Gigolo to the Stars

===DISCLAIMER===

This is a work of fiction, for entertainment purposes.

All characters depicted are over the age of 18.

This material should not be viewed by anyone under the age of 18 years of age.

Copyright YoungDubz 2024

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Chapter 6: Teaching Kiernan

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Jake opened his eyes and turned around but looked at the floor as he moved toward his client.

Jake wanted to take in every inch of his client before seeing who it was, so starting at her small feet clothed in a pair of long white socks, his eyes moved upwards, studying the long slender legs, socks going all the way up past her knees to her smooth thighs, the visible bare skin looking so soft. Continuing upwards, Jake saw a very short tartan skirt he estimated to be maybe 4-5 inches from waist to hem. Above that, his guest's slender tummy and abs exposed as a white shirt was tied just below the woman's small breasts and the buttons visible were undone, showing the white bra she was wearing.

Jake's gaze continued upwards, along the smooth skin of his client's neck to her face. He didn't recognise who he was looking at but she was definitely attractive. Finally, Jake looked and saw this woman's blonde hair was done up into two pigtails, one on either side of her head.

"Hi, it's Jake, right? I'm Kiernan, nice to meet you!" said Kiernan Shipka, a big smile on her face to match her bubbly demeanour.

"Hi, Kiernan, what would you like today?" Asked Jake.

Kiernan paused for a second, lowering her head and breathing deeply. When she looked up, her face had changed. Now sporting a look of innocence, she moved toward Jake and put a hand on his chest.

Kiernan looked at Jake in his eyes and said "I want you to teach me how to fuck, Daddy!"

Jake's eyes grew wide in surprise at the boldness of the young beautiful blonde. He hadn't expected any role play would be involved.

Kiernan pressed on.

"All the other girls at school are always talking about how they've all had sex with their boyfriends and I just want to fit in so I thought if I told them I'd had sex with someone older, then they'd be my friends. You want me to have friends at school, don't you daddy?" She asked in a childlike voice.

Jake paused for a moment, thinking of his character in this scenario, before looking directly into Kiernan's beautiful eyes.

"Of course I do, sweetheart, but it would be wrong." Said Jake, not wanting to directly bring up the topic of incest, but Kiernan's next sentence clarified the situation.

"Why would it be wrong? You're only my step-dad, and mommy doesn't have to know! She's away with work, it's just us two here!" Kiernan said with a wink and a giggle.

In character, Jake hesitated and thought it over before deciding to go with it.

"Sit with me on the couch, honey!" Said Jake, as he moved to the plush couch in the living room and sat down.

Kiernan followed and sat on the other end of the couch cross legged. Jake looked over and could see that she wasn't wearing any underwear and her bald pussy was on full display.

"So, sweetie, how much do you know about sex?" Jake asked.

"I know that when a boy really likes a girl, his penis gets really hard and he can put it inside the girl until he has an, um, ejaculation?" Said Kiernan, as if reciting a memorised section of a textbook.

"Do you have any experience with sex at all? I would hope not but have you seen a real live penis before?" Asked Jake.

"Never in person but one time at a sleepover, this girl brought over this magazine which had a lot of pictures of naked men and I looked through it and I felt myself get wet in my panties a little bit!" Said Kiernan, bashfully.

"That's good, that's normal. Would you like to see a real life penis?" Jake asked the petite blonde.

"Ooh, yes please, daddy!" Kiernan replied, smiling.

Jake stood up and moved to stand in front of Kiernan.

"Unzip my pants, sweetie and pull them down." Said Jake.

Kiernan followed Jake's request while Jake removed his shirt. His semi erect cock gave his boxers a very evident bulge that Kiernan looked at intently. She looked up at Jake.

"Can I take your boxers off too, daddy?" She asked.

"Sure thing, sweetheart," said Jake.

Kiernan pulled Jake's boxer shorts down by the waistband and his semi erect penis sprung up, nearly hitting Kiernan in the face. She looked at Jake's cock and moved her head around to study it from other angles.

"Wow, daddy. Your penis is so big!" She said in amazement.

"You can call it other things too, honey, like cock or dick." Said Jake.

Kiernan giggled. "I like cock." Said the blonde, the devilish look she gave Jake betraying her character.

"So what do these other girls in school talk about what they've done with their boyfriends!" Asked Jake.

"Well, they talk about having sex or fucking and some of them talk about giving handjobs and blowjobs, I think?" Said Kiernan.

"What do you think either of those involve?" Asked Jake.

"I guess a handjob is just rubbing it with my hand, like this?" Replied Kiernan, as she placed her palm against the top of Jake's penis and rubbed her hand up and down the length of it.

