Date: Mon, 30 Jul 2007 07:19:28 +0000
From: Jack Boy <jackieboy1992@hotmail.co.uk>
Subject: Jacks Cool Family chapter 2

This story is a combined effort between Andy and Jack.  As such, both of
our emails are available for comments.  Please email any comments to either
andys_stories@hotmail.co.uk or jackieboy1992@hotmail.co.uk.


Disclaimer.

1. This story will involve sex between an underage boy and various members
of his family, both female and male.  If you don't like this sort of story
please leave now.

2. If you are too young to read the above type of material, it's up to you
to leave.  We certainly wouldn't encourage you to do this stuff.

3. Not allowed to read this type of stuff, I suggest you move before
continuing to read it!

4. This is total fiction that has sprung from our twisted little minds.

5. This story has been created by Jack & Andy and so is copyrighted to us.
Feel free to quote it, but please give us credit.  If you make any money
from this, let us know how so we can as well.  Thanks.



Chapter Two.

Mom handed me my clothes and told me to put them on and go and do my
homework before tea.  I stumbled upstairs in a daze, and grabbed my school
books out.  I finished off my homework in a super fast time, wandering back
downstairs in just my boxers to find my sister sat at the dinner table with
my Mom.

"Nice bod bro!" Jill said.  "Shame that Mom says you bat for the
opposition!"

My look of horror must have been apparent as I stared back and forth
between them, and I turned to flee back to my room, before my sister
grabbed me.

"Cool it bro," Jill said, struggling to hold me as I tried to flee.

Despite the fact she was a girl, she was very strong, and I had a slight
body, not being a jock.  I gave up trying to get away, and she let me slump
into a chair at the table.  Jill pecked my cheek before returning to her
seat.

"Why did you tell her Mom?" I complained.

Mom looked at me.  "I thought she should know because she can help you."

"How?" I asked.  "She's a girl, not a guy!"

"Excuse me," Jill firmly said.  "She has a name and is sitting here ya
know!"

I looked at her, embarrassed, and seeing her gazing intently at me, looked
away and back down at my feet.

"Jack, I have a couple of friends who are gay, so I know partly what you
may be going through." Jill said.

"Who are they?" I asked, wanting to know, as it may help fuel any jack off
fantasies that I have.

"I'm not telling you yet, but I know what they went through when they came
out to their families," she replied.

I looked up at her.

"So you cool with having a fag for a brother?" I asked.

She rose suddenly, leaned across the table and slapped me hard across the
cheek.

"FUCK!" I yelled, pulling back, feeling the sting immediately.

My Mom started towards my sister, who put a hand up to stop her.

"Don't you EVER use THAT word to describe yourself," Jill hissed at me.

Tears had started to escape from my eyes, as the shock of the slap wore off
and the pain settled in.  Jill came round the table and hugged me tightly.

"I love you little bro, and you being admitting your sexuality only makes
me feel more for you.  That's a horrid word though.  It's an insult and you
should never use it.  Yeah you may be gay or a homosexual, but you are not
queer and you are not that word either!"

I cried a little as I hugged her, and felt love as my Mom embraced both of
us, and we must have been a wonderful picture postcard of family bliss for
a moment.

Mom let us go while she finished up with dinner.  We both grabbed a coke
from the fridge and Jill led me to her bedroom.

Jill's room was a typical teen girl room, so I've been told.  She had
posters on the wall of the usual hunks, some of which I fantasised about
myself.  Leonardo DiCapprio before and after Titanic, the newest posters of
a very hot, and now no longer a kid, Billy Gilman, as well as some photos
of Wes, her boyfriend, who I'll admit was a hunk himself.

She patted the bed for me to sit down, which I did.  I suddenly realised, I
was still only in my boxers, and looking at the hot guys had made little
Jack start to wake up.  I went to grab a pillow to cover up, but she
brushed it away.

"Jack, getting hard is the most natural thing a guy like you can do when
surrounded by images he likes."

My love for Jill was growing with each passing conversation.

She took her shirt off, leaving just a bra on, covering her tits.  She shed
her skirt as well, bending over giving me a show of her butt, on purpose I
was sure, as she found some leisure bottoms to put on.  She sat next to me.

"So you're gay, and want to be fucked by guys?" she opened up with.

I had been in the process of taking a sip from the can, and ended up
spraying Jill, her bed and floor.

"Start with the easy questions sis!" I laughed, feeling more at home
talking to Jill than my Mom about it.

Jill wiped the spray of coke from her chest, laughed, before turning
serious.

"You know there are a lot of guys out there who would take advantage of you
and hurt you don't you?" she said, concerned.

