I came from a very strict family. You know what that means… no fun. No getting drunk, no getting high, no sex before marriage. Even the internet usage was tightly controlled. Fortunately I got a job that allowed me to move out of state. I was far enough away where the family couldn’t control me. The second I got away, I had all the fun I wanted. I drank the bars dry. I got as high as a kite. I fucked every girl in a twenty mile radius. It was awesome.
One day, a few years after I had left, I was browsing reddit when I came across a page where barely legal amateur girls could post dirty pictures of themselves, many of them promoting their OnlyFans. There were some really sexy girls that gave me plenty of whacking material.
One picture caught my attention. A girl in her underwear. She was petite, ginger, just my type. But it wasn’t her that caught my attention. It was her bedroom. I knew that bedroom. It belonged to my cousin Katelyn. She had only turned eighteen last month. It couldn’t be her surely? I clicked on the account. I scrolled back through the account history. The account wasn’t that old, but it was old enough to have plenty of posts. It was the same room every time. Her face was hidden, but I was sure it was her. She was selling custom photos from her reddit account, so I bought a photo with her face in it. Sure enough… it was Katelyn. My sweet innocent little cousin wasn’t so innocent anymore. I’d never really understood guys who had incest fantasies before. But after seeing Katelyn’s tight little ass, all I wanted to do was fuck her.
I messaged her straight away.
“Hey Katelyn. It’s Jack”
“Jack? I don’t know any Jack?”
“Yes you do. Your cousin. Remember? I know it’s you, don’t deny it”
“Ok. Listen, I’m just doing this to make a bit of money. I want to have enough to get a place to rent after I graduate. I use a VPN and sell pics to get me there. Don’t tell anyone okay?”
“Sure… but only if you give me the pics I want for free. Otherwise the family’s gonna get an anonymous email… along with everyone at your school. I’m sure they’d love to know what their honor student does in her free time. I’ve downloaded all of the photos on your profile, so I’ve got all the proof I need”.
She complied like a good girl should. She even smiled in every photo. I kept my side of the bargain of course. I liked my regular stream of taboo photos. She even confided in me from time to time if any of her clients caused her trouble. It was a good arrangement.
Five months went by. She was two weeks away from graduating summa cumme laude. Good girl. But she wasn’t planning on going to college. She was planning on taking a year to establish herself as a writer first. The money she was making from the photos was to finance that first year. She had proven popular and had amassed quite a lot of money… but it wasn’t quite enough. She confessed that she wanted to make as much as she could before deleting the account after graduating.
That’s when I came up with the idea… a fuck a fan contest.
“You know I’m a virgin right Jack?”
“Really? Even better! You know how much guys will pay to be the first cock you take?”
“What exactly are you suggesting?”
“It’s simple. You fuck a fan and film it for people to watch. Guys pay ten bucks to get the video, and fifty bucks for the chance to be the guy in the video”
“I’m not gonna let some stranger fuck me!”
“That’s the thing, it won’t be a stranger… cos it’ll be me”
“WHAT? NO WAY! You’re my cousin you sick fuck!”
“Yeah… and I have five months worth of your nudes. All of them have your face in them. You don’t want those to leak, do ya?”
She agreed…. She posted the announcement on her account.
“Hey guys. I’ll be closing down this account in a few weeks. But before I go, I’m doing one last thing to offer you all. One of you lucky guys will get the chance to take my virginity. I’ll be allowing one of you to fuck me on camera. If you pay $10, you’ll get to watch. If you pay $50, you will be entered into a prize draw. One of you lucky boys who enters the prize draw will get to be the first guy to take me to bed. Good luck”.
Seventy one guys entered.
Forty nine guys paid ten bucks to watch. Four hundred and ninety bucks.
Twenty two guys paid fifty bucks to enter the prize draw. Eleven hundred bucks.
One thousand, five hundred and ninety bucks. It was enough for her.
The fateful day came. I booked a hotel room, making sure that the family didn’t know I was in town. She turned up, with a smile on her face. She acted like she wasn’t into this, but her face gave it away… she couldn’t wait to get fucked.
She dropped to her knees, and quickly unzipped my pants, pulling my hard dick out and kissed the tip. She licked the underside like I told her to and swallowed the head.
I moaned and brought my hand to the back of her neck, “Yes baby girl, just like that”.
She swirled her tongue around the head as she stroked my shaft. She moaned with lust and delight before finally taking it fully in her mouth.
I held her neck and slammed my cock into the back of her throat. She gagged and swallowed what she could to breathe as I pounded into her mouth.
“Good girl” I moaned, “I’ve wanted to fuck you for ages. Especially since you told me you were a virgin. Such a waste of an incredible girl”.
