Chester’s Ex

This is about 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; back then 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 fucking 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.”

Actually Rachel and I had never hung out.  Both she and Chester were in their thirties, and immersed in academia.  We had rarely even crossed paths in the apartment before.

“Listen, Andrea” she said, taking a step forward.  My nipples were erect, I noticed embarrassedly, and I didn’t really know why “Before I leave do you think…”

“What?”

“No, never mind, it’s too stupid.”

“No” I said “Go on.”

Now it was Rachel who was blushing.  “Do you think I could… just… kiss you once?”

“Yeah” I whispered “That would be ok.”  I hadn’t been kissed in months, by anyone, male or female.  I felt weak in the knees.

Shyly, Rachel kissed me on the lips.  I reached my arms around her girth, my fingers not touching behind her, and kissed her hungrily back.  I could feel her body heat radiating through her clothes.  My smaller naked breasts were pressed against her bosom.  Somehow the towel around my waist came undone, and fell to the floor. The kiss went on and on.  I let my tongue slip into her mouth, exploring.  Her tongue met mine and wrestled playfully.  Finally, we broke off, and she took a step backward.

“God Andrea you are so beautiful.” I could feel her eyes traveling over my naked body “You are really going to break some hearts in this town.  Can we…?  Do you want to…?”

“Yes.” I answered huskily.  I could already feel the heat building between my legs.  Together we ran into my bedroom, landing entwined on my bed.  “Those clothes have to come off” I said “Like, now!”

Sitting up, Rachel pulled off her t-shirt and bra, releasing her exceptionally large boobs.  She unbuttoned and peeled off her tight jeans, revealing a skimpy purple thong.  I could already smell her excitement, and it only made me more horny.  In other circumstances, I might have thought that the tiny purple panties looked silly on her wide expanse of pale flesh, with her stomach hanging down, and her thighs bulging out.  Right now though, I thought they looked sexy, and I wanted to get at what was underneath them.

She watched me watch her as she pulled off her underwear, revealing a totally hairless vagina.  I had never seen one like that in person; I had always thought it was a vaguely creepy and distinctly heterosexual conceit.  Her pussy changed my mind: the waxed look was beautiful for her, emphasizing her curves and softness.  I loved that I could see every little detail of her sex.  Her labia were just peeking out, and a small stainless steel ring pierced one pink lip.

We attacked each other, kissing passionately.  I let my hands travel all over her body before finding the wetness between her legs.  She gasped and bore down on my finger as I rubbed her hard little clit.  Her big tits pressed against me, and she held me close, kissing me deeply as I fingered her.  She shook like a kitten as she came on my unrelenting fingers, moaning into my mouth.

With a sigh, she fell back on the bed, spreading her legs to give me full access.  Her pussy was very wet, dribbling girl come down the crack between her cheeks.  Her labia were swollen and parted like the petals of a rose.  The ring that pierced her left lip glistened invitingly.  I could see her little pink clitoris peeking out from beneath its hood.

It had been a long time since I had tasted pussy (my own excepted), and I wanted to savor the moment.  I stuck out my tongue and delicately traced her opening, from the bottom where her ass cheeks met, up between her pouting lips, and up and around (but not touching) her swollen clit.  She tasted really nice.  Unlike, I’m sorry to say, other girls I have been with, she just tasted clean and a little bit salty.  I savored her sex.  Licking all over her pussy, but avoided her clit for now, I started exploring her with my finger.  She was leaking copiously, and my finger was soon coated in her slippery come.  I slipped it inside her pussy, which welcomed my finger, hot and grasping.  I let my finger slip out and trace down the crack of her pussy, probing between her ass cheeks.

“Yes!  Oh God Andrea Yes!”  She lifted her legs up in the air, raising and spreading her ass for me.  Her asshole, tiny and crinkled, winked invitingly at me.

I let my finger trace the crack between her cheeks, gently stroking the sensitive skin between her pussy and anus.  Tentatively, I circled her little brown hole.  I’d never really looked closely at a butt hole before.  I thought hers looked really cute.  It seemed like such a small hole for her big body.  I wondered how Chester ever got his whole penis up into it.  Absently, I stroked her pussy with the fingers of my other hand as I enjoyed the view of her backside all spread out and vulnerable just for me.  She was begging me loudly at this point “Andrea Baby please touch my asshole, I want to feel your fingers back there!”

