The Scholarship Ch. 03 - Escalation

Other than the pool, it appears Ms. Larson has an appreciation for a variety of sports. Without going far I can see a sandy pit with a volleyball net, a croquet course, and a small basketball court. All of this without even counting the acres of wide open green space.

Holy shit.

I'm not much of an outdoorsman, having spent most of my life dedicated to film--whether watching or making--or other less exercise focused activities. That might change though, while I'm here. Most of my schooling now will be focused on film, and I'll need to vary my hobbies to keep myself sane. I've never even seen a croquet set in real life, but it has to be fun, otherwise what the hell have rich people been talking about for so long?

I decide on the pool. It's really the only activity, other than frolicking gaily across the grass, that I can properly engage with on my own. I've never been skinny dipping before, but at this house that's basically all I'll be able to do. Or is it only skinny dipping if you do it at night in a lake while being pressured by your friends?

I test the water first, dipping a foot into it and finding the temperature to be perfect. Of course it is. It's colder than the air, and feels chilly, but I know it's heated and will be wonderful in the long term. Then I jump into the deep end and let the water take me.

Swimming isn't my favorite thing, and I'm not a super strong swimmer, but it's nice and relaxing and the time starts to slip away from me as I drift around the man-made lake that Ms. Larson calls a pool. I float a little, swim a few laps, and then go back to floating and enjoying the cool water on my skin.

"You need to be wearing sunscreen, Joseph." I open my eyes and see Delilah standing on the edge of the pool, holding a bottle of sunscreen up near her massive tits. She's already applied it to herself, if the creamy coating on her body is anything to go by.

"Um, thanks, yeah," I say, rolling over and paddling to the stairs and climbing out of the pool. "I don't normally burn, so I didn't think about it."

She clicks her tongue at me disapprovingly. "If you get a bad sunburn, or worse, Ms. Larson will have my head. So come dry off," she gestures to a towel on one of the lounge chairs, "and sunscreen yourself if you're going to be out here." I don't argue with that. It's the right move, I'm just a dumb idiot sometimes.

Delilah hands me the sunscreen then watches over me like the proctor for an exam, tutting away when I miss a spot. I rub the lotion in and take note of her tuts, though I'm occasionally distracted by her tits. They're like little planets. Each one has its own gravity, drawing me closer. Or maybe I'm just horny and they're big tits.

"Let me help you with your back," Delilah offers. I freeze, thinking about her touching my body and where that might go while we're both naked. But there's no reason to think that she wants to do literally anything other than put sunscreen on my back. If I panic anytime a woman touches me while we're both naked, I'm going to have a very rough time here.

Her hands are soft, dainty, and smaller than I think I had noticed. And warm. She gently massages the muscles on my back while she rubs the lotion into my skin, taking her time and ensuring no part of me goes uncovered. And then she's done, and her hands lifting off of my body leaves me wanting more.

"There you go, all good to go," she says quietly, patting me on the back. "Feel free to enjoy the sun now. SPF 60 has you covered."

"Thanks, Delilah," I say, making my way back to the pool, this time slowly walking back down the stairs.

"Don't mention it, Joe. I wouldn't want your cute little ass to burn to a crisp. Besides, it's my job to help take care of you while you're here."

What an odd juxtaposition of sentences. But I suppose it all makes sense for her. I try to push it out of my mind as I swim around and enjoy the water. It's nice, at least, to know that someone is looking out for my well being. Unless she was lying. Whatever.

As I start swimming again, Delilah stretches out on one of the lounge chairs. She spreads her legs, baring her pussy to me entirely, and her heavy tits shift towards her sides as she leans. I don't know where she kept her sunglasses, but they're suddenly on her face, hiding her eyes from view so I have no idea if she's looking at me or possibly even asleep.

The pool is nice and helps pass the time and focus on nothing but stretching my muscles and relaxing after the workout this morning. It mentally felt like a lifetime had passed since this morning's exercise, but my body felt it acutely. I try not to think about that though. Don't think about Serena, and definitely don't think about Lauren. Try and focus on something else.

I'm not sure how much time has passed of me lazily exploring the enormous pool before I hear something that actually draws my attention and pulls me from my thoughts. It's a moan, quiet and low. Reserved almost, as if the person is trying to keep themselves quiet.

