Who said online dating was a bad idea? All I knew was, I didn’t end up dead in a ditch and my skin wasn’t cured for a lampshade. In fact, Joe was the best boyfriend I had up until that point. Or my first, either way. Prior to him, I was just a warm hole to stick it in. Guys loved to fuck me, but didn’t think I was worth the trouble of a real relationship.

So breaking up with Joe was a tough decision. He was 12 years my senior and the novelty was wearing off big time. At first it was a refreshing change of pace to the selfish, insecure, and indecisive guys I had been seeing that were my age. Joe was so perfect. On paper. Third year law school, laughed at my jokes, loved ethnic food, chivalrous, sexually generous. What’s not to like? What’s not to like is when someone (me) just hits the drinking age and wanted to drink and fuck all the time; a man like Joe didn’t exactly fit in that kind of lifestyle. Things were getting stale, so I broke up with him on a Wednesday.

By Friday I needed to go out and get laid. I needed to know I still had it; that I could charm the pants off of anyone I chose. And so we headed over to a very, very Irish bar. The only brownie at the joint, and I actually felt more at home than I was comfortable with. Half the night’s complete and I saw an attractive black man walk by. Finally! I mentally preped myself to approach him, when his even more attractive Irish Catholic friend followed. I changed targets and braced myself for the Catholic guilt I knew I was going to face in the morning. I tried to play the game a little and show off a bit to see if he’d come over to me. He kept looking over, he kept checking me out, but he never approached me. Some time passed and I rolled my eyes because I already had a feeling I had to do all the work. I approached him and told him he looked bored. Caught off guard, he said he was. His name is Dan. Small talk ensued and I wasn’t terribly impressed, but he’d do. Physically, he’s out of my league. Intellectually, I’m out of his.

It’s last call and all of the sudden the Catholic guilt from Joe caught up. I decided maybe I wasn’t thoroughly ready for this, so I left the ball in Dan’s court and told him to call me the next day. If I knew anything about guys, I knew he wouldn’t call until he wanted to (if he wanted to at all). This gave me a few days to wash Joe’s guilt off me. I’ll dip myself in bleach if I have to.

Surprise, surprise, Dan called me the next day ready to take me out. I was finally impressed. I dolled myself up and shaved everything I had to. He wanted to meet in Wrigleyville, ofcourse. I knew he was a meat-head from the beginning and I knew kind-of-sort-of what I was getting into. We bar hopped and bar hopped and bar hopped, yet he’d only bought me one drink so far. And every bar we went to, he spent more time talking to the bouncer than he did me. I ruled out him being gay because of how cheap he was. He was networking with the bouncers on our fucking date. He was networking so the bouncers wouldn’t charge him cover next time he came in. I guess I can’t blame him for being a multi-tasker.

So let’s get to the meat of the story. This is where the story really begins. He asked me back to his apartment to ‘check out his roof deck.’ Whatever, dude. I don’t understand why he has to sugar coat his intentions when he didn’t show a slight hint of interest beyond sex. When he didn’t even show enough decency to fake a conversation throughout our ‘date.’ He showed me his roof deck, and I was bored. When we entered is apartment, I was surprised to find the place absolutely immaculate. Everything, to the magnets on his fridge, placed so intentionally. He just moved from Michigan, he started saying, so his place is very bare bones. I don’t care.

We started making out, and I was bored. We made out for a good long time before I realized the situation hadn’t progressed at all. No clothes were taken off, no under-the-shirt groping, nothing. I rolled my eyes again knowing I had to do all the work. I’m annoyed that this was already foreshadowed from the night before.

I pushed him down on the rust colored velour couch and decided to progress things myself. A straddled him as the light from the TV reflected off of his alabaster skin; his expression pathetically aroused. His mouth parted slightly, his eyebrows raised and contracted as I went a bit further down to undo his jeans. He exhaled as his jeans moved past his ankles. Sliding the waistband of his boxers down, licking the red ridges his boxers left on the skin of his hip, I realized this was the biggest waste of time.

His penis, in all its glory, was nothing larger than the length of a fist and a head. To make sure I wasn’t hallucinating – maybe I was drunker than I thought? – I measured one more time. I wrapped my fist around his shaft, and nothing is left but his head, barely peaking out above my index finger. Maybe I’m wrong. Maybe I’ll use a different measuring tool. I wrapped my lips around the base of his dick and I couldn’t even feel the head near my throat. It only reached the roof of my mouth. Like a popsicle, I pressed my tongue on the bottom of his penis and slowly moved my head up to make eye contact. His dick slid out of my mouth and I looked up to see him watching TV. Reaching for the remote.

