New Rules

It began several years ago. Shortly after John’s death. I was out for dinner with my best girlfriend, Margaret.

“Donna, honey, it’s been eight months. I know you want to keep working, and stay busy, and you love your job, but really, you should get a maid to do the housework. You could come home and just relax. Keith and I love our Sally. She cooks and cleans and everything so we don’t have to. Look. Here’s the agency’s card. Give them a call. Someone will come and interview you, then they’ll send you a girl. If she doesn’t work out, they’ll take her back, find out what you did and didn’t like, and send another one.

Maggy was right. I was over fifty. John would have been seventy three in two weeks when...... Oh, sorry...I’m OK.

Anyway, instead of a maid, they sent a man servant. Well, what the hell I thought. Give him a try.

Andrew was a few inches shorter than me. Pale complexion, light brown, almost blond hair always tied back in a pony tail. He always dressed impeccably. Conservative suit and tie, shoes brightly polished. Soon he had the condo spotless and organized. Even my makeup table had everything lined up neatly. He organized my dressing room closet, even my lingerie drawer.

Always very proper. After a few weeks I told him he could call me ‘Donna.’

“Thank you Mam.” He never did.

Then one day I was at a sales meeting that kept me on my feet all day.

I’m sure when I get home the lady at the desk calls up when I get onto the lift, because Andrew is always at the door to take my coat.

I must have sighed when I took off my shoes.

“I know what Mam needs. Come, lets get you a nice G+T while supper cooks.”

Andrew is a marvelous drink mixer. I sat in John’s favorite leather armchair. Then Andrew did it for the first time.

“May I, Mam?” He sank to his knees and lifted my left foot.

Oh my fucking Christ! His foot massages! His magic fingers never went above my ankles, but they drained the tension from my whole body. I didn’t even realize I was so tense. I don’t think I’ve been so relaxed since the last time John and I had a Sunday fuckathon. You know. Start with a before breakfast good morning fuck, then snack and make love all day long.

“You just relax there Mam. I’ll go finish making your dinner.”

“Thank you.” I whispered.

Life was better. Come home to a clean house, dinner prepared, and a foot massage.

Thursdays were Andrew’s day off. I realized I didn’t really know anything about him one Thursday in February. Work was slow and I came home early. I went to hang up my coat. I hadn’t looked in the coat closet since Andrew came. My three quarter length red fox fur was missing. Would Andrew have stolen and sold it? What else was missing? I checked my home. My pendulum diamond and ruby earrings and matching necklace were gone too. I was heartbroken. How could he? I went up to the servant’s level. His door was locked. I knocked. No answer.

When I got back to the main level I heard the service elevator door open with a ‘ding’.

I stepped back into the darkened parlor and watched the foyer.

A pretty woman with expertly made up face and light brown hair brushed down to the fur collar of my coat slipped out of it and replaced it in the closet. She wore a red and gold print dress. It has a high collar, long sleeves, and a full mid calf lengths skirt. On her feet were shiny soft white leather come fuck me boots.. My earrings were dangling, my necklace over the collar of her dress.

“Andrew! What is the meaning of this?”

He/she looked stunned as you can imagine.

“Um, er, I, ah, I didn’t mean any harm. I just wanted to, um, in the park, the new snowfall. Um?”

“I should phone The Temple of Solomon Hospital right now and turn you in.” This was back in 2021 when everything was super conservative. The Solomon was a religious prison, run by the extreme fundamentalists and funded totally by the federal government. Its mandate was to ‘cure’ homosexuals, rapists, and any sexual deviants that were ‘a threat to America’. Patients, and those cured had a fifty percent suicide rate. The Christian Fundamentalists were proud of its success rate.

Andrew was crying, his makeup running. “Please ,please Mam. I’ll never wear your things again. Please! I’ll do anything you want.”

Poor dear. I was just venting. I was relieved he hadn’t stolen from me, and I’d never turn even my worst enemy over to those monsters.

“Please, anything. Punish me, please.” He fell to his knees sobbing.

Punish him? How? He only took one day off. There was no chore too menial he didn’t already happily do. Docking his pay would mean explaining to the accountant.

“How should you be punished Andrew?”

“May I Mam?”

“Go ahead.”

He went to the closet and took the belt off my oxblood red leather trench coat. He got to his knees and presented it to me, then shuffled around and pulled the hem of his dress over his hips as he went down on hands and knees. Oh my. Not panty hose. Smooth white little buns. A flash of being over John’s knees when we played ‘naughty school girl.’ I palmed the buckle and wrapped the belt once around my fist. I took aim at those sweet buns.

Smack!

“One.” Andrew cried out. Mm. He’s done this before.

Smack!

“Two.” I was strangely aroused.

Smack!

“Three, whimper.”

His beautiful hairless buns were now glowing bright pink.

Smack!

“Four, whimper.”

This was evil. I have to stop. One more, then I’ll stop.

Smack!

“Five, sob.”

No, definitely, stop right now.

Smack!

“Siiiix, cry.”

