Biggest...

OK, so Eve won the first round of question asking, and she came right out of the chute determined to embarrass the ever lovin' bejusus out of me.  Her question was:

"...what's the biggest thing (plug, dildo, whatever) you've put up your butt? I'm talking more diameter than length."

Well, Eve...if you were talking to my wife, her answer would be my head!  BWAHAHAHAAHAH!!!

OK.  No, seriously.  What was the biggest thing I've ever put up my butt?  As soon as I saw the question, I knew exactly what it was.  But it will take some 'splaining, cause it is a bit...unorthodox.   I mean, I could come right out and just say "It was X, and it was Y big around", but how boring would that be?  So bear with me as I bore you with backstory...

First off, I don't like big toys.  I like to be comfortably filled.  So if you look at most of my toys, they appear on the smallish side.  Secondly, I discovered my love of anal play at an early age, say 13 or so, even before I had masturbated to climax.

So this is a tale of my early days of anal exploration.  When I first discovered anal play, I used my finger exclusively.  Which, while good, is a bit awkward.  Sex toys were totally unobtainable for a young teenage boy in a small Midwestern town, and K-Y was the only lube available in drug stores, other than Vaseline.  So, being all creative and the like, I struck out to find suitable substitutes.

(Now, what follows will be a list of things that I have put up my butt.  Looking back as an adult, I know how STUPID and DANGEROUS many of these things were, and that I could have gotten them lost up there, and etc, etc.  I'm (relatively) smarter now, so...)

The first thing I started to regularly stick up my butt were Bic Stic pens.  While this gave me a sensation, there really wasn't much to them, so it wasn't a lot of sensation.  I wanted something a bit wider, to give me some more fullness.  So casting about, I tried all of the below (and more) at various times during my teenage years...

The handle from an old hairbrush (not too bad, and safe...good thickness, and no chance of it getting lost up my butt)
Handle of a screwdriver (interesting sensations, especially if I got it in past the grip part and spun it)
Carrots (this was the only food item I tried.  Mom never had cucumbers, and hot dogs seemed really icky.)
Glass Coke bottle (seems like it should have been fun, but was actually kinda painful...)
Handles from various kitchen implements (yes, ick.  At least I always put them in the dishwasher afterwards)

So, I finally settled on two go to items...almost perfect in size.  The first was a plunger handle.  Not too big around, and plenty of length.  I used to cover it with a rubber glove to a) keep from staining the wood with Vaseline and b) prevent splinters.  Now, of course, this was a rubber glove that my mom used to protect her hands while cleaning with stuff like bleach and the like.  Like I said, stupid teenager...

Second item was a candy thermometer I found in the back of a drawer.  Nice size around, and I had never seen my mom use it, ever.  Kept that one in my room, in the back of a drawer.  And once again, can you say dangerous?  Sticking a hollow glass object in your butt?  Crazy kid...

So life was good.  I had a couple of great home made toys.  I was masturbating up a storm with my homemade dildos whenever I could.  Happy happy.

But, as is always the case, I was never quite satisfied.  I kept looking for bigger and better makeshift toys.  I wanted to push the limit...but then again, who doesn't?  Right gang?  Right?

Anyway.  One day, when helping my dad clean out a back corner of the basement, I found it.  Found the one big item that I thought would be perfect to try!  So...what was this object?

Well...I am somewhat embarrassed to say, this largest object was the collapsable oar from an inflatable raft.

OK.  You can all stop giggling now.  Yes, I'm looking at YOU!

But you have to understand, it was perfect!  Let me describe this.  It was a two part oar, consisting of a three food handle, hollow yellow plastic, that you inserted and screwed in the blade section into.  This three foot handle was what I focused my lust on.  It was round, with no knob on the end or anything, just a rounded end on a shaft.  The only issue that I saw was that the handgrip area was roughened with little nubs to give you a better grip.  And not rounded little nubs...these were pointy little nubs.  Ouch.  That would have to be dealt with.  Other than that, it was perfectly round, straight, and (pay attention to this part) just a little bit bigger around than I could get my 16 year old hand around.

Can you say my eyes were bigger than my ass?  Unfortunately, this has always been an issue for me.  I have learned over the past couple of years what my comfort limits are, but for a while there, I kept buying toys that were way too big for me.  And this oar handle, at probably a good 2 1/2 inches in diameter, definitely qualified as too big.

So the nubs on the oar.  Not a huge problem for a resourceful young lad.  A bit of work with an Xacto knife from my hobby kit and some fine grit sandpaper, and I got that problem MOSTLY smoothed out.  It wasn't perfect, but I deemed it safe enough.

I waited for an opportunity to try out my new toy, impatiently.  I didn't want to try it in the house with other people around, I wanted the house to myself.  So after a couple of weeks, I finally just faked being sick, so I could finally try it out!!!

So I waited until about an hour after everyone left for work, and gathered my tools of the trade around me.  Some of my dad's porn magazines.  Tub of Vaseline.  Towels.  Plunger and rubber glove.  And finally, the oar.  I laid down on my bed,  applied plenty of Vaseline to my asshole, working some in with a finger as far as I could.  After working with my finger a bit, I took the plunger and slid it in as far as it could go with the glove over it, to relax myself and just work myself up to the main event.  Fucked my ass with the plunger for a while, stroking myself until I was hard, reading porn mags until I was nice and relaxed and ready to try it.

I took the oar, and applied a liberal coating of Vaseline to it, pulled my legs back against my chest, put it against my asshole, took a deep breath, and pushed it in.

Or rather, I tried to.  There was just no way it was going in.  I took a deep breath, redoubled my efforts, pushed harder and pushed back against it, and barely got the rounded part of the oar to slide in, before it hurt too much and I had to stop.

Well, color me annoyed.  My nice erection was gone, and this oar was thwarting me.  (Heh. Oar.  Thwart.  Nautical humor.  I crack myself up.)  A sane man would have given up...but we've already established that I'm pretty stubborn.

So I switched positions.  Face down on the bed, on my knees, butt up in the air, trying to relax and open myself up as much as possible.  More lube on the oar handle, and then...slowly...ever so slowly...I worked and twisted the handle against my ass, in a little, then back out, in, out, in, out...until finally...I felt myself open up, and it slide into me.

But oh my GOD, did it hurt!  It burned so bad!  It was not pleasurable in the least!  I though about trying to keep it in, see if it got better, but I just couldn't take it.  So I (for curiosity's sake) marked it with my fingers to see how much I actually had in me, and slid it back out.  Ah, sweet relief!!!

I looked at how far I got it in me.  a measly 3 inches.  Damn.  Felt like the damn thing was in about a foot!  Hmph.  So much for the great oar toy.

So I cleaned up.  Put the porn away, returned the plunger to the bathroom, threw the oar back out into the garage.  Didn't even bother to come that day...my butt was too sore.  No damage done, but I didn't ever try that oar again, and laid off of the  ass play for quite a while.

And so there you have it, Eve.  The story of the largest thing I've ever had in my butt.  Hope you're happy.  I'm going to go over in the corner now and die of embarrassment.