James and Sarah Pt. 02

For the next three days... Sarah showed up exactly at 6 am, was hooked up to the machine and once his fingers delved into her pussy to confirm she was wet... he would leave the room.

That was it? 'WTF' she thought as she saw him leave on day four.

Strapped into the machine, hearing the machine hum and the soft vacuum sounds on her breasts then going home afterward to feel the ache of what was being done to them.

Finally frustrated, as she laid in her bed, she carefully rubs one of her tender breasts, her other hand slipping down across her stomach... and down between her legs trying to replicate something of what he had done to her on their first day but it only caused a small release. Nothing like her first time... just before she dozed off to sleep, she made a mental note of trying to pay better attention next time when he touched her.

By Friday, though he invited her into his office first, there on the end of his desk was two keys on a ring, "I have to leave for the weekend so there is one key to the front door and one to your room. Do NOT go into any other rooms but continue with your sessions and I will be back Monday."

"Where are you going?" asking as she scoops up the keys being curious, but when he steps up next to her... a hand he places upon her back causes a small shiver to go through her.

"Is my little cow expecting something?" leading her out she is not sure how he knew what she felt, "and It's just business," he states to answer her question as he shuts the door behind them.

Leading her up the stairs, he lowers his face near hers all of a sudden, surprising her with his forwardness "I bet if I were to check you right here... right now... I would find you already wet? Hmmm?" and she can't seem to help another shiver.

Once in her room, he motions her to the machine and as she is strapped in again, he doesn't move to turn on the machine. Instead, she feels him behind her, her legs being pushed apart and his fingers into her, causing her to feel shame as... he was right, she was dripping wet.

"That's my little cow... waiting for me to finger her and make her cum... Have you been touching yourself?" his face is all of a sudden near hers... "I bet you have my little cow."

Unable to help herself, she wiggles within her straps feeling uncomfortable with his questioning but how did he know... she can't help but look away which only causes him to give a deep chuckle.

"I thought so, then his fingers start to move up into her... feeling stretched and then pressure against her hymen... she hears a low consenting sound from him, seeing she is still intact. Fingers slip from her and he moves about to hook up the small cups again to her breasts.

Since all of this has started... she had refused every friend invite, her thoughts and life completely consumed with what was currently going on with her body and his sessions. Was she being tricked into something else without even knowing it? During the day afterward... she found herself going to the room that overlooked his property to see if she could get any more insight into this man that had lived next door to her but never seemed interested in her till now... but why now?

His voice pulls her attention back, "Today, my little cow I am going to delve into a new area..." fingers move from her pussy and all of a she feels his finger run over the little star of her ass, making her jump.

When fingers try to push at her entrance, she instantly feels pain, crying out "No, not there... please"

"We have an agreement, Sarah, though I will say," she feels him move away and a drawer is open, she turning to notice a four drawer dresser on one wall, "I wanted the weekend to introduce this to you... but as I have to leave... there will be a slight change to your session today so you will have the weekend to reflect."

Coming alongside of her restrained body, she feels his hands at the straps at her waist and notices she has some wiggle room now...

"Try that," she hears him state and finds she can arch her back, but then feels his hands at her legs... unbelting her to give her some more room. Now she finds she can arch and move back and forward a little. Last he comes back to her side, leans over to the machine and hearing a few clicks, there is more pressure on her breasts, causing enough pain to make her breath catch.

"Wwwwhat... are you gggoing.. to do to me?" she speaks between the small pained feeling she is experiencing.

Stepping from her, she thinks he is to leave again when there is a chair being heard being pulled up behind her. Trying to look to see what he is doing, her arms still restrained... it only allows her to see so far... The pressure of fingers as she feels legs being opened as far as her hips allow, then a small squeak from the chair as she assumes, he takes a seat. Fear runs down her back and she tries to pull her legs close afraid of the unknown finding she can't.

