Caught in Charlotte's Web - Cover

Caught in Charlotte's Web

Copyright© 2025 by Milly Mills

Chapter 1

Drama Sex Story: Chapter 1 - 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/ft   Consensual   Heterosexual   Fiction   InLaws   Cream Pie   Oral Sex   Public Sex  

Just something a friend wanted me to write. Hope you all enjoy :)

Leo Clark sighed, he hated planes and traveling in general, but here he was boarding a cheap, budget airline flight to Sydney from Perth. His older sister was getting married again for the second time to some guy she worked with. Ahhh!, why did he agree to come to the wedding? His regret only got worse when a fat guy stopped to tuck away his carry-on luggage. “ Please god no!” he cried out in his head, hoping the overweight man wasn’t his seat neighbor.

Leo sighed again, this time in relief as the guy took a seat behind his, he accidentally kicked Leo’s backrest, struggling to cram in. “ Poor guy,” he whispered, Leo was half his size and even he had trouble fitting into the small seats.

The 32-year-old man kept a close eye down the aisle. It looked like most of the passengers had boarded. Leo grinned, maybe he was going to have a free seat to stretch his arms on the 4-hour flight, what luck.

“Sorry for the delay, we are just waiting on one more passenger to board, please be patient and stay seated,” rang out through the PA system.

There were more than a few groans in response to the message, including Leo’s. He too was getting annoyed, he just wanted to get this flight over with as soon as possible. Another 10 minutes passed since the plane was due to take off, and then a young woman finally came huffing and puffing down the aisle.

His annoyance dwindled seeing the cute, blonde hurrying to her seat. She offered up apologies to other passengers as she walked by, clearly embarrassed. When she stopped next to him, Leo immediately knew the empty seat was hers. His brown eyes couldn’t help but dart up and down her slim figure as she reached up to put away her carry-on bag.

Holy shit, she was hot, a lot younger than him but the older man couldn’t stop staring. Her choice of flight attire didn’t help his cause either, tight, black singlet top covering some perfectly shaped B-cup breasts he guessed, and even tighter black bike shorts. He tried to fight the urge to not look between her thighs, but he failed and noticed the slightest hint of a camel toe.

Leo quickly diverted his perverted gaze as the young girl finished with her bag and shuffled in to take the seat beside him. He got a closer look at her face, Dam! She probably wasn’t even 18, her pigtail hairdo only adding to her youthful facial features.

“I’m really sorry for delaying the flight, my mum’s car broke down on the way,” she explained, whispering softly to Leo.

God, her big blue eyes were gorgeous, Leo couldn’t stop staring into them as she spoke.” It’s ok, it was only like 10 minutes or so. I’m glad you made the flight,” he whispered back in a friendly tone.

“Yeah me too, I had to beg them to let me on, I even tried to cry,” the girl said giggling.

Leo chuckled along with the stranger, she seemed friendly and not stuck up like some pretty girls he had encountered. So much better than having a fat guy sit next to me he joked to himself.

Before too long, the plane was taking off. Just 4 hours he chanted in his head over and over. But at least I’m next to a hot blonde, he had to smirk at his luck.

“I’m Charlotte by the way.”

“Hey Charlotte, I’m Leo, nice to meet you,” he replied with a smile.

The girl had a beautiful smile, her smooth skin lightly tanned. Fuck! It was going to be hard for Leo to not steal glances at her the entire flight, hopefully, Charlotte wouldn’t notice his wondering eyes.

“Do you fly much, Leo?” she asked while fumbling with the seatbelt, trying to get it undone he guessed.

“No. I hate flying, but only when I absolutely have to I will. How about you, Charlotte?

“I don’t mind flying, sometimes you meet interesting people,” her smile beaming with positive energy.

“Well, you are out of luck, I’m just an average guy, average in every way sadly,” Leo said mocking himself.

Charlotte giggled and winked at him playfully,” It’s ok, I like average,” she replied before rummaging through her shoulder bag for something.

Leo grinned. Was this young girl flirting with him? No way, but maybe? Oh well, a guy could dream he thought.

“So what are you doing in Sydney? Visiting someone that thinks you’re average?”

Wow, this girl is a little cheeky, Leo smirked seeing her amused grin,” Kind of, my sister is getting married. I promised I’d attend the wedding since I hadn’t been home in a couple of years. You know with Covid and all.”

