Escort to Celebrities Chapter 6
Jake's eyes fluttered open as he turned to face his client. Curiosity drew him closer to her, starting at her delicate feet, wearing a pair of long, white socks. He studied her long, slender legs, the socks extending up past her knees, revealing soft, smooth thighs. He allowed his gaze to travel higher, taking in the sight of her tiny skirt, mere inches from her waist to its hem. Abruptly, his attention turned to the tickling peeks of abs as her shirt was tied only just below her small breasts, teasingly showing off a white bra.
His eyes followed the curve of her neck and finally fixed on her face. Though he didn't recognize her, she was undoubtedly gorgeous. Her blonde hair was fashioned into two pigtails on either side of her head.
"Hi, it's Jake, right? I'm Kiernan," exclaimed Kiernan, beaming with enthusiasm.
"Hi, Kiernan. What do you need today?" enquired Jake.
Kiernan considered her words thoughtfully, tied in knots, and then released them just as swiftly. Moving toward Jake, her hand found its way to his chest.
A mischievous look flickered in Kiernan's eyes as she challenged, "I want you to teach me how to have sex, Daddy!"
Jake couldn't help the sudden surprise at Kiernan's assertiveness. His mind had prepared for a different kind of role play.
Kiernan continued without missing a beat.
"All the other girls at school are talking about how they've had sex with their boyfriends, and I want to fit in, so I thought if I told them I'd had sex with someone older, then they'd be my friends. Don't you want me to have friends at school, daddy?" her eyes twinkled as she spoke in a childlike tone.
Jake paused a moment, evaluating how to play this situation.
"Of course I do, sweetheart, but it's wrong." Jake commented, hesitatingly, not wanting to bring up the issue of incest. However, Kiernan's next statement cleared the situation.
"But you're not really my dad, just my stepdad, and Mommy's away with work. There's just the two of us here." Kiernan explained with a wink, further challenging Jake's character.
With a sigh, Jake figured he'd play along.
"Sit with me on the couch, honey," Jake said, making his way to the plush couch in the living room.
Kiernan followed suit and sat cross-legged on the opposite end of the couch. Jake looked over and saw no underwear on Kiernan, her bald pussy on full display.
"So, sweetie, how much do you know about sex?" asked Jake.
"I know that when a guy really likes a girl, his penis gets really hard and he can put it inside the girl until he has an orgasm." Said Kiernan matter-of-factly.
"Do you have any experience with sex or have you just seen pictures?" asked Jake.
"I did once see a magazine with pictures of naked men at a sleepover, and I felt myself get a little wet in my panties." Kiernan admitted sheepishly.
"That's normal. Would you like to see a real, live penis?" asked Jake.
"Yes, please, daddy!" Kiernan almost purred.
Jake stepped forward and removed his shirt, presenting his slight erection to his stepsister.
"Do you want me to take off my boxers as well?" Kiernan asked.
"Of course, sweetheart," agreed Jake.
Kiernan did as she was told, dragging down Jake's boxers by the waistband until his semi-erect cock bounced forward, almost hitting Kiernan in the face. She took in the sight of his penis, looking it over from different angles.
"Wow, daddy. Your penis is huge!" Kiernan exclaimed in wonder.
"You can call it other names, too, like cock or dick." Jake offered.
Kiernan giggled cheekily. "I like cock." She declared boldly.
"Hmm, what do the girls at school talk about their sexual experiences with their partners?" questioned Jake.
"They chat about doing the deed or screwing, a few of them even discuss giving blowjobs and handjobs," responded Kiernan.
"Could you explain what these body actions imply?" Jake enquired.
"I assume a handjob is just brushing it with my hands, like this?" asked Kiernan, as she placed her hand on the top of Jake's penis and glided it down the length of his erection.
Kiernan's hand felt soft on Jake's member, pressing gently as a pleasurable sensation surged through his body.
"Well, a handjob is when someone wraps their hand around the cock, just like a bottle and then moves their hand up and down," explained Jake.
