Sissy Becomes Bra Fitter Pt. 02

Story Info
Hands-on intimacy and femboy ecstasy.
876 words
4.66
6.8k
4

Part 2 of the 3 part series

Updated 11/18/2023
Created 11/14/2023
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Dear Reader - I created this story to amuse fetishists who love pretty lingerie and sexy ladies. The lead character is not quite so idiotic as my usual pantywaist twits but he's just as easily charmed by attractive women.

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In Part 1, I passed as female and landed a job as a bra fitter. My first customer was thrilled with my personalized hands-on attention to her breasts and bought three brassieres. I was so erotically charged by our sensual encounter that I spurted sissy cream on a Kotex maxi pad.

The next customer was an attractive thirty-something woman wearing a rather loose top. The garment did nothing to exhibit her figure.

In the fitting room the lady confided in me that she had resorted to wearing tight minimizer bras to stop her breasts from bouncing. She hated the minimizer style though because it flattened her bosom while she actually wanted to show it off.

"We have bras for women like you, dear," I said encouragingly.

I helped remove her blouse and bra, and then took her measurements. The obvious reason for her bouncing boobs was that they were size DD.

"Do you mind if I touch your breasts, ma'am?" I asked. "I can best gauge the kind of support you need by feel."

"I don't mind at all, Karen," she replied, reading my name tag.

I moved behind her and gently cupped my hands under her delightful mammaries. When I tenderly massaged them she closed her eyes and softly sighed with pleasure.

"That feels divine!" she said. "Please don't stop."

Her breathing grew louder as I continued my ministrations. Then she turned to face me, drew our bodies together and pressed her full ruby red lips against my glossy pink ones.

"Does the door lock?" she asked.

I latched it, sat on a chair and motioned her to my lap. Then I recommenced my breast massage with one hand while my other went under her skirt. I found stretchy garter straps and followed them upward. Finally I encountered a panty girdle which seemed to be a roadblock to my exploration.

"It's got a convenience opening," she said in a breathless voice. "Please do me!" she begged. Then she spread her silky soft thighs wide apart.

Inside the girdle my fingers encountered her wonderful moist pussy. I gently stroked her labia. Then I softly swirled the tip of my index finger on her clitoris. Finally, I inserted my middle finger into her coochie and began rhythmically stroking. My lady was moaning and her breathing deepened.

"More!" she pleaded, "More fingers, please! And harder!"

So, I put three digits deep inside her hungry vulva and pumped her forcefully. Soon she climaxed wildly and stifled a scream.

After she recovered her breath the sexy lady kissed me again and began massaging my breasts. I was glad to have put realistic silicone pads instead of foam rubber in my bra.

Then she felt under my skirt and ran a warm hand between my nylon sheathed legs. I spread my legs like a bride on her wedding night and erotic female sensations swelled inside me.

Next she advanced to my panties and slipped her fingers inside an elastic leg band. She nearly touched my dickie, and I could not afford to let that happen.

"Please, stop!" I exclaimed. Then I told a white lie, "I'm having my period, ma'am."

I gently withdrew her hand from under my skirt and said, "Let's get the bra you need."

I went back to the sales floor and returned with a Playtex Bounce Control bra. I explained how their patented design steadies the breasts.

"The cups also have a strong inner support and higher sides for added control," I said.

The lady was very pleased at how the bra gave her a Dolly Parton figure. Next she took several steps and found that there was no bouncing. "Hurray!" she shouted, "This is exactly what I've been looking for!" Then she embraced me warmly.

The satisfied woman bought two of the Playtex garments. After paying, she stuffed a generous tip in my blouse.

My supervisor, Ms. Ellis, noticed the contented lady with her purchases and she approached me smiling.

"You're a wonderful bra fitter, Karen!" she said. "Would you mind giving me a fitting?"

"I'd love to, Ms. Ellis!" I replied, "First I've got to visit the ladies room though. I'll be back directly."

My intimate encounter with the bouncing boobs lady had given me a huge boner. I was afraid that Ms. Ellis would notice the bulge in my skirt unless it took care of it.

In the restroom I lifted my Armani skirt and pulled down my Let's Make Love nylon panties. The pink knickers are decorated with delicate Chantilly lace around the leg openings and have dainty ribbon bows on each side of the satiny smooth tummy panel.

On the toilet I only lowered my panties to my knees so that I could see them while jilling off. I was already so erotically charged that just a couple of strokes sent me over the edge. A tidal wave of marvelous girly sensations swept over me and my weenie erupted like a pink volcano.

This story will be continued.

Your comments are welcome.

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6 Comments
AnonymousAnonymous4 months ago

Beautifully written with lots of detail about brassieres.

I wonder if I could get a job at that store as well.

monasissymonasissy4 months ago

I love sissy periods. Love this story. Thank you

Whippet_DarlingWhippet_Darling5 months agoAuthor

Love you humor, Anonymous!

AnonymousAnonymous5 months ago

I hope you sell a few girdles as well as bras.

Whippet_DarlingWhippet_Darling5 months agoAuthor

Thank you for your appreciation, louislion51. The next chapter is on the way to you.

Sincerely,

Whippet_Darling

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