Sweet Reluctance

"I suppose," she said dubiously.

"Okay, here we go," Taking my hands, I placed them on my chest. "Tammy, do you think I'm attractive?"

"I..." she frowned. "I'm not sure I should answer that."

"Why?" I prodded, "You afraid to hurt my feelings?"

"No, but I know you and like, you're older and..."

I rolled my eyes.

"You're losing your flattery points!" I laughed, and then said, "Looks aren't about age Tammy, someone is good looking or they're not. Now, let's try it this way, picture that you don't know me or how old I am or anything like that, you see me in a club what's your first thought?"

"You..." she looked away and said softly, "I think you're a nice looking guy, you're in good shape and you have those blue eyes and a great smile." She stopped and still not looking at me sighed, "Josh, can I talk about why I'm here now?"

"A deal's a deal," I told her, "Go ahead, hon what can I do for you?" More importantly what will you do for me?

"Remember I mentioned a few days ago that I needed money for next semester?"

I nodded, fighting to keep a neutral expression on my face as my fantasy became one step closer to reality.

"I've asked everyone I know and no one has that kind of money. I tried the banks, but I don't have any credit and I..."

She trailed off and now that I was assured of my chance to play the game, asked softly,"Tammy, are you asking to borrow a thousand dollars?"

She stopped and to my delight I saw her lower lip began to tremble. I was going to say something soothing to let her know it was open, but before I could, she blurted out,

"Mr. Daniels I know it's a lot of money and I have a lot of nerve asking, but my Mom and Dad don't have anything and I don't know anyone else!"

She stopped and I had to pause, to insure that I could sound hesitant.

"You're right, that is a lot of money."

"I know it is," she said softly, "But I'll pay it back, I promise I will!"

The lip was trembling again and I paused to savor that delicious sign of how upset she was. Letting out a deliberate sigh, I shook my head.

"I don't see how, you don't make a lot of money," I shrugged. "I would be waiting a long time to get it back."

"I'll figure out a way, I'll get a second job!" she said, her voice beginning to crack.

"You know Tammy, maybe you could just take on-line courses for a semester, and you won't need as much aid so you'll be covered." I fought not to smile when I finished. I already knew how the system worked.

"But if I don't go to classes, I'll lose my student housing and then I won't have a place to live!"

Putting her head down, she looked up at me through her long eyelashes and whispered, "Please Mr. Daniels? I'll have to leave school and go back home!"

My cock, which had calmed down as we had been speaking, immediately rose to attention as I looked into her distraught brown eyes. Not for the first time I wondered if there were something wrong with me, but as always shrugged it off, there was nothing wrong with a game of give a little get a little.

"Here's the thing Tammy," I began quietly. "I know you would try to pay me back, but you would end up in trouble that way as well."

"What do you mean?"

"Think about it, you don't make a lot of money and you do have to pay some rent and buy food, put gas in your car, if you have to pay me back so much a month where does it come from? If you pay me you'll be falling behind on other things."

"Well," she frowned, "Maybe I can clean your house every other time for free until it's paid off." She nodded. "That would be a hundred a month."

"But then how will you live without that hundred?"

Tammy paused and undaunted, continued her effort.

"I'll get a second job and use that money to pay you off."

"And lose time from your studies," I pointed out. "Part of your aid is based on grades I'd imagine, so again this could affect you negatively."

"Well..." she started, but I put my hand up to stop her.

"Tammy understand something, I've made a lot of money as a financial planner. I make that money by telling people what they can and can't afford to do. You can't afford to borrow this money. It will end up causing as many problems as it will solve, understand?"

She looked at me and another sick surge of excitement went through me when I saw those big brown eyes filling with tears. Tammy looked as if she were going to say something, then stopped and stood up.

"You're right I guess." She said, bravely trying not to cry as she spoke. "Thank you for at least thinking about it."

"Tammy, I..." I started, but she went on.

"I'll let you know when I'll be leaving to go back home so you'll have time to find somebody to replace me."

Turning, she began to walk away towards the front door. I let her get a few steps away, to make it seem as if I was thinking and took a moment to admire the backs of her well-toned calves. When she was halfway to the door I called out, "Tammy, I never said I wouldn't help."

Tammy stopped and turning around, looked at me, a small smile on her lips and her eyes now wide with hope.

"You can help me?"

