MILF Money

[badbabysitter]

Another bill, they were mounting to an insane degree.

Jessica could barely keep up with the bills she was trying to pay let alone the ones that kept coming> Her husband of 28 years had died the year before and left her with a mountain of debt. Jessica loved him dearly but he lived way beyond their means. And now what little money that was left was almost gone.

She had just turned 50 two months ago and she was too "damn old" as she thought, to find a regualr job, And besides what skills did she have outside of being a housewife.

Thats what she had been, housewife and mother to two boys, now moved across the country.Jessica was just worried howe long she'd be able to keep the house with the rate these bills were piling up.

So Jessica decided to market her only housewife skills she could. She put up fliers all around the neighborhood and in the newspaper. She found the Personals section cheapest so she put her tiny blurb there, hoping she wouldnt offend.

" Cheerful attractive middle ages lady seeks work out of home, all service negotiable, I hope you're generous"

Jessica didnt realize that when she wrote her ad what kind of minds it would actually attract and how her life would change in big ways.


--------------

Jessica Thatcher
age 50
in great shape, with bombshell curves, faded blonde hair, hazel eyes, an ample full bust

 

[wehstar]

Whilst searching the newspaper, the personals section in fact, he came across the thinly veiled advertisement for the prostitute. Dialing the relevant box number, he left a message.

"Hi. This is John. I would like for us to discuss rates. Please get back to me, I really am in need of some assistance. 555 6478."

----------------------------
John Naylor
35 yr old Engineer
Involved in some team sports
5'10, short dark hair, dark eyes

 

[badbabysitter]

Jessica nervously called the number

" Hello John?..Yes , this is Jessica, you responded to my ad..why thank you...actually you'd be my first reply..oh yes, i do offer full service..oh my rates are very affordable, i'm quite new to this you see...greek? no, I'm of german descent...oh!, yes I have travelled to greece but not in some time, but I loved it there!..oh yes, I'll be very thorough..whatever you think is reasonable... yes, of course I'm clean, but you really have to get dirty to do this job.. yes, i go right down on my hands and knees to do anything to get it done right.. excellent!!! Yes.. I can work tonight for a few hours.. yes, i'm writing down the adress..do you have any appliances you can have me use? exclellnt!..see you at 8!"

Jessica almost giggled she was so excited, she was going to have her first client tonight! He seemed very taken aback and excited too at my availablity and eagerness, she thought.

Guess she had to get huslting if she wanted to get ready on time.

She went and dressed into some nice but loose clothes, a short tshirt, which probably showed too much, and some tight jeans and tightened her hair into a braid.

At 8 oclock she had driven up to his front door, and rang the doorbell

 

[wehstar]

Well Jessica seemed too good to be true. Affordable, accomodating, and from the sounds of it horny to go with, asking for him to provide some 'appliances'; well then it sounds like he could have a show ahead of him before the feast. Very friendly, if a somewhat odd telephone manner.

He was fucking horny today, and had considered himself lucky to get someone at such short notice. It had only been a few hours after leaving the message that he had a whore lined up for the night. When John was horny his mind often raced ahead of him, and he began planning the night with the call girl. Taking out a few of the vibrators he had, he placed them on the kitchen table. First he would get her to lay on the table and masturbate with them, then he would get her to suck him off. That was the first 45 mins. Then after a short break he would fuck her in whatever hole she allowed. At least thats how he planned it for now.

When the time came, she was prompt, the doorbell rang at eight on the dot. Answering the door he was a little surprised at the maturity of the woman. But still she was attractive, in a forbidden age barrier kinda way, and blonde as a bonus. Eyeing her more than ample bust, and thinking about resting his cock between them, he invited her into the house.

"You must be Jessica. Please come in. Would you like a drink before we begin. I have been looking forward to your visit like you wouldn't believe. You had better be worth the money."

 

[badbabysitter]

He certainly was ahndsome young man, and offering a drink how delightful!

" Certainl, I suppose one quick drink couldnt hurt" she blushed entering his home.

She stepped in and looked around, it certainly was a bachelor pad , but a very nice one. It wasnt too messy and it looked the was some measure of cleaning up before she got here. Guess he didnt want to be too emberrassed.

