“I think you must’ve busted something inside of me, ‘cause I’m bleeding,” Holy God, I thought. Is she kidding me? After all that, is she really still pretending? The futile, embarrassing attempt at sex we’d just colluded in, the even more humiliating confession that followed, and still she’s trying to play her part? Prop up my ego? Convince me that my half-hard and fully white dick was just too much for any mortal woman to handle? On top of all the other thoughts and feelings swimming through my brain at that moment, all the shame and disappointment and wretched self-loathing, I was insulted she’d think I was that fucking stupid. When someone sees you at your absolute lowest, when all your usual defense mechanisms have been stripped away and you’re splayed out naked and bleeding where somebody else can see it, you like to think there might be some level of mutual understanding between you and them. A sense of shared hardship, perhaps, a bond borne of the fact that we’ve all been in that place at one time or another. But no. She was still trying to convince me that my totem-pole cock could take lives if I wasn’t careful. I suppose I was foolish to expect anything else, considering the circumstances. After all, she was technically still on the clock for another ten minutes.

It had been a tough year. My girlfriend had left me a month after my twentieth birthday for reasons too complex to go into ( read: I fucked up and she didn’t like me enough to give me a second chance). We had been together three years. She was the first girl who’d ever paid attention to me who hadn’t been fat, retarded, or a combination of the two. 

I took the breakup harder than I could’ve ever anticipated. Every morning when I woke up, before even opening my eyes, I was thinking of her. If I could keep myself from dwelling on how miserable, alone, worthless and heart-broken I was for at least one hour in any given day, I considered it a triumph. At night, when I was sure my house mates were asleep, I’d stay up listening to the most overwrought and sappy breakup songs I could find, making a game out of trying to stifle my tears. The constant temptation to call her, hear her voice, that she missed me, that she still loved me, was almost maddening. The fact that she had wasted no time in finding a new boyfriend just compounded matters that much more. 

My own efforts at dating were going nowhere near so smoothly. Where I’d once been able talk freely with any girl I saw, secure in the knowledge there was nothing I wanted from them, now it was a struggle just to form simple sentences. My attempts to approach the girls I shared classes with were awkward, stumbling stutter-fests or lame suggestions that we “should get together and study sometime.” 

I noticed a girl I had section with seemed to go out of her way to talk to me, so I told her we should hang out and get food. During the half-hour of avoiding eye contact that constituted our “date” I managed to impart the following pieces of information:

A)  I had only recently gotten out of a serious long-term relationship.

B)  My girlfriend had left me because, among other reasons, I was hyper-controlling, moody, self-absorbed, egotistical, insensitive and verbally abusive. I assured the girl that this was alright, however, because I had grown a lot and would never do any of this again.

C)  She wasn’t as good-looking as my ex had been, but this was also alright because I didn’t hold it against her.

We did not have a second date.

When Summer arrived the continual sob session that my life had become got even worse. None of my friends from home knew any single girls. I wasn’t old enough to go to bars. I didn’t have any female friends or acquaintances. Put simply, the closest my dick could come to touching pussy would have been to sneak into a ladies’ room and rub it on a toilet seat. 

Involuntary celibacy only made my obsession with finding a girl, any girl to fuck, increase exponentially as time went on. I spent agonizing hours imagining how uninhibited and wild my ex must be with her new boyfriend, moaning like a porn star and cumming like a crazed tantra addict, our own sex life almost certainly a dull and distant memory. It killed me to know that she had no reason to fear what I might be up to. 

Eventually, obsession and desperation combined and I came to a decision: I had to get this girl off my mind and I couldn’t do it until I fucked someone else. It didn’t matter how, it wasn’t like my self-esteem could get any lower than it already was. I had just won $130 off my father gambling on ping-pong games. I had no doubt that this was the best possible use for the money. 

