Date: Fri, 30 Dec 2016 23:15:09 +1100
From: Story Teller <storytellertripplex@gmail.com>
Subject: Jon's Family and Their Friends - Chapter 5

Jon's Family and Their Friends – Chapter 5

After that four way first session, things settled down a bit.  Mark
continued to fuck me and Ben, but Ben's ass got more of the attention as
Ben made it pretty clear his ass wants, needs, LOTS of attention.  When I
got fucked, Ben always wanted to be there supervising and then grabbing
Mark's dick for himself as soon as I'd come.

We didn't see that much of Sam after this as he'd worked out that for all
its voyeuristic potential our house had enough bottoms, but was a bit light
on for tops, my best topping efforts notwithstanding.

I went back to organising and going on occasional "dates", but Mark didn't
bring home anyone for a while as his cock was clearly getting as much
attention as it needed.

When Mark did finally mention that he had arranged to hook up with a girl
at her place in a couple of days Mark got all whinny and depressed.  I
realised then that it was time for the next stage in Ben's education as a
bottom.  It told Ben that if he stayed at home on Mark's date night I would
make sure he had a good time.  __________________________

In telling the boys that my "dates" usually involved being fucked I had not
told them the full story.  Yes, I was into being fucked, particularly by
big cocks, but I was also into serious assplay.

When Mark's date night rolled around, Ben and I had a light dinner and when
we finished I asked him if he was ready.

"Ready for what, exactly?"

"You'll find out in good time, but I'm sure you'll enjoy it.  Take your
clothes off and go into the bathroom."

Since I had given him the introductory course in douching, Ben had been
douching before each play session and said he was getting better at
cleaning himself out quickly.  Now was the time for the advanced course.

For this purpose I produced a flexible black douche attachment which was
quite narrow, but about 18 inches in length.  My bottom slut boy's eyes
widened with excitement when he saw it.

After he had cleaned out his rectum using the regular douche, I screwed on
the long black attachment, applied a generous amount of lube and got Ben to
bend over the toilet.  With all the fucking and all the dildos Ben had been
using, the first 8 inches went in easily, but then I had to feel around for
the entrance to Ben's colon.  When I found it the first few inches of the
douche attachment slipped in easily and Ben gave a "hmmm" of contentment as
the continuous flow of warm water was now being injected directly into his
bowls.

I rubbed Ben's belly gently and told him to relax his stomach muscles.
After about a minute, with me continually checking how he was going, in
noticed that Ben's belly had started to swell.  Finally Ben grunted he
couldn't take any more, so I pulled out the douche and let him release the
water into the toilet.  I then got him to walk around up and down the hall
for a minute and then called him back into the bathroom where I gently
rubbed his stomach again until Ben had to sit down on the toilet again
because he had some more water to release.

By my rough estimate, Ben had taken a couple of litres of water on this
first try.  As with anything to do with his ass, that was impressive, in
fact, amazing, given he was a beginner.

We repeated the process several times with me slipping the douche
attachment further and further up into his colon until it was all in.  Ben
also seemed to be taking more water each time as his belly would swell up
far beyond his usual slimness.  As I gently rubbed his swollen belly, I
kept getting hard thinking about how fucked up and perverted this all was.

Ben seemed to be enjoying the process as his cock remained rock hard except
at the point where he was getting very, very full and swollen and needed to
concentrate on relaxing his stomach muscles while keeping is anus clamped
shut.

For the next stage of the evening's entertainment, I took Ben into my
bedroom where I had set out a range of toys, all of which were either
fatter or longer, or fatter AND longer, than the toys Ben had been playing
with to date.  Again I enjoyed Ben's eyes widen in excitement and sparkle
with anticipation.

"Wow Dad, where have you been keeping these?"

"Well, you still don't know everything about this house and the things in
it," I replied cryptically.

I had previously given Ben a 12 inch black dildo which he'd been using for
depth training.  From among the toys I'd set out in my bedroom I selected a
smooth blue Crackstuffers toy which was about 18 inches long and a bit
thicker than Ben's black dildo.  "Why don't we try this one first."

I got Ben on his knees on the bed and rimmed Ben's pretty pink asshole lips
for a few minutes and then started inserting a couple of lubed fingers.
Ben shivered and squirmed in a very satisfying manner.  Then I lubed up the
toy and also squirted some of the cold lube up his ass.  Ben was shaking
with anticipation when I eventually took mercy on him and started working
the toy into his ass.

The first 7 or 8 inches slid in easily and then it was a case of feeling
around for the entrance to Ben's colon.  Ben had been working his ass with
the black toy solidly for weeks now (and let's not forget Ben being fucked
daily by Mark's huge cock) and so was used things going past the "second
sphincter".  I think Ben's bowels had straightened out and opened up a lot
in that short time.  It wasn't that difficult to find the entrance to the
colon and soon I had worked a couple of extra inches in.

"I'm really feeling that," Ben said.  The blue toy was only slightly
thicker than Ben's trusty black one, but was definitely a step up.

Pretty soon I had 12 inches worked up inside Ben's ass, and then we were
into virgin territory with Ben groaning up a storm.  I didn't want to
overdo it and so I just gently worked the toy back and forth, gradually
going a little deeper.  I think we got to a depth of about 14 inches in
all.

After losing his erection when I started going deeper, Ben's beautiful cock
was now back at full mast and Ben was working hard it with his fist.  When
I saw he was getting close to cumming, I pulled his hand off his dick,
slowly pulled the blue toy from his ass and told him to calm down a bit.  I
held up the toy to show Ben the lube high tide mark.  "Oh my god!  That was
amazing.  I want all that toy up my ass.  Why did you stop?" said Ben.

