Caught in Charlotte's Web - Cover

Caught in Charlotte's Web

Copyright© 2025 by Milly Mills

Chapter 3: Charlotte and Izzy party

Drama Sex Story: Chapter 3: Charlotte and Izzy party - 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  

“Fuck! I need to get a grip. I can’t ruin things with Sophie.” Leo sighed in the car. The image of Charlotte jamming the dildo into her snatch still fresh in his memory.

His phone started beeping, snapping Leo out of his dirty thoughts. He picked it up and saw a text from the same not-so-anonymous person who messaged him last night at the bar. Fuck, that was the last thing he needed right now knowing Charlotte, but he opened it up anyway.

{ Hey, I know my tits aren’t as big as Aunty Sophie’s but you can fuck them if you want 😉}The text said. The little slut also added a pic of her teen tits, the dildo sex toy wedge between her cleavage. Jeez, she knew how to tease, Leo’s cock tenting his jeans as he stared at the naughty pic and imagined fucking her breasts.

“Fuck, Fuck, Fuck!” He yelled, Finally mustering up the strength to close his screen. He tossed his phone to the passenger seat and started up the car, resisting the urge to reply to the blonde Minx.

“Cunt!” Leo scolded himself, the man almost colliding with a Van as he pulled out. The van driver honked his horn angrily before zooming off. Damn, Leo really needed to take his mind off the drama. He knew just the place to go.

His Dad owned a small electrical repair business. TVs, washing machines, ovens, and anything electrical, really, they could fix it. Leo worked there during his apprenticeship with every intent to take over the business one day until things changed. He just got tired of the same old and needed a life overhaul. His dad wasn’t impressed with his decision and their relationship was rocky from then on.

He still kept in touch with the guys he used to work with, Mostly Joey, his best mate who started out as an apprentice alongside him.

It was 2 pm on a Friday. If things hadn’t changed, Leo knew the guys would have finished their last outcalls and returned to the warehouse to enjoy some beers. And sure enough, a few of them were outback doing just that after Leo said hello to some other familiar faces.

“Hey, look who it is. The deserter,” Joey shouted as one or two others Leo knew laughed.

“Hello, boys. I see you guys haven’t changed,” Leo bantered back.

“Never, mate. How’s Perth?”

“Pretty good, Far away from you so I can’t complain,” Leo snickered.

“You still with that girl, Cora?” Joey asked grinning.

“Nah, it didn’t work out. Moving on to bigger and better things,” Leo replied secretly referring to Sophie’s amazing chest

“You’re crazy, she was hot as fuck. I follow her on Instagram,” his friend confessed with no shame.

“Show us.” Greg, another friend shouted.

Leo shook his head and sighed as Joey took out his phone showing the boys his ex-girlfriend’s Instagram.

“Damn, you were right, Joey. what a body. Kind of looks like that tennis chic Emma Rad ... something,” Greg commented.

“Okay, guys, that’s enough. So great seeing you, dogs,” Leo sneered.

The guys offered Leo a beer and he sat down to catch up. Listening to all their wild stories about work and life. Even though he liked his mining job, Leo did miss working with his old buddies.

“Out of beers, you guys want to head down to the pub? Joey suggested to the group of 5 guys.

“Sure, just for a bit,” Leo agreed.

Just as he was about to start the car, Leo got a call from a private number. He knew it wasn’t Charlotte this time since he saved her contact. He answered it promptly hearing a familiar voice.

“Hey, got your number from Lena. I just finished work. What are you up to? Sophie asked.

With everything happening so suddenly, Leo hadn’t thought to exchange numbers with Sophie. Oh well, he had it now. “I’m just catching up with old friends, going to the pub for a drink,” he answered.

“Sounds great, Can I join you guys? I would love a few drinks,” she said back.

“Yeah if you want. It’s kind of a workers’ pub, not a trendy bar,” Leo explained.

“That’s fine, I have my high-vis vest in the trunk,” Sophie joked.

“Very funny. Okay, I’ll see you there beautiful.”

“Seeya, stud.”

Leo smirked and texted her the address before driving off.

When he arrived expecting to see the dingey, dark, out-of-date local pub he used to frequent after work, Leo was surprised to find it had been renovated and looked quite more modern than he remembered. It was kind of a shame, the place used to get pretty rowdy on a Friday night.

