The Melodrama of a High School Crossdresser 1
by Milk Baby

This story is complete fiction. Any and all characters are pure fiction. This story contains homosexual acts between boys in high school. It also involves crossdressing. Please be 18/21 and above when reading. This story is mine, please do not copy/replicate any/all parts of it. Also, keep Nifty alive! Donate!! http://donate.nifty.org/donate.html

Give your criticisms, comments, and reactions to milkbaby.monster@gmail.com =====================================================================================

The day started as it always does for Billy. Go to school, head to his locker, grab his things, and get a faceful of cold hard metal. It was expected. After all, his offender isn't very creative. What he lacked in brains and attitude, he made up for in his looks and his killer body. He was such a hot, sexy, hateable douchebag, Billy always thought.

Leo, the sexy douchebag, leaned into his neck, and whispered into his ear, making Billy shudder. "Morning fagwad. I bet you sucked a lot dicks during the weekend." Billy would've been turned on if Leo wasn't such an ass. Leo was definitely Billy's type. Tall, tan, lean and muscled thanks to basketball. Brusque, manly. A dreamboat but also an asshat. Billy decided to play along.

Billy turned around, looking defiantly up at Leo's towering form. "If you really must know, Leonard, I did. I did blow a lot of guys during the weekend. But let's talk about how you're so obsessed with knowing about who and how many guys I've blown. Tell me, you wanna get blown too?" Billy teased, his tongue seductively sweeping his lips, giving Leo a sly wink. A shocked expression flashed on Leo's face before quickly returning to his signature smug look. "It'd take a miracle and a half before I'll let you suck on this stud rod." Leo replied, his hand snaking down to his bulge, shaking it for Billy. "I mean, just look at it."

Billy looked down at his hand, rolled his eyes and gave Leo the most unimpressed look he could muster. "Stud rod? You're so lame, Leo. You think that'll make me want you? Ha. Try harder." He said snappily, ducking under Leo's outstretched arm beside him, easily slipping into their side before walking away, leaving the taller man dumbfounded. Before reaching too far, Billy looked over his shoulder. "Oh, and for a straight guy, you sure do like shoving guys onto lockers and groping yourself in front of them." He said with a shrug before carrying on with his walk to his first class

Leo stood there processing what Billy had just said. Before looking at the smaller boy and roaring out, "HEY!". He chased the boy down, roughly grabbing him by his backpack and shoving him into another row of lockers. He grabbed the front of Billy's shirt to show his anger. "Now you listen here. I don't take that kind of talk from anyone, and especially not from a fag like you. Talk shit again and I'll give you something to cry about."

"Oh please, what are you gonna do, punch me?" Billy challenged with a yawn. "You could do better."

Leo's nose flared, seeming having the last of it. His hands curled into a fist and backed up into the air, directly aiming into Billy's face. It all happened so fast that Billy barely had the time to react. "Say goodnight fa—"

"I'd drop that fist before I get suspended for 2 weeks and get knocked off the team, If I were you, Greene." A commanding voice boomed behind the two. Leo's fist stopped mid-launch. His knuckle hairs ticking Billy's nose. Leo turned, eyes burning with fury as he sees his P.E. teacher and his basketball coach standing directly behind him. He turned back to Leo, giving him an animalistic grunt before dropping his fist. "This ain't over, Dyer." He announced quietly before walking away, giving him the dirtiest look which made Billy shudder.

Billy shook his head and patted his clothes clean. He gave a thankful nod to Coach Langley before walking away hurriedly to class. That little scene took up to much time. He wasn't the type to be late, and he wasn't going to start now. Now, a little backstory on Billy and Leo. Their little feud started way, way back in their younger years. Believe it or not, these two were actually friends, although not very close. Still, they felt no animosity between them. That is until the 4th grade.

It wasn't even serious. It all started when Billy borrowed a pencil from Leo and never gave it back. It was Leo's favorite pencil, given to him by his late grandfather. Of course, Leo was livid. Billy was defensive, he asked why Leo lent him his favorite pencil. The fight was lost to time because as the years passed, the two always found something to fight about. These two were always clashing and butting heads. All the way to their final year of high school.

Now at both 17, Billy has become the smartest kid in their class. He grew up to 5'8" (his mother assured him that probably grow taller. Probably), thin, but not skinny. He was a small, smart, babyfaced gay, a perfect recipe for the sharks that are his classmates. But Billy never backs down. He always fought back which managed to mostly repel his tormentors. All but one. Leo grew up to be 6'3" total jock. He wasn't very school smart but he gave the school pride and joy. He excelled in every sport which molded his body into something a model would be envious of. He was tall, hot and damn sexy. You could hear panties drop everytime he walked through the halls.

