Charles in Charge Ch. 04

Autumn 1996

Nebraska

Please note that all characters in this story are 18 years of age or older.

'I feel like shit...' Charles said himself as he made breakfast for his father.

He especially didn't like the pomp-pomps attached to his sister's socks. Whenever he walked they bounced back and forth on his ankles.

'Sooooo gay!' Charles thought to himself.

He was also very frustrated with his lot in life. He had been dressing as his sister to write her exams, all while she was off getting desperately needed surgery.

He liked helping his sister, but being a girl sucked! He did all the chores in the house; cooking, cleaning, laundry... the list went on and on! The worst part was he was dead certain he was dating her boyfriend!

"I can smell his scent on me!" Charles said to the frying eggs.

"What's that princess?" Charles father asked.

Charles didn't even have to change his voice to fool his old man.

"Oh..." Charles said scrambling for an excuse. "The eggs smell good!"

"That's good sweetheart." His father said. "Say did you catch the game last night?"

"No Dad... er Daddy." Charles said, he spent his night being dry humped by his sister's boyfriend until they both came at the same time.

"Jordan did really well!" His father exclaimed.

Charles paused. His father never talked basketball, it was only football, and even then it was only their hometown team.

'Is he having a stroke?' Charles wondered turning off the stove.

"Do you think we'll ever get a b-ball team?" He asked Charles.

Charles didn't want to turn around... he was too worried about what he'd see.

"Daddy..." He said taking a breath. "There will never be a Canadian basketball team, the market's too small."

"Pfffissshhh!!!" His father said laughing. "We could do three teams! Toronto, Montreal, Vancouver!"

Charles almost smashed the plates on the ground! Here he was in drag pretending to be his sister and his pops is worried about... basketball!

Charles spun around and tried not to yell.

"Daddy..." He started calmly. "There won't be another pro-level French team..."

His father shrugged.

"Also, why are you acting so weird!" Charles yelled not able to hold it in.

"Wha?" His father said faking surprise.

Charles knew his pops was holding back!

"Tell me the truth Daddy!" Charles barked, knowing full well what he held secret from his own father.

His father went red then lowered his head. Charles felt so bad... he was the one telling the lie.

"Ok pumpkin. I'll spill the beans." His father said head still down.

Charles almost held his breath in anticipation. His mind raced at the possibilities! Did his father know the truth about him? Was he deathly ill like Charlotte? Was he having an affair!

"There's this kid at your school..." His father began.

Charles opened his mouth then covered it with a hand! Was his father sleeping with someone he knew!

"That I want you to invite over for dinner..." His old man said continuing to tell his story slowly.

'Someone is pregnant!' Thought a bewildered Charles.

"I heard he was in Chicago..." Continued his father.

Charles was more confused than before.

"Just say it Dad... er Daddy!" Charles snipped. "I do have to go to school at some point!"

His father looked up, red face as ever.

"The boys at work want to hear about how he met the whole basketball team there." His father said. "You're popular at school, can you ask him over."

Charles almost laughed! He wasn't popular, even in his DND group he was the nerd!

"Daddy I'll try... but I can't guarantee anything." Charles said convinced that it wouldn't work.

"Excellent!" His father replied. "Now how about those eggs!"

Charles moved back and forth placing food on the table; all the while cursing the pomp-pomps on his socks.

"So who is it?" Charles asked sitting down.

"The one on the basketball team." His father said with a mouthful of eggs.

"Um... which one Daddy?" Charles said in growing frustration.

"The one who can play." Was the response.

Charles almost swore, but he actually knew who his father was speaking of!

"Tyreese?" Charles asked.

"Is that the black one?" His father asked.

"Yes Daddy..." Charles replied.

Later that morning Charles was making his way through the hallways of the dorm cursing his sister's pomp-pomps with every step. He also didn't like the way his bra itched his shoulders, or how his lower back now ached.

"Being a chick sucks..." Charles mutter to himself.

He did like the knapsack purse he wore that day. He also wore a plaid skirt with a white button up shirt untucked. Everyday had now become costume party, but it was a deception unlike any other.

'I look like I'm headed to a Halloween party dressed as a slutty school girl!' He thought to himself pausing at a mirror.

In the reflection he saw some men leering at him causing him to make haste. He didn't want to fend off unwanted attention... he was however getting very used to the looks he was getting!

Charles mused on the adventure he was on... it was like he was entering a labyrinth leading towards a wizard's lair. Instead of orcs and goblins he faced jocks and preppies just itching to fuck him, or worse yet to beat him up if they discovered his secret.