" A very nice place" she said sitting down in the living room.

She waited from him to return and put the drink down.

" This is my first time, so how exactly do you want me to do this"

 

[wehstar]

"Really! First time! Sorry it's just that you look so experienced - but in a good way. You know, maybe you could teach me a thing or two..."

Doh. Fucking hell he was putting his foot on it, a lady never wants to asked her age, nor suggested that she looks a little older. But then is a whore a lady anyway? She's there to do what he wants, offer a 'full service', take the money and fuck off. He decided to get straight to the point, rather than dither around. He went into the kitchen, and returned to the living room waving about a 12 inch dildo in the air.

"I was thinking we could start with you tying me to the chair in the kitchen, and putting on a show for me on the kitchen table - with this! Kinda kinky, but I'm fucking horny right now."

Looking at her face, it seemed her reply might not be what he was expecting. Maybe he should have paid more attention when she said it was her first time at prostituting herself.

 

[badbabysitter]

Jessica's eyes bugged out of her head as she stared at the plastic schlong in his hand and the rather incredibly vulgar words coming out of his mouth. Her jaw dropped, and a flush rose to her face.

" I dont know.." she began to say something then stopped.

It suddenly occured to her this man thought she was a prostitute. How could have he gotten that idea? I mean she wasnt a bad looking woman, Jessica knew that, but this young man was probaly no more than 6 years older than her son!

And it had been a long time since she had been with a man...

" .. dont know.." she looked for a word" if we should go into this without discussing, ummm..expenses?"

Was she actually debating this?

 

[wehstar]

Ok so Jessica was more reserved about this than John expected from most of the other prostitutes he had bedded. She looked a little bewildered, lost for words even. But these pros were always the same, it always came down to 'if you want me to do that, then it's extra!'. She came straight back down to the issue of payment, which was wise in any case, to avoid any disagreements in value after the event.

John liked the thought of bedding this older lady. At her age, she must be financially secure, and she didn't look like a drug addict at all. There could be one conclusion - she was either married and bored, or divorced - in either scenario her motives must be for the kicks. Dirty MILF, he thought to himself. With her money talk, she was probably just going through the motions.

"Sure, of course, expenses. You assured me that you were quite affordable, but yes best to clear things up. You agreed to a few hours - I'm good for a few times over that timeframe. So, erm, what are your rates?"

John sat down next to her, taking a drink in his hands, still a bit bemused at Jessica's anxiety, but enjoying it somehow all the same. In her youth she must have been absolutely stunning, and she had surely taken good care of herself, sometimes things improve with age. He wanted a piece of her alright, and that bust was a hell of a bonus.

 

[badbabysitter]

She had no idea what the "going rate" was for an escort. It could have been thousands of dollars fro all she knew. But she decided to look at in the form of a trade. And it wasnt a complex trade after all, I guess it all depended on the difficulty of the job. And the difficulty of the client.

But he didnt look difficult. he looked easy. She smiled to herself inwarding laughing at her own entendre.

So how much for a skilled tradesworker...weird to be thinking of it in this way.

She took a sip of the liquid courage

" Thirty dollars an hour?"

 

[wehstar]

Jessica seemed to be plucking the thirty dollars figure out of the air. John grinned, right now he'd pay five times that to get his rocks off on her. But he thought he'd try to exploit the situation, see how cheap he could make this whore go. He felt kinda bad about it, but then it was like the vying for a role of dominance had began. Besides, she didn't look like she was going anywhere.

"Thirty dollars! Jeez, I thought you said your rates were affordable. I mean, I'm not saying your not beautiful, but... Well how about twenty per hour, I think that's generous, don't you?"

 

[badbabysitter]

" You're right, " Jessica said blushing, " I think I was being greedy, 20 dollars an hour it is"

She took a sip of her drink with a slightly shaking hand. She was a s nervous as a school girl on her prom night. This was getting absurd, but she supposed women had been doing this sort of thing since the dawn of time.

" Exactly how are we supposed to get started"

 

[wehstar]

"Exactly how are we supposed to get started"

"You'll be telling me your a virgin next."

