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,


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I really liked this article by Jill. For me, it also started while bringing in the laundry from the clothesline. I was about 11 years old. With mom & both sisters all wearing nylon panties, feeling their panties, nylon slips, half-slips, etc., I soon had the desire to rub them on my skin/face. Back then, women’s nylon panties had a double layer of nylon in the crotch and NO COTTON lining like they do now days.
With very little pubic hair at the time, their panties felt so naughty & nice! For this reason, I always REMOVE the cotton lining from my panties prior to wearing!

Karli…like you, I too really enjoy wearing panties as my # 1 item of lingerie. I wear women’s nylon panties every day.

Jamea…so good to read that you also like motorcycles. It is an awesome feeling to be riding your motorcycle while wearing a 6-suspender garter belt and nylons. When putting your feet down at the light, you are quickly reminded that you are wearing nylons when you feel them pulling on your garter belts! Because I often wear panties that have a large “lace” waistband, I have to be careful that my shirt does not ride up, exposing my lavender or pink panties.


I have a tender fem side and also masculine hunting, motorcycles, farm equipment, etc. I was looking at crossbody purses as mine, hidden away has started deteriorating. Our Amazon accounts show all that we look at and i was amazed to see under my side of the bed one similar that i was interested in. I am not sure if my wife put it there if it is a test or it is intended for me or just a coincidence. She does not like to have or keep anything under beds. I have not had the opportunity to question that so in a few weeks when i get back home i will pursue the questioning and hope for the best…..


i find myself dressing more every day its hard to be all male its almost like a drug i just cant stop have fun and enjoy urserlf


This blog is a great place for people to share their thoughts and experiences! Thanks for maintaining it.

Jill’s recent posting, as well as some earlier posts and comments, triggered a few thoughts:

My early experience with the sensual lingerie seems similar to many others. Being drawn to sensuous silk and satin fashion should be no surprise. Throughout history sumptuous garments have been the providence of royalty and privileged individuals. Strange that this legacy has been lost to many. Maybe people who find erotic pleasure from lingerie and other sexy items should be considered “gifted and talented in the arenas of sensual pleasure”. 😉

Finding items that provide comfort and continuing sexy feelings throughout the day or night can be hit-or-miss. XDress solves the challenge of finding lingerie that fits more masculine body types.

In terms of increasing support of a partner…here are a few thoughts that may be of value to some:
Incorporate the inclusion of lingerie, costumes, or whatever into a broader effort to increase eroticism in a relationship. For example, Laura Corn’s “101 Nights of Great Sex” provides ‘secret sealed seductions’ that are initiated by either partner and cover an exciting range of possibilities. (There are many other resources.) When moving to incorporate more sensual dress, doubling down on ensuring that a partner is getting over-the-top pleasure may be of value. Women may overlook the fact that men’s primary pleasure centers are more on the surface. If they haven’t experienced the impact of rubbing a guy with their silk lingerie or slipping a sensuous bikini or tap panty on him or rub his chest with a satin bra or cami, they might be surprised at the positive results. I have mentioned to my wife that a woman can enhance and extend erotic pleasure with a piece of plastic and battery and that is considered standard play…so what is unusual about a guy feeling good when wearing a silk panty under golf pants or at the office, or other erotic adventures?

Maybe these last two thoughts do not need to be mentioned but unfortunately, they seem to be too common of a concern. (1) If a guy does not pull his weight with household or child-related needs, and his partner is exhausted, she is not likely to be as supportive of venturing into unfamiliar erotic play. (2) If a guy lets his physical condition go it may not result in over-the-top interest from a partner.

Cheers to all. I look forward to the anticipation/excitement and small thrill I experience when receiving and trying on another sexy item from XDress.


Hello, good evening to you. I would like to say that I really found your story interesting about being a cross – dresser and all as I found that when I was 8 years old I wore my mothers friend daughter panties and I found them so comfortable but I could not come to terms with who to turn to or who to tell. I was hoping me myself coming here would find a answer 😊?


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