Bondage Boy has quite a collection of ass toys and he’s really given ALOT of thought to how far he’d like to be stretched. Thing is…dont know if you’ve noticed in the pictures but he’s a TINY human. So tiny…I’ve gotten a good chuckle in some of our convos in just how far he thinks he can go and I’ve certainly used toys in his current range. But, a couple of weeks ago he mentioned that he’d like to finally get this FUCKING HUGE butt plug fully in his ass and has even gone so far as to give me “pointers” on how to successfully get it in. Really? thats so cute… I just giggled and made a mental note to punish him and remind him later… never assume you can predict me. Ever. I believe people reveal themselves over time.

New inflatable hood…something about a latex hood over a stuffed and taped mouth makes me nervous, even with internal reinforcement of his nostrils with tubing I think the pressure on the nose from the latex just makes me overly paranoid of lack of oxygen so we had to switch to his leather hood which has holes in the nose area so I can extend the tubing and verify he is breathing continually, if needed.

Balloon Head:

Noir was on hand for his visit this week. She’s so much fun for me to play with. However, this week she planned on letting BB know she didnt appreciate getting cut by a restrainst system he had built (pretty serious cut from a rough metal corner) and I figured; what a great opportunity to teach BB a lesson. Yup…

 

Email From Bondage Boy:

Today I was given an extremely special treat:
All 4 P’s – Pain, Pleasure;  Punishment, and Predicament!
And it was VERY MUCH FUN!
It was everything BDSM, kink, and perversion is about!
The whole ball of wax.
 
First I was cuffed, arms behind my back.
Then the earplugs.
The latex blow-up hood was put on halfway,
so I could not see.
Then I was gagged with dip and the pump-gag.
Attempts to put the blow-up hood on the rest
of the way worried Holly, so she removed it,
and laced on the leather hood.  The straps
we fastened and I was moved to a standing
position, facing a table.  My head was pushed
down onto the table so that I was bent over.
The gag was inflated and words were spoken
to me.
 
Ms Noir joined Holly and they told me I was
going to be punished.  Then it began!  A
plethora of paddles, whips (including the
nasty cat-o-nine tails), canes, and bare hands
smacked my buttocks hard.
 
Punishment is supposed to hurt to teach a lesson.
I had a lesson to learn.  But as it is with others
and often at parties, the power exchange was
incomplete.  My legs were free and I could have
run away.  But I knew I deserved the punishment
and submitted to it anyway.  I was able to control
the intensity somewhat, though, by moving away
from the harder blows and lifting my feet to
show agony levels.  And because I was in a
submissive mind-set, but not in bondage, it
truly was pure punishment, with no aspect
of pleasure.
 
There is such a fine line between punishment
and pleasure for me, that it is difficult to explain.
But something about being unable to run away
and flinch and exhibit signs that the pain is
strong enough can make even the most severe
punishment pleasurable.  But that did not
happen with the spankings.
 
Next I was secured to the table on my back
with my wrists and ankles high and spread.
I was given my huge 2 3/4″ dia 9″ long butt-
plug to hold in my right hand and told “This
is going inside you today!”  I got extremely
worried and an instant erection.  I shook my
head as I thought about it and had hoped
maybe Holly would reconsider.  I had a lot
of time to think about it, too, while the two
dominant ladies took a long break.  I think
they were planning their attack on me and
holding that anal toy just kept reminding me
that I was in deep shit!  It was the first of
many predicaments.  What if I threw the
thing on the floor?  Would it make them mad?
Or would it signal them that I don’t really
want this huge thing up my ass today?  I
thought how do I get out of this?  But then
I would drift off into sub-space, my cock
throbbing with anticipation.
 
Finally, I felt lube being applied and lots of it.
OH oh!  This is it!  I tensed up.  The rubber
toy was removed from my hand and greased
up.  “Here we go!”  She said.  And in it went,
slowly and methodically, wiggling it in with
constant pressure, backing off, then bearing
down again and again.  Almost all the way in,
the pain was intense and I could not take any
more.  Then a vibrator was put on my cock
and I would relax and get aroused.  As I
relaxed, the plug was pushed in still deeper.
The vibrator was stopped before I could cum.
And that was repeated several times.  Then I
was fucked with the probe a few times–all
the way out and all the way back in.  But still
it would not quite go all the way.  “It is going
all the way in!  So stop fighting it!”  I heard.
I tried to relax and let it in, but could not.
Punishment or Pleasure?  A bit of a predicament
for sure!  If I let it in all the way, then I’ll
probably get to cum and this will be over.
So my mind told me to do it, just let it happen.
But it didn’t.
 
Then came the most intense and wild
PREDICAMENT I have ever been placed in!
I was unfastened from the table, moved
to a bench and forced to SIT on that huge
butt-plug.  As my body was forced down
upon it, I was resisting and holding myself
up with my arms.  Holly tied my wrists to
the bench and then sat back and watched.
“How long can you hold yourself up?” she
asked.  My buttocks were only 2″ above the
surface of the bench.  If I just let the damn
thing in I could relax and sit on them.  But
try as I could, it was too painful.  And I kept
slipping and the plug would go in a little
deeper.  Then I’d react and push myself
back up off the thing.  There was that evil
laugh and more words highlighting my
predicament.  “This is fun to watch.  I
have lots of time.  Eventually your arms
will get tired and you will sit down on it.”
Another evil laugh.  My cock loved the
whole predicament and was very erect.
Vibrators were applyied again and again
bringing me closer and closer to orgasm,
and then nope, not yet, “You have to sit
all the way down if you want to cum.”
 
I don’t know how long this went on.  It
seemed like forever.  Finally, I was allowed
to cum even though the plug did not ever
go ‘home’.  It was removed and I was
released.  The most satisfying sense of
fulfillment and happiness came over me!
Mmmmmmmmmmmmmmmm!
 
Thank You!
 
A most wonderful day!
A most wonderful woman!
 
I have a feeling that today’s predicament
will be repeated.  OMG!
 
Bondage Boy