The Beautiful Mistake Pt. 05

Story Info
Time for a more advanced lesson.
4.7k words
4.75
6k
8

Part 5 of the 12 part series

Updated 03/13/2024
Created 08/22/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

While my plans for mine and Chloe's little getaway were playing out splendidly, I had made one small mistake. At the end of our afternoon of smoking and making love in the sun, I told her that I had made a reservation for us at a bistro twenty-five minutes away. This proved to be a problem as she, not knowing in advance what we'd be doing, hadn't packed anything worthy of wearing to such an elegant place.

So now I find myself in a department store, standing outside the fitting rooms as she tries on eight different dresses. It's the sort of situation that normally makes me bored and irritable, but I'm keeping it together. There's an appealing make-believe to the whole situation. I drove my mistress in a BMW to take her dress shopping before a night on the town. Sure, the BMW is a rental, I can't really afford any of the dresses she's trying, let alone the dinner we're going to have, but it's fun to act like this is my life.

"Ok!" I hear her call out through the door. "I think I found it!"

Steps out. Find it she did. The dress is a silky dark burgandy that contrasts beautifully with her pale olive skin. And quite a bit of skin there is to contrast with. The dress ends halfway up her thighs and is cut low across her chest, showing her deep cleavage. The spaghetti straps do nothing to cover up her smooth, milky shoulders.

"What do you think?" she asks, nervously.

"It's... wow."

She brightens up.

"Really?"

"Oh, absolutely."

"Well then," she says, turning around, "pop the tag off. Let's check out and get going. Are we going to make the reservation?"

"Just barely, but yes."

Soon we're at the restaurant, some faux-posh place called the Finch and Olive. I've never been here before, but the reviews were all good. It's your standard pretentious bistro- dark walls, low lighting, fake candles on every table. As soon as we enter, a change comes over Chloe. She is suddenly quiet and unsure. But God does she look gorgeous in this light. I notice two different gentlemen glance at her as we make our way through the dining room to our table. I know exactly what they're thinking. They're thinking that I am a lucky, lucky man. And they'd be right.

Once we are seated, Chloe leans forward and says, almost at a whisper, "I've never been to a place like this before."

"Really?"

"The closest I've been is, like, an Applebees."

I laugh on the inside.

"Well, it's just like eating at any other restaurant. You order, you eat. Easy-peasy."

I open my menu and she follows suit.

"Are these little numbers beneath the prices?!" she asks, again at a whisper.

"They are, yes. Don't worry about it. Order what you want. Just, you know, don't expect this treatment often."

The waiter comes over for our drink orders. I ask for an old fashioned.

"And the lady?" he asks, turning to Chloe. She looks like a deer in headlights.

"A glass of the house red, I think." I answer for her.

"Very good." the waiter replies before walking away.

"I'm not twenty-one." she says.

"You certainly look quite mature in that dress and in this setting. If you don't want it-"

"No, no I do! I just don't want to get you in trouble."

"Really? You don't want to get me in trouble?"

"Ha! Fair enough."

"So, I assume they don't serve oysters at Applebees?"

"What are those again? They're not snails, are they? I'm not eating snails."

"Ha. No, that's escargot. Not a fan. Oysters are ocean molluscs."

"Molluscs is not really an appetizing word."

"I'll just order a couple for each of us so you can try it."

This does not go over well. She does not find the sight of the oysters appealing. And when, after some convincing, she finally eats one, she makes a face of pure disgust. Realizing there's no place for her to spit it out, she reluctantly swallows.

"Loved it, huh?" I ask.

"It's like swallowing a load of rancid cum."

I laugh.

"Charming. Well, I'll eat your other one then, I guess, despite that description."

"Please do."

The entree course goes better. She ordered the chicken, and I wonder if that's due to her immature pallet or because it's the cheapest option. Either way, it doesn't matter as she enjoys it immensely.

"So," she says, as she sips her second glass of wine, "If I'm not to expect this treatment often, what am I to expect?"

"What do you mean?"

"I mean... what are we doing, exactly?"

Oh boy. We're having this conversation. I shouldn't have ordered her wine.

"What are we doing at this restaurant?"

"No! I mean, we're having fun. It's... it's amazing. But what does it mean? And how long does it last? My freshman year will be over in a couple months and I'll be home all summer. We've been doing this every few months during my limited time off. What happens when we can see each other all the time?"

