Donna's Sissy

Story Info
Mark's feminization.
2.7k words
4.53
40.7k
30

Part 1 of the 4 part series

Updated 06/16/2023
Created 01/17/2022
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'You look lovely dear. Wearing the big girls tonight are we?

I work straight hours, but Donna has a management job without a regular quitting time, so I often beat her home.

Like she said, I wore my Dolly Parton set in my cream lace bra. My pink satin and chiffon panties were covering my steel mushroom clitty cage. After stoking my smooth sensuous natural nylons up my legs I slipped into my round toe three inch block heel pastel yellow pumps.

I put on my dove grey pleated mini skirt and my pale yellow cashmere cardigan sweater.

Donna gives me a quick kiss on the lips, then runs a finger from my lips, down my chin, across my boobs, down to my belly. With a flat palm against my crotch, she checks I'm caged.

"Have I time for a shower before dinner?"

In her charcoal pant suit and white silk blouse, wearing her spike heel ankle boots she looks severely strict and gorgeous.

"The casserole is thawed, but I didn't put it in the oven yet."

"Yet...what?"

"Yet, Mistress Donna."

"Mm."

________

It all started shortly before out first wedding anniversary. Donna and my sister went to a bridle shower for one of my cousins.

"Jean and I had some interesting conversations at Janet's shower."

"Oh, ya?"

"Mm. She told me about your parents going away on weekends and leaving her in charge."

"Ya, About once a month they'd go to 'Aunt' Ginny and 'Uncle' Mac's' for a party."

"But they lived in Woodstock too?"

"Ya. I guess they took not drinking and driving very seriously even back then."

"You never did figure it out, did you? Jean was right."

"Figure what out? Right about what?"

"Doesn't matter dear. But she told me about your dress up games when they were away."

"Ya," Was I blushing?

"But it's only nine?"

"Come."

Donna dressed me in one of her sexy nighties, then put makeup and lipstick on me.

We sucked, licked and fucked like teenagers, with the advantage of actually knowing what we were doing.

____________

Donna has showered and put on her maroon knee length dress with the pleated skirt and deep 'V' neckline. She has her red ankle strap's with the extreme spikes on her feet. Someday if I keep practicing I'll be able to glide across a room in heels as elegantly.

"Marie."

"Yes Mistress?"

"Make us a couple of vodka tonics."

"Yes Mistress."

____________

Once a month Donna goes to her company's head office in the States for a meeting.

It's Friday a few weeks after the bridal shower. Donna just got back. I'm washing up the supper dishes. I guess our talk had opened up old yearnings.

"Mark dear." That's a low growl. "Come up here. Now please."

Oh oh. This doesn't sound good.

She has the top drawer of her dresser open. Shit.

"Come. Look at this.

"See my bras? How they're folded. Why is my red lace bra folded backwards? And how did my yellow sundress get to the left side of my closet? You never, NEVER wear a dark bra with a thin material light weight dress. Ever. I never want you wearing my clothes again.

"Tomorrow we will go shopping and buy you your own dresses and lingerie. And shoes. You need shoes. And makeup!"

Boy, I'll tell you. The old Mastercard took a thumping that day. I never realized woman's clothes were so much more expensive.

___________

"You've outdone yourself Marie. That was a delicious dinner. I'll be in the den. I brought some work home."

One of the costs of being 'Marie' is I'm now the wife, and all the housework falls on my shoulders.

____________

"Mark," she said a month or so after our shopping trip, "You're getting quite good at doing your own makeup. I've made an appointment at 'Chez Elegant' tomorrow night. From now on Marcel will style your hair."

"OK?" My hair is below my ears anyway, so what the hell.

"And dear I can't keep calling you 'Mark' when you're dressed so prettily, so how about we re-name you 'Marie'?"

"Sure Hon. If that's what you want."

"And dear? When you're Marie, you will address me as 'Mistress' or 'Mistress Donna'. Is that understood?"

"But honey...."

She puts a finger to my pink glossed lips. "You don't want me to tell your Mom and Dad, or Jean and Bob do you"?

"No Mistress Donna."

"Good girl."

__________

I clean up the supper dishes and the kitchen, feeling so feminine wearing by frilly, pretty gingham 'Suzy housewife' apron. Then I go to the den looking for Donna.

"Oh fuck!"

"Like it? Tonight, my pretty Marie, I'm going to give you a loving like you've never had before.

___________

The first few times out of the house as Marie, when Mistress Donna took me shopping I was scared shitless.

One Friday night I was all ready to go. Dressed in a conservative mid calf length green wool skirt, and a hunter green blouse with my modest 'C' cup boobs.

"I'm staying home. You have the grocery list. See if there's any fresh asparagus yet."

"But, but Mistress...."

"No 'buts' dear. I know you can do it. Away you go."

While I was out Donna had changed to her ankle length crimson silk robe. "Come to the den after you put everything away dear."

"Yes Mistress."

"There you are." She patted the cushion beside her. "I'm so proud of you, Marie. That's a big step going out all by yourself. That shows you are ready to move up to the next level."