“Oh, cool. Yeah, Covid sucked. I’m going to my Dad’s wedding, I haven’t seen him since Lockdowns started as well,” Charlotte shared.

“Looks like we have something in common then.”

“Yeah, small world. Hopefully, your sister found a super duper average guy like you to love,” Charlotte joked again.

“I don’t even know you and you’re already busting my balls.”

“Sorry, just trying to amuse myself on a long flight. If you want to know something just ask,” the girl offered happily.

“So how old are you, Charlotte?” Leo finally asked after thinking of a question.

“Why would you ask me that? She scoffed with sass.

“I don’t know, it’s just a common thing people ask.”

“Common in a job interview or if you’re trying to pick someone up. Jeez, I don’t even know you and you’re already trying to get in my pants,” Charlotte accused frowning.

For a moment, Leo was convinced she was being serious until a small grin appeared on her cute lips. “ Okay, I see, busting my balls again. I guess I deserve that though. It does seem a bit pervy,” he admitted.

“That’s okay, I’ll forgive you. Guys are guys. I’m 20 if you must know,” she confessed with a wry smile.

“That’s a relief ... I mean that’s cool, I would have guessed younger,” Leo said coughing.

Charlotte giggled nodding. She was young, but this girl had experience with men, Leo surmised. She didn’t seem at all bothered to be flirting with a man much older than her. If he was 50 percent sure it was his lucky day before, Leo definitely knew 100 percent now that it was.

“Let me guess you’re like 28?” Charlotte estimated after her blue eyes gave Leo a close inspection.

“Close, I’m 32.”

“Darn, the scruffy beard threw me off. You’re hot though, for an older guy.”

“Thanks and don’t worry, you can’t be right all the time, young lady,” Leo teased.

“God, don’t call me that, it makes you sound so old. Unless that’s your kink?” Charlotte wittingly shot back.

“Fuck, you’re right. Sorry for being weird.”

“That’s okay, I also like weird guys, along with average ones,” the blonde girl joked, giggling.

“It must be my lucky day. A cute blonde who likes weird and average men on the same flight,” Leo enthusiastically stated, making Charlotte’s fit of laughter continue.

Leo hardly noticed the time, an hour already flew by while he was openly flirting with the young woman. She was so easy to talk to, it was such a shame about the girl’s age. He couldn’t date her seriously, could he? What would his family and friends think?

“So are you studying or working? Leo questioned

“I’m at Uni, I also work part-time as an escort, times are tough for us young people.”

Leo almost choked, she answered his question with such stone-cold seriousness,” Are you pulling my leg again?” he asked wanting to make sure.

Charlotte’s serious expression then softened, and she giggled at Leo,” This is fun, the flight is going to breeze by if you’re this easy,” she teased.

“That’s me, a naive idiot.”

“Don’t worry, I like naive idiots too,” Charlotte quickly said, giggling again as Leo shook his head.

“I’m scared to ask anything else, you are a pro at twisting my words.”

“Aww ... Sorry, I won’t anymore. I promise,” she cooed, giving Leo the cutest puppy dog look he’s ever seen.

Leo knew the girl was more than likely to break her promise, he really didn’t care. He was having a good time no matter where their conversation led. Charlotte was probably just teasing the poor guy, getting a thrill, it wasn’t likely she was interested in him romantically.

“Are you single?” he asked after a bit of thought.

“Yes.”

“Would you date an older man?”

“Yes.”

“Have you dated an older man?”

“Yes.”

“Are you lying to me?”

“Yes ... wait no ... sorry you were asking questions so fast I got confused,” Charlotte chuckled.

Leo laughed along with her,” So all your answers were true then?

“Yeah, of course. Would I lie?” She asked with a cheeky wink.

“I believe you, but I am a naive idiot as you know, and like apparently,” he replied faking a sad face.

Charlotte chuckled, rubbing Leo’s knee sympathetically. The man was more than pleased at her display of affection, even if the act was innocent. But something was telling him it wasn’t, well at least not fully innocent judging by her coy grin and the time her hand stayed planted where it was.

“I need to go pee, think of more things to ask me okay? Charlotte suggested while getting up.

“I’ll try,” Leo simply replied, his eyes getting another chance to roam over her slim body. Then she turned around, and his cock twitched under his slacks seeing her perfectly formed, small bubble butt. Her tight shorts molding around her ass beautifully.