"I guess so," I replied.  I had read lots of stories on nifty and the like,
and not just the pretty pretty ones where a kid found true love with a
multi millionaire.  Some of the authoritarian stories, whilst being hot in
their sex description, were quite scary for a lad of 13.

"So, Mom wants me to give you the un-censored birds and bees talk!" Jill
sniggered.

I flushed a little, before she continued.

"I know you know about jerking off." She started.

"How do you know I know?" I asked.

"You're hardly quiet when you cum Jack!" Jill pointed out the joining wall
between our bedrooms.

Of course, I flushed red again, but little Jack grew a little more.

"Blow jobs? 69s? Anal probing? Rimming? Full sex?" Jill started reeling off
a list of the various activities.  "Tell me when you haven't thought of one
yet, or don't know one."

"Whoa whoa," I giggled.  "I've guessed at how to do blow jobs, and, um,
I've sort of, um, practiced maybe, um, on a cucumber."

My chin hit my chest again as I tried not to look at her, but she lifted my
head.

"That's exactly how I practiced!" Jill said.  I felt a hell of a lot better
for hearing that.  Maybe I wasn't such a depraved pervert after all.

"I guess I know what 69ing is, but never had the chance to blow anyone let
alone get a 69."

"It'll come in time, let's face it, you may have a couple of years left in
you before you can't get it up any more!" she said, making me smile.

"What's rimming though?" I asked.

"It's where your partner makes love to your asshole with their tongue,"
Jill informed me.

"Eugh!" I said.  "I know that ass fucking obviously means sticking your
cock up someone's ass, but licking it out, that's gotta be gross!"

Jill hugged me and chuckled.

"I love the fact that you would be cool with someone shoving a ten inch
cock up you, but not their tongue!"

"TEN INCH COCK!" I almost yelled out.  "No fucking way has someone got one
that big."  I looked down at my four inches, now proudly poking through my
boxer fly.

Jill followed my gaze, and gasped slightly, and I saw one of her hands rub
over her own crotch.

"Can I look and see Jackie?" she asked, almost begged, huskily.

I always had had no secrets from Jill, other than THE big one, which she
now knew, so I shrugged to myself, stood up and peeled off my boxers,
leaving myself naked in front of my sister.

Jill licked her lips, and reached out and grasped my hardness.  I felt a
warm glow as she held my cock and she pushed me back onto her bed.

"Let me do this Jack," she said, as she started to jerk me.

I laid back, knowing that I may have trouble keeping my end up, but Jill
wanted this, and she was such a cool sister that I'd do anything for her.

She teased my foreskin over my head and set herself into a steady rhythm,
which she interrupted herself occasionally to give my cock head a lick with
her tongue.  Her free hand started off fondling my balls, before probing
lower and finding my pucker.  As soon as she touched it, I felt a throb
flow through my body, and I knew I wanted her fingers inside me.

"Please Jill, push them in!" I begged.

She needed no further invitation and thrust two fingers into me dry,
stopping only when her hand wouldn't go in any further.  I stiffened in
pain, squealing out loud at the shock, before succumbing to the pleasure as
she hit my spot.

Jill's hand suddenly left my cock, but was immediately replaced by her
mouth, her warm mouth.  This was all too much for me, and I bucked and felt
my balls draw up before unleashing a torrent of spunk into her waiting
mouth.

Jill lapped up my cum, stopping only when my cock got too sensitive for her
to continue, and her mouth made its way up my body, kissing my belling
button, her tongue tracing a route around my chest, pausing to suck on each
nipple, before nuzzling my neck and kissing me full on the lips.

I opened my mouth and we exchanged tongues and spit, and I tasted my own
cum on her tongue.

"You liked that huh?" Jill asked.

I nodded, unable to speak for a moment.

"What will Wes say though?" I asked.

"For a start off, I was just helping you out bro," she said.  "Wes's my boy
and will be for the foreseeable!  He doesn't need to know about this
okay?!?"

I nodded, as she had a hand wrapped around my balls and I thought it best
to agree with whatever she said.

"Plus, I've got another treat for you."

Jill got off the bed and wandered to her closet, rummaged around before
pulling out what looked like a fake dick.

"What's that?" I stupidly asked.

"It's a plug," Jill said.  "You can get what's called butt plugs, which a
lot of gay guys used to keep themselves loose, or prepare themselves with
as it helps stretch them."

"I've read about them in stories.  They make them sound really horny!"

Jill continued though, "recently though, a firm has started selling fanny
plugs.  It's like a butt plug, but thicker and longer.  This is mine, but
as I now get as much sex as I want from Wes's cock and I want you to have
it."

She handed the stiff rubber moulded cock and balls set to me.  I slid my
hand around it and up and down its length.

