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Chapter 109 by sipainting sipainting

Are you ready for the US Open?

Probably not, but here I go.

You are staying at the Marriott Lexington hotel in New York, across the street from the Arthur Ashe Stadium. Of course Chase has his own room. You and Mrs. Chamberlain share a suite.

For Chase, the US Open is a 14 day marathon. Fortunately, being one of the top 104 players in the world, Chase doesn't have to play the qualifying round. But he'll have to play (and win), the first, second and third rounds, followed by the round of 16, the round of 8 and the quarter finals.

That's six straight matches in a row that he has to win before you can have sex. And all matches are best of 5 sets. It is, by any standard, a herculean task.

And it doesn't start out well.

"It took you four sets!" fumes Mrs. Chamberlain in the hotel after the first round. "You wasted 5 match points!"

"At least I won, in the end," Chase mumbles. You can tell he's not happy either.

"He was just 18! How could you take so much time to put him away??"

"Sampras was only 19 when he won the whole thing," Chase points out. "Hewitt was just 20."

"You can't afford to spend so much time winning matches! Every match takes energy! Every point wears down your body! You only have a day to recover."

"I'll be fine."

"No... you will never make it to the finals unless you start winning in straight sets. You need more motivation."

"I'm trying as hard as I can! Believe me, I'm motivated!"

There's silence. Then Mrs. Chamberlain looks at you.

"Jenny, stand up. Take off your dress."

Your dress is a cute, clingy, one-piece tennis dress, with the too-short flared skirt and the scoop neckline that shows your cleavage. You know it shows your panties when you bend over, which you always do as you brush off your seat at center court to flash Chase as he's beginning his set.

You know... to keep him motivated.

Even though you're embarrassed, you don't hesitate. You stand up and take off the dress by pulling it over your head and toss it to the side, over a chair. You glance at Mrs. Chamberlain wondering what's going on. You stand before her and Chase, now dressed in just a bra, tennis shoes and, of course, the chastity panties - which were locked on by Mrs. Chamberlain that morning, and then only unlocked twice, when you both went to the lady's restroom at the stadium and then at dinner to pee, both times immediately re-locked after you had done your business.

You carefully face them so that your naked buns, showing through the cut-outs in the back of the chastity panties, are hidden,

"And your bra," she says.

Oh god. You look back and forth. Take off your bra and expose your breasts?

"You don't have--" Chase starts to say, but you hold up your hand.

You are an obedient girl, after all. You've been following each and every one of Mrs. Chamberlain's instructions to the letter. Every day you've told her how much you respect her, and how you will always be obedient.

You reach behind your back and unhook your "Dream Angels" smooth and lacy push-up bra from Victoria's Secret.

Are you really going to do this?

You let it slip off your shoulders and, eyes, closed, you toss it onto the same chair as your dress. You shiver for a bit and reflexively hold a hand over your naked breasts. You take a deep breath and open your eyes. You see Chase staring, mouth open, shocked.

"Very good," Mrs. Chamberlain says. She gets up and walks over to you. "Hands, down, dear," she says.

You drop your hands, and stare at the floor, your skin flushing red with embarrassment.

Oh god... what is she holding? Is it the punishment rod? It is!

It's a wooden rod, as thick as her finger, with a leather handle. When did she get that?? She must have packed it.

You start to sweat, knowing that she anticipated needing to punish you, and so therefore thought ahead and packed the punishment rod so she'd have it when needed.

Mrs. Chamberlain turns you to face away and then efficiently grasps your wrists and pulls them behind your back, holding them together with one hand and lifting them up, causing you to bend over, your naked buns perched out and facing right at Chase.

"Now Chase," she says, "I obviously can not punish you, but I most certainly can punish your girlfriend. She will be your 'whipping girl'. Perhaps that will give you the necessary motivation? Now, by my count, you wasted five match points. That was five chances to end the match early. So, let's start with five strokes upon her bottom."

"You can't!" Chase says. "Stop!"

But Mrs. Chamberlain just ignores him, lifts her hand up and gives you a vicious swipe across your bottom. A bright red line lights up across your bottom. The searing pain makes you cry out in agony.

Chase jumps up to restrain his mother.

"Chase, no!" you say, stopping him.

You don't know why exactly, but you know that this has to happen. All that work, over these last few months, all those times in which you knelt and sucked his cock, all those canings to ensure your obedience to Mrs. Chamberlain and to correct every one of your faults... it's all for Chase. If it stops now... then what was the point?

"Jennifer," he says. "You don't have to do this."

