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,



The way I found now much I loved xdressing was different. As a total sub I connected with a dom couple, she would dress me and they would use it to humiliate me both physically and mentally. I was paraded in front of their friends and made to wait on and service them. I was tied and punished, used and abused. The whole deal was exciting but the clothing made very, very excited. Now I wear panties and thigh top stockings all the time under my "street clothes, I don’t wear bras because my nipples are pierced and I want the jewelry to show tlhrough my feminine blouses. I like make up a lot but it takes practice, I also use perfume and lots of very feminine jewelry. I’m still a sub but now it is always as a bisexual crossing make who is dedicated to “female” atire. Love your site, please keep up your work, your support is invaluable.

Dan April 30, 2019

Like many others, I had my start by raiding my mother’s dresser when I was about 12. One day each week, I had about a 2-hour safe “window” at home by myself after school, when she took my sister to her ballet class. I usually had just enough time to go through one drawer, pick some things to try on and then “model” them in front of her full-length mirror. I must have spent several of those days trying on her bras and panties, finding whatever I could to fill the bra cups – tennis balls, rolled-up socks, or who knows what! The next drawer was where she kept her camisoles, full slips and half-slips. It wasn’t until many years later that I got as far as wearing dresses, but when I did I made sure to remember to always go with a full slip. I could never get a half-slip to stay up! Then I got to the drawer where she had several babydoll nighties and matching bikini panties. After trying them on, I knew I’d spend every night wishing I could sleep in them instead of my flannel pajamas! I didn’t think of it at the time, but it would have been fitting if I could have worn the babydolls to bed, since they may have had something to do with my being born in the first place!

I don’t know about anyone else, but for me it was another drawer that held what made me long to discover my femme side, and that was the drawer where she kept her bathing suits. As early as around kindergarten age, anytime we went to the beach or to a pool, I had a secret longing to wear girls’ bikinis or one-piece styles. It probably started at a birthday party at someone’s pool when I saw the other kids’ moms in their bathing suits. I didn’t yet understand the progression of boys growing up to be men and girls growing up to be women, so I hoped I’d become a girl by the time I was their age. I probably thought wearing enough girly things would make me turn into one! I still had that hope when I tried on my mother’s bathing suits, starting with her turquoise crushed velvet bikini. In some ways it was like wearing a bra and panties, with the top having bra-style straps, but the feel of the material took the excitement to another level! We had a creek in the woods behind our house, and I so badly wanted to find a secluded spot where I could spend the whole day swimming and sunbathing as a girl! I never got enough nerve to try that, so I settled for a safer alternative, putting a towel on the floor, lying down on it, closing my eyes and imagining myself on a beach, having turned into one of the girls I’d seen on our past trips! I had to use a lot of imagination, but the bikini did its share to make the enjoyment real!

As much fun as I had trying on her bikini, it was wearing one of her one-piece bathing suits that introduced me to the girl inside me. It was an orange and yellow floral print, with three metal rings on each side holding it together. I had to fumble around a while before I figured out how to put it on, never having seen a woman do that! I held it by the straps and kept trying to step through the leg openings, but my foot kept getting caught in one of the slits between the metal rings. After a number of tries, I finally got both feet through the right places. As I got the rest of the way into the suit and slid the straps over my shoulders, I wasn’t ready for the jolt that went through my entire body. I was pretty sure that the bathing suit would fit me reasonably well, as her other items had, but when it molded itself around me like a second skin, all I could think was that I’d instantly turned into a girl as I’d wished for so long. In a way it was frightening, because I suddenly felt totally natural wearing something that was obviously made for a woman. I went to look at myself in the full length mirror and, after just two or three steps, realized that I was swishing my hips without any conscious effort. When I got to the mirror, I kept asking myself over and over if that was really me. The bikini gave me that feeling too, but the leg openings on the one-piece suit went much higher on my hips, and the seat seemed to shape my butt like a woman’s. To top it off, the molded cups, common on most women’s swimsuits at the time, gave me a full bustline. The worst part about taking it off was knowing that the next time I went swimming, I was going to have to wear boys’ trunks again, this time knowing how it felt to wear women’s bathing suits! I thought the Speedo suits that boys wear on swimming and diving teams would give me at least some of the same enjoyment, but they didn’t even come close!