Kiernan's hand felt so soft against his cock and Jake closed his eyes as a rush of pleasure surged through him.

"Mmm, that's pretty close sweetie, but what the girl actually does is put their hand around the cock, like a water bottle and then move their hand up and down." Said Jake.

"Like this, daddy?" Kiernan asked, as she wrapped her small hand around Jake's cock and started to jerk him off as her pretty face looked up at him.

"Oh god, yes, just like that baby!" Groaned Jake, feeling his cock get harder in Kiernan's hand.

"What if I use both hands, daddy?" Said Kiernan, her other hand also wrapping around Jake's cock, both hands moving slowly up and down the shaft.

"Fuck, that's even better!" Moaned Jake. "So this is a handjob, you seem to have this down. Do you know what a blowjob is?"

"Is that just blowing on it, like this?" Said Kiernan as she pursed her lips and blew cool air onto Jake's cock.

"Oh god, that feels incredible but no. No, a blowjob is when a girl puts a boy's cock into her mouth. Why don't you give it a try?" Said Jake, his hand running across Kiernan's hair.

"Okay daddy, whatever you say!" Said Kiernan with a smile.

Kiernan opened her mouth and took the swollen head of Jake's member inside, closing her lips around it.

"Oh fuck!" Moaned Jake, as Kiernan's warm mouth engulfed the head of his cock. "Keep using your hands too, baby!"

Kiernan followed the instructions to the letter, moving both hands up and down Jake's cock as she sucked on the engorged head.

Jake's hands moved to the back of Kiernan's head and he started to slowly thrust his hips to push his cock further into the petite blonde's mouth.

Kiernan's lips were soon halfway along Jake's shaft and the gorgeous young actress began to gag as the hard member started to rhythmically move in and out of her throat.

Jake removed his cock from Kiernan's mouth as she started gagging. Kiernan gasped for breath and let a large amount of saliva drip from her mouth.

"Sorry baby, daddy got a little carried away, maybe a bit too much for your first time!" Said Jake, staying in character while his real life intuition said the pretty young blonde kneeling before him was no stranger to throating a large cock.

"Nooo, I liked it, daddy! Mmm, I felt my little pussy getting wetter and wetter as you pushed more and more of your hard cock into my mouth. Do you want to see?" Kiernan asked.

"Of course, baby!" Replied Jake.

Kiernan turned and lay back on the couch. Taking hold of the hem of her extremely short skirt, Kiernan pulled the clothing up and revealed her pussy to Jake.

Jake's eyes were drawn immediately to the bald mound between the young blonde's smooth, slender legs. Kiernan's pussy was plumper than Jake expected and it glistened with the blonde's juices.

"God, such a perfect little pussy." Said Jake, placing his hand on Kiernan's firm abs and moving it down to her pussy. "Would you like me to touch your pussy, baby?"

"Mmm, yes please, daddy!" Whimpered Kiernan before moaning as Jake's fingers ran over her clit and along her juicy pussy lips.

Pleasure coursed through Kiernan as Jake's fingers softly rubbed her pussy.

Kiernan closed her eyes and a series of slow moans escaped her slightly agape mouth.

"Yesss, daddy. Touch your step-daughter's pretty little pussy! God, let me suck your hard cock again while you rub my pussy, please!" Moaned Kiernan, her hand moving up to rub against Jake's cock.

Jake paused, then lifted Kiernan up from the couch. He turned around and sat down, then lay back on the couch. He manipulated Kiernan's body until her face was aligned with his cock while the blonde's toned little ass and dripping plump pussy were in front of Jake.

"Now, honey, this is called a sixty-nine. Remember, it's not just the man who needs to be warmed up before sex, the woman needs to be ready too." Said Jake, as he gazed in wonder at Kiernan's pink pussy and firm ass inches from his face.

Jake extended his tongue and leaned in to get his first taste of Kiernan, the blonde's sweet nectar immediately intoxicating him.

"Oooh, daddy! Is that your tongue? Mmm, it feels so good how you're licking me! I want to make you feel good too!" Moaned Kiernan, lowering her head and taking Jake's cock back into her mouth.

Wanting to reward Jake for playing his role so well and in response to how good he was making her pussy feel with his tongue, Kiernan dropped character and after timidly sucking on the head of Jake's cock, she took a deep breath in through her nose and lowered her mouth all the way down Jake's shaft.

"Shit!" Groaned Jake, tearing himself away from Kiernan's dripping pussy as he felt his cock enveloped in the young blonde's snug mouth and throat. He brought his fingers to Kiernan's pussy to replace his tongue.

Kiernan made herself weep, her eyes filling with tears as she let her mouth fill with saliva. She wanted to replicate for Jake how she looked the first time she'd deep throated a cock. To add to the pretence, Kiernan made exaggerated gagging sounds despite Jake's cock resting comfortably in her throat.

