her friend. “And are you really pulling this cheerleader bull on me?”

“You betcha!” Sarah said, easily kicking up her leg and catching it in a way that she seemed to be doing a standing split.

“I think I might’ve liked you more when you were a morose band geek, before you sold out and became a cheer whore,” Mia said, tilting her head up to show a playful smirk.

Not letting her friend phase her in the slightest, Sarah let her leg down and looked to Josie. “You wouldn’t be the first to say that.”

“Hey, don’t look at me,” Josie said.

Turning my attention to Mia, I asked her, “And who are you calling a sellout? The way I hear-tell it, you’ve been asked to play with the band in the spring musical, and might have already signed on?”

Mia looked to me, a look of worried surprise crossing her face, while Josie and Sarah looked on with greater amusement.

“Reaaaaallllly?” Josie asked, surprise and a need for good-natured teasing bursting from her face. “You’re throwing your lot in with the drama kids?”

“Not yet!” Mia nearly shouted, defensive. “Nothing’s set in stone, yet, because they won’t even know what show they’re doing ’til the last minute… and how the fuck did you find out about that, Ryan?”

I straightened myself up self-importantly. “A good reporter never reveals their sources.”

And by this, I mean that while screwing around with my “apprentice” Jennifer Cage the other day, she shared this (and some other rumors) with me that she’d heard from cheerleader Cleo Price (who Jennifer was also screwing around with), who’d heard it from a guy from the track team she was fucking, who heard it from a guy he was fucking in the drama club.

“You’ll get a chance to play with the band in front of an audience? That’s kind of huge!” Sarah said excitedly, dropping down to the floor to sit next to Mia.

“Like I said,” Mia intoned, dropping her voice to almost a threat. “Nothing’s been set in stone yet. The way things are going, there might not even be a show… I was just asked if I *might* do this, and I didn’t say no, okay?”

“Huh,” Josie asked, turning to look at me. “I know you’ve got your sources in Drama; you know anything about this?”

I licked my lips, not sure if I had to tell everyone that my “source” in Drama was basically Mrs. Wanda Harker, the drama teacher I was fucking, and some rumors I’d heard, but I thought it worth the time to share what I knew.

“From what I’ve heard, Mrs. Harker is set on doing Little Shop of Horrors, but some bitch on the PTA is getting in the way for some bullshit content reasons,” I explained.

“Which bitch?” Mia asked, looking almost threatening.

“Karen Bowman. Kyle’s mom,” I explained, getting an eyeroll from each of the three girls as we considered the familial relations of Regan Hills High School’s former bully supreme, Kyle Bowman.

I’d gotten him expelled and humiliated pretty badly during Homecoming as revenge for when he punched my lights out back in September, and I was beginning to think that, in between her attempts at playing nice with my family by sending over platters of cookies, that she was taking out her anger on the school. She could start proving a problem to a lot of people if her anger over what happened to Kyle didn’t abate anytime soon.

“Well, that explains that, then, doesn’t it?” Sarah replied.

“Anyone going to do anything about that?” Mia asked, aggression creeping back into her voice.

“If you’re talking about running her down with your car, I’d advise against that, since I’m pretty sure that’s illegal,” Josie answered.

“Well, you know how to take all the fucking fun out of fantasizing,” Mia huffed.

“I do what I can,” Josie replied. “Besides, with all the babysitting I’m doing these days, I can’t provide an accomplice or alibi to you like I used to.”

Josie’s after-school job as a Babysitter was a recent development, but with the need to stash some money away for college, I wasn’t going to hold her more limited availability against her. I knew she was surprisingly pretty damn good at it, and that she really enjoyed the money.

Wanting to give her a chance to boast, I asked, “How is all that babysitting going?”

“Not bad,” Josie admitted. “I never thought I’d say it, but I’m pretty good at it. Pay’s alright, depending on the family. Some of the moms are bitches. Some of the dads…”

She didn’t say anything here, but with the mischief I saw in Josie’s smile, I could tell she was having a lot of fun teasing the dads on the side. Maybe more, I hadn’t asked her yet, and figured she’d volunteer something juicy once she had something juicy to share.

Sarah caught it well, grinning. “May we all have so much luck with after-school jobs.”

“I hear that,” Mia answered, smiling properly this time.