The day ended very uneventful. Nothing else happened between Billy and Leo except for the scene in the morning. They didn't share many classes, and the ones they do share, Leo always seemed to skip them. The only chance Leo's got to go into college was sports, and he was very confident with that.

Billy was very excited to get home. As soon as the bell rang, he ran to his locker, shoved everything inside, shut it and started his run home. His parents were never home by the time his classes end so he was always alone. He ran inside the house, making sure to lock the door. He headed for his room, shut his windows and blinds and proceeded to strip his clothes.

Billy, now in his naked and pale state reached for his dresser. At the very bottom was a locked drawer. He procured the key from a very hidden part of his room, sealed with a special lock. He unlocked the drawer and began to pull it out.

Inside the drawer was various colors, fabrics, and laces. This is the special drawer where he kept all his girl clothes. You see, Billy was a crossdresser. It was a huge fetish for him. He loved to feel the smooth fabric of women's lingeries hugging his delicate cock and big, pale ass. He loved to feel the lace tickling his pink nipples. But more than that, he loved showing himself wearing skimpy lingerie to men on the internet. Crossdressing was his second deepest darkest secret. His biggest secret was that he was a crossdressing camera model.

Billy had clients everyday. Mostly men of an older age. These men pay Billy a handsome sum and Billy puts on a show for them. This day was no different. Billy's client wanted to see him get hard in frilly pink panties while he plays with his ass. And so Billy did. He turned on the camera, making sure to keep his face out of the frame. He leans back onto his bed, his legs spread into a wide 'V', showing his cute bulge and ass in the frame.

Billy starts to gently rub his crotch as the other slowly starts to pull the fabric covering his little hole. Soon, with the panty slid to the side, his puckering hole is shown. The pink pussy seemingly winking at the camera. He licks a finger, making sure to get it wet enough as his hand slowly starts to reach for his hole. He lets out a moan as his finger rubs on his entrance, his knees shaking from the anticipation

He starts to rub his cock harder through his frilly panties as he moans and whines while touching himself. Soon, the finger finds itself crawling ever so slowly into Billy's tight entrance. This finger slowly reaches all the way onto the knuckle, rubbing gently on Billy's sensitive prostate. This caused him to throw his head back and let out a moan. His fully hard cock now peeking out of his panties.

Billy was a modest 6 inches. Although he was a bit thicker than what you'd expect. About 5-6 inches around. He started to play with his cute little cock as his finger thrusts itself in and out of his ass. Billy was now fully moaning and fingering himself. His hand becoming a blur on his little cock as he inserts another finger. These fingers alternate on pressing on his prostate, sending electric waves of pleasure directly onto his cock.

The squelching noise of his jacking hand and his wet sloppy hole fills the room. This along with Billy's slutty moans. He could feel his balls draw up inside him, ready to shoot a load. But before he cums, he stops. The absolute torture of not cumming when he desperately needs to, hurts. But it was what the client required. Damn kinky old men.

Billy sat up, his cock a throbbing, leaking, red-tipped mess. His hole leaking with spit and ass fluids as he lowers his face all the way up to his nose and licks the fingers that he used on himself. Before he shuts off the camera, he speaks in his most sexual, slutty voice. "Thank you, daddy."

Billy ends his little scene and imports the video onto his laptop, still ignoring his throbbing boner. He needed to send this video soon. He was a little late on this client and he didn't want to disappoint since the client paid in advance. He finishes editing the video and heads to his email. He intends to find a better way to send his videos, rather than through email, but this will do for now.

Billy, in a hurry, clicks on the first email on his inbox. He clicks on the reply box and uploads the video with a comment. "Here's the video, daddy. I hope you like this little present from your little girl <3." Billy could only roll his eyes at how pathetic that sounded but it was what the client asked for. He couldn't deny good money

After he finishes sending it, he stands up, takes off his girl clothes, puts on his regular clothes then heads for the washer. He washes his girl clothes himself because his parents would start asking questions. After spending an hour or so cleaning his clothes and eating dinner, he grabs his dry clothes and heads back up into his room.

He shoves the girl clothes back into the drawer, securely locking it before hiding the key again. He goes back to his laptop to check on whatever. A notification pops up, signalling that his email has been replied to. It was faster than usual but Billy checked it anyway. And that was when Billy froze solid.

"What the fuck is this????" was the reply.

The reply was from a Leonard Greene. Dread and panic started to overcome Billy's whole body. How?! How had he sent this to Leo?!

"I'm gonna get you so fucking good, Dyer. You fucking faggot."