The Melodrama of a High School Crossdresser 3
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.
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Billy stared shocked at Leo. The very fact that Leo wanted to see him in his lingerie was beyond belief. Add to that, he had a boner. But knowing better than to anger Leo, he proceeded to grab a small box from behind his closet, grabbing the drawer's key from there. Billy couldn't look at Leo as he walked to the dresser. Not only because he was naked, but also because he was a bit fearful of Leo at that very moment.

Bully started putting on a pink lace bra and g-string. The panty barely overed his cock and the string for his ass went inside his crack. Totally embarrassed, Billy reluctantly turns to Leo for what to do next. What he saw then caused him to panic. Leo was holding his phone up, aiming at Billy, presumably taking a video, all with a menacing grin.

Billy was afraid, pissed, but overall scared for his future. Leo was getting more material for blackmail and to possibly ruin Billy for the rest of his life. It was pathetically easy. "L-LEO! WHAT ARE YOU DOING?!" Billy exclaimed, running to Leo and trying to grab the phone. Leo, thanks to his towering height, easily raised the device out of reach for Billy. "Woah, chill. I was just... documenting our little encounter. Just to make sure you won't bail out on the little deal I have for you."

Billy stopped reaching for the phone, looking at Leo with cautious eyes. "A deal?" "Mhm." Billy was reluctant but he let Leo speak. Leo sat on the bed, looking at Billy with mischief in his eyes. "You see Billy, what you're doing right here, is fucking sick. It's disgusting," Leo said with disgust laced in his voice. Billy suddenly felt ashamed and wanted to cry right then and there. "The smartest thing to do right now is to expose you on the internet and ruin your life," Billy knees buckled, collapsing on the floor, ready to bawl his eyes out. "But," Billy suddenly looked at Leo. "Maybe I'll save your ass if you agree to meeting here every after practice and put on a show for me?"

Billy was shocked. Leo wanted to see him wear lingeries? What the hell? "Wait, what?" "You heard me. Now you can either agree and we'll keep this a secret between the two of us, or, you don't and you get ruined. It's a no-brainer, really." Leo said, looking smug and just evil as he looks down on Billy, patiently waiting for his answer.

Billy had no other choice. He wanted to get out of this town with a clean record and a good name. "...Fine." "Great! Oh, I forgot to mention. Along with putting a show for me, you'll also be sucking my cock. Maybe even more. Let's start now." Leo announced, unzipping his pants and taking out his semi-erect cock.

Leo was waiting for Billy as the boy stared at his cock, almost like he was in a trance. Billy's mind blanked out. He didn't know what to do. The truth was Billy was a virgin. He'd never seen another cock so up close, much less suck one. He had no idea what it was like sucking cock. And now here it was, the cock of his own tormentor, patiently waiting for him to suck it. "Get a move on or I'm forgetting about the deal." Leo said with impatience in his voice.

Billy gulped, moving closer to Leo's spread legs. He'd always dreamed about sucking cock, but not like this. He didn't want it to be like a hostage situation. But he had to do what he had to do. Billy grabbed Leo's growing shaft, looking up at Leo. Leo looked down at him, mischief and lust mixing in his eyes. "Come on..." Leo urged, watching the petite boy dressed in skimpy underwear hold his cock.

Leo could not believe that he was here, his cock being stroked by Billy Dyer dressed in lace underwear, but here he was. And he was liking it. A lot. He'd focus on those issues later. For now, his cock was about to be sucked by a crossdressing faggot.

With a shake of his head and a deep breath, Billy followed his instincts. He started to slowly slide Leo's cock into his mouth, which has now grown into a full 8 incher with a fairly thick girth. It was going to be challenging but he had to do it.

Billy closed his eyes as he started to suck on Leo's engorged red tip. He was sucking on that spongy head, his tongue circling around it. He made sure his teeth didn't touch any part of Leo's shaft. His tongue was lapping up at Leo's piss slit. He was naturally drawn to the taste of Leo's precum. He started sucking harder, hoping to draw out more. This caused Leo to suddenly groan and breathe heavy. "Shit, yeah, just like that." Billy suddenly felt like a pro cocksucker. He was apparently a natural at this.

Billy started to bob on the upper half of Leo's cock. Slurping and sucking on it. The sounds of cocksucking filling the room. He was stroking the other half of Leo's shaft. Leo was now full on moaning, his arms supporting his body as he looked down on the boy expertly sucking on his cock. His had started to reach for Billy's hair, holding onto it lightly as Leo was slurping on his hard shaft. Leo's precum was flowing freely, making Billy savor each and every drop.

