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Chapter 108 by sipainting sipainting

This violation is workplace harassment! Do you stay?

Oh, yes, please, please violate me further!

You are made to stay like that for the rest of the morning as you complete your new "everyday morning cleanup" chores. This includes things like breakfast dishes, kitchen cleanup, bedroom chores like washing the sheets, making the bed and picking up stray clothes and papers and books from the night before.

"The mail?" you ask, trembling. "but won't that be..."

"... outside, in the mailbox at the end of the drive, that's correct," says Alistair, grinning.

"But..." you begin to shake, "won't people, you know, see me? In my sissy maid's outfit?"

"Yes, indeed they will," he says. "We have some delightfully nosy neighbors."

"Ohhhh..." you feel faint. You hadn't anticipated this.

"Is someone hesitating and in need of some 'encouragement'?"

Alistair grasps you by the ear and marches you over to the sofa in the living room, the same one where you were just fucked an hour ago, and pushes you over the back, pulling down your panties to expose your pert, pink bottom. Then he reaches into an end-table drawer and pulls out a long thick wooden rod with a leather grip.

"Five strokes ought to do it," he says. "BENNY?" he shouts.

"What's up?" Benny pops into the room. He's dressed now, in a tight black turtleneck and jeans. God he has a nice body. You don't wonder why Alistair fell in love with him.

"Our Jenny needs to be caned. Would you like to watch?"

CANED?? OH GOD NO!!

"Oh yes," he says, huskily. "Yes, I would. Thank you."

"We share everything, don't we, my dear?"

"Yes, everything."

"Now Sissy Maid Jenny, tell Benny why you are being punished."

"Mr. Benny, Sir, I am being punished because I hesitated to fetch the mail."

"And why did you hesitate?" asked Benny.

"Because I am embarrassed to have people see me dressed as a sissy maid."

"Five strokes," says Alistair, first measuring the distance then pulling back and giving you a slicing swat.

Oh my god it hurts!!

You squeal in pain, dancing on your toes, your breasts swinging to and fro. Alistair grasps a wrist and holds it against the small of your back, holding you in place.

And then he delivers four more searing stripes.

You moan in pain, each swat raising a bright-red line of pain across your bottom.

"Have you learned your lesson," Alistair says. He stands you up and gently dabs away your tears with a tissue.

"Yes, Sir," you say, humbly.

"Now will you fetch the mail?"

"Yes, Sir."

You gingerly pull your panties back up (so sore and hot!) and then walk over to the front door. With a couple of deep breaths, you open the door and step out onto the front porch.

It is a beautiful day. The late morning air is starting to warm up, but still holds a hint of crispness from the night before. The sun is shining. Birds are singing.

You click-clack in your high heels delicately down the walkway, and then down the drive way (which seems like a mile long!) until you get to the gate.

Oh dear, you think. The mailbox is outside the gate. You look around for a button or something, but you see nothing.

"Well hello there!" you look up, and see a smiling older man, on his morning constitutional. "Aren't you delicious. What is your name?"

"Jenny," you say.

"And what are you doing, dressed like that, my dear? Prancing down Alistair's driveway?"

"I..." you don't know what to say. "I'm... I'm the new maid," you say, finally.

"The maid?" he looks you up and down. "What type of maid are you?"

You blush so hard you feel your scalp sweating and your heart pounding.

"A sissy maid," you admit, blushing about five deep shades of red, you are so embarrassed.

"I'm your next-door neighbor and Alistair gave me a code for the gate. Would you like me to open it for you?"

"Yes, please!"

He goes to punch in the code, but then, at the last second, he stops.

"If I do this for you, what will you do for me?"

Suddenly you are wary.

"What... what do you want?" you ask, strange butterflies taking off in your stomach.

"Oh, nothing bad. How about a hug and a kiss. And a picture."

You think about it. That doesn't seem so bad.

"Okay," you agree.

He punches in the code and slowly the gate swings open.

"My name is Gerald," he says, giving you a hug. "Now how about that kiss?"

"Okay," you say, shakily.

You go to kiss him on the cheek, but at the last minute he turns to you and kisses you on the mouth! Eep!

