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The Lure of Femininity

A beautifully written accounting of our dear Fiona's trip into womanhood.

By My Sister, Fiona Black

In all the decades during which I was a closeted crossdresser, my dressing activities concentrated primarily on lingerie and hosiery. I had been fascinated by these items since since my early teens and it soon turned into a passion in which I indulged whenever I could grab some free time at home, in hotels on business trips and during occasional underdressing excursions. But it was always just about the clothing, an item of lingerie was simply an object of interest and desire. As time passed however I discovered that lingerie was not just an object, it proved to be the key that opened the door and enabled me to begin to experience the notion of womanhood.

At first, this new interest in womanhood centered on women’s relationship with lingerie. What did women think of wearing lingerie? What did they like and why? What styles were more comfortable? What was in and out of fashion? What were the pros and cons of all the various bra styles? What were some of the different body shapers used for? How do you measure for a comfortably fitting bra? Concentrating on the relationship between lingerie and women resulted in my crossdressing gradually moving away from just a guy wearing women’s underthings to a guy wanting to better understand the wider world of women.

As I explored this, I found my dressing experiences being taken to another level, everything became more exhilarating. I became more enthralled at how wonderful wearing lingerie felt and how very sensuous my legs felt covered in nylon stockings. I discovered just how beautiful full slips were and how utterly sensual it was to finally close the last garter belt snap and feel the straps tug on my stockings. The beginnings of a sense of femininity slowly took root in my psyche and changed me forever. I soon tried on a skirt and dress for the first time and felt like I belonged in them. Years passed until in the Spring of 2022 I made the decision to dress completely as a woman for the first time. As I built my wardrobe, bought a wig and stocked up on makeup in preparation for going out in public en-femme for the first time that May, my sense of femininity grew by leaps and bounds. Applying lipstick and watching as the creamy color transformed my appearance was a thrill. Waking up in the morning and feeling my breast forms pressing on my chest was a very comforting sensation. Donning a wig and seeing the woman staring back at me in the mirror was breathtaking. Wearing a new dress with makeup, jewelry, wig and shoes, looking in the mirror and saying “Hello Fiona” for the first time was a truly memorable experience. Shortly thereafter, it was look out world, here I come and out the door I went. Oh my, I’m actually letting people look at me dressed as a woman? Better make sure my clothing, makeup and mannerisms are appropriate in order to convey a believable female image!

Men are giving me the once over and checking me out? Better check and make sure I’m walking in shorter, straighter steps, not lurching down the street like Quasimodo. Women are smiling at me or giving me appraising looks? Better make sure I smooth my skirt as I sit down and cross my legs correctly! Better make sure I’m holding the shopping bag in the crook of my left arm while my right arm is held wrist out and slightly bent! Having to be “on” all the time in public made my feelings of femininity skyrocket and I took to being out in public like a fish takes to water. These feelings were especially strong when I got glammed up in a cocktail dress or an evening gown and went out to dinner or a public event. I felt then that I had reached peak femininity, it couldn’t get any better than this!

However, it turned out I was wrong. There is one other circumstance that for me truly is indeed the ultimate in feeling feminine and the following is a good example:

I went out to a Thai restaurant for dinner one evening dressed in a short black skirt, black leggings, black knee-high boots and a loose slate blue, satin, button down blouse. It was a small restaurant and seated just in front of me were a husband and wife in their mid-to-late 60’s. As they got up to leave, the woman turned to me and commented how much she liked my blouse. After thanking her, we spent a minute talking about blouse styles. She then said that the color really complemented my skin color and makeup. Once again I thanked her and we talked for a minute or two about cool/warm color matching and our choice of colors. She then wished me a nice night and left.