Stepping back into character, she quickly moved her head back up off Jake's cock. Strands of saliva hung from her mouth and clung to the erect shaft and Kiernan looked back at Jake while her hand fondled her scrotum.

"I'm sorry, daddy. Your cock just looked so yummy and with how good it felt earlier I just had to try and take it all. Did it feel good, daddy?" Asked Kiernan with a giggle and groan of pleasure as Jake's fingers tickled her tender clit.

"It felt incredible, baby!" Moaned Jake.

"Yay, I'm so glad you liked it, daddy!" Squealed Kiernan before she lowered her head back down onto Jake's cock.

The blonde bounced her head on Jake's shaft, sloppily coating his hard cock with her saliva. In return, Jake returned his mouth to Kiernan's pussy, lashing his tongue against the petite actress's clit.

The pair stayed in this position for a few minutes, orally pleasuring one another until Kiernan felt the initial surges of her orgasm start to build.

"Fuck daddy, feels so good! God, keeping licking me, daddy! Keep licking your little girl's plump little pussy!" Moaned Kiernan, lifting her head from Jake's cock and substituting her hand for her mouth, stroking the slick shaft up and down slowly.

Wanting to push Kiernan over the edge into her orgasm, Jake brought two fingers to her pussy and pushed them inside her pink hole, curling them downwards as they entered to rub her g-spot.

"Fuuuck, yes Daddy! Finger my little pussy! Make me cum, Daddy! Make your little girl cum all over your fucking fingers! Ohhh shit, I'm cumming!" Moaned Kiernan, as her orgasm hit.

The blonde's petite body shook as waves of ecstasy ran through her. She had been holding herself up with one arm and as she came, she moved her arm to her ass.

Kiernan's front half collapsed onto Jake, her covered breasts pressing into his stomach as her pretty young face came to rest on Jake's thigh besides his stiff cock. In between moans, Kiernan softly kissed the swollen member while at the other end of her body, she spread her ass cheeks to allow Jake to see her little pink asshole pulsating as she came.

Kiernan's orgasm soon passed, and the lithe blonde stood up off the couch and stood before Jake, who sat up on the couch.

"Daddy, that was amazing, but I need more!" Purred Kiernan.

With Jake now in a seated position, Kiernan straddled him, putting one smooth leg on either side of Jake's hips.

She positioned herself above Jake so her dripping pussy was mere centimetres above Jake's hard cock, close enough that he could feel the heat emanating from the blonde's pussy.

Jake placed his hands on Kiernan's hips and ran them up her firm young body.

Upon reaching the blonde's white shirt, Jake untied the knot situated just below Kiernan's perky breasts and undid the one button remaining.

Kiernan removed her shirt, letting it fall to the ground behind her and then she moved her hands to the front clasp of her bra.

The blonde unclasped her one item of underwear and shifted her arms to let it also fall from her body to the ground.

Jake stared at the blonde's perky little breasts with a fever of lust before bringing his mouth to one of Kiernan's hard pink nipples and sucked on it, his hand moving up to pinch the blonde's other nipple.

As Jake paid expert attention to her breasts, Kiernan's hand reached down and held Jake's cock and lowered herself down, her pussy lips parting to allow entry to the hard shaft.

Kiernan and Jake moaned in unison at this initial penetration and their eyes met. As the pair gazed deep into each other's eyes, Kiernan began to slowly lower herself down onto Jake's cock. The blonde's eyes widened and her mouth gaped open as her pussy was filled by Jake's long, hard cock.

"Ohhh fuuuck! Fuck, you're so big, Daddy! God, your huge cock is filling my little pussy so fucking good!" Whimpered Kiernan as her pussy reached the bottom of Jake's shaft.

"Mmm, you're so tight, baby!" Groaned Jake, as Kiernan slowly started to bounce her slim body up and down on his cock.

Jake's hands moved down to Kiernan's hips and around to her ass beneath her skirt, one firm cheek in each hand.

As his fingers firmly kneaded the soft flesh of the young blonde's impeccable butt, Jake started thrusting his hips upwards in time with Kiernan's movements.

"Yes! Fuck me, Daddy! Fuck my sweet little pussy with your big cock! Mmm, I've seen you looking at me when I'm by the pool, sunbathing in a bikini. Trying to hide how hard my tight little body makes your cock! You've wanted me, haven't you Daddy because I've wanted you. Why do you think I'm always walking around in booty shorts and crop tops? I've wanted you to fuck me for so long! Fuck me! Fuck me so hard no other man will compare! Make me a slut for my stepdaddy's dick! Fuck, you're so deep in my tight little cunt and it feels so fucking good!" Moaned Kiernan, throwing her head back and letting out a guttural moan as Jake's cock pushed deeper inside her than almost any man had before.