It wasn’t until some time later, but I finally experienced the thrill of wearing women’s swimsuits to the pool at my apartment complex. I usually chose one-piece styles, since they were easier to find in my size than bikinis for one thing. Also, I found that one-piece swimsuits with soft-cup bras hold artificial breast forms better than most bikini tops do! I always tried to find swimsuits in floral print fabrics that would go with either red or fuschia toenails. Going to the pool was usually the way I topped off a day of cross-dressing. After going grocery shopping or running other errands in a cami top, mini-skirt and 6-inch heeled platform sandals, I’d get back to my apartment and change into one of my bathing suits. Since I didn’t want to get my wigs wet, and knew I couldn’t pass with my own hair, I usually wore flower-petal swim caps. With makeup and lipstick already on, the effect was complete. Whether I was swimming laps, doing aqua aerobics or relaxing on a float, I found that some time in the jacuzzi afterwards wound it up nicely. As for passing, I don’t know if I fooled “all of the people all of the time” or not, but to me it was all about imagining myself as a woman, feeling natural in a woman’s bathing suit, reliving the experience I had when I tried on my mother’s, and still waiting to see if enough dressing and acting like a woman will make one out of me!

Rich April 20, 2019

Wow, what wonderful and varied responses this blog has given rise to! I’ve so enjoyed all your responses and stories. It seems there is one common theme – those of us who are destined to explore our femme side are hooked forever when we try on femme lingerie. I share with you that sense that once you put on that first pair of panties, it connects you with a part of yourself you may or may not have known was there. Thank you all for sharing your personal stories. They are all so enjoyable to read!

Fond regards,

Angie March 19, 2019

I’ve always been a butt man so when I finally realized I wanted mine to look good also there were no thongs being made for men that I knew of. Now this was long ago. My wife bought me some women’s thongs and that’s where it took off. I started wearing them to work and always whenever I put on a tight pair of jeans. I really love how my ass looks wrapped in lace boyshorts, my new favorite. Just bought the Lace Brazil Brief in purple! Purple has always been my fav color. Normally always bought womens panties but usually a hole develops in the front. So excited to have a pair of lace panties w/ a pouch. I have several mens pouch panties but no lace ones and hoping these fit my butt perfectly!!
Needless to say, those first panties my wife bought me just started the whole process of me trying to have the cutest butt out there!!! Interesting when I read the blog this morning about to pouch or not. Surprised so many said no. For me though, its all about how my ass looks in my panties. Hope my order arrives before this weekend…

Tim February 27, 2019

I am not a cross-dresser, yet! My wife likes me masculine. So, far I shave my legs, chest, and sex, and she lets me. I have chosen the sexiest men’s underwear I can find, and she lets me, so far. String bikinis are good as well are an imported thong. She objected to some lace panties. I really want to get some lace panties!

Yes, I have accepted that I am fully gay or nearly so. And, am trying to figure things out?

Marsh January 29, 2019

I started in early pubescently not knowing anything about sex except I liked girls, they have a calming effect on me. I started trying by trying a bra on in our home laundry. It was electrifying for me from head to toe. I felt warm and relaxed, all my problems went away. Still, to this day, I know something is causing me anxiety or distrust with my wife, out comes the bra. fake boobs a skirt and sweater. It’s become a form of anxiety treatment, feeling warm and secure in a bra and my private sanctuary.

Sammy January 10, 2019

Yaniv great story
As lve said before some women are into it and if they are its bliss on both sides

Stevie January 08, 2019

My lust for lingerie started at the age of 12. The trigger was stockings that blew my mind. The first time I wore my mother’s panties, stockings, robe and heels. Since adolescence I have been feeling less manly than the other boys/men around me… for years I was fighting against my inner feelings and lusts and felt shamed and even avoid intimacy with women.

In 2006 I met my beloved wife and few months after we started going out, she ordered herself a sexy corset that came with a black sheer thong… I wore it after few years of “abstinence”… i felt so sexy and knew that I must tell her… few hours later I asked to wear this thong.. she was shocked but after I wore it she was so turned on and everything is history… we’re together 13 years, got married and have 2 kids. During the last year I started to crossdress more and more and my wife supports me more and more. She love me as a man and also as her sissy… I hope to be less shy and to crossdress more and especially outside

Yaniv January 07, 2019

I m no expert but trying to hide it is probably a bad idea. See if you can wearsome male lingerie thats not too obvious to get a feel for what she’d say!
But best is to be upfront and honest with her about your desires

The clothes here are fantastic
I dont look at wearing these items as crossdressing because they are mens garments with some femme styling. Women do it all the time wearing boyfriend style jeans and other male styled things

Stevie January 06, 2019

I recently discovered your blog. Have read most all of it. I enjoy your openess and breath of knowledge.

Some months ago I discovered my wife’s razor in the shower, started to shave my legs and everything else! My wife challenges me about my shaving but, so far she has accepted my excuses.

I wear some very brief and sheer bikinis to bed. My wife has not connected the bikinis with my shaving. Hope not! I want to get some cross dress items, but my wife wants me to stay masculine!