"Like this, dad?" queried Kiernan, as she grabbed Jake's member with one hand and began to jerk him off while looking up at him with her pretty eyes.
"F*** yeah, that's absolutely right, little one!" groaned Jake, feeling his hardness grow.
"And what if I use both hands, dad?" asked Kiernan, her other hand also groping Jake's cock, both hands now moving up and down the shaft.
"Holy sh*t, that's even better!" moaned Jake. "So, you're genuinely proficient at performing handjobs. Do you know what a blowjob entails?"
"Is it just blowing on it, like this?" summarized Kiernan, puckering her lips and blowing air onto Jake's mean member.
"Wow, that certainly feels fantastic, however, it's not quite it. A blowjob is when a girl inserts a guy's manhood into her mouth. Let's give it a whirl," suggested Jake, playing along as his real-life insights hinted that the petite blonde kneeling before him had undoubtedly received a large-sized rod before.
"Sure thing, pops!" beamed Kiernan with a smile.
Lauren opened her mouth and engulfed the head of Jake's erection, her lips enveloping it.
"Holy sh*t! That's intense!" groaned Jake, as Kiernan's warm mouth enveloped the head of his cock. "Don't forget to keep going with your hands too, sweetie."
Kiernan followed suit, moving both hands up and down Jake's cock at the same time as sucking his manhood.
Jake's fingers maneuvered to the back of Kiernan's head, spreading her golden locks as he started to thrust his hips, pushing his dick deeper into her throat.
Jake observed Kiernan's face go red as a series of loud gagging sounds emanated from her throat and moisture dripped from her mouth.
"Sorry darling, I must have gone a bit too far, probably not ideal for your first attempt," said Jake, adhering to his character while a sense of realization dawned on him that the young, slender actress kneeling before him was anything but inexperienced with throating a large dick.
"Nooo, I loved it! And I felt my little pussy getting all the more aroused as you slid more of your hard manhood into my mouth. Can I show you now?" enquired Kiernan.
"Certainly, my darling," conceded Jake.
Kiernan rolled onto the lounge, lifting up her mini-skirt to unveil her pussy.
Jake's eyes immediately fixed on the bald mound between Kiernan's toned legs. Her pink pussy glistened with her smooth womanly juices.
"Such a marvelous little pussy," commented Jake, his hand trailing down Kiernan's firm tummy to land on her dewy pussy lips. "Would you prefer me to fondle your pussy, darling?"
"Mmm, yeah please, dad!" yelped Kiernan, moaning as Jake's fingers circled her clit.
Kiernan sighed in pleasure, her head rolling back slightly as Jake's fingertips roamed along her pussy lips.
"Mm, yes, dad. Allow me to cover your manhood with my lips while you caress my pretty pussy, please!" whimpered Kiernan, her hands reaching down to stroke Jake's penis.
Jake halted for a moment, considering this and then guided Kiernan's body until her face was once more fighting for breath. Her pert buttocks and drooling vagina stared at him as he slouched back on the lounge.
"Now, my darling, this is called a 'sixty-nine.' Remember, it's essential for both partners to be prepared for sex, not just the gentleman," reasoned Jake, his eyes glued to Kiernan's pink pussy and firm ass.
Jake stretched his tongue and moved in to have his first taste of Kiernan's juicy vagina; the blonde's sweet fluid sent a thrill through his mind.
Oh my gosh, is that your tongue? It feels so good how you're licking me! I want to make you feel good too." Exclaimed Kiernan, bending over and taking Jake's penis back into her mouth.
Desiring to compensate for Jake's outstanding performance and the fantastic sensation he was creating in her pussy using his tongue, Kiernan set aside her persona and after modestly sucking on the head of Jake's dick, she inhaled a deep breath. Afterwards, she positioned her mouth over Jake's shaft.
"Shit!" Shouted Jake, disengaging from Kiernan's wet pussy as he noticed his cock encased in Kiernan's snug mouth and throat. He touched Kiernan's pussy with his fingers.
