I’m The Worst

A story that was requested by a very dear and dirty friend. Hope you enjoy.

This story contains taboo themes such as age gaps, infidelity, reluctance, and drug use. ALL characters are 18+

Read at your own discretion!

—

"Fuck me harder, you piece of shit!"

I was on my knees, 4 out of 8 inches of my dick stuffed into ex-wife's pussy, in the bed she shared with her new husband.

I'd come over to inform my old girl Elizabeth that I was going to marry the 18 year old babysitter I cheated on her with. Not because I loved her, but because my new buck-tooth, backwards, gun-toting father-in-law caught me plowing into his precious little Julie under his roof, and promised to make my life hell if I didn't "make a good woman out of her". I'd soon find out that translated to a guaranteed meal ticket for his most rebellious daughter, which took her off his hands for good.

Anyway, it wasn't really a punishment, was it? I didn't have it half bad. She was still a teenager, after all. Not the worst thing to come home to after a long day at work. I still cheated on her, so not much had to change. I pictured her as a domestic goddess - impregnated with my semen, legs spread, bursting with milk from her swollen nipples. I sawed every inch of my dick into my ex until I shot my cum inside her.

Elizabeth moved on quickly once she was done with me. She was a catch, even at 41, so it didn't take long for her to bag a new walking talking wallet and get full custody of our daughter. After some resistance, even I couldn't deny that it was the best option. I continued to have meaningless sex with our teenage home wrecker and her gaggle of BFFs to soothe my pain. Presently, I had Liz pinned down in the same position she found me and Julie in a year ago, filling her up with cum the same way I filled up our babysitter that night. If I had known our screaming matches would balloon into the most delicious hatefuck we'd ever have, I would have done it sooner.

For Elizabeth, it was an attempt at revenge. For me, it was good and dirty sex, just the way I liked it. As I pulled my limp dick out of her stretched out hole, I debated between cleaning myself up right away, or sticking my dirty dick into my fiancée's mouth when I got home. I told myself the latter would add some spice to Liz's vengeance, so in the spirit of closure, I zipped up and slapped her ass hard.

"Fuck you!" she yelped.

"Sour loser?" I gloated.

"No, just human. I've been one the whole time, you know" she grumbled.

She continued her sighing and mumbling while I buttoned my shirt. I noted all the red flags and knew better than to respond to her fussing. Our first fight might've ended in a wicked lay, but I didn't want to push my luck with a second. It was evident that her haphazard revenge plan didn't hit the spot, so I thought it best to give her some space to reflect. I kissed her head, wished her well, and made my way to the door.

"You're the worst!" she called out, defeated.

"Until next time, babe!" I chuckled back, knowing she'd want more soon enough.

She threw a pillow at me and missed.

In my car I spotted a girl changing in the neighbour's window. I quickly snapped a few pictures and made my way back home.

I walked in to find my sweet Julie curled up naked on the couch watching TV and running her fingers along her smooth thighs. She looked peaceful bathed in the afternoon glow.

"Daddy!" she exclaimed and ran towards me.

I wrapped my arms around her and picked her up while she planted kisses all over my cheeks and neck. I sat her back down on the couch and wordlessly pulled my freshly fucked dick out of my pants and let it hang in front of her face. She took in the sight for a moment before sticking her tongue out and absentmindedly lapping at my thick cock while stroking it, unknowingly washing away my ex-wife's cunt with her young, dumb spit.

I held my dick at the base and slowly slid it into her throat. Once she was locked in, I grabbed a fistful of her hair and picked up my pace until she gagged and heaved around my member. Throat-fucking was the highlight of Julie's training, and she knew it. She shone brightest with a dick between her lips. The sight of her pretty face covered in spit lit a fire in me. I pulled my rock hard dick out of her expert throat and pushed her thighs back as far as they could go, until her inexperienced asshole revealed itself to me. I spat on it and swirled my index finger around her tightly puckered hole. I decided then that I'd had enough pussy for the day.

"Nooo Daddy, you know it doesn't fit inside there yet!" she pouted, legs still in the air. Adorable.

"Sshh babygirl, just let Daddy put the tip in like last time. Grab my dick." I mumbled, distracted by my finger now pushing harder against her virgin hole. I spat on it again and looked at her expectantly.

