My Cross Dressing Story! – Jill

So I’ve been asked to share what being a crossdresser is like, for me at least. I’m certain that while my feelings and experiences will resonate with some in our community, still others will struggle to relate. And that’s okay. Any response that isn’t rude is welcome and encouraged.

For me, my awakening came like an unexpected flash of lightning. When I was 13, my mom suggested to me and my brother that one of us should dress up as a girl for Halloween, but for laughs, you know? And in an instant I knew that I wanted to, but I also knew in that same instant that I wanted to dress as a girl for more than just a costume, more than just a cheap laugh. I ended up wearing a wig and a denim dress that Halloween. Nothing more.

But this was 36 years ago during October in the mid 80’s. At that time is was practically a crime to be gay, so I’m not sure how bad it would have been for a heterosexual boy like myself, who was quite small and not particularly strong and robust to come out and say “I want to dress as a girl.” I’m betting things wouldn’t have gone well to say the least. It was another two years before I had another chance to wear something designed for the feminine form.


It happened by chance one day while I was home alone and doing laundry. When I was putting my wet clothes in the dryer I found a pair of my sister’s panties that she had left in the dryer. I picked them out of the dryer and held them up. Suddenly those feelings came rushing back. Seconds later I was in my room undressing, my breathing was fast and ragged. With her panties around my ankles I paused for a moment, trying to decide whether or not I really wanted to cross that line. Of course I did! I’m sure you all can imagine how I felt otherwise you probably wouldn’t be on this site reading this blog. But just in case, I felt amazing! So pretty and girly!

Over the course of the next two years, I would occasionally sneak into my sister’s room and borrow a pair of her panties. I would run back into my room, quickly put them on, then I’d…...well, you know. But it wasn’t just about sexual gratification, it was how beautiful it felt to feel so delicate and feminine. But I stopped because I also felt shame. Shame for enjoying how good her panties made me feel, for feeling like I was some freak deviant, a monster. But also shame because I’d borrowed something intimate without her permission. It would be many years before I wore panties again.

When I was 26 I dated a woman, the particulars aren’t important. What is important is that she asked to put on her panties one night. I had to play the tough macho guy initially but finally “relented”. During the three years we dated, I wore her panties many times, often without her knowledge.

In my 30’s I would occasionally buy panties and even a few bras! Oh how I loved my bras! But again the shame would come rushing back so that after owning my feminine things for no more than a couple of weeks, I’d let the shame force me to throw it all away. This happened in a vicious cycle of buy, enjoy, shame, and finally purge. And it happened again and again throughout my 30’s.

When I was 41, I moved in with my girlfriend who would later become my wife. As I was packing to move into our new place, I realized that I’d never again wear women’s clothing. Although I didn’t like that, I was okay with it since I still felt like it was wrong.  It would be several years before I realized I was wrong.

At the beginning of this past June, my wife and I were having a conversation about our sex life when I blurted out that I wanted to buy panties for myself. My usual tact was not present that night. I was like a drunk playing with a hand grenade, just pulling the pin and tossing it out there to see what I hit. My wife of course had numerous and understandable questions. Was I gay? Did I want to transition? Why didn’t I tell her sooner? No I wasn’t gay and no, I didn’t want to transition but I didn’t tell her sooner because of my guilt and the stigma surrounding guys who wore women’s clothing. Cross dressers were queers, losers, child molesters and so on. And I didn’t want my wife to think of me in those terms. Can you relate to that?

We talked a while, until she was sure I had told her everything. Then to my surprise she went to her dresser and pulled out one of her nighties and had me wear it. It was thrilling to wear it and part of that thrill was from the fact that my wife was watching me. In other words, I wasn’t going behind her back.

About five days later, my wife texted me while I was at work, saying she had a surprise waiting for me under my pillow. What could it be, I wondered? Panties? A bra? Divorce papers?!? All seemed like possibilities. When I came home in the morning I made a bee line for our bedroom and my pillow. Under my pillow was a note in which she expressed her gratitude for opening up and sharing something very personal, and a bag. I opened the bag and pulled out five pairs of panties and a halter top teddy all my own! I was damned near moved to tears. My wife is very accepting and supportive and getting more so all the time. I’m very lucky to have such an amazing compassionate woman to love and to call my wife.

