Caught in Charlotte's Web
Copyright© 2025 by Milly Mills
Chapter 2 A night with Sophie
Drama Sex Story: Chapter 2 A night with Sophie - Leo, a 32-year-old man meets a young blonde girl on a flight to Sydney. Things soon get complicated as he learns more and more about this beautiful stranger.
Caution: This Drama Sex Story contains strong sexual content, including Ma/Fa Ma/ft Consensual Heterosexual Fiction InLaws Cream Pie Facial Oral Sex Tit-Fucking Voyeurism Public Sex
“Why are you staying in a hotel? You could have taken your old room,” Leo’s Mum scolded as everyone said their goodbyes.
“Didn’t want to intrude on you and Dad.”
“Nonsense,” his Mum glared annoyingly.
“Leave him alone, he probably just wants his privacy,” his Dad spoke up.
“Okay. Well, I’ll meet you for brunch tomorrow?.”
“Sure, Mum. Goodnight. Thanks for dinner,” Leo expressed and gave her a warm hug.
Leo shook his Dad’s hand and then hugged his niece, Izzy. His gaze spotted Charlotte whispering something into Sophie’s ear which made her Aunty giggle and blush. Sophie then looked over at Leo coyly. Was the whisper about him? Leo wouldn’t put it past Charlotte.
“You need to visit more, I miss spending time with you,” Izzy mewed, still hugging Leo tightly and grabbing his attention away from the gorgeous blondes exchanging whispers.
“I miss you too. I will visit more I promise. Have to make sure the boys stay away from my beautiful niece,” Leo joked.
Izzy beamed a smile up at Leo. His niece had blossomed into a fetching young woman. Hopefully, she didn’t get up to the same things as Charlotte.
“I’ll drop the girls home and meet you guys at the bar,” Tom announced. Kissing Lena and then hugging Sophie. “ drive safe,” he directed at her and shook Leo’s hand.
Everyone was soon out the front door, Charlotte giving him another cheeky wink as she jumped into her Dad’s car.
“Wow, nice ride. Someone’s doing very well for themselves,” Leo judged as Sophie unlocked her Silver Mercedes convertible.
“It’s easier to sell houses when you’re a hot blonde with big tits,” Lena teased.
“Oh My God, your brother is going to think I use sex to get ahead,” Sophie yelled, red-faced.
“It’s okay, I use my good looks all the time. Lena wouldn’t understand being an ugly duckling,” Leo jokingly mocked his older sister.
“Well, I’m getting married to a hot guy, while you’re still single and alone little brother,” Lena fired back looking all sassy with a hand on her hip.
“You know what, you’re right. I am the ugly duckling of the family,” he said trying to garner sympathy.
“I think you’re alright, Leo. Above average for sure,” Sophie offered. Her cheeky statement reminded him of Charlotte’s teasing on the plane.
The girls had a good chuckle at Leo’s expense before they finally hit the road. The bar was a short 10-minute ride and soon enough, Leo and the girls were inside ordering drinks and vibing to the music.
“Wow, this is the first time I’ve ever seen Sophie pay for drinks,” Lena pointed out, acting all shocked.
Sophie looked confused, glaring at Lena for an explanation. Leo looked puzzled as well, maybe Sophie was frugal with her money, It didn’t look like it judging by her designer handbag and diamond jewelry.
“Well, usually when we go out, guys are buying her drinks nonstop,” his sister clarified with a chuckle.
“Oh Gawd, shut up!” the blonde scoffed, then giggled along.
“I did offer to pay,” Leo pointed out.
“Leo will never say no to free drinks,” Lena teases.
“Well, I don’t get pretty girls buying me drinks often. It feels so good I can’t refuse,” he chuckled.
“Relax with the ego, Little brother. Let’s find a table,” Lena then suggested.
After 30 minutes of cheerful banter, Tom arrived joining Leo and the girls. The group ordered a round of shots, Sophie’s idea being the youngest member.
“We have work in the morning, Soph,” Tom reminded his more liberal sister.
“Calm down, Dad,” the blonde jeered.
It looked to Leo like her third drink of the night was starting to kick in. Maybe Sophie wasn’t as posh as she seemed. Leo couldn’t help but grin as she let her hair down.
“Don’t worry, Babe. Tomorrow is Friday, we don’t have many appointments, so let her have fun,” Lena petitioned on Sophie’s behalf.
