My love for dressing in lingerie started when I was 12

[Wesley]

It was a dark and stormy night. . . .well, Ok, the truth goes a little differently.

Although I have a mental snapshot of carrying around a pair of shiny patent leather mary jane shoes as a very young child (probably around 4 or 5) my cross dressing started during the summer of 1971.

I should probably tell everyone that I am 49 (As of Aug 2009, I am 50) years old. I graduated high school in 1977. During the summer of 71 I had just turned 12 and from what I recall, I was just hitting puberty.

IT ALL STARTED

During the summers, I would go off to visit my Grandfather who lived in a small town in western New Mexico. There were two boys my age, that I ran around with. One day, one of the boys and I were in the spare bedroom where I was staying. Somehow, we found a bikini that my mother had purchased for my cousin the year before. Evidently she had left it. It was a typical 1970 style bikini, moderate cut (my cousin was about 16 or 18 at the time) and had a colorful flower pattern.)

We were goofing around and teasing each other and we ended up trying it on. I guess it made more of an impression than I knew, as it seemed I was hooked.

I really don't recall much about that year, but the next year, I "borrowed" a white bra (34B) and panties from my girlfriend. She never knew and as far as I knew, she never suspected either. I don't remember a lot, but I would wear them in a sexual connotation after going to bed. Before long, I borrowed another bra, panties and baby doll nightgown from her.

GETTING CAUGHT

was not a pleasant affair for an 8th grade boy. Even though my mother was a fairly progressive and educated woman (she was a high school teacher) I don't know that she could have understood the ramifications of being confronted. I came home one day to find the cloths on the kitchen table. (It was a good thing that I had no brothers or sisters) And was immediately confronted when she got home a bit later. I was given the third degree about where they came from, but fortunately, she did not ask a lot of questions about what I did with them. My biggest worry was that she would make me "march down there, and return them. Luck was on my side as she didn't do that either.

Temptation got the better of me though and I could not resist the urge to dress in lingerie again. For a short while, I did without, but later hit on an interesting solution. I had a friend who was a bit younger than I, and had a sister that was a year older than I. Since he owed me a favor, I asked him to "borrow" one of his sisters bra's and panties, which he did. This time the bra was a plain white 34A, and was very soft and silky. Taking no chances, I hid these articles somewhere outside of the house.

By the 9th grade I was hooked. I can recall wearing the panties under my jeans to night school one night. That was the first time I had worn anything outside of home. The feelings of trepidation, abject fear and excitement were indescribable. Those feelings would set the tone for probably the rest of my life and I will describe below.

OLDER, BOLDER AND WISER

Around this time, my parents had purchased a house that was being built. and we would go over every few days to see how things were going. It was during this time that I first wore a bra out in public. I decided that since I enjoyed wearing panties under otherwise "normal" clothing, I would try wearing a bra. My first experience with this was on a trip over to the new house. I wore the 34A bra and panties under my boy clothes, and a windbreaker. No one noticed and I once again had the thrill of "Getting away with it."

Like many of my cross dressing bretheren, I started becoming aware of what the girls of my age were wearing and wanted to emulate them, be like them, at least in what they were wearing. Most guys would notice that a girl was cute or had "great knockers." but I would notice what sort of bra they were wearing. . (with everything else in short order.) Of course, like most impetuous boys of that age, when you see something you want, you try to get it and I was no different. I was not quite ready to go purchase these things on my own and asking mom to take me bra shopping just seemed a little out of the question.

Strangely, it was about this time that my parents decided I needed a bit of sex ed as well. Their solution? A copy of Dr. David Ruben's bright yellow "*Everything you always wanted to know about sex but were afraid to ask." Certainly a "Novel" approach to the problem. Ruben didn't really address cross dressing per se, but touched on it. It did help me to realize that it was something that I was not likely to be able to easily change and gave me a leg up on accepting my behavior.

My parents were also starting to respect my privacy more. This was a good thing as the cloths now went into a locked box under the bed. Though I am sure they knew it was there, they did not at any time demand to know what was inside.

So, now the problem of how to expand my "wardrobe" presents itself. Since we lived in the suburb of a large city (Ok, suburb of Oklahoma City) and I had a 10 speed that I rode regularly at night, a solution presented itself in no time.

There were a couple of apartment complexes within a few miles of where I lived. I discovered the laundry room one night. Humm, I thought. . no one is around. . . so, I watched, waited and then went in. Opened a dryer and quickly looked though. I don't recall how long it was before I found something but soon my collection was growing.

I had given some thought to what to do or say if someone came in. Since I was in 10th grade and high school at this point, an excuse was easily formulated. my girlfriend left my class ring in her pants pocket when she stuck it in the laundry. Perfect excuse. . . and the only time I had to use it, it was accepted without question.

