Progression of Dressing

Ladies,

How has your dressing progressed over the years? How have life events influenced, did it make you dress more or less, or try new things? Was it your choice? Do you have a line (for yourself not put on by a S/O) of how far you go?

I started pretty young as many of us did. I really liked undergarments and skirts, but tried on whatever I could. In middle school while my brother and parents were off for a sporting event I?d get dressed and do my homework. In college I kept it secret from most, and was able to do more exploration. After college I had a gf that was kind of ok with some things, but I wanted to go further and she didnt. Next gf knew about it all and would encourage me to be me. After college I got much more into leggings and skirts. I?m not sure whats next, I?m free to wear whatever and I have an open mind. Whether just underdressing or going 100% its all positive, glad to be in a community of like minded people!

Kinda a similar start. I felt attracted to dressing and being a girl from early childhood. Learned quickly that it was unacceptable conduct and largely repressed the desire into puberty. In my first marriage underdressing was tolerated, even encouraged. In my second marriage the tolerance was present but my interest expanded exponentially. Full presentation as a woman proved to be a bridge too far and the marriage ended.

Now I live a majority of my life presenting as female and I love it!

I wonder what things would have been like if from the start my wife was supportive and I could have explored everything early on to learn about myself and what I wanted. Instead it probably looks like a "progression" mainly because for a long time I was very limited in the space I had to secretly store clothing and it has taken time and courage to acquire new types of feminine clothing. In a way it is my wife's easing of what she tolerates that has led to a progression to nail polish which I've posted a lot about this past year. Otherwise I would have done that long ago...well at least after kids moved out of the house. Which of course is the next major event that enabled me to dress more. So yes, life events played a big part in my progression because my DADT and family situation really limited what I could do, and still limits me today.

Hi Well in order of your questions it went from zero to pretty much being a full time feminized housewife, influenced entirely by my gorgeous wife, dressed 24/7 along with learning feminine traits, not at all my choice.As regards boundaries I do not wish to be seen in public but feel at some point this is inevitable.

As a youngster (12-15) when home alone, which was rare, I would try my mom's bras and girdles on. I believe it was normal childhood curiosity rather than an overt desire to cross dress. About 3 1/2 years ago at age 71, after complaining about something, my wife told me to "put your big girl panties on and deal with it." Within 3 or 4 days, I bought 2 pair of panties. within a month I was buying other brands and styles of panties until I found what I like (lace hipster panties) and what fit good. I started undressing every day and discarded all my male underwear. then I started to buy thigh high nylons, then nighties, then bras and forms, and finally outer clothing - primarily dresses. I now have 10 lace bralettes, 12 bras, 12 dresses, 8 nighties, 2 pairs of jeans, 3 tops, lipstick, 2 wigs, 3 sets of forms DD, DD, & F cup sizes), a purse, shoes, sandals, jewelry, nail polish, and other makeup. At home I am dressed at least 50% of the time. While my wife is accepting, she is neither encouraging or supportive. While she has seen me fully dressed, she prefers me not to have makeup/lipstick on or a wig. I generally wait until she goes to bed to add those things to what I have on. I've slept every night since 1/1/22 with a bra, forms, and a nightie on. Most nights I also have thigh highs and some bracelets on when I go to bed. Her line in the sand is I don't go dressed where anyone we know will see me and recognize me. I can live with that as I'm really not ready to come out of the closet to those people. I have one friend who knows as she questioned how my wife liked the dress she saw me buying one day. I told her I couldn't lie to her and the dress was for me and not for my wife. She's been extremely supportive and someone I can talk openly with about my CDing.

In the final analysis, I've progressed rather quickly in my CDing life. I've been out in public on at least 10 occasions. I've checked into several motels while dressed. I wear one of my bralettes and A/B inserts on days that require a windbreaker of jacket in cooler weather. I also wear thigh highs 95% of the time I wear long slacks. I go to all my doc appointments wearing lace panties and more often than not I wear a lace bralette and the A/B inserts. At home, I generally change to my femme clothing about 8 pm, then change to my nightie for bed. In the morning, I generally change to drab between 9 and 10 a.m. There are days 11 a.m. sees me still dressed.