“I know right? I sold that house on Flinders Street today, aren’t you happy boss?” Sophie sneered at her big brother.
“I still can’t believe you got that price for it. Tom has been trying to sell it for months now,” Lena said with genuine surprise.
“A girl has her secrets,” Sophie replied with a mischievous wink.
“Your big tits aren’t a secret, we can all see them, right Leo?” Lena bantered.
“No comment!” Leo quickly answered seeing the look of annoyance on Tom’s face.
“I don’t think Leo wants to hear about our work, ladies,” Tom interjection, clearly wanting to change the subject.
“I’ll go get us another round of drinks,” Leo offered, nodding at Tom.
“Not for me, mate. Have to drive,” said Tom.
While waiting at the bar, Leo’s phone went off. He checked it seeing a message from an unknown number. “ Hmm, weird,” Leo muttered before opening it up.
{Cleaning the mess you made of my little pussy, Uncle Leo. I’m not on the pill, FYI 😜}The message read. Of course, it was sent by Charlotte. She also added a close-up picture of her pink twat for good measure.
{ Stop it. Not funny, young lady! 😡}Leo sent back. He wondered how Charlotte got his number, probably Izzy he then assumed.
{ Just kidding 😂 Don’t get my Aunty drunk and take advantage of her okay?}
{ Good night! Charlotte}
“Hello, excuse me. Sir, what would you like?” the brunette bartender asked trying to get Leo’s attention.
“Oh sorry. Two Jack and Cokes, plus a vodka tonic, please,” Leo ordered after peering away from his phone.
As he waited for the drinks, Leo couldn’t resist having another look at the picture Charlotte sent. Jeez, her pussy looked sweet and juicy. If only she had taken one sooner, it would have been a glorious sight, seeing his cum dripping from her teen snatch.
“Whatcha looking at?” Sophie frightened him from behind.
Leo closed his screen promptly and turned around toward the curvy blonde who looked menacingly at him,” oh nothing, just a friend from Perth, messaging me” he lied.
“Lady friend?” she quired with a raised eyebrow.
“Yes, but it’s not like that,” he replied in a half-truth.
“It’s ok, Leo. I won’t hold it against you. We only just met,” Sophie expressed grinning.
“Your drinks, Sir.”
“Thank you very much,” Leo sighed, thankful for the interruption. “Let’s head back to the others,” he suggested, handing Sophie her drink.
“Sure.”
Back at the table, Lena was showing Tom something on her phone. The engaged couple was smitten and laughing, Leo seeing Tom in a less serious state for the first time. He still felt guilty about fucking his teenage daughter, “I’m never having kids,” Leo said to himself.
“What’s so funny guys?” Sophie questioned.
“Oh, nothing. Do you remember that Spanish couple Tom showed some houses to a week ago?” Lena asked Sophie.
“Yeah, the 50-year-old who dressed like she was 18?”
“That’s the one. Well, she’s trying to seduce Tom. She invited us to their place for drinks. I think they swing or something,” Lena explained giggling.
“Oh, my. Go for it, big brother,” Sophie teased.” Before you started working with us, Tom used to take many cougars to house showings. I always wondered how he could sell houses so fast,” Sophie playfully joked.
“Very funny. And no, I’m not taking up their invitation. I don’t care if I don’t sell another house, I’m a one-woman man,” he honorably stated.
“Aww,” Lena kissed her fiance lovingly,” I don’t mind if you have to flirt, I want a bigger house, Mr,” she teased.
Everyone had a good laugh. Leo was pleased his sister looked so happy, she deserved it with how her first marriage had fallen apart. Now If only his inlaws weren’t so damn, attractive, things would have been so perfect. They all got along great but with the obvious chemistry between himself and Sophie blossoming. Plus the ongoing Charlotte situation, Leo knew that could change rapidly.
“It’s getting late, we should head off,” Tom suggested.
“Yeah, I do have an appointment at 9,” Lena echoed.
“No worries guys, it was great meeting you Tom. Welcome to the family, and you too Sophie,” Leo gladly expressed.
“Aww, one more drink?” Sophie argued.
“Sorry, little sis. Come on, I’ll drive you home. You can get your car in the morning,” Tom sternly said in a fatherly tone.