"This is huge!" I said.

"It's an 8 incher in length and three inches in thickness, more than the
average man, but if you get used to it, then most cocks won't hurt you!"

Jill leaned over to her bedside drawer and pulled out a white tube, and
popped the lid.

"This is KY Jelly, which is one of many lubes you can get.  You'll need
this when you fuck or get fucked okay bro, without it you'll get hurt."

Jill squeezed the tube and got a generous amount on my hand.  She told me
to coat the plug with it.  As I was doing this, I felt something cold
against my hole. I looked down and saw Jill spreading my cheeks and
slipping a lubed finger inside me.

"If you are gonna put anything up you, a real cock or a fake one, you've
gotta lube up first or you could tear something," my sister told me.

Finally she took the plug out of my hands and teased my hole with the head
of the dildo.  I felt myself grow as I felt pleasure spread through my
butt.  Suddenly she popped the head inside me, and I gasped in pain.

"Remember bro, this is thicker than most me, so if you get used to it,
you'll be fine later in life!" she cooed at me.

I gritted my teeth and told her to continue.

Jill pushed slowly with the plug, and it slid into me, a half inch at a
time until I felt so full I could burst.  My cock was straining for release
again as my prostate was tormented with the rubber cock sliding past it.
Suddenly the pushing stopped, and I looked up at Jill.

"That's it bro, you have all eight inches in you, well done!" She leaned in
and pecked me on the cheek.  "Even Wes couldn't take it all up him at the
first attempt!"

That definitely got my attention, Wes had had this shoved up his ass?  More
than once?

Jill pulled me off my bed and led me back to my room, naked, little Jack
pointing the way.  She threw my boxers into the pile of dirty clothes that
littered one corner of my room, and I should really have complained when
she opened my underwear drawer.  My mind was still in ecstasy with the
feelings that the plug gave me every time I moved though.

"Ahah! I knew you'd still have them," Jill exclaimed in triumph.  With an
evil glint in her eyes, she handed me my old pair of spider man briefs that
I'd never got round to chucking away.  I'd had them a couple of years, and
with my recent growth spurt down there, they would normally be tight.
However, with a major hard on caused by the eight inch dildo up my ass, no
chance!

Jill held the legs open for me to step into, which I did.  She pulled them
up, cramming my hardness into them.  I then was handed one of my body tight
t-shirts and a pair of shorts, again from a couple of years ago that I
hadn't got round to throwing out.

I sat down on my bed to put on a pair of socks, causing me to moan in
pleasure as the plug was shoved further into me, Jill ran back to her room
to quickly change.

She reappeared at my door and hauled me off my bed, and led me down the
stairs back to the lounge.  She pushed me through the door first,
propelling me awkwardly towards my normal spot on the sofa.  I was shocked
to see we had company.

Mr Harris, one of my teachers from school, was sat on the sofa, right next
to where I normally sat.

"Ah Jack, I've invited Mr Harris round for tea as he wanted to talk to us
about the swim team." Mom said.

"Um hi Mr Harris," I said, shaking his offered hand.

"Good to see you Jack," he said.  "I'm pleased that your Mom asked me round
as we need to talk over a few things."

I walked uncomfortably towards one of the chairs, before my Mom told me not
to be rude and sit next to my teacher.

Man, the problem was, Mr Harris was a hottie, very firm body and tall and
strong.  I'd had his hands on my body a few times during the course of
swimming coaching, nothing improper of course, unfortunately, but I was
about to sit next to one of my jerk off fantasies, with an eight inch dildo
up my ass.

I groaned to myself, gritted my teeth and sat down.  I moaned silently, so
I thought, as the plug grazed my prostate again, and for the first time
since it had been up my ass, I felt my cock give a little spurt of juice.

Mr Harris looked at me, as I'd sat down, and I swear I saw his eyes notice
my straining hard on that I was desperately trying to cover.

We made small talk for a few minutes, Jill taking great delight in
suggesting that I get up and fix Mr Harris a drink, before sitting back
down, before again suggesting he'd like ice, and then lemon.

I was going crazy inside, and my cock was leaking like a bust water pipe.
Finally my Mom suggesting going to the table to eat.

I grabbed Jill as we walked to the table.

"You knew he was coming here didn't you!" I hissed at her.

"Of course, I thought you may need some help admitting things to yourself
though!"

How did she know?  Was I that easy to read?



End of chapter 2.



Well that seems a good place to stop.  We'll deal with the dinner and the
rest of the night in chapter three.  Poor old Jack though, will he last
dinner without creaming his pants in front of his teacher?


Thanks to everyone who has written with their support after chapter one.
We will definitely keep the story going for a while until we run out of
ideas!