New York Trip

Just after I turned sixteen, the summer before my junior year, we went on a family vacation to New York City.  I was thrilled to see the Big Apple; I was less than pleased to be going there with my parents.

I was overweight at the time.  I don’t want you to get the idea that I was fat, because I wasn’t; but I definitely wasn’t skinny either.  At the time, I also had definite ideas about what an attractive girl was supposed to look like, and I wasn’t it.  My boobs were too small, my hips too wide, my lashes weren’t long enough and didn’t naturally curl; and my lips didn’t pout right.  In short, I thought I was ugly.

I had died my hair bright red and painted my nails purple.  I wore a lot of black, and sported blue doc martins.  I thought I was oh so punk.

The three of us, Mom, Dad, and me, shared a room at the Milford Hotel, on 43rd street.  In the first excitement of arriving in the city, I forgot to be mortified to be seen in public with my parents.  The noise, bustle, and excitement of Manhattan overwhelmed me.  We had dinner together at some nice restaurant, then saw Cats on Broadway.   I thought it was the best thing I had ever seen.  By the time the show was over, all three of us were drop-dead tired; it had been a very long day.  Mom and Dad slept in their bed, I slept soundly in mine.

When I woke up, it was still very early.  I had the strange sensation of waking up not knowing just where I was at first.  The room looked alien, unfamiliar.  Traffic noise was already filtering up from the streets far below.  Through the window, I had an excellent view of a brick wall.  From somewhere far above, sunlight was starting to light up the city.  I looked at the clock radio on the nightstand.  6:25; way too early to be awake.  And yet, awake I was, inescapably awake, and ready to start exploring the great city.

I heard a rhythmic creaking sound, and realized that it was coming from my parents’ bed, not five feet away from me.  I looked over, and realized that Mom and Dad weren’t asleep as I had assumed.  Mom was lying with her back to me, her hand busy under the covers.  Dad was lying flat on his back.  They were kissing.  I realized that Mom was giving Dad a hand job.  GROSS!!  I rolled over quickly and shut my eyes tight.  I couldn’t bear to think about it.  And yet, I couldn’t escape the rhythmic squeaking of the springs, or their quickened breath as their excitement grew.  Finally, the squeaking stopped, and I heard Dad softly sigh, and I knew that he must have come.  How disgusting!  I pretended to be asleep as they got up and showered.

Mom and Dad wanted to go to all the museums that day.  I absolutely refused to go with them.  They didn’t like the idea, but I sulked and argued.  In the end, they agreed.  I was sixteen, and old enough to look after myself.  “Just be careful, and meet us back here at eight.”  And then they were gone.

I lay there on the bed for a minute, just savoring the sensation: I was free and on my own in the greatest city in the world.  It was marvelously exciting and terrifying.  I didn’t know what to do first.

I got dressed: black skirt, blue doc martins, a white button down shirt, and a black lace choker around my neck; and I plunged into the city.  I descended into the subway, bought my Metrocard, and took the train downtown.

I had a great time walking around the village, just looking at the shops and people.  I felt like this was where I was born to be.  I belonged here; here in the center of it all.  I could live here.  I certainly didn’t belong in Ohio.

Summoning all my courage, I went into a bar, trying to look confident and experienced.  It was almost noon.  The place was dark and cool inside, and almost empty.  I walked up to the bar and ordered a whiskey sour.  The bartender, a battered looking man of indeterminate age, served me without comment.

I sat there for a while, sipping my drink and congratulating myself on how cool I was.  Suddenly, I realized that I was no longer alone.  A guy had sat down at the bar right next to me.

He was older.  I was no good at guessing ages; but he was older than me.  He was tall and lean, and wore a black motorcycle jacket.  His eyes were light blue and mischievous.  He was drinking beer out of a bottle.  The brown glass bottle in his hand sweated clear drops of moisture.  My heart raced.  I wanted to introduce myself, but I didn’t know what to say.

