My New Job

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A sissy girl gets a surprise.
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As well as a bit more money, the job included room and board. I was offered the job after two interviews with the counselors at the employment agency, and a face to face with the lady that was looking for a domestic.

I gave my present employer, and the landlady where I boarded my two weeks notice, loaded up my clapped out old Ford Focus and headed to my new life.

The doorman directed me to 'Visitor Parking,' then to the lady behind the desk in the lobby. "Mrs. Alberg says to go right up. Eighth floor, turn left eight oh one."

"Thank you."

"Ted, come in. Where's your luggage?"

Good looking lady. Her brunette hair styled in a pixie cut. She wore a high collar pink print silk blouse and a dove grey pleated skirt with a hem just below her knees. On her feet were two inch pink pointed toe pumps. She wore pearl earrings and two long strings of pearls lay on her generous silk covered bosom.

"Down in my car, Mam."

"You may call me 'Donna' when there's just the two of us, Ted."

"Thank you."

"So, lets show you around."

Inside the condo's double doors we were in an entrance hall. Straight ahead was a wide carpeted staircase. To the left a double door coat closet. Next to it a single door to my new apartment. Opposite, the door to the kitchen, laundry, utilities, etc. In the far corner of that was the service elevator.

"Here's the key to your apartment. This one is for the service elevator. it'll only let you go to the garage, service entrance and my two floors. Lets take it up."

Upstairs was the bedroom suite, a formal dining room, a den/home office with a wet bar, and at the top of the stairs a big open parlor.

"There, that's about it. Now I'll call security to give you a pass and a parking space. When you get moved in make us some coffee and bring it to my den and we can talk some more about your duties."

*****

I've been working for Donna for almost a month now. Nice lady. Easy to work for. Always calm when she corrects me and explains exactly how she wants things done.

As I finished serving her supper she said, "After you finish your dinner and cleaning up, bring a bottle of zinfandel and two glasses to my sitting room, and we can have a chat."

Wonder what that's about?

I went to her bedroom suite. It's sitting room was maybe twenty five feet square. deep soft dusty rose carpet, pale pink walls with flat white trim, and oil landscapes in a romantic era style. A couch and two deep comfortable armchairs were arranged around a big round coffee table. All very up-scale subtle elegance like the rest of the ninth floor.

Donna is still wearing the pastel green angora sweater (God it show off her big hooters, the way it follows her curves), and an ankle length cream linen skirt. Her soft white leather slippers are peeking out. It's what she changed into when she got home from her meetings. She's sitting in one of the chairs.

"There you are." She sets aside the papers she's reading. "Pour the wine and relax Ted."

"Thank you Donna."

"Cheers!"

"Cheers."

Sip.

"So, Ted, I must tell you I'm very pleased with your service."

"Thank you."

"Are you happy here, dear?"

"Oh yes." Mm, that's the first time she's called me 'dear.'

"Now, this is a bit awkward, You see, after I interviewed you I hired a detective to investigate you. You understand, I was going to let a complete stranger live in my home, and even though the agency vouched for you, well..."

"Oh, I understand completely."

"Good. Well... He found out things that employers are not allowed to ask."

Oh Christ, here we go.

"He had some pictures of you at the gay bar."

Oh crap.

"It doesn't matter to me. What you do on your own time is none of my business. Actually, you probably think I was always a rich bitch from a 'good' (she air quoted) family, but I had a rough start just like you, dear."

Dear again. 'Just like me?' Not fucking likely. Only queer in a small town. All through school afraid the guys would find out. Being teased about never going to school dances or asking girls out. 'Hey Ted, seen how Jeanie looks at you, Ask her out, or are you a fairy?'

"Did anyone ever tell you what a pretty girl you are when you dress up for a night on the town?"

Blush, If I could just sink out of sight right now1

"Thank you Donna." Still blushing.

"I've seen you go out on the security channel. You don't dress up when you go."

Still blushing. "No, I have my dress in my car, and change at the club. Um. Lots of us do."

"Well, dear, now you know I know, you're free to get dressed before you leave. If you'd like that is."

Still blushing.

"Thank you Donna."

*****

Once or twice a week Donna asks me to join her for a nightcap. Tonight she's wearing a retro seventies silver grey jump suit with big flared legs. She's pulled the zipper down almost to her navel. My god those hooters! They must be implants. I try not to stare. I swear she's so beautiful, she could almost turn me straight.

"Cheers."

"Cheers."

We sip and talk, then she asks, "Dear, at the club, when you're out on the town, do you have a 'girl' name'?"

Blush. "Yes. I'm 'Tina' when I'm out."