Kiernan made herself cry, her eyes brimming with tears as she filled her throat with saliva. Focusing on imitating how she seemed the very first time she had deep-throated a cock, Kiernan made exaggerated retching sounds despite Jake's erection comfortably residing in her throat.
Back to her character, she quickly freed her mouth from Jake's penis. Strands of saliva clung to her mouth and the erect shaft. Kiernan gazed at Jake while her hand caressed her scrotum.
"I'm sorry, daddy. Your cock just appeared so delectable, and because of how well it was making me feel in my pussy before, I just had to attempt to take it all in. Did it feel nice, daddy?" Asked Kiernan with a chuckle and a pleasure cry as Jake's fingers touched her hyper-sensitive clit.
"It was sensational, my child!" Moaned Jake.
"Wow, I'm so thrilled you enjoyed it, daddy!" Chirped Kiernan as she dipped back down onto Jake's dick.
The blonde bobbed her head on Jake's penis, espousing her saliva over his stiff member. In retaliation, Jake resumed his attention to Kiernan's pussy, lashing his tongue against her clit.
The pair stayed in this position for several minutes, engaging in a mutual oral exchange until Kiernan sensed the beginning of her orgasm.
"Fuck daddy, it feels so good! Oh my God, keep licking me, daddy! Keep licking your little girl's full and juicy pussy!" Screamed Kiernan, pulling her head off Jake's cock and utilising her hand to replace her mouth, stroking the slick penis up and down gradually.
Wishing to induce Kiernan to climax, Jake turned his fingers towards her vagina and inserted them inside her pink opening, curling them downwards as they entered to stimulate her g-spot.
"Fuuuck, yes Daddy! Fingertip my little pussy! Make me climax, Daddy! Make your little girl squirt all over your fingers! Ohhh damn, I'm cumming!" Screamed Kiernan, experiencing orgasmic shudders.
Kiernan's slight frame trembled as shards of rapture exploded through her. She'd been supporting herself on one arm, but as she came, she removed her hand and landed on Jake, her boobs pressing against his stomach. Her pretty, young face toppled onto Jake's leg next to his unyielding cock.
Kiernan's climax diminished, and the slender blonde stood up from the couch and stood before Jake, who had returned to a sitting position.
"Daddy, that was remarkable, but I require more!" Hissed Kiernan.
With Jake now sitting with his legs spread wide, Kiernan straddled him, positioning one smooth leg on either side of his hips.
She adjusted herself over Jake so that her lubricated cunt was only millimetres above Jake's cock, near enough that he could sense the heat oozing from Kiernan's pussy.
Jake placed his hands on Kiernan's hips and ran them up her lithe body. Upon reaching the blonde's white shirt, Jake undid the plait below Kiernan's generous tits and de-buttoned the solitary button remaining.
Kiernan eliminated her shirt, allowing it to fall behind her. She then manipulated her hands to disconnect the clasp on her bra.
The blonde removed her undergarment, enabling it to join her shirt on the floor.
Jake starred at Kiernan's firm, youthful breasts with unabated ardour. He lowered his mouth to her erect nipple and suckled on it, concurrently pinching the other nipple in his hand.
As Jake administered expert attention to her teats, Kiernan's hand veered towards her belly and supported Jake's cock. She eased herself down, her pussy lips parting to enable Jake's formidable dick to penetrate inside her.
Kiernan and Jake moaned in synchrony on penetration and looked into each other's eyes. As the duo locked eyes, Kiernan began to descend further onto Jake's penis. The blonde's eyeballs widened and her gaping mouth exposed as her pussy was filled by Jake's lengthy, hard penis.
Ugh, fuck me! Damn, you're so large, Daddy! Lord, your gigantic cock fills my little pussy so nicely! Kiernan moaned as her pussy reached the base of Jake's dick.
"Mmm, you're so tight, sweetheart!" Groaned Jake as Kiernan slowly began to bounce her petite body up and down on his dick.
Jake's fingers moved down to Kiernan's hips and shifted to her ass beneath her skirt, one rounded cheek in each hand.
As his fingers firmly squeezed the soft flesh of the young blonde's immaculate butt, Jake began thrusting his hips up with each of Kiernan's movements.