Though there was still some tension in the air, it was nice to see everyone on the same page again, nearly happy and, while not exactly thrilled to be studying for what was ahead, we were ready to attempt it together. I may not have been as close to Mia as I was to the other two (even though I did have Sex with her), but I was happy to see her in better spirits. We were all sharing this rough time together, and it was easier to stand as one than having the crushing inevitability of the end of high school knock us all down.

The future was coming for us in a few months. The next day would be the last of February, and school ended in June. Everything was going to be changing very soon, and if we didn’t do everything it took to keep our heads above water, we were almost certainly doomed to drown.

I wasn’t going to drown, and I certainly wasn’t going to let any of them drown. My future may have looked brighter than ever, and I meant to keep it that way, so when it came to my academics, I made sure to keep everything on track. I wasn’t going to make a run at valedictorian or anything like that this year, but I was optimistic that my final report card might see more A’s than ever before, and not just because I was having Sex with a lot of my teachers.

This was not to say, though, that I was losing the present by looking to the future, no. I knew that this year would be over soon, and I meant to savor every moment of it that didn’t involve preparing for the end. I would spend every moment of it that I could making the most of things with the people I cared about.

Spending every Free moment with my girlfriends, Josie and Brooke.

Going on adventures with the many people I’d come to call friends this year.

And nowadays, getting reacquainted with Tori McNeil, a woman I used to call my best friend, and was hoping to be able to do the same again with soon.

Our estrangement after Thanksgiving had been hard on both of us, but having recently sorted out a lot of our issues with each other, we were on the path to being the same friends that we used to be once again. Tori’s girlfriend, April, had even invited me to join the two of them in their semi-regular D&D game, and while I was a pretty lousy player with even worse luck, I was looking forward to the chance of hanging out with Tori and some our mutual friends on a night with absolutely no pressure and only fun on the table.

“You know what I think we need?” Sarah suggested.

“What?” Mia asked.

“Food,” Sarah replied.

“That sounds like a great idea,” Josie replied, stretching out on the bed. “Some food might help clear our heads.”

“Hear, hear,” I agreed, rocking my head from side to side, trying to clear the cobwebs.

We’d been studying for a few hours now, and I was starting to lose my own focus. A bit of a break to mix things up seemed called for.

“Did I hear a call being made for food?” a sultry voice said from the doorway.

I gulped upon hearing it.

Casually, Mia turned toward the door and said, “Hey, Ms. K.”

I looked over as well, and saw a sight that brought a stirring beneath my pants and made me feel very, very warm.

Standing in the doorway was the one and only Ms. Viola Kent. Sarah’s mom, and one of the single hottest people in Regan Hills. A lightly tanned woman in her early 40s with a tight, dancer’s body on a 5’7″ frame, she held her silky black hair up in a tight bun, while her mischievous, soft brown eyes and playful smile lit up a gorgeous face that couldn’t help but force my heart to skip a beat. Her tight, athletic body was on full display in her short t-shirt that couldn’t help but show a fair bit of her toned midriff, while her tight athletic shorts showcased both her long legs and firm Ass.

I knew her to be a fun, friendly and utterly passionate woman, and like the other three women in this room, yes, I had had Sex with her. Only a couple of weeks ago, in this very house, as a matter of fact. At first, it started out as a part of my “bringing joy to those who needed it” quest I had set out on for February, and also because Sarah had asked me to show her somewhat lonely mother a good time in the best way I knew.

Any ulterior motives quickly fell by the wayside, however, as Viola and I had bonded and had what felt undoubtedly like some of the hottest Sex I’d had this year.

Looking her up and down and trying not to drool, I said, “Hello, Viola.”

Josie shot me an amused glance at my clear ogling, but as she turned her eyes to Sarah’s mom, she then looked back at me and nodded approvingly. Josie loved a good look at a Hot woman as much as I did, and even if it was one of her best friend’s moms, I saw the way her eyes lit up in taking a look at Viola too.

Well, this could be interesting.

Viola grinned at me, but didn’t let anything else on. She said, “This study session needs some recharging?”

“Seriously,” Sarah admitted, her eyes darting from her mother to me, grinning slightly with private amusement.

“Why don’t you order some Chinese and put it on my account? Feel Free to go nuts, I might be working up an appetite myself,” Viola said, smirking playfully.

