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.
Dinner was excellent and there was an instant connection, they shared a bottle of wine as they ate the best Italian food around. After dinner they checked out a band playing at a nearby club but quickly, Melissa mentioned that they weren't good and Jack agreed. There was a sexual tension building between them throughout the date and Jack decided to push the envelope by asking Melissa to go back to his place to watch a movie. Melissa was surprised by the invitation, she didn't want to seem easy but she was also feeling turned on, so accepted. After a short ride back to Jack's they shared some more wine as they watched the movie. It wasn't very memorable for Melissa, she was distracted, and they turned to making out on the sofa.
After some passionate kissing and touching Melissa found herself naked in his bed watching him strip off his clothes. Things moved rapidly; he had a nice body and an average size penis which made her want him. Jack scanned her body while climbing onto the bed. He started at her breasts which were 34B in size, they were shaped perfectly with small pink nipples which were already hard as buttons. Her tummy was flat and smooth and she was neatly trimmed between her legs. She looked even better than he imagined which was saying something.
They kissed and fondled each other's naked bodies until Jack moved down to eat her pussy. Melissa could tell he knew how to please a woman because of his expert like oral skills that quickly brought her to two orgasms. She returned the favor by moving down and sucking his cock. When Jack finally entered Melissa's pussy, he started out making soft, gentle love to her, slowly moving his dick in and out. As he picked up the pace the hotter she got. Soon he was fucking her fast and furious. He turned her over and fucked her from behind hard, their bodies slapping together loudly as they both moaned and grunted passionately. Melissa was trying to control her audible outbursts of pleasure trying not to appear slutty but the intensity of their sex made that impossible. She came again followed quickly by Jack erupting deep inside her.
Melissa spent the night at Jack's place waking up to the smell of bacon frying as he cooked her breakfast. She came out of the bedroom wearing one of his white dress shirts that showed off her firm legs and allowed her nipples to show through. It was difficult for Jack to keep his eyes off of her throughout breakfast. She ate slowly enjoying each bite and delighted in the desire building between them. She kept smiling knowing where they were going to find themselves soon enough. Jack took charge as soon as he saw the last piece of bacon lifted from the plate and placed into her mouth, he scooped her up from the chair, tossed her over his shoulder and carried her off to the bedroom.
Unlike the night before they immediately had very heated, passionate sex to the point they were both struggling for air and sweating profusely from their efforts. They couldn't get enough of each other. Jack pounded Melissa's pussy hard and she responded by begging for him to fuck her harder and faster. He did what she wanted until he had to slow down to catch his breath though never stopping his thrusts deep inside her. Sensing he needed a break Melissa got on top of him and rode his cock allowing him to play and suck on her perfect, luscious breasts.
Jack looked up at Melissa while she was bouncing on top of him, he couldn't believe that a woman as beautiful as her would end up in his bed. They kissed and carried on as they screwed in a variety of positions ending with Melissa on all fours; this was their favorite. In this position Jack had perfect access to her round ass. He could feel and squeeze her cheeks while driving deep into her, it felt almost primal. He wanted to take her anally as he stared down at her other entrance but she refused, not wanting to do that. Jack understood and was happy to continue his assault on her pussy until they finally came in a raging mutual orgasm.
From that day forward Jack and Melissa were inseparable as a couple. Their sex life was the hottest it had ever been. It was the kind of raw animal sex you have at the beginning of a hot relationship. They couldn't keep their hands off one another and were having sex as often as possible, sometimes multiple times per day. They were fucking in a variety of places and continued to try new positions but Melissa just wouldn't agree to anal sex no matter how much Jack asked, begged and pleaded.