"Well, we're never going to be able to see each other all the time. I've got my life to live, you've got yours. Besides, if we spend too much time together, people are bound to notice."

"True."

"If you want to know how this ends or when- I don't know. It will have to end. I hope you don't have an impression that I'd ever-"

"No! No. I wouldn't want that. You know, my parents split when I was three. It was because my father had been having an affair with a woman from work, Deborah. After the divorce, he and Deborah lived together for, like, five years. They were miserable. I can still remember her, she was a grade A bitch. The thought that I would ruin what you and Jen have-"

"That won't happen."

"'Cause I love Jen."

"I know."

"I love Lena.'

"I know."

"I- I love you. But, don't take it like, you know, I love you. I mean like the way I have for years, like, like..."

"I get what you mean. You care about me."

"Yes."

"I care about you too. I don't want any of us to get hurt by this. Which is why we'll continue to be cautious. And the moment it seems like it's getting too complicated or it stops being fun, we'll drop it."

"You make it sound so easy."

"Why can't it be?"

She takes a minute before answering.

"You're right. It can be. I will be."

She giggles to herself as she pushes a black curl away from her face.

"What is it?" I ask.

"Oh, it's just... Earlier in the car, I was wondering what exactly we are to each other. You know? What words would define our relationship to one another. 'Cause I guess I'm technically, like, you're mistress? Your side piece? But those don't feel right. And then I thought..."

"What?"

"It's like I'm your apprentice. You're my teacher or master. But the word that popped in my head that felt the most right was sensei."

"I like that. I like that a lot. You know why? Because that is a relationship designed to end. One day you will have learned all you need from me and will move on to bigger and better things."

"Yeah! Though I don't know what could be better and I certainly don't need anything, ahem, bigger."

"That statement alone shows what a naive young apprentice you are."

"I guess there's still much for you to teach me, master."

"Indeed, young one. And what lesson would you like next?"

"Well," Chloe says with a twinkle in her eye, "I think I've got the basics down."

"I'd say."

"So I'd like to try something a little more... advanced."

"And what's that?"

She leans in close, deepening her cleavage.

She whispers, "I've never been fucked in the ass before."

Good lord, it's happening. I'd fantasized this might happen tonight, but didn't think it would.

"And you think you're ready?"

"I don't know. But I'd like to find out if I am. Brian- he asked me to a few times. I guess I just didn't trust him enough. I'd some, you know, experimenting with it on my own, but, like, a handful of times. Then, right after I got back to school post winter break, some friends and I went to a sex shop on a lark and there was this.. Anal training... device... thing. I went back the next day and bought it. It's... it's nice, but I know the difference between a loose piece of silicone and a true pulsating cock connected to a person... I enjoy both in my vagina, but, as I say, they're very different experiences. I imagine they're quite different in the ass as well."

"Well, should we skip dessert and go find out?"

She bites her lip.

"I don't know," she says playfully. "What do they have for dessert?"

I hesitate.

"JK!" she says with a laugh. "Let's get out of here!"

It's Spring. The day was sunny and warm but the night is cold. Chloe starts shivering the second we exit the restaurant. She only has a single piece of fabric wrapped around her torso, after all. I give her my jacket.

As soon as we get back to the yurt, Chloe wraps up in a blanket as I get a fire going in the woodstove, throwing on plenty of wood. She steps out for a minute (the bathroom is a separate structure.) While she is gone, I get things set up. I pull the collapsable massage table out from under the bed and unfold it. Then I go to my bag and pull out a bottle of sweet almond oil and a dozen candles. I light the candles and set them all around the yurt. I throw a few more chunks of wood on the fire. It's really going and the yurt is already comfortably warm.

Chloe comes back in the blanket wrapped tightly around her, her dress in her hand, her hair pulled back in a tight ponytail.

"What's this?"

"The key to tonight's lesson," I tell her, "is relaxation."

"I've never had a serious massage before."

"It's a night of many firsts. You feeling warmer?"

"Yes."

"Good, because you're going to have to lose the blanket."

I turn off the electric light. Only the candles and the fire illuminate the room now. She drops the blanket, revealing her nude body. I hold my breath while I take in the sight. The flickering candlelight shimmers on her alabaster skin. Her body is perfectly shaped. Her heart shaped face rests atop a delicate neck that leads to sloping shoulders. Her torso is an hourglass, with her exquisitely proportioned breasts above and curving hips below. Her lines of her hips taper down along the thighs and calves to her dainty feet.

