Watching Nina

I come down to New York City from the wilds of Southern New Hampshire at least once a month on business. Having grown up in the suburbs of Manhattan, my allegiances are still strong to the Big Apple, despite several decades in the exurbs of Boston and the pull of the Red Sox nation. It never ceases to amaze me that you can be wandering through a city of eight million people and, by chance, run into someone you know. I know it's called a small world for a reason, but I am, nevertheless, constantly amazed at the place serendipity plays in our lives.

This story is about just such an occurrence, and one that still has me shaking my head in amazement. Having just happened last week it is still fresh in my mind, and will surely remain as the most fortuitous of my random meetings.

I was in the city for a three day/two night trip. I had a few morning meetings the first day there and had spent that afternoon at MOMA and doing a little shopping. I was taking a nice long walk on this pleasant spring afternoon, heading back up Madison Avenue to my hotel on the Upper East Side. It was as I was stepping onto the curb at East 67th Street that I saw her: Nina.

My younger brother, Billy, had dated Nina back in high school. They are both in their mid-twenties now, and to my knowledge, hadn't been in contact with one another in quite a few years. But Nina was not someone you forget soon, and I had often wondered how my brother had managed to let this lithe beauty escape. I did a second take as she strode confidently across my path, unaware of my presence. I had to say something.

"Nina?"

She broke stride momentarily, eyeing me with the suspicion that New Yorkers are either born with or acquire soon after moving to the city. She observed me with a quizzical look and then brightened with that incredible smile that used to make my knees wobble.

"Ben? Oh my God! What are you...what a surprise? How are you?"

She opened her arms and I gladly received her hug, a warm welcome indeed, and one I accepted and cherished as I lightly placed my hands on her slender back and gave her a brief peck on the cheek. A whiff of expensive perfume throttled my brain.

"Well, I wasn't exactly expecting to run into you. What an incredible surprise. How are you, Nina?" I asked expectantly.

"I'm doing great, thanks. And how about you? How's the family? And Billy? God, I haven't heard from him in, like, forever."

His loss I thought under my breath. Billy was now living in DC, but had always had a way with the ladies as he was growing up. I had loved watching the parade of beautiful young women he had squired through our house over the years, starting in early high school. Neither one of us had ever had a problem attracting women, but I used to love watching the ladies Billy attracted. He had done alright for himself over the years.

I am five years older than Billy, so our academic paths never quite crossed and he was younger by enough years that we never really hung out in our formative years. But I had spent one summer at home before Billy's senior year in high school and about the same time he had started going out with Nina. That was the first time we had really bonded as brothers and Billy was sexually well beyond my fumbling years as a high school student.

Nina spent a lot of time around our house that summer and I remembered her as an incredible flirt. I knew she and Billy were very active sexually, as I will describe, but I had also felt a bond with her whenever we came in contact. Perhaps it was the "older brother" thing that she was fascinated by, but the way she made eye contact, the way she moved when I was around, the way she talked to me and smiled, the way she laughed at my jokes, all led me to believe that there was a connection, even if it was only in my imagination.

She was a long lean 5'-6", but curvy in all the right places. Her curves came more from bone structure than flesh, and she carried her frame with a sexual grace that defied description. She wasn't shy about showing off her body and always wore clothes that accentuated her tight ass and showcased her breasts. While not large they were perfectly proportioned to her frame and more than once I'd seen her stiff nipples poking through the tight tank tops she sometimes wore. Her face, while cute and very innocent at times, could look sultry and seductive at others. She conveyed, despite her youth, sexuality beyond her years.

Of all the young ladies Billy had gone out with over the years, at least the ones I knew about, Nina had always been my favorite. They had begun going out in the summer prior to their senior year and their relationship had straddled into, but not survived, their entries into the college world. Billy had headed south to school and Nina had gone out to Ohio. By Thanksgiving of his freshman year, Billy already had a new mate on his arm. And I had occasionally asked in the intervening years about the whereabouts of the lovely Nina, but had never really gotten a straight or knowledgeable answer. I had heard somewhere that she had moved to New York, but that was the extent of my knowledge of her whereabouts.

"So are you living here now?" I quizzed.

"I am – down in the West Village. But I work up in this part of town."

