The following story was inspired by Tupperware!, a documentary film that aired on the PBS show American Experience. The film featured dozens of clips appealing to those of us with an appreciation of and attraction to female dress of the fifties. At one point in the documentary, there was a brief discussion of "Tupperware ladies", husbands of authentic (for lack of a better term) Tupperware ladies who would appear in rather clownish drag at the ladies' meetings. One contemporary authentic Tupperware lady revealed that her husband was one of the men who continued this tradition.

What follows is a period piece of sorts. Set in the fifties, it deals with one woman's reaction to "Tupperware ladies"

 

Tupperware Queen

by Gini Lane

 

We had struggled so at the beginning of our marriage. I had attempted something of an acting career, while Bob had concentrated on his painting. Jobs were few and far between. More often than not, I fell back on the occasional modeling stint, while Bob was forced to accept work contracted out by a local advertising firm. We were happy with each other, but miserable about our surroundings. My chance attendance at a party changed everything for us. I was introduced to the world of Tupperware and, seeing a way out of our financial difficulties, threw myself into its orbit.

To say that Tupperware was good to us would be an understatement. In little more than a year we had moved out of our squalid cold water apartment, and had taken out a mortgage on a spacious new house in a new suburb outside Philadelphia. I believe my rapid rise up the ranks was due to two factors: my belief in the product, and the enjoyment I felt in working with other women. It was nice, for once, not to fall under the leering gaze of men, something I had experienced time after time while modeling.

As I say, Tupperware had been so very good for us, and yet there was one thing about the company that I wasn't too pleased with: these were the "Tupperware ladies", husbands who appeared at our local meetings dressed as women.

The "Tupperware ladies" had, without exception, presented unattractive images. They wore their wives' old clothes and ill-fitting shoes, topped off by ratty wigs and, most often, a silly looking hat. The last I had seen was a hairy man who had worn an old gown that was ripping at the seams in order to accommodate his boxy body. He spoke in a high pitched voice, shrieking as he related stories of his successes. While the rest of the ladies seemed to find his performance amusing, I felt offended by the spectacle. I had shuddered at the thought that Bob would be expected to join their ranks at the next meeting. I was determined that my Bob would not follow this example. My husband would present the image of a confident, cheerful, attractive, proper woman; in short, he would reflect the very image of the true Tupperware ladies.

 

These thoughts in mind, the following month I set out to Hathaway's, my very favorite women's clothing shop. I would like to say that I bought all of my own clothes at the Hathaway's, but as good as Tupperware had been to us, I was limited by my pocketbook to shopping at the store only on special occasions. I had a sense that Bob's first experience in ladies' clothing might rank as the most special occasion of all.

I began, as one might expect, in the lingerie department. Bob is a very trim man, not at all like the "Tupperware lady" who had offended me so. I was confident that with a little nip here and a little padding there Bob's form could look convincingly female. My first purchase was an open-bottom girdle. It was rather elaborate in its beauty, featuring a series of contour bands to shape the waist, hips, back and derriere. I must admit I smiled when I read that the "flexible spiral boning" provided back support. Bob would occasionally complain of a bad back.

Must remember to tease him, I thought. I'd tell him to put on his pretty girdle the next time his back bothered him.

The girdle had a fourteen-inch front hook and eye opening; a feature I felt Bob would be able to manage. It was available in black, rose and white. As this was to be Bob's first time, I felt white was appropriate.

The girdle's four detachable garters served to remind me that Bob would require stockings. I found a pair that was absolutely lovely, in beige with a hand sewn back seam and finishing hole at the top of the welt. They were expensive, but I justified the cost by telling myself, once again, that this was to be Bob's first experience in feminine finery.

The bra, I realized, was to be my most important purchase. The last thing I wanted was for my Bob's breasts to look like the large, clownish protrusions of the other "Tupperware ladies". I spent a great deal of time going over racks and racks of brassieres, inspecting cups, straps, gauging shape, comfort and support. What I was hoping for was a bra that, combined with falsies, would be help provide the look I was after, without sacrificing beauty. I finally settled on a white and floral lace Charmante bra by Corette. Low cut, it featured net lined breast cups with boning with powernet sides and back. The front, sides and back also featured boning. There was a three-tier hook and eye closures, so I felt confident that it would fit Bob.

At the risk of repeating myself, it truly was a beautiful bra, the sort of bra which, had I worn it, would have made Bob drool. I hoped he would be pleased.

I next purchased next a beautiful satin camisole that featured intricate embroidery on a soft baby net. I was confident that the combination of my husband's new camisole and bra would be quite breathtaking.

