Charles in Charge Ch. 07

1996

Autumn

Nebraska

Please note, all characters are eighteen years of age or older.

Charles sat in the library by himself studying vigorously. He had an exam in an hour he didn't want to fail it.

Unlike any test he'd done in the past, this was for his sick and ailing twin sister Charlotte. She had left for a week to get life-saving surgery.

'Focus...' He thought to himself, he was after all determined to succeed in his efforts.

Charles was so determined that he had dressed in his sister's clothes to pass himself off as her!

It worked so well that he conned not only the school, but also his father, his sister's friends, and... her boyfriend.

'Ugh...' Charles grumbled sweeping a hair from his face; it was a hair attachment he wore to make his dark hair look longer.

"Charlotte..." Said a female voice quietly. "I like your dress!"

"Thanks." Charles replied not looking up.

He wore a black sundress with a white t-shirt underneath. He had decided that morning that he was going 'whole hog' in drag until his sister returned home.

'No more being a boy until this is done!' He thought to himself reaching for a calculator.

"What's that?" Asked Lisa, Charlotte's best friend.

"Uh..." Charles said grasping for words. "How was your night?"

"I burned out my vibrator's battery just thinking about him!!!" Lisa said exploding in volume.

"Shush!" Commanded a nearby librarian.

"Uh..." Charles said knowing who Lisa referred to. "That's my brother..."

"Char... he will be mine!" Lisa declared in a solemn tone.

Charles hadn't thought about spontaneous erections when he picked this dress. He now was regretting his decision as his dress was displaying a visible tent under the table. He yearned for Lisa almost as much as she wanted him!

"I have to study..." A blushing Charles said.

"Promise me you'll bring him to the party!" Lisa begged.

"What party?" A perplexed Charles asked.

"The jocks are throwing a party tonight!" Lisa said.

Charles perked up, as a man he never got invited to such events.

"We're invited?" He asked.

"We better be!" Lisa said. "It's for Kurt!"

Charles doubly perked up at this! Dressed as a woman, the two of them had enjoyed several encounters.

"I thought he left already?" Charles asked trying not to sound too enthusiastic.

"Yeah!" Lisa said. "He leaves for the airport afterwards!"

"Maybe I'll go..." Charles said unsure.

Lisa stood up, started to leave then stopped.

"Oh, it's a costume party too!" Lisa said, "so dress sexy!"

With that she departed. Charles took several deep breaths as he contemplated what to do.

'Dress as a man and get with Lisa...' he mused to himself. 'Or dress as a woman and get with Kurt?'

The answer eluded Charles as he buckled down once again to study his little cross-dressing ass off!

After the test Charles wandered the halls hoping to accidentally 'bump' into Kurt with little success. All he got for his efforts were hungry stares from the men of his school.

'Ugh...' Charles groaned as he adjusted his bra. 'It ain't easy being a chick...'

In addition to the leers Charles could hear the whispers of party talk. It sounded like this was going to be quite the event.

"Excuse me?" Came a male voice behind him.

Charles ignored it and marched on, he'd been asked to that very party several times already. He'd even been asked out by Connor, one of his DnD pals.

"Excuse me miss..." Said the voice a second time.

Frustrated Charles whirled about to meet his latest admirer, he'd had his fill of men trying to grope a feel of his ass.

"What!" He barked.

"You dropped your book..." Said a scared chubby kid with a book outstretched.

It was Thomas, another one of his DnD pals. Charles huffed at the geeks chasing after him.

"Thanks." He said snatching it away briskly, not only did he not want his cover broken, he didn't much like Thomas.

Charles turned swiftly away, his hair twirling with him. He didn't want to spend another moment with his fat friend.

"Uh..." Thomas said to the departing Charles. "Did you maybe want to..."

"Nope!" Charles barked out loudly as he marched off in his black Doc Martin boots.

Later at home Charles drew himself a bubble bath so he could shave his legs. He enjoyed doing all these girly things.

His mother never told him how often he should shave his legs, so he did it as often as he liked, which was frequently.

On the radio he had some R&B playing which really set the mood. Although he didn't much have a plan for that evening, he did want to be silky smooth for it.

"Who to seduce?" He mused pointing a leg up to examine it for missed patches.

"Kurt..." He wondered aloud shaving some stubble.

Kurt was muscular tease that made him laugh and even made him cum several times without any contact with his penis!

Charles switched legs; the bubbles flowed down his upraised leg has he pondered his choices.

