What Got You Started?

August 20, 2018 34 Comments

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,

Angie


34 Responses

Don
Don

September 25, 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!

Angie
Angie

September 24, 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

Daniel
Daniel

September 22, 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.

Angie
Angie

September 17, 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

stevie
stevie

September 14, 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

Dave
Dave

September 13, 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.

Luvsatin
Luvsatin

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.

Angie
Angie

September 07, 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!

Fondly,
Angie

Stevie
Stevie

September 07, 2018

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

Angie
Angie

September 04, 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!

Fondly,
Angie

Stevie
Stevie

September 01, 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

Robert G
Robert G

August 31, 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.

Stevie
Stevie

August 29, 2018

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

Angie
Angie

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

Chris
Chris

August 28, 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!😊😊😊

Stevie
Stevie

August 28, 2018

Amber
DO NOT BE ASHAMED!
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

Liam
Liam

August 27, 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.

Holly Michelle
Holly Michelle

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
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

sydney
sydney

August 26, 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

Amber Larkin
Amber Larkin

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.

rocquelle
rocquelle

August 26, 2018

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.

Stevie
Stevie

August 24, 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)
Guilt
Shame
Excitement
Occasionally 50:50 a wife a girl friend will understand and some even participate

Dave
Dave

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.

Kerstin
Kerstin

August 23, 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.

Stevie
Stevie

August 23, 2018

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

Michael (Madelyn)
Michael (Madelyn)

August 22, 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”.
Dean
Dean

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.

Terry
Terry

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

Stevie
Stevie

August 22, 2018

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

Keri (Scottsdale)
Keri (Scottsdale)

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.

GTW
GTW

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!

fmg
fmg

August 21, 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.

stevie
stevie

August 20, 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

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