"Yes! Fuck me, Daddy! Fuck my tiny pussy with your big cock! Mmm, I've seen you watching me when I'm by the pool, sunbathing in a bathing suit. Attempting to hide how hard my tight little body makes your cock! You've wanted me, haven't you, Daddy? Because I've wanted you too. Why do you think I always walk around in shorts and crop tops? I've wanted you to fuck me for so long! Fuck me! Fuck me so vigorously that no other man can compare! Make me a slut for my stepfather's cock! Ugh, you're so far in my tiny cunt and it feels so fucking incredible!" Kiernan moaned, tossing her head back and letting out a gut-wrenching moan as Jake's cock pushed deeper inside her than almost anyone else ever had.
"Language, young lady!" Groaned Jake through clenched teeth. Kiernan's words, combined with how severely her pussy was squeezing his dick, were driving Jake to the edge.
"You gonna discipline me for saying such filthy things, Daddy?" Asked Kiernan, her hands running along Jake's chest as she stared into his eyes.
In one fluid motion, Jake placed his arm across Kiernan's back and, while he was still inside her, gently lowered her down onto the couch.
Jake put one of Kiernan's legs on each of his shoulders and shifted himself so her knees were near her chest, ending up with Kiernan and Jake face-to-face.
In this novel position, Jake began rapidly thrusting himself in and out of Kiernan, his thighs slapping rhythmically against her ass.
Jake gazed into Kiernan's eyes, the stunning woman's pretty face an expression of pure pleasure with her eyes shut and mouth wide open as she gasped with each inward thrust he made.
As Kiernan's gasps and moans drew closer and more intense, her second orgasm was approaching.
"Yes Daddy, keep fucking me! Ohh, you're going to make me cum again, all over that wonderful father figure dick! Will you cum with me, Daddy?" Kiernan groaned as she rubbed her hand down her hard stomach and touched her swollen clit.
"I'm near, baby. Tell me where you want it, sweetie!" Moaned Jake, driving his thrusts even faster.
"Mmm, I need you to come inside me. I know it's wrong, but I want to feel Daddy's hot semen dripping out of me as I return to school. Will you do it, Daddy? Will you please cum inside me? I want to experience your glowing content so badly!" Screamed Kiernan, nearing her orgasm.
The way Kiernan's pussy squeezed Jake's dick, along with her dirty speech, pushed him over the edge.
"Ugh, I'm going to cum, baby!" Jake grunted.
Jake quickly thrust into Kierenna a few more times before embedding himself deep into her and let his sperm pour into her.
"Ohh, I feel it, Daddy!" Screamed Kiernan as she hurriedly rubbed her clit and her orgasm arrived.
Kiernan's pussy tightened as she came, her vagina virtually forcing all of Jake's sperm out.
When he was done, Jake retained his quickly softening dick inside Kiernan, who calmly slipped back into the possition and donned her shoes.
Jake looked at Kiernan, who was a vision of beauty. Her pigtails were disheveled, her face and those small but flawless breasts were slightly sweaty.
His gaze traveled further down to her pussy, the engorged lips were barely open and Jake could discern his cum slowly oozing out.
"Appreciating your work?" Inquired Kiernan, half-asleep.
"Just a bit, honey. How are you?" Inquired Jake.
"Just call me Kiki." Said Kiernan, standing and fetching a backpack in the room that Jake had not previously noticed.
Jake watched as Kiernan removed her skirt and wore a pair of pink underwear.
His attention shifted to the ringing of his phone. He dug through his shed clothes and found it, responding to an incoming Facetime call from Aubrey. Jake walked into another room and answered.
"Hello!" Said Jake, noting that Aubrey's expression was flushed.
"Hey, so I want to let you know that your next client has a bit of a hold-up, like some traffic or something," Aubrey said in a daze.
"No problem, I'll just finish up and wait for them. Are you OK? You seem a bit off," said Jake, sensing what Aubrey might be doing.
