Cherreads

Chapter 28 - Gwendolyn is Naughty…

James stood there for a long moment. A long, long moment. Then he took a deep breath.

'Can't change the past, so let's look forward! Though… I'd rather not..'

"C'mon James, don't leave us hanging."

Clara looked at him with puppy dog eyes.

James a brief internal struggle about telling them or not, but then remembered that it didn't really matter.

'This world is so perverted that I would probably be applauded for having such a class.'

James didn't explain his class, rather he just told them to identify him and he accepted their request to view his class information.

"Brother that's a little…"

"Brother is such a pervert!"

"James dear.."

"Wow."

'What type of reaction is that!? Even my soncon mom is blown away!'

"I couldn't see the class information before I picked it, believe me! That's why… umm yeah… that's why it took me so long to pick! I took the risk that the myth- legendary class would be better than the others…"

They in fact did not seem to believe him.

'Why is nothing ever consistent with these people.'

"We can talk more about this in the morning. Girls it's time for bed. James dear, I don't have uh.. your room ready yet.. so you can sleep with mommy tonight!"

'That's the worst lie I've ever heard.'

His sisters also seemed to have something to say about this.

"That's not fair mom! You spent a whole week with him already. One of us should get him tonight!"

"Yeah mom, Clara's right. That's not very fair and I'm sure James wants to catch up with his sisters too."

"Yeah, what they said."

Clara seemed positively outraged and Madeline had a very sinister glare. James couldn't really tell what was going on in Gwendolyn's head.

His mother couldn't seem to refute their words and she just stomped out of the room without saying anything.

Then his three sisters turned to him.

"Sorry about mom.. we'll I guess you know how she is. Anyway brother, which sister would you like to pamper you tonight?"

Madeline said this with a tender smile and a crisp clap of her hands.

'This smells like trouble.. I'm going to piss off whoever I don't choose.'

"Well I couldn't possibly choose between my sisters… you girls should probably decide for yourselves.."

Madeline looked a little astonished at his ability to worm his way out of her trap.

Clara didn't seem to intend for him to get off that easy.

"No, you have to choose! You just returned.. we want to make you as happy as possible.."

James was actually surprised how warm his heart felt at that moment. Unlike with his mom who had a very intense fetish, his sisters seemed to care quite a bit about his personal feelings.

"… it's not that I don't want to choose.. it's just that I can't. I missed all my beautiful sisters very much and that literally makes this impossible for me"

'They can't possibly still make me choose after saying this… can they..'

This time his thoughts were correct and sisters formed a huddle. They seemed to be playing a version of rock paper scissors.

After a few rounds Clara and Madeline looked depressed as they cursed Gwendolyn under their breath.

Gwen herself on the other hand, didn't have even a trace of emotion as she grabbed James's arm and led him away as the victor.

Two flights of stairs and several hallways later, Gwendolyn pushed open a door to a very plain bedroom.

There was a bed, a chair, one bookshelf and a closeted wardrobe.

'Does she have a personality…'

Then, James noticed a few shelves lining the walls. He stepped to the closest one and saw it had various rocks on it.

Most just looked like pieces of gravel, but some were brilliant gemstones that reflected the moonlight.

Trying to get to know his sister better, James asked a very lame question.

"So do you like rocks..?"

For the first time since he had met her, Gwendolyn showed something other than indifference on her face.

A wide smile blossomed from her lips. leaving James a little dumbfounded.

"Yeah.. they're really cool."

"Oh.. okay."

'She and I both have such a way with words.'

He turned back to the collection to study the display.

"If I ever find a really good one, I'll make sure I give it to you."

A sudden flair of pain assaulted James mind as memories of him and Gwendolyn inserted themselves into him.

Little hands went to pick up a rock, then they gave the rock to a smiling girl who seemed to cherish it with all her might.

Dozens of different scenes slammed into him of this scenario.

This time the pain came and left instantly, nowhere near as bad as the first time the foreign memories assaulted him.

James absently rubbed a little rock between his fingers before turning and looking at Gwendolyn again.

'These emotions… I can't tell if it's my own feelings or the ones of the real James.'

Shaking his head he decided that it didn't matter and this girl was his sister now.

James stepped towards Gwen and gave her a hug.

"I've missed you.."

Gwendolyn returned the hug in a much more gentle way than her previous ones.

"I've missed you too brother.."

And then he felt his shoulder get wet as the tall girl cried onto him.

Suddenly she picked him up and carried him to the bed. She placed him down and climbed in next to him.

She resumed her embrace and soon the duo fell asleep.

—————

James hadn't dreamt of his trusty stick recently and was surprised to find it firmly butted up against his stomach.

"Hey little buddy, long time no see."

James tried to move the stick to get a better look at it but it stubbornly remained in place.

He tried again but the same thing happened. He gave one last tug and grew angry.