“Really? That good with you guys?” Sarah asked, getting nods from Josie, Mia and me. “That would be great, Mom, thanks.”

“Oh, it’s my pleasure, honestly…” Viola said, shifting her position slightly. I couldn’t help but notice the smooth swelling of her B-cup breasts, and the reasonable certainty that her nipples were poking quite prominently through her t-shirt. Her eyes flashed to me looking at her, and her smirk only became more enticingly proud.

“If you’re all going to be taking a bit of a break, I’d like to borrow Ryan for a few minutes, if that’s fine with you ladies? I need some help in back over a matter that could use a man’s touch…” she continued, sounding perfectly natural and without any ulterior meaning whatsoever.

“SURE!” I exclaimed, probably a little too fast, and making Sarah and Josie giggle slightly. “Uh, if that’s fine with you?”

“Go for it,” Sarah explained, smiling. “Since it looks like we’re taking a bit more than just a short break anyway, why don’t you *help* her out?”

Mia, for her part, looked confused, before darting her eyes from me to Viola. Watching the progression of her face as the parts clicked together, first with an eye roll, then with her mouth dropping open slightly, impressed, was a lot of fun.

“Don’t take too long,” Josie said, watching as Viola turned and slowly walked from the room, and I, with all the coordination of a newborn giraffe, got up on shaky legs and tried to take after her.

“I won’t!” I declared, then looking at the playful look on Viola’s face as she looked over her shoulder, said, “I mean, I might… I don’t know, I guess I gotta see what the ‘man problem’ is!”

I followed behind Viola, looking down at her legs and Ass, watching her bare feet pressing into the carpet, as in the distance I heard Mia say, “Are you fucking serious?”

Soon, we were too far from Sarah’s room to care, as Viola led me to her bedroom.

“I want to thank you again for your assistance… and for stopping by a couple weeks back. The company was… very enjoyable,” Viola said, ushering me inside of her room.

“Oh, it’s no problem, at all… I was glad to help,” I said, turning as I heard the bedroom door click shut behind us.

The room was suddenly darker than the rest of her house, as I recognized the familiar color-changing light that she’d used the last time we were in here. The room changed to shades of red, blue, green and purple, while low music with a good, danceable beat played in the background. I was transported once again to Viola putting on her strip show for me, and the growing pressure in my pants felt very familiar, and very welcome.

Viola looked at me silently for a moment, standing in front of the door and looking like a predator waiting to pounce.

I didn’t give her the chance, closing the distance between us, wrapping an arm around her and pulling her in for a deep, passionate kiss. Our bodies melded into one another, conforming and pressing into each other as we tried to feel every square inch of the other.

“It’s been too long…” Viola groaned, reaching down to feel my cock through my jeans.

“It’s barely been two weeks,” I grunted. “Not that I haven’t wanted this, too.”

“And that is my point exactly… why wait two weeks when we can have it now,” she said, pushing off of me, then walking around over toward her large bed. With little provocation, she reached up and let down her hair, letting it cascade down to her mid-back, before she quickly pulled off her top, then her shorts.

Whereas last time, her getting naked was a slow, teasing process, now she stood deliciously nude before me, ready and waiting. Her firm breasts sat high, her dark brown nipples standing out, while her shaved Pussy looked suitably ready.

Looking at me, Viola put her hands on her hips in mock impatience and said, “Well?”

“Oh, uh… right…” I said, stripping out of my clothes with considerably less grace than her until I too was naked. My thick, ten-inch cock stood at ready attention, eager for her attentions and happy to see how hungrily she eyed me.

“Mmm… so nice…” she said, sitting down on her bed.

Viola lay back, propping her head up on some pillows while she stretched out and spread her legs. She reached between them, fingering and pulling apart her Pussy lips to give me a better look at her moist Sex. This sight had me pretty well useless, staring hypnotized as I saw lewd perfection splayed out before me. Viola could well have commanded me to do anything in this moment, and I would have been helpless to turn her down.

I remembered how her body felt against mine. How she looked while dancing… how she tasted… how she could make me cum like no one else.

Viola looked at me with a very distinct satisfaction, smirking as she continued to slowly pleasure herself.

“There actually is something I need to discuss with you, Ryan… and I want you to eat my Pussy while I do that,” she said, her voice somehow friendly and commanding all at once.

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