"Next level?"

"Yes dear. You've really become skilled at doing your makeup. Your fashion sense has improved greatly, and your housework is excellent."

"Thank you Mistress Donna."

"So, now I'm going to teach you a skill all good little wives need to know. Get down on your knees, dear."

"?????"

Donna stood and slipped the bow of the sash of her robe. It fell open. Under it she was wearing her red satin and lace push up bra, but my eyes were drawn to the strapon with the seven inch pink realistic cock. When did she get a strapon? She moved towards me and held the knob inches from my lips. I'd never been face to face with a cock before.

"Be a good little wife, dear, and kiss my cock."

Her hand gently stroked the back of my head as I kissed the knob.

"Lick it Marie. That's a good girl." I licked. "Now, wrap those slutty pink lips around it and swallow, baby."

I opened my mouth and took the knob in. Of course I've been sucked off so I knew what was expected. Slowly at first. The deeper and deeper I bobbed for cock. Mistress Donna's fingers gently combing through my hair.

"Good little wifie. Gobble cock like a good little slut. You're doing good."

Then with her hand on the back of my head she pushed all the way in.

"Ghh!" I gagged.

Both of her hands were over my ears and she began fucking my mouth.

"Gh. Gh. Gh. Gh."

Then she held me tight to her crotch. "Gghh!" I gagged and almost panicked.

"God I'd like to pump cum down your slutty little gullet."

She pushed me back.

"Go fix your face, dear."

Giving Mistress Donna a hummer became a regular part of our sex games.

Sometimes she's dress in my suit and tie and I'd dress as a slutty dumb school girl who'd blow her algebra teacher for a passing grade.

Other times she'd wear my work clothes and I'd either play the simple housewife who'd greet her hubby when he got home from work on her knees with a blow job, or she'd take me to the downstairs two piece bathroom, and I'd be the cheap crack whore who sucked off strangers in the toilet of the corner pub for drug money.

My favorite scenario by a long way was when we'd dress elegantly and be lesbian lovers having a slow romantic evening in front of the fire.

Christmas came along.

I opened the little gift wrapped box Christmas morning. "What's this?"

"It's a cock cage dear. Go to the bathroom, strip and put it on, then meet me in the bedroom."

"And this is the second part of your present, Marie."

It was a 'Victoria's Secret' bag with a skin tone pantie and strapless bra set

Put them on and your 'c' cup set."

Alright! Sexy.

"And here's the rest of it."

A snug maroon mini dress. It's hem was well above my knees. There was a wide band around my shoulders at collarbone height, shoulder-less and elbow length sleeves, all in a stretchy knit that cuddled my body.

See love, that's why the cage. Can't have a boner ruining the lines of your dress.

Soon it was time to go to Jean's for the family Christmas diner.

"Mistress, may I have the key to my cock cage?"

"Why?.

"Um, because I'm going to change. To go to Jeans?"

"Why? Are you going pant-less?"

_____________

Mistress Donna's new cock must have been more than a foot long. Fat and realistic (other than the size). It even had realistic balls swaying below it.

"The look on your face! If I only had a camera."

______________

January fifteenth Twenty Eighteen was a very memorable day in our relationship for a couple of reasons I'll always remember.

It was one of those crispy cold clear days where the sky was that deep blue you only get when the temperature is below minus fifteen C.

Mid afternoon Mistress said "Let's go shopping. Wear your cream knitted dress."

It's a snug warm long sleeve stretchy material. The hem is several inches below my knees. I wore my mid calf white pointed toe spike heel boots with the grey fur around the top and my red leather bomber jacket with the detachable raccoon collar. It could be either 'Mark's' or 'Marie's' jacket.

Donna as always looked gorgeous, in her black mini skirt, pink angora turtle neck, and knee high lace up soft black leather four inch spike heel boots.

She snuggled in her three quarter length red fox as I drove to the mall.

As part of my feminization I've learned the difference between 'shopping' and 'buying.' Men go to a store, see what we came for, buy it and go. Ladies 'shop'. We may or may not buy anything. We shop.

So, anyway, Donna bought a black satin blouse, and I bought a pair of red open toe block sole three inch heels.

Late afternoon we were walking past a fur boutique when Mistress hooked my elbow. "Lets try on some furs."

"Well, oh my God. Good thing I had my silver mushroom clitty cage on. It was so good trying on all the soft sensuous furs.

Then Mistress Donna bought me my very first fur coat. A knee length silver fox, with the pelts sewn vertically and a scrumptious big soft collar.

Needless to say I wore it out of the store. We went out and put our shopping and my leather jacket in the trunk of the car and went back into the mall, to the Kelsey's

where we had dinner.

Mistress said, joking, I thought, "When your lover buys you a fur, you know you're expected to put out."

I chuckled. "Of course I'll put out for my beautiful Mistress, dear."

I wore my baby doll with all the soft white ruffles. Donna, her black satin peignoir. Her strapon with the pink cock (by that time one of her smaller cocks) was laying on the bed.

