Saturday Night Lives

Third Saturday of the month, we dine with our friends, Bill and Rosemary Lucas. We take turns, one month at their house and one month at our house.

Last month at our house, Rosemary and my wife Karen discussed how men can be self-involved. As an example, Rosemary went on and on about how Bill spent a lot of time and money on photography.

Not to be outdone, Karen mentioned how I spent a lot of time and money on crossdressing.

I turned beet red with embarrassment. My crossdressing was a family secret. I was incredulous that Karen would let the cat out of the bag, but in the heat of the moment, she wanted to up Rosemary’s complaints about Bill.

“Who would have thought that about Stanley,” commented Rosemary.

“I’m shocked,” said Bill.

“Yes, ‘Stan the Man’ likes to become ‘Pearl the Girl’ about once a week,” added Karen.

“I'd like to meet her,” Bill said with a Cheshire Cat grin.

With a twinkle in her eye, Rosemary suggested, “Maybe Pearl can dine with us next month.”

“I think that can be arranged,” Karen replied.

“I can't wait!” Rosemary exclaimed. I did not say a word and the subject was dropped for other topics that I cannot recall because my head was spinning about what just happened.

On the way home, Karen apologized for telling Bill and Rosemary about Pearl.

“I accept your apology, but why did you go along with Rosie’s idea about Pearl showing up for dinner next month?”

“At first, I thought it would be too embarrassing for you, but Rosie and Bill were so enthusiastic that I thought, why not. Pearl is a beautiful woman and she deserves to go out and be seen.”

“I'll think about it,” was where I left it.

The month passed and I thought it was a dead issue.

Over breakfast on the morning of our next dinner with the Bill and Rosemary, Karen asked, “What is Pearl wearing tonight?”

I didn't see that coming.

“Stan was planning to go to dinner without Pearl tonight,” I replied.

“Rosie and Bill were expecting to see Pearl. In fact, I was expecting to see Pearl, too.”

“But...”

“You are going to disappoint everyone. Why don”t you stop being so self-centered and think about others for a change.”

Karen was angry... very angry. I felt guilty and started reconsidering. Maybe it wouldn’t be so bad. Bill and Rosie already know and it might be fun to get out of the house en femme, as the “girls” say.

I finally relented, “I guess Pearl can make an appearance tonight.”

Karen's anger turned to elation, “Great! I'm so happy that she changed her mind.”

I completed my Saturday chores by mid-afternoon and began transforming myself into Pearl.

I disrobed and applied hair removal cream on my legs, arms, breasts and as far as I could reach on my back. While waiting for the cream to do its job, I applied a shaving gel to my face, neck and armpits, put a fresh blade in my razor and got in the shower.

As the water washed the depilated hair from my body, I shaved. Then I cleansed my whole body, rinsed and stepped out of the shower.

After drying myself, I rubbed moisturizer into my soft skin, then I slipped on a pair of black lace panties (the only kind I will wear) and sat at the vanity to do my makeup.

I used some concealer to hide the faint shadow of my beard, then applied foundation and powder. I did my eyes next. The eyeliner makes them stand out and a deft application of mascara and eyeshadow make them look smoky and mysterious. Some blush and muted lipstick followed.

Pearl is a blond and has a variety of hair styles at her disposal, so I had to decide which coiffure she would wear. I selected a short wispy layered cut with flipped ends and dark roots that add authenticity to the wig. I slipped the wig onto my head, straightened it and finger-styled it.

I removed my undies from the bureau and pulled on a high waist panty girdle, while tucking Willy and his friends out of sight. Next came the matching long line bra and silicone breast forms that went into its cups.

Sitting on the bed, I put my pink-polished toes into a pair of suntan control-top sandalfoot pantyhose and worked the sheer nylon up my legs and over my girdle.

I slipped a black sheath dress over my head being careful not to smudge my makeup on the fabric.

Then I asked my spouse, “Karen, would you please zip up my dress?”

“Yes, honey,” she answered. She stopped combing her hair to assist with my zipper.

“There you go,” she said when she finished zipping me up and closing the clasp just above the zipper.

“Thank-you, sweetheart.”

I completed my look with some tasteful jewelry: a silver watch on my slender wrist, silver heart clip-on earrings and my wedding band and engagement ring. Finally, I added a set of stick-on nails to my fingers.

I straightened out my dress and smoothed the hem, which fell about three inches above my knees, then slipped on a pair of four-inch black patent pumps. A spritz of perfume on my wrists and on the nape of my neck and I stand back to admire the finished product in our full-length mirror. Stan has left the building and Pearl was in his place!

I announced, “I'm ready,” using a feminized version of my voice.

“You certainly are, Miss Pearl! I'm almost ready, too. Can you return the favor?”

Karen had just slipped on her green belted sweater dress and was waiting for me to zip her up.

“Sure thing,” I said and I zipped up her dress.

“Check me out, honey, to make sure I look okay,” she asked.

She spun around with her arms posed akimbo so that I could see any flaws in her ensemble.

“You look perfect,” I said, “I am so lucky to be married to a drop dead gorgeous woman.” 

Then I spun around with my arms posed akimbo so that she could see any flaws in my ensemble.

“Perfect... I am lucky to be married to a drop dead gorgeous woman, too,” she replied.

We air-kissed each other so as not to smudge our makeup, grabbed our purses and walked to the garage.

Karen drove because I had never driven wearing high heels. It was only a half-mile ride to the Lucas home and when we arrived, Karen parked the car on the street and we walked hand-in-hand to the front door.

Karen rang the bell and we soon heard the clicking of high heels approach the door from the inside. The door was opened by a beautiful woman, who I didn't recognize.

Karen said, “Hi, Bill. You look lovely.”

“Thank-you, but Bill’s not here. Please call me ‘Pamela.’ May I assume your beautiful girlfriend is Pearl?”

“You assumed correctly, Pamela.”

I was speechless. Pamela nee Bill looked fantastic. He was wearing a white jacquard mini-dress, off white metallic pantyhose and silver strappy 4-inch sandals. His shoulder-length chestnut hair was up and his makeup was perfect.

“You look fabulous,” I gushed.

“You, too, girlfriend. Let’s take some photos!”

Wearing Charo Ruiz

Arthur Askey femulating in the 1940 British film Charley's Big-Hearted Aunt.