Our conversation on the street corner covered all the bases in rapid succession: her college years, her move to New York upon graduation, her struggles finding work, her enrolling in graduate school and leading up to her landing a job in human resources at a large, reputable law firm.

As we talked, or as I listened to her, I admired this lady; just past the quarter century mark and at the peak of her beauty. She hadn't lost her knack for flirtation and as we talked she kept flashing her gorgeous smile and looking me up and down. She kept brushing her long brown hair out of huge dark eyes, better so that I could gaze upon her lovely face. Her eyes danced with wit and the excitement of youth and her lips were full and juicy.

She was dressed in typical upscale law firm attire, but the tight short skirt still hugged her exquisite rear end and the unbuttoned neck of her white blouse exposed the smooth skin of her slender neck and the slight swell of her lovely breasts. Her well manicured nails were on full display as she clutched her purse. The high heels gave her a few more inches in height, bringing her closer to my six foot plus frame and they also elongated her lean calves and gave her sexy stance a saucy air. Her legs were long, lithe, and lovely. I could feel my pulse racing as we talked.

"And how are you? What are you doing in the city?" she asked with an arched eyebrow.

I gave her an update on my recent past and she listened with keen interest. My work for a computer company had kept me climbing the corporate ladder and frequent trips to New York and other cities on the east coast had me spending a lot of time on the road.

As we talked I felt Nina's eyes roaming over my body. I was wearing a white buttoned down shirt, faded jeans and a blue blazer. Her half smile half leer told me she approved. I keep my six foot frame in shape by running and swimming and have been blessed with a full head of wavy brown hair and dark brown eyes.

"And you're not married?" she asked with a suggestive smile.

"Having too much fun being single, I guess. One of these days, I suppose. But I'm in no rush. Too many avenues still to explore," I explained.

"I can relate to that," she replied.

I was beginning to realize that we had been talking now for almost fifteen minutes and I either needed to let her go on her way or suggest a venue for continuing our dialogue

"Listen, Nina. You probably have plans or better things to do with yourself. But I'm heading back to my hotel – actually I was heading to the bar at my hotel – and if you'd like to accompany me, I'd be happy to buy you drink and catch up some more."

I eyed her quizzically to see if I'd overstepped my bounds or put her on the spot. I was expecting her to decline when she smiled, nodded her assent and cocked her eyebrows as if to say, "Which way?"

We proceeded up Madison Avenue, talking animatedly and finding we had a lot to talk about. I kept peppering her with questions, trying to keep her engaged and talking about herself. We arrived at the hotel and headed into the lobby and through to the bar; settling down at a cozy table for two in the corner. She ordered a white wine and I ordered a Gibson. We toasted to this unexpected reunion and smiled over the rims of our glasses.

Our conversation skipped from one topic to the next: sports, music, politics, travel. I continued to marvel at her innocent beauty and got lost in her deep gorgeous eyes. She oozed sex out of every pore, but in a disarming way that made one feel wanton and wholesome at the same time. What could my idiot brother possibly have been thinking to let this one slip out of his hands?

Another round of drinks arrived and our conversation turned to family.

"So you never told me what Billy's up to?" she asked as she took a swig of wine, her eyes dancing.

I explained his comings and goings; the trials and tribulations of his work and love life. Nina seemed thoroughly interested. I knew they had had a very close and intimate bond during their high school fling, and had seen them on more than one occasion having sex in our family room.

I'm not proud to admit to my voyeuristic ways during that period. But it had all happened rather unexpectedly.

As I mentioned I was home that summer after my first year in graduate school. I was working that summer for the company I eventually joined full-time and it was the first summer I'd been home in several years. Billy and Nina had been dating since the beginning of the summer and would usually spend Friday evenings at our house watching movies in the family room. I often wondered what they were doing during those long double features and one evening I found out.

I had been out with friends and had returned home around midnight. I knew Nina was over for the evening, so I decided to slip into the house quietly to see what these two were up to. I crept through the kitchen and headed for the bedroom wing, needing to pass the door to the family room along the way. As I approached the end of the hall I heard the TV, but I also heard some other noises. I slowed and wondered what I'd see if I peered around the corner.

