The Entrepreneur

Author: Sch

A young man ran between two hotel wings, sprinted around a corner and hurried from shadow to shadow with a large cardboard box in his hands. Stopping and checking his surroundings, his attention was captured by a man and woman making love in the room where he’d stopped. He crept close and looked into an open area of the window. The man was huge, frightening. He held the feet of a teenager, while pumping his huge cock into her ass. She twisted and cried beneath him.

The young man licked his lips, looked around at the nearly empty hotel, then sprinted to a lighted set of stairs at the far end of the hotel. The stairs were metal with concrete treads filing the metal i-beams.

Lights outlined the hotel as a car turned into the parking lot and made it’s way to the hotel’s front office.

Sean Curtis jerked back into the shadows beneath the stairs and waited until the car was out of sight. He took a deep breath, then continued experimenting with the camera in different areas. The stairs had built-in lights, to light metal rungs at night. He found that the camera could be placed between two of them, to give him a lighted view beneath any dress. The rungs were narrow enough that he could aim the camera up the stairs.

He looked around nervously, then took a rechargeable drill from the cardboard box. He glanced around one more time, then held the drill against the metal stairs and began drilling. He held his breath at the racket he created, then gave a sigh of relief when the drill punched through the heavy metal. In another minute he had a second hole drilled. He licked his lips and dropped the drill into the box.

Taking a rag out of the box he dusted the metal fragments away. He took a metal strap and bolt out of the box, slid the bolt through the strap, and threaded it into the hole. He drew out a video camera, slid it into the metal band, and tightened it into place. Next he took an outlandish contraption and positioned it against the on/off switch on the camera. He tightened that down with a second steal band. Looking happily at his handiwork, he checked the camera’s alignment once more, then tossed his tools into the box. With a last glance around, he hurried into the woods and followed a creek bed to his house, directly across a wooden security fence. He stowed the box in the garage, went inside, and hurried up to the second floor. He listened to make sure his mother and sisters were asleep, then ran to his bedroom and looked through the window at the hotel stairs.

He took a remote control, once used on a long- forgotten toy, and clicked the switch experimentally. If it had the range, he had just switched the camera on and back off. The button-pushing servo should have enough range. He just had to hope that it did, he was too tired to go back and find out.

Sean pulled the end of the bed over to his window, laid on the bed, and waited. When he saw shadows approaching the stairs, he quickly clicked the remote. A man and woman went up the stairs. As they disappeared he clicked the remote again. If everything was working properly, he had just filmed his first upskirt.

Sean already had his mother and sisters on the tape. No nudity, just panties. But even those were exciting. Franks said film everybody, then hire a couple of girls to sign bogus release forms. It was a cinch, everybody did it, and he’d done it many times himself. Sean would get a lot of money for his tape, Frank said. Sean didn’t realize that if it was so easy, Frank would be rich. He wasn’t.

Taking into account that Frank was a natural born liar, but Sean’s friend, he remained hopeful. Sometimes Frank did know all the angles, since he was much older than Sean. Sometimes he was full of shit. Now, as Sean watched the second girl approach the stairs, he simply wanted to see the tape. He would worry about selling it later. The thought of what the tape might contain was making him horny.

Sean had never heard of upskirts until Frank spoke of them. He didn’t know the word voyeur, until he heard it given to a peeping Tom. Sean had been a voyeur for years, and didn’t know it. He called it spying. He had a whole assortment of mirrors, periscopes, drills, and entry door viewers, in his secret box. Now he added the family video camera to his arsenal of weapons. If somebody spotted it and took or destroyed it, he was dead.
Sean waited for two more women to go up the stairs, before he simply left the camera on and went to sleep. He would sneak over and change tapes in the morning.

Shaking with nervousness, breathless, and excited, Sean slid back in the chair and held the VCR remote before him. He whispered a silent prayer, then pressed the play button. The first skirt swept over the lens immediately. The vibration from their feet distorted it for a moment, then it cleared to show a shapely ass in white panties, showing intermittently, as her skirt waved behind her.

“Oh fuck!” Sean howled in delight, pounding on the arm of his chair.
“Sean, are you swearing,” a distant female voice asked.

“No mom,” he called. He reversed the tape and paused it, with a perfect view of a flawless ass. He couldn’t see the face, but it didn’t matter. He could tell from behind that she was a young, beautiful woman. She had slender legs and a fantastic figure. That was all that counted.

“Oh, you sweet little mother,” he whispered in appreciation. He continued the tape. He was disappointed that the next two women wore levis. The third wore a long, sweeping dress which totally obscured the light. He could see nothing. That was the last of the upskirts he had taken, now it was time to fast-forward and see what the unaided camera had done. He pressed the button. He was momentarily hopeful when two feet appeared on the screen, but it was a pair of guys. He continued his search until bare ankles stepped over the lens. He watched hopefully as the legs lengthened, as they marched away from the lens. In a moment he paused the camera on his second good upskirt. It was a woman with long, slender legs, a short blue skirt, and yellow panties. He had never seen yellow panties before. They glowed in the light of the stairs, brighter as they passed a light, then diminishing as they receded. He paused the tape again, breathing hard as he stared at the sweet ass before him. She was perfect, he thought, looking up and down the length of her slender legs. He could almost feel the firm ass between his hands.

Clicking his tongue in appreciation, he again fast- forwarded the tape to the end. She had been his last upskirt. Now he needed to bring the family VCR up to his room, combine it with his VCR and make a short, perfect tape from his clips.

Combined with the one he had taken of his mother, while washing dishes, and sisters sitting around in their bathing suits, he would have a very good beginning. He would have to show it to Frank.

In the meantime, Sean reversed the tape to the yellow panties. He paused the tape and rested his chin in his hands. She was so perfect, he thought to himself. How did it feel to be so sexy, so damned beautiful? Would she be excited to know that men were looking up her skirt? Would she someday see the pictures on the internet?

Sean felt his cock throbbing in his pants. He stood and hurried to the door, locked it, then turned the tv so he could see it from the bed. He took a white sock out of his drawer, and took it back to the bed. He stripped quickly, bouncing on the bed, turning this way and that until he lay naked. He rolled the sock down over his cock and began stroking it slowly. A blissful look crossed his face. He looked at the shimmering picture of the yellow panties and perfect ass, while picturing his face touching that ass, his hands sliding beneath the panties and touching her wet pussy.
Breathing hard, Sean stroked his cock furiously. He closed his eyes and imagined all sorts of shapely asses. By standing beneath a metal grill in a sidewalk he could look right up beneath those beautiful skirts which he saw constantly downtown. In a stairwell, he could watch them climb the stairs, as the camera had only hours before.

Fire brewed in his balls. He clenched his teeth and worked his hand furiously up and down the length of his cock. With a moan, he began shooting cum into the white sock. He moaned loudly, with his eyes riveted to the tv screen. He relaxed, allowing the sock to fall gently to his stomach. He gave the yellow pantied ass a fond smile, then frowned as the VCR automatically cut off. He had left it on pause too long. It didn’t matter, he was done. And he would have a lot more in the future. It was too bad that he couldn’t see the woman’s face. On the other hand he could put any face to that shapely ass.