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Playing With My Babysitter

"My babysitter introduces me to sex toys and anal play."

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Author's Notes

"An 18-year-old girl explores her sexuality with her mature neighbor, Mrs. Jones, who is babysitting her for the weekend. This is the fourth installment, which can be read on its own. To get the full naughty experience, read the previous parts—you won't want to miss out on the fun! The cover features the beautiful Musicals62, who graciously permitted the use of her photo."

Dressed in only a sheer pink babydoll that barely covers my buttcheeks with no panties underneath, I walk barefoot downstairs and into the kitchen, where my babysitter, Mrs. Jones, is slicing up fruit for breakfast. Her hips sway in a seductive rhythm as she hums a soft melody.

My mother's silken robe clings to her supple figure like a second skin, accentuating every curve. I can't help but notice how she's pinned her red hair up in an artfully messy bun, revealing the graceful curve of her neck. Her emerald eyes widen in surprise as she catches me staring, a warm smile spreading across her face.

With a coy smirk, her gaze sweeps over me, lingering on my perky breasts. The sheer lace can barely contain my stiff nipples, which beg to be touched, and as the fabric delicately grazes them, my rosy areolas peek out teasingly. Butterflies flutter in my stomach as I feel her eyes on me, and all I want is for her to play with me again.

Without missing a beat, Mrs. Jones hands me a plate of freshly cut fruit and purrs, "You look good enough to eat, my sweet little girl."

I can't help but blush a little at her remark, a rush of excitement coursing through me in response to her flirtation. Mrs. Jones winks at me and sits on the stool next to the kitchen island, crossing her legs while biting into a juicy strawberry.

She eats the fruit slowly, savoring each bite, while I just watch her, my plate forgotten in front of me. I don't feel hungry, at least not for food, because my appetite has shifted to something entirely different in her presence.

As I take a seat beside her, Mrs. Jones chuckles and extends her hand toward me. "You've got a little juice there," she remarks, amused.

With a teasing smile, she delicately wipes the traces of her wetness from my chin. As she holds my gaze, images of her velvet folds come to mind, and I can still taste the salty, tangy flavor of her essence on my lips.

"Care for a taste?" Mrs. Jones purrs.

I'm not sure what she is offering until she picks up a strawberry and holds it to my lips, her eyes dark with desire. I take a bite, savoring the sweetness that lingers on my tongue, wishing Mrs. Jones was offering me her pussy instead.

Her gaze pierces through me, as if she can read the dirty thoughts that consume me. With a deliberate movement, she brings the succulent fruit to her lips and slowly runs her tongue along its length, savoring every drop of juice that drips down her delicate fingers. The memory of how her tongue swirled around my clit and her fingers teased my core last night suddenly floods my mind. My vaginal walls clench in response, aching for her touch as much as I ache for the taste of the strawberry on her lips.

"Your mom mentioned you are dating a boy," Mrs. Jones casually mentions, leaning back in her chair, breaking the intimate moment between us.

"Was," I emphasize. "Ben and I ended things last week."

To be honest, I'm not that upset about it. I basically dated him because my parents approved, and well, I wanted to lose my virginity because I was the only one in my friend group who hadn't yet.

Mrs. Jones' eyes are bright with interest. "I'm sorry to hear that, sweety. How long have you two been dating?"

"For about a year."

"That is a long time," she says, her voice filled with sympathy. "And breaking up right before your 18th birthday must have been really hard."

Not really. The jerk got caught sneaking out to see me and then threw me under the bus. His parents labeled me a bad influence and complained to mine, so I broke up with him. Thanks to Ben, instead of throwing a huge party for my 18th while my parents are out of town, I'm stuck spending the weekend with Mrs. Jones babysitting me. I guess I owe him one, huh?

"It's okay, Mrs. Jones. It was a mutual decision," I reply, trying to sound nonchalant. "I'm actually relieved it's over."

"Oh," she responds, looking slightly surprised. "Was he your first boyfriend?"

"Yes, he was," I admit, my voice straining from her probing questions.

Mrs. Jones nods. "Did you lose your virginity with him?" Her brow furrows slightly, as if she is waiting for my reaction.

