Christmas Continues

This is a promised continuation of my Christmas adventure posts which furthered my confidence of surviving in a feminine world. I already have posted my shopping successes when I searched for gifts for my wife but this is a little different.

Actual photo of Clifton Mill


 At the time I was searching for things I had done as a man which I so badly wanted to do as a woman. I wondered how the whole experience would feel.

One place I gave quite a bit of thought to was a actual working flour mill in a nearby village which decorated heavily for Christmas every year

The mill and surrounding shops were normally well visited and were a great time to wear one of my in style heavy fuzzy sweaters with leggings and boots. Even though I still did have to fight off my anxiety by trying such a new idea, the excitement of finally being able to live my dream made up for it.

After I completed the fifteen mile trip to get there, the first thing I did (after I parked the car) was take a deep breath and tell myself to enjoy everything. Two things helped, the first of which was my wife again was working a closing shift and I managed to take the day off so time was not a problem. The second was it was a perfect winter evening. Chilly but not too cold so the deep breaths helped my anxiety quite a bit. 

As I began to notice, no one noticed me. I then summoned the courage to stop in one of the small shops and buy a cup of hot cocoa. Again I was treated with a smile and my courage was at an all time high. It was then time to buy a ticket and tour the mall grounds myself. As you can see by the picture, the mill itself is beautifully decorated. What you can’t see is the extra work they do with the surrounding grounds and out buildings. I was able to take my time and double enjoy my femininity as well as all of the decorations. I even bought a second cup of hot cocoa in the mill itself. Still, no negative feedback from anyone.

My disclaimer is I knowingly (or not) set myself up for success by doing several things. First of all, I had plenty of time to get ready and had the stylish clothes in my wardrobe to help me along. In fact my wife supported me enough that she had bought them for me as a gift. Second of all, as I have written, time was on my side. I didn’t have to rush and ruin this milestone moment in my life. Finally, I attempted it all under the cover of darkness. Which covers a lot of flaws. Even the places I purchased hot cocoa had soft lighting which in turn made me look softer also.

I know it is a selfish thought but the whole evening proved to be the best Christmas present I could have ever given to myself. Plus give me the confidence to continue my quest to locate and support my own femininity. It all felt so natural.

Re-Coil

 I went into the Cincinnati, Ohio VA (Veterans Administration) hospital  Friday for my Covid Booster. Normally when I go there I receive a mixed gender reaction. By mixed I mean, I can be called everything from she to being stared at and laughed at. Keep in mind, their clientele at the center includes a large rural Trumper area, so we aren’t dealing with some of the most advanced people in the world. 

The staff itself was very much neutral with me. Being careful to call me by name once I signed up for the booster. Ironically it was Christmas time at the VA with people passing out free bags of fruit and coffee. 

Since this was my third covid shot, I knew a little of what to expect. Or so I thought. I sailed through the

first day with no real effects, only to get hammered the second day. I called it the “re-coil” affect. 

At any rate, I ended up in bed watching one of my favorite Christmas movies “A Christmas Story”.  If you aren’t familiar, “Ralphie” the young central character wants a BB Gun in the worst way.  True to form Ralphie, almost immediately breaks his glasses with his new gift…a BB Gun. When the gun recoiled when he wasn’t expecting it to. 

In my corresponding youth, as badly as he wanted the BB Gun, I wanted a doll. Needless to say, I never was gifted with a doll. Plus, never in a thousand years would I ever had the courage to ask for one. 

I never broke any glasses with my gun but my brother did manage to shoot me with it. 

I would like to imagine in the future, gender roles could be loosened and  a boy could receive a doll and a girl could receive a BB Gun with no questions asked.  

Christmas Lessons

I have been saving a couple posts for the time when we came nearer to the Christmas holiday itself. All of them involved me taking advantage of the opportunities to gift shop for my wife. Essentially, I was doing the wrong thing by sneaking out behind her back for all the right reasons by finding her just the right gift. 
It just so happened she was into vintage gardening items so any trip to an antique mall was a great start into finding her a gift. Routinely I used to cross dress as my authentic self and make the trip to local and regional antique malls. I was fortunate in back in those days I brought home a good wage so I had spendable income to come up with a great gift or two.