While Billy was busy collecting Leo's sweet fluid, Leo's hand grew tighter on Billy's hair. He was feeling his impending orgasm and he wanted to make it good. Suddenly, with a shaky, heavy voice, Leo announced to the sucking boy. "Enough of this slow shit, I'm fucking your throat. Ready or not, faggot." Billy was surprised as his hand was slapped of Leo's shaft. Suddenly, Leo's pulled Billy off of his cock by his hair. "Open up fag, here I come."

Billy's head was then pulled down onto Leo's cock, the thick member shoving its way deep into Billy's tight throat. Billy gagged, his spit flying everywhere. This only seemed to turn Leo on as he began to thrust his his up, his cock suddenly thrusting in and out of Billy's throat. Billy held on tight onto Leo's thighs for balance as the bigger boy started thrusting faster. Leo's balls began hitting Billy's chin as his thick cock slid in and out of Billy's throat.

Billy was gagging continuously, tears started streaming down his face as the bigger boy forgot about Billy and only focused on making himself cum. Leo's balls suddenly drew up inside him. It was coming. Leo could feel the impending intensity of it as he was fucking Billy's throat relentlessly. "Here it comes faggot. Shit I'm gonna fucking cum. Fuck. FUCK!!!" And swiftly, Leo pulled out his cock from Billy's throat, several strings of spit forming between his shaft and Billy's lips.

Billy, finally catching his breath, was surprised as sudden rope after rope of thick cum coated his face. Leo was moaning loud with every shot, aiming it on Billy's face, then down to his lingerie. Seeing his own cum splatter all over the slutty lace turned him on even more. Billy could only watch as Leo coated him with thick, white, piping hot cum.

Soon, Leo's orgasm died down. He was spreading his cum on Billy's face, panting and catching his breath. "Shit." He said quietly. Billy was uncomfortable. He felt dirt as Leo spread his seed using his cock all over Billy's face. Leo then looked down, seeing Billy's cock peeking out of his lace panty which was splattered with cum. "Fuck, you must have really like that look how fucking hard you are." Leo said with a grin. Billy looked down, seeing his surprising arousal and blushing, biting his lip.

"Play with yourself." Leo said in a low voice.

Billy looked up at him, still biting his lip. He wanted to play with himself so bad. He hadn't noticed but he was very horny. "Do it, faggot." Billy let the lust take over. He falls onto his back as he starts stroking his cock through his panty. His eyes closed his mind focused solely on making himself feel good. He then hears the deep voice of Leo again. "Play with your hole too." Billy couldn't help himself as his fingers crawl to his pink boy hole, covered by a mere string.

Leo was getting hard again. This was the video he had seen, but now he was seeing it in person. He forgot about being pissed because all he could focus on was how good Billy's hole looked as he played with it. Seeing Billy's dainty fingers suddenly disappear into the tight pucker. His cock was now at full mast as he watches the boy pleasure himself. His cock leaking precum as he hears the boy moan, his hands going faster on his cock as he fingers himself.

Billy was lost in the pleasure. His fingers naturally found his prostate which they are now rubbing and stroking against. Billy was letting out breathy moans as his hand strokes his cock, using his precum as lube. His little balls begin to draw up into his body. His orgasm was coming. His moans started to get more frequent and become much louder. Leo started to slowly stroke himself as he watches the little nerd get swallowed by the pleasure.

Billy let out one last moan before suddenly shooting high up in the air, surprising him and Leo. His cum landed on his face, then on his bra, mixing with Leo's own cum. Billy kept cumming. He kept shooting ropes of cum, landing it all on him. Leo stroke himself faster. The image was too hot for him to ignore. Seeing the little faggot in his sexy lingerie fingering himself and cumming was too much.

Billy's orgasm soon comes to an end. Leo then stands up, still stroking his cock, looking down on Billy with his signature mischievous smile. "I'm cumming again fag, ready or not." Leo then let loose his second load. It was thinner and much less copious than the first, but he still managed to cover Billy's face and get his lingerie.

Zipping his pants back up, Leo headed for the door. "See you tomorrow faggot." Leo left, not looking back at Billy and slamming the door. Billy was still on the floor, recovering from what possibly was the best orgasm he's had. Minutes later, still on the floor, Billy could hear Leo's car leave. Billy snapped back to his senses, still covered in cum. He was wondering what kind of situation he had gotten himself into. "Jesus, I'm so fucked." Billy said to himself with a defeated voice.

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