Charles in Charge Ch. 06

1996

Nebraska

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

Charles awoke in his own bed for the first time in what felt like ages! He stood to stretch feeling like a man!

He then went to the bathroom to brush his teeth, his mouth felt like he had done a blow-bang for six men!

Afterwards he found that getting dressed in his own clothes was so fast and simple!

"Shirt, sweater, jeans..." Charles said getting it all out for himself.

"Oh yeah!" He remarked spotting the larger and thicker butt plug.

He found it the night before and wondered intensely if it would even fit?

"Only one way to find out..." He said as he lubricated first his anus, then greased the big object.

"Uhn...." He grunted pushing up.

The first attempt was a failure, but quitting wasn't his motto. Charles squatted more then teased his anus repeatedly. First circles around his star shaped hole then dipping it in slowly followed by pulling it back out.

"Oh yeah..." He purred as each push resulted in more of the toy in his bowels.

When it was all the way in Charles was rock hard and his penis started weeping clear jizz. It reminded him of Kurt's own member producing a ton of it!

That was enough to snap him back to reality! He finished dressing as he ran out of the house. For the first time in a long while, Charles wasn't late for the bus!

He had jammed Charlotte's clothes and some make-up in a bag, he planned on going to the school early to study in the library, then change right before the test. Afterwards he'd change back and return home. He was not in the mood for dealing with people.

As Charles waddled down the hallway, with his massive plug jammed in his rear, he noticed something incredibly eerie! No one was looking at him!!!

'Am I wearing a ring of invisibility?' He mused looking at his fingers.

Usually men ogled him and woman shot jealous daggers with their envious eyes! Today the crowds didn't part and no one seemed to notice him!

After a quick stop at his locker Charles spotted Oliver with Brain his tutor walking down the hall. Both were members of his DND group, he waved excitedly.

"What?" He pouted as they blew past him speaking in hushed tones as if they were discussing a conspiracy.

Charles closed his locker deciding that it was best to leave them to their own devices.

As he walked down the hall Charles felt one set of eyes on him! Looking around he couldn't quite place it...

"Charles?" Called out a voice down the hall.

Charles at that moment wished he did have a ring of invisibility! It was Kurt!

"Oh shit!" He declared as he didn't look back and tried to blend into the crowd.

Being pasty white with brown hair Charles assumed he could merge into the crowd at his Nebraska Community College!

Picking up his pace Charles didn't want to talk to Kurt. He had given the big blonde football player both a handjob and a blowjob the day before dressed as his sister!

The butt plug hindered him greatly! As he increased his stride his fear grew that he would pop it back out!

Instinct took over as he dashed around corners! He pulled off his sweater hoping that a change of colours would throw off Kurt. It truly felt like he were being pursued by a cyborg sent from the future!

'Ladies room!' He thought to himself as he made his escape!

Charles pushed the door open and stepped inside.

"I made it!" He breathed between heavy breaths.

"Excuse me!" Said a female voice to him.

Charles looked up to see Lisa, his sister's best friend!

"Um... hi!" He said before remembering that he wasn't dressed as his sister, and... in the ladies room!

"What are you doing in here?" The thin petite girl asked sternly.

"Uh..." He said sweating. "I don't know!"

Charles felt sweaty and filled with fear! He also fought the urge to push on his butt plug to prevent its ejection from his body.

Lisa fluffed her pixie cut hair as she took a step towards him. Her face displayed anger, her eyes however showed something else...

Panicking Charles opened the door and ran away! He was willing to take his chances with Kurt!

"Oh shit!" Charles said running as he remembered that the last time he faced Kurt as a man the jock dry humped him!

"Get back here!" Yelled Lisa behind him!

Several hours later in a different bathroom Charles was still panting even with the door locked! He had successfully evaded both Kurt and Lisa, oddly enough they were also the only two people he could see himself being intimate with.

Charles huffed in frustration at his dual life! He had two people who wanted to fuck him, however he had to dress and act a certain way for each.

"I'm not so sure about Lisa now..." Charles wondered aloud as he applied his eye liner.

Charles felt confident enough now with his make-up that he could let his mind wander. He was so shocked when Lisa raised her voice at him.

He removed, cleaned, then re-greased his butt plug. Aside from feeling comfortable inside him, it had now become his good luck charm!

After a final look in the mirror Charles adjusted his breasts, then fussed his now longer hair.

"I really do look like a chick!" He said to his reflection before leaving in despair.

