Classic Cocktease by an Ex

Author's note-This story is about 90% true, there are a few added details to make it easier to read, but this is pretty much how it happened.

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We were a couple for almost a year, both of us mid to late twenties working for a nationwide retail specialty store chain. It was a fun and busy time in my life, I was living in Manhattan and enjoying being a single guy in an industry dominated by very fashionable women. She was a district manager of a few stores over the bridge in New Jersey. We met at a company annual sales convention, she was quite flattered by the attentions of senior buyer for the chain at the opening night cocktail reception, I was quite intrigued by her incredible strawberry blonde hair and thin, shapely figure. We ended up in my hotel room bed that first night.

Pretty much everyone thought Kim and I were an odd couple. I was tall (6'2") and had a thin athletic frame, with a preppy Irish look to me. I wore Brooks Brothers suits with tassle loafers and came from a prestigious northeastern university. I liked my preppy aloof image, I liked it a lot. I was in to sailing, theater, collecting wine, playing golf...I loved the NYC restaurant scene. I was just one huge stereotype right out of the preppy handbook, and in retrospect was pretty impressed with myself.

Kim couldn't have been more different. Kim was sincere and very kind, she loved animals and small children and was close to her family. She had grown up just south of the Mason Dixon line, and had worked hard to get through a two year community college. She was smarter than she thought she was, she had good street smarts. But she was what she was, a pleasant girl who was more impressed by nice cars and a good chain restaurant than fine wine and the theater. But, what Kim did have was a great body. About 5'6", the beautiful hair was about shoulder length, on a slender frame with a great pair of 34B tits. They sat up high and proud, with a set of beautiful smallish pink nipples that stiffened oh so nicely. She had a gorgeously shaped ass that she preferred to keep tightly encased in a pair of broken in jeans. Kim had a narrow face that was average, not one you would pick out in a crowd, but oh, that body.

The night we met was a crowded gathering, and almost everyone there knew only three or four people from their local sales region, and pretty much stuck together. Kim and I had struck up an easy rapport over the phone in my year with the company, though we had never met in person. One of my assistant buyers had pointed her out early in the evening in the midst of the 'Jersey girls' as we referred to the store management team in her district. I spent the early part of the evening working my way through the room, introducing myself around and enjoying the deference and fawning that was standard from store personal for senior managers from headquarters, but purposely starting at the opposite side of the reception from Kim's group. When I noticed most of Kim's group of girls duck out to the outdoor patio smoking area I adjusted course.

I introduced myself to Kim with a feigned ignorance of who she was, and acted convincingly surprised that it was her, that we finally met after only talking on the phone. She smiled warmly if a bit nervously, saying she everyone knows who I am. We were only able to chat for a few minutes before her entourage returned from the patio and she did introductions all around. I made an excuse that I needed to meet some more people before the reception ended, but made a point of asking Kim in my most professional tone if we could catch up again before the evening was done to discuss a few things.

The reception ended about an hour later, and the crowd dispersed pretty quickly as most of the crowd was pretty anxious to get out in to the Manhattan night with what little spare time they would have that week. I was caught up in conversation in the emptying ballroom with one of the buyers who worked for me, but could see Kim lingering at a distance waiting for me to be free. I dragged out the conversation a bit, making her wait. Finally we finished up, and I made a bit of process of gathering some of my things. Kim made a cautious path to me and asked if I still needed to speak to her. I acted as if I had forgotten, but was gracious in thanking her for reminding me, and suggested we move to the gorgeous piano bar for a glass of wine while we talked. Two glasses of wine later Kim was following me back to my room.

