Random Rim Jobs

I don’t understand why anyone would not masturbate. It’s free, fun, and satisfying.

I began masturbating when one of my mother’s girlfriends – my mother called them “lovers” – Cindy, told me I should be doing so.  I think I was nine or ten.  So Cindy told me I should be masturbating.  I knew what it was, but just didn’t know how to go about it.

I figured the way to go was to put something inside me.  Something phallic.  I settled on a pencil.  An extra-large novelty pencil.  The ones sold at amusement parks to stupid kids like me.  Impossible to sharpen well because they wouldn’t fit in any pencil sharpener.

I put the eraser end of the novelty pencil in my virgin pussy and felt … not much of anything.  I was a tad disappointed.  This is what I was supposed to do?  What was the damn point?

However, I persevered.  I tried putting other objects in my pussy.  One I particularly liked was an incandescent light bulb-shaped novelty eraser.  This novelty, however, was much smaller than the original item after which it was modeled.  I liked it because though it was small, it was the largest thing that had entered my virgin opening up to that point; I liked the way it stretched out my tight hole.

My hole isn’t nearly so tight now, but I still like the feeling of my opening being stretched.  When I masturbate now I put large toys in me, and sometimes more than one if I’m in a pinch.

Eventually the eraser wasn’t enough.  I went back to the over-sized pencil.  I found that the metal attaching the pencil eraser to the wood shaft of the pencil felt very nice, but only right at the opening of my pussy.

While what I was doing was mildly enjoyable, I still did not understand why Cindy had been so encouraging.  It was more thrilling for me to sneak cigarettes because at least I was told that cigarettes were verboten.  I needed to up my game.

I began walking around with the big pencil in me.  I only walked around for short times, and when I was at home.  That at least made me feel like I was getting away with something naughty, but it still didn’t do much for me.

I had no clue what a clitoris was, and certainly didn’t know that it was the key to anything at the time.  I figured out there was something going on in a place other than my vaginal opening during dry humping sessions with various boys years later.

Eventually I simply gave up.  I never came.  Well, I did, but not until I was sixteen, and with the help of my high school girlfriend, Erica.  [All my posts with "A Diary Entry" in the title are from this era.]

I didn’t masturbate again in earnest until I was around seventeen.  One time I bought a cucumber and peeled most of it, leaving a handle so I could fuck myself with it.  Cucumbers are fun sex toys.

My friend Laura bought me my first “real” sex toy, a dildo.  The sex toy that was actually meant to be such and was actually used as one.  I had had a cock ring in high school, but I wore it as a bracelet.  I knew it was a cock ring, but I didn’t know what a cock ring did or its purpose for doing it.

Laura bought me the dildo after I bought her her first vibrator.  I am proud that I got her to masturbate; before she had the vibrator she was afraid of “the pink snapper.”

So with the new dildo and my fingers I masturbated, a lot:  Dildo fucking my pussy, fingers rubbing my clit, clockwise.  It was while doing this that Laura once caught me masturbating.  I was not ashamed of my habits any more than I am now, but masturbating in front of someone is not the same as masturbating alone.

Laura knocked on the door of my tiny studio apartment.  I was in the middle of doing my thing so I said, “Don’t come in.”  Of course she only heard, “Come in” and she did.  I screamed.  She retreated back outside.  I scrambled to get dressed and then opened the door, quite red-faced.

Obviously I recovered.  Now I masturbate, and often.  I’ve even masturbated for an audience … of one, possibly two.

I don’t understand why anyone would not masturbate.

I swear.  True story.