This story is a collaborative effort with Kinkycanucks. Please checkout their stories and I know they have more in the works. It is based upon some true events with some fantasies mixed in.
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Jack was a single guy in his late 20's who was coming off a bad relationship. A friend of his was trying to play matchmaker because she thought Jack was wasting his time and could attract a great woman if he was a little more confident.
"Come on Jack, you have to get back in the game. You have everything going for you, good looks and success," his friend said.
The woman his friend invited to meet was nice but Jack wasn't the least bit interested, however one of the other guests caught his attention. He noticed a cute, tall blonde across the room and was immediately attracted to her. She looked much younger than him but he couldn't take his eyes off of her. She noticed him looking at her, smiled a bit and continued talking to another man who appeared closer to her age. Jack noticed her pert breasts in her satin tank top and her ass filled the black leggings she was wearing. He was finding himself staring at her more and more, noticing every detail down to her mannerisms during her conversation. She had a style about her, her slight head tilt when she was listening more intently to the small dimples when she smiled. He even saw the exact moment when the other man lost her attention, her reaction was a deep breath with raised eyebrows and then a tight lipped smile.
The young woman must have sensed that Jack kept looking, her soft blue eyes met his big brown eyes a few times and there was a spark. The game continued, sometimes they would pretend not to notice that the other was looking and sometimes they would simply exchange a casual smile. It was like they were having a silent conversation. She was intrigued by the man watching all the way from across the room, he was handsome, sophisticated looking which set him apart from most of the guys at the party. She liked how he was dressed too, casual but yet stylish in his dark blue jeans and patterned long sleeved shirt which was untucked. She also appreciated his clean cut look, freshly shaved and hair neatly brushed.
Even as the tension built between them Jack still thought the lovely young lady was much too young for him and probably out of his league. Again it was his lack of confidence preventing him from realizing at six feet tall, in good shape (185 pounds) and a full head of dark brown hair he was quite a catch.
Suddenly seeing the object of his fascination standing by herself and emboldened by a few drinks, Jack summoned up all his courage, deciding to go over and speak with her. Worst case scenario he was only trying to be friendly, nothing more or so he told himself. He was greeted with a big smile that was warm and inviting, she introduced herself as Melissa. He quickly learned she was working as a server and part time bartender at a local establishment Jack had never heard of. Jack and Melissa immediately hit it off and found themselves huddled in a corner of the living room talking without any concern for the rest of the guests.
Jack was much different from the guys Melissa was used to. He was more mature and she found his boring stable job as an accountant to be refreshing. She also found him to be charming and witty. The other men her age were unsure of where they were going in life and quite frankly, could be real jerks at times. Jack was different, she gladly gave him her phone number at the end of the night figuring it was worth the chance to try dating someone like him.
Melissa left with a friend at the end of the night who had noticed the extended conversation with Jack. She confirmed to her friend that she really liked Jack and hoped he would call. Much to her delight Jack called her moments after she made it home. Normally he would have waited but something made him reach out and his instincts were right, Melissa had excitement in her voice and was ready to take a leap of faith. It was just after midnight and he had talked her into meeting at a local pub near her place for a nightcap.
Their first date would be just hours after meeting at the party. They talked for the next two hours until the bartender announced last call. Jack and Melissa held hands as they walked back to her apartment and made plans to meet for dinner the very next night. At the doorstep of her building there was an awkward moment of uncertainty, both of them were trying their best not to turn off the other by seeming too pushy or desperate. Simultaneously, they leaned forward giving each other a good night kiss. This would be something over the years Melissa and Jack playfully argued about, who initiated the first kiss? One thing they couldn't dispute was how that first light kiss turned into a much deeper one, then turned into a short makeout session on the street.
The next day had them both waiting anxiously. When Jack arrived and pressed the buzzer his heart pounded in his chest and when Melissa appeared and opened the door it almost stopped. He couldn't get over her long legs and they looked amazing in a very short, tight jean skirt. Jack also appreciated the cami top that revealed some nice cleavage. The entire package was virtually perfect, her hair was flawless, nails freshly painted and again her legs caught his attention thanks to her four inch heels. He walked her to the car and acted like a true gentleman by holding the door open for her as she climbed inside. Melissa was trying her best to be ladylike but it wasn't completely possible with what she was wearing. She had one leg on the ground as she placed her left leg inside the car, her legs spread open giving Jack a clear view up her skirt to her powder blue bikini panties. She knew he was catching a bit of a glimpse so looked away feeling the warm blush of her cheeks. Jack on the other hand didn't turn away, instead hoping for a better view of those legs and a peek at her panties was the universe's way of giving him a reward for being a gentleman.
His chivalry continued at the restaurant, Jack ran around to open the door for Melissa again. She was happy, no other guy had treated her like that before and again in the restaurant he pulled out her chair. He was succeeding in impressing her.