Kim and I had a pleasant relationship in the time we were together. She was very nice, and doted on me when we saw each other. We both loved to ski, in hindsight that common interest made our relationship last about twice as long as it really should have. Our relationship was pretty much restricted to weekends by the distance between her central New Jersey home and my Manhattan apartment. So my week nights were free to chase the ultra fashionable, prep school city girls that always caught my eye. I think you know the type...tall, stick thin with perfect straight hair, small boobs and a credit card balance at every fashionable store in the city. But mostly what kept us together, at least from my perspective, was the sex. Kim had an absolute killer body, but she coupled that with being an insatiable athlete in the bedroom. She was creative and totally uninhibited, and could go for hours. She loved to try many different positions, could give a world class blowjob, and was ready, willing and able 24/ 7. She loved to please, and knew her body could give a man intense pleasure. She would playfully pout when I begged off, saying I just couldn't go a third or fourth time, and was sore and chafed by Monday morning from a full weekend of multiple times per day screwing. Kim knew she was great in bed, but her humble nature would never let her think to use that to her advantage outside the bedroom, in her mind that is just what her partner deserved. Even after our relationship was winding down, we never really had a singular breakup moment, I went back for more several times even though I knew I was using her and she deserved better.

Ten years later Kim and I had long since moved on with our lives. I had moved away shortly after we broke up, and eventually she met her future husband and moved as well. My career had taken off, and I was regularly criss crossing the country for work. I really didn't even think of her very often, though my memory of her was that she had been an aberration in my dating history. I thought of her warmly because she was such a nice person, but she wasn't very sophisticated. She liked her jeans with heels, couldn't debate world politics, and preferred rum and coke to a nice Pinot Noir. But mostly she was a distant memory.

My flight from the West Coast got me home very late, and pretty worn out. I felt rumpled and tired and dropped my garment bag just inside the door. My mail was in a pile, and I punched the message button as I sorted junk mail from bills. The first two messages where family and friends, but message three caught my ear, stopped me cold.

'Hi Skip. I'm sure this message will surprise you, probably shock you. It's Kim, I hope your remember me. A friend of mine was showing me how you can find people anywhere in the world on the internet, so for laughs I typed in your name. It gave me an address and this phone number, so I called it. I promise I would have hung up if a woman answered. If you feel like it call me at xxx-xxx-xxxx or you can email me at........'

I played the message back three times, there was no mistaking Kim's voice with her slight Southern drawl. I scribbled down the phone number and email address, finished sorting my mail and pulled out my laptop. Too tired to think only moments before, Kim's voice intrigued me enough to open my email. I typed out a quick email to her telling how pleasantly surprised I was to hear from her. I gave her a quick rundown of my last ten years and asked her to catch me up on her life, and I hit send. While Kim had been put away in a distant part of my memory, I have to confess that her voice brought her back quite vividly. That night I thought back to her perfect twenty something body and incredible bedroom skills with my hand firmly wrapped around my hard cock, then repeated the process the next morning. Both sessions resulted in powerful orgasms, which I enjoyed immensely. I made a mental note to listen to her message again that night.

My morning email inbox had a few messages, but one jumped out. Kim's rather cryptic email handle was followed by a subject line of 'Hey Sexy'. All other emails took a backseat, as I looked forward to finding out what path Kim's life had taken since we parted. I hoped she didn't have any bitter feeling lingering from our relationship, I really hadn't treated her very well at the end, and hoped things had turned out well for her. Kim sent a very nice note. She talked about her life in the Orlando area, how she enjoyed the warm weather and friendly people. She was married, though she alluded to that part not going very well. She didn't seem surprised at all that I was working too much, but doing very well. But mostly she just seemed to enjoy hearing from me.

We exchanged a few more friendly emails, pretty quickly reverting to the good natured ribbing we both enjoyed back in the day, it was as if we had been apart for a month, not ten years. I mentioned that Orlando was an occasional business destination for me, and in fact would be there the following month. Would she be interested in dinner for old times sake? Kim was delighted by the idea. She said she would pick a restaurant, it was her home town, and to forward my hotel so she could pick me up. It was date.

A month later I arrived in Orlando. My days on these trips are very busy, local management tries to fit as much in to my day as possible. I did manage to beg off from the standard dinner meeting, saying I had a previous engagement, though a playful eyebrow was raised when an administrator came in to a meeting to say I had a phone call from woman who wanted to confirm for the evening. I made an easy recovery, saying I had an old college friend who lived locally as I slipped out to take the call.