As Charles walked down the school hallway he could feel the eyes of every man upon him once again! He was invisible ten minutes previously, now he was dead certain he was being locked into several future mental spank-banks in the minds of the men who leered at him.

He had once felt scared by those same looks as men gazed at his chest, or stared at his ass. For a while he enjoyed the sensation; today however it caused him unease.

'I don't want to be a girl any more...' He sulked to himself.

That night when he got home, he stripped naked then showered without shaving his legs. He then dressed as himself and studied at his own desk.

"I won't dress as Charlotte unless I have a test to write!" He pledged as he struggled to learn her course in a night.

RING RING RING!!!

"Ah!" a startled Charles yelled as he fumbled for the phone.

"Get the phone!" Bellowed his father, who had wisely left him alone that evening.

"Hello?" Charles said answering.

"Tell them the game is on!" His old man yelled.

"Excuse me!" Demanded a female voice on the phone leaving Charles extremely flustered.

"Lisa?" Charles asked.

"Listen hear Mister!" Declared the woman on the other end. "Don't you try to play games with me!"

"I won't..." A worried Charles tried to say as she continued on.

"Good!" She stated firmly. "Now get me Charlotte, and don't you dare dilly-dally!"

Charles had already broken out into a sweat as he rushed to his sister's room and picked up.

"Hello?" He said trying not to sound winded and scared.

"I'll wait..." Lisa said firmly.

"I got it." Charles said to no one.

He then hung up the second phone in his hand completing the ruse.

"Charlotte?" Asked Lisa.

Charles sat on his sister's bed and was shocked when he realized the plug was still wedged in his ass! He supressed a grunt as he tried to focus on the phone.

"Yes..." Charles said rolling his eyes as he spoke, he hadn't changed his voice once since picking up.

"You won't believe what happened today at school..." Lisa said in a conspiratorial tone.

"What happened?" Charles asked dreading the answer.

He wasn't sure what Lisa would say! Did she call campus security... the police! Charles didn't want to go to an American jail!

"It was AMAZING!!!" Lisa shouted into his ear! "He walked into the bathroom and we talked!"

"He who?" Charles asked confused, he knew it was himself, but he didn't understand her excitement.

"Charles..." She said dreamily.

"Um..." Charles mumbled. "He's a boy, why would he be in the ladies room?"

"He was pursuing me of course!" Lisa declared proudly. "He knew I was in there and he marched in all sweaty and handsome."

Charles didn't remember things quite like that, he was trying to escape Kurt.

"Lisa..." Charles said. "Are you sure he was looking for you? Maybe he got lost?"

"Psfsh!" Lisa exclaimed brushing off his words. "His eyes said it all! I could see nervous anticipation!"

Charles wanted to laugh! If he was only slightly slower he would have gotten laid! Lisa continued in great detail about what she wanted to do!

Charles could only sit in discomfort as his cock grew in his shorts. As Lisa described how wet her pussy was.

"I swear one night I will sneak into his room and make him mine!" Lisa declared defiantly.

Charles panicked! Surly Lisa would want to see Charlotte after a sexual encounter with him, or worse she visits Charlotte first before visiting him.

"Uh..." He said trying to buy time. "Could you wait until after exams"

"Sure!" Lisa said before saying, "after that... he's all mine!"

"That works for me!" A relieved Charles said.

After that Lisa let him go.

Charles was exhausted! He wanted to jerk off! Lisa had good him revved up! He wanted her almost as badly as she wanted him!

Sleep however over took him before he could get is ivory stick out and beat it. His sleep was deep and dream free; his old bed felt so comfortable and natural.

TAP TAP TAP

Charles awoke with a startle! He worried it was burglars... or worse Lisa! He wanted to have sex, but what would she say if she noticed a giant black butt plug buried in his anus!

TAP TAP TAP

Rang out a second time.

"Ssssshhhhh!!!!!" Charles hissed as he fought his blankets to stand.

He left the light off, he didn't want to awaken his old man. His father didn't seem to care or notice that he was now a man, he might however be upset by a late night disturbance.

Standing Charles was suddenly sprouting a very stiff erection, his body new that sex was afoot! Lisa had come to see him!!!

"Hello?" Whispered Charles as he cracked his window.

"Charlotte?" Asked a masculine voice.

"Kurt?" Charles asked.

"Yeah, let me in." Kurt said.

Charles gulped, his cock quivered! He wanted to slap his pearl covered member for betraying Lisa so quickly!

"This is Charles." He said.