"Well it will be up to you, if I can, but come sit, and we can talk about it."

Her smile widening, Tammy walked back to the recliner, but I raised my hand.

"Come sit here." Leaning forward, I tapped the leather ottoman that was a couple of feet in front of the recliner.

"Over there?"

"Yes, I'd like to be a little closer while we discuss this."

Tammy shrugged and coming over, sat down in front of me. The ottoman was only a couple of feet high and the perfect height for her to lean over and...

"I didn't mean to upset you Tammy," I began, focusing on it getting to that point, "All I'm saying is that I can't see how we could do this as a loan. That doesn't mean we can't work something out."

"I'm not following," she said. "You said there was no way I could repay you."

"Right, but that doesn't mean that I couldn't give you the money."

"You....you're going to give me a thousand dollars?"

"Yes." I said simply, then putting my finger up added. "But understand that nothing in life is free, so I am going to expect you to earn it."

As I spoke I wondered what her reaction would be. To me the statement was pretty obvious, but Tammy did seem a bit more naïve than the other girls I had done this with. When I finished she looked confused.

"I offered to clean for free and you said that wouldn't work."

"It won't," I resisted the urge to smile. She really was that innocent. "But I was thinking that there is another service you could provide that would allow you to repay me."

I gave her a wink and sat back, waiting for her reaction.

"I don't know what I could do for you besides clean," she shrugged. "But whatever you have in mind, I'm sure I can do."

This time I did smile. I really was going to have to spell it out for her.

"Tammy?"

"Yes, Mr.....I mean Josh."

"I want you to ask yourself something."

"Okay." She leaned forward, bringing herself even closer to where I ultimately wanted her.

"What do you think a good looking older guy like me would want from a pretty young lady like you that would be worth that kind of money?"

Tammy looked as if she were still confused and started to speak. She then stopped and my smile broadened when her eyes widened.

"You..." she shook her head, "Are you saying that you want too...." She trailed off, but this time I wasn't letting her off the hook.

"Want to what?" I asked.

Swallowing, she whispered, "You want to have sex with me?"

"Exactly," I nodded. "I've wanted you since the first time I saw you Tammy, and bad enough to hand you a thousand dollars in cash right now."

"But... but that's prostitution!"

Unable to help it, I burst out laughing.

"Oh, Tammy," I exclaimed, once I could stop. "You truly are precious. Maybe it is, but I consider it more a business transaction. You want something from me; I get what I want from you."

"I...I can't." she shook her head. "I'm not like that. And you said you liked that I was a good girl, why would you..."

"I also said that good girls are more fun when they act bad." I reminded her. "I get it," she said laughing nervously, "You're kidding, this is like a test or something." "Does this look like I'm kidding?"

Uncrossing my legs, I put my hand down on my stomach to draw her attention between my legs. Not only was the bulge in my jeans obvious, but I had been so excited that there was a small wet stain visible where my dripping cock had soaked through the material.

"Oh my God!" Tammy said, comically bringing her hand to her face.

If she had blushed before, it was nothing compared to the beet red color her cheeks quickly turned. Reaching into my pocket, I removed a roll of hundred dollar bills and showed it to her.

"This is a real offer Tammy."

"I... I can't believe you would want this," she stammered. "I thought you were a nice guy."

I smiled at that, and then shrugged.

"I am a nice guy Tammy, most guys who pay for sex shell out a hundred bucks, I'm offering you ten times that because that's what you need and I want you to stay in school," I smirked, "Don't you want to stay in school?"

"That's not nice at all." She said and to my delight her lips pushed into a pout, "Or very fair."

"Life never is." I told her. "But unlike many girls in your position, I'm giving you a chance to help yourself. This is a more than fair offer Tammy."

"But you could be nice and let me earn it another way and..."

"Okay, so maybe I'm not so nice, but what I am is the only person who can help you and I'll be more than happy to, after you help me."

"I...I'm not a slut Mr. Daniels." Tammy said shaking her head. "I feel bad you think I am."

"I know you're not a slut Tammy." I told her, leaning forward and trying not to smile as she leaned back. "That's why I want you, I don't want what everyone else has had, I want a good girl."

"A good girl wouldn't do this." Taking a deep she shook her head and said "I won't do it."

"Okay." I told her, slipping the money back in my pocket, "Maybe you can get it somewhere else."

