Caitlins Self Care Weekend Pt 06

(This is part 6 in a series. The previous installments can be found on my profile.)

"You said you're here until Monday too?" Jess asks me, uncurling her legs from the post-orgasmic fetal position she has been coiled into. Stretching, and then turning onto her side to face me.

I slink down, from my own seated position and lie face her, "Yeah, I don't live far, but yeah I'm in the hotel until Monday. You?" I am lying in her wet spot, and I don't care. Watching her naked body next to me, recovering from the squirting orgasm she just had.

"Yeah, we are here until Monday," she smiles, "We live about 4 hours from here though. This is a working weekend for Rob," she pauses for a second at the mention of her husband, I can't quite read the tone behind it. "And a fun weekend for me."

"Are you having fun?" I ask, glancing toward the soaked sheet underneath my hip.

Jess's steely blue eyes glint, as she looks toward the wet spot, and then back at me, "God, could you imagine if I said I wasn't?"

"I'd be pretty bummed honestly," I tell her, dropping what little guard I have up at this point. Rolling onto my back, taking a deep breath, and then exhaling slowly. "I am really enjoying myself. This is the first time I've felt, I don't know, more than just sexual or horny or whatever since my daughter was born. Like I've had sex since then. I've definitely masturbated since then." I laugh, looking briefly at my toys--some of which have fallen off the bed--then back up at the ceiling.

Jess is quiet, soft and attentive.

"I just haven't felt, desirable? Maybe? I don't know. It's been a year of no sleep, breastfeeding, spit up, and stress. I just feel like a cow and like..." I stop myself, realizing I'm unloading a lot of personal information and that I have probably killed the mood. "Sorry, that's...a lot."

"Hey," Jess reaches toward me, resting her hand on my thigh, giving it a light squeeze. It's reassuring and arousing at the same time. "It's normal. It's hard though, that first year is super hard, and you are desirable."

I turn to my head to look at her. She's smiling softly at me. Her hair is a mess. She's fucking adorable. I smile back at her, reaching to smooth out her mussed up hair. "Thank you," I say, "I feel more confident in that after your, uh, enthusiasm today."

She swats my thigh gently, and pulls away, feigning embarrassment. "Listen," she scolds mockingly, "This was obviously just an average Saturday morning, don't get a big head about it."

"Well damn," I laugh, "if this is how you spend all your Saturday mornings, then we definitely need to be friends because I'd like to hang out on Saturdays." My own clit still achingly unsatisfied, throbbing as I replayed her multiple orgasms in my own mind.

She laughs, standing up--a little wobbly--and walking to the mini fridge to pull out a bottle of water "Is it okay if I take this? I'll bring you one from ours to replace it."

I nod, waving my hand in a go-ahead gesture. Ours. As in hers and her husband's. I'm still horny, but the reality of this woman's life is slowly filtering into my mind. I feel guilty? Nervous? I'm not sure. But I really like Jess, she feels like a friend and I feel like I should check in. "So, your husband is Rob?" I ask, casually, not sure how she'll respond.

She tenses, subtly, and then unscrews the top of the water bottle, taking a sip. "Yes," she glances at the wall for a second then back at me. That tells me what I need to know.

"I take it he didn't know you were going to meet up with me," I say.

She shakes her head, "No."

The ache between my legs lessening, starting to be replaced by a slight pit in my stomach. "I know you said you hadn't been with a woman before, but is you playing with other people something he knows about?"

She lets out a little breathe, moves back to the bed, and sits on the far corner. She inhales sharply, "I never have before...this," she waves her hand gesturing to me and herself and the bed, "I...This...Fuck." Her eyes drop, and I can see anxiety behind them for the first time since we met.

"This just kind of happened," I finish her thought, pulling the sheet up to cover myself. Feeling shyer now, and also wanting to take away the pressure of my own arousal from her, seeing her own thoughts racing behind her eyes. I enjoyed making her cum, but more than that I enjoyed her presence. When we had joked about becoming best friends, to me something about that didn't feel entirely like a joke.

She nods, reaching for the robe I had been wearing last night and pulling it on to cover her own body. "Yeah. Fuck, I'm sorry," she says, tying the robe shut. "I didn't mean to make you uncomfortable. I should have, fuck I don't know what I should have done. Told you? Not done this? I'm sorry. I got carried away in all of it, it was so hot. I'm sorry."

