Top Ten Worst Sexual Experiences

Bill Dungsroman 01/02/2003 

10. The Only Thing I Could Do Then Was Wave My Arms And Say "Ta-Dah!"

Gigi was this bitchy little French girl whom I dated my Sophomore year of college. Slight of build, she had short curly dark hair and white skin. She fancied herself a Feminist, but she was a Feminist in a similar fashion as those Mormon girls you knew in high school who smoked pot, drank like Ozzie Osbourne, and put out more than Madonna on Latino Pride Day were Mormons. Mostly, she just bored the hell out of me during or after every film or television show we watched, as she clumsily tried to discuss the Feminist implications related to the film or show in question. Conversely, she was ridiculously self-conscious about her personal hygiene. Nothing against a girl who doesn't smell (we'll get into that later), but Gigi abhorred sweating, refused to be seen without makeup, and although she gave oral, she never wanted to receive it. She did once, however, but I was not allowed to kiss her on the mouth afterwards. Having a fairly flat chest, I believe she regarded her ass as her best feature, and she preferred doggy-style. Anyway, one night we were going at it doggy-style, on my bed. She had just been going down on me as I sat at the foot of the bed, her on her knees. I just sort of collected myself up to my knees and backed up a little to let her climb onto the bed and orient herself appropriately. Anyway, the result of this rearrangement was that her little hands were dangerously close to the edge of the bed. As I flailed away like a Home Depot manager with his tie caught in the paint shaker, Gigi locked her arms and clutched the bedspread, trying to keep from falling off. Naturally, I had no clue; I was furiously working myself up to orgasm. Finally I came, and as I did, I pushed us forward on the bedspread until Gigi's hands slid off with it. She held on to it, I held on to her, and we tumbled entwined-crotch-over-heels to the floor. Actually, about halfway through the impromptu maneuver my penis slipped out, and I was helpless (being in mid-orgasm as I was) to do anything but roll over her and spray jizz every which way. Ladies and gentlemen, introducing the Clown Acrobats In Hell! I sprained my elbow and nearly got a concussion, but I hid it for fear the whole calamity would somehow queer Gigi against sex with me. Fortunately, she just laughed.

9. I Should Have Realized It Was Only Going To Be Downhill From There

I guess sometimes being average is not so bad: I lost my virginity when I was 17, the national average for males (at the time). I had managed to evolve from screaming spaz into unassuming generic teenager during my Junior year, when I started styling my hair and buying out Chess King for a new wardrobe. I looked like Vanilla Ice's retarded little brother. But I had a full-time job as a busboy in a hotel, and my mom let me drive her new Firebird (God, we were such white trash) while she worked nights. I just needed to find a girl crazy enough to let me fuck her. And I did! Maria was a 21-year-old Mexican girl who worked at same hotel I did. Anyway, I asked her out and she actually said yes. Obviously, this girl was insane. But she was 21! And she had that sultry Latin sexiness, and a nice ass. After about a month of listening to her ramble on about whatfuckingever, I was starting to approach critical mass, since I hadn't had sex with her yet. Yeah yeah, Depeche Mode is great; can I stick my face in your crotch? Anyway, one night we went out and I took her to a nice restaurant. The Z Cavaricci's were extra tight around the ass (thanks to the two belts that held it up), the bolo tie was swinging with authority; I was straight stylin', as we said in my day. Anyway, after eating and getting her to buy us some drinks, we headed to my house I mean, my room. We smuggled the hootch past my brother, who didn't fucking care anyway.

First, some really fucking retarded foreplay. She wanted to try on my pants, the ones I were wearing (just to get them off me, I hoped against hope). I was all of 130 pounds then, so they were only slightly baggy on her. I lounged about in my slate gray dress shirt, unbuttoned with the bolo hanging insouciantly off my desk chair, and my million-year-old white briefs. She had been wearing a dress (which she had since removed), and I gave her a t-shirt to wear as well. Anyway, I told her I wanted to fuck her. How's that for romance, ladies? She giggled, and I then told her I swear I said this that her mouth said no but her eyes said yes. She was so shocked by that unbelievably cheesy-ass line that she rolled her eyes and muttered something in Spanish. Thinking quickly, I pulled up her shirt and started sucking on her titties. Casanova, eat your virginal-blood-stained sheets out. And that was it. It worked!

We clumsily got naked. Well, I clumsily got naked. She'd had who knows how many "boyfriends" by this time, she was a pro. As she slid off my pants and her undies, I stared in awe at her overly-hairy bush. I felt like an explorer from the 1300's gazing upon the Amazon for the first time. A thrilling, exciting, scary new world lay beneath all that wild, dense foliage. I put on a condom from my little box of eight that my mommy had bought me when I turned 16. Ramses, do your stuff. Anyway, I fucked her for quite awhile, and came seven times. We finally had to stop because she was getting sore. As she cleaned up in the bathroom, I jacked off (even then, even then...). I took her home to her weird Mexican family, then went to bed to sleep the blissful sleep of the devirginized.