This was my first longish conversation with a member of the public and I sat there amazed at how natural and comfortable it felt. Just two ladies talking about normal female things. During dinner, my eyes kept wandering across the aisle from me where two people, a male and female who looked to be in their early 50’s were sitting. The woman had a wonderful natural beauty and gorgeous long, straight, honey blond hair. As I got up to leave, I walked over, excused myself for interrupting and complemented her on her hair. She broke out in a big smile, briefly put her hand on my forearm, like women often do, and thanked me while saying “not bad for being in my 60’s huh?”. After telling her how young looking she was for her age, I told her not to feel bad about being in her 60’s because she should be glad she’s not 72 like me. Once again, she put her hand on my arm and said “Get out of here, you look wonderful, no way you’re 72!” After thanking her, the two of us chatted away for a minute or two about looks, age and the wonders of makeup. Her male companion sat there looking amused as he watched us yakking away like women do. As I made to leave, I said to her “Good night young lady” and she said in return “And good night to you too young lady”. I left the restaurant on cloud nine, incredulous at having had normal woman-to-woman conversations with two different ladies who both talked with me as if I was one of them. The feeling was incredible and very satisfying.

As I soon discovered, interacting with genetic women and having them deal with you as just another woman is, for me, the thing that makes me feel the most feminine. I have had the pleasure of numerous interactions with women in a variety of circumstances ranging from asking women in a store’s dressing room for their opinion on a dress I was trying on, to sitting with my female dentist and giggling like schoolgirls about scenes in the Barbie movie, to sitting with my female neighbor in her front yard talking about life and laughing about what dolts men can be, to comparing nail polish and offering lipstick advice to the aides in a doctor’s office or simply chatting with women about sizes, materials and designers while shopping. It did not seem to make a difference that I was a trans woman, everyone just interacted with me like they were talking with another woman. I fully understand that this does not necessarily mean every woman was accepting of my trans lifestyle. Maybe some were just being polite or in the case of a sales assistant were just trying to make a sale but the bottom line is that their interactions with me were respectful and made me feel welcomed. I am convinced that if you want to be accepted as a woman, you need to act confidently, dress appropriately and insure you are polite and courteous in your dealings with genetic women and in most cases you will be met with respect and courtesy in return.

But like the Sirens of Greek mythology, who lured sailors to their death because their voices and the lyrics to their songs were so lovely that no one could resist them, the lure of femininity is also very powerful. This was brought home to me one day while listening to the radio. The Spencer Davis Group was playing with Steve Winwood belting out the lyrics to “I’m A Man” and I yelled back at the radio “That’s your problem Stevie, I’m a woman!!”. I said it in jest but it got me to thinking about how I have evolved since introducing the world to Fiona. I have moved on and am not really a male any longer. Yes I have a male body but I have left many of the other elements that make up “maleness” behind and don’t miss them at all. I am also not a female. The reality is that I will never experience the world exactly as a genetic women does. I now exist somewhere between being male and female that can be labeled trans, transgender or transfeminine, take your pick. I have also arrived at a point where I can say I am not simply emulating a woman, which implies just copying what other women do, but am expressing my own unique, personal feelings of femininity. So my fascination with lingerie all those decades ago turned out to be the key that unlocked the door into womanhood and once that happened the Sirens of Femininity lured me along to where I am today. Their song was so powerful that it ultimately enabled the real me to emerge and change me into a completely different person. I am so very grateful that I heard and heeded their seductive song.

If you are struggling with all of this, if you are exploring these feelings, read and reread this post. Fi is a darling human being and was one of the reasons I agonized over cancelling my Keystone plans this week. This is a roadmap for wrapping your head around your feelings. A manifesto for what it is, what it can be. Thank you Fi for being, well, you!


20 Responses

  1. Fiona, that post was one of the all time greats here. You demonstrated the simple premise that acceptance has to be earned not demanded but providing one acts in a way generally befitting of women in society, acceptance is almost always there for the taking.

    Kandi was spot on in her comment at the end that this is a post to be read and reread. I’ve already gone through it twice and it’s only been on the site for 30 minutes!

    A true masterpiece!

    1. Thank you so very much for your comments Amanda. I’ve found it remarkable how women have dealt with me. These interactions always boost my confidence level which, as you know, is so important in successfully presenting as a woman in public.

