Using Jill Ch. 10

Story Info
Tom seeks to use an unsuspecting woman.
10.2k words
4.7
74.8k
42

Part 10 of the 12 part series

Updated 06/07/2023
Created 03/01/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
GrantLee
GrantLee
1,837 Followers

Tom's anger had not subsided, but he wanted to get his big hard-on taken care of. He would not be able to get home for another night. That would give him a great chance to get a piece of ass before then. "I need to tear somebody's ass up," he thought to himself.

He showered, shaved and got into his best looking clothes for the evening and took the hotel elevator down to the lobby. Though determined to fuck an unsuspecting young woman very hard, he had the ability to smooth out the anger when he was on the prowl. He thought about leaving the hotel when he decided to go into the hotel bar and see if the young waitress, whom he had been flirting with the past few nights, was working.

He grinned when he saw the beautiful brunette wave at him enthusiastically.

"So, Tom, you decided to stay one more night?" she asked sweetly.

"Yeah, you'll have to put up with me one more shift, Ashley," he said. He looked into her deep, blue eyes and smiled.

She smiled back, revealing her perfect white teeth.

Tom imagined what it would be like to have his cock in her pretty mouth. I'd love to face-fuck this little bitch, he thought.

Not imagining for a moment what he was thinking, Ashley turned and led him to an isolated booth. The past few nights he had been with men he introduced as his clients. The clients had acted quite inappropriately, but Tom had not, so she was glad to see him alone. Plus, he had tipped her very well over the past two nights and she did not want any of the other waitresses to be trolling to get him. If she put him in a booth like this, she could keep his tab pretty much to herself.

Tom walked behind her watching her firm ass sway sensuously in the black hot pants that she wore. "God damn, she's got a nice ass on her," he thought. The buttocks filled the short shorts worn by this college girl very tightly. The man felt his groin tighten. "They fucking spray painted those shorts on her ass," he grinned as he thought.

Her midsection was flat and bare and her breasts were large, firm and still high on her chest. They were enclosed in a small, tight shirt that tied at the front bottom, allowing for a lot of cleavage to be exposed. Below the blouse, Ashley's abdomen was exposed to a couple inches below her belly button, displaying a stomach so flat that her hip bones were outlined. "Big tits and a stomach with no fat - fuck me!" he thought. Her legs were very well defined and her smooth thighs were actually quite defined. The outfit was completed with a pair of innocent looking sneakers. It was definitely a hot outfit on a very well-built gal. All the waitresses wore the same outfit, but Ashley made hers look like a million dollars.

"Hell, what do you expect, the bar and grill is called The Bordello?"

As a traveling salesman, Tom was all too familiar with places that gave a guy a boner and lifted their wallets as they did. He spent a lot of money on clients at places like this. But he had had his share of good luck, too, occasionally getting a waitress to go back to his room with him.

"Nothing going on here except some beautiful waitresses showing off some skin for a better tip. A great marketing idea," Tom reflected, "to draw us guys in, but probably nothing more." Yet, he had gotten a vibe from Ashley the past two evenings that there may be some better possibilities. He wanted to explore that before he telephoned an escort to fuck that night.

During the next hour, as he nursed several drinks, he found out that Ashley was a student at the major university in town. Tom pried several interesting facts out about her. She was an athlete in high school and still a very avid volleyball player and gym rat. She told him that she loved swimming, running and biking and keeping her body fit. "Biking, huh? That's where she gets those damned tight thighs!" he thought.

She explained that she struggled to pay her tuition and rent and was coming up against a deadline two days away that worried her very much. If she missed this deadline, she'd have to withdraw for the semester.

She told the man that she was not ready to move back home or leave school. Little by little, Tom got her to open up about her financial situation. They discussed how dire it was and how there weren't many options left. All the while, he maintained an air of detachment so as not to raise her suspicions about his ideas. He knew that his plan had to be raised very gently. If he overstated it, she would be spooked and think he was a creep.

"Go easy, Tom. Keep that fine pussy on the line, but don't try to reel her in too quickly."

Tom kept a somewhat disinterested look about him. He watched a game on the big-screen television and acted gentlemanly when she came by. As he surveyed the bar, he knew he was lucky that it was not busy at all. "She not going to be making any money tonight," he knew. It also gave her the opportunity to linger around her best customer and talk.