His stare followed Charlotte’s ass as she sauntered down the aisle, disappearing behind a curtain. Leo then locked eyes with the large man behind him. He gave Leo a knowing smirk and a nod of the head which he returned grinning, before resting back in his seat.

Dam, two and a half hours gone, for the first time ever, Leo wished the flight was longer. Maybe he should push the boundaries of their conversation more. Time was running out, he might not ever see this girl again. Yes, she was only 20 years of age, and the odds were against him, but fuck it, he had nothing to lose but a little pride.

“Hey, welcome back,” he announced, seeing the smiling girl settle back into her seat.

“Thank you, did you miss me?”

“More than you know.”

Charlotte snickered,” enough time to dream about me?”

“Dam, you really ask the hard questions huh?” Leo laughed, he was smitten with her confident demeanor. Charlotte seemed to just say whatever was on her mind with no regret.

“So I’m not your dream girl? Are my boobs too small? Or I’m too skinny? you like curvy girls right?” she interrogated with tongue-in-cheek humor.

“I’m pretty sure I’ll be dreaming about you just the way you are, Charlotte. I just can’t do it here or else I’ll have a pretty average problem in my pants,” Leo boldly confessed.

“Oh wow, I bet it’s pretty average huh? Sounds hot,” the girl joked pointing down to Leo’s crotch.

“Okay, we need to change the subject,” I’m regretting what I said already,” the man laughed seeing Charlotte giggling.

“It’s your call. But I’d gladly help you out if you did have a huge, average problem in your pants, just so you know,” she replied winking.

“Fuck!, there you go pulling my leg again.”

“I was talking about pulling something average, not your leg, Mr,” Charlotte teased sticking out her cute tongue.

“Dam, you need to stop, girl,” Leo groaned, his cock twitching at the thought of Charlotte pulling on it.

“Sorry. I just can’t help teasing you. I knew you would be fun the moment I saw you. I’m really glad you’re my seat buddy, Leo,” the blonde said genuinely.

“I actually believe you 100 percent this time.”

“You should, it’s true,” her smile seemed to grow even bigger, Leo noticed.

Their racy conversation had to be put on hold as the attendants brought out the drinks cart. Being a budget airline Leo had to pay for a Jack and Coke and Charlotte’s Red Bull which he kindly offered to do.

“Thanks for the drink, I really needed that,” the girl said politely.

“Now I know the secret of how you can stay so perky and bubbly all the time.”

“I know. I shouldn’t drink so much of it. Oh, and don’t think just because you bought me a drink means I’ll let you fuck me,” Charlotte cheekily stated, causing Leo to almost spit out his drink. “ It will take at least 5 drinks for that to happen,” she added, trying to be serious.

“Dam, if only I knew,” the comment had Leo and Charlotte chuckling like school kids.

Leo finished his drink just as the drink cart disappeared. The other passengers were putting back on earbuds or trying to nap again when the lights dimmed. Charlotte was busy scrolling through her phone, one hand twirling her blonde locks. Fuck she’s good enough to eat, Leo pictured

“Hey, can I ask you a serious question, Charlotte?”

“Of course, we are getting to know each other,” she chirped putting away her phone.

“Are you wearing any panties under those ridiculously tight shorts,” Leo teased, smugly laughing thinking he tricked her.

“That isn’t a very serious question, Mr,” Charlotte said snickering,” If you had to guess, what would be your conclusion?”

“hmmm, I think you are. You just have that good girl vibe going,” Leo softly mocked.

“Wow, I should take offense to that. But you’re right Of course I’m wearing underwear,” she said frowning.

“You know I would take your word for it, but you have a habit of lying. I think you need to prove it to me,” Leo proposed confidently with his head held high.

The man locked eyes with Charlotte, seeing her eyebrow raised, before she smirked. He hadn’t expected the girl to comply, but when she shifted and angled her body to the side, her ass pointed in Leo’s direction, he knew she was about to.

“I hate being called a liar,” she spouted. Then Charlotte tugged her lycra shorts down her right hip, exposing to Leo the tiniest black cotton G string he had ever seen on a girl. The strap was thinner than a shoelace. Running down into her crack before she ended the peep show abruptly. Giggling when she saw Leo’s flustered face.