I threw the belt onto the carpet to stop myself. So wicked. So exciting. “Put that away Andrew.”

When he stood there was a very un-ladylike tenting at the crotch level of his dress. Oh! Try not to stare. “Leave your dress on. Go fix your makeup. I’ll be in the parlor, bring me a glass of white wine, a Chardonnay.”

I took off my pantyhose, pushed the footstool to the center of the room, then sat on the couch. My mind was spinning. This was a major sea change.

I was a fat awkward little girl. Then in high school I blossomed, shooting up to five nine, and my fat went to tush and boobs. At college I earned a BA and MB. I graduated and was soon an upper level executive. Then I met John, fell in love and we married. Life was wonderful. Business lady by day, trophy bride and fuck doll by night.

Then the accident.

And now this new discovery about myself. God, I’m still tingling.

Andrew returned with my wine. His white boots replaced with scarlet pointed toe three inch heels. I pointed at the stool. “Sit.”

“So, Andrew, how long have you been wearing my things?”

“This is the first time. Honest. It was just, the fresh snow, and the park, and I love your fur, and the rubies just..”

I held up one finger.

“Do you want to keep serving me, Andrew?”

“Yes, yes. Please Mam. Please. I’ll never wear your things again. I.”

I held up my finger again.

“Good. But there will have to be rules. Won’t there?”

He looked down, humbled. “Yes Mam.”

“From now on ‘I’ will decide when you will wear your girly clothes, even on your day off. It will be a reward for good behavior. I will punish you for misbehavior. Do you agree to these terms?”

“Yes Mam.”

“Tell me, are you a faggot?”

“I guess so, Mam.”

“You ‘guess so’? You don’t know?”

“Well, I like to wear pretty things, and I like going to the gay bars and dancing, but I’ve never sucked a , um, er. Um.”

“Interesting. Do you have a name. When you’re a girl? What do they call you at the gay bar?”

“Amii, Mam. With two I’s, Mam.”

“Two. You dot the I’s with a heart, don’t you?”

Blush. Whisper, “Yes Mam.”

Another rule pops into my mind. “When you are Andrew you will continue to address me as Mam. When you are Amii, you will address me as Mistress. Is that clear?”

“Yes, Mistress.”

“Good. It’s time for my foot massage, Amii.”

####

I made him be Andrew Friday and Saturday, reminding him it was punishment for wearing my things. Sunday after supper though, curiosity got the best of me.

“Andrew. Do you have more than one dress?”

“Yes, Mam.”

“Show me.”

His room was as spotless and neat as the rest of the condo. His closet was organized with his suits on the right and his dresses on the left. His dresser was the same. Andrew’s things on the right in each drawer. The only difference was his underwear drawer. It was all Amii. Sweet bra and panty sets, sexy nighties, lots of satin and lace, even a couple of pair of boobs.

I chose a pink and black panty and bra set. Charcoal lace top nylons, and a cream angora turtleneck dress that came half way down her (I already thought of Amii as her) thighs. Her extreme, pink platform heels would finish her off just right.

“Do you have any jewellery?”

“Just my diamond studs.” Andrew pointed at his right ear.

“OK. This is what you will wear tomorrow. makeup too.”

“Thank you, Mam.”

What a nice start to the work week. Breakfast served by my very own cuddly sissy maid.

###

A week or so later I had the fur storage deliver a coat I hadn’t worn for ages sent to my work. It wasn’t age appropriate for me. I put it into a box and took it home.

“I’ve got a present for you dear. Close your eyes. Hands down at your side.” I slid the pink mink bolero with the big fox collar and cuffs up her arms. Pink and soft. “You may open your eyes.”

The smile on her face was priceless. “Oh my God, Mistress it’s beautiful!” She snuggled herself in the fur. “Is it really mine? Oh, thank you Mistress! Thank you. Thank you.”

####

“Keith’s away. Come over Friday, I’ll have Sally cook something nice.” I went straight from work.

Naturally I told her about Andrew/Amii (with two I’s).

“That’s wild. So? Which one is better in bed?”

“What!”

“Oh come on. Don’t tell me you’re not bonking him, or her.” She giggled.

“Margaret!”

“Honey, when I told you we loved our Sally, I really meant it.”

Just then Sally brought in the dessert.

“Sally, I was just telling Donna how much fun the three of us have at night.” Sally blushed. “Donna has a sissy fag maid she’s not fucking. Can you believe it?”

Now we were both blushing.

####

I’d just finished my before dinner G+T. “Amii, a foot rub, please.”

“I don’t want to.”

“WHAT?”

She ran from the room, returning in a moment with a wide black leather belt.

“I’ve been very disrespectful Mistress. Disobeying my Mistress. I should be punished. At least ten.”

She was wearing her pink pumps and white nylons. Her pink, grey and white plaid skirt just touched her knees. She wore a pale pink collarless long sleeve satin blouse. Her hair was brushed straight back. Her lipstick and nails were rose red. She bent over the back of the couch.