He was certain that Tyreese was the wizard when something caught his eye.

"Hi Noa!" He said passing a very frumpy looking girl.

Noa didn't reply as she hastily passed, she seemed flustered and red faced. Charles then remembered that Charlotte most likely didn't know her and became flustered himself! How could he explain it if she did stop to talk!

Charles paused when he saw that Tyreese's door was open. He wouldn't say that he was friends with the African-American basketball player, but he was friends with his roommate Oliver, who was one of his DND pals.

KNOCK KNOCK

Rapped Charles on the door while he awaited a response.

"If it's anyone other than Noa then come in! If it's Noa then GO AWAY!" Bellowed a deep African-American voice.

Charles stepped into the wizard's lair with trepidation.

"Hi Tyreese!" Charles called out as he entered the room.

"Come on in," Tyreese said with his back to him.

Charles looked the room over it was tidy with two TV's beside each other and on the wall a signed black and red sports jersey. Tyreese was tall and muscular, his skin was the colour of coffee with a hint of red. His build was different than Kurt's who was more stocky.

'A wizard's lair full of treasure and wonder...' Charles thought to himself before clearing his throat to speak up.

"Um..." He said composing himself. "Did you want to come over for dinner?"

"Sure," Tyreese said distractedly. "What you making to eat Charles?"

"I got some steaks set aside," Charles said then gulped.

"Yeah?" Tyreese asked, he seemed to be pacing about. "You got some tatters to go with that too?"

Charles finally found his courage and ran to the door, closing it swiftly.

"What's wrong with you Charles?" Tyreese asked impatiently. "I mean aside from those tacky pomp-pomps?"

"How did you know?" Charles said in a near-tear filled panic.

"Ha!" Tyreese said. "Come on man! A white boys dresses up and gets surprised when someone calls him out on it!"

Charles didn't know what to do! Tyreese figured him out in the blink of an eye! And he seemed distracted too! What happens when someone stops to look at him for real!

"What tipped you off..." Charles said sullenly and defeated.

Tyreese smiled as he replied. "Yo! One doesn't live on the streets of Detroit without being not able to tell a hood-rat from a N-"

"Ah..." Charles interrupted. "I get it, I think."

Charles tried to fix his skirt as his penis stirred. He had no idea why Tyreese knowing how to ferret out cross-dressers out had turned him on.

'Wizard indeed!' Charles reflected to himself.

"So what else you got cookin tonight?" Tyreese demanded.

Charles mentally shook his head then explained his dinner plans.

"Sounds good, see you at five?" Tyreese asked.

"Uh yeah." Charles said. "Um why are you coming by? I mean we don't really know each other."

"Two reasons." Tyreese said. "Firstly Oliver knows good people,"

Charles blushed at the compliment, his penis did its own salute.

"Second I'm hungry!" Tyreese teased. "I'm on the student meal plan with no money!"

Charles sighed in relief. He wanted to make his father happy, and it looked like he'd done it! Something however still nagged at him, Tyreese seemed defensive and it wasn't because of him.

"Tyreese..." Charles said. "Is something bothering you?"

"Nah! It's nothing." Tyreese said.

Charles had developed enough female intuition to tell when he was being sandbagged.

'This wizard won't defeat me!' Charles mused to himself.

"I can keep a secret if that's something you're worried about." Charles said.

"Shit!" Tyreese said smiling in delight. "You're right! You can!"

Charles blushed again, his penis started weeping in his drawers. He knew it wasn't sexual tension, but his cock refused to hear him.

Growing up Charles hometown had many people from the Caribbean. Black people weren't exotic creatures to him. Regardless he was glad he wore that skirt!

"Sit down." Tyreese commanded.

Charles sat. His dick strained in his sister's panties.

Tyreese moved closer then stopped. Charles looked up at his soon to be dinner guest... their eyes met.

In the corner of his eye Charles could see that Tyreese was lowering his shorts... and like all the other athletes at his school, he wore no underwear!

Charles looked down at Tyreese's giant black appendage. Although it was soft, it was bigger and longer than his own fully erect!

Squirming in his seat Charles' own penis strained to grow as long as the black snake staring him down. Charles gulped when it all sunk in!

'Did Tyreese expect me to suck him off!?!' Charles wondered as he looked at the thick delicious dark sausage before him.

"Oh my!" Charles exclaimed when he finally saw it.

