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The Lucky Girl
It began innocently enough at work. But Michael Angelo lived by the motto of never shitting where he ate, especially when he was the boss. There lying in wait was too much potential drama for such a small indiscretion that could ultimately ruin his career. Who knows why she teased him so. Perhaps she saw his position and income as a source of security. He was old enough to be her dad. Perhaps she had daddy issues or fantasized about fucking the boss. Whatever motivated her, he never openly responded, though his inner cock always grew rock hard. He’d simply smile at her, perhaps shake his head, and wonder how he would have to touch her to make her beautiful eyes dance and her highly kissable lips moan softly.
This all changed when he had abruptly quit. He was simply tired of being the boss man which had increasingly meant being the bad guy. Once he had released himself from those bonds, all the pent-up fantasies began flooding into his mind. And you better believe there were a lot of fantasies about a lot of young women he had worked with over the years, enough to write a few volumes of erotic short stories. And sure, he could write about his desires till his fingers bled, but what he really wanted was to live them out.
This was tricky because most of the women whom he entertained dirty thoughts about only knew the outward squeaky-clean veneer he had established out a sense of professionalism. Many would be appalled and dismissive. Most would find him a disgusting, dirty old man. However, truth be told, Michael Angelo had always been more bohemian than businessman. In his mind’s eye, he never viewed himself in terms of being a certain age at any point in his life.
In fact, he always found it strange when friends would dread reaching a certain number of years of living because he was always focused on how to make being alive more interesting. Focusing on age was too linear for him. He had long ago rejected that becoming a mature adult was a simple matter of following sequential steps towards happiness. For him, real happiness and pure joy were much more intangible than being in a certain station in life at a particular moment on a timeline. But more often than not, he found himself alone in these ideas.
He thought a long time about who he might want to make the lucky girl. While it might be someone who was currently in a relationship he’d most likely be rebuffed out of hand. He did not believe any of the potential candidates were involved in the swinging lifestyle and jealous boyfriends and husbands could mean real trouble in this town. Finding a single girl severely narrowed field. That’s when he remembered her. Actually he had never forgotten her. However, the few times he had openly flirted with her since leaving the job, she had generally been smitten with someone else and pursuing opportunities. Besides he was never completely convinced he was ‘relationship’ material anyway. They had become friends on Facebook and he had followed the trials and tribulations of her love life from across cyberspace. Occasionally they ran into one another shopping for groceries and each time she had the same effect on him; rock hard inner cock.
This got him to thinking and he began to consider her viability. One potential issue was that she was a diehard romantic looking for someone to sweep her off her feet with wine and roses and chocolate. He was far less romantically inclined, simply hoping to find someone to develop a longstanding friends-with-benefits relationship. He was too fearful to push all the chips into the center of the table in with anyone, but a genuine friendship with some kinky times sprinkled in was doable. So he concocted a plan. He chose a weekend when she did not have her kids. It turned out to be a Saturday. She liked to go out dancing and partying to the wee hours of the morning, he did not. He never did, even when he was her age. He had to work that day but got off early enough to make it work. He job was in the mall so that made it easier so that no time would be wasted. She agreed to meet him when he got off, though he would not divulge what they would be doing.
She arrived right on time. They embraced and he stepped back to soak her in. Dayum she filled out her jeans just right. Her beautiful round ass made him want to grope her right then and there. Her beautiful dark brown mane cascaded down her bare shoulders. Her blouse revealed enough cleavage to turn every head as they walked down the mall. He was happy he’d worn baggier slack in order to disguise his throbbing member. She didn’t react when they hugged but she had to have noticed his growing desire. She admitted to herself that she enjoyed garnering that reaction in men. Seeing her now excited him as much as what he had planned. While he wasn’t sure the evening would evolve the way he hoped, he was comfortable with the alternative. They chatted amicably as they strolled along. She was excited by this adventure as she rambled on while trying to guess where they were going. He enjoyed hearing her talk, loved her upturned nose, but mostly was slayed constantly by her dazzling smile. All were on display right now. He intentionally crossed over to opposite side of the mall from his destination as they approached. Suddenly he stopped, took her hand in his, and led her towards the Victoria’s Secret.