Oh. Hell. No! All that work for this? I decided I’m done trying to make any kind of lasting impression on this guy. He spent the entirety of our date networking, and now he thinks he can get away with acting like a meathead while his dick’s getting sucked. I got up and looked at the clock. Half an hour had passed since we started making out and my clothes are still on. Annoyed, I said, ‘you got a condom or what?’

I followed him into his bedroom where everything was precisely placed like a hotel room that hadn’t been renovated since the early 90’s. On his nightstand given to him by his dead grandmother were 4 condoms, fanned out in the shape of a rainbow. Breaking the arch, he grabbed a condom and fumbled to put it on himself. Do I have to do everything here? I’m just gonna get mine and get the fuck out of here. I grabbed it out of his hand, ripped it open, put it on, pushed him down on the bed, and sat right down. If he didn’t want to do work then I’d just have to do this however I wanted. I pushed down on his chest with both hands for leverage, raised and lowered my hips, my hair chandeliered down on his face. I closed my eyes and thought about girls kissing. I closed my eyes and thought about girls kissing on some guy’s dick. I closed my eyes and thought of an orgy with hands and torsos and pink and wet. I closed my eyes and thought about anything and everything so I could climax as quickly as possible and leave.

I was almost there and I realized I had to pee. I’m not used to climaxing vaginally and got too scared that I’d piss all over this guy – even though he probably deserved it. I hopped off and told him to, ‘hold this,’ and handed him his dick. I peed and wiped everything dry, realizing that I had to start all over again to get anywhere near aroused.

I walked back to the bedroom and am surprised to see him standing next to the bed, left hand holding his dick, right hand pointing to the bed as if to tell me, ‘get on your fours.’ I’m ecstatic. Finally! Some fun! I get on the bed like a horny little puppy and pushed my ass towards him, making a rhombus shape. I was so excited that he finally found some initiative, that I didn’t realize he didn’t ‘prep’ me for insertion. As dry as I was down there, he still tried to put his little prick into my vagina. He kept pressing and barely got his head through. He didn’t try to spit on his dick or on me, and he still pressed through mid-shaft. He didn’t try to separate my lips with his fingers, and he finally pressed his entire 4 inches in. Was this his first time? Once he got in there, he worked it like a jackhammer. I never thought I’d use such a cliché expression to describe the act of sex, but he had absolutely no technique. He just pointed in a direction and went to town.

I’m not a woman who enjoys spreading private information to anyone who will listen. The intimacy of sexual pleasure is one of the most excellent human experiences that cannot be equated with anything else. Wars are fought for it, people devote their lives to it, whole groups of people spend centuries denying themselves from it. Beyond hunger and sleep, some could say sex drives us to act. So to release this kind of information, on this specific person, is not without reason. As I’ve mentioned before, the size of his dick has been a problem all night.

So to justifiably release this information, those seemingly harmless 4 inches almost ended me. He was going to town, jackhammer and all, and he kept slipping out. This went on for awhile.  A lot of jackhammering and a lot of slipping out of me. At one point, he grew tired of manually reinserting, so once he slipped out, he tried to reenter through sheer momentum.    BAD.    I. DE. A.     When he pulled out, instead of reinserting into the now well-lubricated hole, his dick ‘accidentally’ moved up a few measures. Up a few measures into my very tight and unassuming brown eye.

Time, motion, sound, they all stopped. I heard a pop, and everything went into slow motion. The motherfucker popped my ass cherry. My head automatically pulled up as I let out a scream, as my elbows met behind my back, hands up in surrender. My arms flailed around like dolphin fins and I couldn’t think of what to do next. Time, motion, sound, they all came rushing back and I jumped up. I jumped up and grabbed my ass like I was going to vomit shit out of it. I looked around frantically and only saw white. White carpet, white duvet, white walls. And I thought I was going to shit all over them. Still holding my ass shut, I ran to the bathroom knowing that I was, but hoping that I wasn’t, bleeding out of my ass.