John took her drink and put it down on the coffee table next to his, before standing up, the dildo again in his hand. Putting it down on the arm of the chair she sat on. If she wanted to take it, it was there. Stood above her as she sat, he thought they had might as well get straight to business.

"Well, I'd like you to be as kinky and as dirty as you can tonight. But maybe you could start by unzipping these pants?"

 

[badbabysitter]

" I dont know about kinky" jessica giggled, " i dont know much about kinly, whatever you'd call that"

She flushed as he stood before her. Then she tentaively reached out

" I cant.." she said pulling her hands away..then she reached forward again and with trembling hands undid his fly and unzipped him. She closed her eyes and pulled down his pants, and nervously opeend them when she heard the slacks hit the fllor.

" Oh my.." she said looking at her new friend

It was so proud and jutting, and smooth seems this young man had shaved. She had trimmed herself, but that was only because she picked that up during her college years inthe 70's. But this was very smooth. It had been a while since she saw something like this, a big mans big cock in fron of her. Her hubby was 10 years older than her, and she hadny seen a hard on him since the begining of the Clinton administration.

She reached out and and gently wrapped her fingers around it. Very hard, very smooth, very nice, and slowly began to stoke him even firmer

 

[wehstar]

Proud as a cockeral is probably the most apt description for John as he stood before her, analysed her obviously very genuine reaction. Yes, this really was Jessica's first time at prostituting herself, he even wondered about the complete virgin thought too, given the wide eyed fascination she seemed to have with his piece.

Tentative at first she stroked him, building in both confidence and application. Jessica seemed to be concentrating thoughtfully upon his cock, John had to like it.

"There you go. hmmm, this is nice."

He looked down at her face, it is true she could easily be one of his mother's desperate bored friends. There was something about that thought that made his erect penis twitch, springing to life and out of her gentle grasp for a second. That said, she had kept in shape real good, still a very desirable sexual target.

John stroked at Jessica's long blonde hair, so that he could look into her eyes.

"You see. It's easy. Please tell me you like it."

 

[badbabysitter]

She smiled a bit looking up at this young man. She wondered what his body looked like under that shirt, his hips and legs were certainly strongly built. She leaned a bit forward on the edge of the couch and and softly took the tip of his penis in her mouth

* This is it*Jessicamused to herself* I'm officially a prostitute* And the funny part was, she didnt mind at all. This was actually exciting.

She gave it a soft kiss, and then another, and then wrapped her lips around it, giving a firmer full suck when she had it cased between her lips. She caught the taste of his precum on her lowerlip, and breathed softly though her nose.

God, how she had missed being with a man

 

[wehstar]

John's hands moved from her head, as he lifted his hands up Jessica's little t-shirt whilst she began to take his hard member in her mouth. She sucked on him exquisately, taking more than half in her mouth at times. As she sucked, it felt so fucking good as she breathed. Lifting the bottom of that T-Shirt up to expose her breasts, he cupped and kneaded those handfuls with vigour.

 

[badbabysitter]

Jessica had to confess, she was really getting into this. It had been a long long time so she had been with a virile man. She had forgotten the taste of skin, the velvety hardness. The steady throbs of lust,

Jessica was swabbing her tongue on his underlegth as she swallowed the young man more and more. The she felt his hands reach down to pull up her shirt, and his hands went quickly to her breasts. Rubbing and squeezing her even with the cups in the way.

* in for a penny..* she mused

Jessica reached behind her, while keeping a firmlip lock on her "clients" memeber and unhooked her bra, letting her 38DD's land firmly in his hand.

Ohhhh, skin on skin..this is what she missed

 

[wehstar]

So there he was, in his living room pants around his living room, with a sexy MILF whore taking his massive erect cock as deep into her mouth as much she comfortable could. She had seemed a little uncomfortable at first, but now, well lets just say she seemed to be warming up.

As he toyed with her jumbos she elegantly removed her bra, tossing it to the floor.

"Oh baby. That looks sweet. But hey, don't stop there, I really like what I see."