You feel his tongue in your mouth. Yuck!

"So delicious," Gerald says, grasping your bottom and giving it a squeeze. "Now for that picture!"

He poses you against the gate and takes your picture.

"We have a community association chat board where I'll be posting this right away! I'm the president. I'm sure everyone will be so excited to meet their new neighbor!"

Oh god, nooo!!! you think to yourself. Could you blush any more? Could you be any more embarrassed? Now you'll be known in the whole neighborhood as Alistair & Benny's sissy maid! Neighbors might start watching to see if they can see a glimpse of you! They'll certainly be talking about it with all of their friends and family. You'll be known as the 'sissy maid of Glendale!'.

Quickly thanking Gerald, you fetch the mail from the box and then trot back to the house, where you find Alistair and Benny are laughing their asses off. They saw the whole thing.


After lunch (sandwiches with elegant meats, cheeses and bread), you are given a 'maids tour' of the house by Alistair. He shows you where all of the crystal, silver, elegant tableware and serving pieces are located. Already you can think of about a dozen things you want to reorganize.

Then he shows you the wine cellar where he identifies the different vintages and sections. There are the 'every-day' wines and the very rare and very expensive 'special-occasion' wines and the 'to impress the guests' wines. And then the bar area with its liquor cabinets stuffed full of bottles.

After that, you are instructed to strip and join them in the shower. They fondle your breasts and thrust slippery, soapy fingers into your bottom to make sure you are clean "inside and out". You do your duty as a maid, and make sure they are both scrubbed and squeaky clean.

You are spit-roasted for the second time that day, but this time with Alistair in back, his soapy cock thrusting deep into you, with Benny in front, thrusting down you throat.

It is pure pleasure.

After showers, you help both of the men dress. They are off to do a private gallery showing with a group of Japanese businessmen. Before they leave, you follow Alistair into your bedroom where he chooses a formal French-style sissy maid's outfit for you to wear. It is all black and white with lace trime.

"After the showing, we'll be returning with our Japanese customers for dinner, to hopefully close the deal," Alistair explains. "Now whenever anyone asks, you are to say: 'I am Sissy Maid Jenny. How can I pleasure you? Okay? Now you try it. What is your name?"

You gulp.

"I am Sissy Maid Jenny," you say. "How can I pleasure you?"

"Perfect."

While they are out, you prep the house for a dinner party. A private chef arrives, and the two of you work quickly and efficiently together to get everything prepared.

Soon, the party arrives, the Japanese are boisterous and laughing.

"I am Sissy Maid Jenny," you say. "How can I pleasure you?" This causes a lot of "oooohs" and "aahhhs" as they look at you hungrily.

You fetch them drinks. Thankfully, everyone just wants whiskey on the rocks, so that's easy. You take a mental note to take bartending classes.

And they LOVE your sissy maid outfit. They talk about it more than the artwork in the house and they are constantly fluffing up your skirts... or reaching underneath to grope and pinch your bottom (which makes you squeal with delight, which, of course, they love).

You serve dinner for everyone, which goes exceptionally well (more groping!) and during the dinner, the lead Japanese business man decides to purchase the marquis art-piece that Alistair had shown them at the studio.

"But he has a condition," Alistair says to you, in private. You are both in the kitchen. The lead businessman is in Alistair's office, looking over the contract.

"A condition?" Something in your heart flutters.

"Yes, a condition. Before he will purchase the Anish Kapoor, he wants to see your breasts-- "

"Oh, is that all? Sure!"

"--and play with them," Alistair finishes.

Oh... You think about it for a moment, and then take a deep breath.

"That's fine, no problem," you say.

"Are you certain? You don't mind me pimping you out to strange business men to help close a deal?"

"You already tied me up for one of your parties in a black catsuit, and then allowed people to cut off all my clothes for another."

"But that was different. That was performance art."

You discuss it further, but soon you are in the guest bedroom, dressed in a sissy nightgown (picked out by Alistair) and the Japanese businessman knocks on the door.

"Come in."

He enters and smiles when he sees you there. You do your best to be warm and inviting. You pull him into a warm hug, and then you give him a kiss on the cheek. You then slink back to the bed, doing your best to look fetching.