"Well," I say, patting the massage table. "Shall we?"

"How do you want me?"

"Lay on your belly, head in the loop here, arms at your sides."

She climbs onto the table.

"Oh!" she squeaks. "It's cold!"

"I can tell," I reply, glancing at her sudden goosebumps. "Don't worry, it'll be warm in minutes."

She lays down and my eyes are glued to her ample, heart-shaped butt. Tonight that ass is mine. But we must be patient. Do it right. Savor.

I had placed the bottle of oil right next to the stove to warm it up. I grab it, pop the lid, and sprinkle oil on her shoulders, her back, her ass, her thighs, her calves, her feet. The scent of sweet almonds suddenly fills the room.

"Oh, it's so warm," she sighs pleasantly.

I begin to rub it into her skin, starting again from the shoulders and working my way down. I keep my touch light, no pressure, simply spreading the oil around to every inch of her skin. I linger longer on her butt than anywhere else. Her skin is remarkably smooth and soft, like velvet.

Once I've spread the oil on her feet, I again move back up to her shoulders. Now the real massaging begins. I'm not trained in massage. Over the years, I've watched some videos online. I know the basics. But as a pianist, my hands are well-suited for the task- large, strong, yet sensitive and agile. Jen asks for shoulder and back rubs constantly. I give her the full body treatment two or three times a year. But, as I have said about the piano, skill isn't everything, neither is natural ability. You have to love it. I love massaging. To explore another body so minutely, so intimately is a fascinating activity.

I take my time. There's a clock by the kitchenette. I work her neck and shoulders for five minutes before moving to her back. She doesn't speak, but is quite vocal in her reactions, guiding me to what movements are most pleasing to her. It seems she enjoys deep pressure. I do too. By now her goosebumps are all gone and her skin is warm to the touch.

I work her back for ten minutes, constantly faking that I'm about to move down to her butt, yet never following through. When the ten minutes are up, I take my hands from her back and jump down to her feet. She loves me massaging her feet. Her little whimpers and hums amuse me. I give each foot a few minutes a piece before moving on to her calves. Then come her thighs, her thick, powerful thighs. I dig in deep into her muscles and her light whimpers become low moans. I continually move my hands in tandem up and down, my thumbs rubbing her inner thighs, each time threatening to reach her pussy, but always stopping short.

I don't know if it's consciously or unconsciously, but she slowly spreads her legs farther and farther apart until her feet are almost off the edges of the table, making her vulva ever more visible and accessible. Clearly she is enjoying the massage, but wants my hands somewhere other than her thighs.

The fire in the stove is really doing its magic. The yurt is positively toasty. I take off my shirt.

With my thumbs, I begin to rub her labia majora, but still deny her the pleasure of touching her most sensitive parts. I press hard, massaging everywhere but where she wants it most.

"Come on!" she cries after minutes of this torture. By now she's so wet, it's gushing out and running down her hairless pubic mound.

"Oh," I say sweetly, "is the massage not to your liking?"

"Just get in there!" she groans.

"If you insist..."

I plunge my right thumb deep within her, press down on the anterior wall. She comes in an instant, her fingers spread wide, her legs quaking. As she comes down, I lean forward and whisper in her ear, "the benefits of patience."

"Yeah," she pants, almost inaudibly. "I hear ya."

"I think you should flip over now."

She gets up on the elbows and looks back at me.

"But what about my-"

"Patience."

She flips around and sits on the table.

"I hate patience," she says with a little pout.

"No you don't."

She rolls her eyes and smiles.

"No. I don't."

"Why don't you lay back?"

She does. I take a moment to savor the beauty of the candle light on her face, her full breasts, and the subtle definition of her abdominals. I grab the bottle and drench her chest in oil. The scent of almonds and the heat of the stove create a sultry atmosphere. I move to the head of the table, lean over her and begin massaging her breasts. The density of her breasts, the smoothness of her fair skin, and oil all make for a delightful tactile experience. I am almost hypnotized by the way they move as they constantly slip from my grasp. She hums and sighs as I work.