What did I learn? Essentially two things. The first of which was the basic dress to blend plus I had to leave the heels behind for comfort when I was heading to the antique malls. However, on occasion I did go to an upscale mall over in Columbus, Ohio to shop for a new garden gift in a couple of  specialty garden stores. In fact, I often broke my own heels and hose rules. In my own way I was dressing to blend as many other women were dressed in a similar way.


One night which stands out in my memory was the time I ventured out to buy my wife an oak bookcase to match the roll top desk we previously purchased. My wife was working a closing shift  in the bookstore she managed so I could know where she would be and till what time. .For whatever reason, I chose my black pantsuit, flats, long blond wig, along with my full length black coat.  

As I headed back to Columbus, Ohio for my purchase, I knew exactly where I was going but my anxiety level was still at an all time high because I was fearing how I would be treated. 

I wondered on the other hand how I would ever be able to load such a large object in the car by myself. Little did I know I had nothing to worry about because the store had two young guys ready, willing and able to load my purchase.

I was treated to a thank you mam’ and off I went with my purchase. I had to get it home before my wife returned from work. The trip took about a half hour one way and the best part was I was able to hide it in the garage away from prying eyes.

Maybe though, the best part was proving to myself I could exist successfully in a feminine world. Once again I had “survived” and could move forward again .

It turned out there were several other Christmas lessons to come.

Fun on a Bike?

Actually I didn’t have any fun with my imagined wig hair (back then) blowing in the wind plus having my hands wrapped tightly around my new crush’s waist. I was never able to beg my way into a ride and I never tried. I’m sure you remember the post I wrote about the experience. 

Long time Cyrsti’s Condo reader (and co-founder) Connie Malone does and commented:

” I’ve known you long enough that I recall discussing with you what to do about the biker guy at the time. It was fun girl talk, with lots of anticipation. Although it wasn’t a fairy tale ending, it still created much drama.

Photo Courtesy of
Connie Malone 

The banana thing never appealed to me (intended). I guess I’m penis- averse in general, and even more so concerning my own. I have been asked for dates a number of times, let alone the numerous hits I’ve had to endure – mostly on the unsavory side. I did meet with a fellow band member for dinner one night before a rehearsal, but it wasn’t really a date. He was just a really nice guy who totally accepted me when I came out to the band (a whole story in itself), and we met as friends. I remember sitting with him in the crowded restaurant, amazed that he was so comfortable being with a trans woman in public. Of course, it was fairly early in my transition, so I wasn’t really so comfortable being in public, myself. By all appearances, we must have been perceived to be on a date by others, and I was even more amazed that nobody was staring at us. It was one of those validating experiences that added to my confidence, at any rate.

Of course, having been faithfully married to my wife for 49 1/2 years has a lot to do with any choices I would make in the dating (or beyond) department.”


Thanks Connie for the comment. I say in essence she was the co founder here is because I was sharing coming out experiences with her and she suggested I write a blog. Back in those days, I didn’t even know what a blog was, so I had to research it.


In addition, I too had a couple dates with men who went out of their way to make me feel feminine. Outside of the sexual side of being with men, I tried to learn communication skills which would help me on a date. Naturally, I was scared to death but survived anyhow. One of the men in particular wasn’t from the area which I lived, so he was just passing through (as I hoped I was) when we went on a dinner date. The other I left up to him to contact me if he wanted to but he never did. Ironically, I was a regular in the two places we went and received great service and knowing looks from the servers I knew. My rule of thumb always was have a good attitude and tip well and it worked.


Speaking or writing about male crushes, I was pleasantly surprised to be able to watch one of my all time favorite male screen crushes on Turner Classic Movies. For some reason, I always have been fascinated with the WWII era and earlier and Robert Mitchum was my male crush way before I knew I was allowed to have one.