A blush creeps up my neck. "Um, yes," I stammer, secretly wishing the ground would just swallow me up.

Mrs. Jones leans in, her voice lowering. "You did use protection, right?"

I squirm in my seat, her directness piercing through me. "Yes, I'm on the pill," I admit, my voice barely above a whisper.

She nods, a look of approval in her eyes. "Smart girl."

I rush to add, "But please, don't tell my mom!" My parents still believe I am a virgin. They have no idea I've even been to a gynecologist.

Mrs. Jones chuckles softly. "All your secrets are safe with me, sweetheart."

I sigh with relief. "Thank you."

"No need to worry," Mrs. Jones reassures me. "So, about John—"

Cutting her off, I hastily add, "And I won't say a word to anyone about you having sex with the coach."

Mrs. Jones nods, a warm smile spreading across her face. "I appreciate that, honey. I really enjoy spending time with him. John makes me feel young and attractive again." She pauses, her gaze meeting mine with a mischievous glint. "He's incredibly hot, don't you think?"

For a man in his thirties, the coach carried himself as if in his prime, his rugged charm effortlessly attracting the attention of every girl around him—I wasn't immune to it either.

"Every girl on the team seems to have a crush on him," I say, carefully avoiding revealing my admiration for the coach.

Mrs. Jones laughs heartily. "Well, I can't blame them. He's quite a stud. Have you seen his abs? Like a washboard, I tell you!"

I let out a nervous chuckle, eager to keep my own crush on him a secret. "Yeah, he definitely takes care of himself," I reply, hoping my casual response hides my true feelings.

Mrs. Jones grins mischievously and says, "Let me tell you about his cock. It's as divine as a Greek god's!"

I can feel my face flush at her suggestive words.

"It's so thick, and he knows just how to use it," Mrs. Jones adds, leaning in closer as if sharing a scandalous secret. "You'd have to experience it for yourself to truly understand," she teases with a wink, leaving me completely flustered.

"Umm," I stammer, scrambling for a way to change the topic. "He's a great motivator and really pushes us to do our best," I blurt out, hoping to guide the conversation towards his professional attributes. But all I can think about is his "divine" cock, which I glimpsed through the keyhole in my parents' bedroom while spying on him having sex with Mrs. Jones.

Mrs. Jones nods. "John certainly knows how to bring out the best in his girls. Both on and off the field," she adds with a wide smile, making me blush even more. Popping a grape into her mouth, Mrs. Jones smirks. "So, how was Ben in bed?"

Oh god… She isn't going to drop this topic, is she? "He was… okay."

Mrs. Jones raises an eyebrow, clearly unimpressed by my response. "Just okay?" she probes, clearly expecting more.

"I never had an orgasm with him," I admit, feeling a rush of embarrassment.

"No! Really?"

I nod. "Ben was… well, he was quick to finish."

"It makes sense. After all, you're quite stunning." Mrs. Jones pauses, allowing the compliment to sink in before adding, "I'd wager that boy was simply out of his depth with you." She gives a knowing smile and casually reaches for another grape. "Well, John is quite the attentive lover. He always ensures my satisfaction, unlike my husband, who neglects my needs entirely," Mrs. Jones remarks with a hint of disappointment, her smile fading as she speaks.

I fidget in my seat, my mind consumed with images of the coach ravishing me just like he did her. The heat between my thighs builds, causing a tingling sensation to spread throughout my body. All I can think about is the coach's muscular hands on my skin, his lips on mine, and how his cock would feel inside me.

"It's refreshing to be with someone who cares about my pleasure," Mrs. Jones adds, her smile suggestive as she gazes at me. She reaches out, her fingers tracing lightly along my jawline. "You were amazing this morning."

I can't help but feel a surge of pride at her words.

"So," Mrs. Jones continues, her fingers now moving down my chest, "I'm curious about Ben. How far did you go with him?" 

I swallow nervously, not expecting this turn in the conversation. "Erm… We did just the usual stuff…"

"You mean vaginal penetration?"

I clear my throat, feeling the heat rise to my cheeks. "Yes."

Despite my obvious discomfort, Mrs. Jones asks, "Did you ever give a blowjob to Ben?"

