Charles in Charge Ch. 03

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Dressed as his sister a back massage goes awry!
4.7k words
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Part 3 of the 8 part series

Updated 06/10/2023
Created 09/02/2021
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Autumn 1996

Nebraska

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

Charles awoke with a stiff erection yearning for attention!

"You gotta wait!" He said walking to the shower. "You've caused enough problems!"

He had awoken early so he could get ready, his one make-up session was not enough to make him a pro by any means.

After his shower, he made a point of using menstrual pads. Although he was a dude and had no use of them, he figured that after the close call he had the night before he'd rather have someone goose him and feel a pad than feel his nuts.

Sitting down at his sister's make-up table Charles stared at the small black rubber item on a shelf nearby. He loved mysteries and riddles, the more intricate the better!

He knew it wasn't a hair or make-up accessory, it also wasn't a paperweight.

"Or is it..." Charles said applying his eye lashes.

He lifted up his foot and inserted the item between his big toe wondering.

"Where are the other nine?" Charles mused with a laugh.

At breakfast his father was still quiet, his pops was usually very chatty at meals discussing recent football games. If his team from back home played he was especially animated, today... silence.

Charles preferred it; he was after all dressed as his sister and pretending to be her in order to write her exams.

"Charlotte, want a ride to school?" His father asked.

The school was no where near his father's work, it sent his heart pounding! Was his old man going to call him out on his ruse?

"Sure Dad... uh Daddy." He said stumbling over his words. "Let me finish cleaning up."

"Ok kitten." His father replied. "I'll be in the car."

Charles didn't like that now that he was playing the part of a girl that he was also a maid! He did however didn't want to take the bus with anyone who could uncover his big lie.

As soon as he sat in the car he changed the radio station from sports talk to hardcore rap. 2PACS last recorded song was on! The famous rapper was gone, but his music lived on. Charles couldn't help but sing along!

"What's with the music?" He father said above the tunes.

Charles froze! His blood went icy as he remembered that he liked gangster rap, and his sister liked pop music.

"Oh yeah..." He said changing the station to something with the Spice Girls playing.

Despite the music it was as if a cloak of silence had covered the car! Charles couldn't handle why his pops was so odd!

"Miss your brother?" His father said.

"No!" Charles said too quickly, he took a breath and tried again. "I guess Daddy, I guess I miss Mom and him."

Charles forced himself to breath normally as he thought to himself. 'Maybe that's why pops is so weird?'

"Do you miss them too Daddy?" Charles asked trying to draw it from his father.

"Miss them?" His old man scoffed. "They just left last night."

Charles pondered that on the rest of the drive to school... in silence.

Walking into the school Charles pushed thoughts of his father's weirdness from his head. He needed to convince a school he was Charlotte, and most importantly pass all the exams!

His clothes drove him crazy! Charles tried to walk, but his bra straps itched, his panties rode up his ass. The pads made his nuts sweat and the short skirt left his pale white legs freezing! He hated being a girl!

The looks freaked him out the most! He passed a group of three men and all of them stopped talking to look at him!

'I've been found out!' Charles worried.

He passed several men at lockers and they all gawked at him too!

Charles took a breath to evaluate the information he had. When he looked at the men staring, none look at his face. They all stared at his chest, a few his legs. When he glanced over his shoulder many were seen admiring his ass!

"I'm not a fraud!" Charles mused. "I'm HOT!!!"

Charles strutted down the hallway eating up the glances! He wished it were women checking him out, but to him admiration was admiration!

Men would smile at him, nod or wink. Charlotte warned him about all this. He remained aloof as he passed them by. He didn't make eye contact, or respond to any advances.

"Oh snap!" Cried out a female voice nearby.

Charles' instinct was to dive for cover, the last time someone came at him he was dry-humped until he came! With no avenue of escape, he stopped to stand his ground.

"Charlotte!" Said the voice much closer. "What happened to you?"

Charles looked to see Lisa, his sister's best friend at school. He knew he needed to bring his A-Game to pull this one off.

"Whatever do you mean?" He said, then regretted for sounding so pompous.

"You look like Tyreese facefucked you hard!!" Lisa exclaimed pulling Charles by the hand to the bathroom.

Charles laughed as he followed; he had gotten an instant erection! Lisa's touch was electric! He was certain that it was from her touch and not the mere mention of the schools only black basketball player.

They entered the ladies room and Charles eyes grew wide! As if he were wearing a ring of invisibility Charles strode forth.