Ashley had stopped by Tom's booth several times to see if he needed anything before he found out how much money she needed in two days.

"$1,500!" he repeated after she said it. He purposefully made it sound as if she needed a million. Then he drove his point home.

"Ashley, I've been very successful in my business," he lied, "and one of the things that has made me successful is my ability to view situations clearly and act accordingly. It seems to me that you have to admit this setback and make plans not to attend school this semester."

The beautiful brunette's eyes welled up with tears.

"I... I know," she said.

"Hey, hey, now. I didn't mean to upset you. There are always better ways to make money than waitressing," he said.

"I'm in college," she said, wiping away a tear, as if by way of explanation for her low paying job. "I just don't know what to do. I can't believe this is happening to me."

Tom felt his penis stiffen in his pants. "So, little miss prissy doesn't know that she's got a gold mine between her legs, huh? I've got to play this right," he thought.

"Ashley, I'm sure that you can borrow the money from your family. You need to do that. Don't be too proud to admit you need help."

"No. I can't. There isn't anyone to help me." Her long brown hair hung down to her breasts and she held the waitress tray at her side. Her toned legs seemed to go on forever. Tom glanced at the young woman's well-formed thighs and wondered what they'd feel like wrapped around his hips.

"She sure looks like she could take a good fucking," he thought to himself.

"Do you have anything that you can sell?" he asked.

She nodded negatively.

Tom exhaled audibly. He needed to make this sound very difficult.

Ashley looked around the bar and saw another table that she needed to go to.

"I didn't mean to talk to you so much about my problems. I need to go."

"No worries, Ashley. I'll try to think of something. I'm here by myself and kind of lonely, so it will give me something productive to do."

She smiled warmly at him and turned to walk away. Tom's eyes lingered on her swaying ass as she gracefully moved to the other table.

"Fuck me! If I don't get a piece of that little bitch's ass, I think I'll tear up Jill's pussy when I get home!" Tom laughed at his own thoughts. He had always said that he was doing a favor for his wife when he fucked a young, hot girl. "I'm gonna tear up the wifey's ass anyway."

He watched her glide from table to table, smiling and generating wide smiles in return from the men at the tables. Tom noticed that the women sitting with the men were not so friendly to the waitress.

She finally headed towards Tom's booth. Her movements seemed so cat-like and smooth that Tom's cock rose as he watched her.

Smiling as she approached, she said, "I didn't mean to bring you down with my troubles."

"No, please don't apologize. I've been in a bit of a funk since my wife died a couple of years ago and it feels good to concentrate on someone else's problems."

"Oh," she gasped, "I'm so sorry! Here I was just thinking about myself! I'm so ashamed!"

"Don't. Being lonely is a drag. I am a problem solver and love to help people, so this is good for me."

Ashley touched his arm gently.

"How could a man like you not be scooped up right away?" she asked.

Tom feigned sorrow by looking at his drink as he turned the glass in his hand.

"It's me. I just need to get back in the game."

"And here I am worried about my problems," she said. She let her hand linger on his arm for just a moment. Tom's cock began to push against his pants beneath the table. "She's got me so damned horny that if she touches my arm again, I'm liable to cum."

"You're problem can be solved, at least." He laughed to himself that he could be so good at lying.

"Actually, mine can't. Even according to you." Ashley's eyes looked into Tom's. They were so blue that they shone through her tanned face like sunshine. "All you need is to find the right woman."

He took a long drink from his whiskey.

"No, a guy loses confidence in his abilities with women after a while."

"You shouldn't," she said reassuring him. "You're a wonderful man."

"Well, let's stop thinking about me. I may have thought of a way to help you," he said.

Ashley smiled a youthful smile. "How? I wish I could help you, too!"

"Maybe we can help each other," Tom said.

"How?" She looked puzzled.

"Well, you've got to come up with a whole lot of money by the day after tomorrow and you've got zero prospects for doing that, right?"

Ashley nodded with a slight frown. She hated being reminded that she was about to lose everything she had worked so hard for!

"And," he continued, "I've lost all confidence with women."

She looked anxious to hear what he had to suggest.

"What... just consider... if I offered to give you that amount... don't be offended... and you spent the night with me?"

Ashley's jaw dropped.

