Close this search box.

Logistics Part II

Lisa continues her breakdown of the realities of being who we are.

By Lisa P.

Previously I posted a lengthy essay outlining three of my particularly challenging logistical challenges presenting as a woman to the world. I talked about the difficulties in creating a hiding place for my feminine wardrobe, the risk of discovery when heading out the door and having time constraints. As I hinted in that essay, I know for certain that you have a number of your own logistical issues, because I have enough for this essay and at least one more. This time, I want to address the difficulties associated with creating a wardrobe, being “out” in the digital world and dealing with the expenses associated with my female activities.

1. Acquiring Clothing

Early in my crossdressing days I would “borrow” (temporarily use) clothing from my sister (when I was still in the house we shared as children) and my wife (after I married young). I was fortunate in that I am not all that differently proportioned (except in the obvious places) from them and could fit in many of the clothes, especially if they were made of a stretchy material. But the desire to have something all my own was very strong, as anyone who adores feminine clothing will attest. I seem to recall that my first efforts involved taking the Victoria’s Secret catalog that arrived in the mailbox for my wife and using it to buy clothes (if my recollection is correct, in the early days they carried a much bigger variety of clothes) and then having them delivered to my work address (so that I could pretend, if asked, that I was buying gifts for my wife). Unfortunately, when I made a major purge in my early thirties, all of those clothes were sacrificed, as it would be fun to see those clothes today.

I also took zero photographs, probably because I still sported a moustache, and I had no interest in seeing what “that fellow” looked like in feminine apparel. It was enough to know what I felt like inside wearing my own female clothes. As I have written about before, I managed a five-year hiatus, when I did not dress. I didn’t think I was “cured” but I thought I could keep my urges under control. But, as so many have observed in their own way, the urge after a purge can become urgent. Once I woke up from my five year “nap” I needed new clothes and I needed them immediately. I began to buy clothes every way I could think — by catalog again and by visiting stores in the mall and telling them I wanted to buy clothes for my wife or daughter (depending on the store and style). I quickly discovered (as we all must do at some point) that men are woefully unprepared to find female clothing that will fit them. Different brands had different styles and my frame was wider at the top than at the bottom. What a pain!

I had to either get up the courage (again!) to go back and exchange the incorrect item, or I had to curse myself for wasting my money when something didn’t fit quite right. I still own a top and skirt set I bought about 30 years ago. The very short swing skirt has bright yellow flowers set against a contrasting black backdrop. The matching buttoned up short sleeve top was wonderfully cinched at the waist and was solid black. I bought a size medium for the set and quickly discovered that the skirt was a tad too big, and the top was way too tight to button. In the end, I went back and exchanged the medium top for a large. Going back in time that far, those clothes are out of style for a woman my age, but I keep them for emotional reasons as a connection to the young, emerging me. Speaking of which, I find way too often that I have an emotional connection to clothing, which means I now must remind myself to give away or exchange something as soon as I buy something new. The one closet I can use is the size of a large refrigerator and would never hold everything I have ever bought! Another item I keep, for no good reason other than an emotional connection, is a stretchy pull on, knee length maroon sleeveless dress I bought at a discounter more than ten years ago. Why do I keep it if I never wear it? When I was in the check- out line, the woman ringing me up observed, “isn’t this a lovely dress; it will be perfect to wear to work!”

It was such a cute comment I haven’t forgotten it. It doesn’t matter whether she knew I was a crossdresser and likely didn’t plan to go to work in that dress – it was just the sort of thing a nice cashier would say to any patron!

Like all women, I continue to struggle with finding the right clothing that fits me well and looks great on me these days, but after decades of buying, I tend to know how to eye things on the hanger. Also, I try on just about everything before I buy it, and I work hard to round out my wardrobe so Lisa can go out year around, in any kind of weather and to any kind of event.

Editorial comment here: When I made the very first purchase once I decided to go down the “Kandi” road (purchase to keep), I purchased a bra, panties and a slip at a deep discount store. I will never forget this exchange. The woman ringing me up, while this guy stood before her, said women just never buy slips anymore. All I could think, but didn’t then have the nerve to say was “Neither do men!” Back to you LP….

2. The Digital Domain

Humans living in the Information Age use, store and communicate electronically. If you have more than one gender, however, suddenly the internet and all that it contains can become its own logistical quagmire. I don’t need to remind this audience about Kandi’s issues with Facebook. She knows that my own FB account teeters on the edge of being deactivated by the company, because I decided that discretion counted more than honesty with a company that simply wanted as many users as possible to make money on advertising revenue. Thankfully, I don’t need that account anymore. I began it during the early days of FB (about 2006), when I was young(er) and impetuous and a person could become friends with anyone simply by asking. Ah, those carefree days! They allowed me a window into daily women’s social issues that I couldn’t get otherwise. There were no honest exchanges between me and my “friends,” however, because to do so would have outed me. Accordingly, none of the people who are my FB friends really are my friends; they don’t know the real me.