"Twins!" Kurt quipped.

Charles rolled his eyes in the darkness at how his sister stupid boyfriend was.

"Go away." He said to the jock. "I'm sleeping."

"I can't," Kurt said. "Your sister won't answer me."

"Uh..." A nervous Charles said. "She's sleeping."

"Yeah right!" A sarcastic Kurt replied. "I saw her running from me after her test, she's mad."

Puzzled Charles wondered if the jock was half-blind?

"You did?" Charles asked.

"Yeah!" Kurt protested. "You did too! What's up?"

Charles wanted to mention how Kurt had dry-humped him as a man, and coerced him into several handjobs and a blowjob as a woman. He however stayed silent.

"Come on buddy..." Kurt pleaded.

'Ugh!' Charles moaned to himself, he couldn't resist this football player in the dark or in drag!

"I was... uh... late for something." Charles said.

"Late for the ladies room!" Kurt teased.

Charles gasped, then laughed softly along with Kurt, it was a silly day.

"What do you want?" Charles asked hoping to get rid of the blonde man before he received a face full of dick.

"I'm only here until the weekend." Kurt said. "I don't want to leave on bad terms."

"Leave?" Asked a confused Charles.

"Yeah," Kurt said. "I'm only here for a semester, then back to Florida."

When a startled Charles didn't reply Kurt asked, "didn't you know?"

"No..." Charles replied open mouthed.

It all made sense to the brown haired cross-dressing twin. His sister broke up with Kurt because she knew she'd never see him again. Charlotte had done the same with a boyfriend back home, pen-pals and long distance were not her thing.

"Uh..." Charles said into the dark. "I'll go talk to her."

"Thanks buddy!" Kurt said sticking his hand in to muss his hair, Charles almost screamed, his cock threatened to fire off!

Stumbling in the dark Charles struggled to remove his clothes and put his sister stuff on.

"Charlotte..." Hissed Kurt from outside.

Naked with his anus straining under the plug he found a bra, panties and a long sleep shirt. He had seen Charlotte wear the same garments in the past.

"Shush!" He said trying to get hair extensions in.

Charles knew he wasn't looking sexy, and he was fine with that. He planned on letting Kurt say his piece then send the muscular jock away.

"Hello?" Charles said opening his window a crack.

"Charles?" Asked an anxious Kurt.

Gulping in fear Charles wished he had put on some make-up!

"No..." He said with trepidation. "It's Charlotte..."

Silence followed his reply, Charles bit his lip nervously, and adjusted his breasts.

"Twins!" Kurt said laughing.

"What do you want?" Charles said then regretted it.

Kurt proceeded to pour his heart out to Charles in the dark like a modern Romeo. The blonde jock didn't say the word love, but he did imply it strongly. Charles unused to such romantic attention fell for it!

"You better come in." He said opening the window further.

For a giant Kurt had no trouble wriggling inside. Charles gulped again when he realized the only possible outcome to the footballer entering... It was a metaphor for what the big man planned to do to his vagina... the only problem was Charles didn't possess one!

"Uh..." A worried Charles stammered. "I'm on my period..."

Kurt ignored his words as he moved closer to Charles in the dark. Charles wanted to run! The giant man however was on him quickly as he wrapped his arms around him.

"Thank-you!" Kurt said hugging Charles.

"Uh..." Charles stammered. "You're welcome."

"Good-night." Kurt said letting him go.

In the dark Charles could feel the warmth leaving his flesh from where Kurt had embraced him. An hour before he wanted to be a man, now he wanted to be a woman!

"Kurt wait!" He said in a low tone.

"Yes?" Replied the blonde athlete.

"Kiss me one last time." Charles said trying not to sound lame.

Kurt returned to embrace him tightly, pressing his lips onto his. The peck turned into two kisses, then a battle of tongues.

Kurt pressed his massive erection into Charles, causing him to gulp! He tried to very hard to keep his own erection away from the larger man.

Charles had never taken dance class before, but he knew the importance of taking the lead. After several encounters with the jock he knew the brute would grope him all over and in doing so cup his balls.

"Lay on the bed." Charles whispered.

"Okay..." Replied the blonde man as he moved back.

He had once seen a porno just like this very moment. In the movie however the woman was actually a chick and not a twin trying to pass himself as his own sister.

Charles didn't dwell on the fact that he was now a cross dressing cocksucker, he instead focused on the moment. He lifted Kurt's shirt and kissed his stomach.

"So firm..." Charles mumbled as his lips touched abs.