Robert Mitchum

Of course, any ideas of having a male crush were stifled and mis-understood. To the point I couldn’t even dream of him for fear of what was happening to me. It all makes sense now why I didn’t really crush on any famous cis women celebrities. Of course I wanted to look like them but did not desire them sexually.  


It was all part of my gender puzzle I have written about in the recent past.
As far as motorcycles go, without a doubt I am sure Robert Mitchum would look great on one. Plus I am sure Connie was a suburb dinner date. As far as I am concerned, I was single during the dates I wrote about. So now I wouldn’t even consider such a move.


It’s always fun to consider the “what if’s” of life and how everything turned on a dime (or quarter). 

Masks

Another Cyrsti’s Condo reader I have been in contact with over the years wrote in and commented on her feelings about applying makeup. Her name is Mandy and she lives on the East coast of the United States. Over the years she had been able to survive balancing her life in a feminine world along with living with a spouse and having young grand children.  

In the comment (thanks), she said she viewed the whole process as applying a mask. Admittingly I think she is right in many ways. I know back in the day when I first started experimenting with basic makeup skills it was a process. Something I had seen my own Mom do so effortlessly with her own makeup proved to be so difficult. Of course there are no pictures but I am sure “clown like” would be applicable. 

Cis Model with mask being applied
Photo credit: Chalo  Garcia (Unsplash)

Still I endured, bought my own makeup and embarked on a process of improving my makeup skills. Slowly but surely I was able to improve my “masking” skills. 

When you think about it, all women (cis or transgender) use makeup as a mask. These days, much to the chagrin of many transgender and/or crossdressers, women have moved to a more natural look. Which means much less makeup. I noticed an example as another much younger woman stood in line ahead of me at the dentists’ office. She was wearing very little makeup except mascara and perhaps lip gloss. Of course with her youthful flawless complexion she didn’t need any mask. Her whole demeanor screamed female. I was envious in that I had to put much more work into my feminine presentation. 

Unknown to me however was what kind of skin care routine she used. I am fortunate in that I was able to “sneak” in my own personal skin care routine. The act of shaving probably provided me the greatest benefit when I was able to exfoliate old skin cells and replace them with new ones. Then I was able to convince my wife I needed a moisturizer to help me with razor burn. In fact, one of the biggest recommendations I can make to novice transgender – cross dressers is take care of your skin. The second is watch your weight. It is a real possibility you will be able to present better as your feminine self if you follow those rules. Your “mask” will come along with practice.

These days locating help with your mask is easier to find. If you live near big urban areas at all, makeup specialty stores often are happy to help you with tips. There is so much to consider with contouring and color.

I was fortunate enough also to be able to undertake hormone replacement therapy, which really helped to smooth out and soften my skin. Plus age alone aided my transition. I was of the age where the binary genders have a tendency to blur. 

Whatever your case , I hope you can adapt to wearing a makeup mask and it helps you lead a quality life. If not, remember it’s a marathon not a sprint. Just keep working and don’t get discouraged.      

Gender Puzzle

Anna commented on Medium concerning my coming out experiences as bravery.  I have never thought my gender transition as having anything to do with bravery. Rather, it was something I had to do. Now I look at the process as more of solving a gender puzzle.

Photo-Ryoji Iwata (Unsplash)

As I assembled my gender puzzle, I kept discovering more and more missing pieces. What happened  then was I needed to accomplish more and more in the public eye to prove I had it right. I have written in depth on many of my learning experiences all along with more and more I continue to discover as I follow this writing path.  Once I think I have it all figured out, something new comes along to prove I have not.

One thing I don’t write about enough are my severe bouts  with gender dysphoria. Perhaps there was a level of bravery to overcome passive and active suicide attempts. I know I was scared to death to enter the world as my feminine self on more occasions I can count. I have often told you all about all the times I came home crying following ill fated attempts at living as my authentic self. Back in those days I was still of the opinion I was crossdressing as a woman. When, actually all those years I had been cross dressing as a man.