"Lisa loves me for me." He said admiring his handiwork at shaving. "Plus she's not on a plane for Florida tomorrow!"

Charles felt like a modern Cinderella, however he had two Princes Charmings to choose from before midnight.

Looking first at his finger nails, then his toe nails, before deciding to re-paint them both a bright red; then it dawned on him...

"Can't I do them both?" He said alone in his bubble bath.

Once dry Charles stood in front of his sister's bed fully shaved and naked. Laid out before him was a matching set of silken red bra and panties.

There was also his costume and something else... something new to him.

"How will I get you in?" Charles asked the inanimate object before him.

Charles was certain he couldn't just slam it in like his first plug, nor could he tease it in like the second. He would have to get truly creative!

Grabbing his lubrication bottle Charles greased both his anus and the massive toy. A week ago he would have laughed and wondered how to fit such a thing in his mouth, let alone his ass. Today he was going to discover that answer.

Bending over Charles lined up the huge pillion with his sphincter, then tapped it his other hand.

"Jesus Christ!" He yelled when his ass refused to yield and the toy bounced on to the floor.

His anus was clearly an exit and not an entrance.

Charles cleaned, dried, then set it up for a second go. This time he laid on his back with his legs up on his sister's headboard.

"This better work..." The naked man said to himself as he steadied the monster toy with two hands.

Charles took every precaution prior to starting the second round. He locked both his and Charlotte's doors. He even moved a dressed to prevent an accidental walk-in.

'Getting caught cross-dressing would be easy to explain... it was their idea afterall...' Charles mused to himself as he teased his asshole. 'Explaining this... thing would be challenging...'

Charles had gotten the tip in but no more. It was just too tapered and wide to tease it in. He did however have a weeping erection.

"Ugh!" Charles declared as his bellybutton started to fill with his goo.

"Keep it down!" His father yelled. "I'm watching last night's game!"

"Ah!" Charles eeped as he panicked!

He didn't quite fall off the bed, but he did need to wash the rubber beast off a second time.

Returning to his sister's room Charles set the 'beast' on top of a textbook whilst he used babywipes to clean up his strings of clear jizz.

"That's it!" Charles declared when it came to him.

"Don't make me come in there!" Roared his oldman.

"Uh..." Charles said catching his breath. "Everything's ok in here... how are you Daddy."

"Ugh!" Yelled his father. "I need to rewind it now! Keep it down in there!"

Sensing that time was limited Charles tossed out the wipes then started to milk himself into his palm.

Re-greasing the toy for a third time Charles knew it was for the last time. He had more than enough of his 'home-brew lube' to cover the beast from top to bottom.

Using the last of his man goo to butter his butt-hole Charles started to squat.

"Oh yeah..." He said lining up the plug with his brown star.

Squeezing his eyes tightly Charles imagined that he was impaling himself on Kurt and not a thick rubber toy.

He shifted his hands to the bed as he controlled his descent.

It felt unlike any experience he had felt before! He had jerked off a million times, and yet this was a greater joy. It felt more intense then all the pleasure he had experienced by making Kurt cum.

Charles teased his hole as it relaxed to absorb the toy below him. He raised then lowered his ass down each time further than the last.

"Ungh..." Moaned Charles in ecstasy as he took more.

It really did feel like Charles was giving the lapdance of a lifetime! With each movement up and down all six inches of Charles ivory rod bounced around, oozing it's natural lubricant.

"Oh..." Charles exclaimed when he felt the text book touch his ass cheeks.

"Ooooohhhhh!!!!" Charles subsequently exclaimed as he watched a volley of cum eject from his piss slit.

'It's all the way in!' Charles thought to himself as he savoured the moment.

Catching his breath Charles looked around his sister's room and especially the mess of jizz he'd fired on himself.

"I need another shower..." He joked standing up.

Several hours later Charles walked up the driveway towards the house in red running shoes. He didn't feel brave enough for high heels.

"Whoa..." He remarked passing dozens of parked cars and many people streaming towards the house. "This party is huge!"

Charles wondered if he'd even know any one at the party let alone find Lisa or Kurt.

'Maybe I'll bang whomever I find first?' He wondered before gasping, "What?"

Inside the house he spotted several of his DnD buddies. Connor, Oliver, and Brain huddled in a corner out of costume, looking like nerds staring at all the ladies in slutty outfits.

'What are they doing here?' Charles wondered as he continued to walk by.