In my senior year, I had a girlfriend who was the first that I told about my cross dressing. I guess the social outlook had started to change as she was accepting of it. In fact, she was the first girl to actually buy me a bra! She never had a problem with my wearing panties under my clothing which also helped with my accepting my "uniqueness."

GROWING OLDER GRACEFULLY

in some respects was easy. As you get into adulthood, you start to accept things about yourself and cross dressing was no exception. I soon realized that if you went into a store (this was the early 80's) and purchased lingerie for your wife/girlfriend/lover no one cared. There was no embarrassment. The big hurtle was always doing it the first time. You find yourself second guessing and looking at people in the store. ."will they say something" you ask yourself? After you can work the script in your mind and in reality a few times, it becomes easy.

When you are young and in your 20's, you are thin and buying cloths is easy if only it were always that easy. . .After getting my first credit card, I discovered catalog shopping. This was in the days before the internet and even dial up BBS's were very popular. My choice in lingerie at this time ran to very small cup bra's that I could wear under a shirt and sweater. Avon fashion had a thin cup bra that was perfect.

I married a second time in the 90's when I was in my 30's. Having a wife that accepted the behavior made life much easier. Not only did she accept it, she encouraged my cross dressing. A few weeks before we were married, she had gotten a pair of small and inexpensive silicon breast forms for my birthday. Before that, I had been using foam that had been cut to size and shape.

When we got married in Las Vegas, I was wearing a bra, my first pair of silicon breast forms and panties! A few weeks before we were married, she had gotten a pair of small and inexpensive silicon breast forms for my birthday.


REFLECTIONS

of my life and cross dressing are many and varied. I do not regret putting on a bikini the first time. I enjoy my cross dressing. My wife enjoys my cross dressing and encourages it as well. I have often wondered, what set of factors drove me to dress a second time. . . I would think that the first time would have some amount of excitement for anyone, but WHY does anyone continue to cross dress? I have read extensively about it, but there are no real answers.

In my life, all the girlfriends (save one) have been very accepting of cross dressing. It truly saddens me when I read of an older cross dresser who kept cross dressing from their spouse and were later discovered with disastrous results. It would seem that keeping such a deep secret for so long from you soul mate could only be seen as a deep deception. I am thankful that times have changed, and at least in my case all I have shared with have been understanding and accepting.

I did have one girlfriend who went psycho for other reasons and tried her level best to destroy me. She went to all my friends and family, and promptly told everyone that I cross dressed (and a few lies as well) At the time is seemed like a disaster. I soon realized a valuable truth though. I realized that to those who really loved or cared about me, would accept me as I AM. It was from this event that I gained the courage to tell everyone that I really did cross dress. Out of the friends and family I told, everyone was fine with it. I was not going to let my cross dressing be used to hurt me. If everyone knows, you can't harm me with the truth.

TODAY MY CROSSDRESSING

is almost exclusively "under dressing." That is, I wear a bra with silicon breast forms, panties, and keds or some other not glaringly obviously womans shoe. Keds are good, black mary janes are good. . .In all the time I have dressed this way, I have only once gotten a strange reaction and that was in a book store. I was wearing white keds and some fellow just stopped, mouth agape and stared at my shoes. Never said a word. . just stood there with a stupied look on his face.

From the first time I went into a womans shoe store (with my wife) and asked to try on womens keds, (the salesMAN never said a word, just helped me like any other customer) I have never had a problem buying womens clothing or shoes. I want younger cross dressers to understand that salespeople don't care, its a sale. . thats it. About the only group you might have problems with is young teen age girls in wolf packs at the mall. . .

I have discovered that I can wear an under wire bra with 36B silicon breast forms (Amona Personally style 651) under a bulky shirt and not be noticed. (See them here: http://www.lucys.net/details.asp?sku=651)

Be yourself. . . These days people don't care and if they do, it's THEIR problem not yours. Don't be afraid to cross dress. Life is to short, and in spite of a email forward from my ex wife which said "Lifes short, dance naked" I would rather dance cross dressed.

[CJ]

Hi Wesley,

That was a great post... a well-written exposé. Thanks for taking the time to share your journey with us. When you have a second, perhaps you can pop in to the new members area and introduce yourself to the whole merry ensemble. Welcome to the forum! Enjoy yourself.

Love,
CJ

[DonnaT]

Hi Wesley, to the forum.

[SilverLady(SO)]

Hi, Wesley, and welcome to the Forum . . . and like CJ stated, please wander over to the New Members section and introduce yourself to everyone!

- SL

[Sunshine Girl(SO)]

Hiya Wesley...

