Last week my son Edward and his wife Claire came over for dinner and to spend time together on Saturday evening. Ed and Claire have been married a little over 1 year and recently moved back to our hometown after changing jobs. Ed had been away for about 7 years, during which he attended and graduated from a prestigious university and then landed his first job in the banking industry. He met Claire through a friend at work and over a period of a year they became good friends and then inseparable. Claire was a good match for Ed, they made a perfect couple and seem to be attuned to one another; she is kind, well mannered, intelligent - not to mention beautiful with a near perfect body and a face that makes women and men do a double take.

I really just knew Claire superficially and from the occasional get togethers during their courtship and wedding festivities but got the distinct impression she was quite refined and liked things 'just so' and would not settle for anything else. She was apparently a very girly girl and indulges herself in feminine dress and style down to the last detail.

We had just finished dinner and dessert and we were cleaning up the table when Ed handed me a stack of plates and I got a good look at his hands. His nails, while plain looking, had obviously been cared for and his cuticles looked artificially neat. The three of us moved to the kitchen and loaded the dishwasher and put leftovers away. Under the stark light from the LED lighting I got a closeup look at Ed's face from the side. It was clear to me Claire must have been assisting with his personal grooming as it appeared he was wearing a little concealer and perhaps a trace of powder. While making a mental note to have a future girl chat with Claire and see what I could learn, the irony of the situation was not lost on me. In my mind, there was no doubt that Ed had fallen into a silken trap sprung by Claire. "Interesting, but no surprise there" I thought as Ed's upbringing and childhood experiences had conditioned him to offer no resistance to her web.

You see, during Ed's childhood years I let him experience things and make up his own mind as to what was right for him, what he wanted to achieve, and let him explore accordingly. As early as elementary school Ed had his first dress-up experiences, once for a Cub Scout play, where girl's parts had to be played by boys, and then once or twice at Halloween for trick or treating. Being his mother it was my responsibility to listen to his thoughts but help choose his costume and accessories. We kept things very simple with a borrowed dress and pair of shoes, a play wig, and a touch of rogue and lipstick. These were of course pre-puberty times and no special meaning or feelings were attached to these times other than it was OK to play and pretend to be someone else.

By the sixth or seventh grade he was noticing young women who were dressing for attention and would occasionally take a second glance at the television or a magazine when an image of a well groomed and dressed women appeared. He also was paying closer attention to me and my grooming and dressing habits. I was in my late 30's at the time and, having been single for a long time still dressed with style and with a degree of allure. My position of administrative assistant required me to look properly put together every work day as my world was filled with executives and VIPs.

I still recall one evening after work at home with Ed. I was performing a few touch ups on myself prior to meeting a group of friends for dinner. My bedroom door was open and Ed came in and sat beside me as I applied a fresh coat of lipstick and gloss. With a inquisitive tone and with a trace of apprehension in his voice, Ed said, "Mom, you look so pretty and your lips shine just like the fashion models in your catalog. Does all that stuff you put on your face feel good?" I answered, "Honey, I'm not sure if it all feels good but once I have it all on I feel very good about the way I look. It gives me confidence and makes me feel like someone special". "I really like the way your lipstick matches your fingernail polish, Mom. And I like the way you look in your clothes and shoes". I hugged and thanked him for his compliment but took his comments in stride because I had an inkling what feelings were starting to awaken in him.

While slipping into my heels and checking the contents of my purse, I said to him, "It is so sweet of you to notice my appearance and pay attention to all the effort I put into looking good. Sometime soon and if you like, we can let you try a few things so you can experience it for yourself, just to give you an idea of what women go through to look good. Who knows, maybe you'll think it is fun!" With that last little zinger I'm sure I got his attention. I then gave him another hug and went off to meet my friends.

Fast forward to a rainy Saturday afternoon. We were sitting around playing board games and trying to stay entertained when I noticed a chip in my nail polish. I reached for my purse and pulled out my color coat and clear, and proceeded to do a touch up. Ed's attention was drawn from the television to my bottles of polish and nails. "I see you're interested in my polish, would you like to see what it is like who wear it?". "Oh Mom", he said, it is kind of interesting but it's meant for girls only". "Well, we are alone and no one else will know if you want to try it. Besides, some men get their nails done and polished but in clear coat and shaped differently." Sensing his curiosity but with a degree of trepidation I made the decision for him, taking his hands and inspecting his nails. They looked good enough without shaping his nails for a tryout, so sent him to wash his hands while I laid things out. As we started, I explained how his nails must clean and dry before we apply a clear base coat, and that a base coat is needed so that all traces of color can be removed afterwards, As the base dried he felt the coolness on his nails then the tightening of the polish.

