Charles in Charge Ch. 08

1996

Autumn

Nebraska

Please note, all characters are 18 years or older.

Charles stood there as the three men approached, trying to act brave.

His finger and toe nails were painted a bright red and his ass felt empty from an absent buttplug.

'A most curious combination...' Charles wondered to himself.

The nails were due to him dressing as his twin sister so he could write her exams, while she was away getting life-saving surgery.

"Charles!" Barked out Tad, the bully Charles had beaten up earlier. "I need to talk to you..."

Charles gulped, but stood his ground.

"About your sister!" Tad said loudly.

Charles tried not to flinch at the words. He was dead certain Tad wanted to settle the score.

"What do you want with... her?" Charles tried to say bravely, however his voice cracked.

The three men stopped in front of Charles, in the low light he couldn't see the two goons flanking his bully. Tad however was sporting a dark and very fresh black eye.

Charles grinned in pride! If he was going to die at least he got Tad pretty good in advance.

"I need to talk to her." Tad said in gruff voice.

"Whatever you want to say to her you can say to me!" Charles proclaimed.

Tad looked at his goons, they stood ready at his side. After a wordless consultation he spoke up.

"Look," Tad said. "I don't want problems."

Charles gulped! He expected to be getting an atomic wedgie by now.

"You ddddon't?" Charles stuttered.

"No." Tad said. "I owe her an apology."

Charles was baffled! More greater than that he wondered what would happen if he changed back into his sister's clothes?

'Gangbang with jocks?' Charles wondered. 'Could my ass and mouth handle it? More importantly could Charlotte's reputation?'

"Focus!" Barked Tad.

"Uh... yeah." Charles said.

Tad looked at his gang again, Charles now sported a fully grown erection.

"Can you go get her now?" Tad asked, then added, "please."

"Oh... sure, I'll go get her." Charles said, he decided he'll change and see what happened next.

"I'll help." Said one of the goons.

Sweating Charles stepped back. All his visions of gangbangs were quickly replaced by those of a beating. He didn't know how he could change clothes with someone with standing over him.

"That's ok..." Charles said stepping back and thinking about making an exit, he was certain he could outrun three football players...

"Don't be like that." Said the goon stepping out from the shadows.

"Kurt?" Asked a confused Charles.

"That's me!" Exclaimed the tall blonde man.

Charles opened his mouth to protest but stopped when he saw the giant man's smile, he could never could say no to it.

"Don't worry 'bout us." Declared the other goon, which sounded a great deal like Tyreese.

Charles jaw hung open! Moments before Charles was convinced he was in for some sort of pounding. Be it fists or dicks, now he was flanked by allies!

"Ha-zah!" He cried out with a fist pumping in the air.

Tad rolled his eyes.

"So gay..." Tyreese said with a wink to Charles.

Kurt shot the other two jocks a glance that shut them up. Tad seemed to frown as Charles grinned ear to ear! A blowbang with these men sounded like a great idea.

'Now how to make it happen?" Charles wondered to himself.

"Ya'll have a gay-old-time searching for her..." Said Tyreese. "Tad and I are gunna chill out here."

"Whatever." Said Tad in a huff.

Charles didn't think he'd be able to get the three men together in a quiet spot if they separated like this. He didn't even know how he'd give Kurt the slip so he could change!

'Why am I so cock hungry?' Charles wondered as they approached the house. 'I literally just got laid by a chick!'

"Charles!" Barked out Kurt snapping back to reality. "You go upstairs, I'll look down here."

"Sure..." Charles replied gleefully!

Re-entered the bedroom Charles could see Connor balls deep missionary style with the girl he was with before. It reminded him of his encounter with Lisa earlier that night.

'Who is that girl?' Charles wondered as he moved in the shadows until he saw her face.

'Holy crap!' Charles said to himself as he fought to control his breathing 'Felicia!'

It wasn't that she was having sex with two dudes that shocked him. What surprised him was that Conner most likely ate her creampie! He had seen her getting laid earlier that night!

Once in the bathroom Charles locked the door and stripped out of his men's clothes. His creampie eating revulsion evaporated as fast as his clothes came off.

Washing his face with soap and water, Charles no longer feared cum or its taste. Women's clothes just seemed to have that affect upon him.

Charles did his make-up as fast as he dressed; thankfully he had few garments to put on... bra, shirt, panties and skirt.

He painted his eyelids as he wondered if Kurt would keep Looking for him, or give up the chase to catch his flight. Butterflies fluttered in his stomach at the mere thought of it all.