Nothing for a bit, the anticipation of something to come but unsure... causing a shiver to run along her back... then his face leans forward and she feels his warm breath between her legs... causing her to jump... hearing a low sound from her, she is unsure if it consenting, a laugh or just... him being weird.

Fingers clenched... she waits for the unknown when... all of a sudden she feels fingers part her and then... his tongue run over her sex in one long leisurely stroke.

"O... M...Goooodddd..." her brain screams out, thinking about what her friends would tell her when it came to sex... never could she imagine anything like this. The way he made her body come alive all of a sudden... it was as if he knew her better than she herself." unable to help the shudder, followed by a moan... when he does it again... as much as she doesn't want to... she pushes back to get more.

A low chuckle from him, instantly causes her shame, as she hears, "That's my cow... such a good girl, letting my machine working at your breasts to give me milk... " but she found she wanted it... she wanted that feeling again.

Then she feels the attack as fingers press into her thighs, his tongue moves up, down... dipping into her and then back up... Just when she thinks she can't take anymore... fingers move into her wetness, parts her lips... exposing her and then latches onto her nub... the hardening end that wanted more. Feeling that hesitation as if he would stop... she pushes back towards him as far as the straps allow... almost grunting in frustration as she can not go any further.

His mouth latches onto her gem and she hisses out as it flicks over, making that feeling she had been lacking... start to build. Eyes squeezed tightly tight, fingers clenching into fists... she swears she feels her toes ache as she wants that... final orgasmic moment of release...

When...

He stops and she cries out in frustration as her head swings about to see what he is going to do, praying it is not to leave her... he moves to her side... she feels his fingers dip into her wetness... and with a jump as they touch her... to her ass...

"Shit," he didn't forget..

"I am going to touch your ass... I plan to stick my cock in there and fill you at least once before your contract ends... but i'm going to say... It will hurt for a bit to feel me there," then just as she let his words sink in... a fingers pushes into the center of her star... in and out... rubbing... and next things she knows... then pressure as his finger pushes in deeper...

"NOOOOooooooo... It hurts... please..." she cries out as she is so tight and never had anything in there before.

Leaning over her body, his face near her ear... he exclaims low and huskily, "Trust me... soon enough you will beg me for this... just breathe and feel what my fingers are doing to your body... my sweet milking cow."

So clamping her eyes tightly shut... She focuses on how his fingers of one hand dip back to her pussy, while his other starts to rub and then slip into her brown star... yes there is pressure at her ass, at the intrusion of his finger holding there... but then his other hand finds her nub again... pulling away to make her push her hips back searching for more...

Then she feels him reach across from her and with a few more clicks... the pressure pulls on her breasts even more as the suction is turned up... "Ugh... it hurts..." she cries out.

"Savor it, Sarah... take it all in and savor your awakening..." then his fingers go back and like on the first day... he finds her rhythm. One hand dipping into her, then over her pussy lips... over her nub and then stroking her... rubbing... teasing... she gets lost in the moment... mixing pleasure with pain between her sex and her breasts... then just as she finds a balance... her body trying to meet fingers... quick pants... groans of pleasure... the finger in her ass she had forgotten... slips more into her... but this time... she seems to be able to take it...

Her body seems to follow his flow.. she finds she is moving between fingers at her cunt and that at her ass... moving back and forth...

The feeling in her stomach starts to build again and for a moment she is afraid... remembering the last time of how her orgasm flowed through her whole body as if lightning... but she knows she wants it and so pushes as hard as she can against her straps... moans as she is strummed like an instrument... grunts as if an animal in need... wanting what he is willing to give her... Whimpers..."yes... ppppleeeasse... yesss... Donnnn'tttttt... stoppppp" she begs

A low chuckle is heard from him again as he continues to work her over.

