My Night with Sophie

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Business trip to NYC connects boss and busty colleague.
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gapster7
gapster7
1,691 Followers

This story is about one incredible night I had five years ago in New York City. It is still hard for me to believe that evening unfolded the way it did, but it remains one of my most prized memories and a constant source of fantasy for me. This story is about Sophie.

My name is Steven. I own a commercial furniture company in Hartford, Connecticut and have lived a pretty straight-forward life over the years. I met Sophie for the first time when she came to interview for an interior design position in our sales and design division. She had responded to an ad we'd placed, her resume had been impressive, and I had called to bring her in for a face-to-face. She was employed at the time so we had to meet on a Saturday.

I was very pleased when she walked through the door. She was 5'-6" tall, had long, silky, dark blond hair, a sweet and very friendly face and a solid body. She wore glasses that afternoon, which I never saw her wear again. I guess she wore them for effect. She had tailored slacks, slight heels, and wore a fitted jacket that hugged her body. Even the several layers she wore couldn't hide that fact that she had some very nice curves.

She was of Baltic descent, but had grown up in Wisconsin and been educated there as well. Upon graduation she and her boyfriend moved east to follow a job offer for him. Sophie worked in a few firms in the area, but was looking for advancement and more money, so she had responded to our classified ad. She had married the same boyfriend, her childhood sweetheart I later found out, and they were looking to settle into the Hartford area and buy a house.

I was struck by her friendly nature and warm personality. She had a real "girl next door" quality and seemed like she'd make a great addition to our office. I offered her a position; she accepted and said she'd start in a few weeks after giving notice to her current employer. I was looking forward to her joining our staff.

And I was right -- she did fit right in. She had a warm bubbling personality that everyone gravitated toward and her charm and good nature made her an instant success with clients as well. Once she'd been in the office for a few weeks I came to appreciate what a lovely woman she was, particularly physically.

She had an open and expressive face and always had a smile. Her shoulders were broad, but tapered down to a very slender waist and a generously round rear end.

I loved to watch her hands. Her fingers were slender and she wore several silver rings. I often imagined her fingers wrapped gently around my cock, slowly stroking me. I also noticed how hairless her forearms were. I could only think that her pubis was crowned with downy hair. The thought never failed to make me hard.

But there were two physical attributes that stood out above all others: she had beautiful large brown eyes and absolutely incredible breasts.

Her eyes were the crowning touch of her beautiful face. "Blow job eyes" a friend of mine had called them, and I had to admit I did find myself fantasizing about watching my cock slide between her sweet pouty lips while she looked up at me with those gorgeous orbs.

Her breasts were undeniably magnificent. They were round, full and natural and I guessed them to be 36 D -- maybe even a DD. She always wore tops that accented their fullness, usually tight sweaters or clinging tops. Despite her seeming innocence, she knew she had an amazing asset and she was obviously proud of her tits and seemed very comfortable displaying them.

I loved to watch her walk across the office, seeing her breasts bounce tightly within the confines of her bra. I always figured her bras had their work cut out for them. She was good at what she did, and everyone liked working with her, but there was no doubt that her nice round boobs were adored by every male (and female) worker or client that came in contact with her.

I noticed every so often that her nipples would suddenly make their presence known, poking out proudly and on the very tips of her breasts. She had to know that her nipples were protruding through her tight sweaters, but she seemed almost oblivious to the fact that her glorious tits took on a whole new dimension when the nipples could be so clearly discerned. I tried not to stare during these fleeting occasions, but it took all my will power to keep from being a drooling fool.

Sophie and I began to work on a few accounts together and I always looked forward to our meetings or occasional trips out of the office to visit customers or make a sales call. I noticed over time that she had a very interesting habit, if you can call it such, that I found most intriguing. When talking with her she would often glance down at my crotch and then bring her focus back to my eyes. She did this quite often, especially when she was sitting at her office cubicle and I stood a few feet away talking about some business thing. She'd look me in the eye, then glance down at my crotch, then look me in the eye again.

