Top Ten Worst Things Iíve Ever Jacked Off To

Bill Dungsroman 12/19/2002 

Before going into this list, Iíd like to point out that somehow, after all the times Iíve beat my meat, I have never ever been caught. Oh, itís been a close call a couple of times, sure, but never actually caught en medias of pumping my monkey. Apparently, I have some kind of fairy godmother for this kind of thing, one whoís as filthy and demented as I am. Bless her.

10. Next to my girlfriend while she slept

Yeah, this one is pretty tame, but there it is. I simply didn't want to wake her up and go through the whole foreplay rigamarole. Ashley and I had been going out for over a year at that point, so I was in that period between loving sex with her all the time and getting a little tired of always having to get her worked up for it. Not that I don't normally enjoy that stuff, but in this instance I just wanted to crack one off and go back to sleep. She was living with me in my parents' house (her mom had kicked her out, I loved this bad girl), and all my porn was under the bed. I would have woken her trying to sneak into the bathroom, and if I took too long, she would either think I had jacked off or taken a shit. Neither of which seemed to appealing for her to have me jumping back naked into bed with her, I figured. So I slid carefully out onto the floor next to her and smacked it while I made sure she didn't wake up. I did that by staring at her the whole time. I canít even imagine how fucking creepy that must have looked, especially if she had woken up and seen me glaring at her, pumping and grimacing like a frank psychotic. This is so far up the list since an actual female was in the vicinity, but itís still gross.

9. Scrambled Cable Porn

Again, nothing too original here (that's for later. Oh my, yes). If you havenít jerked off to scrambled cable porn, then you havenít jacked off enough, you freak. However, add to the fact that this was really really scrambled porn, such that I couldn't even hear it (every few seconds there was a too-loud BZZT sound, so I had to keep the volume down), and I couldn't even really tell what was going on. Thus, I was masturbating on faith that whatever was on the TV was probably porn. I was masturbating to the assumption of porn, with only the most circumstantial of evidence to go (off) on. It could have been Back to the Future III for all I could tell. Were that the case, masturbating to Christopher Lloyd would be much further down the list.

8. Half A Naked Breast, Drawn In A Battletech Comic.

Could this be any geekier and more pathetic? As it turns out, yes. I did it with my friend's comic, in his bathroom. It wasn't even a fully nude breast, and it was about a quarter-inch in size. Sad. The only mitigating factor here is that it was less than 2 months after I'd first discovered beating it, and a stiff breeze could have done it for me at that point. I took one look at that tiny little collection of lines (oh yeah, the comic was in black and white, even), got a hard-on, and had to deal with it immediately. Still, Battletech, my friendís room, it all adds up.

7. JCPenney's Catalogue, Lingerie Section

Oh, Victoria's Secret was just too good for me, it seemed. Well, actually it wasn't, but whacking it to that mag is practically an American institution, like National Geographic. JCP's is far more lame, since it's in black and white and the models hardly look like Tyra Banks. More like Ernie Banks. And less nudity than a circa-1950's beach movie. Why even bother looking at anything at that point? God, life before our modern internet was awful. Itís a good thing I never got a hold of those ASCII nudes back then, Iídíve thought Iíd hit paydirt.

6. A Traci Lords Poster

Yeah, so what? Well, first of all masturbating to still pics of porn chicks is pretty weak, like composing love poems for a hooker and reading them aloud to her during your hour. Also, she wasn't actually nude, just in a little bikini bottom and a wet T-shirt pulled up above the bottoms of her breasts. And, oh yeah, I didn't know she was in porn, I was 13 at the time (my eternal jack-off defense Ė "I was 13!"). And I bought it in a comic book store, a goddamn comic book store. Yes Iíll take the new issue of Power Pack, Robotech Macross, Dynamo Joe andthatTraciLordsposter. And it took me 3 months to work up the giddy courage to buy the fucking thing in the first place. I still get a little stirring of the nether regions to think of it, even. Yuck.

5. Ah, The Top Five: My Best Friendís Mother

Now we have fun. Again, this was in my early teens, but still. It was his mom, not his sister (he didn't have one, alas). Hey, she wasn't fat and ugly, you know, and I would estimate in her early 30's at the time. Y'see, one time I saw her with only a shirt on and nothing else. Boom, that was that. Wack City. This was not a one-time event, either. Mikeyís mom was good for a couple of months HEHGELRGLHLELGER.