We proceeded with two coats of of my favorite color for workdays and casual looks. Before long, he was sporting nails done with OPI Tickle My France-y and they looked rather amazing. We giggled together like schoolchildren while we compared our manicures, then headed to the kitchen for a treat of ice cream. Over the next few years we repeated this indulgence and sometimes when we were bored and with seemingly nothing to do we talked about girl's things while I dabbed onto him some basic makeup. Ed enjoyed these sessions but it didn't seemed to strike a chord with him which for the time was all the better and I was happy we could spend time together and occasionally prank around some.

Another fast forward, to his sophomore year of high school, and Ed was on the verge of manhood but the body changes induced by puberty were not yet pronounced. He was beginning a growth spurt but had not yet blossomed out. He was keenly interested in girls but had not yet developed a serious crush or for that matter found a girl to just pal around with. So, we spent a fair amount of time together as a family unit on the weekends. In September I received an invitation to a Halloween gathering being put on by a local charity group we occasionally volunteer our time to. The invitation encouraged costumes and on a lark I replied we'd attend. I had and older costume, Supergirl, that I could easily update for myself and to this crowd it would be new. I made a mental note to let Ed know of the party in the next few days and let him ponder over a costume. Later that week at dinner I mentioned the party and and asked Ed to come up with an idea for himself. He wasn't exactly thrilled with the idea of going to a costume party among people he barely knew, but I assured him we could have a good time. Three weeks of procrastination later he hadn't put any thought into it, so I said, "Never mind then, I'll come up with a costume for you but you must promise me you'll follow through and wear whatever I come up with". "OK, fine" he replied as he couldn't be bothered. This irritated me more than a normal teenager brush-off so I thought to myself, "OK buster, game on, you're on the hook now."

I called my older sister Ruth later that evening, sharing with her my little dilemma and my rankled feelings. Much to my surprise she laughed and said, "Oh don't fret, I have the perfect costume and payback for your little prima Donna, and I hope you let me join in the fun". Puzzled, I paused before Ruth connected the dots for me, "I still have my daughter's wardrobe from her high school and college years hung in her closets and I think we can find your little missy an outfit that will catch his attention and make him a standout at the party!" Big sister had once again come through for her little sis! I laughed myself silly talking to Ruth about her zany idea and we agreed on a plan of action.

A week before the party I took all of Ed's measurements and dismissed it as necessary in order to find a costume and let him know that time was short so we only had a few days to get it right. I then found his shoe size in a pair of his sneakers and used an online application to convert to women's sizes. Later that evening at Ruth's house we looked through her daughter's accumulation of clothes, everything from gymnastics to formal gowns was neatly organized and hung in her closets with care. Converting Ed's measurements yielded a dress size of 12 which was pretty well matched to Ruth's daughter's size in her middle years of college. We decided a formal gown would be was a bit too much for our plan, and ended up selecting an above-knee cocktail dress. To get the shoe size right, Ruth dipped into her wardrobe and retrieved a nearly new pair of four inch black patent pumps and located a middle size purse in the glossiest black patent imaginable. We both glanced at the patent leather heels and purse laying on the bed and shared a devilish smirking smile. "Oh my", was all I could muster as an image developed in my mind of a misbehaving male who was cajoled into donning a dress and high heels. "Perfect" Ruth intoned, "the little dear will have the experience of a lifetime and learn the lesson of 'look before you leap'". Her comment had me in stitches!

I allowed Ed to stay home from school the day of the party so there wouldn't be a last minute rush to get home, get ready, and make it to the party by 7pm. I talked to the party chairwoman and got an invite extended to Ruth so she could tag along. She'd come over about a half hour before the time to leave for the party and bring her photography gear and a few props so we could make some lasting memories. I got myself ready and into my costume, and called to Ed to come sit with me. He joined me at the kitchen table where he found me shaking a bottle of blue nail polish. He didn't have a clue about his costume or Ruth's involvement. I sat him down and told him he'd need to have his nails polished blue to pull off his costume and while somewhat startled by this I deflected his concern and reminded him of his promise to wear what I selected. Since he was accustomed to having manicures he relaxed a bit and I proceeded to paint his nails while he chilled and closed his eyes. In fact, he didn't even noticed me finishing the color coat and applying the clear gloss coat. "OK I'm done" and he looked down at his hands and said "Was this really necessary?". I deadpanned "I'm sure you'll thank me later, now get into the shower and wash yourself from stem to stern", and with that left for his shower. Just as I was laying out his outfit on my bed Ruth knocked and let herself in. She carried a bag and said since the party would be at least 2 hours long we should take pity on Ed and have him change into less challenging heels for the party... but not until after the photo shoot.