His next kiss was lower, he felt soft hairs tickle his lips. His next kiss lower involved more hair. Charles knew what a treasure trail was and where it was leading him. He had a peach fuzz version of one last week. Kurt's however was much different... more manly.

Trying something different Charles guessed where Kurt's cock head was and opened his mouth to place it over. Unlike previous encounters he used his teeth to gently bite the outline of that thick penis head.

"Ungh..." Grunted Kurt.

Charles then kissed Kurt's belt, followed by an attempt to undo it with his teeth with no success. He might be an impressive cocksucker, but a human belt remover he was not.

Opening Kurt's fly, he could feel the heat emanating from the muscular man's groin. Charles own penis quivered in anticipation, he could feel it weeping his seed into his silken panties.

'Never any underwear' Charles mused to himself as he lowered his face into the glowing furnace that was his sister boyfriend's penis.

His plan was to kiss the cock head gently, then to lick the shaft. Charles wanted to explore the larger man in the dark. Kurt however had other ideas.

Kurt reached up with the speed and power of a man who pushed down other men for fun. He grasped a fistful of Charles hair in an instant.

"Ungh!" Emitted from Charles, who didn't resist.

Kurt held his head firmly as he lifted his own cock up to Charles waiting mouth. Even if he didn't want a mouthful of man-sausage it was too late.

Holding him steady Kurt raised and lowered his hips aggressively fucking Charles mouth. Charles relaxed his jaw to take all of it, it was a sensation unlike any other!

Charles could feel his mouth producing saliva In quantities he couldn't have imagine before that day! It all helped with lubrication that giant white pole ramming into his face.

The way Kurt fucked his face it shook Charles butt-plug. It almost felt like he was getting railed from both ends.

'What if that were Tyreese behind me...' Wondered a very horny and cock hungry Charles.

His dick quivered and shook as he face got fucked. Although he had two free hands, he used them to prop himself up.

"Uuuugggghhhhh!!!!" Grunted Kurt as quietly as possible as he came straight up and into Charles mouth.

"Gggguuuuggggghhhh!" Charles moaned as he tasted the now familiar taste of Kurt's fluid shooting at his tonsils.

Charles swallowed as much as he possibly could, however gravity worked against him. He could feel jizz rolling across his tongue and through his teeth.

"I'll get you something to clean up with." Charles said standing back up to breath.

Kurt yawned in response.

Once alone in the bathroom Charles felt like he had pissed himself!

"Wha..." He declared in astonishment when he saw he had came at the same time as Kurt!

He quickly wiped his own jizz from his panties, changed his pads, then brushed his teeth. Remembering Kurt he got a face cloth and moistened it with warm water.

Returning to his sister's room he could see Kurt on his back snoring. His thick manhood hadn't shrunk yet.

"Hmmmm..." Charles wondered aloud as he debated blowing the passed out man.

He instead cleaned the jock up.

"Charlotte..." Moaned an exhausted Kurt, "come join me."

Yawning Charles climbed into his sister's bed to snuggle with the giant man. Kurt embraced him with his arms then fell back into sleep.

Charles squirmed as he tried to lie in a way that didn't involve his own dick pressed again Kurt. Perhaps Kurt sensed this as he laid on his side, Charles did the same becoming the little spoon.

"Ugh..." Charles moaned as Kurt pushed his residual erection into his ass driving the butt-plug even deeper.

Blinking repeatedly Charles managed to suppress an orgasm induced from his new found toy.

Unaware of the looming drama next to him, Kurt slid an arm under Charles head, then draped his other across the man dressed in women's clothes. In a brief moment of lucidness the jock stuck his hand down Charles oversized shirt to pinch a nipple. Never one for a purple nurple, Charles squeezed his eyes shut as a coping mechanism.

"Uuuugggghhhh...." Charles mumbled as he came a second time in his panties.

Snuggled as he was Charles refused to get up and change, preferring to shut his eyes to join the snoring beast behind him.

Awakening with the dawn Charles was startled when he realized that he was alone!

Charles didn't know what to do first? Remove that uncomfortable itchy bra, look for Kurt, or just go back to sleep...

"Kurt?" Charles said to an empty room.

"Princess!" Called a male voice from outside the room. "You better get ready if you want a ride to school!"

Charles gulped! That was his father! Looking in the mirror he could see how much of a mess he was! His hair was all astrue, as was his make-up!

"I look like a Halloween freak!" Charles said.

"What's that?" Asked his father.