The Melodrama of a High School Crossdresser 2
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

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

Billy was shaken. How the fuck was the video sent to Leo? His mind was a crazy, panicking mess as he quickly shut his laptop, almost too forcefully. His breathing quickens as he lays on his bed, in the dark, thinking about what just happened. He thought about so many scenarios when he comes to school tomorrow. Maybe Leo would forward the e-mail to every single person in school, even the teachers. Or, he'll take screenshots, print them and post them all over the school. Or maybe he'd even post it on the internet. So many scenarios, all of them leaving Billy shamed for the rest of eternity

Billy was laying on the bed, staring at the ceiling and praying to every god out there to at least make the whole shaming thing quick, when his phone suddenly vibrated and lit up. A notification. Someone had messaged him. Oh god. It's probably a family member who's seen his video which is probably spreading all over the internet lile wildfire. Why the fuck did he have to show his face? He breathed in deep, mentally preparing himself for the message. He opens his phone and checks who it's from

Message from: Leonard Greene

Curious, dumbfounded, and relieved, he opens the message.

meet me behind the gym tomorrow. after basketball practice. be there.

A follow up message suddenly popped up.

dont even think abt ditching me, dyer. this video is a click away from spreading all over the net.

Blackmail. Damn. Billy didn't have a choice. He had to get into college with a clean record. He resigned to himself to meeting Leo tomorrow. He was thankful that he hadn't spread the video everywhere. It was a bit of a surprise seeing how much they hated each other's guts. Maybe Leo had a nicer side to him. The thought almost made Billy gag but he imagined a gentlemanly Leo helping an old lady cross the street. It was so laughable that he laughed himself to sleep.

On the other side of the suburbs, Leo was sitting on his desktop, watching the video. He had come home earlier, tired after his practice. He saw that Billy Dyer had sent him an email with an attachment. Since the two didn't talk much, he had gotten curious and opened the message. He clicked on the video and went wide eyed.

The video shows the lower area of a male. Although Leo could not believe it was male. The skin was pale white. Pristine. And the ass, it was almost too perfect. The person was also wearing the most revealing underwear. Sexy lingerie with ruffles and fluffs. And then there was his hole. Leo has never seen such a pink hole. His throat dried up which made him swallow as his eyes were glued to the video. He could feel his cock growing in his jeans. Why was this turning him on? He was straight for crying out loud.

Leo could hear the moans and the whimpers of the male as his finger crawls to his hole. It was very feminine. Leo unconciously licked his lips as the male's finger slowly inserted into his puckering hole. His hand began to stroke his cock, which Leo hadn't even noticed. From then on, the male was fully fingering himself with one hand while the other was a blur on his cock. Leo wanted to stroke himself but his eyes were glued to the video. He was frozen solid on his seat.

Leo could feel the person's impending orgasm. He sees that his cute little balls (Leo mentally slapped himself for calling another guy's pair of balls "cute") draw up into him. But before he could fully shoot, he stopped. Leo could see his reluctance. Leo was also a bit dismayed. He would've like to see an end to this show. But whatever.

Suddenly, after a few seconds of recovering, the male started to sit up and shows his face on the screen. Leo froze and went wide eyed. It was Billy. Billy Dyer. Leo could not believe it. He was stunned, but his eyes remained glued on the screen. Billy began to lick the finger that was inside him. This made Leo gulp again. Then in Billy's sluttiest voice he says "Thank you, Daddy." And then the video ends. Leo was stuck staring on the screen. What the fuck had he just seen. And why the fuck was his cock so hard that he'd blow if he saw that video again. It didn't make sense. Billy was crossdressing cam model? And why had he sent the video to Leo?Why did he call Leo daddy? And the most important question of all, Why the fuck was Leo so turned on?

Leo was pissed. He was pissed at Billy for turning him on like this. He decided to reply. "What the fuck is this????". But it didn't feel enough. Leo was still infuriated. He had to get revenge on that faggot. He had to be punished. Leo was suddenly coming up with plans on how to torture Billy. He tried to ignore the ones where Billy was tied up in his lingerie with a well lubed hole, waiting for Leo. No. He did not want to fuck Billy. At all. Period. "I'm gonna get you so fucking good, Dyer. You fucking fag."

After deciding what to do with Billy, he sends a message saying that he wants to meet him after school. Leo thought that Billy might bail out on him so he made he sure he comes using a little blackmail. And Leo lef left it at that, showering and falling asleep, weirdly getting excited about meeting Billy the next day. He falls alseep with a semi and several images of Billy tied up.