I'd already decided that Bob would wear a petticoat to the meeting, so many of us did. This meeting being so special, I had planned on wearing my favorite petticoat. The petticoat I chose for Bob was similar: two layers of petti, the bottom layer of paper nylon, with a bottom ruffle. The top layer consisted of a crinoline net with five rows of lace trim with an extra ruffle of crini net at the bottom. It was adorned with more than two dozen cute little bows of pale pink ribbon. As I'd looked it over, the paper nylon had made a pleasant rustle that was simply irresistible.

I'd seen the dress I wanted for Bob in Hathaway's window as I'd been running errands the previous week. In fact, it had stopped me in my tracks. There was just something about the dress that told me it was perfect for my husband and I'd been thinking about it ever since. It was a lovely red shirtwaist dress with three quarter length dolman sleeves and full skirt. It had a false inner sleeve at the elbow and an inner collar at the neck, both in white. The optional fabric belt I felt was a must, as it would help to show off Bob's new figure. Added to all this was a white tulle lining, which would only serve to accentuate the effect of the petticoat that had captivated me so.

One would think I would have trouble in buying shoes for my Bob. In fact, this was the easiest part of the whole trip. You see, Bob had very small feet for a man, while mine are slightly large for a woman. In fact, I would occasionally wear his sneakers when gardening.

I settled on a pair of pumps with three-inch heels in a shade of red that matched his new dress.

I was about to leave the store when I realized I'd forgotten to buy Bob's panties. I headed back to the lingerie department. In doing so, I came across a display of bridal finery. My eyes were immediately drawn to a pair of divine ruffled white satin bridal panties. I simply couldn't resist.

I made arrangements for the entire purchase to be delivered the following morning, a time when I knew Bob would be out. I didn't want him to have the slightest inkling of what wonderful things were in store.

 

The next day, I waited at the window, coffee in hand, for Hathaway's delivery van. For some reason, my heart started racing when it finally arrived. I suppose I was simply so excited, recognizing that the arrival of the pretty clothes were the first step in what I hoped would be a wonderful transformation.

It took me several trips to carry all the packages upstairs. I lay Bob's new clothes out on our bed, beginning with his girdle, followed by stockings, his bridal panties, Charmante bra, camisole and, of course, the intoxicating petticoat. Finally, I laid out the dress, spreading the skirt to its full width. I'd only just finished when I heard Bob walk in the front door. I skipped down the stairs and threw my arms around my husband.

"A man from the store delivered your new clothes while you were out, darling." I said, giving him a kiss.

Bob immediately became flustered. Perhaps it was the thought of a delivery man carrying in boxes of feminine clothing meant, not for a woman, but for another man; perhaps it was the realization that he could no longer deny that his debut as a lady was close at hand.

We ate a light lunch. I was so excited. I must have seemed a non-stop chatterbox. Bob was quite silent. My poor husband became even more silent when he learned that the meeting was to be in late afternoon, not in the evening as he'd thought. When he did speak he revealed that he'd been expecting to travel to the meeting in darkness, not under the glaring light of a late summer afternoon.

We left our plates and headed upstairs. I asked Bob to shower and shave his face. The previous day we'd enjoyed a rather amorous evening, which had begun when I'd joined Bob in the bathtub, helping him to shave his legs and arms.

As I waited for my husband, I prepared my vanity table and checked my makeup. After some reflection, I decided to change into a fresh blouse. I was already dressed for the occasion in my favorite matching bra, panties and garter belt. Of course, I was wearing my favorite petticoat, covered by a very full, calf length skirt with crinoline net for extra fullness. I was particularly fond of the flat waistband, which had to be undone as I substituted the cotton blouse I had been wearing for a slightly dressier one of satin.

It wasn't long before I had Bob sitting at the vanity in his silk bathrobe.

The last article of masculine clothing you'll be wearing today, I thought mischievously.

It wasn't at all difficult to make up my Bobby's face. Previously I had considered his fine features to be boyish. Now I thought of them as girlish. He didn't struggle, or raise any sort of fuss, even when I took the liberty of plucking a few hairs from his eyebrows. Nor did he complain when I painted and buffed his fingernails. I was so pleased with my husband. I applied a ruby lipstick, kissed him, and then reapplied it.

I finished my work by placing a shoulder length blonde wig on his head. I had worn the wig on a few modeling assignments, whenever the photo shoot had called for a blonde, rather than a brunette. The wig seemed a natural fit, perhaps in part due to the fact that the color was almost identical to Bob's own hair.

"You make a lovely looking woman, my love," I said, and kissed his forehead. "I'll leave you now, darling. Your clothes are all laid out on our bed."

Though I so wanted to see Bobby's reaction to his pretty new clothes, I had decided to leave him as he entered our bedroom. I wanted him to be alone with his thoughts as he dressed in feminine finery for the very first time.

I made my way downstairs, cleared our lunch dishes, and made a pot of tea. All the while I listened carefully for any sounds coming from above. I was disappointed when I heard nothing, not even the delicious sound of the petti's paper nylon.

