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,



For me it started at a younger age like mostly everyone else here. I lived with 2 sisters and my mom for most of my childhood, and although my dad lived with us too, he worked very often. Needless to say I was raised by females. The first time I ever dressed up was around age 8 or 9, a silky blue dress my sister had in a box with a few other clothes she didn’t wear often. I immediately felt excited, and had a strong desire to keep doing it. From then on, I would take every opportunity to wear my sisters clothes whenever they were out of the house. Panties, skirts, dresses, blouses, hosiery, shoes, you name it. I loved the feeling of soft, delicate clothing. For me, it has always been about that feeling, as I never had the desire to be a girl, or wear makeup etc. This continued on through middle and high school. Occasionally dressing up was always a huge relief for me. I always felt like it was wrong, but I couldn’t fight the desire. I got together with my current girlfriend at age 16, and for the first year or so of being together I never would dress up for fear of her finding out. Then I couldn’t repress the urge any longer, and would dress up in her clothes every now and again in secret. Around age 19, I revealed to my girlfriend I enjoyed wearing pantyhose, and explained it as something that was purely exciting to me. She was accepting of this, but that is as far as it went for the next 2 years. I was afraid of revealing that I wasn’t only interested in pantyhose. At age 21, I finally told her everything. This was actually less than a month ago. I plan to marry this woman, and because of websites like this, I had the courage to tell her everything. After all if you marry someone, they should know everything about you. At first she was hesitant, asking the typical questions about whether I’m gay, want to be a woman, etc. After the talk, she told me she is okay with it, but didn’t want to see me in it. However, after about a week she said she was okay with seeing me in those clothes. I now wear panties, pantyhose, and a bra under my work clothes everyday, and fully dress up at least once a week. I started shaving my legs as well, and plan to wax or sugar them in the future. I still feel nervous dressing up in front of her, but that is simply because it is still new. With time, it will only get better. I feel this has brought us closer together, and I am beyond appreciative of websites like this. That not only sell clothes designed to satisfy my needs, but also give a platform to share my experience instead of having to hold it in.

Nathan October 02, 2018

Don, you are so fortunate to have a lady like mine – she’s with your expression of the inner femme, and what a blessing! If she limits you to panties, bra, and camisoles when you go out, you are indeed a fortunate gurl.

Stevie, you touched on something my wife and I do and thoroughly enjoy as girfriends – going to get manicures and pedicures together. We love it. We go to a nail salon that is crossdresser friendly, and they have no problem putting polish on my toenails. (Frost pink is my absolute favorite.) Also, monthly pedicures are great for nail health. One caution – in the winter, it’s best to not wear polish. I got a nail fungus on a big toenail. My nail tech told me that the nails need to be exposed to air when wearing polish, and winter is the time that nail fungus is the biggest problem, due to keeping the feet covered at all times. Thanks to my podiatrist, I got rid of the fungus, but it took 10 months for the medicine to clear it up. Just a word to the wise, one sister to another.

Fond regards,

Angie September 30, 2018

In eighth grade when I was at my aunts house I took one of her black bras and panties. It was one of my earliest feelings of sexual liberation. I didn’t do any other crossdressing until almost 25 years later when I tried my girlfriends underwear on. Since then I have tried more and more but it still has taken me a long time to accept that I am a cross dresser, even if it is only in the bedroom.I still have more to explore but figure this is a lifetime journey.

Sam September 30, 2018

Great story. I too got home early put my moms and sisters clothes on. I too had 4 girls in house
I have expanded my wardrobe
My SO knows but shes not as liberal about my house wear as yours is
I do wear panties and bras sets that i wear under my regular clothes
My SO does tolerate my toes being polished we ve even had pedi together

Stevie September 26, 2018

My sister would dress me in her underwear when I was 6ish. I enjoyed the feeling of her satin panties. She also dressed me in here ballet tutu. As a teen, there were more ladies in the house than men. I would get home early and put their clothes on wearing them until they got home. Later, I would sneak my ex’s panties on. I was divorced and while on my own would buy women’s clothes to wear around my house. Over the last few years I introduced my wife to my love of sexy men’s lingerie. I went slowly pushing the envelope little by little. I can wear anything around the house but when we are out she limits me to bras, panties and camisoles which is okay by me. She loves taking my picture as I show off anything new. We have quite a collection!

Don September 25, 2018

Daniel – good for you! It’s so nice to hear from one of our elder statesmen (states women?). There are no age or racial barriers to this wonderful thing we call crossdressing. Thanks for your post!

Fond regards,

Angie September 24, 2018

I’m 71 years old and have worn panties and lingerie since I was about 12. My first panties was about 7 as I was at grandma’s and fell in a puddle. My gran put me in a cousins panties . I liked the silky feeling. Still do. I wear them 24\7.

