Caitlins Self Care Weekend Pt 04

"It's nice to meet you, Caitlin," Jess says, smiling at me, "Officially."

My pussy throbs lightly as I think about how less than 12 hours ago, I was listening through the wall as this woman rode her husband to orgasm. While I masturbated. And encouraged her.

"Honestly," I say, "I can't believe this is happening. But I'm glad."

Jess nods, "I know. The odds right?"

A pool service boy, in khakis shorts and a white button up t-shirt, stops at the foot of our chairs. "Room 711?" Jess nods toward the little side table between our chairs. He steps between us and sets down two mimosas, a plate of fries, and a plate of fruit. "Enjoy. Please let us know if there's anything else you need, or anything else we can do to improve your morning."

I snicker to myself hearing those words.

"Thanks. Will do," Jess replies, as the young guy walks away. She turns to look at me, tilting her head curiously, "What's so funny?"

I'm imagining the guy who delivered my breakfast, wondering if his erection has subsided. "God, I should be embarrassed to even tell you this," I say.

"Well have some mimosa, then, to loosen you up" Jess gestures to the table, "you know, since you're very shy." I see her eyebrow raise, teasingly, as she reaches for some grapes and pops them in her mouth.

I laugh again, and sip the drink. Feeling the farthest thing from shy in this woman's presence. Familiarity, yes. Exhilaration, yes. Lust, yes. Shyness, not one bit.

"So that's the second time I've heard that line this morning," I tell her, gesturing to the foot of the chair where the waiter had stood. "I ordered room service this morning, and the young guy who brought it up, might have gotten an eyeful."

"What!" she gasps lightly, her smile lighting up. "Were you naked? What do you mean an eyeful?"

I turn my whole body toward her, leaning a bit. We're gossiping now like we've been friends for ever, "No, I was clothed," I smirk, biting my lip, and pausing for a beat. "But I was a little, I don't know, dazed when he came in. I forgot all my toys, were out all over the bed."

"Oh my god, no!" She giggles, "You're kidding."

"Nope," I shake my head, slowly, for emphasis "All of them."

Her laughter is warm. "What did he do?"

"Got hard," I say, recalling the bulge in his pants, as he stood in my doorway. "Probably hoped this was his MILFy fantasy come true."

Jess's beautiful, big breasts jiggling with her amusement. I like making her laugh. "I'll bet he was," she says, and even under her sunglasses, I can tell she's looking my whole body up and down.

It's 85 degrees, but I get goosebumps.

"Thanks," I reply, feeling my nipples harden even more.

"So," Jess grins, "How many toys exactly, is 'all' your toys?"

"Oh god. A lot. This is my first weekend away from my kid. She just weaned. This is kind of a...self-care weekend? Her dad sent me on it. We aren't together, but he's a good guy. I've been super-stressed. He is so helpful, but she's just needed so much from me. This year has been hard and I, uh..." I trail off, hearing myself starting to ramble.

Jess nods knowingly, "You need mommy time." Her posture softening, turning her body toward me.

"Yeah," I sigh, feeling a little choked up.

"Is she your first?" Jess asks.

"Yes."

"And you aren't with her dad?"

I shake my head, "No. She was not...planned."

Jess lets a slow breathe out from between her lips, and gently say "That's hard. I don't blame you for needing some time. We have two. 5 and 2. It can be hard to get back to feeling like you can take time for yourself." Then, her smirk returning, "I, for one, am very glad this is the weekend you've taken it."

"Oh?" I say, feeling the heaviness in my chest lifting, "And why's that?"

"Well, frankly," she starts, I see her own nipples poking through the stretchy fabric of her crimson suit, "because last night was the hottest sex my husband and I have had in a while. I came harder than I have in years. And I have you to thank."

My pussy throbs as she mentions her orgasms. The ones I listened to her ride her husband to through the wall. The ones I begged for. The ones that sent me over the edge, and made my own desperate pussy cling to my dildo as I came. "Well, you're very welcome."

