As he followed the woman down the crowded sidewalk, he couldn’t believe his good fortune as she had the most perfect ass he’d ever seen. The skirt was perfectly tailored for the woman’s combination of curves and muscles. He could feel the familiar stirring in his groin and was glad he’d decided to take a walk at lunch time today. At a stop light, he stopped far enough back and gazed even more closely. His breath caught when he caught the unmistakable lines of garter straps. When he looked even closer and saw that there were six straps, he sighed with pleasure. He resisted the urge to grab her, haul her into an alley and fuck her brains out. His never ending desire for women was further complicated by a fetish for glamorous lingerie. It got even more interesting for him a block later, when the woman had to step up to a higher than normal curb and she hiked her skirt up a bit to allow for the curb. He caught a flash of a bright red slip and he immediately knew from the lace at the hem it was a vintage Vanity Fair slip. That put his cock into high gear with the thought of slowly rubbing his cock against the silky nylon before hiking the slip out of the way to bury his face in what he surmised was a beautifully groomed pussy.
At the next stoplight, he came up next to her and waited for her to look up at him. When she did so, he smiled deeply and said, “I hope you don’t mind, but I need to tell you that I often struggle with the question of God’s existence.” The woman gave him a strange look and look like she wanted to ignore him, but as was often the case, she seemed unable to break away from his gaze. He then added, “However, when I see an ass like yours I know that there must be a God.” She gave him the typical you have to be kidding look, but he could tell from her blush that she also liked the compliment. She stormed off, but he caught up with her at the next light. She refused to look at him this time, but also didn’t move away and he could sense the internal conflict going on inside her. He leaned in and said, “In fact, I probably should go to confession as the thoughts I’ve been having are bordering on obscene.” This time the woman looked up at him and he took in the face that looked back at him. She was in her 30s, or possibly a bit older and just well maintained, and she carried an aura of respectability and class. That only made him want her more. In a voice that illustrated her education, she said swiftly, “I suppose it’s possible that your ridiculous lines work with some women, but it won’t work with me.” Her eyes were defiantly radiant, but he saw something else; something he’d learned to read.
You see, at first glance, this thirty year old accountant was wise beyond his years. He had taken it upon himself over the last decade to become a professional student when it came to women and their deepest, darkest desires. He would often laugh to himself that he wanted to know what made women tick so he could get them on his dick. He found the saying a bit lewd, but it was definitely accurate. He’d studied every major religion, countless volumes on women’s psychology and sexual preferences as well as a very in depth internship with a master hypnotist. Once he felt like he’d exhausted everything he thought he could learn from text books and the internet, he dove into a ‘hands on’ study period. As they stood at the red light, he thought back to his first subject. Her name was Lily and she was somewhere in her late 40’s. She was the librarian at the local library where he did much of his studying and she was the perfect test subject. She came across as almost completely asexual, but yet on the first day of trying his new technique; she was sucking his cock behind the book rack of the library. It led to a heated two month sexual tryst that helped him learn even more about women. Since he completed his hands on training some 3 years ago, his percentage of ‘closing the deal’ was now at 99.6%. And since by his records (and they were quite detailed), this woman on the street corner was number 1,000, he’d only struck out three times since he’d ‘mastered’ his technique.
For anyone that is good with numbers knows 1,000 women over three years works out to nearly a woman per day and since many of his liaisons would last for several days, he had gotten a lot of pussy over the last three years and he had no intention of slowing down. The more women he experienced, the more he wanted. This woman that was his latest target was easily in the top five. He looked at her again as she stood trying to ignore him. He noticed that she clearly had money as her clothes were expensive and her jewelry was even more so. He had found over the years that even women that think they would never be involved in an affair or a quickie could be persuaded. It was women like this rare beauty at his side that once they gave into him, they displayed the most unquenchable sexual thirsts. He sensed that she would surpass even his highest expectations. In a nearly inaudible whisper he said, “I do apologize if I’ve offended you.” He let her walk off when the light turned green and as she neared the other curb, she looked back at him and seemed surprised that he hadn’t followed her.
They shared a gaze and that’s when his training in hypnosis came into play. He knew from past experience (he often had very detailed conversations with the women about why they’d given into him) and most of them said that when he gazed into their eyes they were amazed at how their bodies had reacted. His favorite response was from a dazzlingly beautiful woman that had admitted that she had climaxed simply from him staring into her eyes on a city bus. They determined that her hyper hormonal state from being two months pregnant at the time likely played a part, but he still enjoyed thinking that just his hazel eyes made a woman cum. He stepped off the curb and slowly followed her. She was now looking back at him every few steps and had noticeably slowed her pace so that he was quickly catching her. When he was only ten feet or so from her, she turned and window shopped as if she wasn’t waiting for him. He stopped when he was several feet behind her, but she knew he could see him in the reflection of the window. He gazed at that sweet ass that had gotten his attention in the first place and he mentally undressed her. He wasn’t sure exactly how long he stood there behind her without moving or speaking, but she finally looked up to look at him in the reflection of the window. They looked into each other’s eyes for another several minutes and he mentally said, “You are the most desirable woman in the world and I would be honored to enjoy your body.” He could see her smile as if she had understood and at that moment he knew she was ready.