Sophie scrunched her face annoyingly at Tom, she looked more than a little tipsy to drive.
“It’s okay, I feel like a walk. You’ll walk with me right, Leo? My place is about a 15-minute walk from here,” said Sophie.
“Yeah, I guess so,” Leo agreed
“Perfect, She’ll be okay with Leo, Tom,” Lena claimed, her arm pulling on his.
“Okay, get home safe you guys. Good night,” Tom said not totally convinced.
Leo and Sophie waved as Tom and Lena drove off. The beautiful blonde then hooked her arm into Leo’s and led him down the path home.
It was a nice, calm, summer night. Just a light breeze blowing from the ocean to their right. The moon was full and bright, quite the romantic beachside stroll Leo thought. For the first time, he forgot about what had transpired earlier that day with Charlotte, Sophie’s teenage niece, and just enjoyed the company of the lovely, gorgeous woman on his arm.
“This is nice. Thank you for walking me home,” Sophie cooed.
“The pleasure is all mine. Are you going to be okay to work tomorrow?”
“Yeah, I’ll be fine after some rest and a few coffees,” Sophie giggled.
“I’m kind of feeling tipsy myself. I don’t normally drink that much, especially on a Thursday.”
“You’re on holiday, don’t worry.”
“True. I should enjoy myself.”
“That’s the spirit. I already have one party pooper brother, I don’t need another Leo,” Sophie teased.
“Oh, crap. I kind of forgot you’re going to be my sister-in-law,” Leo chuckled.
“Is that going to be a problem, Leo?” Sophie asked, peering up at him.
Leo chuckled meeting her gaze,” Having a hot sister-in-law could be a problem,” he confessed.
Sophie smirked then smiled coyly,” Why would that be a problem?”
“I don’t know. I’m being stupid.”
“Liar, just tell me!.”
“Well if you must know. It could cause problems because I find you very attractive. Tom might not like me lusting over his little sister,” Leo confessed.
“Don’t worry about Tom. Anyway, we live on opposite sides of the country, I doubt a relationship would work,” she expressed smartly.
“True. I told you I was being stupid.
“No, you weren’t. I like you a lot too. It’s strange since we just met.
“Yeah, I know. It’s a shame,” Leo mulled.
“Yeah, for sure,” she agreed.
The pair walked quietly until they reached Sophie’s beachside villa. The tension was thick as Sophie turned to Leo.
“You know I shouldn’t probably suggest this, but why don’t you stay here tonight? It’s pretty late to go back to your hotel. I can drop you off tomorrow on the way to work,” Sophie offered with a sparkle in her blue eyes.
“Guest room right?”
“Yeah of course,” she smirked.
“I shouldn’t say yes but, sure,” Leo agreed, returning her smirk.
As soon as Sophie unlocked her front door and led him inside, Leo wrapped his arms around her waist and kissed her neck. The blonde moaned and whimpered as his strong hands roamed her body, massaging her D-cup breasts. Leo couldn’t hold back his lust and desire for the busty blonde. He knew she wanted this just as much as he did.
Sophie struggled to lock her door as Leo’s greedy hands held her firmly in place against his cock. He thrust into her curvy ass flesh and angled her neck back so he could kiss those plump red lips. Damn, her body was a fantasy come true, curvy in all the right places.
The hallway was dark, and Leo couldn’t see what he was touching, so after another minute of exploring her buxom body blindly he relented his assault.
“Which way is the guest room?” he joked, breathing heavily.
Sophie giggled and grabbed his hand, leading Leo into a room he guessed wasn’t the guest room. She flipped on the lights much to Leo’s approval and walked up to him resuming the makeout fest.
The two quickly stumbled onto her bed, Leo on top planting kiss after kiss onto her collarbone, his hands going to her tits as Sophie moaned her delight. She was used to guys fawning over them and Leo was no different. He wanted to get his mouth around them the first time he saw the stunning blonde at his parents’ house.
Leo had Sophie’s dress pulled down in a flash, he helped her up so her red lace bra could be discarded to the floor. Wow, what a set of tits, Leo was stuck in a trance admiring Sophie’s god-given womanly gifts. They had an almost tear-drop appearance, a slightly lighter shade than the rest of her white skin. Her inch or so pink nipples were already poking up, aroused just like his stirring cock. Wow, just wow, these were the best set of tits he had ever touched.
