Senior Year Memories Ch. 35

(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; your support and input really help make this possible, as did your votes ensuring Kaitlyn's appearance and the setting of the main sex scene in this chapter.)

Previously, on Senior Year Memories: It's been a long time coming, but 18-year-old Ryan Collins finally took pretty, soft-spoken art student Jennifer Cage under his wing as his "apprentice." Though hesitant at first, she soon quickly turns into a natural, embracing her sexuality with Ryan's help. After a few good rounds of sex, Ryan invites his girlfriends, Josie Wong and Brooke King, and next-door neighbor, Alice Talbot, over to help Jennifer explore her budding bisexuality, something all the girls are more than happy to embrace. After fielding texts from Kaitlyn and Leah, he continued to embrace the spirit of the lust spell he performed earlier in the month and contacted his friend Sarah Kent, who had last month suggested Ryan hook up with her single mother, Viola Kent.

***

It all started a little over a month ago with four simple words:

"I need your help."

Sarah Kent, a cute, blonde and very shy band geek who I'd watched ascend to confident, fun-loving cheerleader over the course of this year, said these words to me in the midst of an orgy, and given the circumstances and how close we were, I thought there would be no way I could turn her down.

Until I found out that she wanted me to fuck her mother.

I know, I know how it sounds, but it's not as weird as it sounds. Having been raised by a single mother, Sarah and her mom had become best friends, and being the holiday season at the time, she was looking to do something nice for her mother. It was one of those ideas that always seemed just a little crazy to me, but never *too* crazy. It had been in the back of my mind for a while, especially the more I heard about Viola Kent from the other members of her "book club" (actually just an excuse for the moms of town to get drunk and fool around with each other when their husbands couldn't get the job done). Not long ago, I'd also seen Viola for the first time and found her unusually stunning and, well...

I wouldn't have done this if I thought it would threaten my friendship with Sarah, and she had told me she wouldn't have brought it up if she thought it would hurt things between us. This, mathematically, should've been fine.

Nonetheless, that didn't mean it wasn't at least a little weird when Sarah came over one early February morning before school with coffee, donuts, and a need to make a plan.

"So, I'm going to be out for the evening," Sarah said, sitting down at the kitchen table as she munched on a frosting and sprinkle-encrusted donut. "Hanging out and pulling a slumber party with Josie, Mia, Fatima and Hope since it's been for-fucking-ever since the five of us have really spent time together. Should give you plenty of time to work your magic with my mom."

Now, Sarah Kent was someone who I found to be very, very cute, and even with her customary hoodie, jeans and horn-rimmed glasses this morning, I still found her very, very cute. I knew Sarah to be exquisitely flexible and up for pretty much anything when it came to sex, and had enough pictures in my phone's album to prove just how freaky a little slut she could be.

Awkward as it was, though, it was because I was planning this plan to seduce her mother that I found it as difficult to look at Sarah as it was, right now. I mean, I'd fucked a friend's mom before (and fucked said friend, too), and that had led to a pretty brutal period of my life, so it was likely I was just being exceedingly cautious.

"I just need to know... you're sure this is something that you want? I mean, completely and utterly, unreservedly, that if I go through with this, nothing's gonna be fucked up between us, right?" I asked.

Sarah smiled, reaching across the table and touching my hand tenderly. "I'm seriously fine with this, Ryan. I mean it. I love my mom, and she works so hard and doesn't have nearly enough time to have fun and... yeah, I really think you could be something good for her."

Though it didn't make everything better, hearing this did take some of the wind out of my uncertainty. Looking into her bright green eyes, I couldn't help but feel her sincerity and kindness... and, yeah, it was hard not to say yes to pretty much anything she wanted.

"Alright... I just wanted to be sure," I said.

"Thanks," Sarah replied. "And I'm fine with this, really; it was my idea, after all."

"Yeah, but we all have bad ideas we wind up reconsidering, so, I didn't want this to be one of them for you," I said.

"It won't be," Sarah said.