Daniel September 22, 2018

Dave – don’t worry about being long-winded. I loved your story, and you can be as long-winded as you wish as far as I’m concerned.
Fond regards,

Angie September 17, 2018

thanks dave
this has become my go to site to get feedback on the issues of xdressing and male lingerie
I find it informative supportive and enlightening. to Keri we should be able to enjoy wearing whatever we want and expressing ourselves in the way we want

stevie September 14, 2018

Angie, Stevie, and all the others, I know my responses are often long-winded and tend to veer off topic but I would like to say thank you. I am not struggling with any issues, have a supportive wife, and know my sexual/life preferences, but I also know that many others do not share that luxury. I applaud everyone’s efforts to be supportive and positive (even if only thru strict comment moderation though I like to think not) and always look forward to reading more from the community. It’s the thought provoking questions and genuine love I feel here that keeps me coming back for both clothing and food for thought. As always, cheers to the spectrum and the myriad of individuals it brings.

Dave September 13, 2018

The first time I wore panties I was in my early 20’s.
After a very intimate occurrence with my first wife I was hunting around in dark for my underwear and happened upon hers. They were a satin high cut style.
What started as a joke I put them on and I soon realized that I really loved the softness and fit. I showed her and she loved it!
Many times after that we would enjoy a nice evening with me wearing a pair of her panties. She even bought me some of my own.
I’m now remarried and my wife knows of my cross dressing. I wear panties 24/7 and never plan on changing that. My wife says she enjoys my gender fluid clothing choices.

Luvsatin September 13, 2018

Thank you Stevie for your kind words, and I agree that this site is very liberating (and supportive) for those of us who are courageous enough to accept who we are! Xdress is indeed a safe haven for us!


Angie September 07, 2018

Thanks Angie
I love this blog it is therapeutic for me.
The topics a great and the support is liberating.

Stevie September 07, 2018

Hi Robert G,

I am so very sorry you experienced the abuse you did by the hand of your step father. Fortunately, you did not lose your sense of your femme self and remained true to who you know yourself to be. Stevie, as always, you hit the nail on the head when you told Robert G. to be prepared to answer two common questions. I think almost all of us have had to field those questions with our wives or significant others: “Are you gay?” and “Do you want to be a woman?” According to research, the very large majority of us respond with “No” and “No”. We just know that there is more to us than the traditional male as defined by our society. Stevie wisely steered you to some internet resources before talking to your wife. You might also read my blog here at Xdress at https://xdress.com/blogs/news/getting-the-wife-onboard

I would encourage you to do your research on the internet before talking to your wife. There are some very helpful articles. As I said in the blog referenced above, there are some very good articles on the internet and some that are….well, not so good. You’ll be able to tell which is which, I am sure. Good luck to you, dear sister, and welcome to our sorority!

PS. to Stevie: thanks for being a constant reader – you are the best!


Angie September 04, 2018

Dear Robert
What a difficult start
First thank you for sharing
do not fear u r not alone
You have friends here
You like me and others are not attracted to men but we live femme clothing
So what some people like biker clothing jeans t shirt suits whatever that’s the FREEDOM of being you
Read good material
This is a great site
Read living with crossdressing
My husband betty

Good luck and go slow with your wife make sure you ate ready to answer the gay question and the transition question

Stevie September 01, 2018

I started crossdressing when I was in the 4th grade when I had to wear my sister’s panties cuz I had no clean underwear. I remember she deliberately picked a pair that had bows and lace and pink I remember how much I liked wearing them. So after I continued getting her panties then bra’s by the time I was in 6th grade I was starting to mess with make up and fully dressing up.

But then I got caught by my step dad and I will never forget the beating I received. He pulled his belt and beat me till I was bleeding. I had to stay in my room for several days. He searched my room and took anything he felt was feminine so I didn’t dress up for about the next year and a half.

When my mom left him I started sneaking again little at a time and by the time I was a teenager and in High School I was buying my own stuff and by then I was shaving my legs. I know I do not prefer to be with men but I do enjoy dressing up. For a year-and-a-half I did live as a female. However I decided that really wasn’t what I wanted and I preferred dressing up just once in a while. I love my wife with all my heart so now I need to start breaking it to her about what I like. I have not dressed up since we have been together but I know I am desiring it very much, but scared, and not sure what to do.

Robert G August 31, 2018

Once again great job Angie
I love this site
Like i ve always said if its made for us its not xdressing

Stevie August 29, 2018

Thank you all for your wonderful stories. It is fascinating to hear how you all got started. Stevie – thanks for your comment – shame should not be a part of our vocabulary, regarding our gender fluid selves. It is simply who we are, and we harm no one by having the courage to be honest with ourselves about who we truly are.