I need to add in also I have never been good at puzzles. I tend to approach them (puzzles) with my usual impatience. When a certain outfit didn’t work instead of trying another, I allowed the mirror to lie to me and out I would go to fail again. Slowly I did learn not to force pieces of the puzzle together that didn’t fit. At that point, I discovered I could have success in public with my external feminine appearance and learned it was only the beginning. In other words, I discovered a whole new set of puzzle pieces. 

Now, even I wonder how I managed to navigate all of the challenges I was to face. It seemed every piece of the puzzle I located and was able to find a place for created the need for another. An example is how women communicate with each other. I found they have a unique way to communicate when men are present or when they are not. I had several women who protected me from possible negative situations with men as an example. It wasn’t just men though. Along the way I learned women specialized in passive aggression. Or where were the knives located when they met you. Those were the ones who said you looked good as a woman…for a man. (un said).

The biggest puzzle piece had to be what happened when I lost my male privilege’s. I reached the point of my life age wise when the term “sir” had been bestowed on me, if I wanted it or not. Most importantly I found my personal security changed drastically as I tried to live a feminine existence. For the first time in my life I asked friends for help getting to my car at night when it was parked in a relatively unlit parking lot. Overall, the loss of male privilege deserves it’s own post we will get to another time.

Over the space of life, I learned to respect my gender puzzle as just a extra special portion who I became as a human. After all, how many people get the chance to sample life from both sides of the gender spectrum.

I just hope I haven’t lost any pieces as I complete my puzzle.

Comments From You

First of all, a big WOW and thanks to all of you who took the time and effort to write in and comment on recent posts. The first  comes from Connie:

Photo courtesy Connie Malone

“So, I went out to grocery shop to get my booster vaccine. I was quite presentable in my hair, dress and makeup, and was feeling even a little pretty. At the grocery checkout, though, there was a discrepancy in the total, and it took three employees to figure it out. During their discussion, among themselves, I was referred to as “he” twice. I guess that answers any question as to my passing. It had been over two years (maybe three) since I was last mis-gendered, but the sting still hurts and kinda messes up my day. The employee who mis-gendered me had always been so friendly and accommodating in the numerous encounters we’d had in the past. 

The one thing that is common among cis people is that they don’t very often give their gender much thought at all. I have been getting myself to that point, as well, but it’s taken many years so far. As confident as I have become with myself, though, I guess I’ve not attained everything I’ve worked to achieve. 

The only positive here is that the hurt does not last as long as it used to. Big girl panties may not be enough; at my age, I should probably be in granny panties. I did get some redemption when the immunization coordinator at the drug store did not hesitate to check the female gender box on the form. The only bad thing about the experience there is that I ended up having a bad reaction to the booster, and I’ve been awfully sick for the past two days. Or, maybe it was the first experience at the grocery store that made me sick? :-(“

That is unfortunate! I think sometimes when I think I am most presentable is when I let my gender guard down and cis people mis-gender me. I am a strong believer in the “aura” a person gives off in everyday life. So in situations with strangers I try to remember to input feminine on them. Seems to work for me.

The second comment comes from Emily:

“I came upon your writings through Femulate. Really appreciate your acknowledgement that some of us pass most or all of the time.

Some sites claim that is impossible which causes a turn-off for newbies. It also indicates a lack of self confidence on the part of the author and/or laziness to do the work.Some of your other writings discuss friendships with women –I have found that most come around very quickly. Most men remain turned off”
Thanks Emily and welcome. Yes I have always thought the great majority of us can “pass” most of the time if they put a little work into doing it. What I mean is, take the time to learn a little of the feminine arts such as makeup and clothes. Maybe attempt to lose a little weight and strive for the closest possible shave. It’s never easy but is worth it. Others may not take into consideration the years of error and trial which went into being where we are today. 

Photo Courtesy Paula  

The third comment comes from Paula : The whole question of passing will never go away. Not even just in the trans world, I hear my gay friends talking about passing as straight, and friends with Asian heritage as passing as white. Does this mean it’s about claiming inherent privilege we are not entitled to?