I turn my head and spot her. Hard to miss her, really, she hasn't moved from her chair. Delilah is slowly rubbing her pussy, two fingers casually slipping up and down the outside of her labia. She purses her lips, trying to stifle the moans, but she's clearly enjoying herself if the sounds escaping her are any indication. Delilah's movements are slow and steady, as if she isn't trying to cum yet, just enjoying the feeling of her gentle rubs and caresses. Not the first woman I've watched masturbate today, but this one feels significantly more voyeuristic. Like I'm getting a secret show even she doesn't know about.

Ignoring it would be the smart idea, definitely the way to keep myself out of any weird situations or trouble of any kind. Maybe she'll stop soon anyway. But when a lap around the pool to collect my thoughts doesn't stop me from looking over at her every few seconds, I slow and stop against the side of the pool. I cross my arms and rest my chin on them and just watch her play with herself. Fuck it. She knew I was out here. She clearly didn't care if I watched, or maybe that was the point.

Delilah doesn't penetrate herself with her fingers. Just rubs around her slit, occasionally brushing against her clit and shivering with pleasure at the sensation. My cock very quickly rises at the sight, going from entirely flaccid to pulsing with desire within just a minute of watching Delilah put on a show. Her free hand reaches up to grab one of her massive tits and squeezes it firmly against her chest. Thumb and forefinger ensnare her nipple, pinching and twisting as she works her pussy with her other hand. The moans get louder, growing in intensity with no longer even an attempt to stay quiet.

If there were neighbors, they would surely hear. If there were neighbors, they would definitely be able to look out a window and see this voluptuous blonde pleasuring herself with reckless abandon. But there are no neighbors. It's just me. The show is all for me.

"Can you do me a favor, Joseph?" Delilah asks suddenly. Her head doesn't move but I can sense she's looking at me now. Maybe she always was and my senses are just slow to pick up on that. Now, though, there's no mistaking it.

"Depends on the favor," I respond quietly. I'm in it now; the fourth wall has been broken and it seems unlikely it will be repaired. My role as audience member is dissolving and I'm being dragged into the play.

"You'll like it," she says with a breathy giggle. She shifts in her chair and the hand holding her breast gestures for me to join her. "Just play with my nipples for me. I don't need you to touch my pussy, I don't need you to kiss me, or lick me or any of that shit right now, just come toy with my nipples and help me cum." I can do that. I pull myself up out of the pool, not bothering with the stairs right now. Her tits are marvelous, big massive boobs that I would have killed to play with just a few days ago. Now I don't have to.

"Are you sure?" I ask as I kneel next to her chair. I'm still soaking wet, but she doesn't seem to mind.

"Of course I'm sure. I like having my tits played with but it's more fun if someone else does it. And I'm sure that's not a problem for you." It's not a question, it doesn't have to be. She knows well enough that as a horny teenage boy it would be insane of me to turn down touching any boobs. Especially boobs like these. I nod to her, and reach up, cupping one massive breast in each hand. "Feel free to play and explore for a bit," she tells me, that breathiness back in her voice.

I waste no more time getting my hands up on her chest. Her tits are massive, soft, and perfectly squishy. The flesh folds under the pressure of my hand, and my fingers squish into her. My massaging starts slow and gentle, but within just a few seconds I'm groping her more aggressively. "Mmmmm," she moans, "Ok, that's... you're doing good," she encourages me, "Now go for my nipples. Take them and pinch... pull a little... just don't be too rough."

That makes me pause for a moment. "How... how will I know how rough is too rough?" I ask.

"I'll let you know, it'll be ok, don't worry too much about it." She flashes me a smile, then leans towards me and kisses me briefly. "Felt wrong to have you feel up my tits without ever kissing you," she says quietly. This time I lean in, and my lips find hers once more, our mouths move together as we enjoy the kiss, tongues wrestling for supremacy of the battleground we've created.

She shifts, pushing her tits around in my hands, and my fingers find her nipples. So, of course, I do what I've been asked to do, and pinch each one gently. I roll the nub between my fingers, back and forth, back and forth. Delilah sighs, pulls away from the kiss, and her hands go down to her pussy. Her arms squish her tits together beautifully, making a Venn diagram of breasts.

