Young waitress needs the money

[Gareman]

OOC: This is a closed thread for LilAshley and myself

Jake Tanner 5'11" a little on the stocky side, 48 years old (not much to look at really)

IC:
The diner was busy. Business had really improved since the new truck stop had been completed, just down the road and I couldn't be happier. Carol, my best waitress was running things up front and I was helping out in the kitchen where needed. Every little while I would take a peak and make sure everything was going okay and also to get another look at my latest hire.

I really hadn't intended on hiring any more waitresses, but I guess I made this decision with my cock instead of my brain. When she had asked me about work, I really had planned on taking her application and stashing it with the others I receive on a regular basis. College kids rarely stayed long enough to become productive, so I stopped hiring them years ago.

But when she explained her situation and how much she needed the money, I guess I found a soft spot in my heart for her (or more acurately a hard spot on my pants).

God she is cute....and so naive....

 

[LilAshley]

Ashley

Ashley:
5' 7 115lbs blonde with green eyes and firm 34b chest
In desperate need of money to pay off my huge student loans before I get too far behind.

I just applied for this waitressing job and got it on the spot, I wasn't expecting to get the job that easily. But hey, I wasn't going to complain.

I slipped into the my tight little white uniform and started waiting on my first table. I was so excited I hadn't even noticed I didn't button the top few buttons on my uniform well enough and now that had come undone. Exposeing my chest and a little of my white lace bra.

 

[Gareman]

I watched Ashley as she moved around the diner. She seemed oblivious to the eyes that followed her, as each guy took a long look. The woman also looked, but their eyes reflected jealousy; including the other waitresses.

As the evening wore on, I stopped her several times to correct small things I felt she could be doing better. Her apologetic response to each small criticism told me that she was going to be a "good soldier" and her obedience was exactly what I was counting on.

At around 8:00 I sent a few of the waitresses home and continued to keep a close eye on my new hire. Several young guys tried their best lines on her and I was impressed with her ability to extract herself from each situation with class. Obviously with her looks, shes had to learn to deal with those things on a daily basis.

Finally it was closing time and I held Ashley back to help me close up. The obvious excuse was to review her performance, but I knew differently and so did Carol. She gave me dagger eyes as she headed out the door and I just gave her a little wink.

"Okay Ashley," I said as she came back into my small office. "For your first night you did pretty well, but I do need you to pick up the pace if you are to stay here for very long."

I watched her expression and saw exactly what I had hoped to see. There behind those pretty green eyes I saw fear and desperation, a combination that would definitely work well for me...

 

[LilAshley]

Ashley

I worked pretty hard all night, trying to make my first night a good one to impress everyone there. I think I ended up making a few of the other waitresses jealous, but that was something I was used to by now. I really pissed off Carol when Mr. Tanner asked me to help him close up, but it wasn't my fault that he asked me to help and not her.

"For your first night you did pretty well, but I do need you to pick up the pace if you are to stay here for very long." Mr Tanner told me.

I stood nodding my head, wanting so badly to have his approval and to make sure he knew I was capeable of doing great things here. "Yes Mr. Tanner I know, I'll do everything I can to work harder and be a good waitress here for you" I commented.

Hoping he would see that I had some potential. A little afraid that he might not and put me back out looking desperately for another source of income.

 

[Gareman]

Her nervousness was apparent and I played upon it as much as I could.

"I know you will Ashley," I said seriously. "I just wanted you to know that I run a pretty tight ship and I can't keep anyone who isn't working out."

I could tell that my words were having an effect upon her and decided to get a little more information while I had her in her vulnerable state.

"By the way," I continued. "Why is this job so important to you? You seem to really need it."

I study her as she formulates an answer. Her legs are my first point of interest. The short uniform reveals everything from mid-thigh down and I really like what I see. Thin, but still shapely and wouldn't I love to slide a hand up betwen those soft thighs to her young pussy.

Noticing my gaze, she fidgets slightly and then begins to speak...

 

[LilAshley]

Ashley

"Why is this job so important to you? You seem to really need it." He asked me. I felt his eyes on me like a pair of greasy slimy hands. They seemed to just undress me right there on the spot. Normally I would slap a guy or just walk off letting him think about me more. But this wasn't an option. He was my boss, the boss of the job I needed severly.