I checked on Ed and told him after drying to put on his robe and make his way through the hall and over to my bedroom. When he did he had his second surprise - "Aunt Ruth, what are you doing here?". "Oh, your mom was nice enough to invite me to the party since I helped her with some ideas for your costume. Here, hold on to these, you'll be needing them" and with that handed Ed a shoebox that he promptly took the cover off. The look of confusion followed by disbelief washed over his face as he realized what was within was part of his costume. He pulled out one of the black patent t-straps and held it up, "I don't care what my costume is I certainly won't be wearing these women's shoes!" . His mother popped out of her bedroom replied, "well dear you can take your pick between those or the dressier versions we'd already picked out. Let me show you", and the threesome proceeded into the master bedroom, where all the attire and accessories had been carefully laid out. Besides the 4" patent stilettos he saw the shiny purse and the entire ensemble awaiting his dressing: A lovely blue cocktail dress adorned with sequins, slip, a matching bra and panty set and a package of pantyhose. Ruth spoke,"You can thank your mom that you'll only have to wear pantyhose, I thought you should wear a girdle and stockings for the full effect". "Mom, please don't make me wear these things to the party!". "Ed, the time is passed for making those decisions, maybe next time I ask you to do something you'll pay attention and follow through. You are absolutely going to wear these things as Ruth went to great trouble for you. If you are afraid of being embarrassed, I think I know a way to save you any ridicule and anxiety, but it requires you to cooperate in the fullest from this point on". Sensing his defeat, he let the sisters lead him over to the bed where they began to fit the young man with the feminine finery. After donning and adjusting the attire on Ed, he was very quiet and put up no further resistance while the ladies painted and powdered his face. Somewhere between the false eyelashes, eyeliner plus shadow, and the lipliner, lipstick and gloss, Ed's looks were transformed into that of very-well put together young women with all the trimmings. The addition of the wig and earrings almost seemed superficial to the look because he was passable without.

Ruth picked up the shiny pumps and spoke to Ed "Now, your choices are to wear these all night or to just for a few minutes while we pose you for a few snapshots". He obediently sat on the edge of the bed while Ruth slipped the pumps onto Ed. Ed was helped over to an overstuffed chair and his sitting position was adjusted for maximum effect. Ruth, always a devilish mischief-maker, brought over his purse and placed it in his lap while she handed Ed his lipstick and compact. "Open it and hold the lipstick with your right finger and thumb just above your upper lip as if you are about to apply a fresh coat, and position the compact so you're looking at your lips in the mirror". Ed's mother rolled her eyes but it was lost on Ruth, who was busy composing some of the more exotic glamor shots she had ever taken.

There was very little additional drama that evening. Ed was completely passable, so Ed's mom told the partygoers that her son had a queasy stomach and couldn't be there, and this is my sister Ruth and her daughter Ellie. Ruth apologized for Ellie as she temporarily lost her voice while recovering from a sore throat and was following doctor's orders to remain mute. Almost none of the partygoers knew Ed and at best had only seen him in cameo accompanying his mother to past gatherings, so they never drew the association. Much to his credit, Ed came around and loosened up, enjoying the party after he realized people did not see a guy in a dress but saw a beautiful young women. Ruth practically reveled in her mother-daughter role. Her frequent whispers to Ed were not the typical party chit-chat but instead were coaching tips on deportment and praises. Of our threesome, It was clear Ruth was enjoying herself the most but I sensed that Ed was not far behind, Now, that was a party!

That was 10 years in the past, and I had occasionally wondered if Ed enjoyed himself so much that he repeated the experience. After the party I overhead him thanking Ruth and said to her the dressing and the party was like a "kick in the head". We never repeated the experience but occasionally Ed would drop by his Aunt's house for a social visit or to assist her with an odd job; I often wondered if something was afoot, but I love them dearly and minded my own business.

While Ed and Claire finished up the dishes I went to my bedroom and pulled out the album from the evening of the party. "Claire, when you have a moment I'd like to show you something you might find interesting." Ed finished rinsing, drying and storing the dishes while Claire and his mother leafed through a family picture album in the study. Even through the study's glass doors he heard the occasional laugh or exclamation. He thought it nice that the two had bonded and could share some pleasant moments together.

The End

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