My crossdressing journey started when I turned 12. I went with my family on a holiday to the beach. One day, as they were all off swimming, I stayed home to sun-bake. For some reason, my mother had taken my swimmers with her in the car. I had the choice of sunbathing naked or in a pair of shorts. I happened to look in the clothes basket in the lounge room and saw my sister’s bikini. “Why not,” I thought? I stripped down and put on the bottoms. They were bright pink and had bows on the sides; they fit perfectly. I found the top, put it on, and the ensemble was complete!

Looking at myself in the mirror, I saw a girl. What a strange feeling it was looking at the bikini clad figure in the mirror. It sent a tingle through me. I spun around a couple of times, and then went outside to tan for a couple of hours in the sun. I ended up having to wear a shirt for the rest of the holiday because of my bra tan!

It started me down the path of borrowing my sister’s clothes, particularly her underwear. She was a year older than me and her clothes fit me perfectly. I started to let my hair grow longer, like some of the hippies at school. My parents wrote it off as teen rebellion. Soon, I had hair longer than some of the girls. When I was alone, I styled my hair with ribbons and hair clips to see how it looked. Wearing my sister’s underwear and clothes, I danced around in my room.

At age 16, our school had a reverse gender social. The boys dressed as girls and the girls as boys. My sister convinced my mum to help get me ready. They put a dress on me, did my hair, and even used makeup on me. My sister had me put on one of her bras, which she padded with some tissues. They were shocked by how I turned out; my mother even commenting on how much I looked like a girl. My sister dressed as a boy, and together we won the award for best dressed couple. Afterwards, my sister confided in me about my desire to dress in girl’s clothes. She offered to help me with my dressing in the future. I asked her if I could borrow her clothes. We kept it a secret, and she started buying me women’s underwear, hiding them in her room so my parents wouldn’t find out.

Years later, after I moved out, she would still help me by giving advice on what to wear and where to wear it. I went out a few times dressed as a girl, but always to places where I wasn’t known. Eventually, I met a girl and fell in love. Figuring that she wouldn’t understand my crossdressing, I threw all my girl things away. I resigned myself to being “normal” for the rest of my life.

Now, 25 years later, my kids are grown. The wife and I started looking for ways to spice up our sex life. We rented DVDs and read blogs online for ideas. One night, she informs me that she has found another interesting thing for us to try. She suggests that I wear women’s panties. I could barely contain my excitement. I quickly agreed, and my wife took me shopping. Pretty soon, I had a nice collection of satin and lace panties. Next, she expanded my collection to include training bras and a few boob tubes.

These days, I wear women’s panties everyday under my work clothes. The feeling of satin against my skin as I work is incredible. If I am wearing a jumper all day, I wear a bra as well. At night, I wear a nightie, usually a pink or blue pastel. I have separate lingerie for summer and winter. In winter, they are old fashioned—Victorian style with lots of ruffles. I have a collection of skirts and dresses that my wife has picked out for me. I cannot wear them when the kids are around, but other than that, she’s given me free reign.

Sometimes, we’ll go out to a bar, my wife pretending that I’m one of her girlfriends. We have a great time teasing the men at the bar. I’ve received so many proposals that my wife jokes that I could have been a hooker. She does my makeup and hair. She tells me that I resemble my sister—that is, the sister she never had instead of the brother she does.

My normal evening consists of coming home, changing out of my male work clothes, putting on either a skirt and blouse or nice dress, and then cooking us dinner. When my wife gets home from work, she appreciates me having a meal ready for us to eat. After dinner, I wash up and we watch TV until it’s time for bed. I change into my nightie, tie my hair back into a ponytail, and we head to bed.

My life has come full circle. I sometimes regret the lost time in the middle, but patience, and some great luck has brought me to a happy place. The moral of my story; when your desires seem to evaporate in front of you, have some patience, because one day they just might come back around.

En Femme Style


More Articles by Michelle Tolley

    View all articles by Michelle TolleyTags:
    5 1 vote
    Article Rating
    Notify of
    Inline Feedbacks
    View all comments
    Lisa watson
    Lisa watson
    4 years ago

    Awesome story michelle .


    Katie Daily
    4 years ago
    Reply to  Lisa watson

    Yes it definitely is a great story that came true…Unfortunately my story seems to be turning into a nightmare as of late. You Sir unfortunately my story seems to be turning into nightmare as of late. See our computer was on the fritz. So I took it to a local shop to have it worked on. I asked the technician to please remove any X-rated pictures or porn that may be on the computer. And to save all the important files and put everything back the same way. However when I receive the computer back I didn’t have time to… Read more »

    Lori Shane
    4 years ago

    You’re so lucky to have women who have accepted your dressing

    Trusted Member
    4 years ago

    Michelle ,
    What a wonderful story… Your wife is very special that you can share your feminine side with her. Give her an hug for me.. As you can guess , I am a little jealous… My wife knows and prefers not to participate…. ” don’t ask don’t tell” … We are both retired and she will arrange outings with her friends… “I’m sure you will find something to do” when she leaves. LOL.
    Thank you Michelle for sharing with the ladies here at CDH…. Leonara

    skippy1965 Cynthia
    Trusted Member
    4 years ago

    Congrats on coming “full circle” and thanks for telling your story so well, Michelle!

    Olivia Livin
    Trusted Member
    4 years ago

    Thank you Michelle for sharing. It’s a truly marvelous thing when we’re lucky enough to have a relationship with our SO’s where we are not only supported but appreciated. I think it has to do with mutual respect and huge amounts of honest communication. It can also be quite playful and fun…from what I’ve come to understand lol. I wish it could be this way for so many others as well.

    4 years ago

    That is fantastic you are so lucky

    Barb Encourt
    4 years ago

    Such a nice story with a happy outcome.
    Hold on to your wife tightly as she is one in a million.

    4 years ago

    You’re so lucky, Michelle, to have a wife who actively encourages you to dress and be yourself. A lovely, heart-warming story…and you have plenty of time before you to go on dressing.

    Christie Deville
    4 years ago

    loved your story….thanks for sharing



    sarasue olson
    4 years ago

    Wonderful story, and your very to have such a caring sister. I also had such A sister two years older than I, she caught me checking out one of her nighties I was getting to the point at fifteen to start experimenting with her panties and lingerie but hadn’t started wearing them yet. She loaned me A nightgown and A pair of nylon panties to try out. I was truly struck how they felt on my body and haven’t looked back since. My sister filled me in about my dad also crossdressing and told me that they had worried that… Read more »

    Would love your thoughts, please comment.x
    Subscribe To Our Newsletter

    Subscribe To Our Newsletter

    Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

    You have Successfully Subscribed!

    Log in with your credentials


    Forgot your details?

    Create Account

    If you don't see the captcha above please disable ad and tracking blockers and reload the page.