Senior Year Memories Ch. 40

Never being one to turn down a cunt as immaculate and tasty as hers, I licked my lips and exclaimed, "Sure!"

With an awkward over-eagerness, I climbed onto the bed between her legs and leaned down until her pussy lips were only a few inches away from my face. I took a moment to enjoy this, looking at the beautiful perfection of her sex, already wet and waiting for me. A slight sniff, and her scent flooded my body, intoxicating me and driving me mad.

Yes, I was overeager, but how couldn't I be under the circumstances?

I dove in, licking her pussy energetically as she soon wrapped her legs around my shoulders, moaning while she ran her fingers through my hair. I'd become rather proud of my oral skills over this past year, and seeing a woman as experienced as Viola responding so well had me quite proud of myself.

"Mmmm, yeeeeeeesssss..." she purred, rocking her hips against my face eagerly. "This is what I need, Ryan... yes, I could use you here all the time, at my beck and call... but then I would be denying so many other needy women your services, and that would just be a crime, wouldn't it?"

I was too occupied to really answer her, suckling gently on her clit before running my tongue over her folds, but if this bothered Viola, she didn't let me know. Instead, I looked up into her eyes and redoubled my efforts.

"My thoughts exactly," she continued, grinning down at me. "But before I completely lose myself, there is something... oh god, right there, yes... fuck... there is something I need to talk to you about... so if you can slow down very, very slightly... no, not that slow... yes, that's it... yes, good, we can talk about this..."

Viola wasn't talking, yet, as she slowly ran her fingertips up and down her body, moaning all the while, especially when she began to squeeze her nipples. Soon her eyes lidded over, and she shivered softly, but when she opened them to look down at me again, I could see a new resolve cross her face.

"I need to get this out before something else does..." Viola laughed, squeezing my head gently with her thighs as she continued rocking against my face. "You know by now the truth of what goes on at the book club meetings I host..."

I nodded, slightly, without stopping my efforts at pleasing her. I knew that Viola Kent held "book club" meetings for the lonely women in Regan Hills, and that a number of my teachers and friend's mothers were a part of it. I also knew that very little reading was actually involved, and that it was more an opportunity for Viola to engage in her side hustle of selling sex toys to the sex-starved MILFs of town, and that they would often just use these meetings to play with each other. It had been something I had dreamed of attending for some time, as it sounded like an erotic experience of legendary proportions, but had never expected to actually attend for how secretive these women were about this.

"...and I also understand that you have a three-day weekend coming up this weekend..." she continued, moaning lowly as I pressed my tongue inside of her.

This was also true. It wasn't a major holiday or anything, just one of those many random days off they called "Staff Development Days", or something like that. With Josie and Brooke's families having planned some brief trips for the occasion, I was actually light on plans for the weekend, but the way Viola was leading the conversation, I was getting the distinct impression that would be changing very soon. I'd heard some hints about something like this recently, and it sounded like the hints were about to become an enticing reality.

My cock twitched with anticipation.

Viola moaned, running her fingers through my hair again. "Well... every year, we ladies of the book club like to set up a bit of a weekend retreat. Find some rental house some distance away from here where we can relax, soak up the sun, drink wine and... well, I believe your imagination can fill in a lot of the gaps on what kind of activities take place there..."

I stopped eating her out for a moment. I said, "I have a pretty vivid imagination."

"I'm sure you do," Viola purred, before looking down at me sternly. "Did I say you could stop eating me out?"

Properly chastened, I began to lap at her pussy again, much to her enjoyment.

Viola continued. "Well, normally this has been an all-girls sort of event, but with how many of my friends you have charmed, and how many others are absolutely *dying* to meet you, an exception has been made this year. Tell me, Ryan... what would you say to making some memories at our book club retreat this weekend?"

I knew there were probably some good arguments against doing this, but for the life of me, I couldn't think of them. Some of the best memories I'd had this year were with women I knew to be a part of the book club. Viola, Mrs. Lynn, Mrs. McNeil, Mrs. Harker, Mrs. Addams... fuck, they were all some of the hottest women in town, and I'd had sex with all of them. Getting them together, as well as with some women I probably hadn't been together with yet?

How could I say anything, but...

