This was my first summer in New York City. The twin towers still stood, tall and proud, a much-needed landmark for a disoriented girl from Ohio exiting the subway into the intense confusion of the streets of Manhattan. I was twenty-one years old, underemployed, broke, and basically friendless in a big and intimidating city. At the time I was sharing a crappy two bedroom apartment on the lower east side with a guy named Chester. Chester was a grad student at NYU; he had advertised for a roommate in the Village Voice. He was a nice enough guy, but very busy with his thesis, and we didn't really have a lot in common. He was trying to get his doctorate in Russian Literature; I was a theatre geek. So while we got along ok, we didn't have much to talk about.
The apartment was indeed crappy. It was cramped and dark, and on a scary block (this was back in the days when there were still scary blocks in lower Manhattan). It had been advertised as a two bedroom, but that was a stretch: you had to walk through my bedroom to get into Chester's room, which had been created by the expedient of nailing up a wall of unpainted half-inch plywood across the middle of the original single bedroom. The only upside, Chester and I agreed, was that it was dirt cheap. And the plumbing worked reasonably well.
Chester had a girlfriend. Her name was Rachel, and she was a big girl, big in every sense of the word: tall, busty, brash, loud, and overweight. Not the kind of girl I often find myself attracted to. Chester wasn't my type either. He was tall and stringy, and kind of pale with a bad complexion. I think he spent too much time in libraries and coffee houses, and never got enough sun or exercise. I guess that's what grad school will do to you. He and Rachel had a rocky, on again, off again relationship. Their fights and breakups could be spectacular, but so were their reconciliations.
I confess that I used to eavesdrop on them. I was lonely and horny, and masturbation was my only sexual outlet. I hadn't yet discovered porn (I still thought it was just for guys), or sex toys; it was just me and my fingers alone in the darkness. So when Chester and Rachel came tiptoeing through my room late at night, giggling and trying not to trip over my futon, I just pretended to be asleep. As soon as the hinged sheet of plywood that passed for a door had closed, however, I would creep out of bed and press my ear against the ridiculously thin wall.
Rachel in particular was very demonstrative in bed. I used to kneel by the bedroom divider with one hand down the front of my panties, listening to their sex noises. I could hear Chester's bed squeak in time with his thrusting, I could hear their moans and groans and giggles and sighs, and sometimes I could even hear the slurping and squishing noises of them having sex. It was sexy and titillating to my sex-starved ears and it really made my pussy drool. What really got me going though was listening to Rachel. Invariably, she would start out whispering, trying to be quiet: "Oh please Chester, fuck me now." "Mmm lover, let me suck your big hard cock." "Oh Baby you lick my pussy so good!" As she got worked up, however, she got louder and more enthusiastic, to the point where I would have heard her even if I had been lying in my bed with the pillow over my head. "Yeah Baby fuck me, fuck me hard! I want to feel you come in my pussy!" "Oh yeah God I'm going to come all over your big dick!" "Oh yeah yeah yeah you're so hot you big stud!"
This really got me going. I would rub my clit and let my orgasm wash over me as I listened to them. It was hard to picture Chester as a big stud, and the image of either one of them naked didn't do anything for me, but the sound of them passionately enjoying each other really turned me on. I felt a little guilty for spying, but not guilty enough to stop.
One night, when I was kneeling next to the wall listening in on them, fingers busy between my thighs, I heard Rachel blurt out "Chester Baby, I want you to fuck me in the ass."
I was shocked. I listened intently, petting my clit, as they went on. "Oh god your tongue feels so good in my butt... I'm going to come just from that..." "I can't believe you just have one finger in there... it feels huge" "Put it in Lover, I can't wait much longer." "Put a little more lube on... Slow.... Oh yeah... OH YEAH! OH YEAH LOVER FUCK ME, FUCK MY ASS!" I rubbed myself into a state of bliss listening to their mutual orgasm.
I had never thought much of anal sex before. It was something that men did to women; unhygienic, degrading and painful. My college roommate had once confided in me that her boyfriend wanted to try anal sex. "Gross!" I had said.
So listening to Rachel enthusiastically take it up the ass was something of a revelation for me. My world was, so to speak, turned upside down. For some reason it got into my head and wouldn't quite go away. I was fascinated. I even went so far as to try fingering my own butt as I masturbated. It didn't do much for me.
Rachel and Chester finally broke up for good. I overheard a lot of their last fight, and it was ugly. I felt bad for both of them. But I also felt bad for myself, selfishly, because I knew I wouldn't be able to listen in on their sex anymore.
Not having a regular job, I usually slept late and went for a run before the day got really hot. Chester always left the apartment early; he spent his days at the library, and then hung out at coffee shops talking Russian Literature with his friends until late. He didn't often make it home before midnight. So when I got back from my run, I had no qualms about pulling off my sweaty clothes and stretching out naked before I took a shower.
When I came out of the shower, naked except for a towel wrapped casually around my waist, I must have yelped in surprise: Rachel was in the living room, on her knees, packing books into a cardboard box.
"Andrea!" she was obviously just as surprised as I was "I'm sorry. I didn't think anyone was home. I was just collecting the last of my things, and dropping off the door key."
"That's ok." I said, as my heart rate started to return to normal "You just surprised me. I'm sorry about you and Chester."
"Don't worry about it" she said "It's no great loss, trust me. I'll miss the sex, but not much else."
Unbidden, the image of Rachel, naked on all fours on Chester's bed; her pendulous breasts hanging down, her wide rump thrust up in the air, taking Chester's rampant cock deep in her asshole flashed through my mind. I blushed deeply.
"Of course you probably knew about the sex" Rachel went on "the walls are pretty thin. I'm sorry if we ever disturbed you."
"Um no" I stammered, still blushing "I never really..."
"Hey" Rachel said, standing up and facing me "I'm really going to miss you Andrea. I'll miss hanging out with you."