She silently guided my cock to her entrance like the well-trained fucktoy she was. I wasted no time stuffing as much as I could into her before she could change her mind. It wasn't much, but it was enough to make her squeal.

"Good girl" I panted, "You're such a good fucking girl"

Her eyes were glued shut as she pushed her hips down further, eliciting a tear from her strained and wrinkled eyelid. I took pity on her.

"Here babygirl, just grab my cock and jerk it off into your butthole, OK?" I reasoned.

"OK Daddy. C-can you make it a more slippery, p-please?" she said shakily, looking up at me with her big doll eyes.

I smiled and squeezed her thigh in response. I pulled the tip of my dick out and straddled her chest.

"The wetter you make it, the easier it will be on your butthole, babygirl" I said as I ran the head of my dick across her glossy, pink lips.

Happy to regain some control of the situation, she propped herself up on her elbows and gathered up as much lubrication as she could in her mouth. I squeezed her face with one hand and gave her a playful slap on her cheek, causing a drop of spit to spill out past her wet, pursed lips.

"Good girls suck cock right out of their buttholes, babygirl" I muttered while running my hands through her hair.

She smiled proudly and shot out an impressive blast of spit onto my dick and began to spread it to the rest of my shaft with her hands. She sucked on the tip hungrily, embracing her own filth. Her enthusiasm was intoxicating. I pushed my dick into her throat and pumped her face until she foamed at the mouth. I love to reward eager sluts.

I pulled out and planted a kiss on her forehead.

"Look at what a good job you did, babygirl. Now it's nice and ready for your little butthole" I said smiling, stroking my cock with globs of her foamy spit hanging off of it.

She beamed at me and adjusted her position to allow me back into her ass. I was able to fit more in this time, but not by much. I tried to hammer my dick in a few times, to no avail. Fuck, she was tight. She whimpered the whole time.

"Sorry baby, Daddy got carried away. Just milk my cock into you now, OK?" I sighed, my disappointment hanging thick in the air.

She obeyed immediately, jerking around trying to find the best angle to grab my dick in. I held her by her ankles and watched her coat her delicate fingers in her mouth and slide them around my throbbing staff. She wasn't winning any points for stimulation, but the visual was working to her benefit, and certainly to mine.

I closed my eyes for a moment and imagined how good it was going to feel to finally rip into this little bitch. My thoughts went hazy and I drifted to a memory of me pounding her best friend's asshole on this same couch, while Julie was passed out drunk on the floor. Ava was the slut of Julie's girl gang, so it wasn't hard to get my dick in her. It wasn't even her first time being ass-fucked. She loved it enough to betray her best friend, which was a huge turn on for me.

Julie didn't always mind me fucking her friends. She actually felt a sense of pride in having a generous older boyfriend with a big dick and endless supply of intoxicants to share. She just wanted to be included so she could show off the skills I'd taught her, and claim some semblance of ownership over my dick. To me, this just meant I had to get creative when it came to sating my impulse towards wickedness. Fucking her best friend quite literally behind her back was too good an opportunity to pass up. Technically, she was included, she just didn't know it. My sinister thoughts were interrupted by a sharp cry.

"DADDYYY!" Julie wailed.

I looked down to see half my fat dick buried in the poor girl. My daydreaming seemed to have gotten the better of me as I hadn't realized I had been thrusting into Julie's ass the whole time. I looked up at her grimacing face covered in tears and spit from my earlier assault. The image robbed me of what little restraint I had left.

My head was spinning, flashing with filthy images and taboo thoughts. Memories both real and imagined. Tight sluts coked out of their minds, moaning like bitches, presenting their holes like bottomless pits of debauchery. I wanted to choke Julie, I wanted to slap her. If she wasn't so hot and easy, I would still have my old life. Yeah, it was her fault for being so fuckable. She came onto me first. I wanted to be a good husband, a good father, but she was too dumb, too ripe to deny. I wanted to stick my fingers down her throat and make her gag, so that I could make the most of her evil young asshole around my dick right now. Instead, all I could produce were a string of mostly incoherent obscenities, while I continued to fuck into her.

"You're doing great, bitch, just a little more, keep fucking going for Daddy, you stupid fucking bitch...you're a stupid...fucking...young...oh...fuck...dumb...bitch..." I growled at her as I shot my cum into her tight fuckhole.