“Frist round on you right, rich boy? Joey jeered. He had gotten Leo to reveal back at the warehouse his yearly salary.

“Yeah, sure.”

The guys got a table and were enjoying their first drink when Sophie arrived with a redhead girl in tow. The ladies waited at the bar to order their drinks. Every male eye in the place was immediately drawn to the stunning women who looked out of place surrounded by men dressed in work wear while they were decked in expensive business attire. Leo remembered that pencil skirt well from this morning, it looked painted on showing off her amazing ass.

“Check that out, boys. Hotties at the bar,” Joey announced. He didn’t have to, all the guys were drooling already. Maybe it was a bad idea for Sophie to join him here, Leo regretted.

“She probably squats every day with an ass like that,” Troy added. He was a new guy Leo only just met.

“Okay, be cool. She’s with me, Leo chirped up to stop the locker room talk.

“No way! You serious?” Joey said shocked.

“Dead serious,” Leo reiterated.

“You lucky mother fucker!”

Sophie and her tall friend turned after getting their drinks, she smiled brightly spotting Leo, and sauntered over like a model. Leo stood and Sophie greeted him with a kiss on the cheek as the other guys’ jaws dropped with her radiant beauty.

“Hey, guys. I’m Sophie, this is Cassie. Sorry if we’re intruding,” she graciously said, beaming her pearly whites at the men.

“It’s cool. Of course not ladies. We are happy for you to join us,” Greg eagerly stated while the others nodded enthusiastically.

“Nice to meet you all,” Cassie offered with a distinct, British accent.

The guys made room at the table for the ladies and soon the awkward tension melted away as everyone started drinking. Cassie was getting along well with the fellas, confessing she enjoyed sports pubs back in England and loved a more rowdy atmosphere. She was definitely an attractive girl, thin and tall with firefly-red curly hair and angelic facial features. She just turned 27 and backpacked throughout Australia with her now ex-boyfriend, but chose to stay because she loved the lifestyle.

“Cassie is our newest recruit. I’m teaching her everything I know,” Sophie happily shared while cozying up to Leo.

“Lucky you, Cassie. Lena says Sophie has plenty of tips and secrets,” Leo said poking fun.

“Oh ... yeah, so I’ve heard and seen,” the redhead responded with a knowing wink to Leo.

“Jeez. Why does everyone talk like that about me?” Sophie interjection laughing.

“What are you guys talking about?” Joey chimed in after looking away from the big screen showing the football game.

“Nothing, mate,” Leo quickly answered not wanting others to hear about Sophie’s rumored sales techniques.

“So are you taking Sophie to Lena’s wedding?” Joey asked.

“Yes. She’s actually going to be my sister-in-law,” Leo confessed.

“Damn, that’s interesting,” he glared at Leo.

“Yeah. Lena’s great, Leo too, we’re going to be one big happy family,” Sophie giggled looking up at Leo while holding his arm tightly.

“That’s awesome. Looks like you lucked out, Bro. My sister-in-law is a horrible troll,” Joey groaned.

“You would still date her,” Leo joked causing everyone to snicker.

The ladies excused themselves to the bathroom just as Leo brought over another 2 jugs of beer. Sophie kissed him as she left, smiling happily.

“I can’t believe you are dating your future sister-in-law. Damn, she looks like a swimsuit model too,” Joey said jealously.

“We aren’t dating, I live in Perth. We’re just friends,” Leo tried to downplay.

“Dude! She’s hanging off your arm like she’s in love,” Joey retorted.

“Calm down. She’s just friendly. I only met her yesterday for the first time,” Leo explained not telling Joey about how they spent the previous night together.

“Fuck! Lucky dog. I’m telling you, she likes you, Leo,” his mate pointed out.

Leo continued to play dumb. Of course, he liked Sophie a lot but he didn’t really know how she felt. Maybe it was just a fun fling for her, no matter what this thing was between them, Leo was just happy to spend time with the gorgeous blonde.

