Hello There,
I'm back again with another decade of vintage stories and photos of crossdresser, transgender, and gender fluid women, this time from the 1980s! I'll be formatting this post similarly to my posts from other decades with three fun stories from our feminine past. The 80s were all about big hair and extreme fashion! Although the 1980s saw the rise of conservatism in both the US and UK, there was no changing the fact that gender nonconformists were still going to be active out in the world!
Of course I have to start off my 80s spotlight with some pictures of actual 1980s crossdressers and drag artists! It's interesting to see how the fashion and hair styling has evolved from the 70s.
Now that you've seen some examples of crossdressers from the 80s, like last time I've got three different examples of crossdressing in the 1980s! I've chosen these stories because of how they transcend time and can feel relatable even now. These are actually going to be images and words taken directly from crossdressers from the 80s who published their stories and advice and in various print publications. I haven't edited the content of any of them accept for length, and these are the exact words and pictures published in the 1980s.
Vicki
As with last few times I figured I'll start with a classic story of a young CD starting their journey into femdom. Today we have Vickie's story from 1980, she recounts her early days of dressing, as well as the ultimate getting caught story! You'll just have to read her life story and find out the shocking twist yourself!
One might say that Vicki has had two births during the course of her lifetime. The first being her genetic birth as a male almost 42 years ago, and the second, was the birth “out of the closet” some 36 years later.
Now this is not to say that she waited all this time before realizing what she was. Like a majority of Tv’s, she had an early attraction towards female clothing and especially high heels. This had manifested itself around, age eleven. At first I experimented with my sister’s shoes although she never was aware of this unusual habit of mine. The same can be said concerning my family - no one else apparently knew of my interest in clothing belong to the female members of my family.
That is, with the exception of my mother! During grade school, and high school, for that matter, I was largely an introvert. I still am, I suppose. Anyway, during my school years although I was very interested in the young ladies around me, I apparently was too shy to ask them out. My mother made the remark that perhaps my high-heels were a real substitute for a girl friend. And, I suppose, to a great extent, she was right.
My mother never really objected to my wearing nylon hose and high heels in her presence but she strongly recommended that I NEVER let my father catch me that way.
As we lived in the country we had little to fear from our neighbors nearby, the nearest family lived at least half a mile away. My father held down two jobs -- farming and railroading, which meant that he was gone a great deal of the time. Of course, this gave me lots of opportunities to wear my shoes in rather secure circumstances. Probably the best reason for not allowing my father to know of my “unusual” desire was the fact that he was from the “old school” and just would not understand such things.
...It really didn’t make much difference to me whether I was the only male around that liked articles of women’s clothing or that there might have been thousands like myself. It just never crossed my mind - I just kept enjoying wearing my pretty shoes whenever possible. At times, and rather infrequently, I would try on a slip or bra and possibly some dress or skirt and blouse combination. And I never got involved with cosmetics until some years later when I came out of the closet -- completely!
Upon graduation from high school I was confronted with two choices -- either enlist in the army or be drafted. The former appeared to be more attractive since I could join the air force and get placed where I wanted to be. So I was soon shipped off to basic training in Texas where a private life just didn’t exist for about twelve weeks. It was a shame but I had to leave all those nice pretty shoes at home. But the service kept me very busy and there wasn’t much opportunity to think about any crossdressing.
But once that I was assigned to a more permanent station. I resumed the collecting of pretty shoes. While off-duty, I could wear a pair of nice high heels while driving around the countryside. It was in this area that I remained until my discharge some six years later.
While permanently stationed and before being discharged, I met my wonderful wife to whom I have been married for 21 years. It was shortly after we were married that I informed her that I liked to wear high heeled shoes. But, surprisingly, she was not shocked -- only stunned with amazement. She said that she had never heard of anything like that but if I enjoyed doing it, well, then, I was free to go ahead. So everything went along fine for the next few years. When I would come home from work each evening, I would slip into some nylons and pretty high heeled shoes and perhaps a bathrobe. I just sat around for the evening, watching television.
Two daughters were born to us and the next year, 1963, I was discharged from the service. The position that I had held for awhile had required that I report for work about 4:30 in the morning. Being married, I was allowed to live off base in town -- some 15 miles from the job. The bright idea of slipping on a dress, shoes and a headscarf appealed to me for the purpose of stopping along the way to obtain a newspaper from a corner news-stand. I even went into several 24 hour laundromats to get some change. Naturally I would do these things ONLY if no one was around and at that time in the morning there were few people around.
Well things seemed to be going very well for Vicki at this point. She has a wife who is supporting of her Crossdressing, and Vicki has been able to fully crossdress and go on adventures around town in public. She's living just about every crossdresser's dream. Well it was all going to come crashing down! I told you she had an amazing getting caught story so buckle up this is quite a doozy.