Looking into his tiny purse Charles found fresh eye lashes to put on. He blinked several times at his new reflection as he tried to remember what was next.

"Hair extensions!" He exclaimed.

Digging them out he had them in place quickly.

'Am I ready for this?' Charles pondered as he looked at the giant butt-plug, he knew he couldn't leave it there.

He greased it up, then set it on the toilette lid. He then pulled his panties aside as he turned around.

"Uhn!" He grunted as he sat down firmly onto it.

When Charles felt the coldness of the lid on his ass cheeks did he believe it! He had taken the massive beast in one go!

'Could I do the same with Kurt?' Charles wondered as he pulled on his stockings.

His plan was to give Kurt a blow job or two; then send him home as happy as a sailor after shore leave. Despite having the beast up his ass, anal was rarely on his mind.

Opening the door cautiously Charles saw that he was alone. Connor must have eaten all the warm jizz he wanted before leaving the party.

Entering the hallway Charles spotted Kurt and gave him a wave. Amid the crowd of people the giant blonde athlete saw him and pushed his way through the crowd. Charles felt as if he were the football Kurt was attempting to recover!

"Hey..." Kurt said dumbly.

"Uh... hi?" Charles said before he remembered that he was now Charlotte and not Charles. "Um... nice party eh?"

"Uh... yeah it is." Kurt replied nervously. "I was... looking for you."

Charles was hard from taking in the beast, now it was aching! Kurt was so cute fawning over him! Charles had stumbled over his words with girls, but to have someone do it in return.. well to him it felt incredible.

"Tad has something to say to you Charlotte," Kurt said, "he's waiting outside."

"He's just lucky I don't tackle him again!" Charles stated proudly.

The two shared a laugh at that. Charles knew he had the element of surprise with the drunken Tad, it was something he would never again achieve.

"I heard!" Kurt said moving closer.

Charles stepped closer to Kurt to whisper into his ear.

"Forget him..." Said Charles softly, "come with me."

Like a re-animated corpse Kurt followed Charles into a room, it was as if he were totally under a spell!

Once in the room Kurt opened his mouth to speak, but words did not come out. Charles lunged at the muscular man kissing him deeply.

It only took a split second for Kurt to clue in, when he did he embraced Charles and kissed in return. His giant paws he had for hands roamed Charles' body as if it were their first time.

Kurt squeeze his hips, then pinched a nipple roughly. Charles now used to it moaned like a woman, inwardly he could have done without it. When Kurt cupped an ass cheek they both went silent.

They stared into each others eyes wordlessly. Kurt in his groping had found the butt-plug and had pushed it in slightly by accident. Charles was scared and nervous! His cock felt like it was going to explode!

"Looks like you found my gift?" Kurt teased breaking the silence.

"I did!" Charles replied excitedly. "And the others."

"I wasn't sure if that was your thing or not..." Kurt said.

"Honestly..." Charles said between soft kisses. "it wasn't until this week."

Kurt French kissed Charles in excitement, then swept the smaller man in drag into his arms. Charles shrieked in delight as Kurt carried him to the bed on his back.

Charles gulped as Kurt got between his legs missionary style. Looking around he gulped again as he realized he was in the same bed he nailed Lisa in only 30 minutes before!

Charles panicked as he could feel Kurt's cock pressing against his own! He assumed the jock didn't notice so he shifted his body so Kurt's dick pushed against the beast of a butt-plug jammed in his ass.

The sensation was incredible! Goosebumps formed all over his body! Charles could hardly breath, it was all so surreal!

Kurt eased back; curious Charles opened his eyes to Kurt opening his drawers!

'Oh fuck!' Charles thought to himself. 'What will Kurt do when he realizes that I have a nutsack and not a vagina!'

"I'm on my... period..." Charles stammered out.

Kurt pulled out his giant ivory elephants trunk of a penis, even soft it was larger than Charles own. The quarterback didn't reply immediately, he instead stroked his meat to life. Charles began to panic! There was no avenue of escape for him!

"I was going to put it there..." Kurt purred.

Charles gulped in fear until he felt Kurt pushing on the plug again. Then he was really scared!

'Anal?' Charles wondered to himself.

Kurt didn't give him time to think it over. The large man moved back then flipped Charles over so swiftly it pushed the air from his lungs.

Once on his stomach Charles had decided that he didn't want to get eight inches of white dick jammed into his anus. He started to crawl forward before a strong hand on his tail bone pinned him to the bed.

Kurt carefully pulled Charles panties aside. Charles could feel the cool air on his asshole followed by the moist breath on his ass cheek.

