The Beautiful Mistake Pt. 11

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A vacation brings pain and pleasure.
4.3k words
4.56
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Part 11 of the 12 part series

Updated 03/13/2024
Created 08/22/2023
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This is part eleven of a serial narrative. For maximum enjoyment, please begin with part one.

***************

"Get in here!"

Jazlyn slips through the door into my hotel room. I can smell her coconut-oiled skin as she passes me. I peek into the hallway to see if anyone noticed her entering. There's no one.

"Don't be so paranoid, bro," she teases as I shut the door.

It's our second day at the resort in the Keys: Jazlyn, Jen, Felix, and me. This is mine and Jazlyn's first chance to be alone together. For Christmas, Felix bought an afternoon at a nearby spa for them and Jen. They'll be there for the next four hours.

"God, this place is incredible!" Jazlyn exclaims, staring out the French windows to the balcony and the view of the ocean beyond. She turns and presses herself back against the glass. She's wearing gray gym shorts so short they barely qualify as shorts and a hot pink t-shirt so tight you can see every muscle beneath.

"I want to ride you while looking at that view!" she declares, her eyes burning.

I smile.

"If I take you from behind, we can both enjoy the view."

"Oh yeah? And what view are you going to enjoy most? The sun on the water, or my fine brown ass?"

"I certainly enjoyed both this morning."

"Oh, you took a peek, did you?"

"Don't act surprised. You could have laid out anywhere on that beach, and you chose to spread your blanket directly in front of my chair."

"Seemed to make sense for us all to stay close."

"You need to be careful. If I notice you showing off your little bikini right in front of my face, Jen and Felix may well too. They probably did. Let us hope they figured you were just being oblivious, not thirsty."

"You mean this bikini?"

Jazlyn drops her shorts and peels her t-shirt off over her head. The bikini bottoms are thin, string-tied with a tied triangle top. The fabric is red with little green apples in a scattered pattern that stands in contrast to her milk chocolate skin.

"Lay out on the bed," I tell her. "On your belly, just as you were on the beach."

"Yes, Master," she giggles.

She stretches out on the bed. I stand behind her, my eyes traveling up her long, powerful legs.

"You know," I say quietly, "the whole time you lay like this in front of me on the beach, all I wanted to do was this..."

I grab a string end on both sides of her bikini bottom and gently pull, undoing the bows."Oh," she says. I'm not looking at her face, but I can hear she's smiling. "I wanted the exact same thing."

I pull the bikini bottoms off and marvel at her rock-solid ass glistening with tanning oil.

"And then," I whisper, "I wanted to do this..."

I grab her ass, taking as much into each hand as possible. I bring my mouth down and commence kissing and sucking both cheeks. They taste like coconut.

"And what," she moans, "did you want to do next?

Between kisses, I answer, "to... do... this."

I spread both cheeks far apart. There's not a hair to be seen; all is perfectly smooth and oiled. I drop my mouth down on her asshole and put my tongue to work.

She tenses up from neck to toes.

"Oh, I..." she says with difficulty, "I, uh- I've never done-"

I pull my mouth away and rub her star with the pad of my thumb.

"Consider this a new lesson," I say, calm yet firm. "Do you like it so far?"

"Y-yes. It's just- oh-ho..."

"It's alright. It's alright. Try to relax. You're stiff as a board! Breathe deep and slow. There you go. I'm going to use my tongue again."

"Ok- Wait... you can, but... I'm not sure I'm ready to... you know..."

"We don't have to do that today or any day if you don't desire it. For now, we'll keep things easy. You trust me?"

"Of course!"

"Of course...?"

"Of course, Master."

The tip of my tongue dances on her asshole. I insert my thumb into her pussy and massage her anterior wall while my index finger rubs her prominent clit. Jazlyn's clit is the largest I've ever interacted with and pops out from under its hood. This makes getting her to orgasm remarkably easy. Within two minutes, she's twitching and gasping in ecstasy. That's good. I want her to come while I'm licking her asshole. The goal is to wire her brain so that contact with her anus equals pleasure.

As she finishes coming, I sit up, take my thumb out of her pussy and begin to rub it against her rim while my index and middle finger slips inside her well-lubricated pussy.

"How we feeling now?" I asked.

"I think I might like it."

I press my thumb down firmer. She let out an adorable little "oh!"

"You've been a good little apprentice," I tell her. "I think you've earned a reward."

"A long, hard, throbbing reward?"

"If you insist."

I untie the drawstring of my shorts and release my raging hard-on from its confinement. I glide the whole length of it up and down her vulva, lubricating myself. I let spit fall from my mouth, landing on her anus and running down to my cock.