“Dam girl, you have the cutest little butt. Definitely nothing average about those cheeks,” he praised the smiling blonde.

“I know. So where is my apology?”

“For what?”

“Jeez, did seeing my naked tush give you memory loss? You called me a liar,” Charlotte fumed, crossing her arms to express her displeasure.

“Oh right. I’m Very, Very sorry I called you a liar, Charlotte,” Leo announced.” But I don’t regret it,” he added with cheek.

“I bet you don’t. Men are terrible creatures.”

“Very terrible, but we can’t help it, especially when there’s a beautiful girl around,” he replied with charm.

Charlotte huffed but smirked, Leo knew she loved being a tease just as much as he loved watching her tease. It was the perfect arrangement for both parties.

“Hey. No more joking around. This is a really serious question, it’ll make or break our friendship if you are not honest, okay?

Charlotte rolled her eyes but nodded anyway knowing he had no intention of being serious.

“Are you wearing a bra?” Leo asked snickering.

“Oh boy. You are going to have to be more creative to see my tits, Leo,” Charlotte giggled.

“Oh well, guess you caught on to my sinister plan ... Let me think,” Leo pretended when suddenly the captain started speaking through the PA system.

“Good afternoon passengers, we will shortly be descending for landing, please put on your seat belts and put away anything loose. I hope you enjoyed the flight, Thank you for flying with us.”

With all the flirting and games Leo hadn’t noticed the time. Fuck! What bad timing. He looked over at Charlotte who was grinning from ear to ear seeing his dispirited expression. She patted him on the thigh then buckled herself up, ready for landing. Dam she was such a little tease.

The plane landed without a hitch. Charlotte still grinning at Leo as they waited to leave.

“Hey that was really fun, I had a great time. Thank you for keeping me entertained, Leo,” Charlotte told him with the cutest of smiles. If he hadn’t experienced her teasing ways he would have assumed she was a sweet little angel.

“No worries, I had fun too,” Leo replied. The older man debated whether or not he should ask for her contact info. She was way too young for him anyway, probably for the best they left it at that.

Before he could change his mind it was their turn to exit the plane. Leo was about to tap her on the shoulder when suddenly a woman started conversing with Charlotte. There were so many people walking down the tunnel Leo lost sight of the girl in the crowd. Fuck, ruined my chance he thought.

The man sulked and waited for his bag, thinking back to his time with the young girl when suddenly she appeared beside him. Her smile was still radiant as she handed him a piece of paper and strolled off without saying a word.

“Still a fucking tease I see,” Leo scoffed happily as he watched her pert ass jiggle with each step.

The folded piece of paper probably had her number. But when he opened it up, Leo saw a short written note instead of digits. { Come find me in the men’s bathroom, I want to see just how average you are.}the note read. Holy fuck, Leo urgently looked for his luggage and then sped off toward the restroom

Thank god she chose the men’s bathroom, It would have been risky for Leo to enter the women’s without knowing if the coast was clear. He wondered if Charlotte got caught by someone walking into the men’s, Oh well, he had better things to think about now.

Leo entered the bathroom, it looked like it was empty. He called out Charlotte’s name and the girl called him over to the end stall.

“What took you so long?” she asked with a scour.

“Sorry I just thought the note had your number, I didn’t read it right away,” Leo replied with a sorry look.

“That’s ok. I haven’t got long, my dad just texted me. He’s waiting at arrivals,” Charlotte explained, giggling mischievously.

“Dam, you are one bad girl. We can do this another time if you want, just give me your number,” Leo stupidly offered.

“Hell no, I’m so fucking horny for dick. I need to get fucked now. Are you going to help or do I have to wait for the next guy who comes in here?” the little minx growled.

“Fuck, get those shorts off baby, and turn around,” Leo groaned while unzipping his pants, he pulled them down along with his underwear.

The older man grinned when Charlotte cooed seeing his more than average 8-inch cock. Leo was surprised when the feisty blonde sat down on the toilet bowl, she leaned in and took his cockhead straight into her hungry mouth and licked away.

“Fuck, I need to taste this thing first, don’t you dare cum,” she warned with lust after popping him out.

“Holy shit, Fuck that’s good, You’re a hungry slut aren’t you?” Leo growled back as he watched his shaft disappear down the girl’s mouth.