"I'm serious," she says, "That was the hottest fucking thing he and I have done in a long time. I would never have been as brave as you were to talk through the wall. I though he and I were just gonna fuck after hearing you, and then" she uncrosses, and recrosses her legs, squirming slightly "you were there. Repeating me. And saying things I didn't know he wanted to hear. That I didn't know I wanted to say. The way you begged for him to cum"

"Well, you're welcome." I say. I have to remind myself we are outside in full view of the other hotel guests and staff as she talks, because I have to resist the urge to slide my hand between my legs as I listen to her talk. "I wasn't just begging him to cum though. Hearing you...was amazing. I hope that was clear in my post."

I see her skin flush, a glistening of sweat forming on her chest. She nods. "It seemed like you liked it just as much."

"More," I say, my clit positively throbbing now. I want to reach over and touch her. But something stops me. Maybe because we are in public. Maybe her husband. Maybe I am actually shy. I'm not sure. The heat of the sun and the heat of the conversation getting to me, I stand up. I feel the dampness of sweat and my own wetness between my legs. "I need to cool off," I say, laughing and nodding toward the pool.

"Yeah. Good idea," she stands too. I can't tell if her voice sounds disappointed.

We walk over to the edge, and I let my eyes wander over her body feeling familiarity with her womanly curves. Her thick thighs and plump ass swaying with each step. Her full tits bouncing lightly. We both sat down on the edge of the pool, sliding our legs in.

Then, before my skin can acclimate to the contrast in temperature, I slide in, submerging myself up to my shoulders. The cool water, a pleasurable shock to my whole body. I let my breath out in a hiss. She slides in after me with a little yelp.

"Shit," she laughs, "Nothing like cold water to calm you down."

"No kidding," I respond, but my clit is still throbbing. I lean against the wall, "So, when you realized I had posted...that didn't freak you out?"

"I couldn't fucking believe it," she replies. "I was so revved up, and my husband had passed out. So I was scrolling, because..." she trails off now for a moment, "Because I wanted to cum again. And then, I see that post and I couldn't fucking believe it. I almost snuck out of bed and knocked on your door."

My pussy tightens involuntarily at her words, "why didn't you?"

"It was quiet in your room. I figured you had passed out too."

I shake my head gently, "I was awake."

She scrunches her nose at me, "Then why didn't you reply to my message?"

"You had gotten quiet. I thought you were sleeping."

She shook her head, "I fingered myself for hours thinking about what we did and reading erotic stories."

"Well shit," I laugh, "I spent the night grinding a pillow thinking about it and watching porn."

She leans toward me, "I didn't fall asleep until like 6am."

"Me either!" I exclaim, louder than I meant to.

"Did we just become best friends?!" She asks.

"Yep." I reply.

"Do you want to do karate in the garage?" she continues.

"Yep!" I answer. We are howling with laughter at this point. As we calm, I continued "But actually, I have this weird sense like you and I have been friends for years."

"I know, right!?" she says, bobbing slightly closer to me in the pool. "What is that?"

"I don't know. But I'm not mad." I quiet my voice, "So as my friend, can I tell you something?"

"Anything, friend," she smiles.

"Jess, I am so fucking horny right now. You have me so turned on. And I edged myself all night, but didn't cum. I wanted to wait until after we met. After I saw you. So that the next time I touched myself, I could make myself cum thinking of you." I admit, quietly, but unashamed, "And now that I've met you, all I can think about is how badly you make me want to cum."

Jess's jaw slackens slightly, I see her tongue slip gently between her teeth, before she asks "You masturbated all night, but haven't cum since you heard us fucking?"

I shake my head.

She lets out a little breath, her pink lips slightly parted, "Your clit must be aching?"

I nod.

"You need to cum for me." It isn't a question. She is telling me.

"Fuck," the word slips from my lips.

"You're gonna do it here," she tells me, "In this pool. At least, the first time you cum for me, is gonna be here. After that, we can talk."

If I was ever going to have an orgasm completely untouched, standing here 3 feet from Jess in this pool, was as close as I had ever been. "How?" I ask, looking around at the pool deck that was more populated than it had been when I first walked out.

"Come here," she says, giving a nod in her direction, as she stands at the wall.

I glide through the water, closing the gap between us.

"Feel that?" She asks, grabbing my hand and moving it to the the wall. I feel the pool jet spraying water in steady, firm stream below the surface. "We heard you in the hot tub last night. I know you like this." She trails her hand gently across my covered clit, for just a second. Then places her fingers on the small of my back, and guides my hips to the stream of water, and with a firm pressure of her hand at the top of my ass, she holds me there.