I pulled the top down from her dress, revealing her tiny tits. Of course, I couldn’t ruin her makeup too badly. So I finished on her tits.
She smiled a smile I knew well. The kind of smile that says “we weren’t done yet.”
I pulled up a chair and bent her over it, lifting her dress to see her perfect untouched pussy, glistening with excitement. I lined up my cock, ready to push in.
“No panties under your dress? You really are a good girl”. I quickly reached over to her bag, grabbing the panties she had been wearing. Balling them up, I quickly stuffed them into her mouth.
“There. That should keep you nice and quiet. We don’t want any interruptions, do we?”. She nodded back. I didn’t want any interruptions. It was the most fun I’d had in ages.
I bet she loved the feel of her ass being grabbed, My hands holding her in place, as her pussy was about to get penetrated. Her gagged sounds of anticipation were all she could do as she felt my bloated cockhead against her tiny, quivering pussy. I’d been looking forward to this all day.
“Oh baby Katelyn, you’re gonna feel real good”.
Her scream as I penetrated her was gagged up as I pushed my bloated cock part-way into her quivering lips. The feeling of her being stretched grew and grew. She tried to wiggle away as my cock continued its passage. She hadn’t taken anything like this before. It was too much! She tried to get away!
“That’s it, baby,” I moaned, grabbing her and holding her tighter as I took her dress off. “Try and get away. Moving like that only makes it better.”
With one hard shove, and another gagged scream, my cock was driven into the max, my balls smacked against her body. She was now fully violated, spasming. It was brutal… just the way I liked it. I hadn’t fucked anyone like that for so long. I missed it.
“Oh yeah that’s tight!” he moaned. “Virgin tight, you feel so fucking good!”
The fucking got harder and harder. I realised that she liked it rough, so I showed her no mercy. With a mighty roar, I finished in her pussy. My load was huge, massive ropes of cum plastering her pussy. It felt incredible… but I wanted more. I probably wasn’t gonna get another opportunity to fuck her, so I was gonna make sure I made the most of her.
I grabbed her hair, pulling her up to whisper in her ear.
“We both know I’m not done. I’m taking your ass! Whether you want me to or not!”.
I felt her shiver as she felt her cheeks being grabbed, my hands spreading them apart, as her asshole was about to get fucked. Her gagged sounds of protest were all she could do as she felt my rock hard cockhead against her tiny, puckered ass hole.
“Don’t worry, Katelyn, it’s only going to hurt for a little while.”
Her scream as I anally penetrated her was gagged up as I forced my cock just inside her ass hole. The sensation of her ass being stretched grew hotter as she tried to wiggle away as my cock continued its passage. She could barely handle it in her pussy, I wasn’t sure her ass would survive!
“That’s it, baby,” I moaned. “Fight it! Fighting only makes it better.”
With one hard shove, and another gagged scream, my cock was forced into her ass as deep as it could go. My balls smacked against her pussy. Her ass was now fully violated, spasming painfully, even though my cock was lubed up with a cocktail mixture of jizz and spit.
But I knew she liked it rough. The harder I fucked her… the more she began to love it. I reached under, and with a few deft flicks of my fingertips against her pussy, she plunged, letting out a gagged scream of pure sexual joy. Her asshole clamped down on my cock, rippling along the length of it with strong, silky contractions.
“You hot little fuck doll, I love your hot ass!”
With my cock building up a load, I continued to dominate her accommodating asshole, and she obliged by roaring to another climax. A third one orgasm exploded right after, as my cock began trembling like crazy..
”Fuck yeah, gonna cum, gonna flood your ass baby, fuck FUCK YEAH!”
I fired the first hot shot of jism, splattering her insides. My cock pulsed over and over, Katelyn smiling as she heard my grunts sounding so hot and manly to her as I filled her with a huge load of hot cum. The feel of her ass hole being hosed down propelled her into another orgasm. She had milked my cock for every drop with her three virgin holes.
“You’re such a good lay Katelyn” I smiled, turning off the camera.
“Yeah” she smiled, putting her dress back on. “I actually enjoyed it more than I thought I would”
“Awesome. Maybe it’ll be better next time”.
“Next time…? What do you mean?”
“I’ve got you on camera letting me fuck your holes. Either you give me what I want, or the tape gets leaked”.
“What the fuck Jack? That’s blackmail!”
“Yeah. And you’re into that”
“No I’m not!”
“Yes you are… that’s how this started… and that’s why you’re here now, with my cum dribbling down your legs”.
Sure enough… Katelyn became my fucktoy. Good girl.
Source: reddit.com/r/Erotica/comments/o8ykfq/one_big_job_mf_teen_blackmail