"Even if I can't, I won't be a whore." She said indignantly.

Standing up, she continued.

"And I don't think I should come back here and clean, I... I don't feel right about being here anymore."

"Well that's your choice Tammy." I said softly, "Best of luck to you."

"Thank you." She nodded and turning away took a couple of steps towards the door.

I frowned, wondering if she were really going to walk out. So far I had never had a girl turn down my offer, but maybe I underestimated how good Tammy was. As she walked slowly away, I wondered if I could try to change the offer to just a simple blow job. No, it would most likely be all or nothing with her and it was looking like I was getting nothing. I looked down at my crotch, resigning myself to the prospect of jerking off rather than getting the real thing. It then hit me that I hadn't heard the door. Looking up, I saw Tammy had stopped halfway to the door and was standing there with her head down.

Turning back around, she slowly walked back towards me. Her head was down and I felt my heart begin to pound when she sat back down on the ottoman. Bringing her head up to look at me she asked softly, "Would it only be once or would you expect it every time I came to clean for you?"

"Just tonight." I assured her, feeling my again begin to rise. "Like I said it's a very fair deal."

"I...don't want to." She said, her lower lip trembling, "But I...I need the money."

That could not have been said better! I swallowed hard and shifted slightly to give my aching cock more room. Tammy made it ache even more when, her brown eyes looking into mine, she asked, "Are you really going to make me do it?"

"I'm not making you do anything Tammy, you either will or you won't, choice is yours."

"I just don't understand why you want me to."

"Because you're young and beautiful." I told her.

"You could get sexier women than me." She said. "Besides I...." looking down she whispered, "I'm not really very good at it."

"Oh, come on now," I laughed. "You're nineteen Tammy, you know how to have sex."

"I've only done it with one guy, and he said I wasn't very good at it."

"That's okay," I said quietly, "I'll tell you exactly what to do."

She didn't respond and I continued.

"See Tammy, I love that you're innocent, that you're not some easy little pig. The fact that you don't want to is exactly what I want. I live to see good little girls like you act like nasty little sluts."

"I'm not a...."

"We've talked enough." I cut her off. "I promise that it will just be once, and that I won't hurt you, but I'm losing patience. You can act like a little girl and leave, or you can earn what you need."

"Please don't be mean like that." She asked, her lip trembling even more.

"Then act like a grown up." I snapped, even though she was acting just fine for my tastes.

Pulling the money out, I slowly counted out ten hundred dollar bills and put them down on the coffee table. Tammy looked at the money, then back at me, before taking a deep breath.

"O....okay Mr...."

"For this you'll call me sir." I told her. "Now take off your blouse."

"But...."

"No buts Tammy, time to act like the bad little girl I know you can be." I pointed at her chest "Now take that off and show me those pretty little tits of yours."

She looked at me and my cock swelled seeing that not only were the lips trembling, but her brown eyes looked as if they were filling up.

"Do I..."

Rolling my eyes, I reached out and made to pick up the money.

"Okay!" She said.

Reaching up she began slowly unbuttoning her blouse. I saw that she wasn't go slow to tease, but because her hands were shaking and her fingers fumbling with the buttons. I sat back in the chair and smiled as she worked her way down the blouse. When she reached the last button, I noticed she was holding the shirt together. Putting my hands up, I mimed opening my own shirt. Lowering her head, Tammy opened the blouse, exposing a cute pink lace bra.

"All the way off."

Tammy nodded and I said. "Say yes sir."

"Y...yes sir." She said softly as she slid the shirt from her shoulders and dropped it to the floor

I licked my lips as I took in her soft creamy skin and admired how good her black hair looked against it. My eyes trailed down to her tits, "Now the bra."

Tammy didn't move and I sighed loudly.

"Okay, why don't we just forget this, I'm not going to keep repeating myself."

"Sorry sir."

Putting her arms behind her back, Tammy unhooked the bra and as she started to pull the straps down her arms I said, "Look at me when you do it."

After a brief hesitation, she lifted her face and I could feel my cock oozing at the look of shame in her eyes. As good as her eyes looked; I dropped my gaze to where her trembling hands were sliding the bra off. I let out a breath as I set my eyes on the most adorable set of little tits I'd ever seen. They were even smaller than I had imagined, not a whole lot more than a mouthful, but they were perky, perfectly round and featured nipples so pink I could barely see them against her skin. Part of why I could barely see them was that they weren't erect. The fact that she wasn't turned on fed my fire, but before I pushed further, I breathed out.