"Ooooo, get it in me!"

"If you insist."

A second later, my cock is sliding back and forth in her pussy like a well-oiled piston. Jazlyn starts to laugh.

"What's so funny?"

"Oh, it's just that I had always known that fucking a dick would feel amazing, even before I had done it. But now... it gets me every time just how good it really is! Fuck!"

"That's good. Make some noise! Let it out."

"Oooh fuck! Yes! Fuck!"

She keeps shouting variations of 'yes' and 'fuck.' It's not the most creative way of expressing herself, but she'll learn. I'm not worried about the noise. The walls at this hotel seem surprisingly well-insulated. Each shout of hers makes me thrust harder.

I notice Jen left a small bottle of oil on her nightstand. Inspired, I snatch it up and pour a generous amount all over Jazlyn's ass. I pour a stream down her crack, watch it flow over her asshole, and then down to my ever-lunging cock. I massage her cheeks, relishing the density of her muscles. My thumb finds her star once more. I press down on it, harder and harder still. Between the pressure and the oil...

"Jesus! Warn a girl first!"

"Should I stop?"

"...No. Just, no more surprises!"

I honestly didn't expect more than the tip of my thumb to go in, but her opening was so oily and so relaxed that it just popped in, past the first knuckle. I begin to rock my thumb ever-so slightly.

"You're doing very well," I assure her.

"Thanks. I have a good teacher."z

Over the course of the next ten minutes, I keep fucking at a steady pace while I gently work my thumb in her ass until, at last, it's in all the way to the second knuckle. She's no longer shouting words but constantly letting out a loud, low moan. My thumb can feel my cock moving through the septum between them.

"Now, rub that clit," I order her.

Her hand darts between her legs, and within thirty seconds, her pussy is gushing, her asshole is tightening, and her back arches as she comes again and again.

Eventually, she takes her hand away. I gingerly pull my thumb back until it's free. When I remove my cock, she collapses on the bed.

"You've earned another reward."

"Have I?" she asks breathlessly.

"You said you wanted to ride me while looking at the ocean."

"Oh, yes. I do! I- I just... I might need a bit."

"Ok, ok. You ok?"

She rolls onto her back, her head on the edge of the bed.

"Ooooo very much so I just... need a bit. But oh, that beautiful, pulsating cock of yours! Your balls must be ready to burst. Come on me. I love when guys come on me."

I stand with my cock hovering above her face. I stroke my shaft and massage her pussy juices into my cockhead. I feel my scrotum tighten. A burst of chemicals in my brain causes a burst of semen from my cock. The first blast I aim squarely for her face, drenching it. I then pull up and shoot a fine spray on her chest, some going as far as her belly button.

Jazlyn rubs her breasts, spreading my seed all over her.

"That was a good one!" she says with a smile, a thick pearly glob rolling down her cheek. She climbs off the bed. "Now, if you'll excuse me."

She goes to the bathroom and closes the door. After a couple minutes, I hear the shower flowing.

I pull some wet wipes from my travel bag and give myself a basic clean-up. I pull on my shorts, grab a pre-roll and a lighter. Jazlyn doesn't smoke. She gets drug tested sometimes before track meets. I might as well take this time alone to smoke up. I step out onto the balcony. My hot, sweaty skin is soothed by the light breeze coming from the water. The warmth of the sun relaxes my shoulders. I light up. The high hits my brain the moment smoke enters my lungs. God, life is good. Right now, life is good.

A woman on the beach comes into view. She's walking back toward the resort. Her black, thick-strap bikini displays her pear silhouette and golden-tanned skin. Her hips are wide and wonderfully curved. Her immense breasts bounce heavily with every step she takes. Her long, straight brown hair has sun-made highlights. She's almost to the building, not far from the balcony. She stops and looks up at me with green eyes. She smiles, revealing tall, blindingly white teeth. I smile back and wave. She waves, too. Then she mimes hitting a joint and gives me a thumbs up and a wink. She continues on her way, and a moment later, is out of my sight.

A second later, I hear a tap on the French windows behind me. I turn around to see Jazlyn on the other side of the glass, wrapped in a towel. I put out the joint and step back in.

"Good shower?"

"I assumed you'd join me at some point."

"Oh, if you want me to do that, keep the door open a crack. I respect a closed bathroom door. Besides, you seemed to need a break."

"I probably did."

She drops the towel, and I am once again breathless at the sight of her athletic physique and perfectly smooth, sepia-brown skin. She walks to the bed with that certain poise that comes from knowing just how exceptional her body truly is.

