My First Ass Fuck

I remember when I saw my own cum for the first time. I was in middle school and ignorant, especially since I’d never seen it before. Before Penthouse Letters, I began masturbating in the fifth grade to imaginary images of looking up a girl’s skirt. Whomever I had a crush on at the time would wind up as my jerk-victim. When I first started to cum in seventh grade, I thought something was wrong with my dick, and I should have been aiming my jizz in a sink or container since everything that ever came out of my penis had always gone into a toilet. I quickly discovered appropriate cum dispensers–tissues or printer paper–once I realized masturbation was there to stay, and when I realized how good the feeling of these newfound wet orgasms felt.

I remember other momentous sexual moments. I thought it was so cool feeling those little sacs of fat when I got my hands on a real set of boobs. I squeezed and squeezed until they became red. I remember the girl lying on her back, looking at me curiously, and smiling.

My first kiss was in the seventh grade while playing in a game of truth or dare. I was dared to kiss this cute eighth-grade chick–a girl who would soon enter my up-the-skirt masturbating mind. I hesitated and licked my lips before planting the kiss. Afterwards, she made a face and proclaimed to all twelve participants, “There was like, spit in there.”

When I fingered a pussy for the first time, I smelled my fingers for over two hours thinking I was “the man,” despite the fact that in retrospect, that particular pussy was probably in the bottom 4% of all pussy fragrances.

I remember getting my first blowjob, blissfully sitting on a couch thinking to myself, “Damn…oh fuck…whoa!”

I first had sex in the passenger seat of my car, the two of us awkwardly trying to find a comfortable position. I couldn’t develop any rhythm or ascent and remember thinking to myself, “This is sex? What a waste.”

The first time I had anal sex happened on a Friday night.

Etienne had the big table reserved at Sutra, and about ten of us headed out to mooch off his hook-ups. We were poised for an adventure, and there were even a few celebrities present: Matt Leinart, Dennis Rodman, and a chick named “Alex” from the MTV reality show Laguna Beach.

There was bottle service at the table, but I refused and bought my own beer. Drinking mixed drinks would often cause me to lose control of my fadedness, often resulting in an unfortunate behemoth hook-up or even worse, loss of memory. I am at least able to maintain control along with my memory when I drink beer. I walked back to the bar to buy another cold one.

When I returned to the table, I noticed a blonde gothic-looking chick talking with my buddy E.J. She wasn’t hot, but her black eye-makeup and lipstick sparked my curiosity. I kept my eye on her. E.J. was at the club with his girlfriend; when he saw me looking at goth chick, he left her at the post and went to the bathroom. “She’s all yours, bro,” he said as he strolled past. I walked up to her immediately.

“I like your eye shadow.”

She looked at me for two seconds, got within six inches of my face, and began to speak as if she’d just downed a six-pack of Red Bull. “What’s your favorite sexual position?”

“Uh, doggie-style.”

“Mine’s anal.”
I smiled and chuckled for a moment. “Oh, we are definitely partying tonight.”

What in the world? I had said FIVE words, and this chick just implied to me that she wanted to get ass-fucked. We talked some more about sex. In fact, we embarked on an in-depth discussion on why anal sex is so advantageous and underrated. I had never fired my dick into a butt-hole before, but I lied and told her, “I used to date this girl who was all about it. She loved it.” She listened attentively, just bathing in my artificial juicy experience.

I continued to smile and talk about how cool I thought her make-up and black clothes were. After a half hour of feeding her this shit, we took off.

Maybe someone had slipped something in my beer, but what happened in the next twenty minutes remains a mystery to this day. The next thing I remember, we were standing next to a fire hydrant near a liquor store two miles down the road. I had no car. She had no car. There are a few possible scenarios of how we mysteriously arrived at that location:

1)  We took a cab (But I would have remembered that and why wasn’t the cab next to the fire hydrant with us?).

2)  We had taken a pitstop for water on our 18-mile walk home (No).

3)  A guy with a rickshaw from India was visiting California and was looking to make a few extra bucks. In our drunken haze, we thought it would be adventurous.

Whatever had happened, at least we were both safe. In that moment of re-awakening, my roommate KG called my cell phone and asked me, “What the fuck happened to you?” My reply sounded something like this:

“Uh…I’m uh…dude, I’m at the store. I’m faded, it’s a liquor store, we’re standing next to a fire hydrant down the street.”

After several more questions from him, he figured out where we were and drove by with his girlfriend to pick us up.

KG and his girl were both laughing at us. “How the fuck did you end up here?” they asked. Tracy (goth girl) and I looked at each other, laughed, and could not come up with an answer. “We wanted more beer,” I volunteered.

