by Chad Kultgen
We hadn’t talked about what that would mean to her or to me or to us in general. It all felt a little strange, like we were slipping right back into some kind of a relationship without even addressing it. Even as drunk as I was, I could tell it was weird. But I didn’t care enough to stop it. I did want to have sex with her. The semester I spent having nameless sex with the girls Brett set me up with taught me that, no matter how weird it is, as soon as you put your penis in a vagina, it’s not weird enough to make you take your penis out of that vagina.
She pulled me down on top of her and started taking off her clothes. I knew it was wrong but I didn’t stop it from happening. She gave me a blowjob that reminded me how average she was at giving blowjobs. When I only had Heather to compare her to I always just thought that Erin was slightly worse than Heather, but since Heather dumped me I had had enough experience to create a hundred-point scale of blowjob skill, and Erin ranked somewhere in the thirty to forty range. Still, she was good enough.
When she lay back on her bed, I didn’t even make an attempt to go down on her. I just rolled her over and started having sex with her from behind. After about two thrusts she said, “Wait. I’m not on the pill or anything.”
I stopped and said, “Do you have any condoms?”
She said, “I just moved into this place two days ago, so if I do, I don’t know where they are.”
I wasn’t mad or even really disappointed. I just got off her and went to pick up my underwear from the ground. Then she said, “Well, just be careful and make sure you don’t finish inside.”
Even drunk this seemed like a bad idea. I said, “Are you sure?”
She said, “Yeah. It’ll be fine.”
So I got back on top of her and started having sex with her again. I didn’t enjoy it at all. Through the whole thing I just felt bad, like I was using her, like I was letting her feel something about me that wasn’t true. I knew I didn’t want to get back together with her under any circumstance. And it wasn’t because she wasn’t great. She was. She was the best girlfriend I ever had. It was because I just didn’t want to care about somebody again.
As I was having sex with her, she started moaning and she rolled over so she was facing me. She reached up and kissed me while I was on top of her. She still loved me. I kind of panicked. I wanted her to understand that I wasn’t doing this because I felt anything for her. I wanted her to understand that I just needed to do this to prove to myself that I had no more feelings for anyone. I wanted her to understand that I wasn’t the same person she used to love.
So I started thrusting a little harder at first and then really hard. She kind of winced in pain a few times, but I didn’t stop. I kept going harder and harder. At one point I was thrusting into her so hard I actually hurt myself when my hip hit her leg. I just wanted her to see that the old Kyle was gone and I guess some part of me wanted to see that, too. I wanted to prove to myself that I could be there with the only girl who really loved me and not care at all about her.
Right before I was about to cum, I pulled out, and just to punctuate everything I was feeling in that moment I came in Erin’s face. It was horrible. She kind of halfheartedly pretended to like it, but I could tell she was disgusted. I was, too. When she left to go clean her face off, I got dressed and left.
When I got back to my place, I finished the rest of the bottle of vodka and I started to notice something. Where before I had managed to maintain a level of numbness and apathy about everything, I now noticed something new coming to the surface. I couldn’t get the image of Erin recoiling as my semen hit her in the face out of my head. I hated myself, and more than that I started to hate Heather for turning me into what I had become. Erin called me a few times that night but I never answered.
And so began the worst year of my fucking life.
chapter two
The first day back was like seriously not fun. I ended up getting a new room at the house because I was a senior, but that was about the only thing good that happened that day. After I moved in I went downstairs and like pretty much every girl was talking about how their boyfriends proposed to them over the summer or how they were going to be proposed to in the first semester or at Christmas or whatever. I wanted to fucking jump off a cliff. And then they were all like, “There’s a big party going on over at Pike, we’re all going, you should go.” So, of course, I went because I just wanted to get as drunk as possible and maybe do some coke and just not think about it anymore.
As soon as I got there, I did some E and started drinking and then like half an hour later I ran into Brian, of course. I should have fucking known that was going to happen. So I like tried to be nice and everything. I was like, “How was your summer?”
He was like, “Pretty good. Interned at Lairmoore and Grummin. Made some pretty decent contacts and everything. How about you?”
Despite the fact that it was seriously shitty, I was like, “It was pretty good, just relaxed. You know, chilled out a lot.”
He was like, “Cool. Cool.”
I was like, “So is Annie here?”
He was like, “No, she’s not coming back until tomorrow. On some vacay with her mom.”
I was like, “Oh.”
He was like, “Yeah.”
I was like, “Well, good seeing you. I think I’m going to get a drink.”
Then I left and went toward the kitchen and he like seriously followed me in there. He was like, “For real, I’m sorry about that day we talked last semester. It was weird and I guess I’m just sorry if it was too weird, you know?”
I was like, “Yeah, it’s fine.”
He was like, “Okay. Cool. I just wanted to make sure.”
I was like, “Yeah.”
Then he gave me a hug and I let him and he did feel seriously good. I had forgotten how much Brian worked out and how hot his body was. I know it was probably the E but I couldn’t like help it, I just kind of reached down and grabbed his butt. He had like those dents on the side of it, you know when a guy has like a really tight butt how it has those dents, his had those.