I found this incredibly exciting and I could never put my finger on why that was. I didn't wear tight pants or clothing that would give away my own size, but she seemed to make these glances on a quite regular basis. It turned me on, I must say, and I fantasized and masturbated thinking about what she would be like in bed.

One Saturday I came into the office to catch up on some paperwork and Sophie was there working. I had dressed down, of course, and was wearing an old pair of tight jeans that were my typical Saturday apparel. This particular pair had fit to my torso over the years, and when seated my considerable bulge was wedged nicely into the crotch of my jeans. If Sophie paid a visit today, she would indeed get an eyeful. It excited me to think that she might actually get some indication of my own size and girth.

An hour after arriving I heard her clear her throat behind me. I swiveled in my chair and looked into her eyes. She asked a few questions about an account we were working on together, but after less than a minute talking I saw her glance down at my groin. I swore I saw her do a little double-take as she refocused her gaze looking directly at my face. We began a casual conversation as she perched on the conference table in my office. I would occasionally look away as we spoke and I could feel her gaze turn to my bulge. I'd look back and she'd quickly return her eyes to mine. I felt like I was playing a little game with her and the appearance of her stiff nipples through the very thin sweater she wore was a testament to the fact that I was right. I loved the fact that she was looking at me and probably wondering how big I really was. I stared at her beautiful round breasts and she stared at my considerable package and we each seemed content to let the other admire our wares.

But Sophie was recently married and I had been a faithful husband for 22 years so the game we were playing was just a form of flirting. But it turned me on, nevertheless, and I had a feeling that Sophie harbored a secret fascination and interest in my own endowments.

One day Sophie came to me to express an interest in attending Neocon in New York -- a furniture show that was the east coast showcase for commercial interiors. It's been discontinued since 9/11, but that year it was still going strong and was a huge show. I was planning on attending for a few days as I usually do and the fact that Sophie was interested was intriguing. She was very busy and really couldn't afford too many days out of the office, but she offered to attend just one day and, perhaps, we could cruise the aisles of the exposition together.

Sophie made plans to come down to New York a night early and stay with friends in the city. She'd meet me at the Javits Center and then take a train home at the end of the day. I was planning to stay another day for a few seminars. We confirmed out plans and I looked forward to spending some time with her outside the office.

I enjoyed my first day in New York, but I have to admit that I was really looking forward to having Sophie in the city. I arrived at the Javits the second morning and stood by the Hudson Newsstand at 10am as we had prearranged. I saw her striding across the sunlit lobby -- boobs bouncing, hair flouncing, she was a vision with a smile. We greeted one another with an innocent hug, got our badges and headed into the show.

We spent the morning weaving down the aisles, stopping to see vendors that we work with and checking out any interesting exhibits. Sophie was a shining light and garnered attention wherever she went. I especially enjoyed watching the faces of other conventioneers as we walked the aisles. Men and women alike looked at her as she walked by -- usually focusing on her breasts and then glancing quickly at her face. I loved the fact that she was with me.

Toward late morning we decided to catch an early lunch. We talked about innocent topics, but I did find out that her husband, Alan, was on a business trip in Texas and she was returning to an empty house on her return home. I filed that nugget away and thought about the possibilities.

We churned through the show in the early afternoon hours, but were only partially done as we hit a wall about 3:30. Sophie looked at her watch and frowned as she realized that she was going to have to think about heading to Grand Central to catch a train.

"Listen, Sophie, I have an idea. What's the rush in heading back? Why don't you stay tonight and you can catch a ride back with me tomorrow afternoon. I'm sure my hotel has rooms, this has been a very productive day, and it makes sense to see the rest of the show tomorrow after a good night's sleep." I hesitated. "And I'm your boss and I say it's okay."

She smiled and I could see her brain ticking.

"Well...I guess. I have a meeting tomorrow that I'd have to reschedule." She looked at me quizzically.

"Then call the office and reschedule. This is a great show and it's great having you here to share it with. But I'm exhausted and I think we ought to head over to the hotel, get you settled and then go out and have a nice dinner. What do you say?"