I'm glad you have had an easy time with your "softer side". Your comment about keeping sercets is very important. It's the secret that will hurt, not the crossdressing, for sure.

Sunny

[Absaroka]

Thanks Wesley for your story.
I enjoyed reading it a great deal.
Absaroka

[Lori A]

Thanks for the great story of your beginnings, and welcome to the forum. You are right about SA's not caring about the fact that you are buying feminine articles and accessories. You may be in fact buying those things for a wife or SO.

[Carla L]

Wesley,

Thank you for the wonderful post. I loved reading it and thought more about my first time dressing and how I progressed through the years. I just may have to write about it, as you did. Truly wonderful to read.

[Marjory]

Hi Wesley,
Your beginnings are something like mine. Mary Janes first, loafers second and Keds, when I went to school, were in style for men(1950's-60s). My sister has a picture of us wearing similar outfits both wearing whit socks and mary janes taken when I was~3-4. I don't remember this at all. As far as now, I still wear Keds(I'm 65) and never had a look or comment also Keds for men are back so just claim they're mens!! Never stopped wearing keds since 1960. My sister gave me her loafers to wear to a dance in HS one time and again, although obviously women's no one noticed. I have small feet and narrow heel and a salesman actually recommended to me that I buy a women's pair for the fit. I buy my under-things at Nordstrom small bottom large top and always friendly sales people. Bought a pair of Mary Janes yesterday at DSW and the girl said that "I would like them... they are very comfortable". Makes you wonder who's really buying all the women's clothes.
Good luck with your dressing and have fun doing it.

Marjory

[Gwen Lee]

Thanks for sharing your story.

[Leeza]

Wesley wrote

She went to all my friends and family, and promptly told everyone that I cross dressed

Reminded me of when my first wife and I split up. She said that she wasn't going to tell anyone about my crossdressing then went to our favorite hang out and told everyone. I thought that I would be made fun of but instead I got please contact messages from about 4 of the single women there.

Leeza

[Diannna]

Hummm! Reminds me of my second split up. At the time we were married, she accepted the fact of my other self but did not want to be involved. I worked a swing shift at the time and for a few hours after midnight enjoyed my femme self in the spare bedroom. After the split, she had told her family and my sisters. My sisters already knew. One of her brothers came to me and asked if there was any way we could get back together again and said they knew of my crossdressing and it didn't bother them. I was really embarrased and said it had nothing to do with my cd'ing or them knowing. It was that she was too unbearable to live with, that she had changed after 5 years and I no longer could take it. That was that.

[Wesley]

And, here I am in March of 2025. . some 54 years down the line. I am now 65 years old, and retired after having spent 31 years as an RN.

I still underdress, and close friends know about my crossdressing and don't care. I often leave the house with a bra, panties and size 5 forms. The favored footware for some time is now simple ballet flats. I don't think I had mentioned it, but back in 2022 I had a heart attack and ended up with two stents in the LAD.

Crossdressing has just become routine and I underdress to feel normal. There is no big thrill as there was in years past. Realizing I may have another heart attack somewhere, I am now cognizant of possibly passing out and being exposed in the course of CPR, or in an ER. As an RN, I realize that I will be treated the same, and no one will say a word. Still, It is not exactly something I want to share with the world.

I had considered some time back if I was transgender, and rejected that. I prefer to be a guy who wears lingerie under normal cloths. That is it. ..I don't want to assume the mantle of trying to modify my body to be a woman. Sure, it might be nice to have real boobs, but after 65 years, I am certain of what and who I am. And while I know at least one person on this site would disagree with me, I am aware that problems are starting to emerge for many of the former crossdressers who decided to go all out and get a sex change. That is not really a surprise for me as an RN, but to each his own.

No regrets. . .I am free to be a man anytime I want, and also free to wear lingerie. It is still my little secret. And I have at least made an attempt to document my changing feelings as I have aged. I hope my story will help someone.

Lastly, I really bemoan the loss of the Tri-ess chapter in my area. It was certainly nice to have been able to meet other people with the same "interests." I would actually probably call it more of a perverse fetish. I just wish they had not jumped ship massively to embrace transgenderism, but again, to each his own.

That "fetish" migrated from a significant sexual thrill in the early years to something that just allows me to feel normal in midlife and that is all is has ever been. . .save for the eternal quest to find ballet flats that fit, bras that fit, and are both comfortable and retain a certain feel and style. Oh, and the marval of noticing that people don't notice an otherwise normally dressed fellow wearing ballet flats, and having "average sized boobs" instead of ripped muscles. No one cares!

[KimberlyS]

Thanks for the update Wesley. It is always nice to hear how site members are over time. So many leave and we never hear from them again.

Kimberlys - CD