Had I confined myself to a neighborhood area I might have been all right. You see, each time I “got away with it” I got a little more bolder and finally I decided to take a stroll in the down-town area. And for a few mornings it went fine - until that one fateful early morning.
I had just parked the car along a side street with my male clothes in the back seat. This would allow me to change back into my male clothes before getting to work. Anyway, as I was rounding a corner on the almost deserted streets, there was a police car. I was some distance from my car and just plain froze - I couldn’t move! Finally I turned and walked back in the direction I had come from. But, evidently my walking was considerably erratic because the patrol car began following me.
Slowly they eased past me and pulled over to the curb at the next street corner. What could I do but continue walking towards them! There was no place to run and I had already probably given myself away by showing my fright at seeing the patrol car.
One of the officers got out of the car and came towards me. He asked if I was feeling all right and from the tone of his voice he probably thought that I was a woman. The street lighting was rather poor so ‘passing” as a woman was accomplished with little effort under such conditions. BUT, having to stop and SPEAK to someone was an entirely different matter!! The jog was up so instantly I confessed that I was a male at which point I was escorted to the squad car and taken to the station.
Once inside the station, I was interrogated by the officer in charge, who said that about all they could charge me with would be disturbing the peace. But that would have been hard for them to prove as I was not making any kind of scene out on the streets, nor was l bothering anyone and I was certainly not creating any disturbance. The officer did inform me of the one obvious thing I was doing, however. You just don’t see a woman, unescorted on a downtown street at 4:00 in the morning. THAT was my undoing!
After a few minutes they called my superior officer on the base. He eventually came and took me back to the base. From then on it was just a matter of some paperwork until I was discharged.
My commanding officer wanted to give me a general discharge and I had the option of accepting his decision or going for a court martial. I elected to take my chances with the Court and this must have bothered my commanding officer. No doubt it would have been quite an embarrassment to him to go before a military court with a case involving a transvestite. After a few days the commander called me into his office to give me his decision. He had changed his mind and would recommend an honorable discharge under Air Force regulation 39-16. This states that anyone coming under that category was “unfit for military service.” This does not usually carry an honorable discharge with it. Frankly, this was about the best that I could hope for, even with a court martial. I agreed to this as it allowed me the full pay and other benefits afforded anyone who got out under normal circumstances.
The whole ordeal was quite a strain on my wife who stuck by me throughout the whole episode. Fortunately the children were very young and did not know of what was happening. With my service career behind me I decided to move back to my home state and begin a new life as a civilian.
I had been back home a little over a month when the whole thing was exposed to my parents - as to the exact reason for my discharge. Earlier in this story I had mentioned that my father was from the “old school” and did not “take” to this information. But my mother was much more understanding, having known of my crossdressing when I was at home as a child. At first, my father wanted to leave his hometown. He made no effort to listen to any facts about transvestism and, for that matter, I really didn’t know of any such facts to present to him. He did make an appointment for me to see a “shrink", total waste of time, as far as I was concerned. The Doctor knew less about transvestism than me.
Working as a common laborer proved to be getting me no-where so I put my “second self” aside “for the duration.” I attended a trade school for a year and landed a good paying job that I have held for the last fifteen years.
By this time my daughter was getting old enough to go to school and we thought it best to shelter her, and the other children, was seeing me in any kind of women’s attire. Looking back, it would be hard to tell if this was the right thing to do but it seemed best at that time -- especially since we lived in a small town. For several years I didn’t even wear my shoes in front of my wife. So she thought that I had “gotten over” my need to crossdress. I’m sure that most of us realize that this just does not happen to a real transvestite.
In late 1974 I was looking over some magazines in a book store. I had noticed some magazines that dealt with female impersonation and I eagerly purchased several. Inside were stories and articles as well as photos about how men transformed themselves into “females” and that whole conception of impersonation completely captured me. There were even advertisements dealing with books on make-up and accompanying instructions. I even sent away for several of these books on “how to” to see what they were like. When the books arrived I used them to help me to completely learn how to use make-up. I started taking photographs of myself after I learned about how to makeup my face, although they were initially taken in black-and-white film. But this gradually gave way to color film. I felt that I was doing a fairly good job of looking “for real.”
After six months of working with makeup, clothes and wigs, I felt that I was ready for the BIG STEP - appearing in public. This called for traveling some distance to a large town where there would be little chance of meeting anyone that I might know.
