Top Ten Worst Sexual Experiences (page 2)

5. Unwelcome Bodily Fluids, Part One

My second "real" girlfriend (a girlfriend qualifies as "real" if I get to fuck her, of course), Ashley (no relation to barfly Ashley, you may know this Ashley as #10 from my Top Ten Worst Things I Have Ever Jacked Off To article), was a voluptuous redhead I met through my workout partner. I was 19 and had been weight training for about two years (yeah, I had a nice long dry spell for awhile there), and had jumped from 130 to 160 pounds. So I didn't look like such a wimpy fag anymore. Ashley was great for my self-esteem. After I met her, I gave her my number to give to her friend (Ashley had a boyfriend), but she kept it and called me a couple times before finally just telling me she wanted it. We had sex the first night, and she dumped her old boyfriend a few days later. Man, we had sex all the time. Two or three times a day, this girl was single-handedly responsible for my sexual maturity (such as it is). Once though, early on, something happened that I wasn't at all prepared for. I was doing her doggy-style on her bedroom floor, flailing away like I usually do. I felt a warm rush of liquid and thought that maybe Ashley had come, but she wasn't squealing in orgasmic glee or anything. Of course, it was blood.

It kind of smeared out of her pussy onto my cock, and then up her asscrack and my pubic hair. Already having a firm hold on her ass, I spread her butt cheeks apart for a better look. For a selfish split-second I thought Did that come out of my cock?

"Ooh yeah." She liked the butt-fondling.

"AAAHH!! You-you're bleeding."

"Oh. Must have nicked something."

Must have nicked something? My cock is neither large enough to stress a well-lubricated vagina, nor does it have sharp or pointy bits. Eech. We hit the shower. She tried to placate me with a blowjob, but she was never very good at that, and could never bring me to orgasm. So in addition to the Hysteric Hemorrhagic Horror, I had to comfort her over her incompetence at sucking me off. I'm such a trouper.

4. ‘Taint Ass, ‘Taint Pussy. ‘Taint Skin, Either.

Purveyors of, well, practically anything I write will know I have an ex-fiancé, a pretty little redhead whose comely outward appearance served quite well as a misleading shell for a dark, twisted, cold soul. But enough about that, once upon a time we were happy and having fun and fucking and the whole enchilada. Speaking of Mexican food metaphors, I used to love licking her little pink taco, garnished as it was with fiery red pubic hair. Once, however, things turned to tragic. I had her on my couch, and had slowly slid off her little panties for another round of Flick The Button. I settled in between her coltish legs and decided on a whim that I'd give her little butthole a roundy-round to warm things up. (P)oops, guess what I found hanging menacingly from a red taint hair? A small but significant lump of shit, caked and hanging there. But I loved her, my lush little façade of a caring person, so I redirected back to her pussy and tried not to brush the dingleberry with my cheek. And I fucked her afterwards! Amor vincit omnia, even when dried crusty shite is involved, it seems.

3. "Do You Keep Paint Thinner In Your Closet?"

Some time during college I had these tickets to go a concert featuring three angsty alternative rock bands. The Spin Doctors, Soul Asylum, and The Screaming Trees, I was still listening to cassette tapes back then, so I had all their tapes. I had good seats, too, and I was going with a coworker/friend of mine, Sheila. Sheila was a Keno girl at the hotel I worked at and she was tall with big boobs. We were pretty good friends, and everyone at work thought we were fucking, which basically meant a lot of guys I barely knew at work were suddenly saying hi to me out of some kind of odd guilt, since they all were actively hitting on Sheila while we were "dating." Why weren't we fucking? Because I'm a lame ass, now onto the story at hand. The day of the show, Sheila dinged her Mustang up (she was white trash, too: the father of her little girl was – you guessed it – in prison), and that bummed her out too much to go. She was fruity like that. So I decided to pull the Cheesiest Move Ever, and went with both tickets, figuring to meet a girl there and ply her with my choice seats. And it worked! The show was at the Aladdin Theater for Performing Arts, a great venue back then. Anyway, I arrived early and hung out at the bar outside the entrance to the theater. Eventually I struck up a conversation with this weird chick who wasn't totally hot, but not hideous. She ditched her friends (a girl and her boyfriend, I figured she was a third wheel anyway) and sat with me in the third row, center. Naturally, we ended up at her place that night, and we fucked. But there was one small problem: her pussy reeked. It smelled like fucking turpentine. I was kissing my way down to it, to give it a good licking, then I smelled it somewhere around her navel and bailed out. She rolled me onto my back and started sucking my dick. I figured I would blow a load in her mouth and pre-empt having to even stick my cock inside that pungent horror. So what did she do? Slowly re-orient herself so that the smelly thing was hovering right over my face. Once, when I was a teenager, I fell drunk out of an open car door while the car was moving, my face hovering mere inches above the asphalt. I would have rather moved my head the extra inches into the road whizzing by and had my face sheared off than have had to put my tongue in that snatch, at that moment. But I did! I stuck out my tongue and flapped it around on that noisome box, jamming my nose against her ass cheek to plug my scorched nostrils. Goddammit, can't chicks smell themselves?