"Yeah..." Tyreese agreed.

The tall black man hovering over him wasn't seeking a blow job! He was seeking a second opinion!

"When did it happen?" Charles asked.

"Uh... recent." Tyreese said.

Charles wondered if frumpy Noa was the one who botched the blow job. Her teeth didn't seem a jumble of spikes, but the evidence was pretty strong that she did.

"I've had that happen before." Charles offered.

"Don't kid me..." Tyreese said shooting him a glance.

Charles gulped before giving his own confession. "I did, or something similar jerking off without any lubricant."

Tyreese nodded as he spoke. "So what did you do?"

"I kept my hands off it for two weeks, kept it clean." Charles suggested.

"Good to hear." Tyreese said taking off his shirt.

Charles almost came in his pants! Tyreese was muscled with a very visible six-pack. Although the black man couldn't use his manhood for anything, Charles brain wouldn't accept that.

"Uh..." Charles said mouth agape.

"Don't worry princess." Tyreese said. "I'm going for a shower... alone."

"Oh yeah..." Charles said his penis quivering. "I knew that."

"Whatever!" Tyreese said kicking his shorts away.

"Uh... before you go." Charles stammered. "I gotta ask you something."

"Go ahead princess, it looks like we is both good with secrets." Tyreese declared standing completely naked just mere feet from Charles.

Pulling off his knapsack purse Charles produced the small black rubber object that had been haunting him. He left the lubricant inside the bag.

"What is this?" Charles asked.

"Yo!" Tyreese said laughing, his thick black penis bobbed about! Charles couldn't blink!

"Come on!" Charles pleaded. "Please tell me!"

"Yo! That's a butt-plug!" Tyreese said taking in a breath.

"A what?" Charles said.

"I ain't gay, and I ain't playin with no chick who uses one." Tyreese stated. "But some folks put them up their ass for fun."

Charles blushed heavily! His cock let out a drop of semen, and the butterflies in his stomach exploded!

"I'm gunna go get that shower." Tyreese said turning away. "You can show yourself out right?"

Charles nodded, his mouth was too dry to formulate words. He couldn't help but look at Tyreese's ass. It was so unlike a woman's bottom.

'Chicks are so soft and round...' Charles dreamed, 'his is so... muscular and tough...'

"Hey princess," Tyreese said causing Charles to cough in panic. "What you got for drinks?"

Charles wanted to say gin and juice, or Colt 45, but decided to go with honesty.

"Just my Dad's supply from back home." He said.

"Proper!" Tyreese declared excitedly, causing his black snake to shake. "We used to drink that stuff in Detroit to prove how brave we was!"

Tyreese turned again to walk away, Charles found his breath and more importantly his courage.

"Cucumber!" He said causing the black man to stop.

Tyreese looked over his shoulder interested.

"Tell her to practice on a thick cucumber..." Charles said speaking faster, "or a banana."

Tyreese smiled then turned to the bathroom. Once in he stuck his head out to speak to Charles.

"As a dude, you weird..." The caramel coloured man said. "As a chick... you alright."

With that he closed the door and started the shower. Charles stood there waiting, his body controlled by his smaller head.

When he was certain Tyreese was in the shower he pulled down his sister's panties to his knees. He then grabbed the black rubber butt-plug and coated it and his fingers in lubricant.

Bending over he first moistened his ass crack, then applied it directly to his anus when he realized how dumb it was to lubricate his whole crack!

Holding his breath he plunged the soft rubber object into what was once an exit.

"Unh!" He grunted as it went in.

He felt full! That and all his senses were exploding! It was an electrifying sensation all over and not just his anus.

The butt-plug also unlocked something else in Charles. His mind awoke to the fact that he was in someone's room in his sister's clothes, panties around his ankles with a boner and something up his ass!

Charles pulled up his panties, his dick refused to obey, it leaked a string of clear jizz that coated his hands, and got on his clothes. It all turned into a mess as he hurried out the door!

Not knowing where to go or what to do, Charles dashed down the hallway in a waddle. The butt-plug made every step uncomfortable.

"Men's room!" He decided without a thought.

Moving about the hallway Charles wondered back to his DND day-dream. It did feel like the wizard cast an enchantment on him... his front and backside did feel magical!

"I just need to sit down and catch my breath!" He said to himself as he moved along like a cowboy.

Seeing the door, he pushed it as he ran inside. It wasn't until he bumped into a tall muscular man did he realize that he was in the men's room! And most importantly he had walked into Kurt!

