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.

EnFemme Style

More Articles by jamie richards

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    johnny queen
    johnny queen
    6 years ago

    I have a store called big sister’s closet. made friends with the owner an they let me try things. also a restaurant call Olio’s that let me come in dressed up. 71 years now look fair I haven’t change my voice yet most people don’t mind. one bad experience at a hair salon. the owner gets me a girl now at this point I look like a man. the girl starts to cutting my hair an talking about how I wanted it to be shaped like a female. just talking I made a remark about china geisha girls being man.… Read more »

    Gord
    Gord
    6 years ago

    Enjoyed all comments from everyone and loved there honest would love to be able to come out but no one in my family understands. Thought my sister would understand but got very upset and will not talk to me

    Jeannine
    Jeannine
    6 years ago

    I do crossdress at home and have ventured going for walks at night around the neighborhood. Full makeup wig etc purse and all. At first it scared me a bit but now not so much, no one could recognize me I think loll. And feels so good!

    Maria Roberts
    Maria Roberts
    6 years ago

    I think its all great. Thanks for sharing that with us. I have often wondered if the salesgirls dont have a problem with us. Most seem friendly, and in NYC, no problem at all. But now back in the Midwest, oooo,diffo deal.

    june meyer' class='avatar avatar-64 photo' height='64' width='64' />
    june meyer
    6 years ago

    sit in the backyard in the summer in a dress and heels

    Elaine' class='avatar avatar-64 photo' height='64' width='64' />
    Elaine
    6 years ago

    Oh my goodness I cannot believe that I am writing this ….my first going out experience was when I found a dress maker online and made an appointment to see her, explaining my situation to her in the email. Well I got all dressed up and was so nervous, but the appointment went so well and she was so sweet. She took my measurements and we planned a new dress which took a couple of weeks. My second appointment was more fun because I got to try on the new dress, and even needed help to get into the dress… Read more »

    Jan
    Jan
    6 years ago

    Loved your story, wish I could have the nerve to do what you have done. I dress and go out. I go in stores and I have gone out to eat. I hope one day to go to the doctor like you have done.

    Ilona
    Lady
    Member
    6 years ago
    Reply to  Jan

    Hello Jan. I have asked reception staff whether I can wear a skirt or dress for a medical appointment. For some examinations, it is better to wear a skirt.

    Ilona
    Lady
    Member
    6 years ago

    When I was in hospital last year, I decided to ‘come out’ to staff and chose to wear a nightdress rather than pyjamas. Since then, I have attended various hospital appointments en-femme and have been accepted by medical staff without complaint. It has given me a feeling of freedom and it is now a long time since I wore male underwear or socks.

    Renee T
    Renee T
    6 years ago

    Beautiful story Jamie. It’s wonderful to not feel ashamed to go out dressed the way you feel. And to have the doctor and all of the sales girls treat you in a very respectable way. I have been shopping a few times (not dressed femme) buying clothes or makeup for myself and I have had all different kinds of reactions. Some good and some a little stand-offish. Glad your experiences were welcoming

    Patricia Marie Allen
    Lady
    Active Member
    6 years ago

    Hi, I’ve been under-dressing (bra with small forms and panties) for years. I used to worry what my doctor would think about my transgender expression and kept that one pair of men’s underwear for doctor visits. Then I ended up with a gallstone and needed surgery for that. My employer insisted that I have a release from my doctor before coming back to work. Well, I thought it would be a simple in and out and didn’t bother to remove the feminine underwear. The nurse took vitals and then the doctor came in for an interview. She asked if I… Read more »

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