Monstrous Dilemma -- post your advice in Comments

Sara I want to get your "input" on a problem I am
faced with. I have this desire to make my ass available to men w/big
cocks, T-girls w/ huge cocks, and women w/ big
huge strap-on cocks, all for a good hard pounding.

I also have this desire to shove big huge things up my
ass. Make that “monstrous things”. I've done it before
(see the note below about the shampoo bottle, for
example) and I loved it. The feeling of being
stretched by a huge “cock” is incredible. The feeling
of having my empty ass gape like the Lincoln tunnel
right after is something I equally crave.

Of course, the problem is that if I stretch that faggy
“pussy” of mine like I need, my ass will be looser
than my drunken sister during Fleet Week. I love that
of course, but I worry those men and T-girls with even
the largest cocks may not be so thrilled with my
sloppy loosened hole. At least a woman with a strap-on
can always just use a larger dong... Thank Goddess for
toys!

In my twisted sissy head I think of the benefits of
the loose ass, I can get fisted, maybe get foot
fucked, take two huge dicks at the same time, I’d feel
like the ultimate slut permanently opened up. But I
worry that I will miss out on some cock because they
don't want to bother with my altered ass.

For the purpose of demonstration, I've included a
photo of some of the anal toys I'm using so you know
what I am talking about. The black set is my anal
stretching kit. As I note in the photo, I am currently
at 1.5". I'll be moving through each larger sizes
after about every three weeks. I'm taking my time
because I want to be able to keep them in me for hours
on end (24x7 actually), not just a few minutes.

The 2.5 inch shampoo bottle on the far right is
something I put in my ass about 7 years ago. It took
about 3.5 hours to get it in and I didn't do any anal
prep in the months beforehand; just me in a hotel room
with lots of lube, time, and horniness. As soon as I
slid down on it (only got it in about 3 inches), the
bottle pressed on my prostate and could feel a big
blob of my cum oozing out. I got milked by my own
bottle; the first and only time I’ve been milked. The
problem was that I was only able to keep it in me for
about 5 minutes. I jerked my little limp dick and as
soon as I came the bottle was pushed out all on its
own from my contractions. I was gaping for a few days
after that, at the same time my ass was swollen for a
week; a strange combination for sure but I loved the
feeling.

So finally in the photo there is my Doc Johnson "Cock
and Balls" dong; this dong is 11 by 3 inches. It’ll
stay in it’s wrapper till it’s time to ride it. It's
next to a 2 inch diameter 8.3oz Red Bull can for
reference (a standard Coke or Pepsi can is 2.25
inches). This thing is huge; much bigger than a soda
can. I so want this in my ass... It is my ultimate
goal. I don’t want to just get it in me. I want to get
it in me all the way to the balls, and I want it in me
all day; like a giant buttplug.

So you can see that my intentions are pretty grand. I
have a lady friend, who suggested that there
are plenty of men who would like to fuck a
loose ass, and would totally get off on it.
In that vein, I know I would love putting my little
dicklett inside a woman who is stretched by a large
black cock and I would totally get off on it, but I'm
not sure it's the same thing. I suppose I could open
it up for a few weeks and then stop and let it shrink
back down for a while and start all over… Oh I hate
compromises like that! I wish I just had a built in
switch… “Push to activate the loose asshole mode”… but
it wouldn’t be as fun as going through the effort of
getting opened up using the toys.

Well I hope you can see my dilemma. Do I keep my ass
tight ass for those big cocks, or do I open it up like
the anal whore I that I am? What do you think Sara?

One thing is for sure, either way I’m eventually going
to end up in diapers when I get older… It’ll be worth
it.

From Sara: I had to consult with my sister ( a nurse ).
"The sphincter muscle will recover from being stretched as
long as it isn't stretched too frequently."