For the Love of Money

How far would you be willing to go in pursuit of wealth, even if only temporarily? And how much would it require for you to give in to your baser impulses? I had a story I liked from years ago that played with this idea on literotica, and decided to make my own piece toying with it as well. Can't find it now, so hard to credit it, but...felt like it was worth mentioning that the genesis of this piece was the story of another author's work.

***

The waitress caught my eye from the moment she first approached. It wasn't a fancy restaurant. No, just a local pizza place mainly staffed by college kids looking to find what extra cash they could. She was pretty tall, at roughly 5'10, and in great shape. She wore tight, faded jeans that were about as form-fitting as possible. These presented her curvacious ass in the best possible light. She wore an overly tight t-shirt as well with some small logo on it. Was that the style now? It held the colors of the local college mascot, and was so tight I could just make out the outline of her bra under it. Her hair was long and a lustrous shade of auburn held back in simple ponytail. Her eyes were a brief shade of green. She was vivacious and engaging, but I wondered how outgoing she would be when pressed.

"Was there anything else I could get you tonight, sir?"

I slid her a crisp, hundred dollar bill. I suppose I should note that the bill at this point was under twenty bucks. Her eyes didn't register the shock I expected. Hmm.

"Ah, and keep the change."

Ah, there it was. Someone paying with a large bill didn't necessarily mean they were tipping with it – eh?

"A-Are you sure?"

"Yes, but I'd like to ask you a couple questions. Maybe just a slight bit racy. Would you indulge me?"

She nodded quickly. One could nearly see the dollar signs overtaking her eyes and all thoughts. Maybe this would be easier than I thought. Still, if she was too willing there wouldn't be any fun in corrupting her. She left briefly to close out the tab and pocket her tip. The place was mostly empty, and would close in maybe an hour. When she came back there still a slight smile gracing the corners of her lips. How resistive would she be?

"What's your name?"

"I'm Ashley. What's yours?"

"Chris. Well, Ashley, I have some questions to ask you. First, tell me about the lingerie you're wearing."

Her cheeks flooded with color at this point. She pushed away from the table slightly, but didn't leave her seat. Her eyes glanced at me, down at the table, and then around her.

"...why?"

"Because you're a beautiful young woman, and from the blush in your cheeks maybe a bit more innocent than I realized. Also, I have a slightly lingerie kink... So I figured it would be sexy to know. Besides, it isn't like I'm asking you to blow me under the table."

She chuckled, slightly at that. She was still very uncomfortable and blushing to the highest degree. However, she had taken the tip. You could see that weighing in against her modesty and embarrassment.

"...I really like Pink. You know, at Victoria's Secret?" I nodded and she continued, eyes glued to the table and not moving. "I'm wearing stuff from that. A black thong with white hearts and lace edging, and a simple push-up bra that's just black"

"Hmm, you like matching I see. It sounds deliciously sexy. Thank you for telling me. Now, how about you sell me your lingerie right now? I'll pay you, hmm, $200 for both. I'm fairly certain you can replace them easily and pocket a nice profit from that. How about it?"

She didn't immediately walk away. Nor did she snap and tell me off, demand I leave, or rush to her manager. Her eyes glanced at me with shock, but shock could be worked with. We could edge her around her own fears. Flat-out rejection or taking too much offense at the offer would have been more challenging. Hmm. Well then, maybe she is still a little innocent. This might be quite fun.

"I...I couldn't do that."

"Ashley, tell you what. We'll make it $300." Her eyes glanced around, uncertain where to rest. "Also, Ashley – you don't have to take them off in front of me. How about this, you walk to the restroom, take them off, and simply come back and hand them to me. $300 for something that simple. How many nights would you have to work to make that much?"

She swayed uncertainly in her chair and, finally, stood up. This would be the moment of truth. If she wouldn't cave on such a simple demand I'd never get her to cave on more challenging ones. Still, as luck would have it she headed straight to the lady's room. She came back, blushing uncontrollably, and handed me the articles under the table. After handing her the additional $300, my fingers traced the inside oh her panties and detected the slightest hint of wetness. Glancing down, I saw her bra size as 34C. Oh, this was too perfect.

"Ashley, how about we go out briefly tonight and see if I can't help you some more?"

"I'm not some hooker, Chris..."

