New Shoes

Jason was in a hurry. He just found out he had an out of town meeting the next day, one where he needed to wear his best suit, the one that was at the cleaners. After finalizing his travel arrangements he left work early and rushed to the cleaners and grabbed his suit. Only then did he remember that he had all but ruined his black shoes during the last heavy rainstorm.

He didn't want to go to the mall and get in the middle of all the Christmas traffic, but he also didn't have time to go across town to the discount shoe place. Remembering seeing a new shoe store in the small shopping center near the grocery store he tossed his suit in the back seat, climbed into his car and headed toward home. Sure enough, just a couple of blocks from his house he spotted the shopping center and at the far end was the S&M Shoe Market.

Pulling into the parking lot he pondered the name of the store, "Shoe Market," he thought, "has a homey, but interesting ring to it." He headed on in and was pleasantly surprised by the selection of nice looking men's shoes. Jason was even more surprised when he saw how reasonably priced the shoes seemed.

He heard a deep woman's voice from behind him ask, "May I help you?"

Without turning his head from the racks of shoes, he held up a shoe in each hand and asked, "Do you have these in an eleven D?" Then turning towards the woman he continued, "And one of..." He suddenly felt tongue-tied as he looked up at the woman. Jason was just over six feet tall and he found himself looking up at the woman's face.

"You were saying," she asked, tossing her long blond hair and letting it cascade down her shoulder and over her breast.

"Ah, oh yes, I also would like to ah, try on one of these in an eleven d," he replied nervously, trying not to stare into the cleavage so wonderfully framed in her low cut blouse.

"And when was the last time you had your feet measured for shoes?" she asked. He accent was compelling, it sounded like Russian, or some other Eastern European country.

"I don't need to measure my feet, I know I'm a size eleven, it's the only size I've bought for the last five years."

"Here we measure all feet. We want to get it right, so no measure, no shoes."

"Okay, it's just that it's almost closing time," Jason replied.

"Well then we better measure quickly," she replied pointing to a nearby bench.

Jason sat down and watched as the tall woman bent over and grabbed one of those odd seats they had in shoe stores, the one with the angled footrest on the front. He couldn't help but notice the way her hips curved out from her waist. If she were perhaps a foot shorter she'd have the absolute perfect body, he thought.

She slid the seat up facing him and then sat down. As she settled onto the seat, Jason gasped, noticing that she straddled the foot rest, which hiked up her, already short, skirt to the point he had an unobstructed view of her panties. These panties were actually so sheer, that he had a complete view of her matted blond pubic hair and a very inviting slit.

Fortunately the woman didn't seem to notice him gawking at her pussy and he was able to regain his composure as she slapped that foot measuring device down in front of him and grabbed his right foot, pulling off the shoe. Placing the foot on the device she jotted down a notation and then flipped the device over. Not waiting for her to remove the shoe, Jason slipped off his left shoe and then let her put it on the foot measurer.

All the while she was measuring, Jason kept glancing back between her legs. He imagined running his tongue up and down that beautiful slit, tasting her, slipping his lips over her... "Excuse me?" he asked, realize she had said something.

"Please stand up now," she replied.

"Oh damn," he thought, he couldn't stand up now, not with the raging erection he had. Stalling he stammered, "You want me to..."

"Yes, you stand up now."

"Stand up, ah..." he squirmed in his seat, trying to get himself adjusted.

"Yes, you stand up," she said, tucking her hands under his arms and lifting.

Surprised at her strength Jason felt himself lifted up from the chair. Standing now, he hunched over trying to conceal his erection.

"No, you stand up straight, so I can..." She had reached around behind him and pushed his back forward, forcing him to stand up straight. When she nearly got poked in the face with his cock she stopped talking and then looked up at his face.

"I'm sorry it's just that... you, you are so tall and ah, beautiful and seeing..."

"You looked up my skirt?"

"I couldn't help it, I mean you..."

"You want something besides shoes?" she asked matter-of-factly.

"I need shoes."

"What is it you want?"

"Just shoes?" he asked meekly.

"You are asking me?"

He shrugged his shoulders.

"Wait here," she said, standing up and walking over to the store entrance. She pulled out her keys, locked the door and then turned out the lights. Several of the lights in the store remained on so Jason could see as she walked back to him.

"What are you doing?"

"Don't worry, I get you shoes. Now follow me little man."

"Little man?" Jason thought. Last time he was called that he was like in second grade. Of course, as he stood up and then followed the tall woman he realized it was appropriate now. He followed her through some curtains and then down a dark aisle that was stacked top to bottom on each side with shoe boxes. They stepped into a larger room with chairs along one wall.

The woman pointed at the chairs and said, "Please, sit over there. I will be back in a moment."

Jason sat down wondering what he had gotten himself into. All he wanted was a pair of shoes, well, that and the saleslady's legs wrapped around him. He knew he could get the shoes.

A door opened and the woman stepped through wearing a pair of long black boots that laced up to her thighs. The rest of her was strapped and buckled into a black leather outfit that exposed her full and very naked breasts. Looking down Jason also saw the soft pubic curls, this time not matted down by panties, they were uncovered, as was the slightly swollen lips of her pussy. Walking into the room, she shook her head to toss her long hair over her shoulders and then he noticed she was holding a riding crop.

"What is going..."

"Quiet," she said sternly. She stepped up in front of me, pressed the end of the riding crop under my chin and said. "You will remove your clothes, all except your socks, do you understand?"

Jason nodded.

"Then you will put these on," she continued handing him a pair of shoes.

"But they are too small," he replied, after looking inside them.