"Please," you say, with almost a whimper. "Just let me get through this."

"Listen to your girlfriend," says Mrs. Chamberlain. "She is a good and obedient girl."

Mrs. Chamberlain waits until Chase sits back down and then proceeds to give you four more searing strokes over your bottom. The pain of each one draws an agonizing wail and violent jerk from you. Your ass now has five bright-red lines criss-crossing it. You know that they will turn into bruises by tomorrow.

"Now turn around," she commands.

You are openly crying now, tears running down your cheeks as you turn to face Mrs. Chamberlain and Chase. Through your watery vision, you see Chase, shocked, eyes wide, staring at you. He is breathing hard.

Is that a bulge in his pants? Is he getting turned on by this?

You look closer.

OH GOD... it IS a bulge in his pants... OH FUCK...

But then you see him staring at your crotch.

Fuck, no...

Are your hips thrusting forward? Are they trying to hump the chastity panties??

ARE YOU FUCKING GETTING OFF ON THIS???

Could you really be that perverted? Are you really hot and panting from being caned in front of your BOYFRIEND by HIS MOTHER??

ARE YOU THAT SICK?

"Hands behind your head," instructs Mrs. Chamberlain.

Apparently you are. You put your hands behind your head, interlocking your fingers. This causes your chest to just out.

Uh, oh...

"Now, two more strokes for each set beyond straight sets," she says, looking at Chase. "You had to play one extra set, so that's two more strokes..."

She stands to the side and then looks you in the eye, to see your reaction...

"... on your breasts," Mrs. Chamberlain finishes.

"No!" Chase jumps up again, but you stare at him and shake your head 'no'. He gradually... slowly... backs away and sits down.

Mrs. Chamberlain carefully measures out the cane, first tapping it lightly against your breast, just under the nipple, then pulls back and gives you a slicing stroke.

You give out a long, loud scream and double over, the pain is so intense. Your knees give out and you squat into a ball.

But you continue to hold your hands behind your head.

"Stand back up," says Mrs. Chamberlain, calmly.

"Stop this," Chase shouts. "Stop this!"

Slowly, shaking with pain, you stand back up, then, bravely, you thrust out your chest for another swipe. Mrs. Chamberlain measures carefully again, this time aiming higher, then pulls back and gives you a slicing blow, one end glancing right across your nipple.

You fall to the ground, cradling your burning breasts, sobbing your heart out. You hear Chase arguing with his mother, but you can't concentrate on the words.

You just get up, snatch up your tennis dress and bra, race to your bedroom and slam the door.

You lay in bed (on your side!) and thrust your hand into your crotch, pressing the nested vibrator into your clit, furiously frigging yourself until you have a massive, painful, climax.

"What the fuck is wrong with me?" you mutter to yourself


You hear the door slam, Chase has left to go back to his own room. Moments later, the door to your room opens and Mrs. Chamberlain comes in. You are still laying naked on the bed, with no covers, because even the covers are too painful on your sores."Let me help you," she says, sitting on the bed. She unscrews a jar of ointment and then starts to apply it to the red stripes on your bottom.

Her initial touch is so painful that you burst into fresh tears.

"This should help with the pain, and also to help reduce the swelling and bruising," she says.

After a few moments, the pain subsides. The ointment starts to work its magic as she continues to massage and rub the medication into your skin.

"Mmmmm..." you say, taking a deep breath and relaxing.

"That's it," she coos, softly. "That's my good girl."

Soon she shifts to your breasts, being more careful with them, but none-the-less stroking and caressing them.

She does something on her phone and the vibrator whirs to life.

"Ohhhh..." you groan, moving your hips.

"That's my girl," Mrs. Chamberlain says. She lays next to you and kisses you on the lips.

"Ohhhhmmmm..." you hum as she increases the strength of the vibrator.

You find yourself deep-kissing Mrs. Chamberlain, your tongues intertwined.

She pushes you onto your back (OH FUCK, THE PAIN) and straddles your leg, thrusting her crotch into your hip as her leg presses into your pussy, pushing the vibrator hard against your clit. She lays against you and kisses you hard. She is demanding and urgent.

Am I really having a hot make-out session with my boyfriend's MOTHER?? you think to yourself. And am I really enjoying it???

Her thrusts become more urgent and soon you are both climaxing. For you, a purring, lengthy, flowing and long-lasting climax. For her, an urgent explosion of pleasure.

"The two of us together," she says, laying next to you. "We'll give Chase all of the structure and motivation he needs to be come Number 1 in the world."

Is all this getting too weird? Do you leave or do you stay?

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