"Umm this is really important to me because I'm quite a bit in debt here. If I don't start paying now they are going to kick me out of school and then I'll have nothing at all to look for in my future." I replied. Letting him stare, what the hell did it matter it was just another guy gawking at me I figured.

 

[Gareman]

As she spoke, I continued scanning her young body, imagining that she was standing before me totally naked. I was sure that she knew exactly what I was doing, but frankly I really didn't give a shit.

"That is really a pretty difficult situation," I replied, stroking my chin as I locked my eyes onto her breasts and held my gaze for a fairly long time. "I hear those schools can be real pricks about not receiving their money on time. Can't your parents help you out until you can get your feet on the ground?"

Again my eyes wander and I focus on her nice legs, allowing her to see me gawking at them.

"I mean I would never leave a daughter of mine in a lurch," I continued. "God knows how many unsavory ways there are to make money these days, if the situation warrants it."

Smiling a rather leacherous smile, I wait for her response, knowing my words were making her very uncomfortable...

 

[LilAshley]

Ashley

Shifting me weight uncomfortably. "Umm well, they don't really help me anymore. Ever since I took off from home and moved out here." I replied. Feeling very embarassed almost ashamed of how I have let myself be in this situation. This boss of mine just gawking at me, knowing what kind of things he must be thinking about me right now. I've never slept with someone I didn't want to, or for a job or money or anything. I just didn't know what to do right now, I felt so vulnerable.

 

[Gareman]

I stood up and moved around the desk.

"You know Ashley," I said gently. "I may be able to float you a small loan to help you with those debts. Of course you'd have to pay me back."

Her eyes reflected a mixture of excitement and skepticism, my offer sounding too good to be true.

As I stood just a few feet away, I could make out the sweet scent of her perfume and it made me want her all the more.

The quiet was deafening as she contemplated my offer, only passing cars breaking the silence briefly. My eyes continued to undress my young employee and I waited eagerly as she stood before me.

 

[LilAshley]

Ashley

"I may be able to float you a small loan to help you with those debts. Of course you'd have to pay me back."

"Wow really? You could do that for me?" I asked in suprise, knowing how much that would help relieve some stress from this money situation. Not even thinking about the second half of how to pay him back "Thats wonderful, I'd really appreciate that very much"

 

[Gareman]

"How much would you need?" I asked, enjoying her naive excitement over my offer. "Would a couple grand help?"

I wait for her response and begin to think of the wonderful ways my little friend could repay me. I was certain that she would have a difficult time maintaining an apartment, going to school and trying to find a few extra dollars to pay me back. On the money she would be making at the diner, she'd be lucky to make ends meet.

The leverage that our little business deal could give me would be tremendous. There would be no recourse but to do exactly as I ask. And boy would the interest payments be high!!

 

[LilAshley]

Ashley

"a,a a couple grand" I said trying to keep my jaw from dropping. "Yeah that would definately help me out a ton." Thinking about al the bills I could take care of with that money right now. "That would be just wonderful, now just what do I have to do to repay you?" Starting to wonder just what this could entail. Not wanting to let him know, but I'd give just about anything for this.

 

[Gareman]

"Just what do I have to do to repay you?"

Her words encourage me to continue. I walk over and place my hand on her shoulder.

"Well Ashley," I answer. "A beautiful young woman like yourself has an awful lot to offer a guy like me."

Her eyes widen, the realization of what I'm suggesting making it's impact.

"You know...one hand..." I allow my hand to move down her shoulder to the top button on her uniform. "...washes the other."

She swallows hard as I open the button and move closer...

 

[LilAshley]

Ashley

I looked down at his hand, unbuttoning my uniform, then back up to him."You know...one hand...washes the other" he says to me. I know what he is thinking, or at least I think I do.

"Well I understand what you mean sir, but isn't there another way?" I ask him. Not stopping him, just hoping for another possible solution to this.

 

[Gareman]

My heart pounds heavily as I realize that she is not about to fight my advances and I continue to unbutton the front of her uniform.
As each button releases I get a better view of her young breasts, covered only in a white lace bra.

"Isn't there another way?" she asks naively, eyes nervously watching my hands.

I ignore her question and undo the final button. My hands part the front of her uniform and gently grasp her small firm breasts.
Turning her slowly, I guide her back a few steps until she stands up against my large wooden desk.

"That's it Ashley," I say softly. "Be a good girl and we can find you a way out of your financial bind."

