Ashland

Category: Not sure. This one sort of fits in trans, but if I write part two it'll be gay adult youth or authoritarian.

The following story is fiction. It isn't based on any real events or people. All characters are over eighteen and you must be over eighteen to read. Like most of my stories, this one uses potentially offensive language. That is a turnon for the intended audience. Please be respectful of others in real life, never engage in anything even vaguely non-consensual, and use protection. HIV is still a thing, but there are plenty of other permanent things out there protection helps you to avoid.

"Ashland"

Ashland wasn't gay. Or a tranny. He didn't really want to be a woman or anything and he jerked off to lesbian porn sometimes five or six times a day. But he also realized he wasn't entirely normal.

When his cousin Karen came to visit when he was thirteen, he realized something. Her clothes really turned him on. She was kind of a slutty rock type girl and she wore things like torn up band t-shirts with leggings and high boots and really dark eye makeup and bright lipstick. When she went out one night and he was home alone, he snuck into the guest room she was using and dressed up in her clothes. Even her makeup.

And that's how it started.

Now, he was eighteen. He had stolen or bought a few outfits he sometimes wore when he masturbated. Feeling the hose on his smooth legs and even the makeup on his face made him so hard.

And that's how he fucked up.

Ashland wasn't really girly. He didn't have girl hips or anything. He was on the swim team at school, so was really toned and had a swimmer's build. He joined the swim team to have an excuse to shave his whole body. He even shaved his head which let him put on wig caps and wigs easier. His face was a little round and his family was Irish so he never really tanned. He was also only 5'7. But he didn't seem weak or anything and nobody bullied him.

Ashland had started coming home from school and getting dressed up. His parents were out until late and so he had a few hours to just play around. He would do his makeup, put on girly clothes and shoes, and then jerk off watching porn.

Part of his recent turnon came from using Anonymizer23. It was an app that let you broadcast video and meet people in different places. He'd use it to talk to girls and try and convince rooms of people he was a girl. They'd be staring at his chest (he wore breast forms he bought online) and he'd be jacking off. It was hot. He sometimes even did it with guys watching.

And then Dylan saw him.

Dylan went to his school. And he recognized him. Dylan wasn't a jock, but he was popular af.

Five minutes after Dylan messaged him, his phone rang.

Dylan told him to come over, now, as he was. Knock on the basement door and plan to stay a while. Do whatever Dylan wanted. And to try and talk more like a girl.

Ashland was terrified.

But he checked himself in the mirror and got in the car.

Ashland

I knocked on the basement door and waited for Dylan to answer. I was freezing and scared out of my mind. I had been wearing a fishnet shirt with a pink bra, fishnet stockings, and a pink thong when he called and he said not to change. I had on a black wig that had bangs and went to my chin on the sides. It was pinned tight on my head. I was wearing really uncomfortable three inch heeled knee high black boots. My makeup was a mix of pink and black. My eyes were really smoky but I had on pink lipstick and blush. My dick was shrunk, but taped down so it couldn't be easily seen or get hard.

Nobody had ever seen me like this in real life.

I didn't want anybody on the streets to either so I was wearing a big winter jacket of my dad's. It was plaid and ugly, but full length on me.

I nearly pissed myself when the basement double doors swung open.

It wasn't Dylan who opened them, but Colby Dennis.

Colby was our star linebacker. And probably the most popular kid in school. I don't think he even knew I or half the school existed. He had short cropped blonde hair and broad shoulders and was at least five inches taller than me, even in the heels. And he was shirtless, sweaty, and just wearing basketball shorts.

My scared quotient went up, exponentially.

He looked at me and said, "Come on in, baby doll."

I followed him downstairs into the basement.

The basement had been turned into a man cave, basically, but for a teenage boy. There were pictures of girls in bathing suits all over the walls. The only other posters were of FPS video games. The walls were painted black and there were floor lamps that kept it from being too bright or dark. It was sort of what I guess you'd call club lighting. There was a couple of ratty old couches and a projector and like a hundred inch or something screen. The bed didn't even have sheets on it. It was just a mattress on the floor.

I saw the reason Colby was sweaty too. One corner of the room had a treadmill, bicycle, and weight set.

It smelled like a lockerroom in the whole basement.

Colby took the jacket off me like he was my date. Then he laid it over one of the couches, wrapped his arm around my waist, and walked me to the couch.

I sat next to him for a second and he pulled me closer. My head was on his sweaty chest and I could smell him.

He looked down at me and said, "Don't be shy, baby girl. Dylan told me you were on your period, but we both know why you're here."