"What do you think I am?" she whispered. "I'm not a prostitute!"

"Oh, my! There, I've done it! I'm so sorry! I didn't say you were," he backtracked. "I was just saying that this is a way to get you out of your bad situation."

Just at the worst time, a man from another table waved at Ashley for service.

"I... I...," she said with no apparent end to the sentence before she turned and walked to the table.

"Well, I fucked it up royally. But you have to give it a shot. I would have loved to tap that ass!"

Ashley seemed to avoid returning to the booth for the next few minutes. Tom finally asked another waitress to have Ashley close out his tab.

"Fuck that little bitch. She must think her pussy is worth something special. Does she think it's made of gold?"

Ashley came back with his tab and avoided eye contact. He pulled out his credit card and handed it to her.

"I'll be right back," she said. He couldn't keep his eyes off of her rounded buttocks as she walked away.

Tom waited for a very long time before she returned with his bill. He was beginning to get a bit angry, but forced himself to play it out.

When she walked back, he fumbled for an apology.

"I'm ... I'm terribly sorry," he said. "I hadn't thought this through. And with what's been going on in my life, I..." He let the sentence dangle there.

Ashley looked at him sympathetically.

He felt his penis begin to stiffen, but he held to his script.

"Don't worry," she whispered. "It's just that I get hit on all the time."

She paused as if trying to screw up her courage.

"You're from out of town, obviously, right?" she asked.

"Yeah," he said with his best dejected look. "Sorry for offending you."

She looked nervously at the man. Tom put on his reading glasses and gazed at the bill. He had a feeling that she was struggling with his offer.

"This fucking slut is actually thinking about it," he thought. He lingered at the bill as she nervously shifted her weight from one foot to the other. The tension was palpable. He was giving her some time.

Finally, as if summoning all of her courage, she spoke.

"Would you ever tell anyone?"

Tom put the pen down and looked full face at the beautiful, young woman.

"What a fucking cunt! Just an all-time stupid bitch! Well, hell! I'm going to fuck the hell out of you!" he thought.

"Of course not," he said earnestly. "Of course not. It would just be such a help for me."

"I... I don't know." The waitress self-consciously put the tray up against her chest and crossed one foot in front of the other.

"I don't blame you. Even if you would consider something that crazy, you'd certainly find someone better than me."

"No... no... that's not it. I promise. You're a wonderful man! I feel sorry about your wife and all. It's ... it's just that I've never believed that I could do that."

"What?" he asked.

"Well... be a prostitute."

"You wouldn't be. You'd just be helping me out while I help you," he said sadly.

There were a few seconds of awkward silence.

"And no one would ever know," he reasoned. He wanted to push harder but thought better of it. Ashley was clearly struggling with the man's offer. Her eyes were wide and her lips were slightly open. Tom decided to push just a bit in a different direction.

"Ashley, look, you don't need to help a guy like me. I'll be fine," he said with a look of regret.

"No, no... I'll help you," she said with some authority.

"So all it took was her thinking that she was not a whore, but only "helping" me. I'll fuck that pussy like she was a two-dollar whore! And, no, bitch, you aren't helping me. You're proving that you're nothing but a fucking slut, just like my wife!"

His mind may have thought these thoughts but his lips uttered something completely different.

"Th... thank you, Ashley," he said, stuttering on purpose, and looking at her with sad puppy eyes.

*****

Tom sat in his hotel room waiting for Ashley to come to his first floor room. She told him that her manager would allow her to leave her shift early because it was slow. Tom had stopped off at the hotel store and bought a couple of bottles of wine and a cork screw.

He had hurriedly called a couple of clients staying at the hotel with him. They couldn't believe that he was going to fuck the hot waitress that they had all be eyeing over the past few nights. When they expressed disbelief, Tom told them that he would leave a slight opening in the room's curtains so that they could watch.

These clients were older men, long past their physical prime, and Tom knew they would be amazed at his good fortune to fuck this young college girl. They were such perverted lechers that they had sat at the table ogling the waitresses and generally behaving boorishly. With no hope of ever fucking someone as beautiful and young as Ashley, they just acted like sexual perverts. They even disgusted an old pervert like Tom, but they were good potential clients so he knew that they would admire his sexual prowess.

