My Cross Dressing Story! – Jill

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,


Like What You're Reading?

Share it with your friends!



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


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🎊!


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.


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


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…..


Leave a comment

Please note, comments need to be approved before they are published.