I am a new reader but a long time believer in the goals of the women's movement for equal treatment and rights for women. Recently I was doing the dishes after dinner one night with my daughter-in-law when the topic of female leadership in marriage came up. She has obviously added a few softening touches to my son's overall appearance and I mentioned this to her in a complementary way. She replied with a knowing smile that she was grateful to me for laying the groundwork years before and said I might be interested in PDQ. After taking a look, I felt compelled to share with you how I sensitized my son to the feminine mystique and lifestyle. Doing so has enriched his life and the lives of those around him.
To keep this to the point I'll fast forward over my methods of raising and nurturing him and skip to the relevant incidences. I When he was in fifth grade a classmate came to school with his nails painted as his sisters had pranked him while he slept and made sure no remover was available. The child was of course taunted, ridiculed and was the center of attention. When my son relayed the story to me over dinner, I could sense some degree of interest and curiosity. I told him polishing one's nails can be great fun but was best done in private. I asked him if he would like to see how it felt for himself. When he guardedly said maybe I assured him it is a special treat and no one else needs to know. In the same breath I asked him about what color and style he might like to try so I could get everything we needed; obviously I found this idea out-of-the-blue but intriguing.
All he could muster was some thing pretty and grownup looking, signaling I had a free hand (pun!) to give him a professional looking job. So, on a rainy Saturday evening we sat down after his bath and proceeded to shape his nails, then add a clear base coat, two layers of color, followed by a glossy clear coat. His hands were thus transformed into those a woman in her mid twenties would kill for and I must admit I was pleased if not a bit envious as well. We stayed in the following day so he could gain some appreciation for and experience having feminine hands. We played some board games and I later invited him to sit with me for tea as I leafed through some women's clothing catalogs. Before long it was time get ready for the week ahead, so he learned how to remove the polish and then apply vitamin oil to his nails and lotion to his hands. I emphasized the importance of cleaning around the cuticles so there was no telltale signs of a former polishing,
Nail polishing sessions, while not a regular event, happened when the timing seemed right but probably just a half a dozen or so times over the next few years. When his nails were painted his demeanor seemed to shift and we talked about girls, women and relationships, and sometimes feminine fashion. He clearly continued to show a strong interest in relationships with women, yet if he had shown curiosity or desire towards men I would not have objected. I would say it was approximately his sophomore year in high school when the next steps started to unfold.
He had a girlfriend of sorts by then but it was your typical short term and very casual, almost platonic relationship. At one of the parties they attended he heard about a popular girlfriend-to-boyfriend challenge or dare that had gained popularity where the guys and girls switched clothing. He wouldn't have mentioned it if it hadn't caught his attention, but he then mentioned if that wasn't crazy enough one of his classmates parents participated in a womanless marriage ceremony put on by a local lodge as a charity raiser.
The wife was one of the event's organizers and had blindly volunteered her husband to be a bridesmaid! His classmate took some candid shots of his father, and he described the pictures with some incredulity - several of the participants were so convincing he couldn't tell they were males, I of course had heard of such shenanigans over the years but played innocent and said, Oh it sounds like good good spirited fun, such a great prank! Perhaps we can try dressing you some time. His silence did not affirm his interest but the look on his face certainly did. I wrapped up the conversation by telling hm we hadn't had a polish session in a long time but we would plan on it over the weekend and discuss dressing up further.
That weekend after Saturday dinner, we sat down at the kitchen table with our supplies, and not knowing if this was the right time or not I brought my portable makeup kit and set it next to the table. Our polishing ritual had evolved into a very pleasant experience for both of us, and why not? Everyone loves to be fussed over and pampered. The bonus for me is that he had become proficient at manicures and reciprocated by shaping and polishing my fingers and toenails - and there is nothing like a full mani/pedi session while sipping on your favorite wine. And, while I watched him shape, buff, and polish my nails I thought about how lucky his future bride would be! After his turn of being pampered was ending and while his polish was drying I broached the subject - would he Ike to try wearing some women's things? Was there a particular look he'd like to try? Would you like to groom and dress to the point where no one could tell you were not a young women?† Again, his body language relayed what his voice could not quite conjure up and with my gentle questioning I soon had him warming up to the idea. My mind raced with the though of what attire he could be persuaded to try for an adventurous afternoon. I decides not to break out my makeup kit but did touch up my lipstick and used my compact, and I noticed he watched me intently.