Talk about being nervous! I certainly was in a dither when I left the motel room. I had forgotten to use my perfume and almost overlooked my nail-polish. As I left the room in the early evening I met two young boys on the stairway. Trying to act as cool as possible, I casually walked past them as if I had done this hundreds of times before, As we passed each other, they continued to talk among themselves and paid absolutely NO attention to me. It was a relief that the first hurdle was over with!
Within a few minutes I was in the midst of all sorts of people at a crowded shopping center. No one paid any attention to me so I guess that I was doing everything all right. The large store windows made good mirrors to see who was passing by me and I would pretend to be looking at some merchandise in the window display. It gave me an opportunity to observe whether any heads were turning in my direction. Oh, a few did, for an instant, and then they would continue on their way. Finally I got bold enough to stroll through a brightly-lit store where I could just be another shopper looking over the pretty clothes. Again, most everyone was so pre-occupied that they reallv never noticed me. After an hour of this I thought it best to return to my motel room where my wife was waiting for a full report. She was much to frightened to accompany me on my adventure. Thus I had to go by myself this first time.
Generally, I enjoy shopping for wigs, clothes and especially high heeled shoes. I also feel more comfortable being dressed while shopping for cosmetics. Dining in restaurants while doing my “second self” is a favorite activity. It doesn’t bother me at all, now, to give my order to a waitress. I have even passed people that I know who didn’t give me a second glance.
Vicki has come a long way in the past few years since she emerged from the closet. Having done the many things that females take for granted has proved to me quite satisfying. I am no longer up-tight about having to “prove” my femmeself. The novelty of “passing” has given way to simply just enjoying being a girl.
At the same time, I continue to expand my shoe collection which comprises the largest part of my wardrobe. I have more money tied up in pretty shoes than all other articles of clothing. A conservative estimate would be an average purchase of a pretty pair of high heels every two weeks. At this time, I have over 500 pair of shoes. Small wonder that I hardly wear any shoes for more than a few times. Since I can wear an 8 or 8 1/2 in a woman’s size, I am able to take advantage of the many shoe sales in my home town.
An interesting experience occurred to me recently which bears telling. I was shopping in a large mall when I noticed a cute pair of 4 inch heels, black ankle-strap sandals, and I asked the salesgirl if they were available in size 8 She said that they were so available and went to get that size for me. Upon her return, and since I was not “dressed” at that time, I asked if I could take them to the back of the store and try them on. I explained, also, that I was a transvestite. She just wasn’t prepared for this type of situation and said that she would have to ask her manager. However, he was evidently more interested in the sale than anything wise and allowed me to do so. So , the three of us, the salesgirl, the manager, and myself, walked to the rear of the store where I calmly slipped off my male shoes AND socks, exposing a foot with painted toenails and nylons. The shoes fit perfect. The manager and the salesgirl looked on with much interest and remarked how nice they looked on me as I took a few steps in them. As I paid for the shoes, I gave the girl a picture of myself while crossdressed.
Things are getting better for transvestite as evidenced by an experience I had in a town about 40 miles from home. I phoned the police dept and asked them about the crossdressing laws, if any, and was told that none existed. Needless to say, I was most happy to be able to go to a city and be Vicki and not have to worry. Without having to be concerned with laws prohibiting crossdressing, I can concentrate more on being Vicki.
I’m always ready for an outing as Vicki but, like many women, have difficulty deciding which dress or wig to wear. I hope that more sisters will have only that type of a problem to be concerned with as they get ready to go out on the town.
What a shocking twist! Actually being arrested and discharged from the military for publicly crossdressing! But it sounds like things worked out for Vicki in the end. She still has her supportive wife, is able to walk freely in town without fears of being arrested and has 500 pairs of shoes! What a massive collection! In dedication to Vicki's love of heels, I've added some photos of store catalogues from the 1980s featuring high heels.
"Like Father like Son"? More like "Like Mother like Daughter"
My next story to share today comes from Joanne Wilson, who was an Australian writer of several serialized fictional crossdressing stories for various magazines. However the story I'm sharing with you today is not fiction however, and is actually a recounting of Joanne's own life. It features a humorous coincidence between father and son.
(My crossdressing started when) I was just five years old as a result of a good natured whim on the part of an aunt whom I used to stay with regularly while her husband was away at the war (WII). She had a neighbor who had a daughter my age who had been born deaf and 'who was struggling to learn to speak at a special school. My aunt figured Kerry-Ann, who was also a very shy and nervous girl, would maybe respond more positively to a girl friend than to a boy and so one visit she dressed me as a little girl (with things she had bought specially) and I was introduced to Kerry-Ann. My aunt was right. After a period of reserve, Kerry-Ann became my friend and I was indeed, over a period of time, able to help her to learn to speak.