He expected to see naked woman walking around! Instead he was greeted by an empty room that smelt vaguely perfumy.

'Some ring of invisibility...' Charles thought to himself as he glanced about looking for tits and noticed... the lack of urinals?

'Where do they stand to pee?' He wondered as they stopped at the mirror.

Lisa placed her giant purse down then set to work with make-up brushes.

"Your choice of colours is so weird!" Lisa said. "Did you awaken colour blind?"

Charles was stumped, he did have normal vision but he had no clue what he was doing! Instead of getting into a make-up debate he decided to change direction.

"Kurt and I are broken up..." He said trying to sound sad.

"Aw, that's too bad." Lisa remarked as she redid Charles lip gloss.

"Yeah..." Charles said. "I want to focus on my studies."

"How's your brother taking it?" Lisa asked looking Charles in the eye in the mirror.

Charles gulped! Lisa hadn't even said hello to him, let alone ask how he was doing?

"Um... he's taking it well...." Charles said unsure how to proceed.

"Poor guy." Lisa said. "He really looked up to Kurt."

'Huh!' Charles wondered. 'Kurt dry-humped me then tricked me into a handjob!'

"Yes... he did." Charles said fishing for words. "They were... very close..."

"Aw!" Lisa said with genuine concern. "He needs a hug!"

"Kurt?" Charles asked.

"No silly!" Lisa teased. "Charles!"

Charles was stunned! He wanted to say more! He wanted to draw out more information! Lisa however packed up her stuff and made her way to the door.

"Come on! Let's go Charlotte!" Lisa said enthusiastically. "We got a test to write!"

Charles caught up to Lisa in the hall, which was difficult as he was still sporting a boner.

"Say Lisa." He said. "I got this thing in my room and I don't know what it is."

"You speak like your brother sometimes!" Lisa teased before saying. "Twins!"

Charles gulped, she covered up for him unknowingly! He however wanted information.

"I think Kurt left it behind." He said lowering his voice. "It's not a... well a..."

"A what?" Lisa whispered back now curious. "A sex toy?"

"I dunno." He said back. "It's small and rubbery."

"Hmmmm," Lisa replied. "I'm have too see it."

Charles wished he had his mother's Polaroid photos. He opened his mouth to say more, but a loud voice cut him off.

"Next!" It boomed.

"Tell me about it later!" Lisa whispered. "We gotta get checked in."

Charles heart pounded as he stood in line. He didn't think the young man checking ID would believe him.

"Next!" The young man said.

Charles stepped forward with shaky hands. He presented his sister's student ID. The man struck her name off the list without looking up.

"Next!" The man said.

"That's it?" Charles said.

The man fogged Charles words as he said, "NEXT!"

Charles took the hint and moved on into the gymnasium.

Later at home he was exhausted! The test went well, he made dinner for his father, cleaned up...

"Women's work never ends..." He sang to himself cleaning up.

Charles didn't notice the person sneaking up on him until it was too late! He almost leapt to the ceiling when he felt hands on his hips. The hands were large and strong holding him still.

"Guess who?" Said the voice.

"Aaaaahhhhh!!!" Cried Charles before saying. "Why do you insist on startling me!"

Charles was no fan of Kurt's sneaky tactics, it resulted in a dry-hump followed by a hand-job! Kurt was much too smooth for Charles.

"I've never startled you before today..." Kurt said moving closer.

Charles couldn't escape, not only did Kurt have him firmly secured, but he remembered to his own shock that Kurt dry-humped Charles, not Charlotte!

"Well don't ever do it again.... Ugh..." Charles tried to say as Kurt kissed his neck.

Like a puppet dancing on strings Charles had no control of his body! He was hard in an instant when Kurt's lips touched his neck!

"You smell so nice..." Kurt said inhaling.

'I'm still using my old shampoo and body wash?' Charles wondered before remembering that his sister used the same products.

His wonderings halted with Kurt's inhaler and exhales. Goosebumps exploded all over his body! Arms, legs, even his neck! Charles could feel his penis weeping pre-squirt, his body was telling him he was ready for sex.

Charles was worried he would blow his load right in his sister's panties! He had no control over his body! He knew he wasn't gay in the least.

'Heck!' He thought, 'I got just as hard for Lisa holding my hand!'

That was little consolation to him as he felt Kurt's hard cock press against him! More cum weeped forth from his cock, he had never experienced such a thing before!

"Aaaahhhh..." He tried to formulate words without success.