"Of course, I'll come," I said, knowing I was taking a chance by stopping the cunnilingus, but thinking it had to be worth it.

The way Viola smiled down at me, looking more like a giddy schoolgirl than a world-weary mom, dance teacher and semi-retired stripper, told me that this was a gamble that was well worth taking.

"Friday. After school. Pack a bag for a few days. Be ready for one of us to pick you up. Until then, get up here!" she exclaimed, loosening her grip on me and pulling me up by the shoulders until I lay next to her on the bed.

Viola kissed me passionately, licking my juices from her face as she reached down to jack my cock. While I made a move to finger her, she instead pushed my hand away, rolling me onto my back. She swung a leg over me, straddling my hips as she lined her pussy up with my cockhead.

"I was hoping that you'd want to come..." she groaned, sliding my cock into her achingly tight pussy. "And I know I'm not the only one... you're gonna make a lot of us old ladies happy..."

I moaned, probably a little too loud, as she settled down onto me, my cock buried entirely within her pussy. It may have put me at my most vulnerable, but when I was with a woman as confident as Viola Kent, I was hoping I'd be able to impress her, too.

I said, "You're not old... but I know I'm gonna make all of you happy..."

Viola groaned again, starting to ride me properly. "Yeah? You're that sure of yourself?"

"Uh huh..." I grunted, grabbing her hips and encouraging her to bounce on my cock. Her modest tits looked absolutely delectable as they bounced, and I couldn't wait to get my mouth on them.

I couldn't wait to do a lot of things with her, and to her, honestly; Viola just had a way of inspiring herself.

"You talk a big game, but you better be able to deliver," Viola grunted, pinching her nipples and moaning as she rode me harder. "Some of the women I'm inviting... they're major sluts... some of them are major bitches... if you think it's going to be an easy weekend, you're going to find yourself sorely disappointed."

Smiling up at her, I reached behind and squeezed her ass. "I'll manage... somehow, I'll manage... because I always manage..."

"I'm sure you do," she replied, smiling down at me warmly while she continued to vigorously fuck me. "And we'll keep each other nice and distracted, don't you worry... you'll be a star... but we love fucking each other too... you'd like to watch that too, wouldn't you?"

The image of Viola with any number of other MILFs I knew made that an easy answer. "Hell yeah."

Viola smirked. "Oh, I'm going to have to steal some time with you... you're going to be quite popular, and I'm going to want some of my own time with you... but a good threesome can be so fucking fun too, god, it's been a while since I've had one with some real dick."

This moment might well have been perfect, had it not been for the knocking at the door.

"Hey," Josie asked through the door. "I got a quick question. I don't wanna interrupt or anything, but is this a bad time?"

Viola looked down at me, almost as if challenging me to see what I wanted to do. While she was still riding me, she had slowed her pace, curious and playful...

"Come on in, Josie!" I said.

Viola dropped her mouth open in surprise, but didn't feel the need to stop this.

Josie soon opened the door, standing in the doorway. It took a moment for her eyes to get used to the darkened room with its shifting lights, but once they did, a look of pleasant surprise crossed her face. True, she knew what I was doing in here, and she knew that Viola was hotter than hell, but the moment she finally saw the naked mom of one of her oldest friends riding her boyfriend and seeing how painfully and utterly hot she was had a way of taking Josie by some surprise.

"That's, uh... wow," Josie said.

Viola laughed as she fucked me. "Well, thank you, Josie. I do try to keep in shape!"

"It's definitely working for you... I'm going to have to ask for tips for my routine," Josie said, before looking down at me. It was clear I was having the time of my life, and she smirked accordingly.

"So, you had a question?" I asked, keeping a confident tone through my grunts as I continued to fuck into Viola.

"Ah, yeah..." Josie said, still clearly distracted by the sight before her. "The delivery place has options for delivery in 45 minutes or an hour... Sarah wants to know how long you plan on taking so she knows how to plan the order."

"I guess it depends," I said, looking up into Viola's eyes.

"On what?" Josie asked.

I grinned, first at Viola, then at Josie. "On if you want to join us."

Josie looked at us in some level of shock, her full lips once again dropping open. I eyed Viola, wanting to make sure that I hadn't crossed any lines, but the way she smiled and only rode me harder seemed like a good answer.