Amy, I sure wish my wife would feminize me so I wore 24/7. I cannot imagine how wonderful that must be to have such a dominate wife. While I present a definite male persona to all who know me, if she didn't have issues with me being 100% out of the closet (and made me her housewife), I'd be the happiest lady on earth. I am quite submissive at heart and enjoy being told what to do. Again, I don't feel as though I can present that side of me to friends and family. It would SHOCK them.

As I am about a Month from my 81ST Birthday I have slowed down quite a Bit.

My line in the sand is an agreement with my wife ... no implants or hormones.
Beyond that I have no line to think about.

I am a child of the 1950's and 1960's when there was a line drawn in the sand by society. My parents would be classified as homophobic. Society seemed to equate cross dressing as a homosexual act. That caused a lot of confusion for me; how could a male teenager who lusted after Annette Funicello be a homosexual? Very confusing. Hate from my parents and from the pulpit. I was destined to go to hell. I dabbled in my mother's lingerie draw and slowly outgrew her clothing which sort of squashed any opportunity to wear women's clothing. There was a period of time when wearing women's clothing waned.

After I married a wonderful women my love for nylon was rekindled. There was some "bedroom play" with mutual benefits. Slowly my interests expanded which ended up with "The Talk." My wife is not supportive but does not bring up the subject. I honor her position. Me? When I have the opportunity and the inclination it will be dress, hosiery and heels and all the proper undergarments. I have gone out for drives and strolls. I would not feel comfortable interacting with the general public although I would be interested in attending a local supportive group.

Progressed? Absolutely. Desire to dress? Ebbs and flows, pink fog. Always interested in trying new things. Still am. Line? No. Wife totally supportive, helpful, and accepting. Since retirement, always dressed underneath and most days skirt, top, shorts, etc. I?ve progressed as far as one can. It?s great.

Starting in my early teens dressing in secrecy then sneaking my wifes clothes for many years finally 10 years ago I purchased my own clothing, wig, makeup and started dressing in public during business trips. Now im retired and my dressing has slowed down a bit I need to have the talk with my wife hopefully the line she draws in the sand will let me dress more frequently.

For myself like many here it started early in life. Mom's nylons, sister's ballet outfits. My Grandmother would let me wear knee highs when visiting. With my wife it started with a her swimsuit. 15 years later we are in the bathroom doing each others makeup in heels and dresses. Have been out clubbing together all dolled up. From here I have no idea where it will lead. I am not one that desires to fully cross over being a fully time woman as I like my boy side and those adventures just as much as my gurl, well maybe a little bit more of the gurl side than boy....lol.

But I am happy with a wonderful supportive wife and I feel so truly blessed and lucky. I want to help anyone out there that is on this journey any way I can. Like the one here that asked me for some laundry tips. That was fun.

Still inching along after coming out 2 yrs ago after a lifetime of closet.
Able to do things now my wife initially had not supported so not sure where it will stop. Enjoyable but scary, bumpy ride. We?re doing our best I think.

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Originally Posted by Stephanie47

.....Annette Funicello......

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Not sure what else you wrote. I blame it all on her.

I started wearing pantyhose when I was 18, shortly after getting my first apartment. Pantyhose were the only article of women's clothing that I was ever interested in but years later (2 decades actually) I suddenly felt like exploring further.

I jumped in head first and went all out - dresses, skirts, high heels, lingerie, etc. I even bought a wedding gown with a matching veil. Strangely enough I seldom feel the urge to dress now... maybe once a year.

So my progression is now a regression. Honestly, I'm completely satisfied with just wearing pantyhose every day.

Mom always told me I was supposed to have been born a girl, a lot. And at 7, after the birth of my sister, I started going into my mothers walk in closet, when she and dad were away (we had a sitter) and I would try on her lingerie, nighties and dresses. This continued in secret through high school and into college. After college and marriage it subsided a bit but came back about 5 years later. When my wife went to work on weekends, I would spend all day dressed enfemme borrowing her clothing.

Over the years it just faded away and I didn’t think about dressing for a decade or two. Then I was diagnosed with a pituitary tumor, a prolactinoma, and upon successfully treatment my crossdressing came back with a vengeance. Like crazy full out dressing. Taught myself makeup and started a buying spree, going out in public dresses, that has lasted over 20 years now.