"They are... magnificent," he says, staring at your breasts in the sissy nightgown.

"The best that money can buy," you say, humbly.

He holds his hands out. "May I...?" he asks.

"Yes, *please*, you say pushing your body forward, so your breasts are in his hands.

Soon you are both moaning with pleasure, as he grasps and feels you up. You slip the nightgown off your shoulders, giving him access to your bare tit-flesh. His hands are surprisingly warm and soft.

Just then you look down and see his bulge. It is straining at the front of his pants. Seeing it makes you sad, for some reason. No man should have to deal with such a hard, aching cock like that!

"May I?" you ask, holding your hand lightly over his bulge.

You would have thought Christmas had come early.

"Yes," he says, nodding. "Absolutely, yes."

You grasp his cock, which is surprisingly large and turgid, and stroke it, lovingly. You can feel his eagerness and desire and it's contagious.

You want to get his pants out of the way, so you unbuckle his belt, and unzip his crotch, but as soon as you do, he hurries to help you, taking his pants and boxers completely off.

And as soon as you see his hard, gloriously naked cock, and then you look down and see your naked breasts, you know exactly what to do. You grab the KY jelly (there's a big tube of it on the nightstand, because of course there is) lube up his penis, and then you position him so he's straddling your torso.

He stares at you with wide eyes. Could it be true? Are you going to...

You place his lubricated cock between your breasts and then push them together, making a nice, tight, titty-tunnel for his hard member...

... and this just blows his mind. It is like he has died and gone to heaven. He tries to start slow, doing nice long, strokes, his member sliding between your ample breasts, the head peaking out from between them as it points at your face, before then disappearing again into the mountains of booby flesh, but soon he can't control himself and he's thrusting like mad and then he cums!

Oh my god, there is so much! How can one man have so much sperm?? It shoots in ropes that splatter all over, into your hair, over your chest and breasts. You quickly grab his cock, and you can feel it pulsing in your hand. You rub a thumb under the head, and with a deep, satisfied groan, he climaxes a second time! Shooting even more, this time square into your face, a heavy splat which covers one eye and goes into your nostril.

You stroke him some more and grasp his balls and he keeps shooting. The cum is dripping down your body and down your face and soaking into the sheets and into your nightgown.

Eventually, your Japanese businessman is spent and he collapses on top of you - half on you and half on the bed.

You lay like that for a couple of minutes. You are gently stroking his naked buns and legs. His seed is splattered all over you. You are a mess. The room is thick with the pungent smell of his cum.

After a second, you begin to worry.

"Sir?" you ask, softly. "Are you okay?"

After a long pause, he begins to snore.

You roll you eyes. Perfect. Just perfect. Just then, Alistair peeks into the room.

"Are you done?" Alistair whispers.

You nod your head to the sleeping Japanese who is laying on top of you.

Alistair takes in the scene, his eyes wide with delight.

"I see," he says. "We'll have the car take the rest of them to the hotel. Have a good night!"

"Wait! I have to spend the night with him?"

But Alistair has already closed the door, and you are left, stuck, underneath this sleeping man and covered with his seed.


And that's how it goes as Alistair and Benny's sissy maid. You sleep in a huge closet full of sissy clothes. You delight in wearing a different outfit every day (and Alistair buys more!). You shower with your employers. You make sure the house is clean and neat at all times - all clothes and towels and linens washed, everything put away and organized, everything dusted and polished. You a re often paddled and caned. You manage the maintenance of the property, which is a registered California Heritage site, and all of its valuable contents.

It's a full time job!

And of course, you entertain their guests and Alistair pimps you out whenever he needs to close a big deal. Some of them want a quick grope, some of them want more. You spend lots of time on your knees with cocks in your mouth or between your boobs. Some want to shower with you. And some spend the night, your two naked bodies writhing together in pleasure.

And Alistair never allows you to have bottom surgery. You are his feminine work of art - with a hard penis.

All-in-all, you are kept happy, horny, and busy. Your days are full of purpose and engagement.

And life is wonderful.

THE END (Ending 8)

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