Fond regards,

Angie August 29, 2018

At about six years old or so I remember liking to look at catalogs we had Sears JCPenny etc. I liked looking at the panties and I remember at about age twelve i tried on my older sisters panties and I was immediately aroused. That was the last time trying panties on for fear of getting caught (very religious family). That was until about eight years ago I came across bodyaware.com website and bought the TLC Brief, the closest thing to a panty I dare wear being married with older kids. My wife didn’t think anything about them other than she liked them so I replaced all my fruit of the loom briefs. Six months ago I went back to their website to find out they’ve been discontinued. That’s when I came across xdress.com and saw all the sexy panties for men and couldn’t resist buying a few pairs and wearing them in private without my wife knowing and it felt so great so I bought more and a couple of bras. One night shortly after, I told my wife that I have always been fascinated with women’s panties and bras and bought some that were made for men and since the panties are made for men I think I feel it’s ok for me to wear them. In fact I was wearing a pair of panties and a bra under my sweatshirt and sweatpants.and she wasn’t to sure what to think. I assured her that I wasn’t gay and that a lot of straight men have the same fetish. She needed time to think she said and I said ok, I need to go to bed so I laid up there pretending to sleep when she came to bed and she started to feel the front of my T-shirt and she knew i was wearing a bra then she put her hand under my sweatpants and could feel my panties. She than put her hand up my shirt and couldn’t stop playing with my bra and started kissing me and that’s when I took my T-shirt and sweatpants off and she was all over me and we all know what happened after that. Since then she’s been just fine with me wearing panties. However I don’t wear a bra that often since its summer and I don’t want someone to see a bra line under my T-shirt. I feel so much better nowadays to be open with her and myself about my fetish, and for any other guy reading this that hasn’t wanted to tell there girl, just wait till the right time and and be upfront and honest. And tell her THEY’RE MADE FOR MEN SO SHE CANT WEAR THEM!😊😊😊

Chris August 28, 2018

Look at all of us who xdress
It’s different its NOT something to be ashamed
Some people like feet breasts butts etc some like being tied up
You like crossdressing AND you feel complete doint it
Its not wrong ITS you!
Also read book Living with Crossdressing it talks about balance of male and female

Stevie August 28, 2018

Hi, great blog and a great website.
For me it was my sisters, they started dressing me in girly clothes when I was extremely young, when I got to about 10 years old my parents made them stop, so I started stealing their clothes in secret, I wore their knickers, dress and skirts mainly, then I met my girlfriend (now fiancé) and shared with her my desires to wear feminine clothes, she straight away wanted to see so she threw me a thong and told me to put it on, since then she’s bought me tonnes of clothes and we like to both dress up in sexy lingerie for bed and sometimes just for fun.

Liam August 27, 2018

I am sorry I got cut off. I remember when I was younger when we were dressing up for Halloween and my friends told me I should have been a girl. I loved that compliment. I have no male panties. I wear nighties and nightshirts.I always wear baby dolls. I guess I should have been a girl. I love experimenting with makeup. I am really becoming quite good at applying it..I love buying clothes at xdress. I use a dilapator once a month all over my body and I shave my privates 2-3 times a week.

Holly Michelle August 27, 2018

I have been xdressing for most of life I started with panties then leotards tights and dresses. I have always worn toe nail polish and I love doing my eyes and my brows I think I am more fem than male. I

Holly Michelle August 27, 2018

I like your blog .I started at 9 with my sister pantyhose .i.sore them to sleep in .Over the year I crossdress of and on getting more then just pantyhose i’’m. with a lady who want me share my love for cross dressing with her thank sydney

sydney August 26, 2018

For me, it started at about 6 years old or possibly even earlier as I can’t remember a time when it wasn’t something I thought about. I had no sisters and my only opportunity was to try my Mothers clothing. I have always felt more like a girl than a guy. I have always hated wearing masculine clothing and “dressed up” at every opportunity I had. My entire life I have always felt like a woman and even watching TV commercials for female items like clothing or makeup or any type of beauty products always make me long to live fulltime in complete female mode. I got a job that is considered very masculine that I loved but always dreamed of being able to do it while in fem mode. I got married to a fantastic wife who I shared my secret with. She went along with it for years but never showed as much enthusiasm for it like I have and over the past 20 years or so, we haven’t done anything like that anymore. I keep my pretty things hidden and while she still occasionally talks about it, that’s as far as it ever goes anymore. I am at my happiest while dressed up and have no idea how to pursue it further than I have. Only when “dressed up” in feminine things and with pretty makeup on (done delicately, not garish like a drag queen) do I feel “right”. I would love to go shopping while dressed up and be able to try clothing on while shopping. I have considered that it is possible I’m a TS and Bi, but I am terrified of losing my marriage over it. The clothing doesn’t even have to be lacy dresses and skirts, just obviously female items. Only when I put on panties, bra, garter belt with stockings and a pretty outfit do I truly feel like myself. It has been the greatest experience of my life while at the same time leaving me guilt-ridden, ashamed and scared I will never live out my dream of doing it full time. If anyone has been in this type of situation and figured out a better way, I would love to hear about how you accomplished your dream. Being “dressed up” isn’t just a sexual thing, it is just what makes me feel like my true being.

Amber Larkin August 26, 2018

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