He reached out the hand nearest the couch arm and furthest from me and grabbed a remote. He pushed play and the screen in front of me lit up.

It was a porn.

I recognized the girl in it too. It was Jenna Kazowski. She was naked in what had to be the boy's lockerroom. What looked like half the football team was there too. Most of them were jacking off and I guess they were all taking turns in her mouth.

I felt Colby's hand on my leg. He started squeezing my thigh and brought my hand to his junk. My hand felt tiny in his hand. After just a second on the outside of his shorts, he thrust my hand inside them.

He moaned when my hand made contact with his dick and said, "Fuck yeah, that's a good little bitch."

I froze then. This whole thing was freaking me out on so many levels. I was in a room with a guy with my hand on his cock and he just called me a bitch.

I tried to get up and he pulled me back down. Then he leaned over and stuck his tongue in my mouth. He tasted like fast food. I felt his whole body pressing against mine and his hands were all over me. I was terrified he'd find my dick.

I slipped out from under him and half fell to the floor.

Then I looked up at him and he smiled.

He stood up, smiled even bigger, and said, "Damn, I figured you needed a warm up. I guess Dylan meant it when he said you were a slut."

He pulled down his shorts and threw them over his shoulder.

Then he reached out his hands, grabbed the back of my head, and said, "Suck it, slut."

I had only a second to realize what was going on. His dick was mostly soft and at least five inches. He had all this extra skin on it. And his balls were huge.

Then he was in my mouth.

The first few seconds Ashland was sort of in shock. He was on his knees with a sweaty and naked Colby Dennis standing over him. And Colby's dick was in his mouth and his hands had a firm grip on Ashland's head.

That few seconds was all he had to be in shock.

Colby wasn't going slow or easy.

Ashland's senses were overloading.

The first thing that hit him was the smell. Colby reeked of sweaty teenage boy. It was like he had his face shoved into a dirty jock strap. Then the taste hit him. Colby's dick, maybe from the sweat, tasted sweet and salty in his mouth. And the dick itself felt sort of rubbery in his mouth. It wasn't as bad as he expected.

Then he gagged as Colby slammed his head into his crotch. He almost fell over and had to grab on to Colby's butt to keep his balance. He could feel the muscles in Colby's ass and the texture of the hair on his ass cheeks.

Colby winced after that thrust, jerked Ashland's head off his dick for a second, slapped him across the face, and then said, "Watch your goddamned teeth."

The next twenty minutes were a brutal lesson in cocksucking for Ashland.

Colby got hard quick and his dick was at least eight inches. And he had no patience at all for Ashland.

It took him only a minute to realize Ashland had zero experience and couldn't take him hard in that position.

He moved from standing up to relaxing on the couch and watching the porn. He gave Ashland instructions on how to blow him.

He spread his legs and had Ashland lick his sweaty balls clean. Then he had him run his tongue in and out of his foreskin and suck the head as he jerked him off. All of that lasted maybe five minutes.

Colby stood up then, picked Ashland up in his arms, carried him to the mattress, and threw him down on it.

Ashland panicked and said, "I'm on my period. You can't fuck me."

Colby laughed and Ashland realized there was no real way he could stop Ashland from fucking him if he wanted to do it. He was completely at Colby's mercy.

Colby almost growled, "I can't nut from that shitty blowjob. I gotta fuck. If pussy is off the table, then you're getting it hard in the throat or up the ass. Your choice."

Ashland knew there was no real choice there.

He pitched his voice up and said, "Fuck my throat, Colby."

Colby grabbed Ashland's body and twisted it until his head was hanging upside down off the bed, nearly touching the floor. Then Colby knelt in front of Ashland and the mattress.

Colby said, "You understand I got to be rough? No mercy until I nut?"

Ashland nodded and Colby replied, "That's a good girl."

Ashland gagged on the first thrust, but it didn't slow Colby down. In that position, Ashland's throat was as open as it was going to get.

His throat was Colby's pussy.

The next fifteen minutes taught Ashland what it really was to be a woman.

Colby easily held Ashland's hands down anytime he tried to push him off or struggle. Ashland wound up holding on to Colby's ass just to maintain some level of control.

It wasn't much.

Colby would pull his dick almost all the way out and then ram it in balls deep. His nutsack would cover Ashland's nose as Ashland gagged and choked and tried to handle the dick forcing itself into his throat. Sometimes, he'd feel like he was about to pass out. Other times, Colby was in and out of his throat in seconds.

Ashland's whole world for that fifteen minutes became Colby's dick pounding in and out of his throat. Gagging and choking him. Using him as a means to nut.