"I'm still not sure I'm ready to ride you quite yet."

She gets on the bed and sits up against the headboard. She spreads her legs open in a butterfly.

"But maybe if you work that tongue of yours on my pussy as well as you did on my ass, I'd be ready much sooner."

"If you insist."

I dive head-first between her legs. Eating out Jazlyn is a pure joy. She tastes different from anyone else I've ever been with. It's sweet and almost... tangy. Like a pomegranate. It's the best-tasting pussy that's ever touched my lips, that's for sure. This big clit of hers is so much fun to flick with my tongue, I could do it for ages. And this girl comes. It's not that she comes big, but that she comes a lot. After two minutes of licking that clit, she's grabbing my hair tight and forgetting to breathe. After ten minutes, she's already come three times. I go for another ten minutes.

Finally, I sit up and wipe her pussy nectar from my chin. She stares up at me, wide-eyed, her mouth hanging open. I lie back and pull my shorts off. I make a ring with my thumb and index finger wrapped around the base of my cock. It points to the ceiling, straight as an arrow. My cock is faintly pulsating in pain--the exquisite pain that comes when you've overworked the old boy of late, but he still demands to keep playing. Jen had gotten drunk last night and told me she required a solid fucking from this cock. Then this morning, after her shower, I saw her lying on the bed in her towel, and my boy had some requirements of his own. But my riding her like a beast wasn't enough to satisfy him. Coming again all over Jazlyn earlier didn't satisfy him fully either. He needs more. This cock needs to come again.

I had thought she would climb aboard, but Jazlyn gets on her hands and knees between my legs and begins another of her signature blowjobs. Her lips are so plump, her tongue so wide and soft, they soothe my aching cock. As though she instinctively knows what I need, she strokes me with a lighter touch than usual and does not deep throat or hoover, but sticks to kissing, caressing, licking, and softly sucking me like a popsicle.

I drop my head back and close my eyes. This softer, gentler approach to fellatio reminds me of Chloe. She loved taking her time with my cock, treating it like something precious that had to be treated with care and reverence. I can picture her big, pale blue eyes staring up at me as she tenderly licks my undershaft. She's beauty personified.

Jazlyn stops. I open my eyes to see her smiling.

"If I'm going to look at the ocean while I ride you, you'll need to rotate 90 degrees."

I reposition myself, and she straddles me. She grabs the base of my shaft. My cockhead kisses her labia. She lowers herself. The warmth of her pussy alleviates my cock-soreness better than anything else so far.

Jazlyn has proven herself to be an excellent cockrider. She told me it was her favorite part of porn, watching the women go cowgirl, and she figured out how to do it herself instantly and naturally. And God, I love abs. I think I've made that clear before now. I love watching them work. Jazlyn's abs are insane. I've seen plenty of women on Instagram rocking abs like these, but very few in real life. Her grinds are different from other women's. It's like when you drive a true elite sports car for the first time and you can feel the power and efficiency of the fine-tuned engine and how superior it is to any car you've driven before. Working in tandem with that sculpted belly is a powerhouse ass. I grab it with both hands and marvel at the force of its contractions. When she slides her pelvis forward and her ass muscles tighten, they become as hard as stone.

With that big clit of hers rubbing against me, Jazlyn starts coming repeatedly. She keeps picking up speed. My cock is on fire. I'm dying to come, but it just isn't happening. Jazlyn goes faster. She's a magnificent athlete; she won't stop, but keeps pushing herself to go harder. As glorious as her athletic prowess is to behold and feel, all I want is to blow a load inside her and let my aching cock finally go limp.

This is only her third time ever riding cock, but she is already a master. Her nails dig into my chest as she humps like a machine cranked to 11. She's screaming like a banshee. It doesn't matter how thick these walls are, all dogs in a mile radius must hear her screeches of pain and pleasure. She bares her teeth, her mouth wide open. Sweat pours down her face as the veins in her temples bulge. This girl is coming as hard as anyone could come, yet I can't join her. I know that if I did, it would bring me the same agony and ecstasy.

Finally, her orgasm breaks. She begins to breathe again. She slows. But she does not stop.

I lay my head back and close my eyes. I take my hands off of her. Perhaps I just need to feel it--to look inside myself, find that damn, and smash it.

"Yeah," I say to her quietly, "gentle like that. Keep it going."

