Tell one person you crossdress today

When Michelle first emailed me her story she prefaced it with a sentence that many of us can identify with. She said:

I always saw that “Share your success story” thing in the emails and thought “I wish I had a success story.”

I do that myself sometimes. I look at the other successful, beautiful, confident transgender woman and sometimes think to myself, “I wish I was like them. I wish I had a taste of such success.”

Michelle, thank you for sharing your success story, and for showing us that each of us can achieve our own success without needing to compare it to others.

If you’re like Michelle, and have been wondering whether you have a crossdresser success story to share – take a moment to think of any positive experience you’ve had crossdressing, and share your crossdresser story.

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Meet Michelle

I have been going by Michelle online, but have also recently adopted the name Rachel, as it is more similar to my own name (Richard).  I started wearing panties in high school, but since I didn’t have sisters, they were what I bought for myself.  I gradually added bras and slips to my collection (which actually got purged on a regular basis), and started trying on skirts after I got married (over ten years ago).  I bought my first new dress for me five years ago (actually tried it on in the shop and had the lady make a few alterations for me) and currently own a few skirts and other ladies clothes, including some heels.  I rarely get a chance to dress, and even that is almost all at home in the privacy of my own bedroom (I can’t even walk around my own house because we have kids).  (Wow, I can really ramble sometimes — anyway, on with the story.)

Michelle’s Crossdresser Success Story

I recently started seeing a therapist to help me deal with my inappropriate reactions to stress (yelling at the kids, and inappropriate online activities).  We discussed my crossdressing and I ended up going to the mall to visit a lady I had met in a bridal shop before buying something for my wife, and had also developed a business relationship with.  I asked her if she knew that I was actually sort of shopping for myself as well, and she said she suspected but wasn’t certain.  It felt really good to have a real live person know about me and not just a random sales girl at a mall that I would likely never see again.  I have had several shopping trips that were somewhat successful in terms of me being honest about the intent of my purchase.

Yesterday’s story starts somewhat a few weeks ago.  I was getting ready to change the oil and for some reason ended up wearing a skirt under my coveralls instead of pants.  Then I realized I could probably get away with that with some of my looser fitting casual slacks as well.  So yesterday I wore a skirt under my pants as I went to the dentist.  Then after the dentist, I slipped my pants off in the car and went shopping at a bridal store in a skirt.  I didn’t have the awkward moment of, “It’s not for my wife, it’s for me.”  It was great.  I had a really good time shopping and the lady was very nice.


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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Lynn Jones
Lynn Jones
14 years ago

> I wish I was like them

I think that’s what keeps us moving. What drives us to do more. We want more than we have now. It’s not just a TG thing, but a life thing.

Sometimes, tho, it’s good to take your foot off the gas and drift to a halt. Pull over and enjoy what you have got, rather than speeding on to the next ‘must have’.

I think Michelle’s story shows real bravery.

8 years ago

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7 years ago

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7 years ago

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