 

[LilAshley]

Ashley

I watched as he finished unbuttoning my uniform. I gazed at his hands as they moved in and caressed my breasts.

"Be a good girl and we can find you a way out of your financial bind." He said as he pushed me back into his large desk.

I felt like I no longer had control or a say here. "Yes sir" I said nodding as I looked up to him. Not sure what he was going to do next, or what he all had planned here.

 

[Gareman]

Her soft words of compliance are my cue to continue. She lies back on the desk, propped up by her elbows.

Pushing the soft material of her uniform over her shoulders, she lifts up each arm in-turn and allows me to remove it. Reaching behind her, I unsnap her bra and she also helps with it's removal.

"That's it Ashley," I say softly. "I think we're gonna have no problem working out a deal that will satisfy both of our needs."

The look of surrender/fear in her eyes, was magnificent. So young...so innocent...so vulnerable.

 

[LilAshley]

Ashley

"I think we're gonna have no problem working out a deal that will satisfy both of our needs." He said to me. I looked to him with a sexy little smile, letting him know I was going to let him take control over me.

"Well as long as I get what I want" I say as I lean against the desk.

 

[Gareman]

As she lies back, I slide my hands up her thighs. Finding the elastic of her panties, I slowly slide them down her soft legs and over her white sneakers.

Dropping them beside the desk, I place my hands on the insides of her knees and part her young legs. Moving between her spread thighs, I lean forward and begin to gently fondle her small breasts in my large hands.

"That's great Ashley," I encourage, allowing one hand to open the front of my pants and remove my hard cock...

 

[LilAshley]

Ashley

I let him slide my little panties off and to the floor. Stepping out of them as I look down to watch him undo his pants. Pulling out his huge cock my eyes gaze on it. Then looking up to him in question.

"What, umm what do you want me to do with it?" I ask, knowing that I have to do as he says.

 

[Gareman]

Her question surprises me. Maybe it's her willingness to comply, all my other waitresses resisted at first.

Standing back, I look into her young eyes and reply.

"Why don't you kneel down right here," I say pointing to the floor directly before me. "I think you can figure things out from there."

I watch as she lowers herself from the desk and drops to her knees, knowing what is about to happen will be worth any loan I can possibly extend to her...

 

[LilAshley]

Ashley

I nod my head in agreement as I slowly drop to my knees right before him. As I look up I see his dick right in my face. I reach out and start to stroke it. Then I lean in, licking the head. Wrapping my lips around his cock and starting to suck it into my hot mouth. My hand at the base stroking lightly as my head works its way down his cock slowly. Sucking hard down it then sliding back to the top and off his cock, making a loud popping sound. Then taking it back into my mouth and going down again and sucking him hard.

 

[Gareman]

The warmth of her sweet young mouth on my cock is fantastic, as she takes me inside. I watch her, intrigued by the vision of my thick penis sliding between her soft full lips.

"Mmmmmm," I moan, taking her head in my hands and pulling her down onto my throbbing meat. "Oh yeah Ashley, I know we can work out some arrangement....mmmmmmm....yeah....just keep sucking my cock, sweetheart."

Slowly, she slides up my penis and flicks her tongue against the underside of my sensitive cockhead. Her lips leave a trail of saliva down the full length of my prick and again she lowers herself, my hands pulling her down to again take my hard tool deep into her throat.

"Oh yeah...that's it," I continue. "Suck it Ashley and I'll take real good care of you."

 

[LilAshley]

Ashley

Moaning softly on his big cock as he tells me to suck it. Looking up at him with my big green eyes as I keep swallowing his hard sick. My head sliding up and down the length of his cock, sucking all of it in and out of my hot wet mouth. Making sure to lick and work the bottom of his cock with my warm tongue.

 

[Gareman]

Her hot mouth feels great and I know I won't be able to hold out very long. Grasping her under her arms, I raise her from the floor and push her back up against the desk.

"That's my girl," I encourage, as I open my top desk drawer and take out a condom. Last thing I need is to knock up one of my waitresses...with all the lawsuits these days...

Stripping away the wrapper, I expertly slide it over my ready cock and push her onto her back on the big wooden desk.

"How would you like a nice big cock inside that sweet little pussy," I ask, spreading her smooth young legs and moving forward. "Just lie back and enjoy it sweetie....that's right."