After a few more rounds which he paid for, most members of the group had to call it a night. It was barely past 9 pm, Sophie and Cassie didn’t want the night to end and easily convinced Leo to join them at another bar. He noticed the girls were getting very touchy-feely with one another in their tipsy state. Like most guys, he got aroused at the sight and his mind started to wander watching them hug and giggle, whispering things into each other’s ears and giving him sly looks while waiting for the Uber ride.

Meanwhile, back at Sophie’s place, Charlotte and Izzy were getting ready for a night out.

“I don’t know Charlotte, this dress is a little short. Maybe I’ll wear bike shorts underneath, people are going to see my knickers if I bend over, even just a little,” Izzy worried as she looked over her shoulder at her reflection in the mirror.

“That’s the whole point, it’ll make you feel sexier. Don’t worry, you look so freaking hot,” Charlotte lauded standing behind her soon-to-be step-sister.

The teenage girls were dolled up in matching mini strapless, bodycon dresses that Charlotte had in her luggage. Izzy adorned the coffee color version that went well with her shoulder-length brown hair and eyes while Charlotte had on the baby blue which matched her eyes and contrasted nicely with her blonde hair.

“Wow, we look good. Let’s take a pic for Instagram,” the blonde chirped happily.

Izzy giggled and ran her hands down the sides of the form-fitting dress. She had to admit Charlotte was right, the dress made her look older and hotter. A little tight around the bust and hips since she was a tad wider in those areas than, Charlotte, but she could live with it.

The young girls went threw a slew of different poses in front of the bathroom mirror while Charlotte took pic after pic, laughing and giggling. They finished the final touches of mascara and were almost ready to head out for some fun.

“Take off those little girl panties. Wear one of my G strings, It’ll make your ass look ever hotter,” Charlotte ordered.

“Ummm. Okay,” Izzy timidly grinned, taking her older sister’s advice.

“Perfect, now we are ready. Let’s go,” Charlotte said enthusiastically grabbing Izzy’s hand as the two walked out of her aunt’s house.

Noah, the 19-year-old Uni student Charlotte had met on the beach and hooked up with had invited her to a friend’s house party before the girl found out what a dud he was. She wasn’t going to fuck him again but the party sounded fun. Hopefully, there would be plenty of hot Uni guys for her to choose from. Charlotte needed a proper fuck, Ideally, Leo would be her first choice, but oh well, Aunty Soph can have her fun with him for now, the teen didn’t mind sharing.

The house party wasn’t too far from Sophie’s place, a short 7-minute Uber ride down the coast road and the teens arrived at a two-story beachside home. Music could be heard ringing out onto the street and the sounds of partygoers having a good time.

“It looks fun. If anyone asks, just say you’re 18, okay? But no one will with how hot you look,” Charlotte teased her future step-sister.

“I will,” the more nervous Izzy replied with a shy chuckle. Even though the 16-year-old had a boyfriend, she was kind of excited to maybe talk with older guys.

The girls walked hand in hand confidently past some guys smoking out front and into the crowded house. Izzy’s heart skipped when she noticed them obviously checking her out. Charlotte was right, she did feel sexy and powerful in the tight dress, even more so since it was older guys admiring her.

“Hey, where are the drinks?” Charlotte asked a bulky, gym rat looking guy as the girls walked down the hall.

“In the kitchen. Just keep going and turn right girls,” he replied gawking at them.

“Awesome, thanks,” Charlotte chirped, smiling cutely before leading Izzy in that direction.

“You see how he was looking at you Izz?” the blonde teased.

“Shut up! I have a boyfriend remember? But yeah I saw. He’s fucking huge though, roided up I bet,” Izzy joked giggling.

“For sure. Probably has a small dick,” Charlotte added, laughing.

Izzy and Charlotte quickly found a huge esky full of mixers, grabbing one each as people stared, wondering who the younger-looking girls were. Unlike Charlotte, who didn’t seem to care, Izzy felt more nervous. The other girls were clearly judging her.

“Hey, you came. Who’s your friend?” Noah asked after walking up to the girls.

“She’s my sister, Izzy.”

“Cool. Do you want to sit out back with me and some friends?” the bleach-blonde guy offered.

“Yeah, sure. For a bit,” Charlotte nonchalantly agreed to.