The hall was dark and, while I was hidden from view, I could see clearly into the family room. As I peered around the corner I saw Billy and Nina – naked and fucking madly. This wasn't just any old casual fuck. Billy was sitting on the couch with his feet firmly planted and spread on the floor with his head against the back of the sofa. Nina was facing him with her back to me, straddling him, and riding him for all she was worth. Her hands rested on the top of the back of the couch as she kneeled above him. Her exquisite round ass was sliding back and forth on his long thick dick. I could see his girth stretching her labia and his cock glistened with her juices.

Though the TV drowned out their conversation, I could hear that she was talking to him, spurring him on, perhaps spurring herself on. I could hear them both moaning and breathing heavy,

Now I've been fucked this way and seen plenty of pornos of the same position. But Nina was moving her ass so provocatively and swiveling her hips in a sliding grinding pumping motion that was out of this world. My eyes widened as I watched and my cock thickened. I felt guilty, but I also felt hidden, so I pulled my cock out of my shorts and stroked along with their rhythm. I wanted to have my dick buried deep inside Nina's pussy. I wanted to be Billy – my lucky brother.

Both of them were moaning loudly now and increasing the pace of their fuck. Billy's hands were on Nina's ass, guiding her forward and pulling her sweet pussy onto his hard thick cock. I'd never seen Billy hard, but his dick was similar in size and shape to my own.

Nina was groaning loudly now and controlling the pace of their fuck. She was on a mission and there would be no denying her orgasm. I stroked with their rhythm and felt an eruption looming of my own. I folded my shirt over my cock and came just as Nina yelled and spasmed on Billy's prick. Billy came too, and as Nina pulled his glistening rod out of her gaping cunt, gobs of thick white cum drooled out of her pussy and onto his slick cock. It had to be one of the sexiest things I had ever witnessed and I felt privileged, lucky, and guilty to have seen such pleasure and seduction. I had to move on, but I lay in bed that night, stroking my thick cock and thinking about what had obviously been going on in our family room for some time.

A few weeks later on a Friday night, I again slipped into the house late one Friday night to see what I might find. I had been thinking about the scene I'd witnessed previously and couldn't get it out of my mind. As I crept down the hallway, I could again hear the soundtrack of a movie; but I could also hear the slurpy sounds of sloppy sex.

Billy was naked and prone on the couch. Nina, also naked, was crouched between his spread legs, sucking his cock with an abandon I would never have associated with her innocent looking exterior. Her right hand was wrapped around the base of his thick cock and her head bobbed up and down on his stiff long prick, gagging and groaning as she sucked and deep-throated him with an intensity I had only seen in videos. Her lovely breasts dangled and swayed with her sucking movements.

She groaned with desire and Billy's head was thrown back in a show of utter ecstasy as Nina made slow and deep love to his cock. She moaned loudly, communicating how much she wanted a load of thick white cum in her mouth. I could see the crescendo build and I watched in awe as Nina prepared herself to orally receive his semen. Billy arched his back, gave a loud yelp and came hard. I could only imagine what his eruption had felt like in Nina's mouth, but the gobs of white cum dripping out of her mouth and down his thickly veined muscle were a testament to another load deposited deep into her hungry mouth. She continued to gently stroke the base of his cock with the circle of her thumb and forefinger. She drooled his cum back onto his erection, then leaned down to lick it up again, running her luscious lips up and down his shaft. She had such amazing technique and was barely eighteen years old. I shook my head in amazement.

I went on to bed, tiptoeing toward my room, my cock hard from the scene I'd just witnessed. I stroked myself to an incredible orgasm that night while I fantasized about having Nina wrap her full lips around my shaft, sucking me just the way she had been sucking Billy. I was getting addicted to watching my brother and his girlfriend from the shadows. I was embarrassed and guilt-ridden by my voyeurism, but so turned on at the same time.

I did my best to resist being a fraternal voyeur and succeeded for several weeks in blocking out what was going on out in the family room when Nina was visiting for Friday night movies. But toward the end of the summer I couldn't resist one night and stealthily moved down the hall again to spy on the young couple. A soundtrack from another movie was clearly audible, but so was the sound of skin slapping skin.