Charlotte hummed and nodded with a mouthful, Leo couldn’t believe this was happening. He hadn’t had a blow job in months and now he was getting his dick sucked by the hottest blonde he’d seen in ages. Dam she was going hard for it, slurping and gulping him down almost to the base.

He braced himself on the wall with his left arm, the right brushing away the girl’s blonde hair. Fuck those pigtails were a dream come true, he just had to grip onto them as Charlotte motored her mouth up and down his member.

Leo threw his head back, groaning in pleasure as the little cock whore tasted his meat, her hands between her legs strumming away on her clit, fuck what a sight, this memory was going to live on forever in his wank bank. She wasn’t trying to be subtle at all, anyone who walked in would be able to hear her slurping and sucking sounds. She wasn’t lying about needing a cock right now.

Charlotte popped him out of her mouth to lick Leo’s very tip, coaxing out more and more precum, It was almost flowing out like a waterfall with how much lust and desire he currently had. The young girl was lapping it up like ice cream, happily smiling as she looked up at Leo.

Leo had a grip on both her pigtails now and was thrusting into her mouth, groaning out his pleasure when suddenly her phone started ringing. The man was perplexed when she pulled away to answer it, leaving his cock stiff and hanging out in the open.

“Hey dad, Sorry won’t be much longer. I think I must have eaten something bad,” The girl informed her father on the other end. Leo could faintly hear the sound of her father saying something before she hung up.

“We need to wrap this up, you want to fuck my tight pussy?” the innocent-looking girl asked not so innocently.

“Fuck yes, can’t wait,” Leo huffed.

Charlotte stood and turned, her shorts and thong around her knees. Leo watched stroking his cock as she got into position, hands on the wall in front of her and ass sticking straight out. God Dam, her cunt lips looked juicy and tight, not a trace of hair on that smooth pink vagina. Leo was in for a real treat, he stepped up and guided his cock into the heavenly snatch, knowing she was pressed for time, and plunged right in. Even though she was dripping wet, her tunnel showed resistance as he plowed inside.

“Oohhhhhh, fuccckkkkk! ... give me that fat dick,” Charlotte purred

Leo couldn’t believe the words cumming out of her mouth, but it only made his cock harder as he rammed into her over and over. Such a sweet-looking daddy’s girl talking like a common slut, if she wanted his dick, she was going to get it, all of it Leo grimaced as he pushed further inside with every stroke.

“You’re so fucking huge. Fuck my pussy ... fuck it ... fuck it ... fuck it ... oh god ... fuck it,” the slim blonde cried out, Leo giving her every inch he had.

His big hands cradled each side of her perky butt, his eyes savoring the view of his thick shaft hammering into her cunt, those juicy labia lips opening up like a pink rose to welcome and guide his rod into her snatch. In and out he thrusts away, slapping his thighs into her ass, This girl wasn’t just talking the talk, she was walking the walk, not many could take this hard of a fucking from his rigid uncut cock. When she said she wanted to get fucked, she clearly meant it.

With the spontaneous blow job and all the teasing on the flight, Leo would soon reach his limit. He didn’t dare slow down and pace himself while Charlotte was screaming for it harder and faster. The man bit the bullet, grimacing, closing his eyes so the stimulation of seeing this gorgeous blonde being impaled on his cock couldn’t trigger a torrent of seed to burst out.

Leo gave her ass a hard slap that echoed throughout the bathroom. That one dominant act had the girl squirming and quivering, her pussy clamping down on his shaft, choking it as her walls contracted in orgasm.

“Ahhhhhhhhh ... ohhhhhhh ... myyyyyy ... cumminggggggg,” Charlotte mewed out, she sounded so innocent while announcing her orgasm.

Leo smacked her ass again and then again while her body spasmed in pleasure. It was all just too much feast for his eyes. Seeing her little bubble cheeks ripple with the slaps and her back arching, those beautiful cries of ecstasy emitting from her lips, Leo was about to burst an almighty avalanche of cum.

The older man had the common sense to pull out just as the floodgates opened. Stream after stream of thick, white sperm snowed down onto the orgasming girl’s lower back and ass cheeks. Fuck he was pumping the white stuff all over this little slut, strands going as far as her black top but most adorned her ass exactly where Leo intended. Her tanned ass cheeks were caked in his baby batter.

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