I have had a Hotmail account for 25 years (imagine that – I didn’t even have a true female name at that time) and a Gmail account for 13 years. That latter account, in my female name, is very important to me. I absolutely depend on it. I can’t imagine what I would do without it, because so many of the cisgender women and transgender women who support me communicate with me via that account. Yet, neither one of those accounts is in my legal name. Thus, like many of you, I remain at risk of being “digitally deleted” and suddenly losing email addresses and important correspondence. Microsoft, Alphabet, Meta, please be kind to your princess-shoed friends!

How does one become a new someone without a digital connection? Moreover, in addition to the risk of losing that connection, there is the even bigger risk of discovery by someone who doesn’t know this part of us. I am reminded of Amanda’s recent missive about being outed to Mrs. A. All it took for her was unintentionally leaving a digital gateway active. For us, it might be a computer window that wasn’t closed because we were in a hurry. An email sent to the wrong person (who hasn’t done that?). A person who dislikes us who hunts our digital trail. All of these risks are real. The risk that keeps me up at night, however, isn’t on that list. Today, one cannot walk into a store without that store having the right to scan your face to match it against a database using artificial intelligence matched with facial recognition software. I knew that when I walked down the streets of London someone somewhere always knew who Lisa really was (if they wanted to know) because public cameras are ubiquitous there. Moreover, software readily available for sale on the Internet today claims to be able to match every face against every other face on the Internet. What is sold to consumers today isn’t as accurate as what the stores and the government use, but it is getting more powerful every day. Where can a girl like us hide?

To be honest, even if we have been able to do it to some extent, we may not be able to hide much longer, unless governments get involved and legislate greater protections for one’s digital image. In the meantime, I am determined to do what I can to foil the AI that is guiding the facial recognition software. I make subtle changes to photos, not to enhance them, but to make it harder to recognize me, such as allowing hair to hide part of my face. I use wigs for photos even if I am more likely to go about my daily business with my natural hair. Even my makeup is designed to subtly change significant features and to change my natural complexion. And, if I am aware of the location of a camera, I turn my face to the side so that it can’t get a full frontal shot. Will these tactics work? Only for some purposes and only for a limited time.

My daughter asked me not to post any photos of Lisa (sorry, too late). One of my friends from Kandi’s Land (who I will not name for obvious reasons), commented to me personally that she is relying to some extent on the fact that we are in a small, out of the way corner of the Internet. I know Kandi doesn’t want to hear that and she is doing everything she can to build readership. Even 10,000 readers though is infinitesimal compared to the billions of human and robot beings trolling the Internet. For now, someone would have to know where to look to find us. Which helps, a bit, in terms of dealing with the logistical issues of both wanting to be heard but also wanting to remain relatively anonymous. Good luck to us all as the Brave New World might await us, where our only hope will be ingesting a daily happiness drug to take our minds off our need to express our female selves….

And don’t get me started with Apple. I take hundreds (nay, thousands) of iPhone photos (as I am still trying to find a hint of the beauty I know is in my soul!). Apple’s AI allows it to quickly “match” any photo with the Mr. Lisa photos. And sometimes Lisa will even unlock the phone, which means the phone “knows” exactly who is under all that makeup! Rather scary, just like when I lift my wrist and Siri blurts out on my iWatch, “I didn’t understand that.” I wasn’t talking to Siri (er, Apple), but she was listening. A rather disturbing proposition for someone in the closet. No matter how dark it is in here, they apparently can still see me crouched in the corner! I try to make light of the matter, but I am dead serious that digital encroachments like these threaten our ability to be ourselves without the risk of disclosure.

The ultimate solution is not to care if anyone else knows. Unfortunately, I am not there yet myself.

3. Expenses

Expenses, expanding, expensive! As you read number 1 of my logistical problems above you will have heard in my words an awful lot of retail therapy going on. Buying an extra set of clothes costs a lot of money, that’s for sure. Justifying one EXPENSE easily can become justifying a number of similar expenses in an ever-EXPANDING cycle, with the result being that being a crossdresser quickly becomes very EXPENSIVE!

I have said before that spending money in this manner within a marriage that shares a checkbook can be a daunting task. It necessitates subterfuge and misdirection (or, more accurately, lying). No need to revisit that issue. My solution has been to try extremely hard to limit my purchases. Lisa has her own budget and I strive (but admittedly fail) to live within that budget. Lisa also buys a lot of resale, and she makes do with budget jewelry (treasuring the few things she owns that are 14K or 18K gold). Because I treasure my marriage and want the world to know I am married, I bought a wedding ring and band…. for US$36. No diamond ring for this girl. I also try to do what every other woman on a budget must do, which is to try to buy things that can have more than one use, such as tops and slacks that can be mixed and matched.

There is much more that could be said about spending money, of course. Many of us simply don’t have an extra farthing to spare for our female side, which means that the suffering is compounded (no money, no clothes, no smiles).

One more set of logistical challenges is still to come. I will finish Part III of this series soon, I hope. Please stay tuned to this station if you want to hear more.