"I'm sorry," I return, "I should have checked in. You mentioned him, and I assumed. I should have asked. Or not let you get carried away. I don't know. I did too."

We both sit on the bed, holding eye contact, but neither of us certain where to go next. Finally, she asks "Do you want me to go?"

"Honestly, not at all" I reply, my whole body aching at the thought of her leaving. "I meant what I said about feeling like we could be close friends. And I don't want to do anything that's gonna hurt you. So if the rest of this afternoon we just hang out, as friends, I would really like that. I'll take your lead. I don't want to do anything more that you think might cause problems for you, or you and Rob."

She smiles, looking relieved, "That sounds good, because I really think we could be good friends, too." She scoots back up the bed to sit next to me against the headboard, then she turns "Should we put clothes on?"

I shrug, "I'm taking your lead."

She cocks her head to the side for a moment, contemplatively, playfully. "Well, I mean," she continues, "I've seen and been naked around enough of my friends that I don't think we have to. Not unless you want."

"I'm good without them," I smile, slipping out from under the sheet, standing up, and walking toward the closet. "But I am going to put on the other robe," I say as I slip my arms into it leaving it open in front, turning back to her.

"Are you hungry?" I ask, and notice her eyebrow arch slightly, smirking. "Shut up," I laugh, rolling my eyes, "I mean actually hungry. Do you want to order something and just chill? What time are you doing dinner?"

"Not til 8:30," she replies, "I could eat."

"Wouldn't know," I quip nodding down toward my own pussy, and her jaw drops. "Kidding! Too soon?"

"Rude!" She flips me off playfully and giggles. "Sure, let's order something."

"Go ahead and order what you want," I say, turning toward the bathroom. "I've gotta pee. Order me a club sandwich, please?"

"Gotcha," she says, picking up the receiver as I walk toward the bathroom. I contemplate stepping into the shower again like last night, but I don't. I sit on the toilet and spread my legs slightly, glancing down at my swollen pussy that is still aching and aroused. I reach between with my finger tips and pull gently at my pussy lips. My inner labia slick, my clit swollen, everything pink and puffy. My stream of pee splashes into the toilet. The little release, sending a tingly shudder up my spine. I think about how hard I'm going to make myself cum tonight remembering Jess's amazing rolling orgasms. How glad I am that little for that puddle of squirt she left on my sheets, knowing my bed will smell like her cunt long after she leaves for dinner with Rob.

I finish peeing and wipe myself. Then I slide to fingers in my slit and pump them in and out a few times to tease myself, before pulling them out and washing my hands. I wrap the robe around me and tie it shut before I walk back out to the room to find Jess has picked up all my toys, has them lined up on the bed, and is studying them.

"Which one?" she asks me, gesturing to the array of toys in front of her.

"Which one, what?" I ask back, my pussy twitching slightly, as I try to figure out what she's asking me.

"Last night," she continues, "which one were using last night when we heard you."

I walk over to the bed and sit down next to her. "This one," I say picking up the 5 inch pink dildo "when you heard me in the hot tub. And that one," I point to the 8 inch green one "when I fucked myself on the rolling chair pressed against the wall listening to you."

"I see," she says, quietly "Have you used any of the others yet this weekend?"

I shake my head no. "Not yet."

"I see," she says again, uncrossing and recrossing her legs. She's horny again, but I do nothing. I'm taking her lead..

"Do you have toys?" I ask her, following her gaze as she trails it across the collection of self-pleasure items.

She shakes her head, "Not like this. I've got a little bullet vibe that I use sometimes. But mostly, I just use my fingers. I've never used a dildo before." She's trying to keep her voice light, but I can hear the twinge of arousal. "That green one is huge."

"Yeah, that one I had to work up to taking," I tell her. "I have to be insanely horny for it to be comfortable."

"And that's what you were using last night when we were fucking?" she murmurs.

"Yeah," I reply, pausing before I continue, not sure I should. But I do. "I was so wet it slipped in and stretched me out easier than it ever has."

"Wow," her voice a whisper now. Her eyes glancing from toy to toy.

I can feel my pussy leaking, the slipperiness of my juices seeping down between my thighs. I want grab a toy and pleasure her with it. I want to grab one and pleasure myself.

I do neither. I am taking her lead.

