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.

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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.

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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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Michelle Tolley

Cross-dressing since 1970. 6'2" tall. Brown hair.

Latest posts by Michelle Tolley (see all)

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Chrissie Cross
Chrissie Cross (@chrissie-cross)
1 year 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. 🙂

Sarah Mack
Sarah Mack (@sarahmack51yahoo-ca)
1 year ago

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

Keri Sanders
1 year ago

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

Carrie (@carrie7676)
1 year 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

Danielle Wayne
Trusted Member
Danielle Wayne (@daniellegrl)
1 year 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

Christine V
Active Member
Christine V (@salty79)
1 year ago

Youre lucky to have a wife who helps you dress up

Katie Daily
Katie Daily (@kevin)
1 year ago

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

Dibbie Huneycutt
Dibbie Huneycutt (@dibbie)
1 year ago
Reply to  Katie Daily

Yes same for me

Fiona-Ann Moss
Active Member
Fiona-Ann Moss (@fiona06)
1 year 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

1 year ago

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

1 year ago

Good work Full circle, Nice to discover that fem’nin side about one’s self. I know what you mean about how you felt dressing up and I am glad you had/have that feeling. When I find the right place here, I will go into dept on how I started to X-dress.

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