The Sheriff Started It All

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, crossdressing, and gay slurs. If you don't like that, stop now.

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The Sheriff Started It All

Part Four

Jeremy

I could barely walk. My butt and back hurt from the whipping. I felt humiliated and gross. And my own dick was still filthy with my own drying cum as my ass leaked their cum.

The sheriff opened the door when I was done cleaning up the mess on the floor, looked around outside, then nodded for me to come out.

He pointed at the pool shower and I practically ran to get clean. The water stung my back and butt, but it was worth it to just feel less slimy. He handed me soap he must have gotten from the shed and I was back to feeling almost normal pretty quick.

He handed me my shorts and a "Peel for Sheriff" tshirt he must have brought for that purpose.

It was huge on me, but it covered up the welts.

Then he took me home.

Neither of us had noticed Keith Lannmore watching us.

Keith

I couldn't believe it. Like, I literally couldn't believe it. I was ignoring all the bbq shit and playing Smash when I heard what sounded like grunts coming from next door. It got even louder and I could hear what sounded like thumping too.

I sat down the controller and snuck out quietly to the backyard to try and figure out where it was coming from and eventually found out it was from the shed. I watched some older guy go in there and join in and realized it was a fucking gangbang.

Some old dudes were railing some chick hard and I thought I could even hear gagging and choking. I couldn't help myself. I whipped out my dick and started whacking off hard as fuck, imagining some slut like Kristy Swanson taking it from those old dudes. I could just picture her huge flopping titties and tight snatch being railed.

Then I heard muffled talking and what sounded like a belt cracking.

Fuck.

They were beating the shit out of her. I knew I should intervene and stop them, but it was making my dick even harder and maybe she even wanted it.

Then I heard what sounded more like a guy yelping. Then screaming.

Maybe it was some kinky cuckold stuff?

It went back to fucking sounds then.

A few minutes later, I watched as Coach and the older guy left.

I was super close to cumming, but I didn't want to nut until I saw the girl. I figured she might even come out naked.

And she did, except she wasn't a girl.

She was a guy.

It would take me a few days to figure out who he was, but when I saw the dude walk out it was obvious he had just spend an hour as a fuckhole and whipping boy. His face was slimy with cum, jizz was practically running out his ass and down his legs, and he had welts all over him.

And he could barely walk.

It was also obvious he had nutted from it. His dick looked slimy even through the fence hole.

I knew I should pull back, but fuck it. I was close and he was obviously girly enough and enough of a fuckhole for those men to not care.

I covered the fence in jizz.

It took me a week to figure out who he was. It was the Sheriff who eventually gave him away. I was doing my morning run at the school track when I saw the sheriff's squad car park by the woods.

The kid was in the passenger seat.

I saw the sheriff lift his own body up like he was pulling his pants down.

Then his hand reached out, grabbed the kid's head, and pulled it down to his lap.

I couldn't see the dick in the dude's mouth, but I saw the sheriff's face and the back of the boy's head bobbing up and down.

No doubt the kid was a knob slobberer.

The sheriff let go of the kid's head long enough to light a cigar.

He laid back and smoked it as he was blown.

Then I saw his face get serious. He sat down the cigar and I guess both hands grabbed the boy's head.

Then I guess he fucked throat. I couldn't see much, but his face was getting real intense and then his whole body got stiff.

Then the boy's head popped up. I couldn't see any nut on his face, but he wiped his mouth off with his hand.

They talked a minute more before the kid got out.

I followed him to the gym and invited him over after school.

Jeremy

School has a kind of hierarchy of popularity. At the very bottom are the gay and emo kids and stoners and band nerds. Then there are just the norms. And the richies. Then you have the different jocks and the cheerleaders. Swimming and track didn't get you a lot of credit, unless you went state. Neither did lacrosse. But basketball, football, and baseball could make you popular af. All the football players were like gods at our school.

That is why it was so weird when Keith Lannmore invited me to a party at his house after school.

Keith was this huge ass senior with a baby face and cropped blonde hair. His face made him look more like sixteen than eighteen, but his body was major league level. He could have been a linebacker on a pro team. And he wasn't fat either, it was all thick muscle. He was like 6'3 or something and probably weighed a hundred pounds more than me.

Rumors had it he fucked three different hot teachers.

We definitely didn't walk in the same circles.

I mean, I was a cool kid. But he was like next level.

He gave me his address one morning and I knew I was going to show up the second he asked.

He was Keith fucking Lannmore.

And I needed something sane and normal and cool. The past week had been rough.

One day after the bbq, Coach pulled me into his office. I was just in my towel after showering. He shut the blinds in his office, pulled the towel off me, pushed me over his desk, and fucked me.

I bit on my arm to keep from crying out and so nobody could hear.

For ten minutes, the only sound was his quiet grunting as he used me like a fleshlight.

When he nutted in me, he just pulled up his shorts and said, "I'm done. Get out."

I was scared somebody would be able to tell what happened by looking at me so I hid in the bathroom until the team left.

I was mad and pissed and so horny from it I jacked off twice while I waited for the showers to be clear.

It wasn't just Coach either. The Sheriff hadn't fucked me again, but he talked my parents into sending me out on his morning patrols with him. He told them it was safe, but would give me a good idea of what patrolling meant.

We didn't patrol. Not really.

He picked me up at six in the morning. We parked somewhere and he pulled his pants down. Then he grabbed my head and used my mouth.

Some days, he just had me suck him. Other times, he grabbed the back of my head like at the gangbang and just fucked my throat until he came.

And I learned real quick I swallowed or he would make me wish I had.

The whole time he kept up this degrading talk. Every morning.

