Date: Sat, 27 Nov 2010 13:47:33 -0800 (PST)
From: Billy Berglund <billykoolia@yahoo.com>
Subject: Halloween Helper Part 7

   If you shouldnt be here, be gone!  Enough said about all rules you know
em.  Obey em.

  This story belongs to the author and may not be reprinted without
permission.  It is writen solely for the readers enjoyment.

   This story is a continuation of the Halloween Helper series.

If you havent read it yet it might be good reading for the background on
these two characters.  Okay, get your cocks out and lets get on with it !!

  This story is dedicated to all the fans for your support and suggestions.
Thanks so much.  I hope you enjoy this seasons installments.

   The last night of the Haunted House was finally here.  Everything went
smoothly though I could not wait until it was over and I had all the boys
to myself for their sleepover.  All but Erik the freckled Irish lad was
able to get permission to do the sleepover.  I assured Erik that I'd see to
it that we got some time to spend together just the two of us so that he
wouldn't feel laft out.  He smiled and seemed happy that I would do that
for him.  There was no way I would let that chance go.  With his typically
milky-white skin and freckles I knew if I could get his clothes off that he
wouldn't stand a chance against my advances.

  At the end of the evening after everything was shut down me and the boys
took some supplies from the concession stand and went into the house.  We
feasted on hotdogs, pop, chips and candy.  The boys wree in good spirits
and hyped up over the night ahead.  After eating and just running through
the empty house for an hour I gathered the boys together for a game.

  "Alright boys we're going to have a contest called the hotdog walk !  You
will want to strip down to your undies.  We don't want to get your clothes
all messy.  Your mom's would scream at me."  The boys all chuckled at this.

  "Besides even though we are not going to bed for awhile yet it would be
good that your in your undies so you're ready.  The contest works like
this.  You hold a hotdog between your legs and walk to the other side of
the room.  If you drop the hotdog you're out.  First boy to reach the other
side is the winner and gets a 6 pack of pop to take home."

  I watched as the boys undressed.  All looked so cute in their undies.  It
was funny watching as they put the hotdog between their legs and attempted
to walk.  Only 3 made it all the way.  Jayjay, the brown-haired brown-eyed
gangly boy was first.  I went over and held up his arm in victory.

  "Okay boys you all did good.  But I'm sure you would all like a rematch.
Who wants a giant bag of candy?  That will be the prize this time !  The
rules change and it will be a lot harder.  This time you will have to take
your underwear off and put the hotdog in your butt crack and hold it there.
Now before you get all nervous about being naked noone is going to see you
naked.  I will take each of you just outside the door so you have your
privacy.  I will help you get the hotdog in place and then put a blanket
around you.  We will all still be able to see if you drop it so there's no
way to cheat and one boy will sit with a stopwatch to time you so we know
who was the fastest."

  Most of the boys were a bit nervous and shy about this but all wanted to
win the bag of candy.

  "Okay, any volunteers to go first?"

  Clint spoke up and rushed forward.  This got all the boys a little more
excited because if one was going to do it they all would.  Me and Clint
stepped outside the door.  Once outside and the door shut I grabbed him
from behind and hugged him tightly.  I thanked him for volunteering to go
first.  I took hold of his superman briefs and slid them down.  Running my
hands over his smooth buns I felt between his cheeks.  He had the butt plug
in him.

  "Oh my Clint.  This might be considered cheating.  I think you will win
this easily."

  We both and chuckled and I slipped a hotdog up into his hole half way.

  "I hope you can help me out with my problem later honey."

  "I will Billy."

  "Now go out there and show them how it's done."

  I draped the blanket over him and opened the door.  He took off and
easily made it to the other side.  Jayjay still confident from his earlier
win came up next.  He shut the door behind us and I told him to take his
boxers off.  The pair of Tommy boxers slid down his long legs.  The skinny
boy didn't have much of an ass on him but it would be tight all the same.