Wow, this guy is really hot, Izzy thought staring at Noah. But he seemed to have his focus totally on Charlotte, which wasn’t a surprise to the brown-haired girl. Her step-sister was so gorgeous and so confident. Ugh, I have a boyfriend, stop thinking about hot older guys Izzy scolded herself.

“This is Charlotte guys. I met her at the beach. And her sister,” said Noah.

“Hey, Charlotte, and her sister,” a hunky, dark-haired guy said smiling warmly at the girls. He kind of had a resemblance to Leo but without the beard.

“Hey, her name is Izzy. Nice to meet you guys,” Charlotte quickly replied, grinning at the hot stranger.

“I’m Chris, this is Heather, over there, are Jack, Archie, and Chole,” he introduced.

Izzy smiled coyly, still holding Charlotte’s hand for support as she waved to everyone. Chris and Heather were obviously a couple, she was sitting on his lap looking displeased as Charlotte smiled at her guy.

“Have a seat girls,” Jack graciously offered after moving to the other lounge occupied by Archie and Chole so Noah, Izzy, and Charlotte, could share the other.

“How old are you girls?” Heather asked annoyingly noticing Charlotte eyeing her boyfriend.

“We’re both 18. I’m turning 19 next month just as Uni starts. And Izzy is starting her Senior year at high school,” Charlotte lied happily.

“So you two are sisters?” Heather continued to interrogate in a bitchy tone.

“Well, stepsisters, as of tomorrow.”

“Awesome, congrats. You two already look like loving sisters,” Chris commented causing Heather to scoff loudly.

“Yeah, Izzy is great. I always wanted a younger sister,” Charlotte chirped, the charming smile not leaving her face even with Heather’s weird attitude.

“I’m happy too. Charlotte is awesome,” Izzy chimed in.

“You girls look pretty overdressed for a house party,” Heather snarkily remarked.

“Well, we don’t know how we’ll stay. A few friends wanted us to go clubbing So...,” Charlotte confidently lied.

“Well, be careful girls. There are lots of creepy guys here tonight who would love to get with hot teenage sisters,” Chris somewhat joked much to Heather’s distaste.

“Yeah, like Noah and Jack,” Chole, the cute petite Asian girl announced.

Everyone had a chuckle except for Heather who was whispering something serious into Chris’s ear judging by the change in his expression.

“Sorry guys, we’re going to mingle a bit. Nice to meet you girls,” Chris begrudgingly said as he and Heather got up. His eyes darted over Charlotte one more time before they walked off.

“What’s her problem?” Charlotte snarled.

“Don’t worry, Heather just gets overly jealous,” Chole answered, knowing what most likely happened.

“I can’t help it if her guy finds Izzy hot,” Charlotte blurted playfully.

“What? He was probably looking at you,” Izzy snapped back.

“Probably both of you. Chris has a reputation,” Chole clued the girls in.

“Hey, don’t talk crap about my friend,” Archie interjected.

“You know that’s true better than most, babe,” Chole accused her boyfriend with a disapproving glare.

“Whatever. We shouldn’t talk about people behind their backs,” he scoffed.

“Yeah true. So Noah and Jack like to take advantage of teenage girls, you were saying Chole?” said Charlotte.

“Oh yeah. Real perverts those two,” the Asian girl chuckled.

“Wow, and they look so gentlemanly too,” Izzy chirped up, feeling more confident.

The girls laughed, and Archie eventually joined them seeing the grimacing faces of his two friends.

Other party-goers popped in and out of their little corner in the backyard, but the core group always stayed the same. Noah and Jack talked nonstop about surfing to Izzy and Charlotte while Archie and Chole were busy cuddling up and making out.

“Hey, I need to pee. Be good while I’m gone, okay,” Charlotte teased Izzy, the young girl was enjoying Jack’s attention.

“Want me to show you where the bathroom is?” Noah offered.

“It’s okay, I’ll be fine. Keep my sister safe,” she replied, smiling.

It was only a half-truth that Charlotte needed to use the restroom. The girl mostly wanted to explore and get away from Noah who was being clingy. Izzy looked happy chatting with Jack, Archie, and Chole ( mostly Jack) so Charlotte knew she would be fine.