"These," she gestures to the clit suckers, still breathless "you like these?"

"Mmhmm," I affirm. "I like all of them. Sometimes I use those on my clit while I have one of the dildos inside me."

She lets out a truncated little moan, but catches it, "Do you use this one?" She is almost whimpering now as she gestures to the self-thrusting dildo. It's the most realistic of the 3 dildos I brought. Caucasian flesh colored silicone, about 6 inches. Supple. With a motor that gives it some decent thrusting capability.

"Sometimes," I tell her, "If I really want to lie back and do no work. It's a slow build up with that one. Sometimes I'll find a porn video and let it match the pace."

"Jesus," her breath controlled, but barely. She pauses, and I can see she is deciding whether or not to say her next thought.

I continue, "I can put them away if it makes you feel weird." Knowing she doesn't want me to put them away, but wanting her to say it. It's her choice, and I don't want to influence her by telling her how badly I want to use my toys for her. With her. I'm taking her lead.

I watch her face fall a little, as she nods, "That might be a good idea."

I nod, stepping out of bed again to grab the bag I brought all my toys in from the floor. I set it on the foot of the bed and start putting my toys away, one by one. I pick each up, and can feel Jess's eyes on me. I hope she's imagining me using them.

I've put away all but the three dildos, and I've got the green one in my hand when her breath catches again, "Wait." She leans forward and grabs the self thrusting dildo, the leans back on the headboard."

I raise an eyebrow, as she points to the desk chair still over at the wall our rooms share. "I want to see what you did last night. Show me?"

My pussy throbs. I want to cum so badly. And I want to cum for Jess. I'm following her lead. "That...are you sure that's okay?"

I can hear the arousal in her voice intensifying, "You'll be over there, and I am just watching. That's like porn right?"

I step toward the chair, setting the green 8-incher on to it. Knowing I'm so wet, I'll have no problem accommodating him. "You tell me?"

She has slipped the self-thruster under the blanket on her lap, I hear it's gentle mechanical whir start. Jess's eyes widen as I watch her arm moving under the blanket. By the sound of it, she hasn't inserted the toy, but by her face I am guessing it's tapping right at her cunt entrance. "I want you to let me watch you."

"It's what a good friend would do?" I smirk, letting my robe fall open as I straddle over the dildo. My wetness glistening all over my inner thighs, lowering myself so the head is positioned right at my slit.

"The best friend," she exhales, as I bring my pussy down onto dildo carefully. Bending my knees so the head separates my lips, as I descend. My eager cunt stretching easily and pleasantly to accommodate him. I'm more turned on that last night. The fullness inside me radiating pleasure through my core. I hold eye contact with Jess as I start to rock my hips.

She's pushed the self-thruster in and his holding it in place with a pillow between her legs. I can tell because both of her hands are up at her tits now, pinching and pulling at her nipples, and her eyes are wide and locked with mine. I can just barely make out the mid-tempo purr of the toy inside her and I match it's pace with my rocking, fucking myself on the chair as she watches me.

"I was right here at this wall," I tell her, my voice soft and edged with lust, "listening to you and Rob." I swivel my hips in a long, slow gyration. Stirring my soaked cunt on the dildo.

"Fuck," she mutters softly, I can see her grinding her own hips against the dildo against the pillow she has between her legs.

I continue as I grind myself, feeling the pleasure building as I ride, "I had myself straddled on this cock while I pressed myself to the wall listening to you ride him."

"That's so hot," she breathes, her fingers rolling her perfect little nipples between them.

"Hearing you," I say, exhaling for emphasis, lifting up half way and then pushing back down. "Hearing you tell him you wanted to be a good girl as you rode. Knowing you could both hear me. Fuck it made my cunt feel so good. It feels so good right now."

"Me too," she sighs, lifting her own hips up under the blanket and then down. Reaching between her legs and pulling the pillow firmly against her. "I came so hard on his cock hearing you."

"I wanted you too," I moan, reaching up with one hand to my own breasts squeezing them, the other down to rub across my clit. I start to bounce a little faster.

Jess's breath catching, I know she's enjoying the sensation of the toy pushing in and out of her horny, perfect pussy.

"Wishing I was getting fucked for you," I continue, feeling my own orgasm starting to approach. Knowing I'm going to cum soon. Preparing myself to ride this dildo to an intense climax right in front of her.

