This story is a complete work of fiction. It isn't based on real people or real events. All characters portrayed are over eighteen and you must be over eighteen to read it. It contains rough sex and the first gay time for a younger and older guy. If you don't like that, stop now.
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The Sheriff Started It All
Jeremy Berit considered himself a good kid. He wasn't great at school, but he passed everything. He wasn't a sports hero, but he was on the baseball team and didn't spend the entire time on the bench. He wasn't big into partying either. He had only gotten drunk one time and threw up so much he swore it was the last time.
That is why he couldn't believe he was on the hunt for drugs.
Kristy Swanson was hot. She was a cheerleader and she had a reputation for being a slut. Not just a normal slut, but a mega slut. On one football away game, she had supposedly snuck out of her room and gotten gangbanged. Willingly. David Jackson swears she snuck into the locker room and blew him and Kevin Myers after a workout. Before they even showered.
And this morning, she sent Jeremy a text:
My parents are out of town. If you take me ice skating, every boy at school will be jealous of what happens next. Bring enough candy for the whole night.
Then she sent emojis of an eggplant, a tongue, a peach, and jizz. Well, water or sweat, but it meant jizz.
Jeremy wasn't a moron. Not exactly. But it took him a minute and a search to figure out wtf she wanted. Ice skating meant meth and so did candy apparently.
And that is how Jeremy wound up in the squad car.
Edward
Edward Peel became a cop because he liked power. He filled out on forms it was because he wanted to help people. That was bs. The truth is that he liked having their lives and futures in his hands.
In his fifties, he learned exactly how good that could be.
He used to be a linebacker in school and got all the pussy and dick sucking a boy could want. But as he got older and fatter that ended. Now, his wife only ate his dick if he bribed her. Forget about happy and willing fucks from anyone worth a damn.
He was 6'4, 250 pounds, going bald, and knew he looked like a fat cop stereotype.
That is when he decided to use a little of his power for himself.
The first time was the year before. He caught this cheerleader buying meth. Instead of busting the dealer, he followed her and searched her. Then he made her a deal.
The bitch acted like she didn't like it, but he had a big uncut white dick and it was better than prison or a record.
That sort of became his thing. Catch a chick buying drugs and then get his dick wet instead of arresting them.
But this week was a dry spell.
Until Jeremy.
Eddy wasn't a faggot. Hell, he used to kick the ass of any boy he even thought was a little queer. And he knew Jeremy wasn't a dick sucker. He had seen him play baseball. Faggots didn't play baseball.
But Eddy was going through a dry spell.
And he wasn't about to just let the kid go for free.
Jeremy
I knew I was fucked. I hadn't even gotten back to my car when Sheriff Peel grabbed me. I had my whole savings ($200.00!) worth of meth in my jacket and he found it.
This was the end of my life. Everything. I was going to jail. I was seriously fucked.
When he started driving, I tried to think of something to say. Anything to convince him to not take me to the police station and book me.
Then the car stopped.
I looked around and we weren't at the station.
We were in the middle of some woods.
He opened my door and dragged me out of the car.
Edward
I couldn't believe I was doing this, but I was horny and he was young and small enough I figured it didn't count. He weighed maybe 135 pounds soaking wet and was maybe 5'9. Smooth faced as a baby.
Almost a girl, really. Even if he looked all boy.
I pulled him out of the backseat and made him a deal.
I said:
You got two options, kid. One is you get back in the car and I take you to the station and book you. Assuming you're over eighteen, that's enough meth for a few years in prison. That what you want?
The kid shook his head.
I smiled and said, "Option two is you show me how good a high school baseball player can suck dick."
I saw the shock on his face. For a boy, he was kind of cute. He had brown hair half hanging in his eyes and lashes like a girl. And his body was toned. His lips were even kind of pink.
I thought he might cry and imagined what he was seeing.