Wriggling free was of no use, it was as if Kurt had on gauntlets of strength. Charles assumed it had to be something magical and not his desire to see what would happen next.

Kurt's hands began to wander. One went to a breast and squeezed so hard that Charles felt it through his sister's bra. His nipple attempted to ignore it until it suddenly went as hard as his penis.

Kurt's other hand inched towards his crotch, Charles body instinctively pushed his ass back into Kurt, engulfing that massive cock between his cheeks much like the other day.

Charles yearned for what was to happen next, he didn't know how it would go down... that part of his mind was not in service. Unconsciously he had decided that he was just going to submit to Kurt right there in the kitchen.

Kurt's hand slid slowly past his belly button, touching the top of his skirt... Charles brain reactivated! If he had a cock the size of Kurt's he would have been found out by now!

"I'm...." Charles tried to say. "I'm..."

"Yes..." Kurt purred into his ear.

Charles took a breath to steady his thoughts. Back before he moved to the US he had done a Polar Dip for Charity. The way to do it was fast without thought.

"I'm on my period!" He said louder.

"It's still the first period and the Cats are doing good!" His father said from the living room, oblivious to them, or what they were doing.

Charles peeled himself out of Kurt's warm embrace, much like getting out of a sleeping bag on a cold day. It was reluctant but necessary.

"We are broken up!" Charles hissed fearful that he was almost found out.

"Whoa!" Kurt teased. "You ARE on your period!"

Charles almost said 'I am not!' because it wasn't biologically possible. He however bit his tongue, he had a job to do! He wanted to save his sister's semester of school, not bang her boyfriend!

"Don't you forget it!" He snapped pointing a finger at Kurt.

Kurt shrugged with his usual disarming smile, Charles hoped that he was becoming immune to it.

"What are you doing here and how did you get in?" Charles chirped, his wits returned.

"Your old man let me in." He said, "besides you said we could study."

Charles knew he didn't make a date. He planned on calling his friends, and playing some Red Alert or Master of Orion 2.

"If you can keep your hands to yourself..." Charles nagged, "then maybe... we can get an hour of study in."

Kurt nodded then sat at the table, Charles could see that he was still tenting in his trousers. He was too, but thank Jesus his skirt covered it!

"I need to..." Charles started to say, he knew he needed to clean the pre-squirt from his sister's panties, but didn't know how to say it. "Um... changed my pad."

"Sure..." Kurt teased.

Charles still had those aching goosebumps on his limbs. It was a biology lesson he didn't want.

"Aren't you getting your books ready?" Charles said halting mid-step.

"I thought I could get a bite to eat first." Kurt said smiling his pearl white teeth at Charles.

"Ugh!" Charles declared stamping a foot... just like Charlotte would. "Get it your damn self!"

"Quit with the noise!" Barked his father. "The Rough Riders just got a touch down! You're both bad luck!"

"Women's work is never done!" Charles stormed off huffing.

In the bathroom he wiped away a great deal of cum, so much so that he was glad for the pad! It soaked up most of it. Realizing that Kurt would see the garbage empty of pads and ask why; Charles muddled his way through several which he rolled and tossed in.

Returning to Kurt, he warmed some left-overs then sat with him.

"Don't they feed you are the dorm?" He asked.

"They do, but coach let us out too late." Kurt said.

Charles perked up at this, Coach had quite the reputation, but separating fact from fiction was a challenge. He had heard about the no underwear rule... which didn't make sense.

'Oh...' He thought remembering how Kurt didn't have any on when he jerked him off by accident.

"All done!" Kurt said standing up and walking to Charlotte's room, both cutting off further discussion and... leaving his dirty dishes behind!

The study session went much longer than Charles expected, however like the last one it was very productive.

Charles felt both very ready for the exam and very sore! He rubbed his aching shoulders.

'Why do they hurt so much?' He wondered massage his shoulder. 'I don't even have tits!'

Kurt stood up to yawn, then stretched. Charles saw him walking and assumed he was headed for a piss. He returned his eyes to his book, grateful that he had filled the garbage pail with rolled up pads.

"Uh... what?" Charles exclaimed when Kurt's powerful hands landed on his shoulders.

"Charlotte," He said softly as he dug his fingers into Charles shoulders. "You seem so stressed out."

"Oooohhhh..." Charles moaned. "You have no idea..."

Kurt kept going, it felt so good to Charles that he closed his eyes. That bra was killing him!!!

Kurt's hands moved lower.

