What Got You Started?

Greetings, my dear readers. First I want to express my appreciation for your responses to my blog postings. It is so rewarding to know that there are so many of you that share this common experience with me that we call, loosely, “crossdressing”. Perhaps a better term is “gender fluid.” That pretty much works for me, as we all have a sense of who we are that is much broader than the confining role of the traditional binary male. I can’t imagine going back to being the macho male I once pretended to be (I say “pretended” because that was never who I really was) and wearing those heavy, scratchy underwear. Thinking about this fascinating journey of embracing the inner femme that we know ourselves to be, I started wondering about what got us all started on this journey.



I’ve read a lot of posts on various sites, regarding crossdressing folks like us, and have found there are many starting points. Some have sisters, and got started by exploring their sister’s panty drawer, or closet in search of the perfect skirt or dress. Others went foraging in their mom’s closet and dresser. Others didn’t have a sense of their femme self until later in life and lived, or do live, in fear of discovery by their wives. Others, the most fortunate of all, have a spouse that is totally okay with the feminine side of her husband or significant other, and lives happily in the gender fluid world with him.


So, I have a question for you: what got you started, and at what age? When did you first slip on that luscious pair of panties and know you were hooked – that this was a part of who you are? When did you first try on that first bra, or blouse, or skirt, and know that this was something you just had to do? We all had some starting point that led to where we are now, and I would love to hear your stories. By reading the blogs here at Xdress, surely by now you know you are far from alone in this fascinating world of the gender fluid; you are part of a virtual community here at Xdress.  Tell me your story – I would love to hear it!

Fondest regards,



Started in 3rd grade, had to wear tights in a school play and really liked it.Progressed from there wearing moms clothes. Married now, wife knows and allows me to wear panties most of the time. Want to take it a lot further. I do have my own clothes and want to share my feminine side with wife.

rocquelle August 26, 2018

A common theme tjought certainly not the only one
Is the early onset of fascination with panties (the closest thing to a womans physical womanhood by the way)
Occasionally 50:50 a wife a girl friend will understand and some even participate

Stevie August 24, 2018

As with pretty much everyone here, my fascination started young and in secret. My mother left my father, sisters and I to go start a new family when I was barely school age and I think that led to my having to figure out the societal contrast of “masculine” and “feminine” on my own. My sisters were never particularly “girly” and, with only my single father to take them shopping, their clothes were strictly utilitarian. I’d see pictures in catalogues and be mesmerized by the womanly shapes and textures on the pages but had no way to experiment. Fast forward to my early teens when my mother re-entered my life for a time and I would sneak through her drawers looking for something to try on. Fast forward again to my first girlfriends from whom I would request a pair of panties to keep at my place. While they did serve as a memento of the relationship, they spent more time on me than in my drawer. I would only use the articles for self-gratification at home. I would (as was written also experienced by others) go through periods of guilt/purge and toss everything out only to have to recompile later when the urge overwhelmed me.
When my wife and I first started dating, I threw out a shoebox full of panties. Of course, she saw the box in the trash and discovered my stash. At the time, my decision was to claim they were souvenirs of lovers past and I was purging them for the relationship to start fresh. After months however, I came clean that I used them for gratification and sometimes tried them on. Surprisingly, that admission was better received than the lie I’d tried to cover with. Still, I went panty-less for years – trying on my wife’s panties in secret and stealing her discarded pairs from the trash to squirrel away. Now, partially thanks to XDress and partially due to our in-depth personal discussions about the nature of masculine/feminine gender roles, she is accepting and complimentary about my desire to wear a myriad of underwear. I have my everyday pairs, then I have my “sexytime” pairs for intimate encounters. I still wear boxer briefs mixed in depending on my activities but all told, my wardrobe runs the gamut from prim and proper to downright scandalous and I love the contrast.
Longwinded I know but I appreciate the platform to divulge my never-before-discussed activities even if only to myself. Thank you XDress and thank you Angie.