Charles was doubly happy that he both wore a mask and that none of them knew Charlotte. He liked being around them as Charles... just not when he was cool, popular and dressed as his sister.

His mind wandered off to what would happen next week when he was permanently a man and they were the only friends he had left. He also worried what had happened to his level 10 elf character!

He passed by a sitting room that seemed to be doubling as a cloak room. Charles didn't have a coat and wouldn't have stopped until something caught his eye. Movement in a dark corner perked his attention.

A soft moan drew him in like a sirens call; aside from his spank mags and the odd porno film, Charles had never seen other people having sex before. He was very curious about sex positions.

In the low light of the quiet room he could see a chubby man grunting as he banged a petite tanned woman with shoulder length brown hair from behind. She was kneeling on a chair moaning.

'Felicia?' Charles wondered as he panicked and tried to silently make his escape.

Charles didn't much like her, and could only imagine who the fat fellow was.

"Lookin good!" A tall jock said to Charles snapping him back to reality.

It was Tad, one of Kurt's football friends, and... a total jerk. The giant jock had given Charles enough wedges, wet willies and cups of cheese to last a life time. Ignoring the brute Charles continued on.

"You can audition to cheer for my team any day!" Tad said slurring his words.

Charles debated about taking Tad aside and blowing him. Although he didn't like the dark haired jock, he was after all a single woman out for the night. He could blow a dozen players and no one would ever suspect it was him or... even Charlotte!

Charles stopped at a floor to ceiling mirror to admire himself.

He was dressed as a cheerleader in a white and red design. The skirt was short, very short. He had knee high socks that accentuated his legs. The shirt was tight, so tight that Charles had trouble getting it on over his padded bra.

Charles could hear Tad talking up another woman, but he ignored all that as he twirled in front of the mirror. If there were a prize that night for sexiest costume he knew he'd win!

He self admiration was interrupted again by Tad nearby.

"Give me some sugar baby..." Tad said to the lady nearby.

"Thanks for the drink," The woman said. "I'm not interested in more."

Charles recognized the voice... it was Lisa! She however looked very different, dressed as a nurse with long blonde hair Charles suddenly realized that he wasn't the only master of disguise!

Not waiting to see what Lisa would do next Charles approached with furry and anger. Using the same trick Kurt had used on him the day he dry humped him when he was dressed as a man, Charles kicked Tad behind the knee.

When the giant dark haired man was off balance Charles shoved with all his sissy might!

"Oooommmffff!!!" Tad groaned as he took a face plant.

Several people who turned to watch started clapping. Even Lance and Britney cheered, they were the power couple at the school; Lance the head quarterback and she the lead cheerleader. Charles despised them both.

"Come on!" He said grabbing Lisa's wrist. "Let's go before he gets up!"

Lisa followed his lead as they pushed their way through the crowd. He could hear Tad roaring, but it wasn't getting louder.

Spotting the staircase Charles lead her up them, then seeing an open door he went in. Closing it after them he pulled her behind the bed.

"Thanks Char..." Lisa said slurring her words.

"Shush..." Charles hissed.

The door pushed open, Charles could only make out the shape of the giant jock. He doubted he could tackle him a second time, so he held his breath.

The door closed and it was followed by a roar of anger. Perhaps they lost him.

Alone in the dark this was the moment he'd been waiting a lifetime for!

"Charles I don't feel so good..." A groggy Lisa said.

"Lisa, I'm Charlotte." Gulped Charles as he tried to tread lightly. "Are you ok?"

Lisa leaned in for a kiss and when Charles dodged, it turned into a hug. He worried that he would screw up not only his costume, but a potential relationship!

"It's ok." He said patting her on the back. "You're just drunk."

"I don't remember drinking that much..." Lisa said.

"It's alright..." Charles said.

He could feel her heart beating against his own. Her breath was just as shallow.

"I'll get you a cab." Charles said helping her up to sit on the bed.

"Call your brother," She said. "I don't feel safe without him here."

Charles gulped. He didn't know how to do that. He had brought a mini purse with make-up pads and fresh eye lashes. He didn't have a set of men's clothes around.

"Hello?" Charles said into the phone as he called for a cab.

"It'll be half an hour." Charles said hanging up, he could see she had taken a nap.

"Ok..." The sexy nurse mumbled.

Charles took a moment to look her up and down. She was a real goddess! Her legs were just as smooth as his own. Her low cut nurse outfit however showed real cleavage.