Then fingers pull from her ass, she feels movement behind her... something hits her ass cheeks... his legs against her thighs, "I am going to enter you... " she hears

Pressure at her ass all of a sudden... her hole being stretched as she has never felt before... it stretches... she feels instant pain and with a quick pop... his cock head is in her ass and she gives a small scream at the intrusion...

Leaning over her body... his fingers slip under her and goes back to her pussy... his voice near her ear, he whispers... "I will not move an inch... you are in control so only you can make this feel better."

Taking in his words... she tries to forget the pain at her ass as fingers play with her clit and pussy... when she is overstimulated she pulls back and it makes his cock go deeper inside of her.

"Goddddd, it is to muchhhhh" she gasps trying to find a balance... but as she moves back and forth... she finds... his cock in her ass is becoming easier...she is taking more of him in her... his fingers running over her clit... delving deep into her and then over her nub... soon... she finds she is fucking the cock in her ass...

"That's my girl... fuck that cock in your ass... take it all" and it causes her to push as up as she can... taking more of him...

Then again his voice near her... "yes... take as much as you can... my sweet girl... not even a week and you got a stranger's dick up your ass... what a slut you are."

The humiliation of his words hit her like a slap to her face... he was right, she knew NOTHING of this man... whose cock she was pushing into her body... allowing to strap her down... wanting that feeling he gave her from a few days ago... the pain at her breasts... When her body is hit with such an orgasmic release...

Screaming out the shame... the pleasure... the pain... shoving her hips up to take as much as she could... causing him to groan out in surprise... drenching his hand in cum... she feels him move back and hands grip her hips... skin slapping against skin as he starts to push in to fuck her ass... riding her orgasm as she feels him throbbing... stretching her... then... all of a sudden she feels the fullness in her ass as he cums... hearing his groan of pleasure... at his release.

He lays across her back, each taking a moment to regain themselves.

This time she didn't' pass out, laying there listening to him breath... she thinks maybe this time he passed out and so gives her time to think over her situation.

She had been fucked up the ass while tied down to a milking machine, if anyone had told her this is what she would have been doing a week ago, she would have slapped them. However, she had never felt more alive than at this moment.

Slowly he moves up and with a pained sound from her... a... a pleasured sound from him, he slowly pulls from her ass.

"If anyone had told me," he states... a hand slowly running down her back, "this is how good you would have been... I would have done this a year ago. "

Hearing him step away, she wonders where he went... when she feels a warm wet cloth run over her pussy and then over her ass to help clean her up. Once all done... she hears him turn off the machine, removes the suction cups from her breasts and then starts to unstraps her.

With help, he helps her back up and leads her over to a door where she finds is a bathroom.

"Everything," he tells her, "should be there for you to clean up" then shuts the door. Looking about he finds matching hairbrush, her favorite shampoo, conditioner and even a bit of her makeup. It almost looked like her personal bathroom at her home. Taking a bit to clean up... the only things that hurt were her breasts which she notices were red and elongated... and her ass. Wincing when she rubbed... she makes a mental note to be careful with both. Almost glad he was going to be gone the next few days.

Coming out, she found him waiting with her dress "you are okay?' he asks

Nodding to show she was, he motions to a nearby chair, not taking it... she starts to move the dress about to slip it over her head as he turns to give her a sense of privacy.

Then continues, "rules while I'm away... do no go to any other rooms. Make sure you complete all your sessions and... your virginity is to stay intact until our sessions are complete... understood?"

The last makes her arch an eyebrow but she gives another slight nod of her head.

"I will be leaving today, be back sometime Monday... if your parents ask, you are watching my cat... understood? Waiting for another sign that she understands... he notices another nod and then... helps her to the door. Stopping a moment to make one last statement, "You ass is going to be tender for a bit but will shrink back down, just don't push too hard when you have to go number two."

Opening the door, she is led out and but as she thinks of something to say, turning about... finds he has shut the door firmly behind her... leaving her to stare at it for a bit before heading home, finding keys she didn't realize she was holding in her hands.