I was tall, but had spread out and become thick all over with a belly. I was wearing my khaki sheriff's uniform with the leather boots and my holstered gun. I had on my sheriff's hat and about three days of beard. What hair I had was salt and pepper.
He looked in my eyes, crying, and said, "Please, I don't want to go to jail."
The kid crying was giving me a semi.
I looked at him and said, "On your knees, faggot."
The kid didn't move so I pressed down on his shoulders.
He sunk to his knees, but then nothing.
I slapped the kid across the face hard, trying to bring him out of whatever state of shock he was in.
It didn't work.
Finally, the kid talked.
He said, "I can't. I'm sorry. I can't. I can't be a cocksucker."
I respected that. Not enough to let the kid go, but I respected it.
I told the boy, "I get my nut or you go to prison, Jeremy. Your choice."
Jeremy hesitated. He looked around.
Then he said, "If you rape me, it isn't gay, right? I could bite you in my mouth, but up my ass I couldn't do anything. You're bigger than me. "
I was blown away for a second at the idea. No one had ever taken my dick up their ass. But the kid was right. In a way. It would sort of be less gay. Less consensual. More passive.
I nodded.
Then I said, "But I get to jizz up your asshole."
Jeremy
I tried to suck his dick. I really tried. But on my knees looking up at him, I couldn't move. I couldn't do it. I didn't want to go to jail, but I couldn't like decide to be a cocksucker. I couldn't reach out and unzip a man's pants and take his dick in my hands or mouth.
I also couldn't go to jail. Or have my parents know I bought drugs.
When he agreed to fuck me, it was a relief. I knew it'd hurt and be awful, but girls were total pussies and survived getting assfucked. I had been beaten up, broke my arm, and even had my appendix removed.
This couldn't be worse than that.
I stood up and pulled my sleeveless Wildcats jersey off. Then I pulled my basketball shorts off.
I stood there for a second, in just my high school branded boxer briefs, and then took them off too.
I stood naked, then turned to face the squad car.
Edward
My dick was actually oozing a little. The kid didn't have a real cunt, but it had been way too long since I had pounded pussy.
And the kid looked like he had a tight little ass pussy.
I watched him undress and thanked God for these modern kids. It looked like he shaved his crotch and stomach and even chest, unless he was somehow a freak of nature. Kid didn't even have a happy trail, just a little leg hair.
His dick was soft and around three inches soft, not that I gave a fuck about that.
It was his petite little gymnast type body and submission that was getting me hard.
I opened the squad car door and placed my hat on the seat. Then I undid my holster and placed it and my gun next to the hat. Then I took off my clothes and underwear.
I walked over to Jeremy and kicked his legs apart. Then I kneaded his smooth little butt cheeks as he flinched.
Jeremy
I watched as the Sheriff undressed. He was fat and old and hung and I wanted to just scream and run away, but I knew better.
When he kicked my legs apart and I felt his hand on my ass, this became way too real.
I spoke then:
I know this is going to hurt. Don't stop until you finish. I want it over with. Don't worry about me. And maybe put something in my mouth so I can't scream and people hear or anything. I don't want anybody to see us.
He grabbed my underwear out of the dirt and stuffed them in my mouth.
Then he grabbed my hands and placed them on the top of the car.
Then I heard him spit and he rammed it in.
Nothing could have prepared me for the pain. I bucked under him, but he held me still. I realized I was crying. It felt like someone had shoved a baseball bat up my ass.
He groaned and then pulled out. I almost collapsed from relief.
He leaned in, licked the tears off my face, and whispered, "You got a real tight cunt, kid."
Edward
About ten thrusts in, the kid passed out. I held him up by wrapping my arm around his throat for a few more, then lowered him to the ground.
With him facedown in the dirt, I was able to lay on top of him, wrap my legs around his legs, my arms around his arms and throat, and hump deep.
And with him unconcious, his pussy just opened up.
And it was good fucking pussy.