In the end, I strongly suspect you have had nightmares about one or more of the issues I have been discussing if you are in the closet about your crossdressing or transgender status. Like all my bad dreams, however, when I come to my senses, I usually find a way to thrive despite them. I hope you can do the same!


11 Responses

  1. Another great post, Lisa, I’m loving this series!

    Strangely, despite my activities being almost totally covert, I’ve never had any worries about buying clothing. I just remind myself firstly that the sales assistants have better things to do than pass judgement on a buy queuing up to pay for female clothes and secondly that there must be any number of guys who have been ordered by their wives to pay for their stuff while they continue browsing. I’ve only ever had one comment made when paying for a pair of tights at a supermarket – ironically Mrs A had put them with the other shopping and left me to pay while she carried on browsing (what is it about supermarkets that’s such a fascination?!).

    Ordering for home delivery is a completely different proposition, of course. I hardly ever do it but can almost guarantee that when I do, there’ll be a problem with the delivery being delayed to a day when there’s a higher likelihood of Mrs A being at home when it comes! Amazon lockers are a godsend but sometimes home delivery is the only answer to getting what I want.

    And, as you pointed out, I am living (mercifully still living after what happened!) proof of the dangers of computers! I learned the hard way that no matter how careful we think we are in covering our tracks, we can only ever plan for those events that we realise could happen. It’s everything else that we either write off as being impossible or is so implausible that it doesn’t even cross our mind that’s going to catch us out!

    Looking forward to part 3!

    1. Amanda,

      Thank you for your comment and affirmation. I forget how lucky I am that I can have things delivered to my work address. I will follow your lead and use the Amazon locker (at least for them), when I am retired. I will definitely need to plan ahead. Another logistics problem to solve!


  2. Lisa,
    A great article. Very well written.

    You continue to discuss our common issues, which reinforces that “I am not alone”.


  3. Lisa,
    I wonder how many of us hold onto clothes for sentimental reasons , we have to admit clothes are special to us , the reasons are often more than skin deep .
    The use of names and ” handles” is often a tricky one , I will have to make a definite decision if I wish to book a holiday abroad . Many banks , shops etc will accept sufficient changes to make everyday living comfortable , obvioulsy being fulltimeI don’t have to hide my identity , so I have no hidden secrets . All I ask is they no longer use ” Mr” on official documents . I admit I have to still sign birthday cards to certain family members in my male name . Again it’s not such a big deal as I chose to use a female form of my male name so my initials remain the same which has proved sensible with my bank etc .

    You make an interesting point about being identified simply by walking down the local High Street and visiting various shops and cafes . Recently I was checking out Google Maps on my mobile phone and was shocked to see all my movements had been tracked for the last 18 months , they knew every outlet I’d visited even to the point where each venue had a thumbnail picture . I had no idea this was happening and I wonder how many others don’t realise . Again it’s a case of technology not offering the option to ” opt out ” so by default we are ” opted in ” .

    Buying from retail outlets isn’t a problem for me but annoyingly many outles don’t stock the full range , in fact some items are only available online , I appreciate most stores will order online and allow you to collect and try on in store . As you mention sizing is the problem , I tend to stick to brands with ” true sizing ” , I know I’m a UK size 12 so it’s comforting to know I can rely items that will fit . The same applies to shoe sizing , I steer clear of Chinese imports bought through the internet , they never fit , usually at least one size too small . Next shoes tend to be over sized , OK you can buy sole and heel grips but there’s no subsitute for a correct fit , sloppy fitting shoes are as bad as tight fitting ones .

    1. Teresa,

      How could I have missed shoes? The bane of every woman’s existence. Impossible to buy online (unless you have bought same she’s before) and even when you try them on (which I always try to do), I often find that they have grown tight or loose between the store and my home! I take (small) comfort from the fact my wife has the same complaint.! The situation is exacerbated by my aging (widening) feet, which don’t take kindly to be squeezed into most heels these days!


  4. Lisa,
    Retail therapy can be fun, but i can also be expensive. Lisa, you need to learn the art of window shopping. It can be just as much fun as retail therapy. You can still try things on, but it does mean you have to buy it (then). Go on the internet and put it in a cart and wait for a sale, if you can. I just did this at VS yesterday. Also sign up for rewards, get ALL the discounts you can.

    I try to keep a very low profile on the net, no social media accounts, no images with my face. That being said, I just found an image of my ankles and feet wearing Freebird platform mules in an image planel from Google.
    AI is here and it is everywhere.

    Stay safe.

    1. Cali,

      Good advice. I definitely do a lot of window shopping too. One of my favorite pastimes is to try on the most expensive dresses. I (think I) look fabulous, because the dress is fabulous, but the cost means I am never tempted to buy it.


  5. Kandi – “women just never buy slips anymore”

    You are right, but Trans and CD ladies of a certain age sure do! I love my slips. A staple of my wardrobe and daily outfits.

Leave a Reply

Your email address will not be published. Required fields are marked *

Featured Posts

Get The Latest Updates

Subscribe To Our Newsletter

Sign up for the first look at Kandi’s outfits, blog posts, and product recommendations.

Keep Reading

More From Lisa P.