First things first. I am in my fifties and dressing for nearly as long.

A woman at MAC describes me as JackieO, classy and sexy. I have only been going out in public a few years; I am me, but I try not to make people uncomfortable. No one I know at work or family know of my private time.

Recently, I went for my annual checkup with an MD I had never met. I had been to the office before and asked the previous provider if my dressing would be a problem and was told no.
Picture this, six foot, 200 lbs., long brown curly wig, black long sleeve body suit, pale pink power skirt from BCBG and black wedges. With my black and gold purse from Guess and big round shades I am feeling good. Was in the waiting room about an hour, but was basically ignored by the other patients.

Escorted to a room by a young girl in her twenties, some history and vital signs are taken. All is good. I ask if I was her first CD; she said yes, but no problem. I make a point of asking if people are OK, as I would rather leave than make things worse. She stats that she needs to do an EKG and I will need to remove my top. She offers a paper gown; I refuse thinking a bare male chest is no big deal. Then the fun starts. I have to lift my skirt to unsnap the body suit showing my bright pink panties. Next I undo my matching bra and lay it on table. I try to talk to the poor girl to ease her tension. There are 10 wires attached to my body and one goes to each foot. Now I have to get up off the table, lift my skirt even higher and pull down my pantyhose. It happened quickly, but this young girl is getting the experience of her life.

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Hear a knock on the door and the MD walks in. Now the three of us are standing there with me putting on my bra with my skirt hiked up, pulling up my hose, snapping my top and rearranging things. I make some comment telling her, yes a female MD, I am sure I am the talk of the office.

The doctor asks if she should step out and I figure as she has seen it all, it is no big deal. I make a few jokes, the exam proceeds and every now and then she asks about my dressing.

Towards the end we discuss a final evaluation, yes, every man’s fear. Again up comes the skirt, unsnapped, and this time, the nylons and the panties come down. I’m unable to see the look on this woman’s face but I can only imagine what is going through the doctor’s mind.

Then I get dressed again while she watches me and we talk.

My visit finished with me wiggling my hips around the office, giving blood and paying my bill.
Leaving the doctors office I didn’t want the make up to go to waste, so I go to an outlet mall. Something I have learned is that most people that shop at outlets are not from the area, and yes, CD do visit from other countries to cross dress while shopping.

Personally, I go shopping in Drab first and return in Drag if I want to buy something. I have been sold too many things on sale with out trying them on that recon and return is mandatory.

Arriving at the mall I walk into the closest store to get to the inside corridors intentionally, ignored as usual. Recently a white dress had caught my eye so the hunt is on. The sales girl is fantastic; while I try on the dress, she returns with a black jump suit. Stepping into the jumpsuit it just felt right. She says she actually likes the jump suit better and talks me into wearing it out of the store. Walking up to the counter a sales man compliments my look. While paying for the outfit a different sales person comes up stating that after seeing me in the outfit someone else bought one too. Quite the ego boost!

Now I originally came to the mall for something else, but hey – rock on. Acting as humble as possible, and showing extra respect, I now have a few sales girls that recognize me and are honest with what looks good and when to wear an outfit. I arrive at Dress Barn and my sales girl is there and is just thrilled at my jump suit.

This was perhaps my best day ever while crossdressing. I put in a lot of effort trying not to give CD a bad name. This was a big point in my life; I am hoping to give courage to some, offer encouragement to others and demonstrate that if you show extra respect your experiences too can grow.


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    jamie richards

    straight male crossdresser for 50 years looking for Miss Right.

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    5 years ago

    My comment is as far as it goes what to tell my psych nurse about my sexual desire to dress CD .being bi-pilor is bad enough. Antidepressants and such are common. But coming out CD she’s really going to think crazy. Perplexed what to do

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