Brad, then 24, was hired as a young salesman for a software company. He worked in a cubicle on a second office building in a nowhere city. He was young, dumb and eager. He was also, secretly, a full fledged pervert. When he was younger, he became fascinated with his mother's clothing. Particularly, her leather boots which she paraded around virtually everyday. Usually accompanied with a dress and denim jacket. When she left for the bars on weekends he noted her tight pants and fitted tight leather coat complete with steely black boots that sat on a high heel and made her seem like a rock star. As she would walk out she'd sweetly sing "bye bye" as she closed the door. He would then quietly climb the stairs, open her closet, root around to find the most recently worn pair, which he always made a note of, and with boots in hand, open the hamper to find a recently worn pair of her panties. Then Brad would climb onto her bed and take off his clothes. There he would smell her panties, put them on and start smelling her boots. When his erection at an all time hardness, he grabbed his pantie clad prick and pump until he exploded. With his other hand he smelled and licked her boots clean of any aroma or, if he was lucky enough, the remaining sweat from her feet.
She had six pairs of boots: two pairs of cowboy boots, one black and one brown, a white calf high, two black knee high boots and his favorite, a black tanned leather knee high pair particularly prone to being quite odorous. Brad always felt pangs of guilt after he did all this and often couldn't look in mother's eyes for days but when he found himself alone he reverted to his filthy tendencie. Once his mother had a friend, Marie, who spent the night and had worn a black leather skirt. He found it marvelous. It's thick skin texture and cold yet soothing feel. He had found it on the bathroom floor and he smelled, licked and rubbed it on his face. Then in an act of excitement, he put it on and marveled how it looked tight and fitted on his rather full ass. It made him feel sexy and he came without even touching himself ...but that was long ago he thought.
After he graduated college he found himself working a lot and soon developed a normal sex life. He was a tall, attractive guy and active soccer player. He had girlfriends and had sex. He had a 6 inch penis that was quite wide with low hanging testicles. He loved getting erect and feeling it. He even had a similar sized dildo that he, when alone, would insert in his anus or suck on. He thought he was quite good at fellatio. He loved wearing his own leather jacket, boots and nothing else. He would take photos and send them to men on Grindr just to tease. His mom's boots were in the past but he still knew he was into kink. He just thought his mother's scent filled days were behind him.
At the office, he noticed an older exec named Jacklyn. A fifty something white haired woman with thick fashionable glasses. Brad had never noticed older women but, Jacklyn, intrigued him with her tight outfits and heels. She was average height with wide hips and she was happy showing off her curves even if others her age thought it distasteful. On cooler days, Jacklyn walked in with an array of sexy boots. ankle length, cowboy, knee high and even a black pair of thigh high boots that she wore with denim on Friday. Brad became overly curious about her and even friended her on Facebook. There he learned she was married with a few children. She often posted selfies which he resisted liking. She was friendly with him but never talked to him much. He felt she was aloof but he still was fond of her.
Then one Tuesday, she entered the office with tight black leather pants and heels. They clung to her like skin but he knew from the dull reflection they were pure leather. His cock grew stiffer and he felt a rush of heat to his face. He found excuses to walk by her office or go to the bathroom around the same time she did just to peek at her leather clad ass. He felt compelled like some sex drone and thought he was being foolish. But the cold black look and sound of her hips moving made him flush with a throbbing rod between his legs.
Towards the end of the day, he walked in the break room and she stood there talking to a couple of colleagues. They all said hello as he grabbed his water. He stood with them a minute to chat and tried as hard as possible to behave normal. He said something about sports, then the rain and then he blurted:
"I love your pants, Jacklyn!" He stammered a bit. The act of saying it was not with any ease. He felt sudden embarrassment.
"Oh, thank you." Jacklyn tilted her head to the side with a fake smile and quickly looked back at the other staff. She engaged back with the previous conversation as if nothing happened. The male co-worked side eyed Brad with an expression of "really?".
Brad walked away dejected. His usual cavalier compliments scored well at the weekend drunk bars but here he felt the very definition of inappropriate. The next day he was afraid to look at her or anyone. He muddled through his morning like an ill tempered kid as he feared HR would ask to see him.
At 12 noon Brad got an IM from Jacklyn:
"I normally take every new salesperson out to lunch for some 1 on 1 FaceTime. Today's your turn at 1 pm. Interested?"
Brad quickly replied yes due to his desire not to be having an awkward conversation in the Human Resource office. At one he nervously walked towards her office. She walked out wearing a fitted grey dress held tightly on her hips with a wide black belt. The dress came just below the knees which exposed her black patent heeled boots ...knee high! They were gorgeous. Even more so due to wicked pointed toes that reminded him of something serpentine.
She drove. He sat in the passenger seat trying to act normal but he was so distracted. Jacklyn's boot clad foot hit the brake and gas toe first allowing the long heel to be the fulcrum. It looked sexy and his 6 inches began to throb. They sat down in Jacklyn's usual luncheon spot with a young wait staff, bare black tables and water served in wine glasses. Their table was small and the waitress was very sexy. A thick, very confident Asian girl who wore a push-up brained a flimsy white tailored blouse and black tights. As usual Brad noted her shoes: thick Doc Martens. They ordered. They chatted pleasantly for a few minutes when Jacklyn let in.
"So you enjoyed my outfit yesterday?" Brad went pale.
"I won't report you to HR. Let's just say you owe me?"
"Sure" he flummoxed.