“Are you ok?” Sophie asked amused seeing Leo stare at her girls.
“Yeah, sorry. Just making sure I’m not having the best dream ever,” he replied causing her to giggle.
“Well, go ahead.”
“Huh?” Leo questioned.
“Make sure you’re not having a dream,” Sophie ordered.
“And how would I do that, sexy?”
“Here, I’ll help.”
Leo looked confused until Sophie smacked his right cheek with a loud slap, then another that stung his left. He was stunned looking down at the chuckling blonde.
“Wow, you’re gonna pay for that,” Leo growled taking her arms hostage above her head.
Sophie laughed and playfully struggled as Leo leaned down to bite onto her left nipple. The man then proceeded to leave bite marks all over her firm breasts as Sophie oohed and ahhed in pleasure and pain before he licked the wounds tenderly.
“Am I being too rough?” Leo whispered
“No, I like it.”
“Hmm, you like having your tits roughed up?” Leo asked with a raised eyebrow.
“Yes,” she purred.
“What if I wanted to fuck your tits roughly?”
“Fuck! Yes, please!”
Damn, Leo really hit the jackpot today. Not only did he fuck Charlotte twice, he was now about to have Sophie as well. Any worry he had about the relatives finding out flew right over his head seeing the hot, blonde creature lying beneath him. Better yet, she wanted him to fuck her giant hooters, he wasn’t going to pass this opportunity up in a million years.
Leo rose up into a kneeling position and started to strip away his clothing. He was naked in a flash and straddled Sophie’s torso before she could change her mind.
“Wow, someone’s excited I see,” she chirped, reaching out to fiddle the sides of Leo’s erection.
“How could I not be? Have you ever looked in a mirror,” Leo charmingly replied as he shivered feeling Sophie’s red-painted nails scratching his sensitive glands and veins
“Are you just saying that because you’re about to fuck my big tits?”
“It’s fifty, fifty,” Leo joked.
“You’re lucky I’m horny as fuck and you have such a nice cock, Leo,” Sophie giggled.
Leo smirked and shuffled up higher, bringing his erect penis right to her lips. Sophie got the hint and took his large head into her silky mouth. Her lips looked spectacular wrapped around his shaft as she slipped and slid them along his length.
Like a gentleman, Leo tucked a pillow under her head to make it easier for the blonde to service his tool. As she bobbed back and forth, Leo played with her breasts. The heavenly humming sounds Sophie made vibrated through his cock, Leo groaning his approval seeing the girl smiling at him with a mouthful of cock.
Jeez, he didn’t want it to stop. Thank god he cummed three times already that day or else Sophie’s velvet mouth would have had him on the edge in no time, and seeing her choke and gag after going too far wasn’t helping his staying power. He loved seeing girls struggle with his cock.
Although he loved the blowjob, Leo wanted to last as long as possible while fucking her mesmerizing tits. He gently pulled away from her mouth and scooted down to rest his meat into those dream-like buns. Fuck, he was the perfect length for her cleavage, It was just meant to be, his cock was made for her tits.
“I have body oil in that draw,” Sophie pointed out.
Leo reached over and grabbed the bottle. He guessed having tits like hers, Sophie needed to be prepared. What a good girl he smirked while pouring the liquid over her mounds. Damn, they looked even better all shiny with the coconut-smelling oil, His cock got even stiffer if that was even possible.
Sophie smiled proudly, Leo could tell this girl loved having her tits worshipped and drooled over. She seemed to get off on seeing Leo massage and work the oil into her skin, adding more and more until he eventually pushed her mounds together around his manhood and started to rock back and forth.
“How do my girls feel?” she moaned, grinning up at Leo smugly.
“Like heaven, babe. You love getting these big tits pounded, don’t you?”
“I love it. Especially by a big cock like yours.”
“Damn. You know just what to say don’t you sexy?” Leo grimaced, feeling the pleasure surge through his love muscle. His hands struggled to hold her massive globes tightly around it with the slippery oil.
“Come on, be rough with me, fuck the shit out of my tits, Leo!,” Sophie challenged.
“Fuck! Don’t mind if I do,” he grunted.
Leo pushed the outside of her melons inward, creating the perfect, snug, fuck tunnel for his cock, and plowed into them over and over. Sophie helped him hold her breasts together as Leo plundered hard. His fingers moused over her sensitive nipples, his thrusting rocking the bed with how much force he was using.