Then we hear the knock on the door.

"Room service," a male voice calls from the hall.

We both freeze momentarily, but then I'm up off the dildo, and moving it to the door faster than Jess's horny, aroused brain can processes, "Pretend you're asleep," I whisper.

Her eyes widen with disbelief as she realizes I'm about to answer the door, leaving the dildo I've just dismounted glistening in the chair, and giving her no time to pull out the one thrusting inside her own cunt.

"Caitlin, wait!" she hisses quietly, but I've already looked through the peephole and seen it is my friend from this morning.

I open the door to him, my robe hanging open. He starts to open his mouth to say something, but his words get stuck as he tries to process my naked body in the doorway. "You said, if I needed anything else, to ask."

His brain is short circuiting as the blood rushes to his dick, I glance down and there is an obvious bulge already. "I, uh..yeah...shit..."

"Put the food down and be quiet, my friend is sleeping" I tell him, stepping to the side and letting him enter the room. He walks to the table, and sets the food down. I follow him, watching him glance at the still-slick dildo on the chair first, and then toward Jess in the bed. She's slumped down now and lying on her side, eyes closed. He might believe she's asleep, but I know that dildo is still pumping into her cunt and there's nothing she can do if she wants to avoid giving herself away.

He turns to me, and I hold a finger up to my lips, and mouth "Quiet." His brown eyes wide with surprise and desire as he moves to me. I reach between us and undo his pants quickly and tug them down. His rock hard cock springs out with enough force that it thumps against his stomach on the back swing. It's not quite as big as my green dildo, but a solid 6 inches with girth. And his is positively rigid.

I knock the green dildo up off the chair and push him down into it. He doesn't resist. I turn the chair so his back to toward Jess. I want to be able to see her as I ride him, and I want her to be able to watch me do it. I grab his hands and move them to my hips as I straddle his cock. He bucks up, urgently, impatiently, like a 20-year-old guy who can't believe his porn-y fantasy is happening. His flared cockhead penetrating me and I press down to meet him. Filling myself with his engorged cock and starting to grind.

He reaches his mouth up to find mine, but I'm not interested in kissing this guy. I want his cock. I want to ride him until I cum. But I don't need to kiss him. I lean so his lips meet my neck and feel them sucking and kissing the sensitive skin. I grind my clit against his hips as he pumps up into me. His hands gripping and pulling and grasping anywhere he can. He's not going to last.

Jess's eyes are open now, frantic. Watching me. My mouth is open, panting quietly as I fuck this guy right here in front of her. She's rocking her hips gently and I can tell the dildo thrusting into her is pushing her to the edge. I start whispering in his ear as I feel him start to tighten up underneath me, approaching the edge, "fuck me. I want to feel you fill me. I want to feel you empty your load in me."

He pulls his lips away from my neck and starts grunting, his nails digging into my skin. His audible desire and Jess's silent desperation bringing me to the brink.

"Shhh, shhh," I say, pulling his head back to my shoulder. Biting his ear lobe between my teeth, "Fuck me, make me cum. Fill me."

He bites down on my shoulder, stifling a groan as he shoves his throbbing cock as deep up into me as he can. My mouth drops open as my orgasm starts, "Fuck, I'm cumming," I whimper as much to Jess as to him. I see her own hips bucking a quietly as she can as the toy fucks her over the edge. She starts cumming, silently in my bed.

He grunts, "shit, fuck..." and I feel his cock spasm inside me as deep, pulsating waves rip through me. His hot cum pouring into my greedy, desperate cunt.

"Cum in me," I gasp, clenching around him as he bucks and shudders. My own legs shaking as my orgasm slowly releases me. I feel him drive one last pump into me and then sink into the chair panting.

I collapse and him, our bodies sweating. Jess making desperate eye contact with me as her own pussy continues to be fucked quietly by that self thrusting dildo in the bed in front of me. She's cumming again, and I dont know how long she can keep from moaning.

I dismount his cock swiftly, and grab his hand pulling him up out of the chair. He looks bewildered as I lead him to the door. His deflating, cum-covered cock still

hanging out of his pants. He fumbles for his fly as I open the door, "Thank you. That was just what I needed," I say.

He gets no words out as I push him firmly into the hall, dick in hand. And shut the door.