That first thrust had felt like my dick was being ripped apart. He was that tight. It didn't hurt, exactly, but it was hard to even get it in. Once I broke his hole, though, it was heaven.
I'd never had ass before so hadn't known what to expect.
His hole was like a silk velvet glove squeezing my dick.
I could have jizzed the second it opened up.
Instead, I enjoyed it. I rode his hole hard.
And my dick is not fun sized. It is eight inches and thick as a beer can.
And I made it balls deep.
Jeremy
I woke up still gagged and facedown in the dirt. The weight of the sheriff was crushing me and I couldn't move. His sweat was dripping all over me. My back was wet with it and even my face. All I could smell was his man smell. It was like a locker room and armpits and cheap cologne.
He must have sensed I was awake because he started talking as he fucked me.
He moaned and groaned:
You're a good little faggot, kid...this is great pussy...you were born for this...you're a worthless little cunt...take that dick...I'm going to cream your little ass...uh...uh...fuck...
It still hurt. Every thrust hurt. And he sometimes did stuff I think just to make it hurt. He would pull out and then ram it back in hard and quick. He would pound fast and then slow down and then slam.
I promised to never treat a girl like that in my life. Ever.
Then I noticed something else.
It didn't feel good, but my dick was leaking. His dick was hitting something inside me and it was making my dick leak.
Like, a lot.
Then one thrust did feel good. Weird, but good. Like his dick was jerking my dick off on the inside. Which is fucked up.
I realized I had moved my butt up trying to get him to do it again.
Then he laughed.
He pulled my head back and spat on my face. I could feel it rolling down, except the phlegm stuck on my forehead.
He said, "This isn't about you getting you a nut."
The next ten minutes were a mix of heaven and hell.
It was humiliating and still hurt. But my dick liked it.
I found myself moving my butt against his dick. Even as he called me a fag and disgusting, I was leaking.
Then the worst happened.
I came.
His dick hit that spot over and over until I couldn't help it.
My body jerked and my dick exploded. Jizz went in the dirt and all over my belly.
He felt it because as I jizzed, almost at the same time, I felt his hot cum flood my insides.
Edward
I thought for a second I was going to have a heart attack. The kid was a tight fuck and when he started grinding himself against me that took it next level. But when he came.
Fuck.
It was like his asshole spasmed around my dick and just squeezed and massaged the load out of me.
It was a fucking surprise nut. I hadn't had one of those in years where it was just so intense I blew my load without intending to.
I pulled the kid's boxers out of his mouth and wiped my dick off with them before getting up.
Then I stared at his ass as I got dressed. I must have slapped the shit out of it at some point because his cheeks were red. So was his hole, but I could see my cum oozing out of it.
I had seriously just fucked a teenage boy. An athlete. A high school kid. Up his tiny little jock asshole.
And it had been fucking good.
The kid was still laying there so I kicked him gently in the side.
Then I said, "Get up. I'm done."
Jeremy
I hurt all over. I tried standing up and almost fell. My knees were wobbly.
I felt weak af.
I looked at the sheriff. He was leaning against the car, totally dressed, and smoking a cigar while he watched me.
He looked so normal.
Like nothing had happened. Like he hadn't just fucked me.
I picked up my underwear and wiped the cum off my ass and stomach and dick. Then I pulled my shirt and shorts on.
I didn't know what to do with my underwear. They were soaked with our cum and disgusting. I finally just put them in my shorts pocket.
Sheriff Peel laughed.
Then he said, "Get in the car. Front seat."
The drive back to town was weird. He kept talking about baseball teams and acting like nothing had happened.
Then we were back at the store.
I started to get out and he stopped me.
He picked up the bag of meth and said, "I can pick you up for this anytime I want. I'll be seeing you, kid."
Then he squeezed my thigh and I got out.
My brain was racing. I stood in the parking lot for what felt like ten minutes after he drove off.
It felt like everything had changed.
Why was my dick so hard?