She managed to settle her sobbing into sweet little whimpers for me by rubbing her clit. I kept fucking her with my softening dick while I unloaded into her ass, watching my cum spill out of her hole and coat my dick. I slid it out, gathered up the spilled cum with the tip and stuffed it back into her fuckhole one last time for the day.

Then I brought my dick up to her lips.

"Good girls suck cock right out of their buttholes" she said hazily. Then she gulped my dick up until it was all clean. Nope, I didn't have it half bad at all.

My dick popped out of her mouth as I collapsed into the couch next to her. She snuggled up next to me and pecked the sweetest little kisses on my cheek. I pushed her off and went to grab a hot towel for her ripe asshole. I washed my dick off in the bathroom while the towel heated up and used the time to check my texts. One from Elizabeth informing me that I'd left a cuff link behind and I was more than welcome to pick it up next Tuesday. I chuckled at how predictable she was. I got another from Ava.

"cant stop thinking of u daddy xxo"

Attached were two images, one picture of her laptop screen with porn on it. Your typical porno teen cocksucker with a dick the size of her head pressed against her cheek. She had her tongue hanging out and her eyes crossed.

The other image was dirty little Ava bent over her bed, exposing a pink, plastic jewel embedded into her ass. I wanted to respond right away, but I figured I'd accrued enough bad karma for one day, so I zipped back up, put my phone in my pocket, grabbed the towel and went back to Julie. I still had to finish what I started.

I flashed another glance at the girl in the window before I locked my phone. My heart raced. I'm a peeping Tom now? A brand new fucking low?

"Thank you, Daddy" Julie smiled and kissed my lips softly while I patted her hole with the warm towel. I put her back in the position I fucked her in like a rag doll, and pressed the towel between her tender cheeks.

"That was perfect, baby. I'm so proud of you." I leaned forward, kissed her deeply and began rubbing her pussy. She purred in anticipation.

"Daddy hasn't forgotten about your little cunt" I whispered into her ear as I tossed the towel aside and replaced it with my large hands. She sighed and moaned freely, fully enjoying the fruits of her labour.

I pawed at her mound teasingly, then focused on the moneymaker. She froze in place and stared at the ceiling, mouth agape. Her jaw quivered when I pressed down harder and swivelled the tips of my middle and ring fingers around her swollen clit. When her thighs started to buck, I plunged both fingers deep into her greedy hole and used them to pull her hips up higher. I moved my head between her legs and ate up her pussy.

Pressing my tongue on her clit, I continued to stuff her hole with my thick fingers, alternating between massaging her g-spot and slamming into her. Her moans grew louder and louder, matching the volume of her wet, juicy, desperate cunt. Her hips jerked up and she started to squirm, pushing my head back. I swatted her hands away and continued to slurp up her juices until she exploded into my mouth, arching her back.

I couldn't get enough of this horny slut so I kept pushing my fingers into her, despite her protests. My cum started to ooze out of her asshole as her pussy throbbed around my fingers. I fingered both her holes deep and slow until I coaxed a decent amount of cum out from her ass into my other hand. I brought it up to her quivering lips.

"Good girls also drink their Daddy's milk out of their assholes, babygirl" I looked down at her menacingly.

She hesitated for what felt like hours before bending her head forward and sticking the very tip of her pink tongue into my palm. I knew she had it in her. She cautiously swirled it around in the puddle of cum. I reached for my phone and started to record my baby's first anal creampie. Once she heard the ding of the camera, she instinctively straightened up and put more gusto into it. Julie was a natural show-off, and I encouraged it.

She pressed the flat part of her tongue into my palm and raised her face to the camera, letting her well-earned creampie drip down her chin. She wagged her tongue around her lips desperately trying to scoop the cum off her face, and into her mouth. She arched forward and heaved a little, not taking her eyes off the lens, then threw her head back and gulped proudly. She licked my hand clean obediently and smiled brightly at the camera.

"Perfect little girl" I said, admiring her glistening wet body.

"Dirty little bitch" she mocked, doing a gravelly impression of me.

I laughed sincerely and turned off the recording.

"Go clean yourself up, pornstar" I teased, then watched her bounce away.

Once she was out of sight, I opened my messages, and sent the video to Ava.