Feeling more confident, especially as the coffee kicked in, I munched on a donut and asked, "So, any intel you can offer me on your mom?"

Sarah grinned, then nodded. "Well, the mom I know and the mom she's been hiding from me are two pretty different people. You've met her, you know she's got the whole *cool mom* vibe going on, and that's not just for you, that's just how she is. She's pretty damn laid-back for someone who works as many jobs and side-hustles as she does, but I know that it's got her pretty damn tired a lot of the time, too. That's the side she shows me."

"And what about the other side?" I asked.

Sarah bit her lip, nervous. "Well... you already know about the sex toy parties she hosts at her book club... and the stripperobics class she teaches. I think... and I don't know this for sure... that my mom used to be a stripper when she was in college."

"Really?" I asked, surprised. It shouldn't have been that surprising, because she was stunning and had the body of a dancer, but it still somehow hit me.

"I'm pretty sure. She's too good at what she does in that pole dancing class without taking any classes to learn how to do it, and it would probably explain why Dad left her for a stripper if he's got a type, so, yeah, I think she's got that in her past. I know she had a lot of fun in her youth, the way she talks about her past, whenever she's willing to talk about her past, but ever since Dad left it's like a switch has flipped. She's always trying to be ultra-responsible in front of me, and I haven't really seen her around guys, though I know she's still interested by the way she looks and... well, I think she could really use some firm, fun, dick," Sarah said.

I grinned, taking another sip of my coffee. "Well, if there's anything I can offer in ample amounts, it is firm, fun, dick."

Sarah shivered in her seat, then focused on her donut when she said, "That's an understatement."

Yeah, if there was ever a time for a cocky smirk, this was it. On any other day, I would have likely done terrible things to Sarah Kent here and now, but given my after-school plans, that didn't feel right.

"So, got any plans for Valentine's Day?" I asked.

"Got a date with Alex from the soccer team," she said. "He's not the smartest, and he's weirdly into talking about his plans to be a crypto investor after high school, but I have it on good authority he's good with his tongue. Not as good as you, but still good, so, should be fun for the day at least."

"Happy to hear it. Valentine's is a good day to get laid, I would think," I said.

"And you?" she asked.

I took a breath. This was a plan I was still hammering out all the details to, and one I had only voiced to Josie and Brooke so far, but it was one I was excited to pull off.

"I've got a lot of invitations from a lot of girls without dates... I'm going to hit up a good number of them on the day of, give my mouth and fingers a serious workout," I said.

"Busy day; lucky it's on a weekend this year," she said, nodding in agreement. "Why only your mouth and fingers?"

"Because I plan on having dinner and some more vigorous fun with another lucky lady, before retiring for the evening with Josie and Brooke," I explained.

"Busy day," Sarah repeated. "But it sounds like you'll have fun. And you're lucky to get to end things with Josie and Brooke. They've both been really excited for their surprise they've got for you."

I raised an eyebrow, questioning. I'd heard some mentions of Josie and Brooke having been working together on a surprise for me, but aside from them getting a motel room nearby for the occasion, I didn't know any serious details about it.

"Do you know anything about this surprise?" I asked.

"Maybe..." Sarah said, playful. "But if I shared, it wouldn't be much of a surprise, would it?"

I grumbled, also a little playful, enough to make her laugh a small, cute laugh.

"You're lucky I've got other plans today..." I said, my voice low and promising.

"And if we want to keep to them, and for you to show my mom a good time, we should probably change the subject, right?" she said, her voice suddenly less playful.

Sarah was right, of course. I straightened myself up and finished my donut, looking in the box she'd brought over for another contender for breakfast.

"True enough," I said.

"Like, we could talk about Jennifer! How have things been going with Jennifer?" Sarah proposed.

I smiled, thinking about the progress I had been making with Jennifer Cage these past days. I didn't know how much was okay for me to share or not, but since I knew Sarah and Jennifer were somewhat familiar with one another, it didn't seem like a bad idea to give some slight details.