She hesitated for only a moment as they were about to enter. He leaned in and cooed that he wanted to buy her some nice things, no strings attached. She looked deeply into his eyes to gauge whether or not he was bull-shitting. He looked back just as deeply because he was being completely honest. While he hoped she would want to come back to his place to give him a private fashion show, he was at peace with the fact she might just as easily decline the offer. He didn’t make a ton of money anymore, but he genuinely enjoyed spending some of what he had to make someone smile who deserved it. And she deserved it because it was a struggle for a single mom to make ends meet supporting her kids on minimum wage. And he remembered some of the stories she had shared over the years involving her boyfriends and baby daddies. Buying anything from Victoria’s Secret was an indulgence she would never allow herself.
She had been lied to and screwed over by enough guys in her life to make the offer seem bogus or concealing an alternative motive. He gently pulled her inside laying all his cards on the table. Sure, if she wanted to come over to his apartment afterwards and try the items on for him he would love it, but his primary motivation was to see her indulge herself a little at his expense. He stressed that he only wanted her to come over afterwards if she sincerely wanted to, not because she felt beholden to him. That would reek of him paying for the show and undermine his true intentions. He would rather go to a strip club where the expectations were set and agreed upon beforehand. He did not see her as a stripper or a prostitute. She was a friend that he wanted to see feel as sexy as he found her to be; sexy as she wanted to feel.
There wasn’t an ounce of deceit in his words. Once she finally relented, she consumed with excitement. They perused the racks slowly as she pulled out several pieces. She asked his opinion and he gave it freely. At times, he’d wander to another part of the store to watch her from across the way. She would catch him smiling at her and ask why. Because I love seeing you smile was the reply. She held things up and he imagined what she would look like sashaying around his living room like his personal Victoria’s Secret model. She made numerous choices and headed off towards the dressing rooms. The natural clichéd fantasies of following her in and they making love to one another never entered his mind. That wasn’t what this was about. If they did actually share bodily fluids, he wasn’t sure her psyche was ready to let go of its romantic fantasies. He would be afraid she’d attach too much importance to the physical act.
Instead he settled back into a chair and closed his eyes while she tried her selections on. Slowly he allowed himself to drift off into his imagination. She would saunter from his bedroom into the living room and act out her role as lingerie model for him. As he watched her slowly move around the room, he could not help touching himself. The black silk robe he now wore kissed his skin further highlighting the sensuousness of the moment. She watched him reclining on the sofa with his erect cock in well-oiled hands slowly stroking up and down his entire length. He traced every inch of bare flesh she exposed from across the room and caressed her body from head to toe with his eyes. This brought on an even more heightened level of arousal within her. She wet her fingers with her mouth and slowly slipped them inside the thong panties she wore. She hadn’t needed to wet her fingers for they found her sex sopping and hungry for their touch. She shuttered slightly as she parted her lips and penetrated her sex. Caressing her clit, she felt her juice slowly trickle down her inner thighs. He had to slow his stroking almost completely and take a deep breath seeing her in this state. He was on the edge cumming and it felt so good he didn’t want to go over. She still had more outfits to share. When he regained control and opened his eyes, she was fully in the moment of pleasuring herself. Her face, racked by desire, was even more beautiful. Her moans began to flow from a place deep within and the expression of her desire filled the room like the voice of an angel. The aroma of her lust filled his nostrils and he felt his end was near. Her body began quivering under the first wave of orgasm. He had always envied the fact that females dive deeper into wanton release the more they orgasm, while men die their ‘little death’ when they ejaculate. For women the party’s just getting started when they cum, for guys, its game over. That’s why Michael Angelo preferred edging, developing the ability to prolong the ecstasy, sometimes for hours, was a trick he learned from the ancient Chinese. But they would be disappointed in him this night. Watching her, like this, was too powerful of an image to overcome.
She emerged a short while later and touched his arm breaking him out of his revelry. Her face beamed down on him. She inquired if he was sleepy, but he assured her he was only lost in his thoughts and not the least bit tired. Sheepishly she wondered how much he would allow her to get. Again, he wasn’t “Daddy” Warbucks so he quickly glanced at the price tags. He did some quick math and said she could take everything she was holding. Besides seeing her face, how could he deny her anything at that moment? He’d manage things somehow, he always did. She searched his eyes once more to see if she could see a speck of doubt or hesitation in them. His gaze never wavered. She gave him a big hug and said thanks. As they walked to the register, she whispered that she could tell he was already happy. He whispered back that he wasn’t ashamed in the least about how she affected him. She was beautiful and he was just a man completely susceptible to her charms.
As they exited back into the mall, he expressed hope that she would enjoy her new things and that hopefully some lucky bastard would be properly seduced by them. Smiling, she took his hand in hers saying, “let’s go back to your place and find out.”