He had made it clear that he was somewhat reluctant to participate in this experiment. He made the point that he didn't want to look like a caricature of a woman, a man dressed as such. He seemed satisfied when I told him not to worry, I would not make him look ridiculous, and to the contrary, he would fool anyone who saw him. Of particular concern to him was his short hair and his face, not wanting to look ridiculous from the neck up. I assured him that we could easily make him passable with his still-youngish facial features, and clean complexion. What I didn't mention to him was that his keen interest in not looking the fool but rather looking the part and passable, he was suggesting more than just playing dress up. In my mind it was the first step into a feminization process that would end who knows where. Keeping that thought to myself, I told him I'd put together some items from my wardrobe and pick up whatever else was needed during one of my week night shopping trips to the mall.
I found my usually boring mall shopping trips suddenly held a new interest for me as I wanted to both surprise and please my son with the outcome of our adventure. After all, this might be the only opportunity I would have to nurture my son in a way that I hope would tech him a little about the psyche of women and leave a good impression on him.
The appointed day came a few weekends later and after a light lunch informed him we'd be getting started shortly but first wanted to be sure he was wanting to go through with this since it is one thing to casually talk about playing dress up and another to spend the entire afternoon bathing, grooming, and dressing in garb that men consider foreign, unfamiliar, and above all forbidden. Being sensitive to the time and effort I put in shopping, he said he'd be a good sport and let's get started. I suggested he sit down at the kitchen table and do his own nails while I made the preparations upstairs. When he came upstairs I instructed him, for modesty purposes, to put on his old bathing suit which was laid out on my bed and I'd meet him in the bathroom.
I took a quick walk around him and noted he had just enough body hair that it would have to go, and this shouldn't cause him any embarrassment because he had completed his high school PE requirements the prior semester so no one would see him undressed.
I slathered on depilatory crepe from his neck down over his legs, arms, underarms and chest, then had him pull up the legs of his bathing suit so I could finish the very tops of his legs. After a few minutes He washed and showered off while I ran a scented bubble bath. After jumping in the bath I told him it was OK to take the suit off and let him soak in the sweet smelling bath of bubbles, fragrance and oils. The hair remover seemed to do its job but I wanted him to feel every bit of the feminization process, so I grabbed my can of shaving creme and a new pink razor. I lathered up a leg at a time and shaved away. We made lighthearted conversation about† women's grooming and fashion while I finished up the shaving and we were both in a happy, almost giddy mood. The thought occurred to me that I might be enjoying this adventure as much as my son.
Out of the tub, patted dry, powdered down and placed in a robe, I led him back into the bedroom where he first saw what I hoped was his dream come true: a satin and lace bra, panty, and camisole set, a fresh package of pantyhose, a full length nylon slip, and a taffeta dress. On the other side of the bed lay his accessories - a pair of glossy white patent 3" heels, matching purse, and his bangles and bobbles of bracelets, necklace and clip on earrings. Over at my makeup table stood on a stand lovely mid length wig and the makeup supplies I had preselected. I gave him a few moments to take this sight in. He audibly gulped and I noticed he was showing signs of discomfort so said, It's a perfectly normal reaction and you shouldn't feel ashamed, I'll leave the room now so you can look over your finery and adjust yourself, just call out when I can come back and DO remember to first put on your panties. From the dresser I picked up and handed him a hand towel and a container of hand lotion, smiled warmly, and left the room. When I came back he was† much more relaxed and to my delight was wearing the satin panties.
For the most part he got himself dressed but I offered assistance with the bra and pantyhose. I zipped him up then had him sit while we added his earrings, necklace and bracelets. I knelt down and slipped the heels on his feet. We took his purse and proceeded to the makeup table.
Since going all-out was the theme, his makeup would not disappoint. Liquid foundation was followed by pressed powder and blusher. Liquid eyeliner, eye shadow and mascara were applied before the false eyelashes. We touched up the lashes with some additional mascara and proceeded to his lips. I applied lip liner first then opened the new lipstick which was a berry shade. I showed him how to apply the lipgloss for maximum effect. I had purchased a small makeup bag to keep his purse organized, and had him load it with the lipstick, gloss and a new compact for touch ups. After placing and adjusting the wig he was ready to see himself for the first time. He looked like an early twenties women decked out to the nines. All he lacked was the composure and confidence to carry himself as such.
And so began the first of several dress-up sessions with my son. We progressed from staying in to taking a drive, and eventually went out to dinner and a play. All the time I nurtured him and taught him how to act, think, and carry himself as a women. Contrary to what some might think, he did not develop an interest in men. I think the idea of converting a person's orientation via feminization, particularly cross dressing, is largely a myth unless there is an underlying interest or psychological methods are used to bias a person. From what I've heard from my daughter-in-law, theirs is a very healthy relationship. I am hoping someday she will share some of their escapades involving their lifestyle and dress up play.
A Happy Mother
Thank you for your letter. What a wonderful and sensitive introduction to femininity, you took your time while fully attuned to his feelings, so many mothers who might wish to share this with their own sons will appreciate your example.