"Why must you always defy me! That's it, this time I'm teaching you a lesson you won't forget!"

—————

Gwendolyn didn't get embarrassed often. Actually she couldn't remember the feeling once in all her life.

But when she woke up to find her hardness firmly pressed into her brother, she could feel her face grow hot.

Her brother seemed to be sleep talking. She stopped trying to make out his words when two hands wrapped firmly around her shaft.

"Get ready, it's time for your punishment~~"

Her breath caught as she felt her brother start pumping his hands up and down.

She tried to weakly cry out.

"J-James.. you can't-"

Her voice cut off as they stroking more vigorous.

With a gasp, Gwendolyn pushed her sleeping brother away a little.

His hand grabbed at the air in a searching manner as Gwendolyn caught her breath.

Gwendolyn felt a deep shame rise in her as she slowly slid down her pants.

"This isn't on purpose, purely accidental.. if brother touches me, than that just means his hands wander too much at night."

Gwendolyn slowly got into position as she scooted closer to her brother on her back.

Her solid member was standing tall 8 inches into the air. She gently guided his hands to her and let him start again.

She was leaking precum like a faucet and the lubrication added even more pleasure as her brother stroked.

His fingers grew more dexterous with each passing moment.

"Sorry brother but I'm going to-"

An eruption of cum spurted out as Gwendolyn trembled from the pleasure.

After seven hard pulses raced through her cock, cum soaked her stomach in hot jets of white.

Gwendolyn felt her shame return and quickly started to disengage herself from the situation.

She froze when she looked over at her sleeping brother's face. He wasn't sleeping anymore.

————

James's body had a very enhanced perception that grew each time he leveled. So he woke up immediately from his disciplining of the stick after a foreign liquid covered his hands.

He looked around warily and took a moment to fully register what was going on. His eyes bulged as he took in the scene.

'I just jerked off my sister in my sleep. What an incredible sentence~'

James was figuring out how to apologize when Gwen locked eyes with him.

'Is she gonna be pissed or..'

"James forgive this lustful elder sister.. I took advantage of your restless sleep. Please don't hate me.."

While Gwendolyn didn't look like she was about to cry or anything, the intense blush she wore seemed to be the same thing.

James was surprised by the confession, he had been expecting a rebuke instead.

'I can use this to my advantage… in this tempting world I've only been able to satisfy myself once. That needs to change.'

"Gwen.. do you have indecent thoughts about your brother?"

She hung her head in shame as she replied.

"Yes.."

"Sister that makes you a naughty girl.. do you know what happens to naughty girls?"

"They get.. punished?"

*Aaah*

A surprised noise came from Gwendolyn as James leaped up to straddled his sister.

"Correct, they get punished. I, as your brother, will carry out this punishment now."

James pushed down his pants to reveal his half erect cock.

"Sister, open your mouth."

She did as he asked and opened it without question.

James then placed his length into mouth.

"Suck."

Instantly her wide open mouth wrapped around his cock and sucked hard.

James fell forward a bit as her powerful suction pulled him in. He could feel himself growing in her mouth to full mast.

There wasn't any sound from her mouth as James slid into throat. He could feel her tongue working nonstop and her throat kept swallowing repeatedly leading him to a sensation he had never felt before.

"Ahh, you feel so fucking good."

James leaned over his sister and placed his arms out in front of him. In position, he started thrusting downwards as he fucked her face.

He began with long, powerful strokes leaving only the tip in her mouth before plunging down to the base.

"Take that dick you naughty little slut."

James kept pumping until he couldn't take the intense pleasure anymore and settled for hovering a couple inches above her face as she bobbed on him with her throat.

*Haah *Haah*

He could feel his climax soon and felt Gwen's arms wrap around his waist, pulling every last little bit of cock she could into her mouth.

*Gaaah!*

James came hard in her throat.

He slowly removed his length from her mouth, spasming as her powerful suction continued until he fully exited.

Gwen only seemed a little out of breath as she leaned her head up to kiss his cock.

She then turned to look at James.

"I'm sorry for being such a bad sister.."

"Gwen, when did I say you were a bad sister? You're just naughty, I like my naughty sister very much."

James said this with grin.

Gwendolyn's face had almost fully returned to her placcid demeanor from before. But the smallest hint of shyness peaked through.

"Really.."

"Yes really, I can't wait to do so very many naughty things with this beautiful sister of mine."

Gwendolyn suddenly sat up and caught James from falling backwards.

They stared into each other's eyes before plunging forward to share a deep kiss.

They kissed for along time and broke apart only to get more comfortable.

They layed on their sides facing one another and resumed their kiss. When they stopped and finally decided to fall asleep, James could see a very big smile on Gwendolyn's face.

'My family seems to be a little different from what I saw back on earth..'

More Chapters