The Entrepreneur

Three consecutive nights netted Sean many more upskirts to add to his tapes. As night after night wore on, he began to hate women who work jeans. They ruined his upskirt tapes and the world was full of them. On Saturday he stayed up until three AM and completed his first tape. He had netted 37 upskirts on that very night. A group of high school kids had held a party and run up and down the stairs all night long, in assorted forms of dress. Sean was thrilled. He called Frank, the first thing Sunday morning. Frank promised to bring two girls to sign bogus release forms, but his tone hinted at much more.

Sean paced the house, waiting for Frank and his friends to show. He gasped as the grandfather clock began banging away, proclaiming that it was noon. Sean had the house to himself, his mother and sisters had gone to their grandmother’s house and left him all alone. He faked an illness, otherwise she would have swept him out of the house as well. Sean waited breathlessly. Frank knew some real hotties. Who would he bring? Sean couldn’t wait to find out.

Gravel grated on the driveway. He ran to the front window and looked out to see Frank’s red convertible. Sean swivelled around, following the car to the next series of windows until he saw the girls. They were old, at least 20, maybe even 25. He was stunned. How had Frank managed to get ahold of such fabulous girls?

“Oh fuck,” Sean gasped, looking around the room in haste. He needed refreshments, grownup stuff. His father visited occasionally and had some beer, which he bought at price club by the case, and stored in the garage. He need to put some in the refrigerator.

He finished just as Frank approached the front door. As usual, he stepped inside without knocking. He waved a black briefcase, then turned and ushered the girls inside.
“There he is, our future entrepreneur,” Frank called in a loud voice. “Sean, this is Cindy and Jan, he pointed at the two beautiful girls.
“H… hi,” Sean gulped, motioning them toward the couch.
“No, up to your bedroom,” Frank said agreeably. “Let’s see the tape.”
“I… Oh,” Sean said.
“Hey, what’s the matter?” Frank asked, putting an arm across Sean’s shoulders.
“You brought beautiful women here,” Sean whispered. “They make me nervous.”
“Them!” he said loudly with a laugh. “They ain’t women, they’re whores,” he laughed, slapping Sean on the back.
“Hey, Frankie, I take exception to that,” Cindy howled.
“Take whatever you want, sweet-cheeks. Get your ass upstairs and start earning your money,” Frank laughed.
“H… how?” Sean asked.
“How what?”
“How are they going to earn their money?”
“By signing release forms, kid,” he said, tapping his briefcase. “You can’t have a movie without the proper release forms. Every professional on earth get’s them like this. You didn’t think they really run down everyone on film and make them sign one, did you?”
“Well, yeah.” Sean couldn’t tell if he was lying or not. Frank lied well.
“Ok, picture this. Some old broad goes into a gas station bathroom and takes a crap. Some pervert films it and chases her down as she leaves, yelling “hey lady could you sign this.” What do you think, plausible? Hell, there wouldn’t be any movies,” Frank chuckled, pushing Sean up the stairs behind the women.

Sean stared at the beautiful legs treading the stairs before him. Jan was his favorite. Cindy seemed like a gum popping, street corner whore. Jan had class. She also had a red leather skirt that came up past her knees, with the longest pair of legs he’d ever seen. They were flawless. By bending down a little he could even see beneath their skirts and get a personal upskirt shot. He did and Frank laughed, pushing him toward the sweet ass he was surveying. He fell into Jan. Jan turned and giggled. “What a naughty boy,” she said with a thrilling English accent.

“Oh God,” Sean moaned. His cock was as hard as rock and he knew exactly where he wanted to plant it. Up Jan’s sweet ass.
“Ok, girls, take turns,” Frank said, opening his briefcase and giving each girl half the forms. He closed the briefcase and placed it on Jan’s lap. She was sitting on Sean’s bed, with her long legs hanging over the footboard. Sean was mesmerized. He had never seen so much beautiful female flesh in is entire life.

Cindy took a seat at the desk and stared at the blank tv screen, waiting. Frank spread a few forms out in front of her and handed her the pen.

“Hit it, Sean,” Frank called, sitting on the bed beside Jan. Sean was a little angry, he had wanted the spot beside Jan. Frank leaned close and kissed Jan’s ear. Sean took the remote and started the tape.
“Oh wow, what an ass,” Frank howled in appreciation.
“That’s my mom,” Sean said resentfully. Only Jan seemed to notice.

“You take her,” Frank nudged Jan’s elbow. Jan wrote a brief description of the scene, then signed the form. Sean couldn’t help but be turned on, with three strangers watching his mother’s ass as she worked. It was exciting, he reluctantly admitted. Jan seemed speechless. Her eyes were glued to the screen.
“Very nice,” she whispered.

