Sissy Applies for a Job

All characters in this story are of legal age.

I had always dreamed of being a saleslady in an exclusive lingerie boutique. So, I applied for a position at the DreamTime shop in Carmel. DreamTime caters to high class women who love seductive intimate apparel.

The store manager, Kristin, phoned to arrange an interview and I began to tingle with sissy excitement. As we were scheduling a date and time for the meeting sweet girly feelings overwhelmed me and I creamed my nylon hipsters.

"Miss Kristin, would you mind repeating that date and time?" I asked with embarrassment after I recovered.

"Sure" she said "Did something just happen there Stacy, dear? I thought I heard you squeal."

"Oh, it's nothing, ma'am. I just spilled some cream" I replied, not exactly lying.

On the day before my job interview I went shopping for a new ensemble to fit the occasion. My favorite store is Satin and Lace where I know the owner, Diana. She supported me like a big sister when I began openly wearing ladies clothing. Diana and I have become friends and she warmly embraced me when I entered the store. Then I told her why I was there.

"A job interview at DreamTime? How exciting, Stacy!" said Diana.

"I'll dress you, dear" she said "Something conservative and yet sensual will impress them. There's a skirt and blouse I'd love to try on you."

Diana retrieved the two items and then asked her assistant, Leslie, to watch the store.

"I'm taking Stacy to the private fitting room" she explained.

Diana led me by the hand as our stiletto heels clacked across the tile floor. The private room was nicely furnished with upholstered chairs and a love seat.

"I'd like to offer you a discount today, Stacy" she said coyly "Are you interested?"

"Oh yes, Miss Diana, please!" I replied enthusiastically.

Diana removed her A-line dress revealing a darling lace-embellished demicup bra. She was also wearing a pink satin thong over crotchless pantyhose. I knelt before my lovely friend and slid the tiny panties down her long legs. Then she sat on the love seat with her knees wide apart and an expectant smile on her face.

I love tonguing Diana and I'd do it even without earning a discount at her store. Flawless labia perfectly frame her exquisite clitty. She is neatly shaven but for coiffed hairs above her snatch and those are styled in a cute little heart shape. Her cootchie is a masterpiece of erotic art.

I tongued and nibbled Diana's pussy lips gently and slowly until she started moaning. Then I increased the tempo and intensity as I began licking her pink pearl of love. Diana responded wonderfully to my oral ministrations and climaxed several times. That entitled me to a ten percent discount.

After I cleaned Diana's pussy juice from my face she showed me the outfit she had chosen for me to wear. The navy blue satin skirt was form fitting and the hem was a little above my knees.

"You'll need a bit of shaping" she said "I have a firm control padded panty that I want you to wear. The hip and fanny enhancements should work wonders. It will flatten that little weenie bulge as well."

The foundation garment under the tight skirt gave me a fine womanly figure from the waist down. We admired my form in the full length mirror and then Diana showed me the top.

"This semi-sheer blouse will show off your lovely breasts, Stacy. It would be too risque for most job interviews, but it'll be perfect for yours at DreamTime."

I was wearing a Playtex 18 hour bra that day but Diana suggested that I try something more provocative. She had a Natori lace-trimmed balconette bra in my size. The black brassiere showing through my thin ivory top was positively alluring. The balconette styling nicely exposed my boobs, too. The suntanned titties pressing against delicate blouse material were practically begging to be fondled.

I was thrilled with my sexy new look and decided to wear the sensuous outfit home. In the bedroom I removed my skirt and jilled off in my panties while caressing my bosom.

I made a salon appointment for the morning of the scheduled interview. My hair stylist, Babs, touched up my roots with Clairol strawberry blonde. Then she trimmed my shoulder length tresses and styled them into a very feminine curly shag. Cynthia, the makeup artist, spent half an hour giving my face a 'no makeup' look. Then she applied light coral lipstick and powdered my cheeks to a subtle blush. The manicurist, Margo, added extensions with delicate french tips to my nails.

I was admiring myself in front of a full length mirror when Margo called Babs and Cynthia over.

"Isn't he precious, girls!" she exclaimed.

"I could eat him up!" said Babs enthusiastically.

The girls wished me good luck with my meeting and embraced me. Cynthia pinched my bum as I departed.

When I arrived at DreamTime for the interview with Kristin my sissy nerves were on edge. The boss lady showed me into her office, noticed that I was trembling and offered me a Valium. I had already taken one at home but I gratefully accepted another. Then an assistant brought us tea and petit fours. Kristin and I chatted amiably for a while as my nerves settled down. Then she segued to the reason for our meeting.

"I happen to know your friend Diana" she said. "We met for coffee this morning and she gave you an excellent employment reference. Diana says that you understand intimate apparel better than most ladies do, that you love serving women and that you have the right temperament to be a lingerie saleslady."

"We confided in each other, too, and Diana told me how you earn discounts on her clothing. She says that you're the best pussy licking sissy she's ever had. So, I think you qualify for the job here at DreamTime."

I was shocked that Diana had divulged such personal information but ecstatic that I qualified for the saleslady job!

"Oh thank you, Miss Kristin!" I gushed "When do I start?"

"Not so fast, Stacy. I said you are qualified. However, I interviewed another qualified candidate just before you arrived. She gave me the best cunnilingus I've had in years. I almost hired her on the spot. The only reason I didn't is that you have something to offer that she doesn't, if you know what I mean."

I knew exactly what Kristin meant, of course. However the prospect of putting my little dipstick inside a living and breathing woman terrified me. I had plenty of experience with silicone vaginas but I doubted that I could cut the mustard when faced with the real thing.