Her smile said it all. She called the office, dispensed with her morning responsibilities and we headed out of the convention center to catch a cab. I was staying at the Intercontinental on the east side. I usually like to avoid the convention hotels in Times Square and make it a point to find a nice hotel off the convention trail. Our cab dropped us off on 48th Street and we headed into the lobby. I had called ahead and confirmed that a nice room would be waiting for Sophie. She checked in and we went our separate ways with plans to meet down in the bar around 5pm.

I was beside myself with excitement. I went upstairs, shaved, showered, changed clothes and got ready for an evening of who knew what? The unknown quality of what lay ahead was what really got my blood flowing. I headed down to the bar, ordered a Grey Goose with lime on the rocks, and waited for Sophie to arrive. She slinked in a few minutes later. She had changed her clothes and looked stunning.

She had on a fitted pair of black slacks, molded to her round rear end, a pair of nice black heels and a baby blue cashmere sweater that hugged and accentuated her killer curves. A little make-up, a hint of perfume, and a big smile -- I ordered her a drink. We settled in to relax and talk a bit over a pre-dinner cocktail, forgetting shop and concentrating on more personal matters.

I began to ask about her background and upbringing. We sat across from one another on a settee and I knew that the pair of slacks I had worn was hugging my crotch very tightly. As we talked I saw her glance down at my cock several times -- just doing what she did naturally. A stiff drink fueled our conversation and before long I was asking about her marriage and relationship with Alan. Apparently they had been junior high and high school sweethearts, and while they had gone to different colleges, their relationship had continued through their college years and beyond.

"So is Alan pretty much the only guy you've ever been with?" I asked, suddenly regretting such a personal question.

"Well, yeah, I guess. I mean, I went on dates with other guys, but...well, Alan is the only guy I've...you know." She seemed embarrassed at this announcement and I made some lame comment about how great it was and tried to change the subject. But she had other things in mind.

"Well, what about you? When did you meet your wife?" I gave the sixty second version of my married life, how we met and so on, but she continued this line of questioning.

"So did you have a lot of girlfriends before you met your wife?" she asked.

"Well, I guess so. I mean, I'm married and faithful now, but before that it was a bit crazy. Especially in college."

Her eyes widened and she pressed on.

"What about college?"

"Well it wasn't all of college -- mostly my junior year actually. That was a pretty incredible year."

"How so?"

She wasn't letting go of the topic, she seemed quite curious, in fact, so I decided to elaborate.

"Well two things happened my junior year. First I joined a band. I was the lead singer and guitar player in the big band on campus. We played several nights a week at parties and clubs and wherever we could. And even though Ann Arbor is a pretty small town in the scheme of things, if you're a happening band, then there are going to be plenty of girls around. And there were."

"And what was the second thing?"

I hesitated and then plowed ahead.

"Well early in the year I went out on a couple dates with this sorority chick, Bethany. She was very social and very well-connected. We hooked up, but it wasn't going anywhere. Anyway, she had a big mouth and she began to circulate a rumor about me."

"Which was?"

"Well, it's a little embarrassing to talk about, but, well, she began to tell all her girlfriends that I was...well, that I was really well-hung. I can't tell you the number of girls I met that year who had heard that from Bethany or a friend of Bethany's. Anyway, it was a rumor that took on a life of its own."

"And was it true?"

I blushed a little, but I could see Sophie eyeing my cock again.

"Well, yes, if you want me to be truthful. Or so I've been told, anyway."

I looked at Sophie closely and could see her face flush with excitement. I could also detect her nipples gently prodding the soft this material of her sweater. I decided to push ahead.

"You know, it was a weird year. I decided early on that I wasn't going to get involved with anyone seriously that year. I was going to enjoy the variety and sheer number of women that came my way and I was going to...well, I was just going to enjoy it. I figured it was a once in a lifetime kind of thing."

Sophie smiled and I could tell she was very interested in learning more.

"So how many girls did you sleep with that year?"

"I really don't know. I didn't count exactly. But it had to be north of fifty."

Sophie blanched.

"My God. You're kidding me? What was that like?"

"Oh man, I'm so embarrassed..." I shook my head in mock shame.