For the first time in ten years I heard Kim's voice live. She laughed when I scolded her for the message she gave the admin, saying she thought about saying she was my hot date for the evening. I thanked her for her incredible discretion. She confirmed my hotel and the time, and we both said we were looking forward to it. I was surprised and amused that just her voice had caused a significant reaction in my briefs, I was half hard as I slipped back in to my meeting, and was thinking that tonight might be more about the good old days than I had planned. My meetings wrapped up early, and one of the junior marketing people brought me back to my hotel. I had an hour to get ready to see Kim, so I pulled out my laptop to scan my email. My inbox showed a new email from her, with an enclosure. Intrigued, I opened it. 'Can't wait to see you, thought I would send this along in case you forgot what I look like. There are a couple more pounds today, but I still look ok.' I opened the enclosed photo, and my jaw dropped. It was a bikini picture from one of our beach trips years ago. Kim was leaning in to the camera at a side angle, and her lean body looked incredible, with the lens looking in to her well displayed breasts. I just stared for a few moments, and had to resist the temptation to stroke myself stiff cock. I headed for the shower, enjoying her slow seduction of me and looking forward to a great night. I had already made sure the nightstand was stocked with condoms, though I hoped our past would give me rights to leave them in the drawer.

My hotel room phone rang about 5 minutes early. When I answered the unmistakable voice said only 'Are you decent?'.

I was more than ready for her provocative question. 'Do you want me to be?'

'Don't start something you can't finish sweetheart, do you want dinner or not? I'm in the lobby.' she purred back to me.

I told her I would be right down, grabbed the room key and headed for the elevator. When I got to the lobby I could see Kim on the far end of the room. She was back to me, so I stopped to silently appraise the effect of ten years. From the back her tight jeans did show a few more pounds, not unpleasant at all, but not the same view I remembered when she was 26. The red blonde hair was still striking, a little shorter, but beautiful. A cotton sleeveless sweater went well with the hair and jeans. I made my way quietly across the lobby, and finally spoke up. 'Did you make a deal with the devil?' Kim spun around, but looked confused by my question, so I clarified. 'You haven't changed at all.' I fibbed.

When Kim spun around I got my first surprise of the evening. Kim's cotton sweater was snug, very snug, and it stretched across a bustline that was clearly different from my memory. The very nice, perky B cups of 10 years ago had transformed in to full set of at least C cup breasts today. The tight sweater, and Kim's still thin frame, created a traffic stopping sight. I couldn't help but briefly stare, and I thought I saw a wry slight smile that made me think Kim had caught me. But I tried my best to recover, pick up my jaw and smile. Kim smiled broadly and took two steps and gave me a bear hug, her large breasts crushed against my chest. She took my head in her hands and gave me a big kiss on the lips and blurted out 'It's sooooo good to see you.' I had to agree, though I would have liked that bear hug with those big breasts to have lasted a little longer.

Kim asked quickly about my trip down and my day of long boring meetings, but then grabbed my hand and pulled me toward the door. 'C'mon, lets get some good food and really good wine. You can pick the wine...'

We walked out to Kim's car and climbed in some kind of American sports car which made it clear she still hadn't outgrown her love of muscle cars. I stole glances at her incredible rack thoughout the walk across the parking lot. Kim pulled out of the hotel lot and we headed down the local highway as she chattered away. Kim talked mostly about life in greater Orlando, a land of strip malls and every restaurant chain she needed. She loved the affordable cost of living, and how easy it was to find work. I feigned interest and agreement, while focusing on the side profile of her boobs. She made some mention of a local Italian place, joking that she knew I wouldn't want a restaurant you can find just anywhere, and laughed about it being a little pricey but she knew I was picking up the tab. Right now that dinner tab was looking like a real good investment. I am not sure if I talked at all during the short drive, but Kim's chatter had us more than covered.

We arrived at the restaurant parking lot. I made a point of putting my hand on the small of her back was we walked in, Kim didn't make any attempt to move away. The restaurant was kind of old school, lots of fake grapes and chanti bottles holding candles on the table. A gracious maitre'd welcomed us warmly and discussed our seating preferences, staring at Kim's bulging sweater the entire time. I couldn't blame him. He showed us to a table against a side wall and introduced our waitress. Wine lists were found, and I ordered a bottle of easy to drink merlot. The bottle arrived almost immediately.