On a personal level I am quite sure that I never pass, especially as soon as I open my mouth! Having said that the vast majority of the time I am not noticed, these days I have a self confidence I have NEVER had before, now I just go about my business as me and nobody notices. I fear it is when we try too hard that we get noticed and give ourselves away. It is only when I glam up that people notice, that I start to get the comment like “You’ve got great legs” with the unspoken “for a man”.

I suspect that the situation may be different here in the UK with very many staying with support groups long after their own transition, It is a sorrow to me that I will be missing two meetings in a row due to other, work commitments.
Thanks to you Paula. I agree once you can get to the point of being able to just live your life as your authentic self, most of the other pieces of the gender puzzle come together. Which could be a topic for another post!

We Got Mail

Image by Kelli Stinett

 I am sorry it has taken me so long to respond to several comments on my “Passing” post as well as others. I simply have been to busy this week to contribute much to Cyrsti’s Condo. So, in no particular order, here are several of the comments. Tomorrow I will add more.

Ironically, Georgette commented she was surprised by the lack of response:

“I was hoping to have some others comment on your reflections.

Back in the Dark Ages, The other TW I knew were much older than me, Age 23-27 vice their 50s-60s, Had never knowing any TM,

I can’t recall we called it Passing but was learning to just Blend in with other women in our age groups, Couldn’t really go stealth as my entire family has accepted me, And where I transitioned at the same place of work,

To go wherever women would be and see what they were wearing and how they conducted themselves,

I guess for me as a youngish woman I did have the advantage of youth,

For those older TW they just settled into a more comfortable look, Nowadays I see so many late-in-life still want to look like those younger women, I keep my opinions to myself as most don’t want advice just affirmation, I have been blocked or un-friended when giving some advice/criticism, Even here on Medium I was blocked with no reason given.

When I decided to come back out to this new LGBT+ world, I looked at a lot of women in their 60s and decided I didn’t want to look like them, My style is a more comfortable woman but still not ready to give up on being attractive, Most times people don’t believe me when I give my age as 71.

But sometimes I wonder if going back to be mostly stealth would be easier, In the General non-LGBT+ world I am.”

Thanks for the  comment. As you all can probably tell, the number of active commenters I get in relation to the overall number of hits I receive on the platforms I write on are in a small minority, which is fine. Back to the comment. Georgette, I am of the same age as you and do my best to dress to blend in with. Fortunately I lived through my attempts at not dressing age appropriate.  On the other hand, I try to make sure my minimal make up is properly done and my hair is brushed.  I think it is slightly humorous when my partner Liz always runs to put on makeup when I do when we go out. I tell her she wears makeup because she wants to and I wear it because I have to. 

Also Georgette’s comment comes from the Medium writing platform I post to. I’m humbled and flattered to have received an award from them as being one of their top LGBTQ writers. If  you are interested, go to Medium.com for details on their service. 

As I wrote, there is much more to this post coming up from Connie, Paula, Emily and more. Thanks for your patience.

Now What? An Adventure in Sexuality

Way back when, even though I was trying completely to transition into a transgender woman, I had never given much thought to any potential changes in my sexuality. I couldn’t see myself being with a man except if he was validating me on his arm as a woman. All of those thoughts changed when I met the guy and his bike. For you purists I think he owned a classic Indian Bike. 

I’m sure through out the years I had some sort of tunnel vision about my feminine appearance. Even though I wanted male validation from how I looked, I could never imagine really being with a guy.

Of course gender and sexuality are two separate terms. For simplicity, gender is how your perceive yourself as a woman or a man (or somewhere in between.) Sexuality is which of the binary genders you wish to have sex with. Again allowing for desiring both genders is a possibility. 

Somehow growing up wanting to be a girl rather than just look like one didn’t allow me the idea of being sexual with my own gender. Looking back at my high school and early college years though, I think I did have a crush on one my closest male friends. A crush which would forever remain a secret. 