Billy was afraid to go to school. His nerves were so wracked that he almost didn't come. His perfect record was scratching at his brain which forced him to go. Leo apparently has kept the video a scret and has not spread it yet but his paranoid mind kept saying otherwise. Every step he took he felt like his knees would buckle and he'd collapse. He was so damn nervous. Eventually, he reaches the front doors of his school. Whatever. It was his final year in high school anyway. Soon he'll ditch this bumfuck town to live far away. With other gays. With a deep sigh, he enters his school. He holds his breath, preparing for the worst.

Nothing was out of the ordinary as Billy heads for his locker. Teenagers chatted amongst themselves, paying Billy no mind as always. He expected that the second he enters, he'd be tackled to the ground and every single member of the school body would give him a solid punch each. It was dumb but his paranoid brain somehow convinced him it would happen. But nothing has happened causing an amazing feeling of relief washing over him. That is until he sees the foreboding figure of Leo. Almost immediately their eyes meet. Leo's eyes were dangerously mischievous. Billy was already mentally preparing himself for whatever scene this ape of a man will cause.

Billy was waiting. His fear building up as Leo neared him. His grip on his locker's handle was tightening he was afraid it would literally turn to dust. Any second now his life would be over. Leonard's steps seemed like the only noise that Billy heard. Time seemingly slowed to a painful crawl. Here he comes.

And then, nothing. Leo simply passed Billy with a knowing look. A warning, it seemed. It sent shiver down Billy's spine. But as Leo walks away from Billy, another amazing feeling of relief washes over him. He'll live for another day. For now.

Like yesterday, Billy's day was uneventful. But instead of running home to change to his lingeries, Billy heads to the back of the gym, waiting patiently for Leo. He's curious about what Leo wants with him. He sits on the grass, leaning against the wall, just staring at the sky getting lost in thought. He was processing this whole situation.

"What the fuck are you doing, weirdo?" Billy suddenly hears a deep voice, shaking him out of his daydream. He shakes his head and quickly stands up, nervously looking at Leo. "Wha-uh, nothing... uh, nothing. S-So what'd you want with me, Leo?" Billy asked with a nervous voice. This made Billy chuckle as he looks down at the shorter boy. He leans forward to his face, "Not so tough now, huh. Dyer?" Leo says tauntingly and pokes on Billy's nose, which causes Billy to shake his head and huff angrily.

Leo laughs out loud and begins to walk towards the front of the school. He then turns Billy with a slightly annoyed look "You comin' or what?". Billy snapped back to his senses and walked behind Leo, following him to his car. He wanted to comment on how nice it was but he didn't want to speak to Leo anymore than necessary. "Get in." Leo commanded, with Billy following. He didn't know why he was so obedient to Leo. Probably because of the blackmailing thing. Right.

"You know, for a little cunt you sure are easy to boss around." Leo laughingly said as he watches Billy get in. Billy could only roll his eyes as he impatiently asks "Where are we going?" "You're house." Leo answered and Billy was surprised. "What?" "I said your house. Now give me your address." Leo said as he turns his key, the engine roaring. "What? Why?" Billy asks with a little bit of worry in his voice. "Oh my fucking god so many questions! Just give me your address! Shit." This shook Billy, scaring him a little. "F-fine." He reluctantly answers and gives Leo directions to his house.

Leo starts heading to Billy's house. The whole ride was quiet and a bit awkward, but Billy nor Leo were ready to start a conversation with the other. A little while later, the both reach Billy's house. "So did you just drive me home?" Leo gave him a look. "What? Fuck no? We're heading in? Your parents home?" He asks as he shuts the engine. "No, they don't go home until late." "Perfect, get out." Leo says as he exits this car. Billy exits as well, awkwardly standing beside the car, unsure of what to do next.

"What the fuck are you doing there, get us in the damn house." Leo said, his anger rising once again. Billy was quick on his feet. He heads for the door, opening it for him and Leo. Once they were both inside, Leo was looking around, uninterestedly looking at the interior as Billy was locking the door. Suddenly, Billy felt a bit insecure about his house. Did Leo have a better house? Was it bigger? Probably. "Where's your room?" Leo said, suddenly breaking the silence. "Uh, upstairs first door on the left." "Great, let's go." Leo yanked Billy to the stairs and pushed him in front, making him lead.

Soon, both teens were inside Billy's room. They both drop their bags. Leo stands on one end of the room, crossing his arms. "Strip." This caught Billy off guard. "What?" "Ask another question one more time and I'll knock your teeth out. I said strip." Billy was shocked and afraid. Why was Leo making him strip. But he liked his teeth where they were so he turned around, his back facing Leo as he starts to strip. Soon he was bare naked, blushing, his pale bubble butt facing Leo's observing gaze. He's never been concious of his body. Until now.

"Now I want you to change into your lingerie."

Billy froze solid once again. He looked over his shoulder and sees Leo's menacing face. And what seemed like a growing bulge .

"Now faggot!"