When Aubrey turned her camera around, Jake assumed she was masturbating but what he saw was much more intriguing.
Between Aubrey's legs, Jake could see red hair and striking eyes that he recognized from somewhere.
"Good job, Sadie, such a good job eating Mommy's pussy so well! Say hi to Jake, Sadie!" Aubrey said.
The full face of the redhead on the phone came into view and Jake recognized the beautiful actress from Stranger Things.
"Hi, Jake!" Sadie Sink said before going back to licking Aubrey.
"Feed me your pussy, Sadie! Make me cum and maybe I'll give you a discount for a few hours with Jake and his wonderfully large cock," Aubrey moaned.
"You're enjoying yourself, huh?" Jake chuckled.
"Someone has to keep these youngsters in line! Anyway, I'll check in later, see you later," said Aubrey, hanging up the phone.
Jake walked nude back to the living room and saw Kiernan standing near the front door.
"I thought it was rude to just leave," she said, opening the door.
"Thanks for the courtesy," Jake said, smiling.
"You were great. You should do improv, you're really good at it!" Kiernan said.
"Good for you too," Jake laughed.
"Maybe next time it won't just be a two-person scene. Bye!" Kiernan said as she exited with a wave.
Jake closed the door and laughed more to himself.
He headed for the bathroom and turned on the shower, stepping into the hot spraying water.
Jake stood for a brief moment with his eyes closed, letting the water wash over him as he thought about how much his life had changed in such a short time. A week ago, he'd taken a job in New York that led him to LA. He'd had sex with women he'd never thought he'd be with and might make more money in the next few days than he ever had before.
Jake got so caught up in how he got here that he didn't hear the bathroom door open and someone entering the shower behind him.
His first awareness of someone else with him was a hand reaching around his body to grip his cock and start stroking him.
His eyes shot open and he turned around to see Kiernan before him, also naked.
"Did you leave?" Jake asked, before Kiernan put a finger on his lips.
"Don't talk!" she said quietly.
She rubbed Jake's cock until it was hard, then turned around. Holding onto a nearby shower rail with her free hand, she guided Jake's erect cock between her slender ass cheeks and positioned his head at her ass.
"I got down to my car on the street and realized I needed more," Kiernan said, pushing back and letting Jake's cock slide into her ass.
"Oh shit, that hurts! Fuck my virgin ass, Jake. Yes, take my anal cherry! I love a big cock in my mouth or my wet little pussy, but never had a cock in my ass before! All those guys with their big cocks wanted it, but I always told them maybe next time and then ghosted them," said Kiernan, wincing as Jake's cock slid into her previously untouched hole.
As the hot water of the shower rained down on their naked bodies, Jake held Kiernan's hips with one hand and was slowly thrusting into her ass.
Jake knew from experience that water wasn't the best lubricant and while she said she liked the pain, Jake didn't want to injure Kiernan. Looking around, he saw a bottle of lotion on a nearby shower shelf.
He reached up and took the bottle, opened it, and squirted a generous amount onto his cock, then dropped the bottle and started rubbing the lotion onto his cock and around Kiernan's ass.
Even with the added lubrication, Kiernan's ass still gave some resistance to Jake's cock.
Holding Kiernan's hip with one hand, Jake slid his other hand to the front of her blonde, and let his fingers glide across her clit.
"Chill out and take it easy." He instructed Kiernan, who gazed back at him through watery eyes. The beautiful young blonde nodded her head in agreement and obeyed as instructed.
Kiernan took a deep breath and let out a long exhale as Jake kept thrusting, maintaining a slow pace. Eventually, his legs were pressed against Kiernan's lower body.
"Holy shit! Fuck, you're all the way in my butt!" Kiernan cried out.
Jake stared down at the young woman's round ass cheeks, pressed against his pelvis.
"I'm just going to stay like this for a bit, give you time to adjust. Cool with that?" He asked Kiernan.
She nodded in response.
The couple remained still for a minute or so, and then Kiernan looked back up at Jake and gave another affirmative nod.
"I'm ready now." She stated softly.