A little hesitantly, I pressed my fingertip against her opening.  I didn’t want to hurt her.  Her asshole seemed to open up to swallow my fingertip.  I was surprised at how tight she was back there.  It almost felt like my finger was being devoured by a hungry little mouth.  I pressed in a little, and she pushed back hard, swallowing my finger halfway to the knuckle.  She was moaning incoherently now.  I slipped another finger into her pussy, and concentrated on her ass.

It wasn’t long before my finger was all the way up her hot tight butt hole.  I started fucking her ass with it, alternating strokes with the fingers in her pussy.  I was incredibly turned on at this point, as the juices running down my thighs would testify.  I fucked her harder and harder as our excitement peaked.

“Oh Yes Andrea!  Fuck me! Oh fuck yes!” she shouted, so loud I thought people out on the street would hear us.  I looked up from my anal ministrations, and was amazed to see that I had all five fingers of one hand buried in her cunt.  Now I have small hands, but not that small! It felt amazing to have my entire hand up inside her vagina.  I fucked her with my fist, and slipped another finger up her rear.  The sensation of her coming, choking on her screams, bucking and writhing on me was one of the sexiest things I had ever experienced.  I let my hand and my fingers, coated in her juice, slide out of her limp body.

“Oh Baby” she purred “You’re good.”

She kissed her way down my body, pausing to lick some of the come off my hand.  My clit was quivering with anticipation.  She took her time, sucking on each nipple, nibbling each breast, kissing me all over my tummy and thighs before turning her attention to my aching pussy.

I spread my legs wide for her.  Her tongue felt heavenly on my pussy, and my clit ached for her.  I wanted her to fuck my pussy and lick my clit.  But more than that I wanted…

“So that’s what you want?” she asked, caressing my backside.  I hadn’t realized that I was being so obvious.  I felt like a tramp, my legs in the air and my bottom exposed.  “Why don’t you just roll over?”

I got on my hands and knees on the mattress, and she came at me from behind.  She caressed up and down my back, reaching around to play with my hanging boobs, and then slid down into the virgin territory between my ass cheeks.  I buried my face in a pillow and enjoyed the sensation of her hot breath on my ass.  She was licking me there, up and down the tender flesh between my ass cheeks, and it was driving me crazy.  Suddenly she stopped.  I stayed there, paralyzed, needing her touch.

“Ask me for it.” she said “I want to hear it from your lips.”

“Please…” I said.

“Please what?”

“Please” I went on “I need to feel you there.”

“Where?  Tell me where.”

“My asshole” I begged “Please.”

“Aha!” she gloated “And what do you want me to do to your naughty little asshole?”

“Please” I said in a small voice, feeling very self-conscious “Please Rachel, please lick me and fuck me in the ass.”

She didn’t torture me any more, but put her face between my cheeks and started licking my anus.  It was the most exquisite sensation.  At the same time, she reached between my thighs and started gently rubbing my button.

It was incredible.  It felt so good, I thought I would melt.  I felt like I was in a state of constant orgasm.

“Rachel” I gasped “I need to feel you inside me!  I need you to fuck me in the ass!”

She withdrew her tongue, which felt like it had been about eight inches up my rectum, and pressed her fat finger against my opening.  I closed my eyes and bore down on her.

It felt wild to have her finger back there.  It was a sensation I had never felt before.  Not painful, certainly not that.  Her finger felt huge back there.  I liked it, but I didn’t know how much I could take.

She flipped me over on my back, leaving her finger up my rear, and attacked my clit with her tongue.  She slipped her thumb up my hungry pussy, and played me like a hand puppet as she licked.  I totally lost control.  It seemed like my orgasm went on forever, washing over me in wave after wave of pleasure.  At last it was over, and she withdrew her fingers, leaving me a limp, shivering shell.

She didn’t have much to say to me.  She got up and used the bathroom, and then I watched her get dressed and leave with her boxes.  She left her key on the kitchen counter.  “I’ll see you around” she said as she went out the door, but I doubted it.

My asshole felt tender and hot.  My pussy was still leaking and my clit was tender. I felt relaxed, and a little bit used.  I got up to take a second shower.  I would masturbate to the fresh memory of Rachel fucking me in the ass.  I really needed to start dating again.

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