"Regardless, you will put them on if you wish to continue our little, how do you say it? Session."

Jason looked down at the shoes, then back up at the tall sales woman with exposed breasts and pussy and those long, thigh-high boots. He then placed the shoes down on one of the chairs and quickly began removing his clothes. When completely naked except for his socks, he tried pulling on the but he couldn't work his heels in.

When the woman noticed his predicament, she brusquely stepped forward and handed him her riding crop, which actually turned out to be a long shoe horn. He was able to work his feet into the shoes using the shoe horn. Handing her the shoe horn, he complained, "These are uncomfortable."

"Good," she said flexing the shoe horn like a riding crop. She suddenly turned, held the shoe horn over her shoulder and slowly walked to the other side of the room, sitting down in one of the chairs. She sat down in the chair, crossed her legs at the knees and asked, "Whatever could this little man be thinking. You, perhaps, want to taste my pussy?"

Jason nodded vigorously.

"Even in those uncomfortable shoes?"

"Can I take them off?"

She smiled and shook her back and forth. "If you want this you will need to walk over here," she said, uncrossing her legs and opening them.

Wincing, Jason took one slow step forward and then another. The pain in his feet was bad, but not bad enough to divert him from his goal. He continued until right in front of her where he kneeled down. Leaning forward, he was about to dive in when the saleslady blocked his progress with the shoehorn, "Ah, ah, ah, ah..." she chimed. "I don't want you on your knees, I want you to squat down to do this."

"But my shoes..."

"So, do you want comfortable shoes, or uncomfortable shoes and my pussy?"

Jason quickly got up into the squatting position, wincing with the pain, he leaned forward and this time she left him unimpeded. Trying to ignore the pain, Jason leaned forward, resting his hands on her soft thighs, while moving his face close to her pussy. He breathed in her fragrance and the pushed his tongue between her lips, sliding it into her wet opening. Pushing further, he moved his tongue in and out of her, savoring the tangy flavor.

Withdrawing his tongue from her opening, he slid upward between her flowery lips until he found the tiny nub at the top of her slit. He began circling her clit with his tongue, listening as she began to moan and breathe faster. Pushing his face to her, he slipped his lips around the clit and gently sucked it. Pinching it between his wet lips he felt her responding. She lifted her hips, pushing against him while her hands moved down and ran over his head and through his hair.

The pain in his feet forgotten for the moment, Jason moved his tongue over her clit faster and faster, feeling her pull his face onto her pussy, his face in between her lips. He was breathing though his nose now, nearly as hard as she was, but he kept his tongue moving on her, all over and around her clit. Suddenly, he felt her hands tighten on his head as she lifted her hips and moaned loudly. He move his right hand from her thighs and pushed two fingers into her. Now he could feel her coming, feel the contractions in her pussy as she moaned and moaned.

Jason kept his fingers inside her until the convulsions subsided. Easing them out of her, he moved back and then felt the pain in his feet. He looked up at her face and when she nodded, he stood up, sighing in relief as the pain subsided. The woman took the shoehorn and pressed it to Jason's chest, moving him back from the chairs. She stopped pushing him when he was out in the middle of the room, then she moved over in front of him and kneeled down.

Jason felt something cold on his balls and realized she had pushed the shoehorn up beneath him, pressing it to his balls. She then grabbed his cock with her free hand and began stroking him. While the stroking on his cock felt good, the woman would change the angle of her stroke making him lean backward or forward some to keep his balance. Each time he leaned, he felt a shot of pain from his shoes.

Trying to concentrate on the pleasure, he suddenly lean back and wince in pain, he'd then feel himself getting closer to coming and then have to lean forward and feel the pain. He had hoped this would stop when she slipped her mouth over his cock, but just by the way she moved her head, and pushed him with her free hand had him slipping from pleasure to pain and back again. He'd just about reach the point of coming and damn, the pain sliced through him. And then again he'd be ready to spurt into her mouth and she'd bump him with her head, making him lean back and feel the pain.

Jason hovered on the edge of ecstasy and agony for an interminable length of time. Finally, she let him stand without leaning and he felt the pleasure rise in his cock, more and more, and then finally he exploded, splashing her mouth with spurt after spurt of his cum. He grabbed her shoulder and steadied himself as his cock continued to twitch in her mouth as she sucked and sucked the last droplets of cum from him. When she pulled her mouth away, wiped up the bit of cum running down her chin and then swallowed, she said, "You can sit down and take off your shoes."

Jason fell back onto the chairs and eased the shoes off his feet. He pulled off the socks and looked over the red streaked pressure points. Blisters were forming in some areas. She handed him a tube and said, "Use this on the blisters, if they break, cover them with a bandage until it dries." She then walked out of the room.

Jason got his clothes together and got dressed. He eased his socks back onto his feet, but waited before pulling his shoes on.

In a few minutes the woman appeared, fully dressed holding two boxes. She opened the first box and said, these are the shoes that I measured you for. They should be very comfortable, you can try them on now.

Jason slipped on the shoes and even with the blisters and raw spots on his feet they felt great. "These are very comfortable," he said in surprise.

"You see how good they are when you let me measure. You wear those to your meeting and whenever you need something comfortable."

"Okay, and the other box?"

"We are having a two for one sale today. This box is for these shoes," she said, grabbing the painful shoes he had just taken off. "These shoes are when you want to be uncomfortable and remember me."

Nodding, Jason handed her his credit card. She ran the card and then led him out of the store, unlocking the entrance.

"Goodbye," he said.

"Be sure and come back soon, I have a lot of comfortable shoes and even more uncomfortable ones." She gave him an evil looking smile then locked the door between them.