He said stuff like:

Eat that cock, you dirty little faggot. Swallow my nut, bitch. Massage my dick with your pussy throat, boy. Choke on it, you dirty cunt. This is all you're good for, boy. Yeah, you filthy little dick ditch, eat that man load. Swallow those swimmers, queer.

Over and over until he came.

Then he let me out and I went to the school bathroom and washed my face and brushed my teeth and gargled mouthwash.

Then class.

So, when Keith Lannmore invited me over, I was excited af.

I needed something normal and awesome.

Keith

My mom worked all hours of the day and night so she had built a soundproof home theatre in our media room. It was pretty badass too. One entire wall was a projector screen and then there was a comfy couch and a few bean bags we could pull out if needed. And it was all rigged with surround sound. There was even an attached bathroom and a little mini fridge and microwave with snacks.

I spent a lot of time whacking off in there.

I'd get home from school and connect my computer to it and just pump my dick to the nastiest shit I could find online.

Today, I had something different in mind though.

I locked my dog Toby up in the guest bathroom, but first I took his leather dog collar off. It had one of those engraved brass ids on it that just said, "Property of Keith Lannmore."

Then I looked through all the shit girls had left over here.

Amanda had actually left her thong for me after we fucked. It was black with slut written on it in glittery letters.

Cassie had left some earrings, but I don't think they would be useable.

Karen Johnson, though, she had left a whole little purse. It was this pink thing that had a kitten on it. Inside, there was red and pink nail polish and some kind of beige powder stuff and a brush. There was even black eyeliner, mascara, and eyeshadow.

Kristy Swanson was the real champ today, though. She had this super slutty fire engine red lipstick she wore for blowjobs and she had left one of them here.

Until she got pissed about the gangbang, she had been eating my dick a few times a week.

There was definitely enough here for a good time.

Jeremy

I had no idea Keith lived next door to Coach. I rode my bike over there and sat it on the side of the house.

Then I knocked on the door.

Keith answered wearing gym shorts and sweaty af. His chest muscles were dripping and he kind of stunk.

I was used to the smell from the locker room after practice, though.

He gestured for me to follow him and led me into probably the coolest room I'd been into. It was like an actual movie theater, but in his house. The walls were black and had movie posters and there was a bar and everything.

He locked the door after we came in, then put the key in his shorts.

He made himself a drink like a man too. He put whiskey in a glass and a little ice.

Then he looked at me for a moment and tossed back the entire glass of whiskey.

He said, "Everything you need is in the bathroom. Get ready."

I had seen a pool when I was sitting my bike down, so my first thought was he had a bathing suit for me and this was a pool party.

That would explain why he didn't care about being all sweaty.

I walked in the bathroom, expecting board shorts or swimmers.

I saw a g-string, lipstick, powder, and nail polish.

Fuck. Fuck. Fuck. Fuck.

I didn't even stop to fully process, I just ran.

Keith

I didn't expect Jeremy to bolt like a rabbit, but I was prepared for it.

I had locked the door when we came in so I let him try to open it for a minute. Hell, if it opened, I would have let him get away.

It didn't.

After a minute, though, I decided to stop his bullshit.

I walked over to him, grabbed him by the shoulders, turned him around, and gripped him by the throat.

He was tiny compared to me and I wanted to make sure he knew it.

He also needed to realize how lucky he was. I was Keith fucking Lannmore and I was going to let him take my dick.

He should be on his knees thanking me, not flipping the fuck out.

I squeezed his throat a little and said:

I know exactly what you are and I'm not going to hurt you anymore than you like getting hurt. You are going to go in there and paint your nails, powder your face, put on that g-string, put that lipstick on, and collar yourself. Then you are going to crawl out of the bathroom on your hands and knees and beg me, your master, to fuck you. And when I'm done using your throat or asshole, I'll let you go back to eating and taking old man dick like you're used to. You understand?

I let go of him for a minute. He gasped for breath and then nodded.

I couldn't resist humiliating him a little. I spit in his face and then pushed him into the bathroom.

Jeremy

I felt ridiculous. I went into the bathroom and washed my face. Then I just stared at everything on the counter. I didn't know how to do this.

I had to search on my phone for a video and followed its directions.

First, I put the powder foundation on. My skin was already pretty smooth, but it made it glowier.

Then I put the eyeshadow on. It got everywhere. I had to redo the foundation or I would have had black splotches all over my skin.

The eyeliner stuff made my eyes water and kinda hurt. It was kind of dull and felt like scraping wood on my eyes.

The mascara didn't feel like anything at all.

The lipstick felt weird on my lips. Like really thick. I couldn't believe girls did all this all the time. I had to rub my teeth too because it got all on my teeth somehow.

Then I painted my nails. I wasn't sure what color to do, but figured red to match the lipstick.

I kind of did a shitty job. It got all in the cracks around my nails. I tried to wipe it off with toilet paper, but it only kind of worked.

I let my nails dry, then took my shirt off and my pants and underwear.

I wrapped the dog collar around my throat and tightened it.

Then I put on the slut thong.

I looked at myself in the mirror. I wanted to cry, but I knew it would ruin my makeup.

What I saw shocked me. I wasn't a girl. Clearly. I had toned arm muscles and a flat stomach and everything. I had tiny boy nipples and no tits.

But I looked like a tranny or a trap. My face could maybe pass as a girls with the makeup. Maybe. And my hair was kind of long so it looked like super short girl hair. The lipstick made my lips look slutty and so did the eye makeup.

I didn't just look like a tranny either.

I looked like a tranny slut from some cheap amateur porn.

And I was wearing a dog collar labeling me as Keith's property.

I opened the door, got on my knees, and crawled to my master.