As life progressed and I interacted with my second wife while cross dressed as a woman, I had a  chance to experience what gender life would be like from the feminine side. On one of the trips we made together to a transvestite mixer we decided to stop at a tavern for a drink before we went. As we sat at the bar, a guy parked his Harley motorcycle by the front door and ended up sitting down next to my wife. He ended up having quite the conversation with her and ignoring me. So much so I wondered if she would end up leaving with him to ride on his bike. Of course I was helpless to do anything and let her take control of the situation. It was a feeling I would never forget when she didn’t go anywhere with him. Ironically, years later I would another interaction with a man and his motorcycle of my own.

I have written how quickly I arrived at the “now what” moment with him too. He was as sensitive as he was gruff looking and totally validated my desire to be a woman. I remember wishing at the time I didn’t have a wear a wig (and had my own hair) so I could beg a ride with him. But the wig I wore just didn’t fit that tight. I could only fantasize what it would be like to ride with my hands around his waist. But a fantasy would all it would ever be with him.

Later in my transition, I did have a few other opportunities to date other men. In fact one of my first dinner dates with a guy was with a trans man friend of mine. A couple other dates went relatively well but overall I had a difficult, even miserable time finding a date with a man. On the other hand it seemed I was finding my interest from women was reaching a all time high. At first it confused me until I learned to relax and enjoy it. I have written in depth about my success (to this day) with lesbians. On the other hand I was able to befriend several women and their husbands too. I suppose being a gender hybrid has it’s advantages.

To this day, now what never became a reality as I have never been with a man. Years ago I had a cis woman friend of mine who said get a banana and practice. Rumor has it, I did just in case. Or should I say “Justin Case”. I only know Justin wasn’t riding a motorcycle. 

Feminine Socialization 201

Essentially this is a continuation of my recent post describing portions of my early feminine socialization. Included  in the post, I wrote about almost being included in a bachelorette party get together. I say almost because I was briefly invited then heard nothing more about it. I didn’t give it much more thought because the marriage only lasted approximately one week. 

The entire situation started when I expanded where I was going to socialize, or try to. If it sounds as if I was doing quite a bit of drinking during this period of my life, it was because I was. It is important to note I rarely drink alcohol at all now. Back then though I used it as a crutch in numerous ways. When I drank I was braver to go and try to socialize with others. To basically dive into the girls sandbox and see what happened. 

What happened was I found I was accepted into a small group of acquaintances who were socially interesting. Especially the exotic sister of one of the bartenders. She was truly exotic in that she was a dancer as well as being a hair stylist. This was in addition to her being a well tattooed dark haired beauty. To say I was envious is an understatement. She always threatened to work on my hair but I wasn’t sure how that would work back in those days when I was wearing a wig. It turned out it never really mattered. The rest of the group included me (the transgender woman) a lesbian, the bartender and her husband as well as others who drifted in and out. 

How I looked back then.

Very quickly it seemed our little group of acquaintances who gathered in the venue for drinks grew. Included in the group was a big teddy bear of a man who worked in a local lumber yard  and rode a classic Indian motorcycle. He fell in love with the exotic one and they decided to get married at the spur of the moment. Ironically, I think most of the group thought it was the wrong move to make. I know I did.

We all were right because the marriage only lasted one week. After it was over, it turned out my feminine socialization was to take another turn into new territory. I was becoming attracted to a man who was paying some sort of attention to me. It all started when the marriage had dissolved. The poor guy still kept coming into the venue and I thought was treated rather poorly by most of the group. I felt sorry for him and let him know. By knowing both of them the short time I did, I didn’t think the two were a match made in heaven. 

At any rate the group began to go in separate directions but I kept coming in the venue as did he. Surprisingly to me, he chose to sit next to me at the bar and all of the sudden I had the ultimate validation of a novice transgender woman…a man at my side. Especially a bearded one who rode a motorcycle. I always fantasized about how it would be to ride with him but never got the chance. Very quickly he took another job and moved away from the area.  

What did I learn? Even though I was having a difficult time being attracted to male companionship, I proved it wasn’t totally out of the question. Also knowing the lesbian in the group was my introduction into knowing anyone who identified as a cis gay female. 

Most importantly I gained another level of confidence. I found I could socialize with a diverse group of other people.

I had graduated to another level of life on my transgender path and it was looking more and more as if there was no turning back.