"Language, young lady!" Groaned Jake, through gritted teeth. Kiernan's words in combination with how incredibly her pussy was squeezing his cock were bringing Jake to the edge.

"You gonna punish me for saying such dirty things, Daddy?" Said Kiernan, her hands caressing Jake's chest as she looked down at him.

In one movement, Jake put his arm across Kiernan's back and whilst remaining inside the blonde, Jake pulled Kiernan down so she was lying on the couch.

Jake put one of Kiernan's legs on each shoulder and lowered himself so the blonde's knees were at her chest and the pair were face to face.

In this new position, Jake started to rapidly thrust himself in and out of Kiernan, his thighs slapping rhythmically against the blonde's ass.

Jake looked down at Kiernan, the blonde's pretty face a mask of pleasure with her eyes closed and mouth wide open as she gasped with each inward thrust he made,

Kiernan's gasps and moans got closer and louder as her second orgasm approached.

"Yesss Daddy, keep fucking me! Mmm, you're gonna make me cum again, all over that beautiful big daddy dick! Will you cum with me, Daddy?" Kiernan groaned as she ran a hand down her rock hard stomach and brushed her fingers against her swollen clit.

"I'm close too, tell me where you want it sweetie!" Moaned Jake, quickening the pace of his thrusts even more.

"Mmm, I want it inside me. I know it's wrong, but I want to feel Daddy's hot load dripping out of me as I walk back to school. Will you do it, Daddy? Will you please cum inside me? I want it so bad! I want to be claimed by your hot cum, Daddy!" Squealed Kiernan, her orgasm closing in.

The way Kiernan's pussy squeezed his cock in combination with the dirty talk erupting from the blonde's mouth brought Jake to his brink.

"Fuuuck, I'm gonna cum, baby!" Jake grunted.

Jake thrust in and out of Kiernan a few more times before plunging himself deep into the young actress and letting his cum shoot inside her.

"Ohhh, I feel it, Daddy! I can feel your hot cum inside meee!" Screamed Kiernan as she frantically rubbed her clit and her orgasm hit.

Kiernan's pussy got tighter as she came, her sex practically squeezing every last drop of cum from Jake.

Once he was spent, Jake kept his quickly softening cock inside Kiernan as her own orgasm shortly subsided, then pulled out.

On his knees on the couch, Jake looked down at Kiernan. The gorgeous blonde looked absolutely ravishing. Her pigtails were messy and her face and those small but perfectly formed breasts were glistening with a thin sheen of sweat.

His eyes roaming further downward to Kiernan's pussy, the plump lips were slightly open and Jake could see his cum slowly seeping out.

"Admiring your handiwork?" Asked Kiernan, sleepily.

"Just a little. How are you doing, baby girl?" Jake asked.

"Please, call me Kiki." Said Kiernan, lifting herself to a seated position before standing and moving to a rucksack nearby Jake hadn't previously noticed.

Jake watched as Kiernan opened the bag and took out some alternative clothes.

He watched Kiernan remove her skirt and put on a pair of pink panties before his attention was diverted by the ringing of his phone.

Jake rummaged in his own discarded clothes and found his phone, alerting him to an incoming FaceTime call from Aubrey. He walked into another room and answered.

"Hey!" Said Jake, immediately noticing that Aubrey's face was flushed.

"Just to, oh, let you know that, mmm, there's a bit of a delay with your next client, there's uh traffic or, or something." Said Aubrey, evidently unfocused.

"No worries, just finishing up here and I'll wait for them. Are you okay? You seem a little not with it right now?" Said Jake, having an inkling what Aubrey was doing.

He was soon proven wrong as Aubrey turned her camera around. Jake had assumed that Aubrey was masturbating but he soon saw much more interesting.

Between Aubrey's legs, Jake could see the red hair and striking eyes he recognised from somewhere.

"Good girl, Sadie, such a good girl eating Mommy's pussy so well! Say hi to Jake, Sadie!" Said Aubrey.

The full face of the redhead on the phone came into view and Jake recognised the gorgeous actress from Stranger Things.

"Hi Jake!" Said Sadie Sink before returning to her task of licking Aubrey.

"Mmm, make me cum, Sadie! Make me cum and maybe I'll give you a discount for a couple of hours with Jake and that wonderfully large cock of his." Moaned Aubrey.

"You're having fun, I see!" Chuckled Jake.

"Someone has to keep these youngsters in line! Anyway, I'll check in later, see ya!" said Aubrey, hanging up the phone.