JO

Time was, I’d do it anywhere. My first industrial jerking off took place in grammar school (my school system had no Junior High School) in the eighth grade. I became an expert in leaning my chair back, rocking slightly and rubbing my dick against the frame of my desk. Gently…back and forth…discretely. One of my classmates, Megan, was 14 going on 24, with a developed body and a firm grip on her own sexuality. Above average height with a meaty, athletic build, she cut an imposing figure, even in the eighth grade. She wore jeans so tight that it must have taken a half hour to get them on. And the back seam disappeared deep into her ass crack in the form of a mega wedgie, fueling my earliest ass fetish moments. Damn, she was hot...and seated two rows ahead of me. I even discretely ejaculated from my rocking chair position on at least two occasions, but after leaving a tell-tale wet spot on my pants, I learned to control my urges.

From that early start, I became a dedicated masturbator.

Getting a frenum piercing changed everything. Well…not quite like when I had stitches in my “good” hand and realized that I was a one-hand jerker-offer….but I digress. In order to have a painless JO session, I have to carefully place the frenum between my index and fore fingers, and keep it there throughout the whole process. Sounds like a pain, but it really isn’t. One other change the frenum has introduced: it is harder to do the act while sitting down, making the bed the new and improved place to jerk off. Not that I CAN’T do it while seated, it’s just that there is more potential for snagging the frenum if not lounging. I don’t know, it’s hard to explain …just take my word for it. So lying there and getting in the mood I will conjure up a variety of images, but when I really get rolling, I end up thinking about one individual. I just cannot shake it. Lately, there is a small part of me that feels like this is some sort of cosmic imposition; I can’t figure out if it’s cool or not. Then there is the whole matter of WHAT am I thinking about. Am I thinking about stuff that we do already? Well, yes. But those “appropriate” thoughts are ‘enhanced’, as our former Veep would say, by other thoughts, mostly of the anal worship variety. Tongue in asshole…mmmm, yes. Talk about motivation. My fave vanilla position, practiced many times with my ex, consisted of my tongue deep in her asshole, with my ex tugging on my nipple clamp chain with her left hand and rubbing one out with her right. But it seems like I’ve said this before. And maybe that’s not such a “vanilla” position, after all. No matter. Repetition is good and I hate categorizing things, first and foremost what I am and what I like. So, it’s rare for me to have a JO session without somehow getting to the point where I am dreaming of performing anal worship under painful duress, not to mention being given firm feedback on the merits (or lack thereof) of my performance. Actually, a current variation is to dream of performing this fete with my cock locked into chastity. That’s a whole other subject, of course, but the notion of jerking off while fantasizing about chastity strikes me as a little strange…even though I do it all the time. I love to dream about my Mistress climaxing several times in the position road-tested by my ex, while taunting me about my inability to get really hard, never mind ejaculating. (I always whimper, I know, Master, you have to come for both of us.) Since she is so sweet (not everyone knows this, ha!), after finishing the session and going out for a drink, she invites me back to her space for a brief post-script. Upon entering, I am told to drop my drawers and assume the kneeling position. Mistress mater-of-factly attaches the nastiest combination of nipple toys she has and coldly tells me that I have 90 seconds to ejaculate. Failure will mean six uninterrupted months in the chastity device. While jerking off to this well-rehearsed routine, I never fail to have a spooge explosion approximately 15 seconds after embarking on this last mini-scenario. In my dreams, as in a real life (live?!) session, I lick up the ejaculate and am cheerfully sent on my way by my Mistress. But I’m forgetting a few details. Not about my fantasies, but about how they are executed. You see, I cannot ejaculate if I am not being tortured. Truth. (Poor Keith Carradine. I relate to his predicament, though auto-erotic asphyxiation has never been my bag.) But while I may dream of zippers and nipple stick/clamp combos, I have a couple of very tight clothes pins that get the job done quite nicely. I will twist them as I slowly work my way up the ladder; I’ll imaging that my Mistress is using alligator clips, twisting them until I cry (which makes her laugh). She punctuates this with a series of spits. I know she prefers to sensually allow a stream of spittle to slowly decent into my mouth, but I dream more of her curtly spitting in my face…which I do not regard as a humiliating act, but rather an act of anointment. Then I dream of her gazing at me, expressionless, cool, not terribly amused until a tear gathers up and dribbles down my cheek. And then I’ve come again, this time a thinner, more watery version. Totally out of breath and slightly spaced

All of the above can easily take a couple of hours if I’m not careful; a ridiculous indulgence of time…and then I’m asleep with a smile on my face.