My phone rang around 3 AM. I answered it, heard nothing, and hung up. The house phone rang, my brother answered it, and told me it was for me. I picked up the phone.


A female voice: "Why did you hang up on me?"

"Oh baby, I'm sorry, I didn't hear anything on the line."

"This is your mother. Are you going to fucking pick me up from work or what?"

Man, that drive over and back was the worst hour of my life. Helpfully adding distraction to the mix was that my mom's boyfriend at the time, a dude in his late twenties who was sponging off her for a place to stay, was sitting on the curb outside a local bar that he'd been thrown out of for being too drunk. Do you know how drunk you have to be to get thrown out of a bar in Las Vegas? Very. Do you know what I did when I got home? Jerked off again. As a postscript, I broke up with Maria a few months later, and learned through people at work that she had to spend some time in a mental hospital for unknown reasons. So I had to lose my virginity to someone who was literally crazy. Yay for me.

8. Then I Gave Her The Irish Whip

Winter of 2001 was a weird time for me. I was living off the remaining school loans I had gotten from medical school, but I had already withdrawn from the program and I hadn't gotten a job yet. My friend Peter was trying his various connections to get me a job as a bartender, or at least a bar back. You see, my utter rejection of medicine was such at the time that I wanted nothing to do with it, even though I was highly trained in that field and that field alone. I just wanted a job that would be fairly short on hassle but big on perks and cash. Thus, bartender. Anyway, we were at a local bar that Peter frequented, and he knew the head bartender. We sat at a corner of the bar and bullshitted with him while he poured us free drinks. The bar was mostly empty except for a gaggle of folks at the other end. They were mostly hazy-faced dudes situated around two girls. One was fat and quiet; the other, her friend, was cute and loud. The cute one was holding court over the local gentry, flitting about and laughing loudly at her own jokes. Peter and I ignored her. At that time in my life, I was overweight and rather depressed, and I wanted nothing to do with some fruity loudmouthed chick teasing all the slobs. Even at my best I never competed well for attention for some girl; I was never good at it to begin with, but I never cared either. Somehow, after awhile she came right up to me and introduced herself, sort of.

"Hi. Can you dodge a hit?" She asked in a manner that was somehow dead between serious and facetious.

"Why, are you going to hit me?" I deftly retorted.

She laughed. "No! I was just talking we were just discussing (she gestured wobbily at the gang) about defending yourself in a fight. How you'd do it?"

"Okay, hit me slowly." She threw a punch and I deflected in some gay manner that I learned from my Kenpo classes, the ones I took back when I entered that phase all young men enter where they must attempt to become ninjas.

"Hey! That was pretty good!' My, was she perky. And cute.

I then explained to her that she should only have to worry about fighting drunk chicks or fighting off drunk guys trying to date rape her. I advised a punch in the nose for the chicks, a knee in the balls for the guys. We discussed combat techniques for awhile, culminating in Ashley her name was Ashley, who knows when she told me instructing me to lay down on the floor while she locked her legs around my head, my face planted firmly in her crotch. I made some vibrator joke and hummed into her crotch. Apparently, that approach went over well with her.

She sat next to me for the rest of the night. We talked about who knows what, John Waters films and shit. Anyway, at some point she asked if I'd like to have my dick sucked. Well, sure. Since the only women in the bar were still just her and her friend, she suggested the Ladies' Room. It was pretty cold outside, so I agreed. Plus, I was plowed.

We went into the Ladies' Room, probably not too discretely. She immediately got on her knees and pulled out my cock, and started sucking on it. I had figured the stall might have been a better choice, but oh well. Anyway, about 5 minutes into it the door opened, and the bartender looked at me.

"Are you doing drugs? Hey, stop that."

"Aawww, Jim." Ashley stood up and walked out, leaving me to tuck my erect penis back into my pants as Jim the Killjoy Bartender observed.

"Go have a seat, stud." I did. I didn't get thrown out, but I sure as Hell didn't get the bar back job. Ashley got more drunk, tried to score coke, failed, and got half-carried out of the bar by her friend as she cried uncontrollably. Vegas chicks, I dunno.

7. Some Things Are More Fun Than A Playstation 2, Kid

Just this past fall of 2002 I briefly dated this nutbag. Man, there's nothing better than swearing up and down to yourself how you're going to keep your shit together, how you're going to stop making dumbass decisions. And then, of course, you go and make one that rivals all of your previous bung-ups. So I did, with Stephanie. Steph was a nice-seeming girl who briefly dated a pal of mine. Said pal has the increasingly-becoming-attractive practice of spending two weeks with a girl. By that two weeks, he either fucks them and ignores them until they leave him alone, or if he can't get any he just proceeds to the ignoring part. Steph, trying to be a decent girl by Vegas standards, rebuffed pal's absurdly forward advances (I've seen it in action, and it does work, on a "special" girl), so he dumped her. But I had to return her coat to her, left as it was in the back seat of my car. And then we dated. I claim insanity at this point. If this part of my life had been rendered in film, it would be the part of the slasher film where the audience starts screaming "Don't go in there!" I went in there.