I begin to rock my pelvis, matching her tempo. My eyes have only been closed for a minute when a vision floods my mind. It's last March. I'm lying in a forest clearing. I look up and see the beauty of Chloe in the nude, her whole body rising and falling, rising and falling, content to gently, tranquilly ride me forever. Her hands explore her own body. Her face is pointed to the sky, elongating her pale, delicate neck. She grazes her obliques with her fingertips, grabs her breasts, plays with her hair.

Fuck! Why won't I come?!

I grab Jazlyn by the hips, raise them, and start thrusting up, pounding her from below.

"Oh, Jeez!" She squeals in surprise. "Oh- fuck! Oh- I- I- I don't- fuck!"

There is no more pleasure for me; all is agony. An agony that will end if I can just...I push her off of me and onto her back.

"If- if we could..." she mumbles, but I barely hear it. I shove my cock deep inside her and begin slamming into her with a fury.

She grabs my arms, holding them tight. She keeps screaming my name. Tears fall from her eyes.

I'm almost there. I can finally feel it approaching. My cock is a piston, pounding at maximum speed. I close my eyes again and see Chloe. She stares at me with a dark desire in her pale eyes.

Jazlyn begins tapping my chest with both hands.

"Stop!" she gasps. "Stop! I need to stop."

I pull out of her and climb off the bed. Jazlyn closes her legs and wraps her arms around her belly.

"I... I'm sorry," I tell her. "I- I forgot how... new to this you are. I got carried away. I-"

"No, no. It's OK. It's just... it was a lot..."

"I know. I'm sorry. I'm just gonna..."

I sulk into the bathroom, a coward too ashamed to look Jazlyn in the eye any longer.

My cock is still as solid as oak. It's hot to the touch. I place it atop the sink. The smooth porcelain surface is cold. A shiver runs up my spine, but it feels good, soothing.

I stare at myself in the mirror. Jazlyn's nail marks are still on my chest. Fuck, I hope they go away. Otherwise, Jen will be bound to notice. I can't spend the rest of my vacation with my shirt on.

After a minute, the old boy finally begins to relax, go limp, and shrink down. I clean myself up.

When I step back into the room, Jazlyn has already dressed herself.

"Headed out?" I ask.

"Yeah," she says. "I know they still won't be back for awhile, but better be safe than sorry. You know?"

"I hear you. Listen... if that was too much-"

"No, it's OK. Really. I- I- it wasn't too- I mean, it was. But that's OK! I'm just not... I wasn't... ready for it. But I want to be. I still remember the way I saw you giving it to Chloe on that couch. I want that, I do. It just will take some time..."

"Of course it will. Of course. I knew that before I... so, it's just- you can trust me. You can still trust me."

"I know. I do! I... I should get going."

"Right. See you at dinner."

"Yeah. Bye."

How bad did I just fuck up?

Thirty minutes later, Jazlyn's caution proves wise as Jen walks into the hotel room. Turns outs, she and Felix left the spa early, deciding to skip the 'sound bath,' whatever that is.

"Everything else, though," Jen purrs, "was exceptional."

She sits opposite me on the bed.

"Exceptional, huh? Why's that."

"Well, the sauna was lovely. And look at my nails!"

"Lovely. Orange has always been your color."

"But the best part," she tells me, her mouth slightly open in that sexy way I know so well, "was the massage."

"A good masseuse?"

"I mean, he wasn't the best masseuse I've ever had..."

"He?"

"...but he was certainly the best-looking."

"Oh really?"

"His name was Brevet."

"Oh, dear god."

"God, does that boy have muscles! And blue eyes! Oh, and the thickest head of hair I've ever seen."

"Sounds like a dream."

"Oh, he was."

"And you enjoyed being rubbed down by this dream man?"

"Very much."

"How much?"

"Oh, not too much. Don't worry, he didn't touch anything fun. He was very professional."

She gets on all fours and crawls to me, her lips inches from mine.

"But my fun bits certainly need touching."

My cock aches.

"I'm not feeling 100%," I tell her.

She stares at me with her alluring green and gold eyes.

"Really?! Well, what are you feeling? 80%? 70?"

"Oh, I don't know."

"You don't want to play with my fun bits at all?"

"Of course. I just--maybe I got too much sun. I just want to sit here for a while."

She reaches down and pulls my drawstring.

"Fine. You just sit there. I'm going to have my way with you while I think of Brevet and his strong hands."

I open my mouth to protest, but when she pulls my shorts down, my cock springs up firm and straight once more.

"He seems 100%," she says, amused.

"I really don't have to do anything?" I ask.

"Nope."

"I can keep browsing on my phone?"

"You can do whatever you want, so long as I can get to this dick."

12