After what seemed like a very long wait, but was really less than half an hour, Bobby appeared at the kitchen door.

My husband was a vision of loveliness, from his shoulder length blonde locks to his shiny red pumps. He stood still, seemingly paralyzed, his hands clasped in front of the skirt of his dress. I smiled and, taking his hands, lead him to the table.

"Please, darling, sit. I've made us some tea."

I wanted his entry into womanhood to be as gentle as possible. I placed my hand upon his, giving it a loving squeeze. We sipped our tea. I spoke of fragrances, fashion, gardening and cooking, in short, everything that two girlfriends would be expected to discuss over tea. Bobby said very little and I could see him squirm every once in a while.

"A new girdle does take some getting used to," I said reassuringly. "And, of course, you are wearing your very first bra."

Bobby blushed.

 

After tea I suggested to Bobby that he might like to relax in the living room. We still had an hour or so before we would have to leave. Again, I looked after the cups and saucers, pretending that Bobby was a girlfriend who had come to visit. It was a fun type of thought.

I dried my hands, grabbed my purse from the kitchen counter and went to join Bobby in the living room. But the room was empty. For a moment, a very brief one mind you, I had the horrible thought that he had decided he simply couldn't go ahead with it all. I had the awful image that he might be upstairs taking off his dress.

I needn't have worried. I caught sight of him standing before the large hallway mirror. Bobby turned this way and that, looking at his rather curvaceous form from all angles, inspecting my handiwork. The paper nylon of his petticoat produced such a pleasant swishing sound. I was so pleased.

"You look lovely, Bobby."

He lowered his eyes, appearing quite sheepish. He looked so vulnerable, so adorable. I sensed something was troubling him.

"What is it, my love?" I inquired. "Is it nerves? You really shouldn't worry your pretty little head."

It took a few minutes to get Bobby to tell me what was troubling him. It seemed that he had an erection. In fact, he'd been in a constant state of arousal since he had laid hands on his open-bottom girdle. Before he'd even started getting dressed! He was concerned that the ladies would be able to tell, that they would be able to see his erection pressing against the skirt of lovely shirtwaist dress. He was so cute in his embarrassment. I couldn't help but smile.

"Oh, Bobby, you are so cute." I tried to dispel his fear. "You know I wouldn't let you appear in public as anything but a proper lady."

Stepping back I studied the front of his skirt. I could see no sign of his problem.

I placed a hand on the front of his skirt. At first I felt nothing, but as I applied pressure I could feel his hardness beneath the skirt, tulle, crinoline, paper nylon and frilly panties. He shook, seemingly unable to contain himself.

I felt such power, as if I was firmly in control.

I dropped my purse and, placing my other hand in the small of his back, feeling the structure of his girdle, drew him towards me. We kissed tenderly at first. I forced my tongue between his lips, something he'd never before allowed.

We were soon on the floor, side by side, searching through each other's petticoats. With the layers of crinoline, lace, tulle, ribbons, bows, it took me longer than one might expect to find my Bob's pretty bridal panties. Drawing my fingers lightly over the ruffled satin front, I could tell they were already quite wet - as were mine. I allowed Bob to play with the lace hem of my own panties before, reluctantly, drawing his hand away.

"Bobby, we must be careful. We mustn't mess ourselves up before the meeting."

I knew to be cautious, lest he have an accident and spoil his pretty new outfit. I reached across the floor to where my purse had fallen and drew out a clean handkerchief. He shivered as I placed it around his cock, moving it up and down his shaft, ever so slowly, ever so gently.

He whispered how good it felt.

"Does it feel as good as you look, Bobby?" I teased.

He nodded yes.

"You really look beautiful, Bobby. So desirable. The other ladies will be so jealous."

Bobby moaned. He was so passive. As I continued to gently stroke, I ran my free hand over Bobby's beautiful dress, thrilling to the feel of the confining underwear beneath.

"Oh, Bobby, you really do look pretty. Do you feel pretty, Bobby? Aren't your new clothes wonderful? Don't they feel good, Bobby?"

I unbuttoned his shirtwaist part way, just enough to slip my hand beneath. His camisole was slippery, sliding over his floral lace bra and his falsies. The feeling was delicious. Bobby placed his hand over mine and had me squeeze his left breast, moaning with pleasure as I did.

"I love your breasts," I whispered. "You're breasts are so beautiful, Bobby."

At that moment, Bobby climaxed, shooting wave after wave of cum and I could feel my silk hanky grow warm and wet. In fact, it as completely soaked. When he'd finished I reached for a second handkerchief, which I used to slowly, carefully, wipe up the semen.

Though I knew no one would see, the last thing I wanted was for Bob to attend the Tupperware meeting in a cum-stained petticoat.

"Lie still, my love," I whispered.

  

  

  

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