I ran into the bathroom, slammed the door shut, and took a seat. Sure enough, I swiped a bright red stain on the toilet paper. Is this coming from my own body?? I felt faint. In fact, I started fainting. I don’t remember drinking this much – to the point where I would start passing out… I need some water. I looked over to the sink on my right and started getting up. A one foot distance never seemed so far away. I got up from the toilet, and woke up a second later on the floor.  Why am I on the floor? Where’s that sink? I grabbed the sink with my right hand. Braced myself with my other hand. I managed to pull my head above the sink, only to pass out again and slammed my chin on the porcelain. Bit my tongue. Pulled myself up finally and tried to look at myself in the mirror to see if I’d possibly been drugged. Before I can even look into my eyes, I slipped out of consciousness one more time and nailed the mirror with my forehead. By this time, ol’ small dick is knocking on the door asking if I’m ok in there. I grunted and passed out one more time right after I managed to turn the sink on.

The second I heard the water run, I snapped out of it. All of the sudden, I was sober and wide eyed and wondering why the hell I had slipped in and out of consciousness. I scooped as much water into my mouth as I could and tasted iron. My tongue was bleeding and my lip busted open, on top of the bruises on my chin, forehead, and god knows where else. I was loosing way too much blood for not having my period this week. I splashed some water on my face and braced myself before leaving the bathroom.

I walked out and he asked what happened. As if he didn’t know. You popped me in the ass, dude. He showed concern right after he tried to hide his laughter. Of course this was funny. How could it not be? I’m exhausted and I don’t want to be touched, but it was too late to go home. I crawled into his bed and told him I was going to sleep, terrified that I was going to wake up in a pool of my own blood. I checked the clock. 5 am.

8 am and I was tossing and turning, making sure the sheets were dry and not soaked with ass blood. He woke up and tried to start things where we left them last night. Touching me, I turned away from his kisses. How the fuck does he think this is ok? I told him I was not comfortable. He said not to worry, to trust him. I can’t fucking do this. As he was dry humping me and as I was thinking of any and every excuse not to finish the job, I felt something warm and wet. No way. He just came. He abruptly stopped, hesitated, then said he needed to use the wash room. I quickly got out of bed and started putting my clothes on hoping I could escape before he got out. No such luck.

He walked back into the room and started making the bed. He gave the covers a once over with his hand, checking to see if any man juice spilled on to his duvet. Did he think that I didn’t see or feel that?! Fucking idiot. I was just glad to NOT see red stains on his sheets.

I rushed to get my clothes on and get the fuck out of there. His demeanor was distant since he came, but I couldn’t give two shits at that point. We awkwardly said goodbye without saying that we had a good time or we’d call. Who needs to lie at this point?

I couldn’t get out of there any faster. I thought I was home free when I finally see some sunlight and a sidewalk, only to quickly realize I didn’t remember exactly where the train station was. Chicago living made me arrogant enough to think I could get by knowing the general direction of where I was headed, but I was soon humbled. The thing about the Sheridan train stop on the Red Line was that it took an S shape on the tracks. So I followed the tracks, but couldn’t seem to find the actual station. This took me over a half hour of walking too far north, back tracking, walking too far south, only to come back around again. All the while I walked around in a tube top with nipples you could use as a kebab stick, and a skirt too short for a Sunday morning before church. My hair looked like a bird’s nest, my mascara was  smeared, and I was walking around with Gumbie’s posture. EVERYONE was looking at me like, ‘this girl either had a really good or a really terrible time last night.’ All with a little smirk on their face.

Once a few hesitant locals finally pointed me to the direction of the station, I sat on the train with a sense of relief. But it hurts to sit. In fact, it hurt to do nearly everything. Coughing, laughing, raising my eyebrow, and I could feel all of this in my ass. I never realized how much of my ass muscles I used with my face. Five stops on the El took what seemed five years. All the while, every few minutes I’d think of the night’s events and start laughing to myself. Unable to bend my knees because the movement hurt my ass too much, the walk back to the apartment was the River Styx. Oh my God, and the three flights of stairs!! The stairs were so painful that I ended up blocking it out of my memory as a survival tactic. Once I pushed through the heavy wooden door, I had to make the decision of either walking 100 feet to the couch or the 120 feet to my comfortable bed. The couch obviously won. As I lay myself down on my stomach, my face peeking out from the side of the sofa, I started chuckling to myself thinking only this kind of shit ever happens to me.