4. Howard Stern's Radio Show.

This appears pretty stupid at first glance. Apparently, perverts across the country do this, legions of jobless fucks laying around in their gray underpants. Great. But hey, it was the multi-orgasmic chick. I have a particular weakness for female moans of pleasure. Better (?) still, it was in my car on the way to work. Thank God I had a spare workout towel handy, I'd already started without thought to what was going to happen next. I just suddenly had my erect penis in my hand as I pulled shakily (no pun intended) into my work's parking lot, around back. I went off like tube of toothpaste whacked my a sledgehammer. See, every so often I try to curb my onanistic pursuits, since itís filthy and wrong and shameful. At that time, I was limiting myself to Thursday nights only. Guess what: it was Thursday. I was at full charge. My oh my, if one of my coworkers had seen me, that would have been it. Thank you again, Fairy Godmother.

3. My Female Former Roommate's Pillow While She Was Out Of Town.

Oh you sad, sad little man. But she smelled really good, you know, she had all this blonde hair and...oh forget it. Lisa was the sweetest, prettiest little thing you could ever hope to meet. She was a year ahead of me in medical school, and we rented out rooms in this weird house that was near the hospital. It was, in essence, a house that was converted to a doctorís office and then back into a house. The landlord was a demented old bag whoís husband (the doctor) had died and left her drunk and lonely, and a controlling spiteful bitch as well. Boy, did it ever suck living there. Sheíd show up around 7 AM on Saturdays, after weíd both spent around 70 hours at the hospital the previous week. Sheíd want to talk, as in carry on conversation. Then sheíd nag and pretend she was our mother, and if we complained about problems with the house, sheíd blame them on us and come up with excuses for why they canít/shouldnít be fixed. She probably didnít have the money, but if sheídíve been honest, we would have been understanding. Instead, it was the end of January and we hadnít had working heat for three days, and I had to threaten to move out and sue her if she didnít fix the fucking heat. I was gonna move out anyway, but then Lisa pleaded with me to stay there with her. Goddammit, those big blue eyes and little hands literally tugging on my arm, pure fucking Kryptonite. We slept together on the living room floor in front of a space heater. That stupid fucking landlady. I should have known she was nuts, her kids went to medical school back East, as far away as possible. She even yelled at Lisa for the heat being busted, and Lisa stood there apologizing. I flipped out and told her to get the fuck out of the house until a repairman came. What are you going to do for heat? She asked, suddenly concerned. Burn the fucking broken mailbox in my broken fucking shower! I screamed. I actually ended up having extremely nice sex with Lisa (once), but before that, right after the heating debacle, she went out of town and I slept in her bed, under her pillow. What a great girl. Ah, who am I trying to kid? Pathetic, disgusting, perverted, horrific. Pick the adjective.

2. It Didnít Pay Much, But It Had Great Perks

Iíll make this as quick as I can: I used to jerk off outside of hotel rooms when people were having sex during the graveyard bellman job I had. What a great job that was. I worked midnight until 8, and I was the only bellman there. I had the job all through college, and I started this late-night maneuver a few years in, during my Sophomore year, I believe. It took a little preparation, mind you. Should I pass a potential room, I had to spring into action immediately; who knows how long it would last? The national average for intercourse is between 5 and 10 minutes, time is obviously of the essence. The plan was simple, clever, and effective. I ran into the maid's closet and pulled out a rollaway bed and a towel. Then I positioned the bed near the door in question, in a wedge to block off my lower half. Then I beat it furiously, with one ear and both eyes on the hallway around me for anyone to come around. The towel was to catch the goods, but sometimes I just let it fly. Then I'd walk with my cock hanging out, with the rollaway bed concealing it until I could get to the maid's closet to clean up. I was never caught, somehow. And I was never interrupted, praise the Lord, pass the Vaseline. But I did have to walk by a few guests immediately after, with the bed and all. "Good evening folks" I'd say all-too-cheerily, flushed and slightly perspiring. One rule only: NEVER find out who was actually in that room. Eesh. I should have kept a chart of all the rooms I "did" and treated myself to a sundae when I "cleared" out a floor. Hey, you gotta have goals.

1. Oedipussy

While my mom had sex with her boyfriend in the next room. Beyond comment. Freud, wherefore art thou?

Bill Dungsroman

page 1