A half hour of perusing Craigslist ads and I believed I’d found a viable candidate. My primary concerns were looks and price, hoping that I could get a girl who was at least mildly attractive in spite of my limited cash flow. After browsing a few ads that didn’t meet my minimum standard (thin, full head of teeth, born a female) I found one that caught my fancy. Destiny, a skinny, well-endowed white girl with a mousey, pinched face and dyed blonde hair, promised that she would “talk to you in my sexy southern accent while you fuck me hard.” Something about this offer seemed enticing to me.

It took me days to summon up the courage to dial the number from the ad. Pacing back and forth across my room, phone in hand, palms sweating, dialing and hanging up, dialing and hanging up. Eventually I sat down. Took a breath. Just jump in and get this over with. I dialed. The girl answered on the second ring. “Hello?” She didn’t sound southern so far.

“Uh, Hi. I… I saw your ad on Craigslist.”

“So you want a date?”

“Yeah, that would be…that would be nice. The thing is, I kind of have a problem. I mean you uh, you can’t come here.”

“What’s he sayin”? A male voice came in from the background.

“He says we can’t go there.”

“Well he ain’t comin’ here.” They began to discuss options in muffled voices. I couldn’t make out most of the words. That’s alright, guys. You just work this out between yourselves. I’m not even here. 

“Hey, you still there?” Awesome! She hasn’t forgotten me.

“Yeah.”

“I’ll meet you at a motel.”

“Uh….cool.” She gave me an address and said to be there in an hour. The place was a few miles away and I wasn’t too familiar with the buses in the area, so after making sure I had the cash, my phone, and no forms of identification on me, I started walking. 

Almost immediately after setting foot out the door, I started imagining all of the possible ways in which this could go wrong and all the awful things that might happen to me. What if they were looking for an opportune moment to get me alone and then rob me at knife point? What if this was an elaborate police sting and a S.W.A.T. team burst into the motel as soon as money exchanged hands ready to haul me out, hands cuffed behind me, before a mass assembly of local media? I could clearly visualize the flash of the cameras, the chubby, bearded men jotting notes on clipboards, the semi-attractive women in grey business ensembles shoving mics in my face and berating me with questions. Is this your first time buying pussy? How does it make you feel to have to pay for it? Have you always been a sleazy perv, or just since that bitch left you all alone and hating your life? What if the girl looked nothing like her picture? Would I still have to go through with it if she was morbidly obese with dragons breathing fire tattooed on her tits? 

I checked the time. I was supposed to meet them in ten minutes. I was still a good thirty blocks away. I hoped they wouldn’t be angry over my lateness.

Not two minutes after I’d missed our appointed time, my phone rang. “Hello?”

“This Mike?” It was the guy I’d heard before. I hadn’t given them given them my real name, of course.

“Yeah.”

“Where are you?”

“I should be there in about twenty minutes. Sorry I’m a little late.”

“Don’t worry about it, we’ll come pick you up.” I told him roughly where I was and kept walking. A few minutes later a car pulled up alongside me. A blonde with a pinched face leaned out the passenger window. 

“Mike?”

“Yeah.”

“Get in, we’ll drive there together.”

“OK.” Her accent was southern only in the sense that L.A. is at the southern end of California.

I climbed in the back. Her pimp was driving. He was a beefy white guy with a backwards baseball cap and a barbed wire tattoo on his right arm, a neatly trimmed goatee adorning his meaty face. He looked like the type of guy who would be equally at home at a monster truck rally, a frat party or a minimum security prison. He introduced himself as Brad and shook my hand, an easy smile on his face. “You, uh, you aren’t a cop, are you?” He laughed.

“No, man, I ain’t no cop.” He paused a second. “That doesn’t work, though. They don’t have to tell you even if you ask.”

“Oh…I didn’t know that.” We didn’t talk for the rest of the five minute drive. I relaxed slightly, deciding that since no one had pulled a knife, a badge, or asked me to bend over and lube up yet, I could cross those off my list of potential catastrophes. 