I thought there were some lines I wouldn’t cross but then I started experimenting with breast growth and now have a permanent set of 36DD breasts. Apparently there’s no line there because I have not stopped working on their growth. I’m still working on modifying my body to be more feminine. So I don’t know if I have any real lines except full transition, I think?

I began dressing at 50. Now, at 80 I'm hitting my stride!:devil:

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Originally Posted by CarlaWestin

.....Annette Funicello...... Not sure what else you wrote. I blame it all on her.

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Annette Funicello was the girl whom I suspect inspired my lifelong appreciation for brown-eyed brunettes of which my wife is the most beautiful. From the Mickey Mouse Club to the beach movies I totally crushed on her.

I also started Dressing wearing my mother's clothes. in college I rarely had the chance but after college I lived in NYC and really got to do a lot of things. I was clumsy and just didn't have all the access that we do now. I got Married and my wife knew all about my crossdressing. She was understanding but was not interested in Participating. Then I had my Kids and I stopped for a long while. Now with my wife's suggestion I am starting up again. I won't go as far as hormones or surgery, but I am on a whole health Kick to lose weight.

Like many of us, I started by wearing my mothers or sisters panties as a young teenager and eventually added bras and slips when the opportunities were there. In college, I managed to acquire some panties and pantyhose but that was about it until I was out on my own in my own apartment. After a few years, I had a lingering collection that could fill a duffel bag. That disappeared after I found my conservative wife. Since then, I have built up small collections of underwear and clothing only to purge them from time to time as we have had to move a few times. Now, being retired, my collection is significantly reduced as well as my time alone to enjoy myself. But it is still all good.

My progression was a bit different than most. As a child or teen, the idea never even crossed my mind to don women's clothing, much less my mom's. I was 28 years old when I jokingly put on my new wife's nightgown. I said I didn't like it at the time, but the truth was I liked it a lot! This led to a few private skirmishes with her pantyhose in the early years of our marriage, then a drought of about 30 years or more.
Finally, at age 69 with my wife out of town for a few days I decided to revisit my old interest and bought a few items of my own - and I was off. My femme alter ego emerged almost immediately, and now more than two years later remains a very satisfying work in progress.

For me, it was a cycle of curiosity -- discovery/thrill -- what's next? From youth through middle age it was pantyhose, then I wondered about dresses, then under garments. About the time I got to realize that, I joined the forum and became curious about what I would look like as a woman. It took ten more years to realize that. At the current time, I am just enjoying the ride and meeting up with other CD'rs.

I displayed the same pattern as most others here. Started very young with mainly nail polish and pantyhose, mom's slips and bras. First wife was accepting before and in early marriage then turned on me so I had to go underground. We later divorced and I found out she had lesbian experiences in high school, go figure. Tried marriage again and this resulted in a major purge and another divorce as she was after all my retirement accounts. Dodged that bullet. Rebuilt wardrobe and went deep into dressing, dressing most weekend and spending 3 day long weekends off visiting a trans-friend completely as female. Then met a wonderful sweetheart from Brazil and went started down the marriage path with getting her K1 visa and her coming to the states. Purge again. This didn't work out as the move to another country and leaving her family behind was just too much for her. So now, rebuilding wardrobe once again, quickly this time and spending all days dressed (now working remotely from home) and planning to spend extended time as female. Trips to San Diego, Alaska cruises and getting there by flying pretty. Do I want to physically transition? No, at least I don't think so but I could see living my life basically as a female. It is fun :)

For me I started when I was about 15. House sitting for the neighbors, I dressed up and it was amazing! I acquired some clothes, and began once in awhile putting on makeup. I was always tall and slender. When I went to college as an athlete, my body changed and I became extremely muscular. So I moved away from dressing up. But there was always a girl inside me. Now, years later I am slowly beginning to let her out. Panties, leggings, makeup ( once in awhile). I want to start sharing this side of my life a little. I worry that others will not accept me because I am still very muscular and tall.

Started exploring with my mom’s clothes and shoes at 11-12 yrs old. That went on for 3-4 yrs. Went totally forgot from 16 until probably 24. Came back in my 2nd year of first marriage. I didn’t understand at all at that time. Marriage ended without kids at 30. During this phase only dreamed of CDing. New marriage at 33, told her before marriage, started a small wardrobe, manly high heels. She was a little bit tolerant, not enthusiastic about it. Marriage lasted 10 years.

