The Woman in Pink
He first saw her from behind, walking down the aisle of the discount department store, pushing a mostly-empty shopping cart. She was about five foot six, 125 pounds, he guessed, with long, dirty blonde hair pulled back into a ponytail. But it was her carnation pink sweater that had first caught his eye; medium-weight cable knit and cropped right at her well-proportioned waistline so that when she turned halfway towards him and reached up to flip through a rack of t-shirts above her head, the sweater lifted too. He could see the smooth skin of her left flank and what was clearly a flat, lithe stomach. He imagined her hands tied behind her and pressed into the small of her back as she lay on the floor, him kneeling between her open legs, spraying his cum all over the front of that sweater. Fuck, he could already feel his cock getting hard.
She didn't take anything off the rack. Instead she turned back and unhurriedly made her way down the aisle, browsing some more. Feigning interest in a jewelry display, he let his eyes fall down the length of her body, from the sweater to the black leggings that covered her from just above her hips to just below her ankles. They were definitely an off-brand, but that didn't make the bottom they showed off any less spectacular. Her cheeks were fantastic, firm and high, with a clear, sharp demarcation where her ass stopped and her hamstrings started. She had just the barest of a gap between her thighs when she walked. There were no panty lines that he could see, and in his mind's eye he pulled the leggings down to her knees, revealing the back of a thong gripped snugly between her buttocks and creasing the lips of her pussy. What color might that thong be, he wondered? Red? Black? Pink, like the sweater? He closed his eyes and imagined hooking the middle finger of his right hand around silky material at the top of her crack, slowly sliding his knuckle down the valley of her ass, and pulling the flimsly material to the side; then slipping his finger into her wet, glistening crease and gently, slowly, sliding it into her snatch....
A hint of a smile pulled at the corners of his mouth, and his eyes, open again, continued their journey down the back of this exquisite woman. The shoes clinched his decision that she would be his quarry today. Bright pink just like her sweater, they were three inch pumps. Like the leggings, they were knock-offs and probably came from a warehouse shoe store like the one at the other end of this strip mall. Someone who could afford the real thing - a Louboutin or Versace, for instance - would not be shopping here. Maybe something fifty percent off at the outlet? Whatever they were, they lacked any practicality whatsoever for shopping in this store. To him they signified a frugal woman of moderate means who still wasn't afraid to still feel sexy; and maybe even one who wanted to think herself an equal of the shoppers downtown at the boutiques. He could give her that opportunity, at least for a little while, if she was willing.
When he pivoted down one cross-aisle and back up another to get in front of her for a quick but penetrating look from the front, he was quite pleased. She was not stunning by any stretch, and was somewhat plain, in fact. But she had an oval, pretty face, without the high, sharp cheekbones he found pretentious. Her eyes were blue, her nose was neither too big nor too small, and her lips were common and - unsurprisingly - tastefully painted with a soft pink shade of lipstick. For a quick moment he indulged the vision of a black cleave gag parting those pink lips, tied tightly at the back of her neck, under her ponytail.
She wore light make-up that enhanced all the right places without being overbearing. Her features were attractive but ultimately forgettable. There was no ring on her left hand. It wasn't a deal-breaker if there was, but more often than not those women just weren't willing to entertain his offers, even for the sums he could dangle. They usually weren't even willing to hear him out. Real life was rarely like the internet. His area was not full of MILFs desperate to fuck.
He judged this apparently-single woman to be in her early thirties, which, in his experience, was the right age. She was old enough to understand that twenty thousand dollars was real money, and young enough to let the lure of it outweigh her scruples. She would be the one he propositioned today.
He meandered through the store for a few more minutes, always keeping her on the edge of his vision until she made her way to the check-out with just a few items. As she collected her receipt, he left the store empty-handed ahead of her, walked into the parking lot, and pretended to look at something on his phone. She came out a few seconds later and, as luck would have it, headed down the same row of cars where he stood.
He walked a discrete distance behind her down the row until she came to her car, a Honda Accord that had to be at least ten years old. It was now or never.
The first key to success or failure was always the initial approach. Frighten the target, and at best he would have to quickly disappear into the massive parking lot full of holiday shoppers' cars. At worst.... Well, it was a risky game. But if he got her attention without freaking her out, then the second key would be the lure. For some - like this one, he believed - it would be the money. For others - the very, very few for whom money was not a primary motivator - it would instead be the tantalizing appeal of recklessness in a life of boredom. For a split second he flashed back to a 40 year old redhead in suburban Atlanta, naked and bent over the rail of a pool table on her stomach, arms pulled spread eagle across the green felt by the ropes tied at each of her wrists, while he fucked her from behind. But the fact was that most all of them turned him down, which just made the successes like that redhead that much more sweet.
He snapped out of the memory. To maximize the chances of success with the approach, he always stayed a respectful distance away and never made them feel hemmed in or trapped. He wasn't any sort of muscle-bound bruiser, but as a six foot, fit-appearing stranger, he knew he would likely be perceived as intimidating under the circumstances. So he counted on his expensive clothes and shoes to minimize the aura of threat. Today it was a tailored, single-breasted Brooks Brothers suit, light blue, buttoned at the top. A conservate white pocket square, folded crisply and precisely, just peeked out of the breast pocket. He was wearing a white button down shirt, open at the collar with no tie. He liked a little extra length in the hem of his pants - couldn't at all understand how 'floods' seemed to be in right now - under which he wore simple dark brown Berluti Oxfords. A matching belt completed the look. His own strawberry blonde hair was cut short and he was clean-shaven, appearing for all the world like what he considered himself to be - an upstanding middle-aged businessman doing some holiday shopping of his own, unusual as that shopping may be.
For the lure, there was something much more straightforward - two plain, white envelopes, one in each of his inside jacket pockets, and with each containing precisely ten thousand dollars in new, crisp, hundred dollar bills.
There was no one else in earshot and she had just slammed shut the trunk of her car when he spoke.
"Excuse me." This part always scared him and he felt his heart accelerate with anticipation. There were so many ways things could go wrong from here.