We pulled into the motel parking lot. When Destiny stepped out of the car I got my first decent look at her. By most standards, she’d be considered attractive, maybe even hot. Stick legs leading up to a small but still curvy ass, perky C-cup breasts jutting out far enough to cast a shadow over her flat stomach. Had she passed me on the street, I almost certainly would have turned my head, pictured her naked, thought about fucking her. I didn’t have to think now. I was going to fuck her. I had to keep reminding myself of that. “Ain’t she gorgeous, man?” I guess Brad must have noticed me looking.

“Yeah. She’s….she’s really something.”

“Oh shit!” She tripped on the curb as she was walking towards the front desk office. I hoped she’d have better coordination in bed. “Sorry for cursing, it’s not very ladylike,” she said with a giggle. I was far too nervous to point out the irony in that statement. 

Rooms were 120$. They told me to pay for the room and then hand over the extra five. It seemed strange to me that they’d take a deal that only left them with five bucks to spend, but there was no way I was asking unnecessary questions.

I got us the room and the three of us walked in. I was beginning to get very uneasy about the fact that Brad, charming fellow though he was, had not left yet. I wasn’t expert on these matters, but I was pretty sure we’d reached the point where his presence was no longer required. I mean, seriously, was he planning to fucking watch? 

“I’ll be right back,” Destiny said as she walked into the bathroom, no doubt to do whatever it is hookers do directly prior to inviting strange men inside their vaginas. 

“So here’s the thing, bro. This is her first time and she’s kinda nervous so I’m just gonna be chillin’ in the  bathroom while you get to it. You OK with that?” Fuck no. Are you kidding me? Of course I’m not OK with that.

“Yeah, sure. I mean I understand and all. It’s OK.” My fear of being beaten and robbed had somehow deleted the word “no” from my vocabulary. 

“Cool,” he produced a small, see-through pink nightie from the pocket of his faded jeans and flashed it at me with a knowing smile. “She’ll be out in a minute, just gonna get her all sexy for you.” He switched off the room light and went to join her in the bathroom. 

I took off my jacket and sat on the bed. I could remember the moment when I first drummed up the courage to kiss my ex. I could remember when we first had sex. I had thought those experiences were high in pressure. But nothing I’d done in my life up to that point compared to the pressure of having to fuck a hooker while her pimp boyfriend was sitting ten feet away in a motel bathroom. I clutched the bedspread and began to think this had been a very bad idea.

She came out of the bathroom wearing nothing but the nightie Brad had shown me and a pink thong. I stood up and took off my clothes wordlessly. I asked if we were allowed to kiss. She said no. We moved onto the bed. I reached under the nightie and squeezed her breasts. They felt a bit rubbery, though she’d claimed they were natural. My dick didn’t seem to be responding. I took off the nightie and sucked her tits. I pushed my hand inside her panties and tried to finger her. She was completely dry. 

I decided to give up on the foreplay. I had managed to get a semi, if I could just get it inside her before losing it I was certain I’d get hard. I put on a condom and climbed on top of her. After a bit of fumbling, I managed to get it in. She was lying rigid beneath me, so tense she was almost holding her breath. I started thrusting. She started gasping, but more out of fear, it seemed, than pleasure. She was as nervous as I was. My dick wasn’t getting any harder. I started to panic.

“Can we try doing it doggystyle?”

“No,” she said, her teeth clenched.

“Oh…OK.” Excuse me? Jesus, what the fuck am I even paying for? I kept thrusting. Whatever the opposite of sensation is, that is what my dick was feeling. It was like the nerve fibers in my penis were on strike, like I was moving it back and forth through an empty void. I would’ve been bored if I weren’t so desperate. If I couldn’t get off then this whole ordeal was for nothing.

“I’m sorry, we can do it that way if you want.” I pulled out to let her get on all fours. I was so soft by this point that I was barely able to get my dick back inside her. It was like trying to play pool with a length of rope.