He was not only sporting an erection, but he was smitten with her! He no longer wanted to be a woman, a cross-dresser or Kurt's girlfriend. He wanted Lisa!

'But how...' He wondered.

"What's that?" Lisa moaned.

"Um.... Want a glass of water?" Charles suggested.

"Sure." Lisa said in a tired tone.

"Close your eyes and rest." Charles said. "I'll be right back."

"Don't return unless you have Charles..." Lisa said dreamily.

He had no doubt of her words. Standing up Charles made his way towards the ensuite bathroom.

Stopping at the dresser Charles took a chance and opened a drawer.

'Men's clothes...' He thought to himself smiling.

Grabbing a handful of garments Charles went into the bathroom.

"Hmmm..." Charles said admiring what he had taken.

There was a pair of pants, an undershirt, a plaid shirt and...

'One sock?' Charles said holding it up.

Charles quickly pulled off the cheerleader outfit, folded it nicely and placed them in the cabinet under the sink. The clothes were all too big for him, but that was alright as he didn't need to wear them for long.

"Ugh!!!" Grunted Charles as he withdrew the giant beast from his anus.

"Ugh?" Charles remarked realizing that the butt-plug looked bigger than he remembered!

He then looked around for a place to hide it! It wouldn't fit with his hidden clothes!

"Hmmmm..." Charles pondered before deciding. "Right here!"

He set it down in a corner beside the toothbrush, then missed it immediately! Charles' anus felt empty! He wished he could have kept the plug in, but Lisa would surely notice...

Charles then washed his face and removed his hair extensions. Usually he got very excited going from man to woman, and bored and frustrated going back as a man. This time he was incredibly excited!

Looking in the mirror Charles looked like a man again. He still had red finger and toe nails, his face make-up however was all gone.

Smiling at his reflection Charles filled a cup, turned off the light, then opened the door.

"Charles?" Asked a groggy Lisa.

"Yes." Charles replied holding his pants up with one hand.

Lisa perked up at this, then taking a breath she tried to play it cool. Charles grinned widely in the dark.

"Charlotte told me you needed help..." Charles lied as he moved closer.

"What are you doing here?" Lisa asked.

Charles knew that the other nerds were at the party, but didn't know why.

"Uh..." He started to say, then remembering his nerd friends downstairs he said. "We all got invited."

"Oh?" She said accepting the cup and the excuse.

Charles really didn't know what do next. He had experienced Kurt's moves, but didn't know which one to use. With a dry mouth and a blank mind he sat down next to Lisa.

"How are you feeling?" He asked with a dry, cracked voice.

"Much better thanks." Lisa said.

Charles realized he had used up all his moves, and decided to improvise. Moving closer to Lisa, he put his hand on top of hers on the bed.

As if she sensed him making a move Lisa moved closer to Charles. Unable to blink Charles somehow mustered the power to inch his body nearer to Lisa.

"Looks like I gotta do this myself!" Lisa said pushing Charles on his back.

"Omhf!" Charles grunted with all the air pushed out of his lungs.

Lisa straddled his hips then leaned down to kiss him. Her breath tasted like alcohol and something else. He kissed her back as passionately as she did to him.

He moved his hands dumbly from his sides to Lisa's hips.

'Oh yeah.' He said to himself realizing that they weren't dancing, but rather making out.

Reaching up he roughly touched her breasts over her latex nurse outfit. The sounds of rubber squeaks got so loud they both paused to laugh.

Lisa sat up to undo her outfit, Charles could barely see in the low light her black padded bra. It looked very similar to the one he hid in the nearby bathroom.

Hungry for more he reached up to lift her bra up. For a moment he worried that she might be like him, a dude in a chick's clothing! However when her tits popped out he was pleasantly surprised.

"I want you Charles..." Lisa said between sweaty kisses.

As they French-kissed Charles couldn't tell if he could taste cum on her lips. He wondered what would her reaction would have been if he had blown a random man and had cum breath of his own.

Charles really didn't know what to do. He fondled a breast, as he squeezed her ass as they kissed, unsure how to proceed.

Lisa slid off him; when she tugged at his pants it reminded Charles of his last time with Kurt... when he gave football player a blowjob.

"No underwear?" Lisa teased. "What sport do you play?"

"I'm a gold medalist in the sex Olympics!" Charles joked as he wondered why she knew about the no underwear rule for athletes.