I said, "Well, things with Jennifer have been moving along... quite well, I'd say..."

***

Walking through the halls of Regan Hills High at lunchtime with Jennifer Cage by my side brought back a lot of good memories. While before, the curvy art student who favored paint-splattered overalls and a tightly packed ponytail looked like one of the meekest people you'd ever meet, the girl who walked beside me now had a spring in her step and eyes that looked upon the world with a new, horny wonder.

It was a look I knew well, because it had been on my face for much of the last few months. Having a lot of sex in a short period of time after losing your virginity sort of had that effect on you.

"Everyone here... they look different... I'm not crazy, right? There's something different now, isn't there?" Jennifer said as she looked around the boys and girls of our senior class.

"It's pretty cool, right?" I said. "It's one thing to know that everyone else is having sex, but once you become one of them, it's kind of like it unlocks a world where they don't seem so different from you after all. When that realization first hit me, it was like I finally saw what everything was supposed to look like."

"I like it," Jennifer said.

"I'm happy to hear it," I said as we ambled down the hall toward a cluster of drama kids who had gathered around a nearby poster. "I guess the question now comes down to, what do you want to do with it next? Me and Josie and Brooke and Alice are one thing-"

"Oh, you four are a *lot* of things," Jennifer said with a shiver and a grin.

"Fair," I replied. "But, if I've learned anything, while a lot of these situations can fall into your lap with the right connection, you're going to have to *want* them to happen and put yourself in the positions needed to make it happen. Luck can only take you so far; drive, on the other hand, can take you much, much farther."

She licked her lips, nervous. "Brooke offered to introduce me to some of her friends, but I don't know if I'm ready for that yet."

"What kind of friends?" I asked.

"Cheerleaders. Some guys on the football team. I mean, a lot of those guys are hot, and you've done most of the girls on the squad, so you know how hot *they* are, but I don't know if I've got the confidence to go that far yet," Jennifer admitted.

I nodded, understanding. "Alright, one step at a time. Let's try to find someone more your speed..."

I scanned the hallway, looking back toward the group of girls collected by the poster next to the drama room. It advertised that spring musical auditions would be happening quite soon, without saying what exactly that play might be. From my association with Mrs. Harker, the drama teacher, I knew that there was some controversy with the PTA behind the scenes over what musical might be considered "appropriate" for our school, and that the play the students wanted was unlikely to come about.

That, however, was another problem for another time.

"...how about a drama kid?" I asked.

"Aren't they too much drama?" Jennifer asked, jokingly.

"Actually... I haven't had a lot of experience with them," I admitted. "They might be."

"I know some of them, they're not all bad... and there are definitely some cute girls..." Jennifer admitted.

"Like?" I proposed, wanting to get her to talk about her interests.

Nervously, she said, "Well... Chloe Marcus is sweet, in her own way. And really smart, too, when she's not so nervous. I think she might be really cute."

Petite, blonde, Chloe Marcus definitely seemed Jennifer's style. An overachiever and constant worrier with glasses that nearly matched Jennifer's own, I could have easily seen the two of them together. I wouldn't have guessed that Chloe might be one of the drama kids given her intense focus on academics, but, this school offered all sorts of surprises like that.

"Chloe is a start. Who else do you think you could have fun with?" I asked.

Scanning the group, Jennifer returned. "Doreen."

"Doreen Bell..." I said, letting the name roll over my tongue. "An interesting choice."

"Well, *she's* interesting," Jennifer replied.

This was true enough. A shorter, curvier girl and reigning class clown of Regan Hills High, she was more outgoing than someone I would have expected Jennifer to look after. Though there was a similar look between them, they couldn't have been any more different personality-wise, and that was enough of a surprise for me. Nonetheless, Doreen could manage a broad, bright smile that lit up her pretty face, and I saw the potential there.