2. Unwelcome Bodily Fluids, Part Two

My former job as a hotel bellman had perks beyond those described in my Top Ten Worst Things I've Ever Jacked Off To list. I got to meet a lot of people, including females every blue moon or so. A conversation was struck up between me and these two fairly hot girls as they waited to get into the restaurant that was next to my desk. I pleaded with the manager to comp their food, and I hung out with them on my off time for the rest of their stay. Julie (her real name) and Kim were pals from Hollywood. Julie was/is a starlet whose film credentials are iron-clad: first female to get fully naked and show her ass on NYPD Blue (she was the cheating fiancé of Sipowicz' son), clothing store salesgirl in The Nutty Professor, and most recently, alien girl that Trip gets pregnant by on Enterprise. She's a sweet enough girl, but a little loopy. Kim, though, was more my speed: cerebral, reserved but fun-loving, with a sharp dry wit. We hit it off right away. Anyway, after a second visit by them, I returned the favor by coming out and staying with Kim in Hollywood, in her apartment right off Melrose Avenue.

I met Kim at her job as a bartender in this fairly-upscale L.A. restaurant. Julie showed up a little later with her new beau, this odd but friendly fellow who was apparently a composer, and pretty well-off for it. We partied into the night, including a surreal bit where Kim was going down on me inside a closed outdoor mall. At one point, a crackhead ambled up to me and asked for five dollars. I turned her down. She came back a few minutes later. No ma'am, I still don't have five dollars for you, and I'd rather not ask my date if that's alright. L.A. crackheads are pushy, I tell you.

Sometime later we went back to her apartment. We got naked and into the tub. She read me her poetry, which fortunately didn't suck as hard as she did, ha ha. Then we got into bed and I went down on her. It was great. We had sex and passed out in each other's arms in bed. I would like to state at this point that we were both pretty fucking trashed and riding the wave of a couple of mind-altering substances, both legal and illegal. In the morning, I awoke and went into the bathroom for my morning constitutional. Squinty-eyed and hung over, I chanced a look at myself in the mirror. The image that greeted me was of a dazed psychopath. Apparently Kim had bled a great deal last night, by either menstruation or maybe I had again nicked something, and my face (and crotch, although a lot of that had rubbed off) was caked with dried blood. I didn't recall her flinching in pain (I'm very careful in that regard), so I had to assume it was menstrual. My stomach did a half-gainer as I washed all that crud off my face with some toilet paper. I got back into bed with Kim, and as we both awoke later, I mentioned it. Her sheets were trashed, but she was pretty cool about the whole thing. We both kind of glossed over the fact that I had been slurping up her menstrual discharge for part of the night. At least I didn't notice until the next day.

1. Waking Up To Find My Male Roommate Sucking My Dick

Once, many years ago, I was living with a pal of mine, Bob. We had this two-bedroom apartment with nice freeway access. Anyway, Bob and I became friends while working at that hotel. He was a food server in one of the restaurants, which was situated right next to the bell desk. My ex-girlfriend at the time, Ashley the Redhead, got a job there after I broke up with her so she could stalk me. And she did. She threatened every girl she saw talking to me (oh, this poor little Vietnamese girl – "She said she'd destroy me if we went out!"), and frequently ran up to my desk and shrieked at me for whatever was driving her obsessive paranoid fantasies at the time. "You know what? I don't want a ride from you! Go off by yourself and fuck one of those skanks I know you're fucking!! AAAHH!!" This came a few hours after I offered to give her a ride because her car had broken down. Anyway, she fucked Bob, and then through an odd turn of events we all hung out together for awhile. So Bob and I became better friends over time, bonding (apparently far more than I thought we did) on mushrooms, even. Anyway, a few months after we moved in together, we came home drunk one night (as we often did). I passed out. Then I woke up some time later to find Bob...bobbing. On my cock. It's a little difficult to remember the exact conversation we had, still drunk as I was and traumatized to boot.

"What...what are you doing?"

"What does it look like?" In addition to the sensation of a five o'clock shadow rubbing my nuts, Bob also infused me with his dry wit.

He stopped, and then sat up and offered some kind of rationalization that almost everyone is at least bisexual. Yeah, Bob, but it's a far cry from the occasional homoerotic dream to placing your erect penis into another man's mouth. And might I add that I was doing so wholly unwillingly, you sneaky fag? Anyway, several moments of awkwardness followed, since both of us were naked and my dick was taking too long to detumesce, and his stayed hard. He eventually slumped off to his bedroom, and I lay dazed in my bed until I finally passed out again. We never talked about it. I moved out later, but there were other mitigating factors at work, although I would have used any excuse at that point ("Oops! Hangnail! Got to move out, Bob. Sorry.").

Bill Dungsroman

page 1 2