“I’d eat it,” Cindy said, sitting back and kicking a leg over her knee. Sean suddenly realized that it was a mistake to film his mother. If he couldn’t stand how these three people treated his tape, how would he feel when thousands viewed it. old men masturbating, lesbians ogling…
“Oh fuck, check that out!” Frank howled.
“Those are my sisters,” Sean said in growing anger.

“I need to get to know them better,” Frank said, nudging Jan again. Jan didn’t comment, she was staring at Sean.
“I’ve got the red bathing suit,” Cindy called, scribbling quickly.
“I’ll take the cute girl in the yellow,” Jan said. She scribbled briefly, then added the form to the bottom of the pile. With a great deal of relief, Sean watched the scene turn to the first girl at the hotel. He felt his cock throbbing, as he watched the sweet ass treading the stairs.
“I like that,” Cindy said as she wrote.
“Very nice,” Jan nodded.
“Good photography, kid. It makes all the difference.”
“It’s obvious that this was filmed with a home camera,” Jan said in her amazing accent. “That will increase the value immensely. There are too many fake upskirts out there. People can tell the difference.”

“There’s yours,” Frank pointed at the screen, then leaned forward to kiss Jan’s neck. Sean wanted to scream at them to leave. Cindy was nice, but Frank was hitting on the girl Sean wanted. He felt betrayed.
“I… I don’t think I want to do this,” Sean said hesitantly.
“What?” Frank roared. “Hey kid, I own these girls until three. Do you have any idea how much that costs?”
“No, but it’s my tape,” he said, looking at Jan defensively.
“I’ll tell you what, kid, you can have Cindy for the rest of the afternoon, if you give me the tape.”
“No, I want Jan,” Sean said before he could stop himself.
“Uh-uh, she’s mine.”
“I am not yours, and I happen to agree with Sean. I think we would hit it off well.”
“Hey, lady, I paid…”
“Not enough to order me around. If you want us to leave with these forms in hand, simply continue this conversation,” she said, putting her hands on the pile of papers.
“Ok, you win,” he pretended to be agreeable. Sean suddenly realized that Frank was not really his friend. He was just an acquaintance. He wasn’t even sure that he liked Frank.

“Over here, Sean,” Jan patted the bed.
Frank stood, forced a grin and pushed Cindy off the chair. He sat and pulled her back into his lap.
Suddenly shy again, Sean sat by Jan. He loved her perfume. It was spicy and exotic.
“Move closer,” she said as she scribbled on another form.
“You’re nice,” Sean whispered. She turned and kissed him on the lips, then scribbled another notation on the form.
“So are you Sean. Have you ever made love before?”
“Oh sure… no,” he reluctantly admitted.
“Good. I like to break in first-timers.”
“I’m afraid,” Sean whispered. Frank turned and looked at them. Sean didn’t know if he had heard or not.

“No you’re not, you are nervous. There’s a difference. Nervousness is caused by in increase in adrenalin production from the adrenal gland. It’s usually caused doing something dangerous, or something very important to you. I’m flattered.”
“You talk like a doctor.”
“Like a biology major. I once dreamed of being a teacher.”
“Oh wow,” Sean gasped.
“Wow indeed,” She giggled and kissed him again.
“I’ve never made love to a teacher.”
“You’ve never made love to anyone, except maybe your hand.”
“Yeah,” he admitted.
“How many more?” she asked as her upskirt appeared on the screen.
“Only about three or four.”
“Good, my hand is tired.”
“Can I touch your legs?” he asked in a fit of bravery.
“Please do.”

Sean placed a hand on her stocking-covered leg. It twitched slightly under his hand. The leg was smooth, but very firm. She must work out, Sean thought as he ran his hand clear up to the seam of her skirt. He stopped there, rubbing her leg nervously.
“You can lift my skirt,” she whispered.
“Can I?” he gasped.

“Of course. The best thing about purchasing a whore, is you can do anything you want, and you don’t have to apologize for anything afterwards. I’m yours.”
“You are not a whore, you’re a woman,” Sean said emphatically.
“Thanks. That’s a very nice thing to say.”
“I… I think I’m in love with you,” Sean gasped.
“No you’re not. You are infatuated, there’s another difference. This is cause by testosterone, a word I hate, but which makes us all human.
“How?”

“It’s a male hormone, and although few know it, even women are formed by testosterone. Without it, there would be no sex drive in women. It also grows our tits and pussies. Men are driven by it. Without that there would be no sex, rape, violence… or children for that matter. I guess we need it, even if it’s detested. It comes from your balls,” she whispered, putting a hand on his crotch.