"Tina. A pretty name for a pretty girl."

Still blushing.

"Ever wish you could be Tina all the time?"

"Oh if only." Did I just giggle?

" Well, dear. May I call you Tina? Well, I want you to know this is your home, and if you feel comfortable with it, you can be 'Tina' any time you like. Would you be Tina? As a favor to me, dear?"

"Really? Really! Oh my God yes! Thank you, thank you."

*****

Next morning.

I thought about what to wear. I even dreamed about it.

My pink bra and panty set with modest boobies, Natural pantie hose. My red polka dot knee length modest neckline short sleeve dress. Instead of an elastic I tied my pony tail with a red satin scrunchie. Subtle makeup and my two inch gold hoop earrings. On my feet my white two inch block heel pumps.

"Good morning Tina. My, but don't you look pretty today."

"Thank you, and good morning Donna." Blush.

"I've a day in the city, so you're on your own for lunch. I should be home by four thirty. We haven't had fish for a while. Why don't you go to the "Fish Warf" and get something? Tuna steaks maybe? You decide."

Today she's dressed so perfectly. A cream bow collar satin blouse under a peach jacket and mid calf length skirt set. I follow to the entrance hall.

She sits on the padded bench, slips off her slippers an puts on her dark grey ankle boots with the three inch spike heels.

"My sable stroller dear."

I hold her fur for her. She pulls on her long black silk gloves and away she goes. If only I could ever look so elegant!

*****

"This snowfall is so beautiful. lets have our nightcaps in the parlor and watch it."

We sat together on one of the couches. The lights were out so we could see the snow drifting down across the lights of the city.

"This is nice, isn't it."

"Mm."

"Why don't we go out for lunch tomorrow? Why don't you wear that pretty blue print dress you wore last Tuesday?"

Oh my. Going out in the daytime? Well, I'll be with Donna.

What an afternoon! Donna took me on a shopping spree.

"Let me get you something pretty."

She bought me a pink and white plaid mini skirt with a wide pink leather belt, then we went to shoe store. Her tastes run toward extreme spike heels. Then she really blew me away.

"Lets get you a warm winter coat."

She took me into an upper end used clothing store. "Maddy, did you set the pink coat aside for me?"

"Yes, of course. Oh and that evening gown you brought in sold right away. Let me just grab the coat from the back room."

The coat was a pink fur stroller jacket, collarless with the pelts sewn vertically. Oh my God! So soft.

"Like to dear?"

"Oh my God yes. Thank you so much Donna."

"I hoped you'd like it. My pretty little maid." She stoked gently down my back. "Pink is defiantly your colour."

Then tonight after our nightcaps she surprised me again. I was just about to pick up the tray with the empty wine glasses and the half full bottle. Donna gently turned me to face her. She wrapped me in her arms and gave me a chaste kiss on the lips. "Good night Tina. Sweet dreams."

"Ah, um, thank you. Um, You too, sweet dreams."

I'm laying awake stroking myself, thinking of her kiss. Is Donna a lesbian? She seems attracted to 'Tina', but not so much to 'Ted.' That angora sweater she was wearing felt so soft and cuddly when she kissed me.

Oh! Quick, grab that handful of tissues. Mmm.

*****

For the last few nights, whether we had a nightcap or not, we've shared a 'goodnight' kiss. Oh, here's Donna now

"Almost finished cleaning up?"

"Sure. About another twenty minutes?"

"Good. Look, would I be out of line suggesting we have tonight's glass in your living room for a change?"

"No, of course not, it'd be my pleasure to host our nightcap."

"Good." She went to the landing by the service elevator and returned with a garment bag.

"I bought you a present. Something to wear around home. I'll leave it on the hall bench. I hope you like it. See you at nine thirty."

Curioser and curioser as Alice said.

Oh my! Donna you naughty girl!

It's a royal blue satin sexy maid dress. The hem is fluffed out by layers of soft crinolines four inches above my knees. It has the cutest fluffy white trim around the off the shoulder collar and the cuffs of the sweet little puff sleeves.

Well, this calls for my black 'banana sling' thong, black lace top nylons and my black four inch spike heel ankle strap shoes. I do my face and brush out my pony tail. Just my diamond stud earrings. Perfect.

"Ding dong."

My luscious Donna has brought a bottle of Paul Ricard. Great minds think alike. I'd put a bottle of Moet in the silver ice bucket and set out two flutes before I dressed.

She looks divine in an ankle length red satin robe. It's tied with a wide red sash in a big bow. Her white three inch spike heel slippers with the big pink ball of fluff over her painted toes peek out. Above the sash, her robe has fallen open in a 'V'. Her beautiful boobies are almost falling out. I try not to stare. But damn!