I clear my throat. "Um, no, I didn't."

"Hmm."

Her fingers graze lightly across my left breast, my nipple hardening under her touch. My breath hitches as she expertly tugs and twists the delicate bud between her thumb and forefinger, making my knees weak. The heat pooling between my thighs intensifies as she leans in closer, her warm breath tickling my lips.

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"How about anal?" Mrs. Jones asks, her voice sultry.

"No!" I gasp, shaking my head vigorously.

Mrs. Jones chuckles at my intense response, her hand moving down my stomach and lower until it lands on my thigh.

"Why not?" she whispers, her eyes locked with mine.

I avert my gaze, feeling the weight of her stare as I struggle for words that won't come. "I don't know," I finally say. "It just never appealed to me, I guess."

Mrs. Jones nods understandingly. "Well, you never know until you try," she purrs, her fingers teasing up my thigh and towards my throbbing core.

"Until this morning, you had no idea you enjoyed eating pussy." Mrs. Jones chuckles as her fingers teasingly brush against my delicate nether lips. Her voice drops to a whisper, "And you're a natural at it, too."

"Maybe one day I'll give it a shot," I whisper.

"I think you'd enjoy it."

A gasp escapes my lips as two of her fingers dip into my wetness, coloring my cheeks with a deep shade of crimson.

"You just need the right teacher," Mrs. Jones whispers against my lips before withdrawing her fingers from my dripping arousal and bringing them to her lips, tasting me with a wicked smile. "Trust me, you won't regret it."

Suddenly, almost as if someone else is speaking through me, I hear myself say, "Okay."

Mrs. Jones grins like a cat who just caught the canary. "Good," she purrs, getting up from her seat. "Let's go."

Instinctively, I rise from my chair, my pulse quickening. Wait… What did I just agree to?

Mrs. Jones' gaze lingers on the spot where I had been sitting, a telltale mark of my arousal glistening on the surface.

"Oh," I stammer, feeling my face flush.

Her lips curl into a smirk, and she coos in a soothing tone, "Don't worry, sweety, it's perfectly natural. Just follow me, and we'll take care of it together."

I take a deep breath and follow Mrs. Jones up the stairs to my parents' bedroom. The bed is a mess, sheets all crumpled and tossed aside from her having sex with the coach yesterday. I linger in the doorway as she kneels to open a suitcase spread across the floor.

Mrs. Jones picks up a black velvet pouch and pulls out a metallic, cone-shaped object. It tapers to a thin tip, bulges in the middle, and has a flared base.

"Do you know what this is, honey?" Mrs. Jones asks as she stands up and walks towards me, holding the object out for me to see.

I shake my head, reluctant to take a guess and make a fool of myself.

"This is a butt plug," she says. "It's used for anal play. Would you like me to show you how it works?"

Oh, my. I feel my face burn bright red, and I want to decline, but I also feel a strange curiosity and decide to nod. Mrs. Jones knows what she's doing, and I trust her to guide me through this new experience. She smiles, walks over to the bed, and grabs a bottle of lube from the bedside table.

"Come on, sweetheart, get on the bed on all fours," Mrs. Jones purrs.

I awkwardly position myself on the bed, trying to slow down my racing heart. Mrs. Jones stands by the bed, looking down at me with a naughty smile. After she places the plug and the lube on the bed next to me, she walks behind me, her hands caressing my buttcheeks, spreading them apart gently.

"Relax, my sweet girl. This is going to feel so good," she whispers.

As she gently traces my backdoor with her warm, wet tongue, I can feel my muscles clench with excitement. Her playful licks and gentle caresses fill me with desire. This is so intense and intimate!

"Mmm," she murmurs, "just enjoy. Let me take care of you."

I close my eyes and surrender to the delicious feeling of her hot tongue gliding in sensual circles around the sensitive skin surrounding my virginal hole. This feels amazing!

Mrs. Jones' skilled tongue presses against my tight opening, slowly pushing past the initial resistance. I gasp in pleasure as she explores deeper, penetrating my tiny hole with increasing pressure. This is so naughty!