"Harder," she whispers, "and pull on them." I hesitantly do as she says, and am rewarded by her moans intensifying. My cock throbs, pressing against her side, leaving wet marks on her skin, but that's not an important piece of this puzzle. Maybe I'll cum soon, but for now I get to play with her chest and I'm more than happy with that.

I tug hard on her nipples, making them strain against her breasts. "Yesss," she hisses, "oh yes, good God. Just like that!" She's rubbing herself faster now, hand and wrist shaking as she circles her clit with one hand and the other eagerly pushes two fingers into her pussy. It squelches as she fingers herself, but it's barely audible over the sound of her panting and moaning.

"Twist, Joe!" She cries. I do it, twisting her nipples for her, harder than I would have thought appropriate, but apparently perfect for her. Her cries escalate, piercing the otherwise quiet afternoon day, loud enough that I'm sure anyone in the house can hear her. Maybe she wants that, maybe she doesn't care, or maybe she just doesn't realize how loud she's being.

"Fuck!" She grunts as her fingers work her pussy. "I'm getting close, fuck yes," her voice is tapering out, being replaced by screeches of pure pleasure. I tear my eyes away from her face and her chest and look down at the blur that her hand has become. The inner folds of her pussy are more hidden than Lauren's, Serena's, or Julie's, so I don't have the best view, but her knees bend, pulling her legs up as she gets right up to the edge of her orgasm.

"More," she begs, and I twist slightly more, pulling out on her tits as I do. Delilah screams, half pleasure and half pain, and cums. Her legs shake wildly, spasming around on the chair, and I fall back, dropping her tits and just watching the show as her body is wracked with pleasure. Delilah eventually stops spasming and falls still, even pulling her hand away from her pussy. Her hand is clearly soaked in her juices, drops of her arousal dripping onto her stomach and chest. She is shaking as she raises her hand to her face and slowly licks her fingers clean of her juices.

She doesn't speak or make any noises other than quiet slurping and hard breathing until her fingers are clean enough, per her inspection. Then her head falls back to the chair and she grins at me. "That was nice, thank you..." she pants, "Most people aren't that rough with my tits. But sometimes I need it." She casually massages one breast, as if it needed some aftercare.

"Well uh, you're welcome, I guess," I say with a smile. "But I feel like I should be thanking you, that was a first for me, and I loved it."

"I liked when you were watching, but having you help out was vastly better. And you shouldn't thank me yet," her hand drifts down and she lightly trails her fingers along my erect cock. "You can thank me after I jerk your thick cock off. How does that sound?"

"That sounds amazing," I squeak, and my cock throbs in agreement, twitching against her fingers, "Doing that, and watching you, got me so fucking horny," I state the obvious in my addled state of obscene arousal.

Delilah doesn't respond with words. Words are more effort than she needs. She only needs to wrap her fingers around my shaft and start to slowly stroke me. I'm still kneeling next to her as she begins to pump her hand along my cock. "I'd love to see you cum," she whispers. "Julie said she enjoyed her show. And I do so love watching someone cum for me. Man, woman, whatever they identify as... I like when they cum. Makes me feel good, and wanted. Do you want me, Joseph?" She asks, peering over the top of her sunglasses at me.

"Yes," I gasp, my hips moving on their own, humping into her hand even as she strokes me.

"What do you want to do to me?"

"I want..." I cut off with a gasp.

"You can do anything to me, you know that? Ask anyone here... I never say 'no'. Especially not for a hot cock like this." She pauses and rubs her thumb over my tip, making me shiver.

"I want to fuck your tits and then play with them while you suck me off," I finally get out.

Delilah grins and rolls onto her side, making those heavy tits cascade over each other. Her thick body jiggles alluringly with the movement and she grips my cock with a new angle, stroking me faster. "Is that what you want right now? You want to fuck my big titties? Want to cum in my mouth?" She leans closer, her voice a harsh whisper breaking through the cloud of arousal built up in my brain.

"God, yes," I grunt. I reach up with a hand to boldly fondle one of her boobs. They feel amazing, perfect globes of soft flesh. I want to feel them wrapped around my dick so badly it hurts.

"You don't want to fuck my pussy?" She asks, a hurt tone tiptoeing into her voice. "Don't want me to take your virginity?"