"Tammy they're beautiful."

"They're...little." She whispered.

"They're perfect just like you." I assured her. "Now show them to me."

"I...I am showing them to you." This came out in what could only be described as a frustrated whine that sent a shiver though me.

"No Tammy," I cupped my hands and lifted them. "Show them to me."

"I...yes sir."

Tammy obediently placed her hands under her tits, lifted them slightly. I took a moment to savor the sight of her pink fingernails on her white skin, before saying, "Now play with them."

"I...I can't do that." She shook her head. "I won't."

"Fine." I said and reaching over to the stack of money took one of the hundreds and tossed it at her feet. "Then get dressed and leave. I think a hundred is fair for a look at your tits."

She looked down at the money and whispered, "I...I'm not a whore."

"Today you are." I said simply. "But not for money, but your future. It's sex or dropping out of school. Now play with those pretty little nipples of yours or go home and start packing."

"Please." She begged her brown eyes shining, "I don't..."

She stopped as I pointed at her shirt.

"Get dressed and..." I stopped as placing her hands back on her tits, Tammy started rubbing her thumbs over her nipples.

" "There you go Tammy," I said approvingly, " Just like that."

"Yes sir." She said in a barely audible whisper.

I watched transfixed as her pink nipples hardened. I noticed each one of them turned up slightly and my mouth began to water at the thought of what I wanted next.

"Stand up."

Tammy slowly stood up and I was thrilled to see that she was still fondling her nipples. Sitting up straight, I beckoned to her with my finger. Putting her head down again, Tammy stepped forward and I found my face inches from her tits. I reached for them, but she quickly stepped back.

"Mr...I mean Josh," she began. "I really don't..."

"I'm not going to give you another chance Tammy." I said firmly. "Come back over here and the next time you stop we're done. You've had those little tits sucked on before and you know it."

"But he was my..."

"Your what, boyfriend?" I laughed. "Give me a break, sex is sex whether you think they love you or not. Trust me, I'll be a lot better to you than some frat boy, that is if you grow up and get over here."

"I...yes sir."

She stepped back up to me and replacing her hands with my own, I let out a breath as I cupped them. Tammy looked away and I could feel the tenseness in her body while I gently squeezed her firm tits. My heart pounding and my cock throbbing, I took her hard nipples between my fingers and began to roll them between them. Tammy gasped and as I continued to lightly toy with her perfect nipples I noticed she had begun to breathe heavier.

"Does that feel good?"

"I...I guess so I... ow!"

Tammy let out a delicious little yelp as I gave her nipples a light pinch.

"It's yes sir, remember?"

"Please don't hurt me sir!" she pleaded. "Please don't be rough with me."

"Let's try again." I managed to get out as my own breathing was picking up. "Does that feel good?"

"Yes sir, it does."

"See, I knew you were a bad girl."

"No, I'm..."

"Letting me play with your tits for money." I smiled up at the distraught look on her face. "I think that's pretty bad don't you?"

"I...yes sir." She whimpered.

"Good girl." I told her and leaning closer, flicked my tongue across her right nipple.

Tammy gasped and pulled back, but before I could speak, leaned forward again.

"You're learning." I said softly. "Such a good bad little girl."

I gave her nipple another quick lick, before sucking it into my mouth. Tammy gasped again as I began sucking on it while my fingers played with the other. I swirled my tongue around her swollen flesh and fought not to moan in pleasure at the feeling of her young firm tits in my hands and mouth. I switched nipples, getting another gasp from her as I started sucking harder than before. Tammy was breathing through her mouth and my already rock hard cock seemed to expand even more as I swore that those breaths were mixed with a couple of faint moans.

Continuing to enjoy her nipple with my tongue, I let go of her tits and sliding my hands down her soft flat stomach reached around her waist, to remove her skirt. Finding the zipper I slowly pulled it down, and this time lost the battle, emitting a moan around her nipple when she whimpered as I unzipped her. Moving my hands back to her hips, I tugged on the loose fitting skirt and easily slid it down her legs. Once it was past her knees I let it go and as it fell to the floor, placed my hands on the back of her tight calves. I sighed around her nipple when I felt her legs were trembling and began slowly sliding my hands up her smooth skin.