Dinner was very pleasant. The wine flowed, and I truly enjoyed sharing the last 10 years of lifes twists and turns with each other. Kim was very relaxed and laughed easily. At one point mid-way through dinner Kim was talking about how she had gone through several jobs in her time in Florida, when she reached across the table. She lifted my chin and scolded...'My eyes are up here.' Her smile had a different aura to it, like she enjoyed the attention but with a tiny evil twist. I had been busted, but made no apology. Dinner progressed with some light and flirtatious touching across the table, evolving to a little bit of foot play under the table. The wine, the touching, and the straining sweater were taking their toll. I was more than half hard through most of dinner.

Dinner finished, and our waitress asked about coffee or dessert. Cappuccino, an after dinner drink? Kim gazed across the table and slowly licked her lips. I went fully hard as a vivid memory of her incredible blowjobs returned full force. I opened my mouth and groaned very quietly. Kim knew the effect she was having on me. She didn't break our gaze as she spoke to the waitress. 'He will take the check now...' As the waitress hurried off Kim leaned across the table, crushing her breasts in to the tabletop and giving me a view down her sweater. The view sent a healthy flow of pre-cum in to my underwear, and I visibly shifted to find a more comfortable position for my rock hard cock. Kim stage whispered to me as she reached and ran her nails down my forearm.. 'I think we would both rather be somewhere else right now...' My breathing was a bit ragged.

The check came and I hurriedly paid it. I got up from the table to let Kim out, putting my tented slacks eye level to her. Rather than getting up, she pointedly stared. 'Oh my. Did I do that? Are you ok to walk with that thing?' she asked, causing me to blush deeply. She slowly slid out of her seat, then stood gathering herself as I continued to stare at her breasts. When she hadn't moved I finally pulled my eyes away only to find her looking right at me. 'I know they're nice, but they need us to give them the table...' she said as she gave me playful push toward the door. It was hard to miss the eyes of the guys, and a few women, who followed Kim out the door. At least a few gave me the look...the combination of resentment and lucky bastard in one look. Maybe it was my imagination, but the very pretty young hostess seemed to looked directly at my tented trousers, then up at me with a sly smile.

Kim and I held hands across the parking lot. When we got to the car I couldn't hold back any longer. I spun her around and pressed her against the car. I grabbed the side of her head and leaned in to her as I kissed her with a hungry passion. Our bodies pressed fiercely together, her breasts and crotch ground in to me. We kept this up for a full two minutes or so. Kim bit down with passion on my lower lip, then leaned forward to my left ear. 'Lets get a room' she rasped in to my ear as her right hand reached down and firmly gripped my stiff cock. She gave me a couple of firm strokes, then pushed me back. 'Get in the car before we get arrested out here...'

The drive back to my hotel was a blur. Kim drove the short distance in silence, I couldn't help noticing how the shoulder belt disappeared in to the canyon of her cleavage. In fact I just stared, I was so far beyond hiding it at this point. Kim pulled in the lot but instead of pulling in to a space she pulled to the front door. I turned to her puzzled, she just gave me a sly smile. 'Thanks for dinner.' Kim just gave me a long painful pause, then finally spoke. 'Are you going to invite me in, or do I just get a quick kiss goodnight?'

I laughed a little awkwardly, I was so turned on my sense of humor was kind of shut down. 'God yes, please come in.' I said a bit too desperately. Kim smiled a small evil smile, and put the car back in to Drive. We parked and walked back to the hotel entrance, it was all I could do not to start groping her on the walk across the parking lot. The bursting sweater had what I am sure was its desired effect, I couldn't wait to get Kim's bra on my hotel room floor. Finally we made it upstairs to my room.

Kim walked and in and flipped her bag down on a table. The room was very nice, I had upgraded both the hotel and the room from my normal travel hotel standards, and was fairly sure she had never been a hotel room this nice before. I was absolutely sure I had never been in a hotel room with a woman that I wanted this badly before. Kim kicked off her shoes, and flopped down on the sofa. 'Is there a mini bar in this place?' she asked.