'What will he do when he sees my nutsack..' Mused Charles as his heart thundered in his chest in anticipation!

Kurt however either didn't see or didn't care as he stuck his tongue out. Charles quivered as Kurt licked around his impaled butt-plug.

Once the jock had it sufficiently lubricated the plug he gave it a slight plug.

"Ohhhhh...." Charles purred as the giant ass plug was pulled out.

"Oh!" Charles grunted when Kurt pushed it back in.

Charles dick was incredibly hard, although he had just had sex multiple times with Lisa previously that night, he had rebounded.

After teasing for some time Kurt finally pulled the plug all the way out. Charles' exposed anus felt, cold, alone and so very vulnerable.

"I can smell your pussy juices." Kurt said pulling Charles' ass cheeks apart.

Charles felt more vulnerable than ever before! He had no idea what Kurt was sniffing until he remembered how many times he made Lisa explode all over his cock and balls.

"Your pussy tastes different, but yet so familiar..." Kurt said with his face buried in another man's ass.

Gulping Charles spoke slowly, "My period is still going, but my... ass is all yours..."

Kurt grunted, which Charles hoped meant he heard and understood. When Kurt sank his tongue deep into his ass Charles was certain the message was received.

"Oh yes!" Charles called out unabashedly as Kurt ate his ass out.

He wanted to jerk off so badly as the football player worked his ass over! Kurt would lick then with his massive hands part his cheeck then spit right into his hole.

"Oh GOD!!!!" Charles moaned once he felt a finger buried deep into his anus.

Kurt soon shifted to two fingers; Charles couldn't believe his ass could take so much stretching.

Charles moaned his whorish delight as Kurt shift shifted his body. He didn't think anything of it until he felt the large white cockhead lining up with his anus.

"Take a deep breath..." Kurt advised as he spat into his hands to grease his pole.

"Uh.... Oh god!" Cried out Charles as Kurt pushed in the head.

Charles was pushed forward by his sister's boyfriend's cock. It just didn't fit.

"I don't think we have enough lubrication." Charles suggested between strained breaths.

"Oh yeah!" Exclaimed Kurt as he flipped over Charles.

Charles found himself on his back, with his head dangling off the side of the bed. He opened his mouth to suggest they use the lubricant in Charlotte's purse, however Kurt had other ideas. He had jammed his penis down Charles throat.

The giant athlete worked his cock in and out of Charles mouth. The petite man in drag under him moaned in pleasure and anticipation.

Charles could feel Kurt's testicles slapping against eyelids it was most unusual sensation. He tried to open his jaw as far possible to take it all in.

Time seemed to lose all meaning as Charles was sucked further into the facefuck vortex. Pleasing his sisters boyfriend was now his only goal.

With a wet sloshing sound Kurt withdrew his man-pipe from the other man's face. In a quick fluid movement he flipped Charles over onto his stomach.

Panting Charles got to his hands and knees, he had forgotten about the sex. He set himself up like that to draw in deeper breaths.

"Uhn!" Grunted Kurt as he pushed forward with his thick meat stick.

"Oh!!!!" Cried Charles as he was finally impaled!

Both men froze in place panting after finally achieving one-ness. Charles' asshole was burning fire!

'Am I gay now?' Charles Mused to himself as he could feel the engorged veins throbbing from another man's penis.

Charles didn't feel gay, he felt like he was just having a good time with someone he enjoyed being with.

"Oh yeah!" Kurt moaned snapping Charles back to reality.

Kurt pushed his dick deeper, Charles sucked in a deep breath. The various butt-plugs he used were fun, but the real thing was incredible!

As he accepted more and more of the other man he could feel a growing fullness followed by a most unique pressure deep inside himself.

With a final shovel Kurt was buried to the hilt inside the other man. Charles felt their testicles touch, then he groaned deeply.

"Oooooohhhhhh!!!!!" Charles grunted loaded as he came.

"Yeah..." Kurt said between deep breaths, "I like anal too!"

Charles felt embarrassed! He enjoyed cumming, but cumming without any contact with his penis was unusual.

Kurt however didn't let the smaller man ponder his orgasm for very long. He pulled back his hips, then rammed them forward.

"Oh!" Cried out Charles uncontrollably.

Kurt picked up his pace, as Charles increased in volume. The two men conjoined as one, now worked together to bring about mutual pleasure.

"Oh God!" Charles cried out as he pushed his ass to meet Kurt's thrusts.

"OH GOD!!!" Charles said in panic when Kurt lifted his skirt.