Looking back toward Sarah's room, Josie called out, "Hey, it wouldn't be weird if I joined them, would it?"

There was a moment of pause and consideration before Sarah called back, "Nope! Go nuts!"

Josie turned her attention back to us, then said, "You better make it an hour, then!"

Sarah called back, "Oka-"

Her voice was cut off as Josie closed the door behind her.

"My, my, my, Josie... I always knew you had such potential," Viola purred as Josie walked over to us.

"And you've always been hot... I know how good Ryan says you are, but how good are you with a woman?" Josie asked, mimicking Viola's own confidence quite well.

"Why don't you take off your clothes and find out?" Viola challenged, never once breaking her stride as she rode me. She smiled the smile of a woman who had just won a great victory, and I had a hard time blaming her.

As Josie took off her tank top and approached Viola, I realized Viola wasn't the only winner in this room.

***

The memories of the debauchery that Viola, Josie and I got up to stayed with me throughout the next day at school, giving me a natural high that made it pretty damn difficult to pay attention in class. This was hardly anything new, but as some focus would be needed for the coming evening, I managed to hype myself into a position where I was ready for D&D night by the time school let out.

Which was handy, since I was absolutely terrible at D&D.

"You can't be *that* bad," April Martel said from the passenger of Tori's car. The pretty, blonde, band geek looked back at me sympathetically, while I wondered what I had done to earn a place on the backseat.

Right, I wasn't Tori's girlfriend.

"I am," I said.

"He really is," Tori McNeil laughed from the driver's seat, taking a turn through one of the many suburban streets of Regan Hills in the search for the Park house. My redheaded, curly-haired best friend didn't offer much sympathy, but it was in enough good humor that I decided not to poke her while she was driving.

"We've only tried a few times," Tori continued. "And no matter how much I hold his hand, he always finds the most unique ways of fucking things up. It's impressive, really."

"Well..." April said, sympathetic to my cause. "There'll be a lot of us here, this time, and we'll all help. We'll make it so it'll take a lot of work for you to die."

"You can try, but I'm pretty sure you'll fail. I'm pretty good at rolling natural 1's at the worst possible time," I said.

"Like the time you broke your back while trying to pick up a peanut?" Tori said.

I grumbled. "Yes, like the time I broke my back trying to pick up a peanut."

"Or that time you somehow set yourself on fire while trying to make a pass at the comely bar maiden?" Tori said.

April looked at me, non-believing. "How'd you do that?"

"I had to reach across the bar to pass her a note," I explained, trying to think of various ways I could try to take Tori down with me when my character inevitably died tonight. "I reached across some candles. The note caught fire. I caught fire. Apparently my pleas for help fell upon deaf ears."

"That many natural 1's?" April asked, eyes wide and lips pressed together tightly in an effort to avoid laughing.

"That many," I acknowledged.

Tori said, "Or what about that time with the gelatinous cubes when you-"

"Okay, I get the picture," April said, putting me out of my misery. "He's had some bad luck, but with you DMing, I could see how this would happen."

Turning her attention to me, April continued in a calm, sympathetic voice, "While you know Tori here can sometimes get a little carried away with her playful torture, you don't have to worry about that with Rose. She's a really laid-back DM. She knows what she's doing, likes to keep things fun and with a good story... we'll all have a good time, I swear."

She was so utterly earnest that I couldn't help but feel my heart warm.

I turned to Tori. "You've got a damn good girlfriend."

"Tell me about it," Tori replied, grabbing April's hand and kissing it.

"Awww, now I feel special," April replied, any sarcasm she might have tried to her voice thoroughly watered down by the way she was blushing.

Trying not to feel like the third wheel, I did everything I could to disappear into the backseat, but once the lovey dovey was taken out of the air, April was happy to turn her attention back to me and continue selling me on D&D night.

"Alright, what else do you need to know... fair warnings, fair warnings... well, you already know Izzy, right?" April asked.

"I do know Izzy Barnes," I said, smiling with equal parts recognition and a little trepidation. Izzy was a tiny, pale gamer girl with bright blue hair and a way of speaking a mile a minute that made her difficult to understand at times. Even though I knew her to be unbelievably competitive when it came to any matters of gaming, I also knew that she was generally a kind and thoughtful person who really just wanted to make friends.