"Alright, alright, not a bad choice then... let's go one more... who out of everyone there do you think might be the most fun to just get down and dirty with?" I asked, smiling and enjoying the chance to prod her into speaking while getting my first real chance to eye the Drama Club girls myself. There were some definite stunners among them, like tall and leggy Cecilia Dunwich, a black girl with blonde hair that went to her mid-back and a tight ass to kill for, or Faith Serrano, a Latina who was easily one of the bitchiest and flat-out most gorgeous girls in school, and some other less obvious choices like the blonde, athletic and wannabe stuntwoman Amy Temple.

Any of them would have made sense by my eye.

Jennifer, however, had a different eye.

"Olivia," she said, pointing to the pale, dark-haired girl wearing a leather jacket over her hoodie and gray scarf. The student head of our school's stage crew, I knew her to be both a consummate overachiever and a sarcastic asshole who wandered around with an impressive chip on her shoulder. She was smart, and made an impression whenever she was called upon in class, but I never would have looked that hard at her before. I mean, she did have nice eyes, and some very full lips and... okay, I could see where Jennifer was going at a bit of a glance, not that I didn't need confirmation.

"Olivia?" I asked, trying not to sound mean but definitely unable to hide surprise. "Olivia Raine-Goldblum?"

Jennifer nodded. "She's smart. She's funny. She doesn't take shit from anyone, and I've seen her in the showers after gym and, well... she's more physically blessed than you'd expect."

"Huh," I said, giving the disgruntled-looking Olivia another glance. "Good to know."

Jennifer smirked. "I thought you might appreciate the information."

"What I appreciate more is hearing you talk like this," I said, proud. "Good to know you've got some options out there that you can have fun with."

"Looking is one thing. Doing something is something else entirely," Jennifer said.

"One step at a time..." I repeated.

"If you're thinking about trying out for the play, I would highly recommend *against* it."

The soft, lightly sensual voice came from behind us, startling Jennifer. By now, I was getting increasingly used to surprise visitors announcing themselves behind me, so I was reasonably less shocked when we were confronted by 18-year-old senior class president, Sabrina Singh. With a face as stunningly beautiful as hers, with the softest-looking brown skin, pouty lips and big, soulful dark eyes, you would have expected her to be delicate. This would have been a mistake, however. At 5'9", this Indian-American beauty was an utter pitbull, accumulating extracurriculars and inserting herself around school in any way that might improve her chances of getting into a good school. With long black hair tied in a braid that rested over her shoulder and an athletic frame that carried well her large breasts and round ass, she was enticingly imposing, even if she looked tired more often than not. Today she looked particularly haggard, but in her loose, dark skirt and tight red t-shirt that showed off her abs (and belly button piercing), she looked stunning as ever.

"Far be it from me to advise against extracurriculars, naturally," Sabrina explained, pointing to the rolled-up posters under her arm. "But, realistically speaking, if you are not well situated with Mrs. Harker's cult of drama kids, it would be difficult to infiltrate at this point. If you were on the lookout, however, for some clubs that would look good on your college applications, I can recommend a number of organizations around our school that are still looking for members."

She sighed, a look of great exhaustion on her face.

"I'm kind of busy now, but I am interested in joining some clubs... can I give you my number to text you for information?" Jennifer asked, only a trace of her typical meekness in her voice.

I shot her a glance, trying to see I she might have been hitting on Sabrina as our class president took Jennifer's number down, but it looked like she was actually legitimately interested in joining clubs and putting herself out there.

I nodded approvingly, before turning my attention to Sabrina. I knew her well enough to exchange pleasantries in class or the hallway, but hadn't really ever talked to her. Though her beauty was certainly intimidating to a point, I was pretty sure I could hold my own by now.

"I don't really have a lot of free time these days, with the paper and tutoring and all, but thanks for the offer," I said.

"Those are good, but you can always do better if you want to get into a good university. Don't dismiss that out of hand... but the warning about the drama kids certainly still stands," Sabrina stated.

I rubbed a hand through my hair, looking from Sabrina to the students milling around the poster and back. I knew from experience that Mrs. Harker was on the intense side, but running a cult of the drama students?