Tom hadn't thought through what he would do, other than let them watch. "Hell," he thought, "my balcony glass will probably be cum stained from these asses! Let them get an eyeful! It can't hurt my business!"

He didn't have to wait long for the young woman.

Within a few minutes, there was a light knock on the door. Tom hung up the hotel phone and went to the door. When he opened it, Ashley hurriedly scurried past him into the room.

"I moved my car around the back," she said, "and came back though the hotel service entrance when another worker came in." She was very breathless and nervous.

"No problem," he said. "Everything will be great."

He gave her a glass of wine.

"I usually don't drink, but ... well, I'll try this," she said with a smile.

She lifted the glass to her lips and tasted the red wine. When she lowered the glass, she looked at Tom and laughed.

"I am soooo nervous!"

Tom laughed. "Don't be. Let's make this fun!" He motioned to her to sit down. She did, but very nervously.

Tom put 15 hundred dollar bills on the table next to her.

"Count it and put it in your purse."

She just looked at the stack of bills.

He nodded at it.

"Count it, Ashley. Go ahead."

Ashley counted it out. When she got to 1500, she turned to him and said, "You're amazing! Thank you!" The brunette giggled and jumped up to hug him.

"Of course. It's nothing, nothing at all. Just put it in your purse and take all your stuff into the bathroom, in case someone comes in the room. It wouldn't do for them to see your uniform here."

"Right," she replied, never wondering who would be coming into his room. "May I shower?"

"Absolutely. I just got out. I'll turn on the game."

Tom's eyes went to Ashley's firm ass as she turned to go into the bathroom.

"Goddammit! I can't wait to fuck that little bitch! She'll be a little surprised when this lonely, old widower fucks her like she's a cum slut!"

As soon as the bathroom door shut, Tom stood and arranged the video camera in his room. He had started it before she had arrived to show her accepting money and now adjusted it to focus on the area that he expected most of the action would occur - the king-size bed. He looked through the lens to make certain that it was able to get most of the rest of the room as well.

It was a high-definition camera with low light capability but he wanted to keep some lights on to make certain that the images were crystal clear.

Tom's mind wandered. "Ashley will be great to have in my personal stable, but I need to expand this a bit and be able to use this bitch to expand my business. I can't imagine how much I'd make if clients could use her."

His cock was hard now and his mood was dark. His mind turned to Jill.

"My fucking wife is a whore! Am I ever going to teach her a lesson."

The drinks that he had under his belt had not helped. He had always been a mean drunk and he was getting close to being drunk now. Even the prospect of fucking a beautiful young woman did not make him happy.

He undressed, placing all of his clothes and suitcase next to the door. Then he put the hotel bathrobe on. Pouring himself another drink, he sat in the large chair next to the bed. His robe fell open, exposing his long penis, which had now become only semi-hard, as it lay across his thigh. He did nothing to cover himself.

After what seemed to be a very long time, the shower ended. Tom waited and had another drink. "This is taking way too long. Come get some dick, bitch!" he thought.

"Hey, are you okay in there? You didn't go down the drain, did you" he shouted.

He heard a giggle and a girlish voice. "I'm going to dry my hair and put on make-up!"

"Okay," was all he replied.

"Make-up! She has no clue as to what is about to happen to her!"

The hair dryer ran for several minutes as Tom watched the game on television. He worried a bit about drinking too much and passing out before he could fuck this young beauty, but he had been a longtime hard drinker and thought he was alright on that front. He also understood himself well enough to know that he was an unpleasant bastard in bed when he had been drinking. Knowing that she would find that out this night made him chuckle.

Tom adjusted the curtains a bit to give a better view to his potential clients. He was amused by the slight movement that he could see on his balcony outside his room. The three older guys were milling out there in their nasty clothes.

"So, they doubted that I'd fuck her! Best of all, they didn't see me pay her!"

When the dryer stopped, Tom turned his attention to the bathroom door. He didn't have to wait long before the beautiful young woman stepped out nervously. She did look gorgeous, too!

Tom drew a deep breath when he saw her.

All that she wore was the thick, white towel wrapped around her body. The towel only extended from under her arms to just below her pussy. Her long, tanned legs were completely naked. Her toes and fingers were matching red color on their nails. Her dark hair cascaded down her shoulders and back to just below her shoulder blades.

GrantLee
GrantLee
1,837 Followers