That she was also kinda crazy in a really hot sort of way didn't hurt her case, either.

"Well, as you might expect, she can get a little Leeroy Jenkins sometimes, which isn't usually very helpful since she prefers to play Rogue," April explained.

"So, we try to keep her distracted as much as possible," Tori followed up, then looking at me in the rearview mirror. "You might have an easier time of that."

"On it," I said. "And what do you guys play?"

"Ranger," April said, pointing to herself, before turning her thumb to Tori. "And Barbarian."

"Why doesn't this surprise me?" I joked, looking to Tori.

"Because you know me so well..." Tori replied, smiling at me brilliantly.

I settled back in my seat, surprisingly nervous for what was otherwise going to be a game night with a lot of people I considered friends.

"Alright... so what should I be, you think?" I asked.

April looked thoughtful. "Well... Katie's playing a Paladin..."

Tori quickly added. "And Leah's coming tonight, too, so we've got Wizard covered."

"Leah's coming?" I asked, again encouraged and a little nervous. Leah Sartori, the beautiful, olive-skinned Wiccan, had helped me kick off February with a bit of a spell meant to encourage lust around Regan Hills. With her helping get this month going, I somehow wasn't surprised that she found a way to appear at its end.

"Yeah," Tori said, catching my eye in the rearview mirror. "I caught her in the Puma Press offices, and she sounded a bit lonely, so I figured, hey, the more the merrier."

Ah. Yeah, okay, this was less magical happenstance and more the mystical powers of Tori McNeil that got Leah to show up tonight. That made a lot more sense.

"So... we could probably use a Bard," April suggested, looking back encouragingly.

From what little I knew of the game, this didn't sound like the worst fit for me.

"Okay, that's cool..." I said, looking for any more tips as Tori just turned onto the last street before we hit our final destination. "...so, I really don't know Katie all that well... and we're gonna be at her house. Anything I should know?"

April bit her lip a little nervously. "Well, she's a little flighty..."

"Yeah, that I know," I said, remembering how easily Katie Park could go off on rambling tangents when I talked with her at Nerd Baseball. She seemed cute and nice enough in a very nerdy sort of way, but definitely sort of hanging around in her own world, even if she was very enthusiastic about living in her own world.

"And a lot of guys have really messed with her before, so she's pretty into the girl power thing when it comes to putting a gathering together. We've told her that we invited you, and she said she was okay with it, but you still might have to convince her that you're a decent guy if she doesn't already know you," April explained.

Crap. I didn't want to make this any harder for anyone involved, and I was only finding out now that my presence might be a serious issue. This wasn't helping my nerves at all.

"You think that'll be a problem?" I asked.

Tori pulled her car over to the curb and set it to park. Then, turning around to me, she said, "You're a good guy, Ryan. Just be the kind of guy pretty much all of us in the room already adore, and you'll be fine."

"Better than fine," April added.

Still feeling nervous and not knowing if it was more about fucking things up in D&D or about pissing off Katie, I said, "Better than fine... I can live with better than fine..."

***

With snacks and gaming paraphernalia in tow, Tori, April and I walked toward the front of the Park's middle-class suburban house. Hands full, Tori pressed the doorbell with her elbow, and not five seconds later, the door swung open to reveal a very excited, and very tiny, presence.

"You guys made it! Yay!" 18-year-old Katie Park cheered enthusiastically, smiling brightly at Tori and April, and perhaps a little more politely toward me. At 5'0", Katie wasn't exactly an intimidating person, with big glasses that were almost as large as her broad, adorable smile and utterly cute face, framed by shimmering, shoulder-length black hair. She wore a flowy, multi-colored skirt that went just past her thighs over a pair of striped knee-high socks, and a dark blue t-shirt that simply read "NX-01" across her chest.

Or, should I say, across her *very* ample chest. For a girl of her size, she had some clearly impressive curves, with a round bubble butt and an impressive set of DD's stretching out her shirt.

Yeah, Katie was that perfect mix of cute and hot as hell that made it very difficult to keep my disobedient cock from making me look like a total perv, especially when I wanted to make a good impression for me and my friends. I knew that Katie could be a little absent-minded, but she was damn smart, I didn't want to do anything that might fuck up this night.