I peeked around the corner and almost let out an audible gasp. Billy and Nina were on the floor. Nina was on her back, her hips raised up on some pillows. Billy was kneeling on his haunches, his prick buried deep in Nina's pussy. Her legs were spread wide and supported by Billy's arms. The angle and position of her raised pelvis allowed him to thrust in a powerful surge. They were both grunting as Billy drove his cock into Nina's cunt. Her breasts bounced unmercifully as he banged her hard; the wet skin at their junction producing a thick slapping sound. I was transfixed and hard as a rock. I stroked my own meat as I watched their youthful display of sexual abandon. What I wouldn't have given at that moment to be fucking Nina?

She rocked her head back and forth, her hair flying over her face as she screamed and came, her legs shaking in violent spasms. Billy continued his frantic pace, breathing hard, then pulled his cock out, and after a few strokes, spurted rope after rope of thick white cum onto Nina's stomach and breasts, a few spurts landing on her lips and jaw. I came into my tee shirt, cum running down my legs and onto the floor. I wiped it up quickly and padded back to bed, completely overcome with lust and desire for the teenage vixen laying freshly fucked on our family room floor.

So as I filled Nina in on Billy's life she looked at me with a faraway look, as if she was remembering those very evenings. I watched her closely for clues.

"Ah, sweet Billy. Those were good times," she exclaimed when I'd finished talking. "That was a magical time, senior year. It's too bad we couldn't keep things going. But that's life: he went his way and I went mine. C'est la vie. I'm glad to hear he's in a good relationship."

"He is, yes, he is. But you know, Nina? Of all the girlfriends he's had over the years, you were my favorite," I said seriously, gazing into her dark brown eyes.

"Oh, that's so sweet, Ben. Thank you," she replied with a sweet smile on her face. "You were my favorite older brother of all my boyfriends," she grinned in reply. "I always thought you were pretty cool, to be honest."

"I'm serious, Nina. Billy's had some damn cute girlfriends over the years. My bro does alright by the women. But you were, hands down, the most beautiful. - in my book, anyway. Billy's loss, I'm afraid."

Nina looked at me tenderly as I waxed poetic, a wistful smile on her face.

"Well I have very fond memories of that year, and your house. God we had some fun at your place," she said with a faraway look in her eye.

"I know," I said while watching her expression.

"You know what?" she asked with a lift of her eyebrow.

"I know you had fun at our house. It was hard not to....it was...well, I couldn't help but see you a few times."

"What?" Nina was honestly taken aback. "What do you mean you saw us a few times? Saw us doing what, exactly?"

She looked at me with a look of surprise and fear. The alcohol was loosening my tongue and I plowed ahead, damning the torpedoes.

"Well?" I paused for effect and looked her in the eye. "I saw you having sex."

A look of horror crossed her face.

"Oh, my God. Oh, Ben. I'm so embarrassed. I had no idea. How did you....? When did this....? Oh God." She put her hands over her face, then spread her fingers and looked at me with the cutest look; a mix of embarrassment and excitement.

"How many time? What were we doing? Oh, I'm so embarrassed."

She was embarrassed, but it was also quite evident that she was curious.

"Don't be, Nina. Honestly. I only saw you three times, to be exact. But it was probably one of the hottest things I've ever seen; watching you and Billy fuck. I'm the one who should be embarrassed, really. Lurking in the shadows on those Friday nights, watching you fuck him and suck him. Watching him fuck you so hard and deep. Watching him come all over your beautiful body."

My temperature was rising and I was beginning to get very turned on talking about this subject. I couldn't quite tell yet what effect it was having on Nina. But her initial embarrassment seemed to be waning as we pressed on about the topic. Perhaps I had overstepped my bounds and she would storm out of the bar, insulted by my verbal barrage. But she didn't.

"So, what exactly did you see us doing?" she asked with a wry smile. "And what were you doing while you were...watching?"

"Well, the first time I saw you I was coming home late at night and kind of crept into the house so as not to disturb you. I kind of figured you two might be getting it on, but, honestly, I had no idea what to expect. I heard noises in the family room and peeked around the corner. You two were on the couch. You were on top of him, kneeling, facing him, fucking him cowgirl. It was so hot: watching his big cock stretch your wet pussy. I couldn't believe the way you humped your hips back and forth, riding and grinding his cock. It was truly incredible. You were absolutely amazing."