Part of Ashland was terrified, but part was excited. Like being at a haunted house.

Colby's feelings were nowhere near as complicated.

He kept up a steady stream of moans and comments.

Colby said things like:

fuck...yes..eat that shit...gag on it bitch...choke on it...lick my nuts...I'm churning up a big nut for you baby girl... you're so lucky baby...your throat feels so good...

The whole time he was on his knees really working over Ashland's throat. At one point, he was pounding hard enough sweat dripped off his chest all over Ashland.

Then he came.

The only warning Ashland had was feeling Colby's ass clench, then his dick thrust deeper than it had ever gone. Colby held it there while Ashland felt like he was going to suffocate, then he twitched and cum poured out.

Ashland gagged. He tried to let the cum out, but Colby wouldn't release him.

Colby held his dick deep in Ashland's throat and said, "Swallow...swallow..swallow..."

And finally Ashland did.

Colby's cum was slimy and bitter tasting. But he figured it was a small price to pay for this to be over.

It wasn't over.

Colby stood up after he came and then reached down. He dragged Ashland off the bed by his arms and then flipped him around so he was on his knees again.

Colby ruffled Ashlands wig and said, "Time for clean up, then we're good. "

Ashland had a second to be confused, but then he realized what was going on.

Colby wanted the cum licked off his dick and balls.

Ashland lowered his head, still unused to the smell of Colby's sweaty body, and sucked the globs of cum out of Colby's pubes. He also licked and sucked Colby's balls as clean as he could and tongued in and under and between Colby's foreskin.

Finally, Colby moaned and pushed Ashland's head away. Then he grabbed his shorts and pulled them back on.

Colby looked down at Ashland then and said, "I'd never date an ugly bitch like you, but you're welcome to bend over or open that throat for me anytime I need pussy."

Ashland started to stand up and go, but Colby grabbed his shoulders and pushed him back down.

Then Colby said, "I'm done. You're not. Stay on your knees."

Then Colby shouted, "Dad! Got a bitch here!"

Part Two

Connor Dennis worked at a construction site. He spent 8 hours of everyday hammering nails and carrying sheetrock and whatever other labor was needed. His boss was an asshole and Connor thought about quitting everyday.

The thing that stopped him was Colby.

Colby was his pride and fucking joy. Kid was going to be in the NFL and already got more pussy in a week than most high school boys got their whole four years.

He was a stud.

He also shared some of that nice juicy pune tang with his daddy.

Connor was no asshole though. He made sure all the girls were over eighteen or he wouldn't touch them. Pussy was never worth jail.

Some of the girls were drunk or stoned and excited to have a threesome with a real dad and son. Some were just sluts who were taking all comers. This girl, Jenna, she just loved to suck dick and would take any comers.

Ashland was not like that.

Connor's first thought when he saw Ashland was his son was a fucking idiot. He had clearly just facefucked the kid with no clue what he was. Connor decided he had to handle this himself.

He took off his shirt and underwear and told his son to, "Go make lunch."

Then he made a decision.

Asland looked up from his knees at Colby's dad. Mr. Dennis was at least 6'3 and he was hairy like a bear. He was also built huge. He had a little belly, but he was at least 250 pounds and it was almost all muscle. His dick was at least as big as Colby's , but his balls hung real low. He had to be over fifty because he had salt and pepper hair. Even some of his chest hair was grey.

The second Colby closed the door from upstairs, Mr. Dennis changed.

He lifted up Ashland under the arms and shoved him up against the wall.

Then he put his mouth to Ashland's ear and growled, "I should beat the shit out of you."

Ashland froze.

Then Mr. Dennis reached between Ashland's legs and felt around until he grabbed his still taped dick. Then he squeezed Ashland's balls hard enough the boy winced.

He said, "I saw enough of you in Thailand to know a ladyboy when I see one. But if you want to be treated like a worthless bitch, I'll treat you like one."

Mr. Dennis grabbed him by his right ear and dragged him over to a card table. Then he shoved him face down, so they were both facing the projector screen. It was playing the same porn, but Jenna was being eiffel towered now.

One of Mr. Dennis's hands pressed Ashland's face into the table. The other pulled down the pink panties and hose.

Ashland whimpered, "Please."

Mr. Dennis smiled.

Then he said, "You dress like a whore, son, I'm going to treat you like one. Beat up that sweet young ass pussy."

Ashland whimpered again as Mr. Dennis spit on his asshole and then shoved a finger in him.

It burned and hurt.

Then Ashland felt oil or some kind of lube poured onto his ass.