"Oh don't be embarrassed. I think it's amazing. I just want to know what it was like being with so many different women."

"You know, it's weird, but at times I got the feeling like I was a sex object. I know that sounds weird or conceited or something. But there were a few women that came onto me and only wanted to see my cock. I mean, they were like curiosity hounds or something, and they...I mean all they wanted to do was look at it. It was totally bizarre"

I wasn't sure where I was going with this and I didn't want to turn Sophie off. I waited to hear her press the conversation.

"What did they want?"

"Well some of them just wanted to look at me and touch me. And some wanted to, you know, suck me. I was clearly too big for a few of them. But some of them really got off on my size and, well, that's what made the whole thing worthwhile."

I looked at Sophie and smiled. She kept doing her gaze thing -- she'd look down at my crotch and then look back in my eyes. The drink was loosening her inhibitions a bit, and she was slowly becoming animated.

"So you were too big for some of them -- what about the others?" she asked with a wicked grin.

"Well there were actually quite a few that really got off on my size. And I like to think that, you know, I had more than size going for me. Like I said, it was an incredible year and I learned a lot about pleasing women. It was worth the price of tuition, you might say."

Sophie had a glazed look in her eye. She continued.

"Well, I'm embarrassed to say that the only penis I've ever seen is Alan's. I really don't have anything to compare it to."

She glanced down at my crotch again. I had hardened slightly with all this talk about sex, and I knew she was getting an eyeful, even though I was fully clothed. The alcohol had fueled this conversation so far and I felt like it was time to make a bold move.

"Sophie, I have to say something. I feel like we are being given this special night and we have an opportunity to take advantage of this situation. I know you're recently married and I'm married 22 years, but I have an idea if you don't mind my continuing?"

She looked at me with a wistful gaze, a little suspicious, but more curious than anything.

"Please do," she stated.

"I can't help noticing how you have a habit of looking at my crotch all the time,"

Sophie blushed with embarrassment and looked away from me. I didn't want to turn her off.

"Don't get me wrong. It's quite flattering. But I've noticed many times, not just today. And I, well, it's hard to put into words, but..."

I hesitated before going on, but it was now or never.

"Well here's what I think we should do. We are going to go upstairs to my room. I have two double beds. You are going to get on one -- I'm going to get on the other. We are not going to touch. I'm going to take my clothes off and you're going to take your clothes off. I'm going to show you my cock. I'm going to make it hard for you. And then I'm going to jack off for you and I'm going to show how much cum I can shoot out of my stiff cock when I'm really excited. It's going to blow you away."

I looked at her earnestly and could see that she wasn't quashing the idea. She seemed intrigued.

"And you are going to show me your magnificent body. Sophie, I can't tell you how amazing I think your body is. In fact I've jerked off thinking about you so many times, it's not even funny."

This seemed to excite her.

"You have? Really? I can't believe it?"

"Oh, believe it, Sophie. Many times. I've thought about what it would be like to bury my dick deep inside your pussy. I've thought about what your beautiful eyes would look like when you were trying to swallow my penis. I've thought about sliding my cock between your big tits. God, you're lovely."

Sophie looked at me incredulously. Maybe I had blown this. Maybe I had totally misread the situation. But I saw her gently rub her nipple and I knew that she was hooking onto the idea. I decided to continue.

"So we're not going to touch one another. You'll be on one bed; I'll be on the other. We'll talk and fantasize, but we won't touch. What do you say?"

I looked at her with lust and hope. Sophie swigged down the remainder of her drink and placed it squarely on the cocktail table.

"I say let's go."

She stood up and her breasts bounced ever so slightly with her movement. Her nipples were protruding proudly through the cashmere. I paid the bill and we slowly sauntered out of the bar and back into the hotel lobby.

We wandered toward the elevator, already feeling a bit uncomfortable with the "no touching" limit I'd suggested. I felt like I needed to lead the way and I wanted to start this session, wherever it might lead, by playing by the rules. We took the elevator up to my floor and just looked at one another across the elevator cab. I could feel her pull, but I resisted.

gapster7
gapster7
1,691 Followers