My crotch is hovering just above her head. This situation apparently becomes untenable for her and she reaches up to unbutton my pants. I keep massaging, sometimes groping the whole of the breast, other times playing delicately with her pink pointy nipples. She pulls out my cock and starts sucking on my balls. I don't have my balls sucked that often. I appreciate the novelty. She continues on while stroking my shaft. It is pleasurable, but I stay focused on my task and continue to massage her breasts, picking up the strength and intensity.

But soon her lips on my balls aren't enough, I need them clasped around my cock. I walk around to the right of the table. She turns her head to the side and immediately begins treating my glans like the tip of a popsicle. I see strains of her hair sticking to the sweat on the back of her neck. The fire in the woodstove is now blazing and the temperature in the yurt is boiling.

I pour more oil onto her belly and spend some time in gently guiding my fingers around her midriff, tracing out little patterns while savoring the sensations of her lips and tongue on my cock. Over time I work my hand down to her pubic mound. I feel her throat tighten in anticipation. I slide down further, using my index and ring fingers to spread her vulva open. And then, with great delicacy, I curl my middle finger until the tip finds her clit...

She moans with my cock still deep in her mouth. She then lets my cock go, throwing her head back down on the table.

"Oh, fuck, oh fuck, oh fuck" she says in a squeaky whisper as my middle finger flits about her clit in random little movements. I glance up and down her body, noting how each little flick of my finger affects her whole body. Toes curl, muscles twitch, breaths are cut short. I marvel that such a little part of her can have such a connection to the whole and how such delicate shifts can have such massive responses. But I think I'm done being delicate for the moment.

I slip my long, thick middle finger inside her and smile at the deep, satisfied moan it draws from her. I curve my finger so again I am rubbing her anterior wall. My palm just below my middle finger rubs her clit. I press my finger toward my palm, applying pressure both inside and outside of her.

Her ponytail is hanging through the head loop at the end of the table. Noticing it, I get inspired. I reach down and grab it, pinning her head in place. She gasps in surprise. I grind my finger inside her.

I lean down and whisper in her ear, "Are you ready for your next lesson? The one you requested?"

"Yes," she pants. "Yes... yes."

"Tell me what you want."

"I want you to fuck my ass."

"Beg."

"Oh please, fucking Christ! I need you to fuck my ass."

"And you swear no one else ever has?"

"No one."

"You never let that boy Brian?"

"No, I wouldn't let him."

"None of the boys at school?"

"No one!"

"Why not?"

"Will you please-"

"Why not let them in your ass?"

"Because... because..."

"You know why, just allow yourself to say it."

"They..."

"They? They what?"

"Oh fuck-"

"They what?"

"They didn't deserve it!"

"That's right. They weren't good enough for your fine ass."

"No!"

"They were mere boys."

"Yes! Yes."

"Your ass is for men."

"My ass is for you."

I straighten up and look down on her.

"I will let you roll over and we will move on to our next lesson," I tell her firmly, "only after you come."

I keep pulling her ponytail with my left hand and fingering her with my right. My index finger joins my middle inside her. I straighten them out, move my palm away from her, and begin finger blasting.

She grabs the sides of the table.

"Oh fuck!" she cries.

"That's right!" I shout. "Get loud! There's no one around for miles! Let it out!"

Her back arches.

"Oh, fuck!... FUCK! OH- oh, fu... FUuuuck!"

"COME ON, CHLOE!"

Her legs begin to shake uncontrollably.

"Oh fuck- I'm gonna- ah! I- I'm gonna..."

Her head, ass, and hands are the only parts of her still touching the table. Her body is bright red, her skin glistening with sweat and oil in the flickering light. Tears stream down her temples.

She screams. It's a primal, deafening scream, louder and more passionate than I ever expected. I release her hair and, with her sudden freedom, she begins to flop in wild convulsions. I keep drilling her with my fingers until her convulsions begin to lessen, then I steadily decelerate.

When I finally pull my fingers out of her, her abs crunch and her knees lift in reaction. I grab a towel and wipe my hand, cleaning off an abundant mixture of almond oil, sweat, and cervical fluid. She simply lays on the table, staring at the ceiling and breathing heavily, her eyes wide as though she were in shock.

I walk over to the kitchenette and open the minifridge. The cold rush of air on my hot, drooping balls sends a shiver up my spine. I grab a cold bottle of water.

"Thirsty?" I ask.

"Wha...?"

"You thirsty?"

"Oh... yeah. Thank you."

She sits up and accepts the water.

12