On almost every visit to my Aunt’s place over a period of three years I was dressed as a girl and Kerry Ann and I would play together. At first I had no objection to being a girl; I was young enough to be ambivalent about it. But as I grew up a little I actually came to enjoy it.
When my Aunt received word that her husband had been killed over Europe (he was a bomber pilot) she moved away from the house next door to Kerry-Ann to a part of our state which was too distant for regular visits from me. So the opportunity to dress was removed from me. Neither my Aunt nor myself had ever mentioned to my parents what had taken place over those years at her house, so they never knew. But I longed to be a girl again and soon after began to borrow my mother’s clothes in secret.
All through my early teens, when I was often left at home to look after my much younger brother. I would spend nights alone dressing in my mother’s clothes. So you can imagine the strange combination of shock and relief when I discovered at the age of fourteen that my dad was a cross-dresser as well. I found out by accident. It was just that I came across his cache of clothes while I was searching for something to wear myself. It also soon became plain to me that my mother knew of and even encouraged, his cross-dressing habits. But I was a very shy teenager and I didn’t get on at all well with my father so I was never brave enough to broach the subject with either of them. Often though, I used to lie awake at night (he used to dress after he thought my brother and I were asleep) to try and catch a glimpse of him. I found a way to see him as he passed by our bedroom door and had h\s back to me for some moments as he proceeded down the hallway. It was always very exciting for me to see my father as a tall, elegant, well-dressed woman!
What a coincidence both Father and Son were active crossdressers, it must be genetics LOL. It's a shame Joanne never got the chance to bond with her father over their shared love of women's clothing. Even though Joanne never got the chance to discuss crossdressing with her father, what an interesting feeling of validation Joanne must've felt seeing that not only was she not alone in her desire to dress as a woman, but even her father found the lifestyle enjoyable.
A whole book on how to Crossdress?!
Our last example of crossdressing from the 80's comes from JoAnn Roberts who, in 1986 literally wrote the book on crossdressing. Titled Art and Illusion: a Guide to Crossdressing, the book was a detailed description on how to effectively crossdress. Before the internet provided unlimited knowledge to new crossdressers this book must've been an incredible resource. I thought I'd share some highlights from the book that I found interesting. JoAnn made several lists of what she thought were the essentials of every crossdresser. They are listed below!
Moisturizer
Foundation/beard cover
Dark contour
Highlight color
Eyeliner
Eye shadow
Mascara
Lip liner pencil
Lip color
Translucent powder
Optional products: lip sealer, eye shadow, sealer-lip gloss, iridescent powders, artificial lashes
Panties
Half slips coordinating with the slip color with your outer clothing and making sure it doesn't show!
Stockings
Garter Belts
Pantyhose
Panty Girdles
It's pretty interesting to read those lists and compare my wardrobe and makeup to what Joann recommends. Its seems I might have a few gaps I have to fill! In addition to those helpful lists JoAnn catered some advice to people of particular body types. She first recommends certain types of wig styles depending on the shape of your head (of course these hairstyles may be a little dated 40 years later).
JoAnn also created a list of clothing choices that can be made to compensate for typical physical features of men that aren't exactly feminine.
-Lines in neck or large Adam's apple: wear scarves or high collars
-Long or thick neck: Peter Pan, jewel necklines, hair low on neck, high neckline
-Broad wide shoulders: Unconstructed shirts & jackets, dropped or raglan shoulders, narrow lapels, halter necklines, low necklines
-Heavy arms: Raglan, kimono, Dolman sleeves, very long sleeves without cuffs
-Large bust: Dark colors on top, v-necks, raglan or Dolman sleeves
-Thick waist: Chemise, drop waist dresses, Chanel style jackets, blouson style dresses, narrow belts same color as outfit ( if at all)
-Tummy protrudes: Tunics and chemises, A-line skirts, hard finish fabrics
JoAnn wrapped up her book by saying this: It is all up to you now. As I've said before, practice, practice, practice. Read, observe and copy. Develop your own feminine style. You can do it, if you will only try. With all her helpful advice finished, it was now in the hands of the reader to apply her advice. If you are interested in reading the full book a link can be found here! There's WAY more to read than the few things I listed. JoAnn goes into a lot of detail on how to do makeup, pick clothing sizes, and much much more!!
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Well there it is, another decade done! The 80s were fun to explore, but I won't lie, I'm looking forward to the naughty 90s! But till then I hope you enjoyed all of the examples of gender nonconformity from the 1980s. Vicki's story was certainly quite a rollercoaster wasn't it! My 90s extravaganza will take some time so don't hold your breath waiting for it, I'll get it out as fast as I can! In the meantime I'll leave you with two things firstly another humorous crossdressing comic from the 80s and then me in my most 80s inspired outfit.
-Carly