Dave August 24, 2018

I started experimenting with women’s clothing when I was 6 years old. I would sneak into my mothers bedroom and try on her bra and girdle and would wonder what caused me to desire wearing her undies. I was very confused but wanted to continue trying on any feminine piece of clothing I could find. Naturally through the years much was suppressed but there was something that excited me about panties and bras and the desire to wear them when ever I had a chance. In my early twenties i started purchasing my own panties, bras, and nighties, this progressed into dresses, shoes, wigs and makeup. I would have the guilt complex and purge everything, then I would start over again when I had the urge to dress up, many dollars went in the trash do to the guilt complex and purging. Fast forward to marriage and raising a family, I suppressed everything as much as I could but had some panties and nighties I kept in the attic for some dress up time when I was alone. Divorce took a toll on me and I lived alone for 10 years dressing more and more accumulating a beautiful wardrobe of dresses, bras, panties, shoes, makeup, and nighties. Enter my new girl friend who I fell in love with. I went to a transformation salon and had a makeover and photo shoot, while i was being made up the woman asked if my girlfriend knew and I replied no. She asked if I am going to tell her and i replied I am scared to, well she convinced me to open up and tell her, and now the rest is history! My new wife has taken me shopping and bought my nighties, panties dresses, skirts, tops,shoes,and nail polish. We even went to MAC and had them find the right foundation for my skin. I now wear panties everyday and go to bed every night in a nightie! I have my own dresser filled with panties, bras, jewelry, and stockings! Going for manis and pedis together is so much fun, I love the pampering. I am now guilt free, and happier than ever.

Kerstin August 23, 2018

Great story
Must have been lots of fun and then to have acceptance
Great for you that your wife participates

Stevie August 23, 2018
First off, I chose my femme name from a high school classmate who was tall for a girl & slim like me. I always complimented her on how well she dressed. Madelyn dressed with such feminine class & style, & I would always compliment her on how well she dressed, but deep down inside I wished I was dressed like her. How did it all start? I lived in a double block home in a small village in northeast PA. I had two older cousin living next door who were 6 & 8 years older than I. Both their parents worked so they were home alone. During the summer months, on rainy days, back in the early to mid 60’s, the radio & 45 rpm’s were the entertainment of the day. I would be with them listening to music & they would teach me to dance. I was 11/12 at the time. The younger one always had aspirations to be a cosmetologist. I had somewhat longer hair for a boy back then that could manufacture a short ponytail. Younger cousin began playing/styling my hair in girlish styles. next came the make-up. Things progressed to being dressed in the younger’s dresses, skirts, blouses, since she was slim & time like me & I fit her clothes perfectly. On the second or third occasions the older cousin stated that if they were going to dress me as a girl, I also had to wear girl underwear. OMG, those first nylons panties were pure heaven. I was immediately hooked. A bra & slip were all part of dressing as well. This would last most of the afternoon till it was time for their parents to begin returning from work. These, oh so special dress-up times for me, lasted two summer vacations from school. Then they graduated & began working & higher education & sadly came to an end. My younger cousin did gives me some panties. I do believe she knew how excited the made me. Well, time marched on & I did continue the joy & excitement of lingerie. Then, WHAM, the internet. Chatrooms, Meetup groups, chatting with other gurls, dressing with others & eventually going out in public. I have a modest wardrobe at present. When I do shop I oft time wonder, ‘Would Madelyn purchase this?’ I am married, my wife & I play in lingerie in the bedroom but I don’t see it going beyond that since we are in our mid-60’s. But I am pleased that my wife has accepted this feminine side of me & enjoys it as much. Sadly, I never did stop to thank my cousins for introducing me to my feminine side & the joys of xdressing. Perhaps some day I will. Thank you Angie for allowing me to tell, “How I got Started”.
Michael (Madelyn) August 22, 2018

I started young, saw lingerie in magazines, then started taking mom’s and sisters things to play and wear. I hid things under my bed and at night would wear them and started my self love (masturbate) history. I still wear and play in the bedroom by myself all things lingerie, I should add I am married and straight but my love for lingerie and feeling sexy carry on.