“Heeeaaa,” he yelled, jumping off the bed.
“Sit back down, it’s only a hand.”
“It’s your hand,” he gasped.
“Which is exactly like your hand, but on my body. Chill.”
“I’m so af… nervous,” he corrected after a quick look from her.
“Good. Nervousness denotes great desire, anxiety, and passion. It means I am important to you. I like that.”
“You use big words.”
“I describe grand things.”
“I guess. Can you kiss me again.”
“I can do a lot more than that, that was the last girl,” she said, dropping the briefcase on the floor.
“Rewind the tape, kid,” Frank said as he kissed Cindy’s ear.

Sean rewound the tape, while Jan slid back on his bed. He would never have dreamed that a woman like Jan would ever get near his bed. She was so amazing. He would never wash his pillow case again, he vowed as her brown hair cascaded over it. Sean quickly started the vcr and dropped the remote on the floor beside the bed.

Jan reached down and removed her panties. Her skirt slid up near her waist as she did so and Sean had a clear view of her naked pussy.
“You are much better than a sock,” Sean whispered.
“I beg your pardon?”
“Nothing. I was just thinking out loud.”

“I know what he’s talking about,” Frank laughed, then ouched when Cindy bit his ear.
Sean looked at Jan’s pussy, barely visible beneath her colorful skirt. It was magnificent.
“Do you want to go down on me?” she asked in a whisper.

“Oh yeah,” Sean whispered. He looked around at Cindy, riding up and down on Frank’s cock. Frank had his back to him, so he had an excellent view of Cindy’s right breast. It was amazing. He was mesmerized by the way it bounced on her chest. The smell of sex was strong, but not unpleasant.

“Go ahead,” Jan whispered.
Sean rolled over on the bed, landing between her open, perfect legs. He rubbed them absently as he moved closer to her pussy. It was neatly shaved, with a patch of hair above her pussy. Her lips were dark, but beautiful. His face drew near, then he suddenly backed away.
“Has anybody… I mean.”
“It’s clean,” she laughed.

“Oh. I didn’t mean…” his voice trailed off as he neared her pussy again. He put his hands against her inner thighs and pried them open slightly. She opened her legs willingly to him. He stared at them in amazement and rubbed each magnificent inner thigh. They were so smooth, so bright and flawless, like white fudge only warm against his face and hands. He ran his finger through the valley between her pussy and body. She giggled and jerked away.

“That tickles,” she giggled. He smiled up at her, then lowered his mouth to kiss the valley. She shivered at the brief loving contact of his mouth. He paused, looking at and petting her warm, aromatic pussy. He pulled her lips open and looked at the moonscape like a wonderland inside. He saw all sorts of amazing things inside. He found the vulva at the bottom of her pussy and stuck a finger inside experimentally. She gasped and arched her back slightly, thrusting her pussy against his finger.

Like a new driver experimenting with the controls of a car, Sean poked, prodded, and looked in every little nook and cranny. Jan reacted to almost everything. Sean took his time, getting a good look at his first real pussy, before he leaned down and licked it.

Jan gasped and thrust her pussy toward him. He kissed it with more confidence, then began stroking it with long strokes of his tongue. If he stroked the wrong place, Jan moved into the position where she wanted to be licked. In a moment he learned all of her favorite places.

With one finger slowly sliding in and out of Jan, his tongue eagerly lapped at her clit, and the little inverted v at the top of her pussy. They were by far the most sensitive areas of her pussy. She moaned and withered beneath his mouth. He loved her reactions. She seemed like a large, sexy cat. She withered, whined and moaned. She stroked his face, or held it against her. She opened her legs wide, or bent them behind his head and pulled him closer. At times she laid her heels on his back and humped his face with her pussy. Sean liked all of it. Of all the women he would meet in the future, Jan would be his first and most special. And she knew this. It was a special moment for her as well, because she seldom let down her guard enough to enjoy it. Now she did.

“Oh, that’s wonderful, Sean,” she whispered, looking down at his juice-saturated face. “I’m going to have an orgasm. Do you know what that is?”
“Sure, anybody who watches Showtime knows what an orgasm is.”
“Good,” she said with a twisted face, “because it can be scary the first time. I will yell and carry on, but don’t stop. I am yelling in pleasure, not pain.”
“Uh-huh,” he said, licking her pussy again.

“Oh yes,” she moaned, holding her breasts in a strong grip between her hands. “Oh, oh,” she gasped, withering on the bed. “That’s wonderful, Sean,” she said in her sexy English accent.
She simply moaned for a moment, looking down at his young face between her legs. He was eager to please, attentive to her needs and desires. He reacted to her reactions. He licked where she wanted to be licked, almost intuitively. Suddenly there was no holding back. Jan heaved up off the bed and grabbed the back of Sean’s head. She squealed in a restrained manner, while hunching her pussy against his young face. He continued licking as she had instructed. She suddenly threw her legs open wide and fell back on the bed. The fire was terrible, wonderful. She had few orgasms, so each one she did have was important.