"Oh!" Charles moaned, it felt even better!

This time Charles didn't get an erection, it was relaxing. He had friends that had paid for massages, they had said that it started with the happy ending. This however was satisfying.

Kurt worked his bra line causing Charles to close his eyes, he was in heaven! The tall muscular football player had such a gentle touch when he wanted too.

As if guided by an unseen force Charles found himself rolling over until he was face down on the bed. It didn't feel sneaky, or perverse, just a friendly massage.

Kurt at first stood over the bed, then he sat down beside Charles.

"Scooch over Charlotte I need more space to work." Kurt said encouraging him to move further onto the bed.

Charles tried to say 'no funny business' but a grunt of relaxation came out instead.

"You have so many knots in your back." Kurt said.

"Uh.." Charles tried to say. "This is so relaxing..."

"You want more?" Kurt asked.

"Yes..." Charles said dreamily.

Kurt straddled his torso about his waist. Charles had been in this position before with Kurt, but somehow this was different. There was no erection jabbing into him.

"Do you want me to work your body deeper?" Kurt said.

Charles was in nirvana! If Kurt stopped talking he would be asleep!

"Do whatever you want to me..." Charles moaned in reply.

Charles didn't feel it at the time, but like a frog in a pot, the water was getting hotter. Kurt worked his entire back now, not just his shoulders.

Time meant nothing to Charles as he let all his stress fade from his body. Kurt placed his hands on his hips then slid them up and under Charles shirt. His flight or flight instincts were disabled and he didn't flinch or move away.

Kurt worked Charles flesh deeply, he also inched up his shirt ever so slowly.

"Leave my... shirt on...." Charles tried to say.

"I need to pull it up to get better access to your upper back." Kurt said.

"Okay..." Charles said weakly.

Kurt lifted it up to his armpits then worked his mid-back. Charles enjoyed the attention.

"I need to undo your bra." Kurt said.

"No..." Charles feebly protested.

"I need to better access your bra line." Kurt said.

"Um...." Charles said as Kurt undid it.

Before Charles could protest Kurt worked his bra line with such talent!

'A girl could get used to this...' Charles thought to himself.

Charles didn't quite notice the change, he was still relaxed, but the massage had altered. Kurt worked him all over. The edges of his body and even his lower back.

When Kurt reached forward to work his upper shoulders, he could feel the jock's pelvis push into him. At first it was nothing, but soon he felt what could only be a sem-erect penis.

Charles didn't panic, he was a dude himself. Sometimes one just got a chub and it didn't mean anything.

Kurt started scratching his back, causing goose bumps to form then disappear as the muscular man's hands wandered elsewhere.

He felt his own penis stirring, and passed it off as massage chub, assuming that all men got them during normal massages.

What did bother him was that his penis was pointed downwards. As his manhood engorged with blood it became increasingly uncomfortable.

Kurt expanded his zone of massage both higher and lower.

"What are you doing?" Charles grumbled at his massage being interrupted.

"This shirt must come off!" Kurt replied dramatically. "You cannot expect me to work under such conditions!"

Charles wiggled in protest and found that Kurt's man-sausage was suddenly planted in the now familiar spot between his ass cheeks.

"Eeeep!" Squealed Charles as he felt that large log of cock against him.

Charles continued to wriggle, Kurt used that the opportunity to slide his shirt off one arm then the next! Charles eeped again as he clutched the shirt around his neck! The last thing he wanted was to be nude!

Kurt cut off Charles' protests by working his shoulders gently, there was no hint of malice in his fingertips. To be safe, Charles locked his arms under his body, holding his sister's bra in place.

'He must have really helped my blood flow.' Charles thought to himself as felt that stirring sensation in his loins.

He couldn't deny that he was getting a boner. It ached under his body. Every time he tried to adjust his hips, Kurt groaned in pleasure as his ass pushed into hard cock.

The irony of pushing into an erection because of an erection was not lost on Charles. The last thing he wanted to do was give Kurt a false signals.

"I'm on my period." Charles said remembering his go to excuse.

"I hear you." Kurt breathed into Charles ear shooting goosebumps anew. "I'll work your lower back."

Charles was going to ask why, when Kurt tugged his skirt down to expose the top of his ass cheeks. He was going to protest, or he thought he would, but all this attention was going to his head.

Kurt worked his hips and the top of his ass. Charles was uber grateful that he bore a pad in his panties. He figured Kurt would see it and remain a gentleman.

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