"Because you were about to blow and I have something else for you," I said,
holding up a fat silver Square Peg silicone toy.  This one, I thought would
be good for width training and was significantly thicker than the bronze
Square Peg toy I had given Ben after the first time I fucked him.

"Uh, wow, shove it in me now.  I want all of it," Ben groaned.  Such a pig!
(I wonder where he gets that from?)

Needless to say I didn't shove it in him immediately, but covered it in
plenty of J-Lube before pushing it up against his pretty pink asslips.
Even with the taper at the top of the toy and the give in the soft
silicone, it was a struggle to get the toy into Ben's young but expanding
ass.  In the end I had to get him to squat over the corner of the bed
facing away from me while I held the toy in place from behind him.  Ben
quickly got the idea and was soon sitting down on the toy so that his whole
weight was pushing the toy into his hole.  Even then the toy did not go in
immediately.

I told Ben to take it slowly, breathe deeply and just let his ass open up
and relax.  Nothing much happened for a minute or two as Ben steadied his
breathing and gently worked his ass back and forward over the top of the
toy, and then Ben groaned as the toy slowly started to slip inside his
overstretched hole.

I got Ben to pause, ease off the toy a bit and continue the deep breathing.
Once he had calmed down again I told him to start easing down on the toy.
Once again Ben moaned as the toy started to slip inside and then suddenly,
his ass was over the widest part and the remainder of the toy suddenly
slipped up Ben's ass.

"Fuck me dead," said Ben.  "It feels so good.  I've never felt so full."

I was thrilled by Ben's reaction, but I could tell he was struggling a bit,
so got him to lean forward so that I could slowly and gently pull on the
toy.  Nothing happened immediately, but I told Ben to push with his ass
muscles and then it was out with a pop and a huge sigh from Ben.

"That was the best, but now I feel so empty.  Shove it back in Dad!"  And
so I did.

Once again I got Ben to squat over the silver toy.  It was still a bit of a
struggle to get the toy in, but it definitely went in more easily this time
and Ben seemed more comfortable with it filling his hole.  After he'd
squirmed around on the toy for a minute or two I again got him to lean
forward so that I could pull the toy out.

After repeating this process half a dozen times over about 20 minutes, I
decided it was time for the next stage of the evening's entertainment.

After pulling out the silver toy I grabbed a black solid plastic butt plug
which was somewhat thinner than the silver toy.  (In fact, it was my old,
much loved trainer plug from many years ago.)  After the silver silicone
toy, the plug slipped up Ben's ass without too much difficulty.

Ben was humming with contentment, so I told him to lie back on the bed and
relax.

I slipped into the en-suite briefly to relieve my swollen bladder.  When I
came back into the bedroom I brought a tray with another set of even bigger
toys.

Ben's eyes goggled and his cock jumped while he squirmed around on the
embedded plug.  "Fucking hell Dad, they're huge!  I'm not sure I can take
any of those," Ben said.

"That's OK, as they're all for me."

"What?!  Shit!!  Double fuck me!  You're into huge toys?"  Finally the
penny dropped with Ben that he wasn't the only bucket bottomed slut in the
house.

Ben's eyes bulged when I selected a blue dragon toy, lubed it up and
started working it into my ass.  "Just for a warm up." I joked.

"Wow, Dad.  That toy is huge.  You can take all of it?"

"You'll find out soon enough."

I quickly slid down the toy to until my asslips reached the huge bulge
above the base.  Then more slowly I started forcing my ass down over the
bulge.  I let out a solid grunt when I passed the widest point and my ass
slid down over the remainder of the bulge and the base pushed up against my
hole.

"It's been a while since I was on this toy, but I guess it's like riding a
bicycle."  Another pathetic joke.

Ben had climbed down from the bed and was sitting on the floor about a
metre away from me with his eyes riveted on the blue toy and my ass.  Now
he started pulling on his cock again and looked around at the toy selection
I had laid out for him earlier.  He got up, pulled out the black butt plug
and then grabbed its slightly fatter big brother.

"Don't rush things," I told him.

I should have saved my breath, as Ben pushed the bigger plug up his ass
with his usually reckless enthusiasm.

For the next hour we worked our way through the two sets of toys, the
smaller ones for him and bigger for me.

We concentrating on our asses so much that neither of us paid that much
attention to our dicks.  Finally, when my ass had had enough of the huge
toys (though Ben still looked keen) I called a halt.  I got Ben to reinsert
the second smallest of the black plugs.

I climbed onto the bed with Ben and got us into a 69 position and started
working on his swelling cock with my mouth and throat.  Ben in turn was
eager to demonstrate his improving oral skills on my big cock.  (He still
has a way to go, but compared to his first efforts week ago he is
definitely able to take my cock further down his throat with less scrapes
from his teeth.)

I lubed a couple of his fingers and guided them to my lose asslips, so Ben
was soon exploring the folds of my ass while trying his best to get my cock
down his throat.

At the other end of the bed, I was working Ben's cock in and out of my
throat with practised ease (if I say so myself) and gently playing with the
plug up his ass.

After the intensity of the full on assplay, it took us both a while to
relax, recover our erections and start to build up towards orgasms.  17
year old Ben was, inevitably, the first to blow his load, which nearly
drowned me; after catching me by surprise, Ben's cum spurted out of my
mouth, was all over my face and the sheets and still he kept on shooting.
This was too much for me – a hugely messy facial from my younger son
after a long session of assplay sent me right over the top.

Ben had kept his lips locked around my cock as he came and tried to swallow
as much of my cum as possible, but it was the biggest load I'd blown in
ages so a fair amount of cum ended up spread across his smiling exhausted
face and in his fine blond hair.  It was the most beautiful thing I've ever
seen.