Little Guy Brad

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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 mamak escort 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. ofise gelen escort 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.

“Why leather?” She quizzed him.

“Oh I think it looked nice on a woman.”

“Hm, just leather pants?”

“Um no …boots too. My mom had all kinds” he immediately regretted mentioning that.

“Oh, she sounds fashionable. Did you always fancy her fashion sense?” He nodded, yes.

“Does she have boots like mine?” She extended her foot towards him so he had to purposefully look. He became erect and slightly frightened. He couldn’t believe they were having this conversation.

“Since you owe me a favor Brad, I want you to go to the bathroom and remove your underwear. Come back commando, under your chinos there and give the undies to me. I want to see what kind you wear. Ok?”

He was completely flush and red faced but he stood up almost as in a trance. He was numb but also seething with frightened ecstasy.

“Oh and Mike, don’t play with it and hands behind you when you walk back.”

Brad went to the bathroom and entered a stall. He did what she said and could barely button his chinos due to his dick now fat and full under his zipper. Even his balls seems engorged. He walked back to the table undies in hand. She gave him a look and he knew he had to put his hands behind his back. His erection now protruded beneath his pants making a shameful tent. A gooey drip formed where his tip was and he walked to the table feeling like a baby who was yelled at. No one looked at first. Then the waitress walked past him and glanced down. Her eyes widened, quickly looked away and she stared past him. It felt horrible and marvelous.

Once seated she extends her hand. “Let’s see the underwear type.” He handed them to her and she laughed.

“I knew you wore a banana otele gelen escort hammock. …oh and they’re quite wet. This type of underwear really is just an excuse for men to wear panties. You know that right?”.

He was shocked as he immediately thought about his former hobby and nodded yes. Then she pocketed the underwear and said: “For me later. So do you like panties?”


“Have you worn women’s underwear before?”


“Whose panties have you worn?”

“…My mothers.” His mouth was dry and he cracked.

“I had a feeling. …and did you fondle her boots too ….I’ll bet you sniffled them?”

Brad nodded. Now he was shocked.

“Oh, …You pervert.” She shook her head and then laughed.

With that she extended her right foot and said: “Open your legs” He did. She could see his erect penis along the inside of his thigh and she touched the tip of her boot right on the shaft. Brad was frozen except for the movement of pre-cum oozing from his tiny pee hole.

“Now say this; I sniff my mommies boots and mommies panties.” She looked at him like a goddess, her eyes peering from beneath her glasses. Her lips curled in a grin.

“Say it over and over and I won’t stop.” She began running the smooth tip up and down his six inches. She was a tad disappointed he wasn’t bigger but he was hard as a board. He began to say it over and over as she strokes him.

“I sniff my mommies boots and mommies panties …I sniff…”

“A bit louder.” Now he was full throated his cock in full pleasure and he started to cum. The semen filled his leg and made a large fat wet stain that made his light grey pants showcase a dark grey spot. He let out his mantra one more time the waitress returned with their order and she heard him cum. “I snifff my mommie …ungh.”

“Oh my are you ok.” The waitress glared at him.

Jacklyn lowered her foot and said: “I think he had an accident.” She motioned to his crotch which had become exposed to the entire restaurant. He froze as he saw another girl his age holding her phone out recording the entire orgasm. With her other hand she stifled her giggling. The waitress looked at the large cumstain on his pants and said:

“Oh ok, I’ll get you more napkins.”

“No thank you.” Jacklyn insisted. “I think he needs to learn a lesson for being a rude pervert. Don’t you think?”

The waitress saw his red face and agreed. “Yeah, he seems like an asshole anyway.” She looked at his stain again. “A perverted asshole …so typical.”

Jacklyn held out his man panties.

“Look at his underwear.”

“Oh gawd. ..and he’s little too.” The waitress rolled her eyes as she motioned to his now flaccid dick. He heard laughter from the girl with the phone. Jacklyn decided to eat her meal and Brad just sat there. The waitress would stop by occasionally to ask if they needed anything and to call him “Little guy”. He would be taken back to the office where he tried to hide the stain the rest of the day. As he thought he would get away with any embarrassment at the office he caught two female coworkers peeking. As they mumbled all he could decipher was: “He’s fucking gross.”

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