"It's just..." I respond, trying to tactfully answer this while she has her hand on my dick. "It's a lot and--"

"I'm teasing, I don't blame you. This is only your second day, baby. I'm sure we'll find a time for you to fuck me." She kisses me, and I fondle her chest more aggressively while our tongues are locked. She matches my pace with her own hand sliding up and down over my throbbing erection from base to tip.

"Joseph," I hear another voice break through the fog in my brain, "I need you to come inside and talk to me for a bit." I look over to see Ms. Larson standing in the doorway that leads from the house to the back patio. She's wearing a knee length yellow and white sundress, some sandals, and a sunhat. Her red hair is mostly tucked up into the hat, though a few strands fall loose.

Stunning. That's the only word that comes to mind to describe her. Just fucking stunning, all the time. She's more than twice my age and probably the most attractive woman I've ever seen. I have a naked woman actively stroking my dick and the sight of Ms. Larson in a sundress has captured my attention completely.

"Uh. Right now?" I ask. Delilah hasn't stopped or even slowed down, and I'm certainly not going to make her quit. Not when I'm already this far down the path to pleasure. My balls are starting to tense up, my breathing getting heavier.

"Yes, right now." Her head turns just a little to address Delilah. "Drop his cock." Delilah follows the order instantly, her hand doing one last stroke from my patch of pubic hair up past the tip of my dick, and then her hand is gone. She gives me an apologetic look, but then looks away, throwing me to the beautiful wolf.

I slowly push myself up off of my knees, groaning because I had been in that position for so long. "Did I do something wrong?" I ask, turning to face Ms. Larson. My cock points at her like a spear, but I don't feel like a warrior at all. The stern look on her face makes me feel like I've been called into the principal's office and I'm not at all prepared for what's coming.

"You didn't do anything wrong, just come inside and talk to me for a bit." There's a warmth to her voice, but her tone is overall stern, expecting to be obeyed. And I do want to do what she says. That should probably trouble me, at least a little, but it doesn't. Yet amother fact about this new stage of my life.

"Thank you for uh... everything... Delilah," I say, smiling down at her naked body.

"Any time," she says flippantly as I turn to walk away.

I walk to the door and Ms. Larson hands me a towel. "Take your time drying off, don't want you to drip all over the floor like a barbarian," she gives a tinkling little laugh and watches me rub myself down with the towel. I avoid spending too much time on my dick, I'm already extremely stimulated and don't want to either make it worse or accidentally cum in the towel. I'll finish myself off eventually and just hope I don't develop a case of blue balls from this.

When I'm dry I set the towel down and follow Ms. Larson inside. She's quiet, which troubles me only because our conversation was apparently urgent. We wind up in the kitchen and she hands me a glass of water, lightly tinted yellow. "Lemon flavor packet," she explains, "helps with hydration. And you may not feel hot because you've been in the pool, but you're not used to the California heat, and I'm sure you're dehydrated. So drink while we talk, and get more whenever you need."

I nod and take a sip. It's very faintly lemony, like someone messed up making lemonade. "So uh, what are we talking about?" I ask nervously after half my glass is gone. Ms. Larson gestures for me to sit at the island while she leans, facing me, on the other side of it.

"I want to talk about your day," she says simply. And then she's quiet, as if that's enough for me to go on.

"Ok, um. I worked out with you this morning, watched a movie, took a nap, ate lunch, went swimming, and now I'm here." I summarize my day for her and she stares at me blankly.

"Two things, Joseph," she says slowly, "First, you left out a few important, very fun activities. And secondly, I don't care so much what you did as I do how you're feeling about it."

"What do you mean?"

"Don't play dumb," she admonishes me, "this is my house and I know everything that happens here. You fingered Julie while she jerked you off, and just helped Delilah cum like the little pain hungry slut that she is. But I imagine both of those just made you feel good. I'm concerned about the part I didn't mention, that might have made you feel bad."

"You mean uh, my thing with Lauren."

"Precisely. I got home about an hour ago, Julie told me about it, and then I breezed through some of the footage from today. You seemed down, and I was under the impression that you and your sister are inseparable. The closest thing to Siamese twins this side of being physically joined."

"Things were... awkward... afterwards."

"Well obviously," she smiles, "you were masturbating with your sister. I'm sure that's a strange feeling. Not the person you really expect to have first sexual encounters with, right?" I nod in response and drink some more water. "All day you felt like maybe you fucked up? Ruined your relationship in some way? You regretted ever doing it, right?"