“Yes, baby! ... yes! ... yes! ... yes! ... fuck them, I love it,” Sophie chanted. Clearly into the act but not as much as Leo who was in a whirlwind of pleasure.
Of course, tits didn’t feel as good as a tight pussy but the visual aspect more than made up for it, and Leo’s eyes were getting flooded with sensory overload seeing her hooters getting rammed. What a sight, this big tit slut was egging him on to fuck her rack harder, it looked like she was about cum with how her cute face scrunched up and begged for more.
Leo heard women could orgasm from breast stimulation alone. He’d never experienced it before but there it was. Sophie’s mouth gaped open and she trembled. Her blue eyes rolled back into her head and she came while getting tit fucked.
“Wow, fuck that’s hot!” he groaned, not stopping his thrusts into her cleavage.
When he was first introduced to Sophie, she seemed so proper and sweet, but now she looked like a beautiful slut, cumming while he plowed into her mounds. Her lips curled into a wry smile as the orgasm washed away, her big, blue eyes reopening to see Leo smirking down at her. Jeez, this woman was amazing, he hadn’t even fucked her pussy yet and he was already in love.
His cock couldn’t take it. Seeing her orgasm was like a rocket jet had been strapped to his back. Leo felt the cum in his balls boiling up and with a flurry of thrust his cock spewed out like a fire hose. A powerful blast smacked under Sophie’s chin before he quickly snapped his cock out of her tit tunnel to cover her mountain tops in his creamy snow.
“Oh My!” she wailed. Licking her lips while Leo painted her chest.
“Fuckkk!,” Leo bellowed. Impressed with how much frosting he had left after his exploits with Charlotte.
Each of her marvelous globes was decorated exquisitely in his white seed. But he could do better next time, her tits deserved a proper glazing.
After Leo finished squeezing everything out, he hopped off Sophie’s chest and lay beside her catching his breath. He looked over at her playing with his cum, the two locked eyes in a steamy stare, and grinned.
“Want me to get a towel?” Leo kindly offered.
“No, I like to massage it in. It helps keep my girls firm and perky,” Sophie explained quite seriously.
“Damn, happy to help you with that anytime,” Leo snickered. Enthralled as he watched her rubbing his sperm all over her chest like it was sun lotion.
“I bet you are,” Sophie winked seeing Leo’s stare. “ Just give it 5 minutes to soak in. I’m sure you’ll be up and ready by then,” she cheekily stated.
“Fuck girl, I’m ready now,” Leo groaned. Jumping up to his knees and pulling off Sophie’dress past her feet. Leaving her white heels on as he dove between her legs.”
“Oh My God! Izzy!” Leo heard Sophie shriek.
He turned his head around and saw his niece standing by the door. Behind her was Charlotte grinning from ear to ear. What the fuck were they doing here? Leo screamed on the inside.
“Sorry, Uncle Leo,” Izzy offered before running away. Charlotte followed close by but not before winking at Leo.
Sophie quickly jumped to her feet. Almost kicking Leo as she raced to close the door. The oversight was understandable in the heat of their lust.
“Jeez, that was bad,” Sophie said before surprisingly laughing.
“What are they doing in your house?” Leo questioned, the shock still fresh.
“I totally forgot Charlotte is staying with me, sorry. I guess the girls were having a sleepover,” Sophie explained while walking back to the bed.
“You find this funny?” Leo growled at her.
“Kind of. Don’t worry, they are mature girls, yeah it’s embarrassing but, it’ll be ok,” Sophie tried to downplay the situation.
“Arhhhhh, maybe this is just a dream. Slap me again, really, really hard this time,” Leo pleaded.
“Calm down. It will be fine, I’ll talk to them in the morning, don’t stress,” Sophie chuckled while rubbing his shoulders.
“I swear, when something good happens to me, something bad always follows. I think I’m cursed,” Leo whined.
“Oh stop being a baby. I think most guys would still choose to do what you just did to me even if they knew their niece would catch them. She probably didn’t see anything, just you about to go down on me. It’s no big deal,” Sophie told him.
“Yeah, you’re right. We’ll talk to them in the morning.”
“We will. In the meantime, I know something that will take your mind off it,” Sophie tantalizingly suggested.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.