“Are you from out of town?” His voice was rough, a little gravelly, like one who has been up all night, smoking too many cigarettes.

“Yes”, I answered, nodding, “I’m just here for the weekend.”

“Where you from?”

“Ohio.”

“Like it here?”

“Oh yes.  I sure do.” I nodded for emphasis, “Very much.”

There was a long silence.  He took a deep drag from his cigarette.  I felt tongue tied, and terribly young and awkward.

“Can I buy you a drink?”

“Sure.” I said.  My head felt light and a little spinny.

He nodded to the bartender, who brought me a new whiskey sour and a fresh beer for my companion.  He raised the bottle in a half mocking toast to me.  We drank in silence for a few minutes.

I felt his hand on my thigh, on the bare flesh above my knee.  I tried to stifle the panic that was building in my gut.  I gritted my teeth and sipped my drink, and didn’t get up and walk away in a huff.

My heart was beating so hard, I was sure he could hear it.  I realized that I was getting really physically excited.  His hand felt cool and strong on my thigh.  Later, I would masturbate to this tall, silent stranger.  I spread my legs a little, allowing him access to my upper thigh.  I felt wild and brave and out of control.

We talked for a while, about music and art and books and New York City.  He made me feel incredibly naive and inexperienced.  All the while, as we chatted, his hand was softly stroking my thigh.  It was driving me crazy.

“Listen” he said suddenly, as if the idea had just occurred to him “would you like to come over to my apartment?”

I realized that I was a little drunk.  I knew that it wasn’t a good idea.  In fact, I knew that it qualified as a Really Bad Idea.

“Sure” I said “I’d love to.”

We left the bar together, leaving our drinks unfinished.  I guess he must have paid the bill.  He negotiated us through the crowded streets and down into the subways.  After a short, loud and confusing ride, we climbed a smelly stairwell back into daylight.  He told me that we were in Brooklyn.

His apartment was five flights up.  I was glad that it wasn’t far from the subway.  I was horny, too horny to be scared, too turned on to be nervous, and if he didn’t touch me soon, I thought I might melt.

I wasn’t totally inexperienced by then.  I had gotten good at giving blowjobs, and, after an iffy start, I had realized that sucking dick was really fun.  I had been masturbating since I was twelve.  I had fooled around at camp, and in the front seat of my parents’ old car.  But I had never had a real boyfriend, and I had never gone “all the way”.

He unlocked three or four locks, and we were inside his apartment.  Suddenly we were kissing, his mouth pressed against mine, his tongue invading my mouth, his hand squeezing my sensitive breasts.  I had only the briefest impression of his place; small, messy, spare furniture, weird art on the walls.  Then we were in his bedroom.

I briefly sobered up enough to realize how deep the shit was that I was in.  He might kill me now, and nobody would ever find my body.  I held my breath, hoping that I had not made a fatal mistake.

He lay on top of me, and we kissed for what seemed like a long time.  I liked kissing him.  I liked the way his stubble scratched my cheeks.  I liked the lump in his pants, pressing urgently against my crotch.

His hands were under my shirt, massaging my breasts through my bra.  I liked that; I liked it a lot.  Pushing him away for a moment, I unbuttoned my shirt and unsnapped my bra.

“Are they alright?” I asked.  My boobs didn’t look like much, I thought, not compared to the one’s I had seen in magazines, or some of the older girls in the locker room.

In answer, he lowered his mouth to my left tit, sending sparks of electricity, straight to my twitching clit.  I reached for him, squeezing his erect cock through his black jeans.  I couldn’t wait to suck him, to have that nice stiff cock in my hungry mouth.

I felt his hand under my skirt, rubbing me through my underwear.  I was glad that I had worn my black string bikini panties.  I knew I was wet, really wet, and my panties must be soaking.  His hand felt incredibly good.  He was strong and confident, not hesitant like the boys I had fooled around with before.