With her help, I’ve realized that being a cross dresser isn’t something to be ashamed of, to feel guilt over wearing and loving women’s clothing. None of us should. It’s clothing and it puts us in touch with our feminine side, our gentler and kinder aspect of our personalities. At least it does for me. We shouldn’t have to feel like we need to sulk about it like criminals in the night. We should all be so fortunate to have a significant other who is so supportive and understanding.

Since I came out to my wife, we’ve gone shopping together numerous times. Because of her kind heart, I now own three more beautiful nighties and I feel like I need more, and a cute and very comfortable nightgown and two camisoles. We’ve also gone to a thrift store and picked up a cute coral colored cocktail dress and a simple but very soft blouse that fits me like it was custom made for me.

I’ve acquired a few more things since then but that’s not really the point of all of this. The point is that I’m not some horrible monstrosity because I love how women’s clothing feels against my skin or how it makes me feel inside, and neither are any of you. I still have a long way to go before I fully accept Jill as being an integral part of who I am as a whole person, but I’m on this new journey and I’m excited to see where it goes from here!

My best wishes for all of you,

Jill

14 comments

This is fantastic Jill! I’m incredibly excited for you and your SO! Supportive partners love each other through everything – including the fears of others.

Lotsa Satiny Hugs!
TA

TA January 09, 2022

Have found lingerie sensual from at least my teens….my first multi pack of nylon y-fronts were as close as I dared to go initially—-but love xdress bras, garter belts, nylons, and panties as a way to express sensuality. Also find leather, latex, flannel shirt n Levi’s and more oh so sensual. Think it is truly sad society has for the most part classified sensual wear whatever it may be according to expected gender roles. Intimacy is adult play, let’s do just that, OK? Mike

Mike January 04, 2022

Hi Jill,
Thanks so much for sharing your fabulous story, I can relate to so much of it, in fact some portions of it are almost identical! Like you I’m fortunate to have a woman who understands and actually enjoys and actively participates in my femme side. I “came out “ to her in a similar manner as you with much hesitation and trepidation but things worked out quite well much to my surprise! It has greatly improved our sex life and brought us closer in other ways too.
Too all the straight guys out there who want to/are exploring their feminine side, I say go for it! I realize that many of you can’t do so at all or at least to the extent you would like, but the time will come when you’re ready/able to. Until then, keep underdressing as I did (and still do at work) til you can fully express yourselves.

I wish all a safe and happy New Year🎊!

Riann December 31, 2021

I think as we develop as a culture, we will be more open to these ideas. 20 years ago, things were so much more repressive than they are today and 20 years from now w things will be even less repressive. Have the confidence to break these stigmas in life. You will be surprised how your SO can be when you share the most intimate and vulnerable moments with her/him.

Scott December 30, 2021

Jacky
You are so fortunate! 1. To have a relationship where u felt safe enough to tell ur SO! 2. She is somewhat accepting ! Cherish this time with her! As you will see from some of the posts its hard to get lightning to strike twice with another person.

Always make sure she knows ur still her man !

Get ur lingerie on
I did
Stevie

Stevie December 26, 2021

The story is almost related me also. When I wan teen I tried to find some gents underwear with attractive colors but all the time I was disappointed. when I was 27, I bought some sexy lingeries for myself long distance gf but I didn’t send for some reason. One pleasant night tried it, it was amazing and I did… that’s was starting point. I Now I am 36, during this period I bought lots of panties and bras and used them and felt guilt and bin them. Before married I told my wife ( not a long distance one) I would like to wear girls panties only during s… (of course I lied) the first question was I gay or trans. I said no, just a pleasure. She agreed and she allowed me wear her panty only during interc…. Yesterday I confessed I would wear full outfit and play a girl role. She was laughing and confused. But she agreed somewhat.. will see what happens…..

Jacky December 24, 2021

Thom i feel u
It starts young most of the time
But who cares if no one likes us

Stevie December 14, 2021

Wow
What a stimulating topic
We all have a story and thats what makes explaining crossdressing so difficult. Its not the same for every one! From the reason to the gender! There is no one reason!

As for me I started with moms shoes! That progressed to stockings nail polish on my toes to full on dressing and transformation to a female. Unfortunately i looked horrible as a female ! So at 50 after 42 yrs of dressing ( with a hiatus age 14-25) i began to research why people xdress and y i crossdress. Now I d be lying if it didn’t really turn me on ! But as I age i just love feeling pretty sexy and invigorated!
I explored any gender changes i needed to make and found none!