He was like, “Whoa, for real?”
I was like, “Sorry. I just—Sorry.”
He was like, “Do you want to go to my room or something?”
I was like, “What about Annie?”
He was like, “She doesn’t come back until tomorrow.”
I was like, “Yeah, okay.”
And he took me back into his room, which thank God wasn’t the same room as the one he and Josh did what they did to me in. I don’t know if I would have been able to handle it.
I don’t really know what I was thinking or what I expected from having sex with Brian, but it was pretty much like every time we had sex when we were together. It was only doggy style and he did it a little too hard to actually feel good the whole time and he finished before I did and then didn’t do anything to help me get off. The worst part of it was he kind of pushed on the back of my head at one point and like smashed my face in his pillow. I don’t think he did it on purpose, but it made me feel like shit, like he was just using me to get off, and I guess he was, but it still made me feel like shit.
When he was done he got dressed like really quick and was like, “I’m gonna head back out to the party. Wait a few before you come out. Cool?”
I was like, “Yeah.”
Then he left and I just stayed there in his bed for a few minutes thinking about the fact that he would be fucking Annie in the same bed in less than twenty-four hours probably. I don’t know why I fucked him. I guess I thought that like there might be some way to get him back or that for a second I could at least feel like there was a guy who didn’t just want to fuck me. For like half a second I thought about what Kyle was doing and wondered if I made the right decision by dumping him. But then I was like uh yeah I made the right decision. He gave me a fucking fake ring.
I heard Josh out in the hall. He wasn’t coming in Brian’s room or anything but I had literally not seen him since the whole thing happened and
I didn’t really want to so I just stayed there in Brian’s bed for like another hour. He never came back to check on me and I didn’t see him again for the rest of the night.
When I finally came out of his room, the party was seriously completely full of people and it was pretty easy to sneak out without seeing Brian or any of my sisters. I went back to the Kappa house and looked over my course schedule and started thinking about the fact that I was actually probably going to have to work when I graduated and that work was probably going to be teaching little kids all day long, seriously.
chapter three
Viking’s Resort was, in short, the greatest place on planet Earth. The resort was situated on a small island in the Caribbean and was populated by thirty to forty literal whores—prostitutes.
When selecting my vacation package from the Viking’s Resort website I was given three choices ranging in price from four thousand dollars to twelve. The lowest end of the spectrum allowed for the choosing of just one prostitute who would remain by my side for all four days of my stay on the island. The next level up allowed for a new prostitute every twenty-four hours and the final level offered me unfettered free rein of all the prostitutes for my entire stay. I, of course, opted for this last package.
As soon as I arrived on the island I was greeted by the island’s proprietor, or at least the woman whose job it was to serve as the face of Viking’s Resort. She welcomed me and showed me to my room, which was a nice bungalow-style suite next to a pool. All the while prostitutes who were semi- or fully nude lounged around in the sun and generally attempted to make themselves known to me.
The proprietor made it clear that although tips were not necessary, the prostitutes would accept them and this meant that some of them were willing to work extra hard for these potential tips. She asked me if I had any questions and then wished me a good vacation and I never saw her again.
I put my bag down on the bed, put on a bathing suit, and headed to the pool. It was apparently already made known to the prostitutes that I had opted for the most decadent package because they flocked to me immediately, rubbing my back, kissing me—one even started to manually stimulate me, all before I had uttered a word. In some way it was almost like a more streamlined version of SMU.
The first prostitute I fucked while at Viking’s Resort was a girl who gave her name as Natasha. She had a thick Slavic accent. I never asked the specifics of her origin because after I blew a load in her eyes just twenty minutes after my arrival on the island I found small talk to be pointless. And beyond that she seemed to care as little about the pretense of false interest in one another as I did. It was novel.
The first day I was there I fucked six different girls, most of them in all of their holes. One escaped having my dick in her ass because she was so adept at riding my dick with her cunt that I was unable to hold back an orgasm before I could get my full money’s worth out of her. Each of the prostitutes had the same lack of interest in pretense that the first one did. As I slept that first night, virtually spent from a full ten hours of fucking, I became aware of the fact that I would have to visit this island at least twice a year. I felt a calm that was previously unknown to me, a certain contentment that I reasoned I would never experience when dealing with women who were anything but actual prostitutes.
The next morning is when I first encountered Tim Garlin, the only other man on the island during my stay. I met him on my way to one of the pools that I hadn’t yet seen. He had two naked prostitutes with him, both black. He nodded to me and made some comment about us being the only two guys on the island. Then he gave me a fist bump.
I had breakfast, face-fucked a prostitute on the fourth hole of the golf course, and then returned to the pool as I had no real interest in golf beyond face-fucking a prostitute on the course. Back at the pool I ran into Tim again, and it was this second encounter that yielded a conversation about his profession, which revealed that he knew who my father was and had done some business with his company. He asked me if I was next in line to run Keller Shipping. I told him I was, and chose not to tell him that I had decided to reject the position and the life that came with it. I didn’t want to waste any time on the island thinking about my life back home and the inevitable conversation that I was going to have to have with my father very soon.