I tried everything I could think of. I varied my thrusting speed. I closed my eyes and thought of my ex. I thought of my ex’s best friend. I thought of the Asian girl with skin-tight short-shorts I’d seen in the gym. I thought of how hot it was (or should have been) to be banging a hooker who looked like a cheerleader in a cheap motel room. I thought of Michelle fucking Pfeiffer. Nothing worked. Nothing could stop the inevitable flow of blood from my dick back into my body. 

Wanting to at least spare myself the embarrassment of going completely soft and falling out of her, I pulled out. She tried, briefly, to coax me to life with her mouth, but it was no use. 

Finally, even though I still had ten minutes left, I threw the condom in the trash and lay back on the bed, disgusted with myself. It had been a night of firsts. First time with a hooker. First time with a pimp sitting in the bathroom ten feet away. First time I couldn’t get hard. 

As I lay there willing the minutes to pass, willing myself out of that room, willing this horrible night to be over, I started talking. I told her about my ex and how desperate I was to get the whole thing off my mind. I told her I had just been incredibly nervous and she’d done nothing wrong. She seemed sympathetic. “That’s why so many guys are assholes, because some girl screws them over early on and then they go around screwing over girls. It sucks.” After a few more words of encouragement, she excused herself to the bathroom. Somewhere in the back of my mind I realized that, on top of everything else, I had just gotten sympathy and relationship advice FROM A HOOKER. Honestly, is there a way to sink any fucking lower? Unfortunately, there was.

I was already dressed when she came back and told me she was bleeding. I shrugged it off, all I wanted was to get out of there and no fairy tales about my giant prick were gonna make me feel better. I just wanted to take a piss, leave that awful room, and try and forget any of this ever happened (not that I ever could). 

Brad emerged from the bathroom shortly after her. “Hey, it’s cool, man, I’ve had old lady troubles too.” Thanks dude! Destiny’s pep talk helped but now that I know you and I have gone through the same shit, I think all my problems have just about gone away. It’s like we’re brothers or something! Think this is a good time for a hug? 

“Yeah, it’s rough.” I walked past him into the bathroom. As I took out my dick to take a piss, I glanced up at the mirror above the sink. Time suddenly froze. The color fled from my already pale face. I-I have…I have hooker-blood on my dick.

I HAVE HOOKER-BLOOD ON MY DICK!

And not just there. Matted to my pubic hair, covering my balls, sticking to my lower abdomen. My entire pelvic region was covered in her blood. 

I knew everything was over. I absolutely had AIDS. Not the glorified rest stop of HIV, not gonnorhea, not syphilis. Full blown AIDS. Within weeks I would look like Tom Hanks in Philadelphia. My hair would fall out, my body would shrivel and shrink, my T-Cell count would fall to zero. I’d be dead before the end of Summer. 

I turned on the sink and put my dick under the faucet. I scrubbed myself down as best I could. Eventually the blood was all gone. I took a breath, washed my hands. It was time to go.

I came out of the bathroom and put on my jacket, checking to see that they hadn’t jacked my cell phone. Brad was sprawled out on the bed flipping channels. He seemed to be happy with his five dollars in cash and free cable for the night. Destiny sat beside him smiling meekly. I made for the door. “Alright, thanks a lot man, call again.” I walked out without responding. 

When I got home, I immediately stripped off my clothes, got in the shower, and proceeded to scrub myself like a rape victim. I knew in a couple years I would think this whole thing was hilarious, but at the time I just wanted to feel clean again.

That was five years ago. I managed to avoid catching anything, though I still feel a bit ripped off that I basically paid to have a girl menstruate on me, which is obviously what happened. Despite the fact that the night didn’t turn out quite like I expected, I did achieve my goal in a way, because after going through that, I stopped feeling quite so bad about the breakup. I had learned that there are far worse things.