I had a little trouble with his zipper, but I quickly had his cock out in all its glory.  It was big, the biggest one I had seen yet (though not, I learned later, exceptionally large).  It was really wide around; my thumb and forefinger wrapped around it didn’t quite touch.  The head was hot and purple, and a drop of clear liquid leaked out of his hole.  It looked delicious.

I really liked having him in my mouth.  I couldn’t get it all inside, but that was ok.  I licked and kissed his shaft all over, and sucked on the part I could while I stroked the shaft with one fist, and fondled his balls with my other hand.  I could tell he was enjoying it.  I was looking forward to his balls tightening up and shooting gob after gob of hot semen into my mouth.

It didn’t seem like I had been sucking him long, when he gently lifted me off his cock.

“Baby” he said “Are you ready?”

I nodded.  I knew what was going to happen, and I felt like I was outside my body, watching this happen.  I knew I was a virgin, but he didn’t.  I watched, enthralled, as tore open a condom, and rolled it onto his straining manhood.

He tore my panties off, in one quick act of violence.  I cowered in front of him, feeling more naked than I ever had before.  He guided the latex-sheathed head of his penis to my opening.  Mentally, I cringed, even as I spread my legs wide for him sighing something grown-up sounding like “Yeah, come on and fuck me now, lover.”

He entered me, and I thought my pussy was being torn in half.  I thought he must be splitting me apart, breaking me.  I closed my eyes and tried not to scream.

I looked down past his sweaty smooth chest, at the dark bush of hair between my legs, and saw his own pubes pressed close against mine.  I realized that he must be all the way inside me.  I no longer felt like I was being torn up, but I felt stretched to the limit, like a small pair of nylons pulled onto a fat lady’s legs.

“God damn you’re tight.” he grunted as he began to thrust.  My clit felt distended, jolting me with pleasure through the fog of pain every time he moved.  I didn’t know what to do, what to feel, as he pumped away at my poor pussy.

I knew he was going to come soon.  He was breathing in fast, raspy gasps, and fucking me hard and urgently.  I was still excited, desperately excited, but the pain had won out over the pleasure, and all I could do was close my eyes and wait for it to be over.

“Fuck, fuck oh yes fuck” He came inside me, collapsing on my body, filling the condom with his sperm.  I lay under him, silently crying to myself in relief and frustration.  He smelled of beer and cigarettes.  His wilting dick slipped out of me.  He got up and threw the condom away, then went to the bathroom.   I hear the toilet flush.

When I woke up, I remembered immediately where I was.  But where was that?  Somewhere in Brooklyn?  I had no idea how long I had been asleep.  My head hurt.  I was alone, and the apartment was quiet.  I was supposed to meet my parents at the hotel at eight.

I realized that I had bled on his sheets, quite a bit actually.  I laughed ruefully to myself, wondering what he would think of that.  His clock said that it was 5:30.  I put on my shirt and went out into the living room, feeling woozy, needing to pee.

When I came out of the bathroom, I noticed that there was a girl sitting on the couch, a book open in her hand, staring at me.  She was a wisp of a woman, maybe in her mid twenties; shorter than me, skinny and pale, with dirty blonde hair cascading down onto her shoulders.

“Who are you?” I asked stupidly.

“I’m Laura.” she said.  “Chris’ roommate.  Don’t worry, I’m not a girlfriend.”  She sounded friendly, and not too surprised to see a dazed girl wandering around her apartment.

“I’m Jenny.” I said, trying to sound confident and in control.

“How old are you Jenny?” Laura asked quietly “Where are you from?”

“I’m sixteen.” I said “And I don’t know how to get back to the hotel and I told my          parents I would meet them at eight.”

And then I totally lost it, breaking down in tears.  Laura got up and hugged me, holding me tight as I sobbed onto her shoulder.  We landed on the couch, and as I cried, I told her everything that had happened.  She held my hand and stroked my hair, and listened patiently until I was all cried out.

“Don’t worry Sweety.” she said “It could be a lot worse.  No permanent harm       done.  We’ll get you back to your hotel in time, and your parents will never know.       Hey, now you don’t have to worry about losing your virginity.”