  2. A beautifully written account Fiona! I am enthralled with your description of how you were overtaken by the sirens of femininity (an incredible and spot on analogy BTW) to become the feminine person you embody today. Altho I am not 24/7, I can relate to the exhilaration of connecting with others, and the amount of time and deliberation that goes into each presentation I prepare, especially now in the run-up to Keystone. Best of all, it never gets old!

  3. Fiona,
    Whatever opened the door for you in the past it has had a wonderful conclusion .

    Your account is spot on especially the paragraph about acceptance , how to truly integrate . As you know I’m now fulltime as Teresa so I don’t even consider what labels society may or may not use I’m simply Terri to most of my friends . Being the same age as you has mixed blessings , I enjoy my life so much now , the concern is can I sustain it ? In some repespects I don’t have a choice as I’ve finally officially applied for a name change . I had a reminder to renew my driving licence so I thought if it doesn’t happen now it never will . So after a battle with the passport office I can now travel as Teresa and if I’m stopped by police my driving licence is now correct .

    You appear to see the situation very much like me , nowdays it’s not so much the appeal of being a woman but the lack of remaining a man . I found there is nothing left for me now , a female lifestyle is so different and freeing , female friendships are more genuine .

    I really wish you the very best and hope you continue to enjoy life as Fiona , it’s a wonderful place to be .

    1. I agree 100% Teresa. Living as a woman is a wonderful way to experience life. All the best to you too!

  4. Thank you Fiona for a great post. It really cheered me up. I had to cancel my visit to Keystone due to family issues. It would have been 9th or 10th visit.

    1. Thank you Terri. Sorry to hear you will miss Keystone, this is my 2nd one. I promised Kandi I would do another Keystone wrap-up this year so you will be able to see some photos from Harrisburg then.

  5. Fiona,
    You are so right about the joy one can get from just a ‘normal’ conversation as two women. Although I don’t outly dress as a women, I am almost always dressed as a women. I have frequent ‘normal’ conversations with women about my heels and nails. Sometimes I will have a conversation about a top or outerwear I or they have on. For example, at a lunchoen Friday, I compared nails with a female friend while the other males at the table seem amused.

    Keep enjoying life.

  6. Fiona,

    A wonderful post. You managed to accomplish in 2 years what it took me a lifetime to do. But I am finally me and enjoying every minute of it. I too love talking to cisgender women — particularly my girlfriends. I enjoy girl talk much more than boy talk (although after a lifetime I am good at faking boy talk, I think!).

    Also, thank you for being such a wonderful ambassador for our community. I can tell that you are. We need all we can get, as we are misunderstood by too many folks (and thank you to all the cisgender people out there who love us regardless of what a minority may think!).


  7. Thank you for your nice comments Lisa. I try to always be conscious of the fact that any interaction I have with a member of the general public may indeed impact how they think of all other members of the trans community. After I have interacted with some of these women a few times I always make it a point to thank them for being so welcoming towards me. That gesture is often received very well.

  8. Hi Fiona, Thank you for posting and sharing your journey with us. It was so well written and pleasure to read. You should be an author. Actually you and Amanda make a great pair. You’re well written and honestly I was kind of sad when I’d finished reading it. I wanted you to go on. Thanks again girl friend, hope you had a great day.

    Trish 💖

    1. Trish, no need to be sad when you finish reading it, just start again like I did.

      Thanks for the compliment too!

  9. Fiona & Kandi,

    Chatting with CS women is one of my most rewarding experiences. The vast majority are understanding and have welcomed me into the sisterhood as recently as this morning when my hair stylist and long time friend & confident called with a cheerful greeting >>>Girl you left a treasure trove of stuff in the shop yesterday. See you at 12:30 to go through the collection. No excuses! See you then honey. Bye”. This call made my whole day. hopefully more to follow at high noon.

    Marie Anne

  10. Fiona, that was a wonderful essay, I have found that most people you come in contact with are very accepting. I have had nothing but good experiences when I have interacted with people as Julie. I enjoyed reading all your essays.


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