In the living room, Charlotte spotted Heather busy chatting and laughing with a couple of girls, Chris was nowhere to be seen. He was so hot and the blonde could tell he liked what he saw when eyeing up her tight body. She probably shouldn’t, but the idea of seducing Chris away from his girlfriend sounded fun, especially since Heather was acting like a bitch.

Charlotte sauntered through the crowd of people, ignoring guys trying to talk to her when she found Chris in the kitchen chatting with some black-haired girl. It looked like he was flirting, the pretty girl was giggling and smiling in response to his attention. Looks like what Chole said was true, Chris did have a wandering eye, poor Heather, Charlotte jeered.

Charlotte didn’t care if he was a cheat, She just liked the look of him. Pissing Heather off would only be a plus, but she didn’t have to know.

The young blonde walked over, Chris spotting her, and the two made eyes. Charlotte smirked at him before reaching into the cooler for a drink. The top of her dress lowered as she bent down, teasing Chris with a glance at her perky breasts. Her long legs looked delectable leading up to her short hem that barely covered her panties.

Charlotte grinned catching him staring, her eyes on his the whole time while bent over longer than she needed to. When she popped back upright, Chris said something to the girl he was chatting to, and she left looking annoyed which pleased Charlotte.

“Hey. Are you and your sister having a good time?” He asked smirking down at the shorter girl.

“Could be better. Kind of boring really,” Charlotte replied looking around dismissively.

“Yeah, a little. I’m surprised no one is talking to you.”

“Oh yeah, why?”

“You know why,” Chris said with a wink.

“I really don’t,” Charlotte fired back grinning.

“Well, if you need me to spell it out. That dress looks amazing on you,” he informed moving closer.

“Did you share that opinion with Heather too?” Charlotte said with cheekiness.

Chris laughed and smugly smirked, shaking his head in response.” You won’t tell her right?”

“I won’t, but only if you do me a favor,” she said flirtatiously.

“Sure, what do you need?”

“I really need to pee. Can you show me where the bathroom is?” Charlotte cooed, battering her lashes at Chris.

Chris snickered and moved even closer, Charlotte could feel his breath on her face. “ Well, there’s one right behind you, just at the start of that hallway. Or I could show you the one upstairs, it’s more private,” he whispered confidently.

Charlotte felt that tingle in her pussy growing stronger. The girl smugly grinned, not replying to Chris, and made her way past the bathroom door and toward the staircase instead. She didn’t have to turn back to know he was following. His eyes were most likely on her ass then up her dress as she sauntered up the steps.

“So are you sure this bathroom is private?” Charlotte asked as she looked over her shoulder at Chris.

“Yeah. Heather made sure everyone knew to stay downstairs,” He explained.

“Oh, this is her house?”

“Yeah. Her parents’ place.”

“Interesting. Which one is her room?” she asked curiously.

“Why do you want to know?” Chris replied sounding puzzled.

“I don’t know. I just thought it might be fun to fuck her boyfriend in her room,” Charlotte explained devilishly while strolling down the corridor.

“Fuck, girl! You are bad,” Chris said thrilled,” It’s this one here,” he then pointed out.

Charlotte smirked and opened the door to Heather’s room. As soon as they were inside she walked over and sat on her bed facing Chris who had a big smug look on his handsome face.

“Noah bragged about hooking up with a hot blonde today. You’re a naughty girl aren’t you Charlotte?” Chris sneered stepping up to her.

Charlotte grinned nodding her head. Of course, Noah would brag to his friends about their hook-up. Boys were boys after all.

“A very naughty girl. But you like that don’t you, Chris?”

“Fuck, yeah! Take out my cock, slut,” Chris ordered her.

Charlotte giggled and shook her head. She found Chris hot as fuck but he was an arrogant cheat, he would have to earn a blowjob or more from her. The girl pushed him away by the chest, and rested her hands, palms flat behind her.

“Not so fast. You’re going to have to make me cum first,” Charlotte grinned and spread open her legs.

“Fuck, Deal,” Chris quickly agreed seeing her tiny little white thong that barely covered charlottes pink paradise.

Charlotte smiled as he knelt down between her open legs and tugged down her panties. Chris urgently attacked her twat as soon as she was bare and exposed, lapping her pussy with licks along the labia and up to her clit.

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