  "Umm how do I do this?"  he asked.  He was putting it between his cheeks
and it was slipping out of course.

  "It will stay in better if you stick it up your butthole just a little."
I could see him blush even in the dim light.

  "I'll help you get it in then you're on your own.  Just try to squeeze
down on it to hold it and get across the room as fast as you can."

  I parted his cheeks and eyed his tiny little hole.  I grabbed the tube of
lube and greased the end of the hotdog.  "Relax" I told him as I pushed it
against his tight little pucker.  It slid in and he straightened up and the
dog came straight out.

  "Let's try again Jayjay you can do it!"

  I slid it into his hole again and he let out a little gasp.  I covered
him with the blanket, wished him luck and told him to go.  He only made it
about halfway across the room before it came out and dropped to the floor.
Tommie came back next.  As he took his white briefs off I checked out his
hole.  It still looked sore from the night before.  He said it was.  I told
him the only way he could have a chance to win was to stick the hotdog up
his butt.  He said he didn't think he could do that.  I laughed and gave
him a pat on his rear and told him to be a naughty boy and do it.  His butt
needed to get used to having things up in it and a little pain and
discomfort now would help him out later.

  "I'll help you get it in Tommie."  I told him.  I generously lubed a dog
and started working it up into him.

  "Ohhhh stop Billy!  It hurts too much."

  "Quit complaining bitch you can do it."  I kept pushing it in until it
was a little more than half way in.

  "That's a good naughty boy.  See I knew you could do it."  I smacked his
ass and threw the blanket over him and sent him on his way.  He was walking
funny but he made it.  The boys cheered him and when he came back I pushed
and pulled it several times in and out.  He tried to muffle his cries but I
could tell he was in pain.  I finally pushed it all the way in and then
pulled it out.  He let out a big scream.  Several of the boys were asking
if he was alright and what happened.  I yelled out that he was okay that
he'd just stubbed his toe.  After several minutes Manny came back shyly.
He turned his back and slowly dropped his Sponge Bob briefs.  What a
delicious looking brown ass he had.  I handed him the hotdog and watched as
he stuck it between his cheeks and attempted to grip it.  I offered to help
him.

  I took the hotdog and lubed it.  "You will be able to hold it better if
we just stick the end of it in your butthole Manny."

  He turned and looked at me with this frightened look on his face.

  "What's the matter Manny?"

  "I-I-I can't do that." he stuttered.

  "I know you think you can't Manny and it sounds gross but really it's not
so bad.  Will you let me give it a try?"

  He looked like he was about to bolt.  "I can't.  My brother...." and he
trailed off.

  "Your brother what, Manny?"

  He looked down at the floor.  I knew this was going to be good.

  "Come on Manny you can tell me."

  "Well my brother tried to do that before and ...and ...ummm well it
didn't fit."

  "He tried to stick a hotdog in your butt?"

  "N-n-no his ummmm...you know."

  "His dick?"

  "Yeah that."

  "And it wouldn't fit?"

  "No.  He tried but he couldn't get it in."

  "Well he probably didn't know what he was doing and this is only a
hotdog."

  "T-t-that's about the size of his umm thingy."

  "Oh I see. How old is he?"

  "He's 12.  It's a little shorter but about the same size."

  "Yes of course.  Well I promise I know what I'm doing Manny and it won't
hurt at all.  It's just for the contest and I'd like to see you have a
chance to win it."

  "Okay. But if it hurts you gotta stop."

  "I will Manny.  Now you bend over and just relax."  I lubed a finger and
spread his cheeks.  I swirled my finger around his hole and slowly started
adding pressure.

  "I'm just going to get a little grease up in your butthole Manny.  That
will help the hotdog to go in.  You'll feel just a little pressure when I
push my finger in.  There.  Now that didn't hurt so bad did it?"

  "No"

  I worked my finger a little more into his tight brown hole.  This was
going to be too easy.  This boy had already tried it whether he'd wanted to
or not.  With my charm and experience his butt was getting some real dick
tonight.