As it turned out, she just wanted to fuck me once so she could call up my pal and get back at him, like he cared. He cared so much that he told me before I went over to her apartment, "She's got a really nice ass, you have to do her doggy style." Warm and sensitive, that's my pal. Well, she got her requisite fuck from me, since I had nothing to lose except some modicum of pride after the jig was up and she blew me off. And a couple nights out worth of dough from me taking her out. Big deal, I've spent more just to get a piece of my own hand, as it usually turned out.

The sex itself? A wild, weird mix of good and bad. Good: I wasn't expecting it (since I guess she wanted to get it over with ASAP), and she attacked me. If she hadn't been such a bitch to me later (which of course would have negated her forwardness in the first place), this wouldn't have come near this list, in spite of the bad. The bad: her five-year-old son was in the next room (it was a one bedroom apartment, her son had the bedroom, her bedroom was the living room), and we made far too much noise. I had figured on taking her out that night and getting her to my place, where we could swing from the fucking chandeliers if I'd had them. And it would have gone off alright, but for two things. One, her big-ass synthesizer was leaning against the wall next to the bed, and it came crashing down near the end. Son called out "What was that?" Mom answered "Nothing son, now play quietly." Two, after we finished and I put my clothes back on, I noticed that you could see all the way through the fireplace into the bedroom. If son had peeked through, he would have had a clear shot at my swinging balls and his mom's nice ass. I'll just pretend forever that he didn't.

6. "Are You Ever Going To Clean Those Cobwebs?"

During the summer of my Junior year of college I met this girl Crystal in my stupid Poly Sci 101 class. I took Poly Sci in the summer because I harbored an irrational phobia for all things government-related. All that reading and writing and shit, fuck that. Meanwhile, I'd been busily reading textbook after textbook and writing reams of notes and papers in my science classes. I was running off the lingering memories I had of high school government class, mostly. But I had to take Poly Sci as a core requirement, so I bit the bullet and took it all by its lonesome that summer.

I had a girlfriend at the time, Mary, a slight blonde who I'd met in my Genetics class the prior fall. In retrospect, I think maybe I should have married Mary (hence her pseudonym); she was pretty, thin, mostly quiet, and never wanted to talk about serious things like Where Our Relationship Was or Was Going or Why Don't We Talk Anymore or, especially, Why Do I Drink So Goddamned Much. Naturally, at the time, I was a fag who cared about the former two, and she seemed so cold to me at the time. But like a Leprechaun springing gaily out of an outdoor refrigerator in Alaska in the dead of winter, boy was I in for a surprise later in life in terms of feminine coldness. Anyway, we broke up for that summer and I was down for some quick strange. I took the class with a female friend of mine, Hiba (her real name; who knows what real Jordanian names are, I can't even come up with a suitable pseudonym), a really hot little Middle Eastern girl who everyone in the sciences wanted to bag. Forget it, she was a virgin and far too entrenched in her parents' customs and ways, straight from Jordan as they were. The upside was that I figured from the get-go that Hiba was department store window material, so I just made friends with her, since maybe she had hot friends with looser morals (my typical modus operandi for getting girls). As it turned out, that approach served me well for girls that neither of us knew as well. Something along the lines of a girl looking at my "6 out of 10 on his best day" self joking and hanging with some hot friggin' piece of ass, and wondering Are they together? What's his deal? And it worked, just this once, of course when I wasn't expecting or even planning it.

Crystal didn't sit anywhere near me in class, but we nevertheless exchanged smiles and how-are-yas every day. One day we were walking out of class, and we started talking. I clumsily asked her out that weekend, and that was all she wrote. We dated for a few weeks, and for the most part it was fine, but for two things. One, she never took her shirt off in front of me. Not during sex, never. She would push my hands away whenever I went up under her shirt to undo her bra. I was preparing to broach this subject with her, initially thinking that she just had small boobs and was self-conscious about them. I'm not a boob guy, really, so I didn't care. But then I started freaking out, thinking that maybe she was disfigured or something. Maybe one of her tits had been lopped off in some freak Home Ec accident in high school, or maybe they looked like golf balls dangling inside a condom. Who knows? Fine, keep your shirt on, you freak. But the last straw (even though it was only the second straw, technically; hey, this was college) came during the last time we had sex. We were going at it in my bedroom, not for very long, when she made that fussy bitchy girl-sigh and said:

"Are you done yet?"


Listen, the last thing I'll ever be accused of sexually is taking too long. Even so, this was not one of those situations that might predicate such thing; I wasn't drunk, stoned, whatever, and we had only been having actual intercourse for about 5 or 10 minutes. Am I done yet? Yeah, I'm done honey, but for me the afterglow involves me continuing to flail away on you with a raging hard-on like I have been for the past couple minutes. I'm glad you asked.

Actually, I did answer her. I said yes, stopped, and vowed to never fuck that girl again. I'm done, alright, done forever. I broke up with her a few days later, citing some nonexistent reason. She accused me of dumping her for Hiba (oh, only if), when in reality I went back to Mary for a couple of months. Mary was polite enough to be quiet and let me finish, at least.

page 1 2