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.

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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20 Comments
  1. Rachel Doe Doe 2 weeks ago

    Enjoyed reading your article. Thank you,

  2. Leaona Seymour 2 weeks ago

    Jamie,

    Thanks for sharing. It was both entertaining and inspirational for others that are tempted to step out. You certainly have the self confidence and a great attitude towards being yourself!

  3. Trisha Foxx 2 weeks ago

    I really enjoyed reading your article. I can only dream of doing what you did.

  4. Steve Adler 2 weeks ago

    I have always shopped for women’s clothes while crossdressed and found that if you are a pleasant respectful customer the sales girls are very happy to help you.I think they enjoy the experience of working with a crossdresser and in the end,a sale is a sale for them! Shopping for women’s clothes while crossdressed is nothing to be afraid of!

    • Cary 2 weeks ago

      I agree too I have so much fun shopping at Macy’s for bras & panties & they have been very good to me I make sure to be very careful not offend anybody

  5. Keri Q 2 weeks ago

    I crossdress and of wear panties 24/7. Several years ago I began wearing panties to doctor appointments. A little awkward the first few times but he seemed to be fine with it. I don’t wear pink panties. I typically wear a basic white, sometime black and once a blue pair.

    My derm doctor is female and always has her assistant come in with her. This actually was more awkward for men than the male doctor. They always offer a paper shield to cover my mid section but by the time the exam is over I might as well as have had no shield. However, I have gotten used to it and they seem to as well. Nothing has ever been said. For the record I wear Vanity Fair full brief nylon panties. Also for the record it is kind of exciting when she pulls my panties aside just enough to see my butt or my legs. I have thought about wearing the lace trim panties Vanity Fair has and also wearing some of their pastels. Lets face it I am wearing panties so what is the difference.

  6. Amanda Lyn 2 weeks ago

    Great story thank you for sharing. I haven’t gone out in public as of yet. The closest I’ve been is going for a ride at night in my car that has black window’s. I know that really doesn’t count. Baby steps. I brought in the new year dressed up for the first time even being alone as I was. I made a promise to myself that next new years I would find a place to go and bring in the new year dressed up and in public. I’m tired of being alone.

  7. Milena 2 weeks ago

    Great! We can all use more positive experiences like yours. Thank you.

  8. Broll 2 weeks ago

    Thanks for sharing. I’ve just begun to wear my pantyhose and heels in the house when alone. I want so much to go out dressed, but at present time haven’t. I for the first time wore an outfit in front of my wife. She wasn’t appalled, but can’t say she really liked it either . We have since talked more openly about my desires. Hopefully, one day, I will have that opportunity to go out dressed. I am just now really opening up about CD that I have held on for so many years. Again, thanks,for sharing your story, it gives me hope.

  9. Jetta 2 weeks ago

    Thank you for sharing your experience, it is so encouraging to hear good experiences from others. Best of luck in your future outings.

  10. Jillian 2 weeks ago

    Nice story I liked it, I’m somewhat new to this but have gone out in public once and will be doing it more in the future, love the stories

  11. johnny queen 2 weeks 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.
    got ready to pay my bill.
    the owner said don’t come back that I was being nasty talk.
    I told the owner that she was being rude to me.
    her shop closed after that.

  12. Gord 2 weeks 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

  13. Jeannine 2 weeks 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!

  14. Maria Roberts 1 week 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.

  15. june meyer 1 week ago

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

  16. Elaine 1 week 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 which was so exciting …yay. I have developed my relationship with my dressmaker and she has even offered to give to dressmaking lessons , which I have yet to take up….but would love to. The traveling to and from the appointment is the most scary and I find myself driving so carefully so as to avoid and accident or being stopped by the police ….Also my biggest other challenge is finding a place to get dressed and do my make up ….which I usually do in the car which is not ideal …..but its a start and so exciting …..

  17. Jan 2 days 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 2 days ago

      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.

  18. Ilona 2 days 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.

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