Dean August 22, 2018

Started in my early 40’s by trying on now ex wife bras and panties hope start cross dressing when I goi out

Terry August 22, 2018

read your replies
One of the things I think we xdressers often fail to relay to others is that dressing is also FUN!

Stevie August 22, 2018

I have worn panties almost my entire life. I am one of the older guys here. There are probably four milestones in my crossdressing life. The first was probably 10 or 11ish when the high school girl that took care of my sister and I used to dress me as a twin to my sister and take us for walks. My sister was older and we were close to the same size. It only happened a few times and I always pretended to not want to but the truth is even back then I loved it. The second milestone was around 13 I guess. I started wearing my sisters panties Then I tried the bras. OMG I loved them both. I immediately became a pantyboy. Throughout school and as a young adult I wore panties as often as I could. The older I got the more I wore them. The third milestone occurred after I was married. I was wearing mens nylon undies as I never thought my wife would understand or accept. They were pricey. One day she surprised me by recommending some women’s nylon panties that were on sale. She didn’t have to encourage me. That day I became a full time pantyboy and have never looked back. I like bras but do not wear them as she would never accept that. I do now and then wear camis (plain), and other women’s things that can pass as unisex. The fourth was around 20 years ago when I entered the Internet age. Like so many others I looked for other guys wearing panties. OMG, we are so many I realized. How wonderful. My sexuality really came into focus (something I had suppressed). I liked what I saw and a lot. I was alone looking at these men but somewhat embarrassed. Things were quite excited in my panties. I liked looking at others this way. Today I admit to being very bi with a preference to feminine looking men. Oh well my story and a long time to figure things out I guess.

Thank you XDress for making it easier for others today. I am all for men being able to enjoy their feminine side in whatever form it takes.

Keri (Scottsdale) August 22, 2018

I first started when I was about 13. I found my oldest sister’s girdle and bra in the hamper and wonder what it would feel like! I have two older sisters and no brothers. It felt so sexy! Naturally I stuffed the bra with socks!. So after that anytime everybody was out of the house I would rummage through her drawers and try on all of it! Including the slips! I do not have a desire to become a transgender but love dressing up in the underwear! About 14 I even got dressed in the bra and girdle and put on her terry robe and out a towel around my head and answered the front door to pay the paperboy! I was so nervous and excited when I handed him the money! I even tried her dress on and it was exciting! Now almost every day I wear my panties from xDress and love them! I have also bought a bra and wig from you and look forward to expanding my collection and hope fully go out dressed as a woman!

GTW August 22, 2018

I got started wearing girly clothes years ago now I have more girly clothes then male clothes as I write this I in a white bra and pink panties. I am clean shaven all over and when I out working I wear my panties and bra under my male clothes. I have a lady that own a store who helps me pick out sexy clothes to wear. For that I help her at her place where I was dress in a sexy maid outfit. The other ladies love me and I even had one that wanted to take me home to clean her place. My lady friend said to go and do that for her, so I did.

fmg August 21, 2018

well for me it actually started with shoes
I saw a pair of peep toe pumps on a woman and wanted to emulate it because it turned me on. I was 8.
I progressed from that to stockings then panties then bras
this continued until college then I would only do it at home when I came home for breaks
then the stress of life (married 30s children) I restarted found the internet and said to myself lets go all the way to full dressing to try to pass
I was terrible at it but after much introspection have accepted my love of lingerie and the look of mixing genders male and female
soft lingerie and the male form
I have no desire to transition but now accept that I am fluid loving to mix the 2 genders
I love my heels and nail polish panties and bras
I wear femme jeans and panties everyday

stevie August 20, 2018

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