I was surprised when she told me, “See those women? They are gay!” Why? Because they are wearing the same rings! I would never notice this detail!! So, what is going on? Is my wife gay or does she just have sensitive gaydar?

Any thoughts?

Chrissy Marsh January 06, 2019

I get what you ate saying
I m not gay or “femme” but i love women’s clothing and I love wearing pretty sexy stuff.
i really like the contrast of the male female

Stevie January 04, 2019

I had always enjoyed looking at all the women in panties featured in department store ads in the Sunday paper. Then one day I wanted to know what it felt like to wear a pair of satin panties. I then noticed that my older sister had a few pairs of pure satin panties. I couldn’t help myself and had to try them on. I immediately got so very excited. I couldn’t help but touch myself. Since then I have explored my lust for wearing panties everyday, at times cross dressing, and getting excited seeing other men wearing panties.

Jess January 03, 2019

I can’t remember exactly when I started wanting to wear women’s clothing. My first attempts were with my older sister’s and cousins underwear. At first they did not have bras, but as they got started, so did I.
I have never tried to pass in public, has always been my personal secret.
Now I am blessed with a wife who accepts me as I am, and understands that I am not actually gay (although have had a couple of experiences) and not really a femm. I just like the style and feeling of female style clothing.
This site has been a real blessing, as finally I can get sexy clothes that fit me!

Rhonda January 01, 2019

I was on holiday with my uncle, aunt and niece (who is year older than I am). We slept in an holiday house and shared a bedroom.

After she had a shower she came back in the bedroom ad started to get ready for bed. As she was standing in her undies I could not help getting an erection. She got cross and said It is wrong to get hot over family members. After being a bit ashamed I said it was her silk undies that made me hot. She relaxed and we went to bed. After a few days of me getting an erection and her obviously enjoying it she asked if I had ever touched a pair of panties and she grabbed a pair form her suitcase. She gave it to me and I got really embarrassed. She said it was fine and that I should try it on to see how soft it feels. So I did and slept in it that night. I have never stopped wearing panties since.

When ever I see my niece she still always asks me If I still like it.

slipj December 31, 2018

OMG! I really love this site!

I started out wearing my wife’s panties when we first got married in 1991! She has never known about my fetish either! She always wore some of the cutest panties and usually had “upskirt” incidents that just made me wild! (So were others that saw her amazing thighs and, well you know the skinny!) I still wear panties as often as I can. She and I split up a few years ago and that is when I got more and more into x-dressing. I typically don’t go out of the house but I really enjoy the feel of women’s clothing, especially lingerie. My current girlfriend buys me cute panties and has me wear them often! She love looking at me in them, however, she has not seen me in a dress, skirt, blouse, etc. Recently, a guy at the golf course noticed I was wearing panties, (I thought I was alone!). He complimented my and we have actually gotten really close! He has “taught” me some stuff and we go out on occasions, me fully dressed! I love my girlfriend but I really enjoy the additional rewards of dressing in pretty lingerie.

Leo November 25, 2018

I started wearing panties (mothers at about 10 y/o. I went full time when I was 13. Mother caught me in her pink vf panties and ask if I would like to wear pink VF panties, Yes. she went to town and got me several of pink VF panties. I wore them until I went into the Military. Then I met this lady that later would become my wife She would let me wear her panties. VS with lace on the legs When we got married we were both were wearing panties. We moved into this apt house . One of the tenants that we got to know was a beautiful sexy woman, 13 Y/o son and father. Evelyn would wear pink or white sheer baby- doll pjs with a pad to cover her ? Ken would wear a pink or white sheer baby doll with sheer panties, John would wear black sheer baby-doll with sheer panties Ken would come to our apt every day after school, He would go home change clothes into sheer baby-doll. some times with one of his mothers bra and some times a pair of black or white 5 inch mules He sure was sexy. I

Gail November 24, 2018

Dear Carla
I feel ya
If only we could be ourselves in front of the ones we love
For all at the beginning of a relationship its much better to tell the partner as early as possible at the time yku feel appropriate
That way you dont have to hide

Stevie November 23, 2018

I seen this blog and read through some of them and decided I had to share my story.
Years ago, my cousin came over and she had on some black shiny looking knee high boots. They caught my eye and I just had to sneak them on. Omgosh….they felt amazing! That was start. My curiosity then started to get the best of me so around 17, I started sneaking in panties to wear when I wasn’t playing sports.
In my early 20’s, while my ex-wife was away at work, I tried on her corset with stockings and feel in love with the sexy feeling. No, she had no idea I was crossdressing.
Now with my current wife, she only knows I have worn her panties a time or two but she has no idea I have heels, mini skirt, tops, bras, panties and several pairs of leggings. I would wear anytime if she would ask, but I know for a fact she is not a supporter of my secret desires of dressing. Am I gay, no. I absolutely love the feeling I get when I am dressed up….and I don’t have to be completely passable to feel like I want to feel. I wish but I know it’s not a happening thing for me.
Thanks for listening!