At 45 I did hit the jackpot! Told her at the very beginning of our relationship and she became a huge supporter. She loves me to crossdress. Builded a large wardrobe where she gave most of it. Where will that lead to? I don’t know, but she made it clear she would support a full transition if I feel that’s what I want.

I've generally been pretty conservative with my dressing and even lingerie.

Recently, I felt the need to shake it up a bit and started looking for ways to expand my presentation and "Pink" came along. Thing is, it's trending to frills and I'm not sure I'm comfy there. I'm a straight guy, no interest in men or transition, but I now have a Pink bunny outfit, and maid's outfit and while they're great, I DO wonder where the hell this is going.

SJ

Started by wearing bras that were not my own.

Fast forward 15 years - started buying bras. Didn't buy anything else because I was in denial about being a crossdresser. Then I saw a camisole and panty set that was lovely and bought it. After that - really couldn't deny that I was a crossdresser. But self-acceptance only came when I found this group.

Like so many here, I started down the CD rabbit hole in my early teens when I found my mother’s girdle and stockings in her dresser drawer. I slipped them on and my life changed. I progressed to my sister’s bras, panties and dresses and soon was wearing her hose and heels as well. When I married, I put my femme leanings in the closet, only to indulge in them when my wife was out of town.
When I retired, they came roaring back, and I fully dressed once a week when my wife volunteered at a local nonprofit. It was about this time that I found this forum and all of you wonderful sisters. When Covid hit, she stopped her volunteer work and I underdressed in her bras and panties. Upon her finding me in them, she suggested I get some of my own, which I have been wearing ever since. I recently added leggings to my wardrobe, and now feel complete. Although my wife is not fully on board with my dressing, we have reached a happy compromise which we both feel comfortable with.

Like most here, these feelings have been around since childhood. Growing up I has a large female presence in my house so there was a lot to get into and experiment with. Throughout most of my adulthood, I was able to suppress those feelings, most of the time. Although every once in a while, I would give in to them and explore a bit. Then, I hit 50 and those feelings started coming back, slowly at first. By my mid 50's I nearly went crazy trying to ignore the woman trapped inside me. I eventually let her out and she completely took over. And here we are ... I probably consider myself more gender fluid or gender non-conforming than CD ... but I am still trying to figure it out. My wife knows and is tolerant, at best, with the whole thing. We tried to set some boundaries but she has no idea what her limits are and I don't want to find out. She did tell me if I decided to transition, she is out.

For myself it started early sharing room with my slob sister but was mostly enjoyed pantyhose and slips and rarely skirts. In my teens it was buy pantyhose and then feel guilt and throw them out just to buy another pair a few days later. Once married I thought I was finally free of it but 2 weeks later one morning she left for work early and there were pantyhose and slips everywhere I put on a pair of her pantyhose and realized how serious and real these feelings were and not wanting to live as a fugitive the rest of my life I came clean to her that same night. I told her everything from the first time I remembered putting on my sisters pantyhose to that same morning I put on hers. Surprisingly she was ok with it and just wanted to see where it was going and we drew some lines in the sand and then she didn't want me wearing her things so we went out and bought some fem stuff for me. Surprisingly enough I was only into pantyhose and slips but my wife bought me a bra and panties set, and she introduced me to that herself. My biggest progress was when I joined here, I never considered make-up or jewelry and even wigs. I would go for drives half dressed and then speaking and listening to people here I started putting on makeup and I bought a wig and finally breast forms. This site completed me and gave me confidence and now I can't even consider half dressing, it's all or nothing. Having a supportive wife does help, I have crossed the original line in the sand but I'm still keeping to my promises that kind of keep us both happy. I believe it was this site that really gave me the big push and expecting I will never pass as a women I'm content to where I am now but always looking for new thrills.

My progression was secret dressing lingerie from very early years to my 60?s. After finally having the talk with somewhat accepting wife, now have a small collection variety of fem clothes, and very limited use of makeup and wigs.
As far as life event influencing the talk decision for some reason I just felt more strongly to dress and felt like I was lying to her by not being honest regardless of possible outcome end of marriage, and yes it was my choice to do so.
My self imposed line in sand is to cd 95% in house and be as discreet as possible when out the other 5%.
How far to go I guess is unknown as I have done more than I ever would have imagined over the past two years.
Right now actually in a 2 month funk of non cd but assuming it will come back based on comments here. Wife likes it this way and part of me does too but also miss my cd life. As I tell her - it?s complicated.