I managed to laugh weakly at that.

“He did use a condom, didn’t he?”

“Yes” I answered, blushing more at my own stupidity and naivety than anything   else.

“Good.” She said.  “Like I said, no permanent harm done.”  She paused then said,             almost to herself, “You know, Chris is a real fucking bastard.”

“It’s ok.” I said.  “I knew what I was getting into.  More or less.”

“Listen.” She said holding my hand and looking me in the eye. “This is New York             City.  You can’t just go off with strangers like that.  You got really lucky kid.”

“I know.  I know.  What I did was really stupid.”  Then the tears started again.

“That fucker” I sniffed through my tears, trying to make a joke “I didn’t even get to have an orgasm.”

Laura held me for a long time there on the couch.  What a sweet woman, I thought later on, for comforting some dumb-ass girl from Ohio, in deeply over her head, as if we had been friends forever.

“You’re going to be alright” Laura pronounced.  “You’ve got a lot of life in front of you kiddo.”

I kissed her on her cheek.  She kissed me back, softly.  It was hanging out there, an unspoken question.  I kissed her cheek again, still an innocent kiss, but with a little promise hiding behind it.

“Listen Jenny” Laura said very seriously “You’ve had a really long day already.  I don’t want to take anything more away from you.”

I put my arms around her. “You wouldn’t be taking anything away from me; I’d be giving it to you.  Besides,” and I pretended to pout “I didn’t even get to come.”

She brought her lips to mine, and suddenly we were kissing for real.  It wasn’t like kissing a boy; it was softer, gentler, slower and more sensual.  She tasted nice.  I was becoming excited again, my nipples hard, my clit tingling.  I slid one hand under her t-shirt, and found her breast, unhampered by any bra.  It was the first time I had touched a breast other than my own, and I was surprised at how good it felt in my hand.  She sure seemed to like me touching it.  We kissed, deeper and more passionately.  Suddenly, she stood up, and led me by the hand into her bedroom.

She pulled off her t-shirt and stepped out of her blue jeans.  She wasn’t wearing anything underneath.  Her breasts were a little smaller than mine, but fuller, more symmetrical.  There was a neat little triangle of sand-colored hair above her pussy.  I thought she looked beautiful.  I was suddenly self-conscious of my own less-than-perfect body.

“Come here,” said Laura, drawing me to her on the bed.  I let her unbutton my      shirt, exposing my body to her.  “You’re beautiful” She whispered in my ear.

Her nipples pressed against mine as we kissed, stimulating me wickedly.

“I’d like to lick you” I said haltingly “I’d like to eat your pussy.”

She grinned.  “I was hoping you would.”  She lay back down on her bed,   spreading her legs wide for me.

It was the first time I had ever seen a vagina close up.  The illustrations in health class just didn’t do it justice.  It looked beautiful, like a dewy rose layed out just for me.  It was intimidating.  I didn’t know where to start.  I just hoped that I would be able to find her clit.  Tentatively, I stuck out my tongue, and softly licked her labia.

I don’t know what I expected it to taste like.  I had hoped it wouldn’t taste bad, that I wouldn’t gag.  I really wanted to give her pleasure.  Laura’s taste was a pleasant surprise; musky, clean, salty, tangy, and sexual.  I licked again, parting her lips with my tongue.  Her clit was there, peeking out from its little hood.  I touched it with the tip of my tongue, and she jumped a little.

I licked and licked, losing myself in her pussy.  She was wet.  I loved her wetness, loved that I was the cause of it. I wanted to make her come.

“Listen,” Laura said “you can put a couple fingers in if you want.”

I slipped my index finger up into her hungry hole.  She was hot and slippery inside.  Her pussy walls seemed to grasp my finger, pulling me inside.

“Yes” she gasped “More.”

I put another finger in, then another.  I couldn’t believe how much her vagina was opening up for me.  I had four fingers all the way inside her when she groaned “That’s it baby, now fuck me, fuck me hard.”

