Sissy's Feminized Wiener Pt. 01

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Now his tight skirts lay flat.
1.1k words
4.37
36.4k
11

Part 1 of the 2 part series

Updated 11/13/2023
Created 11/11/2023
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Dear Reader - My stories are about weak pantywaists and the strong women who care for them. The ladies are in control of lovemaking and everyone wears sensuous feminine clothing. You may find this tale amusing if you like sissies and doms enjoying sex in pretty dresses and lingerie.

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Mistress Noreen is a statuesque woman with curly auburn hair that cascades beautifully down her back. She has exquisite taste in clothing. Mini skirts and see-through blouses wonderfully showcase her long legs and perky boobs.

The lady's makeup is always perfectly applied and appropriate for the time of day and the occasion. In short, she is an object of feminine adoration to a sissy like me!

I'd been Mistress' live-in maid providing domestic and boudoir services for about a year. I enjoyed doing household chores clothed in my sexy French maid uniform with its lovely chiffon petticoats. My favorite service though was giving cunnilingus.

Mistress' pussy is the most erotically charged sight I've ever beheld. The labia are perfectly smooth and well shaped, and her pubic hairs are neatly trimmed. When she is horny, her engorged clitoris pushes past its hood and stands erect like a proud pink phallus.

Mistress often orders me to bend over and touch my toes when I'm in my maid uniform. She likes looking up my skirt at the pretty petticoats, sexy garters and lacy panties underneath. Her attraction sends girlish shivers down my spine and makes my dickie stiffen in its buttery smooth nylon knickers.

One day I was bent over and Mistress was fondling my derriere when she announced, "Sissy Darla, you are going to have gender affirming surgery tomorrow."

This was a complete surprise and very short notice, but the wonderful news made me supremely happy. Mistress had already gifted me size DD breast implants, so I wondered what would come next.

She took me to the hospital early the next morning and we met with the surgeon, Doctor Lara Baikal. The tall brunette explained that she would reshape my penis into a little nub, more like a clitoris. Then she would suture my testicle sacs inside my pelvis.

I was delighted that my bulge would soon be gone and thrilled that my tight skirts would now lay flat as if I were a real lady. Femininity means everything to me!

When I returned home from the hospital later that week I was wearing a tight pencil skirt. Mistress welcomed me with a fond embrace and a kiss. Then she looked me over and said, "Your sissy physique is perfect now, Darla and I have a surprise. You won't be sleeping in the maid's room anymore."

Mistress then took me to my new boudoir. There was a large walk-in closet filled with pretty dresses, skirts, blouses and racks of shoes.

The bureau was overflowing with brand new bras, panties, nylon stockings, garter belts and all sorts of sexy undergarments. Pretty purses, hair ribbons, shawls and other girly accessories were piled on a table.

There was a lighted makeup table with every kind of cosmetic, and the bathroom was stocked with hair care products and other feminine necessities. The suite of rooms was every girl's dream!

I thanked Mistress in the best way I knew how. She sat on the bed, pulled down her tanga panties and spread her legs. I applied my tongue and licked her to three prolonged orgasms.

Then Mistress said, "I'd like to see the result of your surgery, Darla."

Now it was my turn to remove my panties. Mistress looked carefully at my new ladylike crotch. She was as happy as I was with the medical procedure.

"Doctor Baikal did a great job!" said Mistress. "She even gave you a little clitoral hood. It's so cute!"

Then Mistress bet me that her clit was bigger than mine. I licked her again to make her clitty erect and then she measured both of us with a ruler. Mistress won the bet which delighted both of us.

"Now, let's give you a real sissy orgasm, Darla," she said with a warm smile.

Mistress sat beside me on the bed and lubed my little nub of a weenie. Then she gently massaged it as I watched. Mistress' lovely manicured fingers with their red polished nails stroked and swirled around my new clitty.

The little nub became engorged and pushed past its clitoral hood. Wonderful girly sensations filled me with sissy delight!

Soon I was breathing hard and moaning. Mistress increased the tempo and pressure on my clitty. Erotic feminine feelings overwhelmed me and I began to climax.

When I screamed "I'm cumming, Mistress!" she removed her hand from my crotch.

My jizz flew across the room and splattered on the wall. The big gooey wad slowly ran down the wallpaper and pooled on the floor. Madame and I laughed uproariously, and she gave me a passionate kiss on my pink lips.

Later, Mistress ordered delivery from a Thai restaurant for our dinner. We enjoyed the spicy meal and drank champagne to celebrate my feminization.

After dinner, Mistress had me model the marvelous new wardrobe she had bought me. I was in sissy heaven trying on the silky panties and bras, sexy dresses, and stylish high heels, platforms and strappy sandals.

Best of all were the tight skirts which lay perfectly flat across my crotch. Madame complimented me on my feminine appearance which sent wonderful sissy tremors from my head to my toes.

We were both turned on by all the sexy clothing. So, Mistress and I undressed and got between the satin sheets of my new canopy bed. She lubed my clitty and I lubed hers.

Next we intertwined our legs like scissoring lesbian lovers. Our passion grew as we rubbed our moist clitties together. Mistress was the first to climax with a loud scream and I came next squealing like a girl.

The next morning I was back in my sissy maid uniform. I served Mistress her breakfast in bed. Then I waited patiently at her bedside as I always do.

When she had finished eating I turned and faced away from the bed. Then I bent over and grabbed my ankles. Mistress likes to start each day with an upskirt and fondling.

She chuckled as she ran a warm soft hand between my nylon covered thighs and up a garter strap to the crotch of my nylon knickers. Finally, she put her fingers inside a leg opening of those bikini undies.

Mistress fondled my clitty and began to laugh which also made me giggle. She finished with a playful smack on my derriere and told me to turn around to face her.

Then she said, "Darla honey, I'm going to invite my friends Karen, Marcy and Lilith over to see your new clitoris this afternoon. I want you to wear your the full circle suspender skirt. That will give them easy access without you having to undress completely. Also, wear the ivory peek-a-boo blouse over the lacy black push-up bra. I love how it shows off your big tits!"

This story will be continued.

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9 Comments
AnonymousAnonymous3 months ago

I always thought it would be hot, (but also extremely nasty and permanent) to surgically emasculate a sissy boi. No breeding and spreading those genes for him/her! I could imagine a slightly different scenario though, maybe the sissy’s “man” package removed as a complete unit, and given to her keeper in a jar of formaldehyde and dated, to be used as a desk ornament, conversation piece, or perhaps just a paperweight. Such to me would be the ultimate irony, the sissy maid dusting and cleaning her owner’s office every day while looking at what was once hers.

Not one hundred percent my thing, but I enjoyed the read, Jackie.

Whippet_DarlingWhippet_Darling5 months agoAuthor

Glad you like the name, woodseaves, and thanks for reading.

woodseaveswoodseaves5 months ago

Darla, that's a perfect name for you, and a lovely relationship you have with your Mistress

Whippet_DarlingWhippet_Darling5 months agoAuthor

Thank you so much, HoneyOrg!

AnonymousAnonymous5 months ago

Omg that was lovely

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