Jill's Punishment Pt. 01

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When will she ever learn.
1.1k words
4.27
6.5k
9

Part 1 of the 2 part series

Updated 04/09/2024
Created 03/24/2024
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"No. I told you a week and it's only been five days."

"O.k. Sorry."

I was about to start my Saturday morning chores, wearing shapeless grey sweats and sneakers. My 'Jill' clothes are all locked up in 'her' bedroom.

See, at work I'm Jack, a middle management go-getter. The rest of the team and I went out to celebrate. The client was very pleased and took us all to a high end bar for a drink after work.

How was I to know my wife, Margaret, would ask her mother and sister for dinner?

At home, you see, I'm Jill. Her sissy maid/wife. Being Jill is my stress relief. When Marnie is mad, she doesn't beat me, you see. She denies me my 'Jill.'

See, she's an Alpha, and as soon as we met, she recognized me as a Beta. She actually asked me out for our first date. Telling me where we were to go, and that I was paying. When she first told me she wanted to see my apartment, well, that's where she found Jill's clothes.

After we were married a few years she told me she was going to date other men. She gave me the choice of accepting that, or divorce.

********

The first time she brought a date home, I was shocked.

Then she said, "Jill, have you ever sucked a cock?"

"No!" Well between you and me, a few times long ago, before Margaret.

"Well, let me show you how."

She pulled out Chad's big bone and got to her knees. I ran crying from the room.

The next night after work she had me install a locking door knob on the spare bedroom and move all Jill's clothes in there.

"You embarrassed me so much last night. I usually don't suck cock on a first date. That's why I brought Chad home for you to suck off."

A hellish week later she forgave me and unlocked Jill's room, so I could wear my pretty clothes again.

********

"I have a date tonight. You'll have to make your own dinner."

I was wearing my knee length short sleeve pink floral print dress and three inch heel pumps when they came home.

"Jill, Jake and I need a glass of wine."

"Yes dear."

When I brought them their wine they said 'cheers' took a sip, then Margaret pulled Jake's cock out.

"Come here dear." I obeyed. "On your knees and be a good girl. Show Jake what you've been doing with my strapon."

Oh, crap. I kissed his knob.

"That's a good girl. My good little sissy. Swallow all the way, dear. Good girl. All the way."

"Gh. Gh. Gh. Gh."

"Good girl. Good sissy slut. Such a pretty cock sucker. Good little sissy."

"Mm, mm, mm, mm."

"I'm cumming!"

She grabbed my hair and pulled me back. Jake squirted all over my face. I tried to get up, but her grip on my hair was strong.

"Where do you think you're going?" she said softly.

With her left hand still gripping my hair, she used her right index finger to scoop the cum from my face and hold it to my lips. "Good girl. Lick it up. Lick up all that yummy cum. Good girl. You like the taste of fresh cum, don't you sissy?"

I was crying from the humiliation.

"Good girl. Now go to your room."

********

"Erin and I are going out after work, so I won't be home 'till late."

I wore my new bronze satin and white lace bra and pantie set, my bronze satin bow collar blouse and narrow pleated knee length charcoal skirt. Panty hose and two inch block heel ankle straps completed my ensemble.

Just before nine the two of them rolled in, laughing and giggling.

Erin shrieked with laughter when she saw me. "Maggy, Jill is absolutely adorable tonight!"

"Why thank you darling. Jill, go change into your teal maid dress. Quickly now."

It's very sissy, with it's white satin trim and short fluffed out hem. I knew my stubby cock cage would be mandatory.

"Oh my God, she just keeps getting sexier!"

"Doesn't she? Dear, white wind please."

After serving the wine I was told to open the living room drapes and sheers, then stand in front of the picture window for all to see.

"No Jill. Facing us. Back to the street."

Until that night I didn't suspect they were more than just friends. I slept in Jill's room.

Erin left at six the next morning.

************

When I got home from work Margaret was sitting at the kitchen table.

"Sit down dear."

Oh oh.

"We went to the gay bar on Maple last night. Know where I mean?"

"Uh. Yes I've heard of it."

"MM. We got talking to a bunch of the regulars."

"Oh, ya?"

"Yes. I told them about my pretty cross dressing husband."

Where was this going?

"Yes. I showed them the picture of you wearing that red fur bikini and heels on my birthday."

Oh no!

"Funny thing. A few of them recognized you, even with makeup on. This little faggot named Timmy, or Tommy, something like that, said you were quite the talented cocksucker."

"Look, I can explain. That was way back in college, way before."

"Shut up! When I asked if you ever sucked a cock, you lied to me. Three weeks. Your mushroom clitty cage is on the vanity. Bring me the key."

That was a long three weeks.

************

"Dear, leave your cage on, but wear your pink satin nightie."

She'd unlocked Jill's room.

Marnie looked so sexy in her purple chiffon baby doll nightie. She handed me her strapon. Shit. "Make love to me Jill, darling."

"A little oral for a start, dear."

With pleasure! I kiss from her pedicured toes, up he calves, up her thighs to her shaved mound.

Lick and kiss. Kiss and lick. Kiss and finger. Finger kiss and lick. So good.

"Mm, Jill. Good girl. Don't stop." Her sweet juices were flowing. She came with that giggle.

"Sit on the chair, dear."

I went to the arm-less white leather chair. She straddled facing me and lowered her self onto the big dildo. She bounced up and down on 'my' realistic nine inch pink cock.

"Mm. Mm. Mm."

She was enjoying the cock ride. I was less thrilled. My cock was terribly tight in my clitty cage.

Wild giggle. Then she held me tight, her head on my left shoulder, my cock still in her pussy.

"Mm. That was good! My sweet Jill deserves a good fucking."

Oh boy! She's going to unlock me and we'll fuck.

"Take off my strapon, dear."

Will Jill get a good fucking?

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cdCindy1cdCindy118 days ago

Great start. I would love to have my wife's friends watch me suck cock and get fucked while dressed in my sexy clothes.

Can't wait for the next chapters.

AnonymousAnonymousabout 1 month ago

Too bad he has no balls and gets away from the whore

AnonymousAnonymousabout 1 month ago

Oh wow is she going to be completely humiliated and used by lots of men, is the wife going to watch or maybe her lady friends will be there too laughing at sissy as she sucks lots of cocks and gets fucked, god I wish I was that sissy, please write another chapter soon xxx sissy Lucy

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