The picture of the young boy’s face between her legs would leave a lasting impression on her, a good memory in a career where there were few. She grunted and humped her pussy against his face to the very end, then she fell back to the bed in exhaustion.

Sean sat up reluctantly. She was one fantastic woman, fun to please and heavenly to look at, but his balls hurt and he didn’t know how to proceed. He needed relief.
“I…” he paused, not knowing what to say.

“You want to be sucked and fucked like there’s no tomorrow?” she finished for him in her delicious English accent, while sitting up and stretching like a large, sexy cat.
“Yes,” he said with a huge smile.

She patted the bed and rolled off it. Sean quickly slid into the bed, sitting up with his back against the wall. Jan’s hands went to his belt and began undressing him. He shuddered in anticipation. He watched every movement she made. He took in everything at once, the afternoon light shimmering off her light brown hair, the tiny hairs on the back of her arms, as she fumbled with the catch on his levis, and the beautiful legs jutting from beneath her skirt. He had an excellent view clear up to her upper thighs. They looked like warm gold.

Her huge breasts were almost showing over the low- cut top of her blouse. He reached out and felt one, while she smiled up at him and yanked his pants off.
“Can I see them?” he asked breathlessly.
“Of course,” she whispered. She grabbed the bottom of he tight form-fitting blouse and pulled it up and over her head. Sean gasped in appreciation.
“They are even better than Mom’s,” Sean gasped.

“I don’t know, kid, I’ve seen your mom’s. She has a fantastic rack on her.”
Sean frowned. He had almost forgotten that Frank was around. Jan saw the frown and smiled, holding his face in a hand. She shook her head slightly, then leaned down and captured his hard cock in her warm red lips.

“Isn’t this fantastic, kid?” Frank asked as he knelt behind Cindy and began fucking her from behind. She was laying across the plastic desk chair with her ass hanging out. Sean looked briefly, then looked down at Jan, bobbing on his penis. He placed a gentle hand on the back of her soft hair and relaxed his head against the wall.

“Yeah, wonderful,” Sean finally answered. He looked toward the door, directly into his mother’s eyes. He froze in horror. She shook her head with a slight smile and held up a hand. She started to turn, when Frank spoke.

“All it cost you was a tape,” Frank gasped, still banging away in Cindy’s ass. “You make more tapes, and I’ll bring the girls by again. I especially want more shots of your mother’s sweet ass.”
Sean looked at his mother in horror. She seemed to be thinking. Sean was afraid that Frank had somehow seen his mother just outside the door, but that was impossible.

“No more,” Sean said, staring into his mother’s eyes. His mother remained at the door. She had turned and leaned against door sill, biting her lip.

“What’s the matter?” Jan asked, looking up from his wilted cock. “Not interested any more.”
“I was distracted,” Sean whispered.
“No problem, I will try again,” she said, briefly looking at her watch. Sean realized in horror that her time was nearly up. What if she left him…

Her lips engulfed his cock once more. She sucked the full length of his cock into her lips and tongued it diligently. Sean stiffened and closed his eyes. For the moment he forgot Frank, his mother, and everything but Jan’s sweet lips.

She sucked his cock deep into her mouth, swallowed it and continued swallowing with his cock down her throat. It was the most amazing thing he had ever felt. He had never imagined it could feel so good. It was so far above the feeling of a sock, that it barely registered.

“Oh yes, that’s more like it,” Jan whispered, while licking the head of his throbbing cock. Sean looked up and saw his mother still there, watching. Somehow it did not frighten him any longer. Maybe it was the look in her eyes, or the fact that she was watching him, not Frank. In any event, he locked gazes with her while Jan continued to suck his cock. It was a wonderful, horrible, and very memorable blowjob. It seemed surreal, except for the tremendous amount of pleasure radiating from his crotch. He reached down and held Jan’s ample naked breasts in his hands, while she again bobbed on his cock.

The fire was building. His loins boiled with a liquid fire he had never felt before. He switched gazes to Cindy, who grunted with each massive thrust of Frank’s cock up her ass. She looked at him and gave him a brief, uncomfortable smile, then licked her lips and closed her eyes. Her breasts bounced with each jerking slam of Frank’s cock. His chair bent out of shape under the pressure, barely holding together beneath Cindy’s weight.

“Oh fuck yes,” Frank groaned. “Oh shit,” he gasped, pounding even faster. Sean felt sorry for Cindy. She was not enjoying herself. She looked like she was in pain.

“Fuck yes,” Frank yelled, then stiffened behind Cindy. She moaned as he ground his cock into her unprotected ass. She grabbed the side of the chair in a death grip and winched under his brutal assault. Sean should have detested the sight, but for some reason he was turned on by it. The fire built in his balls until he whined and stiffened beneath Jan.