For me I m just a guy who loves loves the clothes the shoes the nail polish the dresses the skinny jeans! I m not trying to look like a girl.

I ve now settled on the fact that i like lingerie pretty nail polish and light make up ( to enhane my look ) women s jeans and sweaters

I can not leave out that i love the taboo part of it
The naughtiness of it
And the sensuality

So that s my story
Love this blog

Get ur lingerie on

Stevie

Stevie December 09, 2021

Hi Jill. Thank you for your blog. You bring back to me a renewed appreciation for my amazing wife, who has probably bought more of my panties, bras, and skirts than I have. We have a very full and loving life because of our acceptance and celebration of each other. I certainly hope this is true for you as well. I must say that I think Tom has a point in the awkwardness of referring to ourselves as crossdressers, in view of the fact that women dress as men all the time and no one even turns a head. Let’s just say we are gender fluid and love the femme within. Good luck to you, Jill, in your future, and may you and your wife find many blessings in this new frontier.

Affectionately,
Angie

Angie December 07, 2021

Hey to all my fellow friends of the cloth, it’s nice to belong to like and kind. I still wear panties but I have purchased many of xdress items, it’s so hard to just toss what I have been wearing all my life, 66 years and still love that feeling like the first time. So now I have a choices of what to wear, thanks to xdress.

Martin Gallegos December 07, 2021

The first half of your story sounds a lot like my early experiences (at 12-13, lacking the Halloween part). But finding that pair of panties left behind in the laundry room and the feeling of actually appraising them seemed so naughty and taboo at the time. I couldn’t get it out of my mind though, and for the longest time I tried to disregard the notion, then eventually I just had to try’em on… and I swear it was like magic, all of a sudden a feeling shot through me from head to toe, like a bolt of lightning and a rush of lightheadedness and an incredible erection (which I didn’t even know what to do with), it triggered something inside of me that couldn’t be denied or explained, and yeah I thought I was the freak. As time went on I suppose (or at least thought I did) I outgrew that prepubescent curiosity. A few decades later, home alone (while GF is out of town), for some reason I couldn’t resist, almost instinctively like I tried on a few things (out of horniest maybe), but it was the stockings, garter and panties that cause an eruption in my mind (and heart), it was exciting beyond belief, wearing something so feminine could make me feel so good, it was luscious…
And my girl I thought she was pretty cool, I mean she liked wearing my stuff (underwear and shirts, I thought she looked sexy and not knowing of my proclivities), one day, when she came home and found me in her things, Oooh Boy, she liked to blew a gasket! She says, “We gotta’ talk!”. Well, I still love her, but surely miss her.
To have had her support/acceptance would have been so wonderful (and this was before the internet). So I’ve been a solo act since, secretively and privately at home alone. Loving every minute of it just the same! And sure, I’d love to have a lover that would be so willing to adventure into my life, but I’m OK with what I do have. A little narcissistic, maybe, but for these daze it’s all ggg…

I could really go on but you get the gist. 😘

Gigi December 07, 2021

Thanks for sharing your story. I’m vrry happy to hear that she love the other side of you. My wife also accespt and support my desire for lingerie.

Yaniv December 07, 2021

Jill, thank you very much for your honest and open blog. Many aspects of your story are close to mine; I can readily identify with a prior history of purging and shame. It took a cancer diagnosis (fortunately no longer a concern) and my children being at least college aged before I was better able to come out to myself and work towards more fully accepting myself, even appreciating that aspect of my self. I take great pleasure in wearing lingerie, particularly panties and nightgowns. I am a very loyal and appreciative exdress customer. I still am uncertain about the term cross dresser, as it isn’t used for women who wear articles of men’s clothing. I note, just as a manner to recognize and celebrate diversity, that I have not given this aspect of myself a female name. I am deeply thankful for all who have lived and do live their authentic self, for it has been freeing to me as well.
Love the diversity. Love the open expression of self. Enjoy my lingerie. Enjoy the services of exdress.

Tom December 07, 2021

I loved reading this and your new freedom with your spouse. I have a same sex attraction I am struggling with but as far as being transparent with my wife. She knows my feminine side is also a part of me she accepts. I buy feminine body wash and shave smooth my groin area. I drawer is accumulating more panties especially thongs and I will express my love for a hard d when we are in intimate talk. She also wants to try with another woman. To be continued with this love for cross dressing 💕

Ronne" December 07, 2021

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