That night I had a four-way with prostitutes who were Asian, Indian, and one who looked like she was fourteen. I didn’t ask her age and instead chose to assume that the island would have only employed prostitutes of consenting age. In any case, after I came in the face of the prostitute who looked fourteen, I watched the Asian eat the Indian’s asshole for a few minutes and as I did my thoughts turned to Kyle briefly. I wondered if he would have enjoyed the trip to Viking’s Resort. I hoped he wasn’t reverting back to his old obsession with Heather in my absence and was slightly anxious to get back home and make sure he wasn’t. But I still had two more days on the island.
The third day brought with it my strangest moment on the island when I woke up from a thirty-minute afternoon nap to find Annika, a prostitute from the Eastern Bloc whom I had fucked on day one of my vacation, sitting in a chair in my room. I left the doors not only unlocked but open in order to enjoy the mild weather, but had yet to have a prostitute enter my room uninvited, let alone while I was sleeping. It wasn’t alarming, but I was slightly unsettled. She proceeded to tell me that it was her dream to come to America. She further explained that it was against the rules of the island to talk to me about such things but she didn’t care. I seemed like a nice guy to her and she thought she could trust me. She told me that she would essentially be my sex slave in America as long as I could pay for her living expenses. There was something so candid in what she said to me, so bereft of any of the lies I was used to dealing with back in Dallas, that I found myself feeling something bordering on respect for this girl. Although I admired the forthrightness of her offer, I had to decline, which led her to tears immediately.
It was strange, but I felt some actual sympathy for this prostitute. I assumed she had probably used this same story on every guy she had fucked on the island, which I’m sure was a number too high to calculate. Her only goal in all of the fucking she did was to come to America—not to marry a rich man, or to have a giant diamond ring, or to trap a man into marriage by having his child, just to come to America, and it would never happen for her. Despite the fact that I didn’t need to subscribe to the philosophy in my own life, I always admired the people who lived by the credo that through hard work you can achieve anything. And there sitting in front of me was living proof that the philosophy was inaccurate. I fucked her against my bedroom wall, but in the middle of the act felt I should take her to the bed. She continued to cry a little as we fucked, which prompted me to fuck her missionary style, which was something I almost never did, as I had grown tired of it at a young age. While on top of her, I couldn’t help but look into her eyes and see the extreme sorrow that could only have been accumulated through years of being a prostitute. I found myself stroking her hair and telling her that everything would be fine. As I did this I lost the desire to fuck her. I pulled out and lay beside her instead. It was strange what I felt for this girl. I assumed it was similar to what most men feel for their girlfriends or wives. It clearly wasn’t anything approaching the lie of love, but I did have a certain admiration for her ability to exist without the pretense that all the other women I was used to had come to brandish in every moment of their lives. She stayed with me that night. Eventually she stopped crying and fell asleep next to me. I continued to stroke her hair as a novelty, knowing I would never have the inclination to do such a thing to another slut once I returned home.
On my final day on the island I found myself so sated from the prior three days of fucking prostitutes, and slightly disoriented from the previous night’s platonic interaction with Annika, that I had little desire to continue. But like an obese person at an all-you-can-eat buffet I was determined to get every ounce of value from the trip
that I could. I arranged, that final afternoon, to have ten prostitutes sent to my room, where I planned to engage in as many acts of demoralization as I could until my time was up.
I planned to go far beyond regular sex. I wished to piss on several of them, to shit on one or more of them, to place foreign objects like pencils and lotion bottles in their cunts, to put one or more of their faces in the toilet and flush it while fucking her doggy style, et cetera. But when the whores arrived in my room it became obvious to me that none of these plans would come to fruition. Instead I found myself wanting to see Annika one final time.
I ordered the other whores to leave and replaced them with Annika. We had a conversation about how long she had been on the island and about what led her to become a prostitute. She had been there for one year and it was only because she felt it gave her the greatest possible opportunity to find a way to America. She explained that most of the girls on the island would just come for a few weeks at a time, then return home after having made some money only to come back a few months later. They treated it almost like a part-time job. Annika, however, explained that she could never return home, not even for a brief stay. Her home was worse than hell, or so she claimed, and although she did not particularly enjoy being a prostitute it was better than the horrors she would no doubt be made to endure in her hometown.
The problems she had seemed real to me and of consequence. Annika seemed real to me, far more real than the ciphers I had dealt with all my life. This stirred something in me. I kissed Annika gently and laid her down on the bed. I began fucking her in the missionary position again. As insane as this sounds, I felt I could trust her, because her honesty, up to that point, had been absolute. For this reason I failed to wear a condom.
In my head there were many good reasons for doing this. Annika was the only girl on the island I fucked without a condom. She probably wouldn’t get pregnant because on the fourth and final day of my stay my ability to produce sperm was likely so muted I would be incapable of fathering a child. If she did get pregnant she would most likely abort it. Even if she didn’t there would be no way the child could be traced back to me. Even if it was traced back to me it would be amusing in some way to have a child with a prostitute. But beyond the practical reasons, I just wanted to feel as close to her as I could, just to experience that with a woman once.