  "Okay Manny you're doing good.  Just a little bit more and we'll be able
to get the hotdog in."  I worked my finger some more easing it up into him.
My own dick was rock hard and I wanted to just take it out and shove it up
his ass.  Some of the boys started yelling where he was.  They were getting
restless.  I called out that we were having problems but he would out soon.

  "Don't worry about them Manny we need to do this right.  Are you alright?
I'm not hurting you am I?"

  "No it feels full but it's not hurting."

  "Good."  I pulled my finger out then pushed it slowly back into him.  I
slowly started fucking my finger into him.  He let out a little gasp.

  "Yeah I think you're ready now for the hotdog.  See how much better it is
when I do it.  It didn't hurt at all.  Probly feels kinda good don't it?"

  "Yeah it don't feel bad at all"

  I grabbed the dog and strted pushing at his hole.  "I'm putting the dog
in now Manny.  You'll feel a little more pressure but just relax and let it
in.  You're doing great.  Just a little bit more."

  I kept pushing in slowly getting enough of the dog in so that it would
stay.

  "Okay it's all in Manny.  Now go out there and make it to the other
side."  He started off good but it fell out before he made it all the way.
He came back and burst into tears.

  "I'm sorry Billy.  It fell out."

  I hugged him and told him it was alright.  He'd given it a good try.

  "Now dry those big tears and let's get you back into your undies."  I
wiped his behind and helped him back into his Sponge Bob briefs.  I gave
him a light pat on his bottom and told he'd done good and he should be
proud.  He'd made it further than some of the other boys.

  Last one to come back was Clayton.  What a cutey.

  "I don't think I can do this Billy."

  "Oh sure you can Clay.  I helped your brother last year and he won and
now I'll help you."  I lied.

  I reached for his underwear and started to pull them down.  He slapped my
hand and told me he could get them off by himself.  Hehe the little runt
thought he was such a big boy.  When his briefs were lowered I stared at
his beautiful ass.  Yeah he had a butt just like his brothers.  Big and
round and made for pounding.

  "What are you staring at?"  He brought me out of my trance.

  "Your butt Clay.  I don't think I've ever seen a prettier butt."

  "It's not pretty it's just big."

  "No, no Clay. It is pretty and you should be happy to have such a big
pretty butt."

  He giggled and blushed.  I handed him the hotdog.

  "You should have no problem squeezing that betwen your cheeks and winning
this contest."

  He pushed the hotdog between his rouund cheeks lengthwise.

  "Okay Clay now squeeze real hard and take a couple steps."

  I watched as he took a couple steps praying that he couldn't hold it in.
And he didn't.  I reached down and picked it up getting an even closer look
at his perfectly smooth rounded globes of flesh.  I quickly pried his buns
apart before he had a chance to react and placed the dog back between them.

  "Now squeeze real hard Clay."

  I grabbed a cheek in each hand and pushed them together.  Just touching
them had my cock throbbing.  I thought back to the first time I fucked his
brother Kevin.  And Clayton would be even tighter.

  "Ummm Billy can I go now?  I don't think I can hold this much longer."

  "Oh sure Clayton, I'm sorry I was just daydreaming."

  I covered him with the blanket and off he went.  He didn't make it all
the way but did pretty good for someone just holding it with his cheeks.
Tommie had the quickest time of the 2 that made it all the way across the
room and I gave him his bag of candy.  I then had all the boys gather in a
circle and we sat on the floor as I began telling a scary story.


                           Other stories by this author:

http://www.nifty.org/nifty/gay/young-friends/first-camp/

http://www.nifty.org/nifty/gay/young-friends/eating-hotdogs-and-stuff

http://www.nifty.org/nifty/gay/adult-youth/halloween-helper/

http://www.nifty.org/nifty/gay/adult-youth/at-the-concert



  Thanks for reading and I hope you enjoyed it.  E-mail me with comments or
suggestions to the addy listed above.