The collision knocked all the air out of Charles lungs! He struggled to stay on his feet! Kurt helped steady him, Charles tried to say thanks, but found Kurt's lips on his own!

Charles didn't fight it, Kurt's lips were soft... not quit the same as a woman's but if he closed his eyes it didn't matter.

Kurt pulled him close, then like a man breaking his fast he pawed Charles all over. Charles relished all the attention he was getting! Only when Kurt cupped his balls did he eeep!

"Aaaahhhh!!!" Charles said into Kurt's lips as his nuts were fondled.

Kurt's hands moved elsewhere, it was if he remembered Charles was on his 'period'.

The two kissed and explored one another as they moved deeper into the washroom. Charles didn't know where they were headed... nor did he care.

Kurt's hand went to Charles hip, then to his lower back. His already pounding heart beat faster! He dreaded the thought of Kurt discovering the butt-plug buried in his bowels!

Charles' hands and fingers explored Kurt. He didn't see this as gay, he was just curious. He felt up Kurt's abs, then his muscular pecs, shoulders and arms. His instincts told him to grind his groin into Kurt, he wanted to cum sooo bad!

Charles couldn't decide if Kurt were an ogre sent by the wizard to catch him, or a brave night come to rescue him the... princess?

'Ah fuck that!' Charles thought to himself forgetting the DND comparisons.

They ended up in a toilet stall. Charles closed the door behind them then resumed kissing. He had no clue what was going to happen next! Kurt had pinched both his nipples repeatedly; to Charles it felt like a bizarre purple-nurple contest.

He felt up the blonde haired jock too, exploring his body. Kurt must have grown tired of that as he grabbed Charles hand and placed it on his groin.

"Oh FUCK!" Charles mumbled into Kurt's mouth.

He had felt Kurt's dick several times, but this was different, not only was he awake this time, but he was in control! He squeezed and Kurt's cock flexed in response.

Kurt seemed to have frozen still when Charles hand moved up then down.

'It's not gay...' Charles assured himself. 'I jerk off all the time, I'm just doing it for him.'

With such a justification Charles went... crazy! He lifted his hand up, then dove into Kurt's pants.

'No underwear ever!' Charles remarked to himself.

Kurt sat down on the toilet, then stood up again to pull his pants down to his ankles. All throughout Charles gripped the blonde athlete's penis tightly.

"Suck me beautiful!" Kurt said with a smile.

Charles opened his watering mouth then lowered it towards the thick white appendage. Kurt's smile always seemed to cast a spell on him! For the second time that day he had a massive dong stuck in his face.

'OH FUCK!' Charles realized as he stopped mid-way.

He could feel the heat of Kurt's manhood looming in his face. He however could not proceed! He saw what an inexperienced cock-sucker could do! Poor Tyreese had the injury to prove it!

The last thing he wanted was to do a terrible blow job and expose his... secret identity.

"I'm...." Charles said raising his head up, "on my period."

Kurt burst out laughing as Charles commenced with a regular and methodical stroking up and down.

Charles was blushing in embarrassment that he couldn't do what was asked of him. The laughter however set him at ease.

'Kurt is a decent fellow!' Charles mused as he jerked his sister's boyfriend off.

'Wow!' Charles thought. 'This was the closest I've ever been to another cock!'

He hadn't even seen his own that close! Charles could see pulsating veins, Kurt's cock wasn't bigger than Tyreese's, but both athletes were much larger than himself.

'I got an idea!' Charles thought to himself before speaking up.

"Close your eyes." Charles said.

Kurt grunted an affirmative, they were already shut. Charles rummaged out of his sister's purse the sex lube and applied a liberal amount to his hands, then started stroking anew!

"Oh fuck!" Moaned Kurt.

Charles felt emboldened, he reached under his skirt and fished his own dick out of his sister's panties. If someone told him last week that he'd be jerking off two cocks at the same time he wouldn't have believed them, now... he was actually doing it!

"Feels so good..." Kurt said.

Charles was so fired up as well! He had to slow down on his own ivory stick. Cumming at the same time as Kurt didn't cross his mind, but now that it had, it was now his goal!

Jerking Kurt off was so different than stroking himself off. Not only was the football player longer and thicker, but the way Charles gripped the other man's appendage was vastly different than how he held his own. It was... backwards.

"Oh fuck!" Kurt said. "I'm close!"

Charles jerked faster on both Kurt and himself! He was determined to have simultaneous volcanic eruptions!