I kept my tongue on her clit as I fucked her with all four fingers of one hand.  Fucking her was a joy.  I felt so powerful, so connected to her.  When she came, gasping my name and shaking, stomach heaving and spasming, I almost cried.

“Now it’s your turn” she said after we had cuddled for a little while.  I was more than ready for her.  She devilishly sucked my nipples, drawing my whole breast into her mouth before releasing it with a “Pop!”; nibbling and pulling on my nipples until I couldn’t stand it anymore.

“Please Laura”, I begged “Please lick my pussy!”

She grinned wickedly.  “I was just waiting for you to ask.”

Her tongue on my pussy felt like heaven.  My clit throbbed for attention.  I thought I must be wetter than I ever had been before.  I had never thought seriously before about having sex with another girl; now I wondered if I would ever want it any other way.

She started to put a finger in my pussy, but it hurt.  I was still too sore.  I hoped she wasn’t disappointed.

“Don’t worry about it Sweety” she said before going back down between my legs.            “Just lie back and relax.”

I felt her finger probing between my cheeks as her tongue strummed my clitoris.  At first I thought it was a mistake, but the exploring finger was insistent, probing closer and closer to my anus.  I panicked, stiffening up and pulling away from her.

“Relax.” Laura said.  “Look at me.  Just relax.  I promise I won’t hurt you.”

I had heard about anal sex, but I for one wanted no part in it.  It was gross and scary, and not for me.  But, looking at Laura, I decided that if that was what she wanted, I would give it to her.

Laura returned her mouth to my needy clitoris, and her finger boldly explored my backside.  She found my anus and pressed gently against it.  I willed myself to relax my clenched hole.  I was torn between the edge of an orgasm from her mouth, and the edge of panic from her finger invading my ass.

Then her finger was inside me.  It felt strange back there.  My body clenched down on it; clenched down again, then finally relaxed.  She was moving her finger very slightly in and out, like she was butt-fucking me with a tiny penis.  I was surprised, and a little alarmed to realize that it felt very very good.

“I want to get more inside you.” she said.  I realized that she was pouring clear      liquid from a small bottle onto her fingers.

“Go ahead” I whispered “Just be gentle, ok?”

“I will be.”

My clit was aching for her attention.  I was a hairs breadth from coming all over her tongue.  Her finger slipped into my anus more easily this time, and I found myself squirming back against her, trying to get her all the way up my butt.

“Can I put another in?”

“Yeah.”

I felt stretched. I felt full, but it didn’t hurt.  It felt good.  Really, really good.

“Fuck me harder” I said. “I like the way you feel inside me.”

She told me later she had three fingers up my ass.  Well, she had small hands.  It felt huge, it felt like the entire universe back there.  As my orgasm started, as I finally released, and the waves of pleasure that had been building up all day finally washed over me, she fucked my ass hard and sucked my clit.  I bucked and ground into her face, mashing myself onto her lips, grinding my ass against her hand.

When I was done coming, we took a shower together.  I wanted to have sex again, but it was getting late.  My panties were ruined; she loaned me a pair of her own.  She called a car service for me, kissed me deeply, and pressed a piece of paper with her phone number on it into my hand.

I got back to the hotel at 8:05.  Fortunately, Mom and Dad were twenty minutes late.  We went to see another show, “Les Miserables”.  I had trouble staying awake for the whole thing.  After the show, we all went to a bar, and my parents allowed me to have a drink with them.  When they asked me about my day, I said that I had just walked around and looked at things.

The next night, during the long car ride home, when Dad was asleep in the front, and Mom was silent behind the wheel, classic rock on the radio and endless cornfields to either side of the freeway, I masturbated quietly inside Laura’s candy-striped panties.  I had her phone number on the little slip of paper in my purse, and I knew I would call her soon.

1 Comment »

  1. Wow great read :]. I enjoyed the whole thing!

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