He finally stepped forward and ran his hand slowly across one of her ass cheeks. He could feel her tremble and when his hand reached the crack of her ass, he squeezed hard enough in the gap between her legs that she would feel the pressure against her pussy. She couldn’t quite stifle the gasp that spontaneously erupted from her sweet lips and as she started to move away (something that most woman would do just before their last bit of self-control drifted away), he moved his hand to her hip and then bent down and stepped forward so he could press his engorged hardon against her ass. She pushed back against him with obvious need as she softly said, “No.” He bent down and nuzzled her neck and then as his hand undid the buttons on her suit jacket, he whispered in her ear, “Say please; you’ll be glad you did.” His hand delighted in the realization that under her suit jacket was the half slips matching camisole and as soon as he heard a breathless please leave her lips, his hand moved up and cupped one beautiful breast. He could feel that she was wearing some kind of lace bustier and as his thumb moved across the silky nylon of the camisole and caressed the hard nipple there, he surmised that the bustier was quite naughty as although it supported her beautiful C cup breasts, it didn’t cover them. He knew the next few minutes were critical since if he gave her too much pleasure too early, there was a chance she would be satisfied enough to break the trance he had over her and walk off; leaving him with a raging hard-on.
However, his fetish for lingerie demanded that he see more of her incredible lingerie now. As he turned her towards him, his lips traced a line across her beautifully painted soft, full lips. Her hunger was evident as she pushed hard against his lips and her tongue wormed its way into his mouth. His hand carefully pushed her camisole strap down her arm pulling that side of the camisole down with it. He spied her beautiful breast and smiled when he saw there was no tan line. His finger trailed across her bare flesh pushing the camisole even farther down. He finally saw what he wanted to see; a pink lacy basque that so beautifully framed her tits that he knew that she was a one in a million woman; not one in a thousand as his tally sheet would indicate. She finally realized that her magnificent breast was on display to any onlooker walking down the street and shrugged her suit jacket into place while grabbing his hand and leading him inside the department store. The next few minutes were a blur of escalators and walking until they were in the parking garage attached to the store.
Her expensive heels clattered across the cement until she pulled him into a gap between two SUV’s. She looked deep into his eyes and said, “I don’t know why I’m doing this, but I must have your cock….now.” He smiled pleasantly and softly said, “Your wish is my command” and then he quickly hiked her skirt up out of the way so that he could massage her pussy through her slip. She groaned and leaned back against the fender of the SUV and humped his talented hand. Tracing along the gusset of her panties, he realized that she was wearing a garter panty as he felt the familiar hook and eye closure. He closed his eyes as her hand gripped his cock through his slacks and he felt a pleasure that none of the other 999 women had given him. He deftly undid the catches and then pushed her slip along with two of his fingers into her welcoming pussy. Although he suspected she’d had several children, her pussy was tight and she leaned forward to groan in her ear, “I’ve always fantasized about someone fucking me through my slip; please tell me you’re the man of my dreams.” His world felt like it was coming into some sort of cosmic perfect alignment as although he’d performed this particular fantasy of his own many times over the last three years he’d never had a woman tell him that she’d fantasized about being slip fucked.
He growled his answer and lifted her up and pinned her against the front quarter panel of the SUV. His mouth moved down and sucked a nipple into his mouth and she shrieked as she announced she was cumming. She pinned her heels against the other SUV and he mentally laughed at what her heels were going to do to the Hummer’s paint job, but he quickly focused on her hand reaching down and freeing his cock. When she finally grasped it in her hot hand, she moaned, “Oh my God” before guiding it to the opening of her slip lined pussy. She pushed hard against him and he fought hard to keep control. Normally someone that can keep his nut for hours on end, he felt such pleasure that he almost came right then and there. She was so tight and her honey coating the slip felt like liquid butter sliding down his cock. His hands were gripping her ass through the slip as she used her strong leg muscles to ride up and down his shaft. She started murmuring something that sounded like a foreign language and he knew she was close to a massive orgasm. He heard a cell phone and she somehow magically pulled it out of her suit jacket and answered it. She motioned for him to stop moving and in a strained voice told what must have been her husband that she had just gotten a call and there was an IT catastrophe in the making and she wouldn’t be home for hours. He smiled at her elegant ruse and rotated his hips and pushed his cock deeper into her sweet pussy. She groaned after moving the phone away from her mouth and gave him a look that bordered on murder, but with plenty of lust. She apologized but said she had to get going. She hung up just in time as she squealed in response to him pulling on the waistband of the half slip which caused the silky nylon to rub against her clit and started the waves of pleasure unlike any she had ever experienced.
She threw the phone onto the hood of the SUV as she groaned, “You talked about God earlier, but you’re the fucking devil, aren’t you? The devil with a glorious fucking cock.” He could feel her body shaking with pleasure and he pressed her more firmly against the side of the car as he dug his fingers into her sweet ass. He had never felt such intense pleasure and peace within himself and as he buried his lips into her neck, he vaguely heard himself mumble, “I love you.” It was a phrase he’d never uttered to a woman and it seemed to magnify her own pleasure as he felt her body shake with even stronger intensity and then he felt a wave of hot lava flowing around his cock as she ejaculated over and over again. For him, it felt like a fire hose full of heat and he could feel her pussy muscles clenching him over and over again. As she spoke in some unknown language of lust, he threw a few more strokes into her and then he exploded.
He held her tight to him and pressed his pelvis into hers more firmly and rotated his hips enough to move her slip against her clit some more and she squealed, “You glorious bastard” as another orgasm began. A few moments later, she whispered, “My company keeps an apartment nearby for people stuck in the city, I’ve got a key and I know it’s not being used.” They walked off arm in arm and wondered what would happen next.