Then Mr. Dennis laid on top of Ashland. His body was heavy and hairy.

He pressed his face next to Ashland's and said, "This is gonna hurt, boy. Men don't take it easy on sissies, even ones with tight virgin boycunts."

Then Mr. Dennis covered Ashland's mouth with one hand. He used the other to push himself in.

Ashland screamed into Colby's dad's hand.

It felt like his asshole was being ripped apart. As he cried, though, Mr. Dennis moaned.

Connor

I had never banged one of those ladyboys in Thailand. There was too much real pussy there. And all the Thai whores let you in their ass. But this kid was making me almost regret passing them up.

The way he bucked under me and fought while he screamed into my hand and he cried was hot. The sight of his smooth butt cheeks had me half hard before I touched him. And his makeup was smeared from the tears and my boy fucking his throat. It made him look like a real whore.

I liked his build too. He was small like a woman, but toned enough to put up a useless fight.

It made me feel like one of those Roman slave masters must have felt. Powerful and using a boy who should be out banging pussy and nutting on some bitches tits.

And the actual physical way his asshole felt blew my fucking mind.

My first slam barely got three inches in. He was in tears, but I felt like my cock was buried in fucking silk. It was tight and wet and squeezing the fuck out of my cock.

The second slam got me about six inches in and I swear I felt his cherry break. It knocked the breath out of him and it was like I pushed through a second even tighter hole.

But when I went balls deep, I almost lost it. He wasn't screaming anymore, but whimpering like a puppy. It took all my self control not to nut right there.

If you've never had a tight virgin boycunt, you'll probably have to idea what I'm talking about.

But his boypussy was better than any cunt I'd ever had.

It felt like a silky wet velvet glove had an iron grip on my dick. Every inch of my cock felt stroked and squeezed at once.

I had to pause for what felt like five minutes to stop myself from instanutting. I just lay my sweaty body on top of him and explored his body a little with my hands.

At that point, his dick was small enough to almost be a clit. Completely soft.

Every inch of him seemed to have been shaved. He was smoother than most girls.

When I knew my dick could handle it without exploding, the real fun started.

I lifted my body off him and placed one hand on the back of his head to hold him down and still. Then I pulled almost all the way out and slammed forward.

His body rocked and he made an uh sound.

Then I did it again. And again. And again.

Every little whimper and grunt he made made me harder.

I started slamming him so hard the table moved a little bit every stroke. Then I realized I was missing out on a real opportunity.

I lifted his head up off the table, turned it to the side, leaned down, and spit on his face. I watched it run down his eyes all the way to his mouth and then did it again.

Then I slapped his little butt cheeks and said, "Call me daddy and beg me to cum in your asshole, son. I want to cream your sissy asshole, but you got to beg."

He didn't want to do it, but I saw him realize who the boss was here.

He whispered, "Please, daddy, cum in my ass. I want you to cum in my sissy asshole."

I couldn't say no to that.

It took me twenty minutes of solid fucking after that to nut in him. I could have done it in five, but I was enjoying turning the kid out.

What finally got me was something unexpected happening

The kid jizzed.

I had noticed him moving his ass back a little on my dick, but figured he was trying to get it over with. But that wasn't it.

Somewhere between the screens and tears and the cream pie, the kid became a real faggot.

Ashland

Mr. Dennis lifted himself off me as soon as he came. I could feel his jizz in my ass and dripping down and out of my hole.

I stared at his huge dick and couldn't believe I had it in me. All of it.

I felt like I had been hit with a truck. My ass hurt and I could hardly hold my legs together. I pulled up my panties and pantyhose, even though they were going to get soaked through with my cum.

To say I felt awkward was an understatement.

Mr. Dennis lit up a cigar and walked over to me with it lit.

He smiled and blew the sweet smoke in my face.

Then he spoke, in that deep voice of his, and said:

I'm having friends, my age, over for the football game Sunday. I'm in charge of entertainment. Colby will be out of town. Come as a boy, serve us drinks, cook for us, and maybe you'll get some more dick.

He reached under my top and tweaked my nipple.

Then he grabbed me by the head and dragged me close and said:

I don't want my son seeing you again. Ever. I don't want him hanging around any faggots, you understand? I'll give you what you need, but if I see you around him again you'll regret it? Understand?

I nodded.

Then he smiled real big and said, "See you Sunday."

I left, intending never to see him again.

But I was at his door, rock hard, at six in the morning on Sunday.

Maybe he was right. Maybe I was a sissy and faggot.

It hurt at first. It was humiliating.

But nobody had ever made me cum like that. It was worth it. I needed more.