"You're gonna have an orgasm, right here. With all these people around." She tells me, quietly. Her voice conversational and light. Her face, relaxed and friendly, keeping our casual cover. But I can tell, this is not an option. I have no choice in the matter. "So, how long are you staying in this hotel?" she asks, continuing conversation above the water, while her hand directs my hips below, pressing my rigid clit toward the pulsing jet.

"Until Monday," I reply, trying not to moan it. Succeeding, barely, as my clit receives the constant lashing of the pool jet. Gentler than the hot tub, but sufficient.

"Us too. We are here for a work thing for my husband, " she grins, "He'll be in and out. We should definitely hang out. What do you think?" Her hand wanders lower on my ass.

"Definitely," I say, my voice cracking a little as I feel her hand slip between my thighs from behind. I glance around, to see if anyone is watching us.

"We're fine," she says, noticing my gaze. "And even if we aren't, whose gonna stop me? Are you?" She slides the crotch of my swimsuit to the side, and presses her fingers against my pussy lips. The heel of her hand against my puckered little asshole, steadying me against the water jet.

I shake my head, fighting a moan. "I'm so close," I whisper, almost silently.

"Close to what?" she asks, in a bright, unbothered tone. Slipping a finger just past my pussy entrance.

I am afraid if I speak any louder, I'll moan obviously. "To cumming," I breathe through gritted teeth.

"Beg your pardon?" She smirks, slipping a second finger inside me, making me shudder involuntarily, "I didn't catch that."

I am on the thinnest, closest edge to orgasm. A closer edge than I have ever brought myself. Because I can't just let go. I can't just let my body take over without it becoming obscenely obvious to everyone on that pool deck that I am being fingerfucked to mind-blowing pleasure right there.

Jess knows it.

"You are what?" she repeats. An edge to her voice.

"So close to cumming," I whimper, holding myself absolutely still as the water pummels my clit and her fingers start fucking me more firmly under the water.

"So close to cumming for who?" she prompts. I see an eyebrow arch slightly behind her sungalsses.

I let each word out, controlling it's exit over my lips as best I can to maintain discretion. "For you."

She pulls me back from the jet by my cunt, lifting me slightly as she does, the buoyancy of my body in the water unweighting my feet for a second "For who, Caitlin?" Pushing a third finger into me. "What are you doing? And for who?"

I want to shove my hips forward to feel the sweet pleasure of the jet on my clit, but I know she'll just stop me if don't answer her. I take a deep breathe, and in the most controlled voice I can muster, "I am so close to cumming," I exhale, "For you, Jess. I need to cum for you."

"Good girl," she grins, and she slips a fourth finger into me and starts pumping my desperate pussy at a relentless pace. She pushes me back to the jet. The stream once again battering my rigid clit, electrifying my whole cunt. My abs contracting and I buck my hips on her hand involuntarily. I hold my breath. Because if I let even a gasp of air out I'm going to moan loudly. Jess feels my pussy clenching, and she fucks me hard with her fingers. Lifting me onto my tiptoes and tipping me into the side of the pool. I grip the ledge, riding her hand. Pleasure radiating from my cunt. "What's happening, Caitlin?" she asks, casually.

I can't say anything. As pleasure rips through me, I open my mouth but nothing comes out. As I ride her hand to waves of pleasure. She fucks me harder with her hand, "Are you okay? Caitlin?"

"I'm good." I croak. My orgasm, slowing. An older couple a few deck chair down seems to be paying attention to us now. I nod my head in their direction. I am trying to regain composure. Her fingers slowing too. But she is not trying to help me.

"Are you sure?" She says, feigning concern, as she slips her thumb over my clit, pressing it firmly. Jolting me. "You think you got a little overheated? Do we need to back to the room? I think we should."

"I don't think I can walk just yet," I am panting lightly. My legs tingling with the intensity of my post-orgasmic glow. "I need a minute."

She pulls her fingers from my cunt, and splashes a little of the cool water on the back of my neck. "Okay. But I think we should go upstairs so you can lie down," she's says, loud enough for the older couple to hear. And then, whispered just for me, "so I can sit on your face."

Somehow I found the strength to get out of the pool.