With each probing and teasing movement, I can't help but let out a low moan. Never in my wildest dreams did I imagine that such a taboo act could bring me so much pleasure.

As her luscious tongue continues its seductive dance, I can feel my wetness dripping down my trembling thighs. With each dive into my tight hole, Mrs. Jones sets off a chain reaction inside of me that has me writhing with need.

"Now that your pink little hole is all wet and relaxed, I think it's time to move on to the next step," Mrs. Jones whispers.

My breath hitches as she grabs the plug. "The first and most important thing is to always use plenty of lube," she advises, gently squeezing some onto her hand and spreading it all over the toy.

"Trust me, sweety," she coos. "This will feel amazing once it's in."

Oh, I hope she is right! That plug looks intimidating, but I trust her.

Mrs. Jones presses the lubricated plug against my rosebud, slowly easing it in. As it slides deeper inside, the pressure builds but never reaches the point of pain.

"Just breathe," Mrs. Jones murmurs as she pushes it further.

The stretching sensation becomes slightly painful, so I unintentionally clench my muscles, but Mrs. Jones reminds me to relax and take deep breaths as the toy fills me up.

"There we go," she murmurs, her voice soothing as the plug slides into place.

As the plug settles in my tight little hole, the sensation is intense but not painful—just a fullness. This feeling is like nothing I've ever experienced before… and I love it. I am such a bad girl! With each breath, I can't help but let out small whimpers of pleasure as my clit throbs with excitement.

"See, you're doing great, sweetheart," Mrs. Jones encourages.

Her fingers slide across my swollen labia, calming my nerves and heightening my arousal.

"Mmm, you are so wet, sweety," she purrs. "I think you need something to help you release all that tension."

Mrs. Jones walks over to her suitcase and brings back a vibrator, its buzzing sound filling the room. "This should do the trick," she says before slowly pushing the toy inside my pulsing core. Because I have a butt plug in place, the sensation of the vibrator is intensified, and I feel so full and stimulated in a way I never have before.

"It's not as thick as John's," Mrs. Jones says. "But it should still hit the spot."

Oh, no! Now I can't help but imagine that the vibrator is the coach's cock. And it feels so good. I shouldn't want him! He is my teacher, and it's wrong, but I can't help but crave his cock deep inside me.

As Mrs. Jones moves the vibrator in and out of me, I can't help but moan, feeling the intense pleasure building up inside me as I imagine the coach's cock stretching me, filling me completely.

With each thrust of the vibrator, I feel myself getting closer and closer to the edge, my body quivering with want. The vibrator may not be the real thing, but in this moment, it's close enough to make me feel like I'm being taken by the coach himself.

"Mphm," I moan as Mrs. Jones increases the intensity.

The fantasy of the coach becomes more vivid, making me ache for the real thing even more. I can't suppress the moans and whimpers of desperate pleasure escaping my lips as I lose myself in the fantasy.

"That's it, my naughty girl. Let go," Mrs. Jones whispers.

My body trembles with the intensity of the pleasure, and my mind is consumed by the forbidden fantasy of having sex with the coach. In this state of euphoria, the boundaries between what's real and what's not fade away as I give myself fully to this irresistible urge. I cry out as waves of ecstasy wash over me, feeling the coach's cock inside me as if it were truly happening.

"Oh, yes!" I gasp, unable to control my body's response to the overwhelming sensations.

"Such a good girl," Mrs. Jones praises, her voice a soothing balm to my racing heart filled with desire and guilt.

My eyes flutter open, and the lingering sensations are still pulsing through my body as she pulls out the vibrator from between my legs. I lie down on my back, panting heavily, my mind reeling from the intensity of the experience.

Mrs. Jones smiles in a way, as if she knew what I was feeling. "You did so well, sweety."

I manage only a weak smile in response.

"I adore the way your cheeks flush with a rosy hue when you cum," Mrs. Jones whispers tenderly, her delicate fingertips caressing my sensitive folds. She positions herself between my legs and gazes up at me with a playful smirk. "We simply can't let this nectar go to waste," she declares before eagerly delving in with her tongue, stirring up another intoxicating wave of bliss within me.

TO BE CONTINUED...

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Written by EMoon
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