She was getting into it. John thought to himself, it is probably like swimming or riding a bike, all comes back to you easy enough. There was something about the way Jessica was acting, he just assumed that it had been a while.

John unbuttoned his shirt, slowly revealing the fruits of all his gym-work to the hungry Jessica before it ended up on the floor along with her t-shirt and bra.

 

[badbabysitter]

Oh she was definitely NOT going to stop now. She looked up at him with big eyes when he undid his shirt. Yummy, a hot young athletic body.She began to slurp more earnestly on his thick member.This was turning out to be a very good day.

Hell, she thought for a moment, I should be paying to have sex with him.

She slipped her lips away from his glistening cock and smiled up at the younger man.

" Do you think we should find some place for us to lay down"

 

[wehstar]

It felt good as she sucked harder on his piece, he heightened his own pleasure with a few little motions, fucking her mouth just a little, a little precum probably seeping into Jessica's mouth.

"Lay down? Hey, standing up, lay down, on the floor, on the table, in bed...whatever it's all good. Maybe up to my room would be best though, comfy."

John lifted her from the seat, those lovely orbs moving closer to his eyeline before he held her body close to his, pressing their naked torso's together as he kissed her lips and neck. As John worked on Jessica's neck, feeling her hands and nails on him, he looked down and felt her shapely ass in those tight fitting jeans.

"Let us go upstairs then, ladies first."

He held her by the shoulders guiding her to the staircase, where his followed her swaying butt closely with his eyes as she made her way up followed by the lustful, yearning younger man.

 

[badbabysitter]

She was led willingly upstairs, scarcely beliving this hot buff young men wanted her,Not only wanting her, but paying her for it.

The bedroom door was open and the bed itself big and sumptious.

She sat down a bit nervously on the edge of the bed and smiled tentalively.She began to unbutton her slacks

 

[wehstar]

As Jesssica sat on the edge of the bed, undressing more, John stood at the doorway in his naked state.

"Hey lady, don't be shy - you can lay on the bed or whatever. I think I'll just admire you a little while, whilst I watch you get naked. A big bed like that, a naked lady looks good on it you know. And smile, you are enjoying yourself aren't you?"

He leaned against the door, stroking his big erect manhood in his hand gently, looking at her with wide consuming eyes.

 

[badbabysitter]

" Oh I certainly am" she smiled leaning back onto the bed.

This was going to be interesting, she thought.

She unbttoned her slacks and pushed them down her hips, kicking her legs into the air , she made sure she gave her young man friend a look at her upturned derrier and her now rathering moistening temple of lust.. She crossed her legs in the air and kicked the slacks off. And peeld off her panties in rather the same lasicivious manner.

Now she lau naked as the day God made her, she carressed her self from her in-thighs to her breasts, which she cupped for a monent, then stretched her legs wide again.

She eyed his throbbing member, turned on by the sight of such a buff man pleasuring himself to her form.

" What else do you want to do with that? " she all but purred.

 

[wehstar]

As she lay sprawled on the bed, legs wide open invitingly, John squeezed himself as he watched her professional looking seductive strip. * If only I had a pole * he thought to himself, more thoughts entering his mind about retrieving the dildo he had left downstairs, perhaps a prop would improve the show.

What else do you want to do with that?

"I was thinking about shoving it deep into your pussy..." he replied as he wandered over her. She lay on the bed, he stood at the foot of it as she teased him. He took a leg in each hand and pulled her legs to a vertical position, her ankles resting beyond his head over his shoulders, her ass lifted off the bed as he quickly entered into her pussy.

"I bet a mature woman like you knows a few tricks you could teach a young man like me. Oh fuck yeah." The pressure on his cock could be felt as he lifted her ass a good six inches off the bed, looking down at her body, the position enabling a good deep screw.

 

[badbabysitter]

Jessica let out one HELL of a scream when John climbed un top and unceremoniously speared her. Foreplay was a dead art to this young man, but he sure didnt need it.

My god it had been ages! His thckness ripped it into her like Moses parting the Red Sea.

He stopped loooking down at her as she caught her breath, her chest heaving.

She smiled up. Yes, this was it.


" Its okay... harder, please"