Tracy began to ask KG’s girlfriend Sally what kind of sexual positions she liked. Sally had never tried anal and wasn’t too open to talk about it. Lacking tact, Tracy kept pushing the issue, eventually ending it with “I think every girl should try anal at least once. There is sooo much more sensation down there. Oh my gawd!” Sally remained silent while I quietly laughed: it was hilarious, and I agreed with Tracy. I was going home with a winner. Even better, she wanted my dick up her ass.

Prior to this night, I’d had two opportunities at anal sex. Both opportunities had ended in disappointment. Either I just couldn’t get my dick in there, or the lube was inadequate. Or both. In fact, both girls halted my attempt with a sentence beginning with the three words “Actually, I don’t..” It just wasn’t meant to be. But tonight, things were different. I hoped.

When we arrived home, Tracy and I sprinted upstairs, slammed the door, ripped each other’s clothes off, and she started sucking my dick. Blowjobs were old news. I wanted butt-hole.

She asked if I had lube. In my bathroom, I scrounged through the cabinets in a horny frenzy. I had nothing. Although I had seen K-Y jelly at the supermarket here and there, I never had the balls to buy it for nights like this because I was secretly worried about what the store clerk would think of me. My lameness was about to cost me butt sex. Luckily, my other roommate had some after-shave gel. It was the best I could do.

I didn’t want Tracy to see my failed attempt at finding an adequate lube. When she tried to get a look at the borderline lubricant I had brought back, I turned her around quickly, turned off the lights, bent her over, put the condom on, and squeezed the after-shave gel all over her ass and my dick, just the way pornstars did it. At least I had fooled her. Now I just had to get my dick in there.

My dick went in easier than I thought. Her asshole muscles were weak, and a minute later she was screaming (in pleasure I hoped). The after-shave gel had worked. I was officially a member of the Ass-fuck Club.

About seven minutes into the plowing, she asked if I wanted to take a shower with her. No girl had ever asked me to take a shower with her mid-fuck, but I said okay anyway. I was ass-fucking her missionary at the time, and when I pulled out, I heard a slow rumbling farting noise. It wasn’t loud or ominous. It was kind of like hearing a motorcycle four blocks away slowly coming to a stop. I figured it was just my dick coming out of the now vacuous poop-chute that had caused it. But the smell. Oh the smell. It didn’t smell like a fart. It smelled like real-life poop. I gave her the benefit of the doubt, however, and we got up headed to the bathroom.

She got in first and turned on the shower immediately. When I got in, the water on the shower floor was a shade of light brown. Light brown! She tried to divert my attention by grabbing my dick, and almost succeeded, but I know what I saw. I squirted some shampoo on both our heads to take my mind off that color.

The shower water returned to normal; we finished up and dried off. She blew me in the shower to get me excited again. For some reason, I was starting to think she had ulterior motives or at least “a plan,” but she distracted me. When we got back into my room, she demanded, “Fuck my ass, NOW.” I obeyed. We finished up and passed out.

The next morning, we both felt triumphant. She had gotten a much-needed anal fuck (She said it had been a while and that she “needed that”), and I became a member of the ass-fuck club.

When she went to the bathroom, I got on my computer. As I was clicking from the fantasy sports page, to MySpace, to email, I briefly glanced at my bed. Almost exactly in the middle was a dark shade about the diameter of a softball. Dreading what I’d find, I moved in to get a closer look. It was poop. Tracy’s poop. It wasn’t a log, just a half-dried puddle with some definite texture. That motorcycle fart had been much more substantial than I had originally thought. Tracy had left a patty in my bed, and we had slept in it.

I checked my body: no brown marks. But I didn’t trust my eyes. All her “moves” with the shower, sudden dick grabs, and sudden blowjobs, instantly hit me. What a mess.

When she came out of the bathroom, I told her we had “better get moving.” I drove her back to her car and could not get the brown softball image out of my mind. I contemplated telling her about the present she’d left on my bed, but refrained in the end because talking about it would have just made me feel worse. This incident was something I needed to keep bottled up. She tried to ask me about being a teacher and other small talk, but I just remained passive and sped down the highway for eighteen miles. When I dropped her off, I told her I’d call her. “Okay, yeah call me. Next time I’ll prepare myself for you,” she replied. I didn’t call her. I think she knew about the shit stains all along. She’d prepare herself? I assumed she was talking about an enema or something to wash the shit out. Yuck. Porn stars have it rough.

When I got back home, I felt like a guilt-burdened murderer returning to his mutilated victim. The patty was waiting for me. In disgust, I ferociously ripped my sheets off my bed. EVERYTHING. I took a shower, tossed the sheets in my car, drove down the street, and then threw the sheets in the neighborhood dumpster. I considered tossing out the mattress but didn’t find any residue, so I just sprayed some 409 in the softball vicinity and gave it a second chance.

Yes, I am in the Ass-fuck Club, but I have my scars. I can still smell the motorcycle “fart,” and I can still picture the aftermath of my bed. Brown is a horrible color.

 

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