"I don't think you are, but I think everyone can be tempted to act a little differently with the right motivation. I just want to see how motivated I can get you to give in to some naughty desires. Nothing horrible, and you can tell me at any point you're done or want to stop. If you do, we'll be done. Anything that happens, you'll have to agree to. If not, I'll be glad to drop you off at your dorm and call it a night. Deal? You've got a couple minutes to decide, but you could easily walk away with a couple thousand dollars. You're already at, what...$380 or so?"

Her eyes reflected uncertainty, and darted back-and-forth with her internal debate. Was the temptation good enough for her? Well, to force her decision I shrugged and headed for the door. My hand touched the handled, and I turned it. As I stepped through the door she spoke again, probably more loudly than she meant to.

"Wait, Chris. I...just let me tell my manager I'm leaving early."

In moments she was nervously following me to my car. I started it and drove to a nearby, empty parking lot. She was nervous and silent, but still...she had come.

"So, Ashley. The next offer is to buy your clothes. Yes, all of them. I want to see you naked, but no – I will not touch you at all."

"I – I could never do that. I'm not a stripper."

"I'm not saying you are, Ashley. But are you sure you wouldn't do it for any price?"

"I..." Her voice trailed into silence.

"You can't say it, because you know better. How about $250." She stayed silent "Hmm, $500." She looked up but was biting her lower lip.

"O-okay."

"No, dear. Now its back down. $400, then? Answer faster next time..."

She quietly stuck out her hand while nodding. So, I handed her four more crisp bills. She grabbed the bottle of her t-shirt and pulled it slowly over her body. Her pale skin came into view, and her bright, pink nipples were hard, and clearly displayed in the little moonlight entering the car. Her jeans came off with more difficulty, but they did come off. I took both and threw them into the backseat. My eyes enjoyed the view, and noted her legs and pussy were flawlessly shaved. Mmm.

"Okay, now some questions. You answer, and I'll pay you...$25 per answer. But you must answer honestly, and immediately. Okay?"

She nodded, silently. Her discomfort was still apparent, but her nipples were hard and she was responding more quickly with the threat of payments lowering.

"Are you a virgin?"

"No."

"How many men have you had sex with?"

"...four."

"And given head to?"

"...nine."

"Do you like giving head?"

"No."

"Do you swallow?"

"Only if I really like the guy, and even then rarely."

"What's your favorite way to get off?"

"Using my little vibrator."

"Guys don't do it for you?"

"Most high school guys don't know what they're doing, and most college guys are only concerned with their own orgasm."

"Do you ever finger yourself?"

"...sometimes."

"Well, Ashley, that would be eight questions. Another $200 for you." I handed her money and she added it to the wad of bills she was holding. However, without clothing she had no where to put them. "Now then, Ashley, how about $1000 if you can make yourself cum in the next 10 minutes?"

"I-"

"Hmm, that wasn't a yes. Make it $800."

She didn't answer now, but on hand flew to her pussy and began fingering herself with two fingers. Her wetness was clear from the sound and the speed with which she played. Her thumb carefully teased her clit, while her other hand caressed her breasts. At first her caresses were gentle, but before long they had erupted into something more fierce. She managed to fit a third finger in, and the car was beginning to smell of her delicious scent. Her eyes were closed as she was lost to focusing on her own pleasure and the thoughts of money it could offer. I unzipped my pants and pulled out my cock, stroking with pace of her fingers. Honestly? This entire time I had been madly horny, just with the thoughts of trying to corrupt some random girl. I was nearing orgasm quickly as she began to moan softly, her body shuddering as orgasm overtook it. Hm. Nine minutes. Well done, Ashley. Her eyes opened and she saw me stroking.

"I'm about to cum, Ashley. If you let me cum in your mouth I'll double your reward up 'til now."

Whether it was the slow caving building up her tolerance to what she would accept doing, the remains of her own orgasm tempting her to indulge my own, or just the dollar figures being offered – she did. She took my entire cock in her mouth and her head bobbed up and down with expert ease. Before long I was firing strand after strand of cum down her throat. She tried to pull back, but I spoke immediately.

"Pull away or spit out a drop and no doubling of what you've made so far."

Her movement stopped. Indeed, her lips fell down to the base of my cock and she seemed to be sucking it like the droplets of cum were the only source of her sustenance. After this, she sat up uncomfortably and looked at me, expectantly. Her eyes clearly asked 'what next?'

"Good girl, Ashley. You're doing better than I could have hoped." I handed her the remaining funds. "Next, let's go to a good college bar and see what we can find to do next."

$1,960 down, but a good start to the night...