Sissy Becomes Bra Fitter Pt. 03

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 Parts 1 and 2, I passed as female and landed a job as a bra fitter. Customers welcomed my intimate approach to serving them. Warm feminine feelings flowed between us when I removed their brassieres and gently touched their soft breasts. I massaged their wonderful mammaries, they kissed my pink lips and orgasms followed.

My supervisor, Ms. Carla Ellis, approached me and said "I've noticed the smiles on your customers' faces and I'd like a bra fitting for myself."

She was wearing a pretty button-back blouse with puff sleeves. In the fitting room I helped remove the blouse and then unclasped her Patrizia white lace bra. Her breasts were gorgeous tanned orbs with pink areolas and her nipples stood erect. When I measured her, I was careful not to touch her boobs directly with my hands.

Then she said, "Aren't you going to massage them?"

I was shocked and speechless.

Then she continued, "I've seen you do it on our security cameras."

"I'm so sorry, Ms. Ellis," I managed to sputter.

"Don't be, Karen," she replied in earnest. "I asked you for a fitting because you know how to treat a lady."

When she said 'how to treat a lady' I sensed danger.

"That's right, Karen," she continued. "I knew that you were masquerading as a female when I noticed a bulge under your skirt. Don't be frightened though, sweetie. I'm not going to expose you. After all, you're a very good fitter and you've sold lots of bras."

I was so relieved that tears of joy came to my eyes. Ms. Ellis gently dried them with a perfumed hanky from her purse. "Oh, you poor sissy boy. Don't cry," she said. Then she placed my hands on her soft warm bosom and added, "These will make you feel better."

I felt better at once just as Ms. Ellis said. Then tender girly sensations arose and my weenie stiffened. Now I felt magnificent!

When I began massaging Ms. Ellis' lovely tits she put her lips on mine and kissed my glossy pinks with her deep corals. Then her hand went under my skirt and up a garter strap to the crotch of my Let's Make Love nylon panties.

She pulled down my knickers and fondled my wiener. I love aggressive women who take charge. I felt marvelously submissive as glorious sissy feelings grew strong.

Then Ms. Ellis sat me on a stool, raised her skirt and straddled me. She guided my dickie into her wonderful moist pussy and gave me the most splendid fucking imaginable. I desperately wanted to climax but I waited for her. When she screamed in ecstasy I shot a full load of sissy cream into her hungry vagina.

The mutual orgasm created a tender bond between us. We gazed into one another's eyes, kissed each other's lips and embraced until Ms. Ellis had to go. Before she departed we exchanged phone numbers.

After lunch Ms. Ellis was standing outside my fitting room beside a tall brunette with a statuesque build. The two ladies entered and Ms. Ellis said, "Karen, I want you to meet my boss, Ms. Susan Carter."

"Susan," said Ms. Ellis, "this is Karen. He's the sissy bra fitter I told you about. Karen loves giving women's breasts his personal hands-on attention. He's also a superb lay and he takes a very considerate 'ladies first' approach to orgasms.

"Karen," said Ms. Carter without further introduction, "I've been told that sissies wear sexy lingerie and I'm very curious. May I see yours?"

"Oh yes, Ms. Carter, with pleasure!" I exclaimed. Then I lifted my skirt and showed her my pretty garter belt and panty set. I turned around and wiggled so she would notice how nicely the undies fit my derriere. Then I turned back, smiled and curtsied.

Ms. Carter seemed to enjoy the show. Then she looked more closely at my panties and ran her hand over the soft tummy panel. She seemed puzzled and asked, "Why isn't your weenie stiff, Karen? Don't you think I'm attractive?"

"I think you're beautiful, Ms. Carter!" I exclaimed, "and I'm sure that my dickie will respond when I take your measurements."

With that, Ms. Ellis departed and I unbuttoned Ms. Carter's pink chiffon blouse. She was wearing a Glamorise MagicLift Front Closure bra. When I removed it her lovely breasts hung down like big ripe apples.

"Let's skip the measurements, Karen," she said. "I want you to kiss my boobies and then nuzzle them."

I gladly did as she ordered. Before long she was moaning softly and so was I.

Ms. Carter whispered in my ear, "You're a good girl, Karen, now let's check your weenie again."

She slipped her hand under my skirt and squealed for joy when she felt the stiff dickie under my panties.

Then she said "I screw a little differently than most women, Karen dear. I don't just request 'ladies first' priority I insure it. I'm going to squeeze the base of your boner so you don't cum early. I know you won't mind."

Ms. Carter sat me on the same stool that Ms. Ellis used. She removed her panties, straddled me and used my rod like a sex toy for three screaming orgasms.

Then she stood up, smiled at me and said, "It's your turn now Karen. Make sissy juice in your panties for me. I've always wanted to see a femboy jill off."

I wanted to see myself, too. So I turned toward the mirror, reached under my Armani skirt and stroked myself through my nylon panties. I closed my eyes and imagined being Ms. Carter's sissy bride on our wedding night.

Tender submissive feelings grew inside me and I spread my thighs like a surrendering maiden as I neared climax. Finally, I held an embroidered hanky over the tummy panel of my knickers and reveled in a stupendous orgasm.

Ms. Carter exclaimed, "Wow! That was awesome!" Then she went on, "But you've soaked your pretty little panties, haven't you Karen sweetheart? Let's get those wet undies off and I'll give you mine. We girls have to help one another."

She was wearing delicious La Perla tulle panties with floral lace. I was overwhelmed by Ms. Carter's beautiful gift but the best part was knowing that the soft cotton crotch had nestled against her wonderful pussy. When she slipped them up my legs I felt a delightful girlish tingle all over.

Before leaving Ms. Carter stuffed a generous tip in my blouse. Then she said, "I'll be back later in the week, Sweetie Pie," and she winked at me.

I have the best job in the world!

The End.

Your comments are welcome.