"Come in, come in! Don't stand out there in the cold Boss."

We both chuckle at my little joke. I've dimmed the lights so we can see the city lights.

'POP.' Out fly's the cork. Fill the flutes and hand one to Donna.

"Cheers!"

"Cheers."

"Well? Do you like your new dress dear?"

"Mm." I stroke down the liquid smooth satin. "I love it. Mm, I can hardly wait to wear it tomorrow when I do the housework. Mm."

"If you really like it I can order two or three more. Maybe different colours. There's a pink velvet one that I think you'd look so pretty in."

"Really? Then I'll just HAVE to go shoe shopping." giggle.

We sip our Champaign and contemplate the view in silence. Just a hint of sexual tension in the room.

"Here." Donna takes my glass and sets it and hers aside.

Her hand gently moves to the back of my head and pulls me to her lips.

This is no chaste kiss. Oh no. I've rarely been kissed like this.

God if only.

"Donna, I love you, but see, I can't you know, with a woman. Look, I'm a queer, I just... I mean I've tried, but.."

"Shh dear. Let me tell you a bit about myself."

Huh?

"I was my late husband Stephen's secretary. PA. Whatever you want to call it." Anyway, the same old tawdry story. Nine hours a day together. We clicked right away. Soon we grew very fond of each other. Soon we fell fell in love. He divorced his first wife and we got married."

Dear Stephen didn't just buy me this pixie nose and these big tits."

Where the hell was this going? Why's she telling me this?

"The surgeon also." She slipped the bow on her robe loose." Shaved my Adam's apple."

She smiled so sweetly and drew her robe aside. Her left hand slid up my shoulder to the back of my head, but she didn't have to push. I gladly went down and kissed her big shiny knob. I kissed it again. I wrapped my pink lips around it. What a beautiful thick cock. I pulled it out of my mouth and smiled up at beautiful Donna. She smiled back.

I kissed it again and gently fondled her beautiful velvety shaved balls. Then I swallowed.

"Mm." swallow. "Mmm." Swallow. "Mm, mm mmgh." Swallow all the way. Beautiful Donna. Beautiful cock. "Mm, mm, mm."

"Good Tina. My pretty maid. My pretty girl."

"Mm, mm." Beautiful hard cock.

"Oh! Tina!"

"Mgh." She cums, filling my mouth with her cum. "Mm."

I sit up and she dabs the dribble of cum gently off my chin with a tissue from her pocket then picks up both our flutes.

"To us, sweetheart."

We kiss and sip. Her hand slides up my stockings and strokes me.

"I suspected when I interviewed you. Then the investigator's report confirmed it. I'm so lucky you took the job, dear."

"I never suspected. I, I, I fell in love with you but was afraid, you know?"

"Shh, baby. My pretty little maid. I'll look after you." We kissed some more.

Donna pulled a condom out of her pocket and rolled it down her cock.

"Which do you prefer? Over the edge of the couch, or sitting with your legs over my shoulders?"

*****

It's been almost six months now. Donna still showers me with presents, like pretty clothes. I love being her sissy maid. I rarely have to be Ted. And my beautiful boss is a great fuck.

Tonight, just after we had a slow yummy sixty nine on the couch in the parlor, and before she kissed me goodnight and I went down to my apartment she asked me if I'd like breast implants.

The end.

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skinnysailorskinnysailoralmost 3 years agoAuthor

Anonymous, thanks for the honest critique. I should have been clearer. Donna has a big parlour, but her small sitting room is part of her bedroom suite.

AnonymousAnonymousalmost 3 years ago

part 2 would be nice

AnonymousAnonymousalmost 3 years ago

This is, without doubt, one if thebetter stories in the category. Your lead-in was most confirtable and character development so easy to accept.

Where you miss opportunity is in supporting details. Fo example: Her sitting g room was 25 feet square . . . A couch at 7X3=21, a large round tablet at 3X3=9. An upscale as you describe will have a sitting room of maybe 8X10=80. Please, watch more movies or TV series with upscale settings. Imagine true quality furnishings AND the appropriate layout for rooms or settings. Furniture takes space, and the more space the higher end . . .

The employer being transferred was, for me, expected. Where you might have these wonderful people travel, and what they might experience is so very wide open for subsequent chapters.

My only request . . . Please do not make their loving tawdry. Your development thus far is sophisticated.

I will look forward, as will others, for more.

AnonymousAnonymousalmost 3 years ago

I found the story very sensual and exciting. I also found myself imagining that I was

Tina" and taking care of Donna in every way possible

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