"What do you say, Stacy?" she probed.

I decided that I'd better tell the truth. So, I confessed that I was a virgin and that I was afraid of intercourse.

Kristin was disappointed by my answer and said I would have to present her with a stiff cock to get the job. On the way home I became upset and shed sissy tears into my embroidered hanky.

I was moping in my apartment late that evening when my phone chimed. It was Diana asking whether she could come over and see me. I was eager for her company so I said yes and started getting ready for her visit.

Since it was already late I put on my Flora Nikrooz peignoir set. The taffy pink nylon ensemble is a short flirty nightie with lace on the bodice and a floor length robe with feather trim. I know that Diana likes to see me in evening makeup. So, I gave myself cats eyes and used more liner and mascara than usual. Then I applied Chanel Luminous Red Lipstick and a coat of gloss. I had just finished brushing my hair when the doorbell rang and I went to answer it.

"These are for you, dear" said Diana handing me a pretty little bouquet of poseys.

"They're lovely, Miss Diana!" I gushed "Won't you please come in and make yourself comfortable while I put them in a vase?" I said.

When I returned to the living room Diana was seated on the sofa. She was wearing a black flutter-sleeve cocktail dress with a plunging neckline and a slitted skirt. Her makeup was almost a mirror image of mine and her red lips were a perfect Cupid's bow. She was smiling warmly.

"Sit beside me, precious" she said in a tender voice "I have something to discuss with you."

"Kristin phoned me after your interview. She shared with me that you're a virgin and that you're too nervous to go all the way with her."

"That's true" I admitted "I would probably faint."

"Well, sweetheart, would you like to try with me? I'm your friend and I want to help you."

My happy heart nearly leapt out of my chest!

"Yes please, Miss Diana!" I exclaimed.

"Alright, honey" she said "Let's go to your bedroom."

Diana glanced around my room admiring the makeup table and canopy bed. Then she asked me to unzip her dress. She was wearing a Chantilly lace bralette and crotchless pantyhose.

When she sat on the bed I went on my knees to lick her pussy.

"No, Stacy" she said "Tonight is my treat."

Then she removed my peignoir robe, laid me on the bed and lifted the hem of my nightie. I was only a little bit nervous and, thankfully, my weenie was hard. Diana knelt above my thighs with her long legs straddling my sides. Then she positioned her bottom on the tip of my dick and gently coaxed it inside her warm moist pussy. Diana fucked me for a long while and climaxed multiple times. After she finished using my weenie, she cuddled me in a soft embrace until I fell asleep.

I felt wonderful when I awoke the next morning. I can't say that I had become a man but at least I was an experienced sissy. Then Kristin phoned while I was still in my peignoir and asked to continue our interview. We would meet for lunch at the Hilton.

I chose a dainty powder blue sundress for the daytime occasion. The darling little frock had yellow daisies embroidered on the bodice and above the lacy hemline of the skirt. I tied a matching ribbon in my hair.

Kristin arrived in a fashionable business suit consisting of a rose silk top and a charcoal grey jacket and matching knee-length skirt. Her hair was in a stylish updo and her makeup was perfect. We were both wearing stilettos although her heels were higher than mine.

At the restaurant Kristin ordered a porterhouse steak while I asked for a garden salad with dressing on the side. She enjoyed a half bottle of Merlot with her meal but my nervous stomach could only tolerate seltzer water. We chatted pleasantly about fashion as we ate. After finishing her dessert Kristin fetched a room key from her purse and instructed me to follow her. I now understood the reason we had come to a hotel for lunch.

My success with Diana the previous evening gave me a bit of confidence. I was still relieved though when Kristin offered me a Valium after we entered the room. She unzipped my sundress, removed it over my head and complimented me on my ivory Cosabella bra and panty set. The nylon confections were lavished with Duchesse lace and tiny ribbon bows. Kristin wore an exquisite Chantelle Rive Gauche bra with coordinating french cut panties. Her flamingo pink intimates made my little dickie stir.

"Diana told me about your rendezvous last night" said Kristin "Are you ready to try your luck with me now?"

"Yes, Miss Kristin. I would be honored to try pleasing you" I answered nervously.

"Alright, Stacy, but I'm not offering you a gift like Diana did. You've got to earn a fucking from me."

Kristin removed her pretty panties and sat on the edge of the bed. Then she spread her legs widely and motioned for me to kneel before her. I took my place and began licking. The passionate lady was quick to respond to my ministrations. Unlike Diana who climaxed multiple times, though, Kristin enjoyed one long continuous orgasm.

Kristin pulled me up from my kneeling position when she finished and spooned with me on the bed.

"That was a very fine licking, Stacy" she said in a satisfied voice.

"Thank you, Miss Kristin" I replied hoping she would offer me the job at DreamTime.

"However, the young lady I interviewed did slightly better. So, it all depends on whether your weenie meets my standards."

"I hope it will, Miss Kristin" I responded feebly.

"Okay, Stacy" she said "but I do things a little differently than your friend Diana. I'm going to give you a good spanking first."

The smacks were more humiliating than painful and I was amazed to find that they calmed my nerves. When Kristin laid me on the bed I had a raging boner and a strong desire to be fucked by this assertive female.

Kristin straddled me and quickly engulfed my stiffy with her steaming hot pussy. Unlike the one continuous orgasm of our cunt licking session she had many intense climaxes. When I finally jetted a massive load of cum into her hungry snatch Kristin collapsed next to me and held me in a tight embrace.

"Stacy, my darling" she whispered "you'll start work tomorrow."

My sissy dreams had come true!