Charles was worried he would be murdered when Kurt saw his testicles bulging under those panties!

SMACK!!!

'That feels good!' The smaller man thought to himself, no longer concerned with his secret.

SMACK!!!

Charles made a mental note to remember to spank ass next time he fucked a lady. He was already hard again from this blunt force attention, he could only imagine how it would feel like for a lady!

"Get ready!" Kurt yelled in his deep football voice.

Confused Charles looked over his shoulder half expecting a pigskinned ball to hit him in the face. What got him in the face startled him just as much!

Kurt pulled out of his ass and moved his giant muscular body over towards the smaller man. Grasping his dick with one hand and a fistful of Charles' hair with the other it began.

Cum fired into Charles face! It felt hot as it splashed on to his nose, forehead and eyelids. Charles opened his mouth to take in a deep breath and sucked in warm semen.

It tasted salty. Charles felt like a pornstar!

Dragging the smaller man by his hair, Kurt wasted no time in letting Charles savour the moment. The jock sat on the side of the bed, then lined up his thick white cock with Charles anus.

Charles didn't waver or hesitate as he impaled himself then rode like cowboy in the other man's lap.

"Oh yes!!!" Cried out Charles as he bobbed up and down, warm cum on his face.

Charles cupped his balls as he prayed that Kurt couldn't feel his nutsack landing repeatedly on the other man's.

'I really am a dirty slut!' He thought to himself.

"You sure are!" Kurt said to an embarrassed Charles who thought he had spoken to himself.

Charles wanted to make this memorable! He reached into his panties and started stroking his much smaller dick as he rode a much larger one.

His other hand rotated between Kurt's thigh and his shoulder, Charles couldn't quite find a stable anchor.

If someone were to walk in they would see the two men engaged in the gayest of sex. Charles didn't care at this point.

He raised then lowered his ass on the other man. When he switched his anchor hand he ground he butt down into Kurt's lap.

Moans of pleasure filled the room!

Charles could feel his orgasm growing, so he eased off on himself until Kurt was ready.

The giant footballer below him reached up unexpectedly to pinch Charles nipple! It hurt way so much that Charles was dead certain he didn't want to be a lady again after that night!

The pinching however had its desired effect! Kurt's already girthy cock grew even wider! Charles asshole already stretched was being asked to stretch even further.

Charles jerked himself off fast and hard! He knew it was time!

"I'm ready!" Kurt grunted between breaths.

"Me too!" Declared an eager Charles.

The two men then simultaneously came! Kurt fired his seed into Charles bowels, whilst the smaller man in drag fired his into his leg.

The two men stopped suddenly, deep panting now replacing orgasmic grunts.

"Whoa!" Cried out Kurt breaking the silence.

Charles started laughing, it all seemed so funny to him. The sweat, the cum inside and on himself, the very large and still very hard dick up his ass.

"I wish I had time to do this again!" Declared the giant jock.

Charles snapped back to reality!

'Oh shit!' He thought to himself as he tucked his flacid penis away.

The small man pushed up on Kurt's knees as he tried to un-impale himself to no success. He was too exhausted and Kurt's cock too big.

"Let me help..." The quarterback said standing up with Charles in his arms.

"Oh fuck!" Charles shouted as he was suspended in the air.

Kurt lifted Charles up and off his penis. Charles grunted as he felt his sisyers boyfriend's cock slowly withdraw from his body.

'How long is it!' He thought to himself as the endless snake slid out his asshole.

Kurt set Charles on his feet, the two faced each other awkwardly. Charles wanted to hug and kiss the bigger more muscular man, but felt that kurt didn't want such affections.

"I'm going to brush my teeth..." Charles said thumbing towards the bathroom.

Kurt's smile was giant! Charles mentally shook his head at the jock's reluctance to kiss his cum covered face.

Charles anus felt so empty and sore! He had to pee, but didn't have the energy to stand up, so decided to sit.

"Fuck that was awesome!" Yelled a naked Kurt as he stepped in the bathroom, his giant penis swinging about.

"Ahhhh!!!!" Shrieked Charles and he covered his tiny ivory penis.

"Chill out babe..." Declared a laughing Kurt, "it ain't nuttin I haven't seen before."

"I need to change my pads!" Declared a quick thinking Charles as he tried his best to stay mad.

"How did I get jizz on my leg?" Kurt declared ignoring Charles.

The smaller man quickly slapped in a fresh pad as he wondered if it were his own cum? He then washed his face, brushed his teeth, reapplied make-up, all whilst the blonde giant next to him gave a play by play of their fuck session.