We kissed, snuggled and fondled. I went down on my beautiful wife/mistress. Soon I had her shaking and crushing my ears with her thighs. I love eating her to an orgasm. Just knowing I can give her so much love.

"Since you're down there Marie." She pulled on her cock.

I kissed it's knob. I licked it. I swallowed.

"Mm,mm,mm," I gobbled it all the way to my tonsils. She likes it when I'm vocal as I suck her cock. "Mm,mm,mm."

"Good girl. Now get up here and give Mistress a kiss."

Sweet sweet kisses. As we kissed I felt the silky material of her peignoir and the breasts they covered. She stroked my chest. So romantic.

"Now Marie, my love, it's time you completed 'Mistress Donna's Feminization Academy' course, and graduate as a fully qualified wife."

"I'm fully feminized?"

"One more ceremony dear. First, put on your black six inch ankle strap heels."

"OK?"

Donna got out of bed and stroked my hair. "You're so pretty. Such a sweet girl." She slipped behind me and guided me to the edge of the bed. "Tummy down on the bed, legs over the edge, Marie." She opened the drawer on her bedside table and took out a little squirt bottle. I realized she was still wearing her pink cock. Oh no!.

"No, Donna, Mistress, please!"

"I'll be gentle. I've got this lube."

"But, but."

"Shh. Remember what I said about putting out? Now spread your legs, dear."

Donna stood where I could see her stroking the lube on her cock. "No wonder Mark finds stroking himself so enjoyable."

She dribbled some lube into the crack of my ass and began fingering it into my butt.

"Ah!"

"Shh baby."

Then it was pushing and spreading.

"AH!" the pain as my sphincter was stretched!.

"Easy sweetheart. Be a good girl for me."

"UM"1 It's knob, her knob was past. It was in.

"You're OK baby. Just relax your little ass cunt."

"Aaaa." The alien sensation as my ass was filled with cock.

"Good girl."

Oh, um, well, it was different. All the way in, then back almost out. Then slowly in again. Actually not bad, no more pain. Different.

"See Marie, not bad at all." She stroked some more. "Let's pick up the pace."

I grunted each time she rammed in 'till her thighs hit mine. "Uh. Uh. Uh. Uh."

"Ya Marie, take it. Take it all the way."

She pulled out. "Now you're the perfect little wife." Chuckle.

We snuggled and kissed to sleep.

I've developed a love for pegging. Mistress Donna pegs me as a reward when I've been a good wife. I now cum, even caged, when Mistress gives me a loving fuck.

___________

But this cock is huge. Mistress pulls me down beside her and we kiss. I'm a bit nervous about this big cock. Mistress Donna's kisses are sweet and gentle.

"Well, Marie?"

Her hand on the back of my head gently encourages me to bend down. It's longer and bigger girth than her purple one.

I kiss the knob. Mistress likes noisy lip smacking kisses to begin a blow job. Kiss, kiss. Feel those big black hanging balls. Will they swing and smack my ass when she buggers me? Kiss.

Swallow. Even with both hands wrapped around it there's to much. Just the black knob is a mouthful. Mistress is stroking my hair. Start slow I tell myself. You can do this. Little swallows. A bit more. A bit more. "Agh." It's so big. "Agh, agh." I gobble right to my tonsils. I feel Mistress Donna gathering my hair into a hand held pony tail.

What the FUCK! What's happening. I try to pull out but Mistress is holding me down. Something else is filling my mouth and running down my throat. "Gh, gh." I'm gagging. I'm panicking.

Mistress Donna lets me up and laughs. "Weren't expecting that, were you."

"Ug. Oh yuck!" I spit.

"It's the newest thing. It's got a little bottle for cum, a mini pump, a temperature sensor in the knob and a tiny processor. When it senses body temperature the processor randomly times ejaculation anytime between twenty and ninety seconds.

"It came with recopies for different flavored cum. That's why I went over to Jean's last night. we mixed up a batch."

"Jean knows about this?"

"She is my best girlfriend, silly. Of course she knows. We decided to start you on 'Natural Cum' flavor. Tastes like the real thing, doesn't it? Oh, I guess you wouldn't know, would you. Anyway Jean and I think it tastes like the real thing.

"So, go get tarted up and put on a pretty nightie. I'll reload and be right up. Isn't this exciting! The first time you'll get cum pumped into your ass/cunt.

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6 Comments
FailedscoutFailedscout11 months ago

I felt like a ping pong ball reading this story as it bounced around.

Thank you for writing and posting here.

BrittneyjessicaBrittneyjessica11 months ago

Loved it , very sexy

cdCindy1cdCindy1about 2 years ago

I want to take the "Mistress Donna's Feminization Academy" course. I want be become fully feminized and graduate as a fully qualified wife. That is my dream.

AnonymousAnonymousover 2 years ago

Liked the story but quite confusing with the scene changes .

AnonymousAnonymousover 2 years ago

Scattered around too many wardrobe items through the beginning. As the feminization progresses the focus of the story wavers, again, almost too far.

The real focus has to be Jean.

Loowing forward to a threesome here.

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