Full Circle

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.

Stepping Out Secrets

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.


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Leave a reply

  1. Alice 3 days ago

    Thank you for sharing! Wish that our significant other will be so understanding and supportive!

  2. fiona moss 6 days ago

    wow michelle! what a truly amazing wife you have. I am so pleased she has brought you joy and happiness. thankyou for sharing your story with us michelle 🙂 .

    fiona xxx

  3. Katie Daily 1 week ago

    Your extremely lucky. My wife is totally against it. I’m worried she may tell everyone we know

  4. Christine V 1 week ago

    Youre lucky to have a wife who helps you dress up

  5. Danielle Wayne 1 week ago

    i am inspired by your article. I have hopes for my wife and i, as we are just now starting this journey…great read…thank you

  6. Carrie 2 weeks ago

    OMG that is exactly how my experiences started except we were on a family vacation, and it was my cousin’s bikini I jumped into and saw a girl in the mirror while everybody was down at the beach while by myself, except I was around 7 or 8 at the time, my oh my I really do need to sit down and write this out, I believe it would be very therapeutic in doing so.
    Thank you so much for your story Michelle
    Love Carrie

  7. Keri Sanders 2 weeks ago

    What a great story and you must have been an adorable little girl

  8. Sarah Mack 2 weeks ago

    Thank you for sharing that wonderful story I’m so glad your life is coming to full circle

  9. Chrissie Cross 2 weeks ago

    You’re a very lucky girl Michelle! I’m still in the “patient” stage. 🙁
    Thank you for sharing your story. It gives me hope. 🙂

  10. Happyinmysilks 2 weeks ago

    Thank you so much Michelle!! You’re Amazing and so is your post and your story!! I love that you found yourself and have come full circle!! I can relate to that feeling so much .. You’re Amazing!!

  11. sarasue olson 2 weeks 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 I may find out and how i would handle it, Dad and mom were relieved when my sister filled them in on my activities And sat us down and had A long talk with us and made me promise to keep it in the family. Mom bought me ten pair of white nylon vanity fair panties and A blue baby doll with bubble bloomers, my sister and mother went thru their old clothes and picked out things such as dresses slips sweaters skirts nightgowns and gave them to me. I could hardly wait to get home from school to dress up and do my homework I loved it when my sister would help me with my studies. Our family seemed to draw closer together my school grades improved greatly my sister and i became good friends she also had her friends give me their cast off clothing and I soon had A dresser and closet full of girly things. Fast forward, when I was in collage I couldn’t dress up due to having roommates that was A real bummer but I was dating some very nice girls that seemed to help some, I tried to feel them out about guys that wore women’s things and got some very negative feedback, that went on until my senior year and met A charming lady that I really cared for as we dated I brought up some of the guys were wearing panties they nailed in A panty raid to see her response. She thought it was no big thing because guys had to wear such nasty underwear they were smart to try panties. She said her younger brother would wear her old panties and loved it, then came the shocker when she said you should try it. to that I responded I have, she said do you like it? I gave her A big yes. I started to tell her about my interest in lingerie, she was very interested in my experience and wanted to hear all about it, she said it turned her on and loved all I had to say.
    I asked her if she would by happy with A man like me, She said very I asked her if she would marry me and got A big yes. We have been married over fifty years and have two daughters we didn’t hide my dressing from them and they have no problem with it. For those who are planing marriage do like I did. Don’t hide it be honest with your prospective partner it will save you from A world hurt if you wait till later. If your rejected you will find someone that truly loves you for what you are not somebody your not. Good luck

  12. Christie Deville 2 weeks ago

    loved your story….thanks for sharing



  13. Robyn 2 weeks 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.

  14. Barb Encourt 2 weeks ago

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

  15. Glory 2 weeks ago

    That is fantastic you are so lucky

  16. Olivia Livin 2 weeks 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.

  17. *skippy1965(Cynthia) 2 weeks ago

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

  18. Leonara 2 weeks 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

  19. Lori Shane 2 weeks ago

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

  20. Lisa watson 2 weeks ago

    Awesome story michelle .


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