Jake started to pull his cock from Kiernan's bum gradually, then stopped when just the tip of his cock was still within her.
He thrust back in with more force, burying himself deep within her tight bum.
Kiernan uttered softly through gritted teeth, the mingling sensations of pleasure and discomfort overwhelming her.
Jake's thrusting became more intense with each pump, assisted by the grip on her hips for stability. Kiernan took over the stimulation of her pussy.
Her fingers glided over her seemingly insatiable pussy, which kept becoming wetter by the second. Two fingers slid into her pussy, creating a wet trail.
The blissful wave that washed over Kiernan erased any discomfort resulting from her backdoor being penetrated, leaving just pleasure behind.
"Yes! Yesss! Holy cow, it's a miracle! If I knew this felt this good, I'd have given up my virginity to a man long ago! You like it, Jake? You like fucking my ass?" Kiernan cried.
"Damn! This ass is unreal. So tight and squishy!" Jake gasped in a hushed tone.
Jake used his hands to spread the young girl's shapely bum cheeks, revealing a gaping hole. Then, he removed his cock, leaving her penetrated bum exposed.
He gazed in awe for a few seconds before plunging his cock into her once more, groaning as her tight hole contracted around it.
"Mmm, spread me, Jake! Make me gape like a nasty slut!" Kiernan begged. "Fuck me hard! Pound my ass while I play with my cunt! Fuck, I'm about to cum so hard!" Kiernan made her plea.
"Is that what you want? To be a slut? More of a slut than just surrendering to a stranger and having your pussy fucked? Cum for me, Kiernan, show me how slutty you can be!" Jake exclaimed and his thighs began slapping against Kiernan's bum as he kept thrusting.
The thought of what Jake meant by these words, along with the intense finger stimulation and anal penetration, created a powerful orgasm within Kiernan.
"Ah! Fuck, yes! Yes, I'm cumming!" She screamed.
With her bum gripping Jake's cock tightly, he kept thrusting as her orgasm subsided.
Finally, he held Kiernan up, dismounted and spun her around in the shower.
"On your knees!" Jake commanded, pushing down on Kiernan's shoulders.
Kiernan obeyed, pressing her knees into the hard tile as she bent over.
Jake gripped her blonde tresses and guided his cock into her mouth.
Kiernan took Jake's entire length into her mouth and throat, savoring the taste of her ass on his member.
Jake captivated her hair and began facefucking the pretty young brunette.
He wasn't able to last very long, as the desire to climax was getting stronger by the second.
Right before he came, Jake pulled his cock from her mouth and turned it upright, aiming it at her lovely face and chest.
Jake's cum erupted from his cock and covered Kiernan's face and chest. Once his orgasm subsided, he placed the head of his cock into her mouth and urged her to suck the remaining semen off his tip.
Kiernan stood and wiped off the cum with her fingers, tasting it as she cleaned herself. After cleaning up in the shower, the duo clothed and left the bathroom.
They strolled naked through their living room. "Holy shit, Kiernan! That was incredible!" she exclaimed, smiling brightly. "I'm going to tell all my friends about you!" \
"No need to shout about it from the rooftops, Kiernan." Jake laughed.
"Listen up, I've got plenty of friends in this business who'd relish being treated like you just treated me," Kiernan stated with a wicked grin. "Heck, I might even join them if they come to visit you."
"I'm looking forward to it!" Jake exclaimed, a smile on his face.
"I have to go, I've already been late enough," Kiernan replied, glancing at her phone.
She hurriedly moved to Jake and wrapped her arms around him, sharing a deep, passionate kiss. They exchanged tongues briefly before parting ways.
"Bye Jake!" Kiernan called out as she hastily made her way to the door and left.
Jake made his way to the pool, removed his shirt, and jumped in.
He swam back and forth for approximately ten minutes before hearing the doorbell chime.
He climbed out of the pool, walked to the front door, and opened it up.
His eyes widened at the sight of the brunette woman standing before him. "Hello, Jake?" she began. "I'm..."
"Winona Ryder," Jake interrupted, awestruck.