Carla November 08, 2018

It started for me one Christmas when a present for my sister had my name on it. When I unwrapped and opened the box it was a pair of panties and training bra. Anyway, everyone started laughing at the mistake and we all had fun about it until someone said well I guess it was your gift so you can do what you want it. Well at that moment I said that they just might be my size. Than in a laughing manner I heard someone say try them on. Well after a few I did retreat to my bedroom and tried them on. The erection I got when I slipped the panties on was no Joke and they did fit very nice. I looked at myself in the mirror and knew at that moment that my tighty whiteys days were over. Anyway, when my little excitement went down I put my clothes on and went back out for Christmas. My sister asked if they fit and I said yes … they are mine now. They wanted to see so I showed the bra and the top of my new Christmas panties. I didn’t wear the bra again but wore the panties out. Anyway, to make a long story short, since that time I have worn only boys/male bikini and string bikini underwear or panties. Today I wear only fem panties and would not have it any other way thanks to XD .. and to think this all started from a Christmas present mistake.

Pauley October 30, 2018

can not quite remember, but I was young……………..used to wear my mother’s bra & panties. As I got older I was really into it…..when I traveled on business…………I had or shopped for femme clothes and “dress” up and play with myself. it was so hot.

Jack Harris October 22, 2018

I got started quite yong 7 or 8 I remember the day very well I was in the laundry room with my mother, she pulled out a pair of orange satin panties with lace trimming on the legs, they were so shiny, she folded them and placed them on the the pile of clothes I new were one of my older sisters, I wanted to feel them so badly, I sat there have mesmerized as I tried to continue to play, my mother finally left the room, I quickly snatched up the smooth garment rubbing it on my face, remembering where I was I looked around and quickly stuffed them in my pocket and ran up to my room, closing the door behind me, I retrieved them from my pocket and again rubbed them on my face, the feeling was exquisite, I had to try them on, I dropped my pants pulling my tighty whitys down with them, I slowly stepped into them, they felt amazing I wore them for two days, when they got soiled I would just put them back in the hamper and searc for a new pair, sometimes having to sneak into my sisters room and grab a pair, this went on until my sisters moved out, by then I was driving and could go buy my own, wow what an experience that was, but that’s a story for another day, needless to say I was hooked, and now have very understanding wife who not only accepts my feminine side but helps me pick out things and often surprises me with a special purchase.

John October 16, 2018

I started at about 16. Sneaking my moms nylon panties and hose. Excited me. I remember when I was 5 or 6 my aunts dressed me up and went on about what a pretty girl I was. Fast forward to when I was about 44 and worked at post office. I had packages from bigalslingerie delivered to po box. Every item that came, gogo boots. Panties. Lingerie. Bought panties and sexy clothes at lane bryant. Since then have dressed in private at home or on single trips. Wife has found panties. Old fashioned so wouldn’t accept so I still have to be a gurl in private. I have been told I have pretty fem features and luv to makeup and dress. Haven’t been brave enough to go out dressed

Melissa October 08, 2018

I first became curious upon seeing panties on the side of the road as a kid (about 7 or 8). This was back in the mid 90’s and what I saw was a hanes small scallop trimmed purple bikini panty. When I finally decided to try them on I didn’t just try them right then and there though. I went into the bathroom and got some detergent then hand washed them. After I rung it out, I decided to hang them in my closet hidden so no one would see them. But I couldn’t resist. I slipped them on and I instantly loved how they fit. I liked them so much I danced around my room in them. One of the purest times of my childhood when sex wasn’t even a thought in my mind. I did however like the clothes girls wore but didn’t know why.

Dave October 08, 2018

Loved reading the comments and I’m going to share mine soon. I’m 63 years young and I have been dressing and playing with female attire for 50 plus years. A number of girls helped and a wife of 20 years had a great time. My current so is younger and ever more supportive. She did find this app. I will have the how it started story soon. A little bit began in mom’s beauty parlors. Thank you for the form to read about other people like me and a place to tell them about me.

Steve LeProhon October 03, 2018

What a great reveal
This is the place to let it all out with support and no judgement
We are all alike and different so to speak
Lots of us dont desire sex change but lots of us do
Some of us like you love the feel of the clothes
So welcome feel free to post on all the topics
Angie is great

Stevie October 02, 2018

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