I lifted the hem of her skirt. Her ass crack was swallowing her thong. Her cock was escaping the frilly pink. So smooth and hairless. I stared at the ivory white buns.

“You’ve been a bad, bad girl, Amii.”

Smack!

“One.”

Smack!

“Two.”

Ah. Smack!

“Three.”

Mm. Such a gorgeous feeling of power.

Smack!

“Four.”

Smack!

Whimper “Five,”

The wicked belt is like an extension of my hand. I’m in the zone.

Smack!

“Six.” Little sob.

Smack!

“Sseeven.”

Oh, I’m getting tingly all over. Yum.

Smack!

“Eight.” Sob.

Smack!

Sobbing. “Nine.”

Her cock is as hard as a pole and dripping.

Smack!

“T..e...e..n..n.” Crying.

I know if I just touch my pussy now I’ll cum like wildfire.

“Now. My foot rub.”

Whimper. “Yes Mistress.”

Her mascara was running. Her eyes were red, but her expression was blissful. Odd.

As she massaged, I realized something else.

“You want to kiss them, don’t you Amii?”

“Please, Mistress.”

Her talented hands. her sweet lips. Her tongue between my toes! I closed my eyes, leaned back, and went with the flow.

####

Good Friday. He’s been Andrew for five days now. Doesn’t pleasure postponed always seem greater? Earned? Anticipated?

I haven’t given Amii the belt for a few weeks. I bring the little wrapped package to the breakfast table.

“This is for you dear. Go ahead. Open it.”

His eyes widen as he takes it out.

“It’s for Amii, actually.” It is a stubby stainless steel chastity device. A cock cage. “Keep those skirts down, you know.”

“Thank you Mam. I got you an Easter present too.” He went to the bottom drawer of the side board and took out a meter long, thin box tied with a pink ribbon.

In the box was a long thin black switch, with a woven red leather hand grip and wrist strap at one end and short ribbons of red leather at the other. I slipped my hand through the strap and gripped the handle. A very comfortable grip. Just the right diameter and length. I stroked the hard flexible shaft. I fondled the red leather ribbons. I stood up and gave it a swing. What a delightful ‘whoosh’ sound.

I looked at Andrew and the smile left my face. He’d unbuckled his belt and was about to pull down his trousers.

“What do you think you’re doing young man?”

“I thought you’d like to try it. Mam.”

“How dare you to presume what I’d want. In the room where I eat! Have you no sense of propriety? Just for that you will remain Andrew for the rest of the weekend. I’m so disappointed. I was going to let you be Amii.

“Monday night, at exactly nine, Amii will come to my bed chamber. She will wear her pink baby doll, the chiffon one with the ruffles. Her makeup will be slutty. Cheap whore pink lipstick and nails. Clean up this mess.”

That took self control. I really did want to beat his ass with my new toy then and there.

####

Right on time, and the prettiest little slut you can imagine.

I’d dressed for the occasion too. My ankle length white satin sleeveless night gown. The one with the plunging front, and the chiffon jacket with the white satin ruffle around the collar and the cuffs of the big, full elbow length sleeves.

On the quilted white satin comforter on my big bed I’d laid out my collection of dildos, vibrators, and strapons in a big arc with my new switch as focal point.

“Come in dear. My don’t you look pretty. Ready for your discipline?”

“Yes Mistress.” Soft quiet voice. Did I detect a bit of a quiver?

That beautiful smooth white flat chested body looked divine. Her shiny cock cage twinkled in the subdued light like a piece of sculptured jewelry. I stood and opened my arms. Amii came to me. I enveloped her gently and cooed softly. “My sweet little sissy. I’m going to beat you viciously, and you’re going to cry and scream and beg me to stop. Then I’m going to rape you with my dildos and strapons. By morning you’ll truly be my faggot sissy slut. Shall we begin?”

I stroked her hair aside and kissed her earlobe. I lifted her nighty over her head, then smoothed her hair back down. I tossed her nightie and my jacket aside. I pinched and lifted her sweet little pink nipples until she screamed. “Oh, does that hurt? “

“I don’t know why I saved John’s favorite neckties, but now I’m glad I did. Hold out your hands dear.”

I soon had her standing at the foot of my bed. Her arms were spread wide, her wrists tied to the bedposts. She looked down at my display. I stood behind her, my thighs against her buns. My voice was gentle.

“That lovely switch you gave me makes a nice addition to my toy collection, don’t you think? We won’t have time for you to experience them all tonight.” I slid a finger up the crack of her ass. I held it pushing her sphincter gently. “See the big purple one? Margaret and I used to take turns doing each other with it in college. I think it’s too big for your little virgin ass cunt though. That pink one should be a good starter cock. It’s seven inches long. You’ll soon learn to like the feel of a circumcised helmet pushing and spreading you open. We won’t need that red ball gag. These units are very sound proof. I want to hear you scream and cry.”

I reached around and cupped her girlyboy breasts. Amii was shaking. So sweet. I went to the bed and picked up my switch. I stroked and flexed it. I lifted up Amii’s chin with the red ribboned end.

“Shall we start with this?”

The End