Wow. the stories here are so similar. I started wearing my mothers tights, which today probably would be called leggings, when I was 11 or 12. I'm 69 now so i'm talking the 1960's when this was definitely frowned upon. I stopped for a number of years because of the societal pressures if everyone found out. I began running just as running tights were starting. I was in heaven and for the first time I could appear in public wearing tights. All the time I yearned for something more as I fantasized about dressing fully. But marriage and children interceded so I just stuck to my running apparel. After we divorced and I was living alone I began my journey anew. I began using makeup and the first time I went out, only to get gas, I looked horrible lol. But I loved it. As I progressed I knew I would need some professional advice so I went for my first makeover. When I saw myself something clicked, "wow I really look like a woman" Fast forward I continued my dressing and makeup going out quite regularly. When I met my current wife I told her on our first date. She understood and to this day is somewhat supportive but would rather not participate and does not want the neighbors to know. I continue to go out regularly and wish it could be more. But we all have to make compromises.

The desire to dress up has been in me since I can remember.
Over the years I tried to hold back, until.
Two years ago I dressed up from head to toe and showed myself in public, first shyly, then quite openly, when it occurred to me that no one was paying attention to me.
In a short time I realized all my fantasies, among which shopping was the least complicated matter.
Going out in a dress to the theater or even in an evening outfit to the opera - was not a problem.
Favorable circumstances came and it came to the point where I could spend not hours or a day but weeks in a woman's disguise.
And then I felt the weariness of it all, I began to long to return to my own ordinary life.
Now I still like to dress up from time to time, but it is definitely less frequent.
I also stopped getting tired of the most varied fantasies, probably everything I could think of in terms of dressing up - I realized.
At most, sometimes, when I see some nice dress, I will enter the fitting room with it. But it has become a regular thing, one more, maybe 20 or 50 dresses put on.
I certainly know that I do not want to be a woman, that my inclination is fetishistic in nature.
I enjoy dressing up, but if it were to jeopardize my relationship with my wife or children - I think the pleasure of dressing up is not worth it one bit.

hello Pantyfan,
Progression is quite normal as we test boundaries and lose our inhibitions.
before I was 10 years old I was attracted to wearing tights. Tonight I am wearing a dress and breast forms in private too! I like the clothes but have no desire to present as female in public, so that is my natural limitation.
luv J

My first experience was in the 2nd grade. When mom went out I go thru her pantyhose drawer, open an egg, and try on her pantyhose. I just loved the feeling on the nylons on my legs. Then I saw her gogo boots, that fit me. It felt soo wonderful.. now I'm 55 and I dress completely from toe to neck. I don't do makeup or wigs, and I don't go out.. my roommate who used to be my gf was ok with it in the beginning, but later she changed and didn't like it.. now she lives in my home as a roommate and when she out it's dress up time for me... I still sooo much love the feeling of nylons on my legs, satin bra and panties, and I have a few pairs of boots and high heels.. would be so nice to have a woman who was ok with it, would be nice to share my entire life with someone..
Did I get off the subject?? I hope not..

About 25 years ago I had a job that took me away from home for a week 3 or 4 times a year, I used to take a pair of my wife?s stockings and a pair of her undies with me, it made me feel close to her and I loved wearing them under my suit, fast forward to today and I have just bought a fur which I have always had a fascination for and hopefully by Thursday night I?ll have my knee high suede boots, my wife is a work in progress with this just as I am, I haven?t worked out where my line is yet, but I know id love to go out somewhere safe wearing my fur and boots, but being in Melbourne Australia there doesn?t seem to be a lot of information on where to go, where to buy things, id love to hear from some Melbourne ladies and get some tips, id also love to get some advice on how to expand my wardrobe and learn what my fashion is

Mine started as a young boy, three or four years of age. I would wear my mother's Merry Widow which was stored in my room. When I was older I'd borrow my sisters lingerie and dresses. Now I have a supportive wife and can go out dressed whenever I choose.