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I've been caught crossdressing numerous times times in the past . Weather it's bad luck , poor planning , bad judgment ignorance or just coincidence .
I've never been caught by a family member or friends yet thank God .
I've been caught by motel /hotel cleaning staff , store workers , delivery men ,office receptionist and neighbors .
My first time was at a cheap road side motel . In my early twentys,I would rent a room for 2 nights so I could spend the weekend dressed . Usually Friday and Saturday . On a Saturday morning I was getting dressed there was a knock on the door a second later the door was open . I was sitting on the edge of the bed in a short skirt , sweater and pumps . No makeup or wig. The cleaning lady ,probably as embarrassed as I was apologized and left. Why I didn't have the chain on the door ? I don't know .
Awhile later at a different motel on a Friday night I was all done up in my LBD heels , and stockings . Taking time with my makeup , I was feeling good . Next to the motel was a liquor store . I decided to go get a bottle of rum to mix with the coke I got at the vending machine . I walked next door to the liquor store and got a pint. After the cashier gave me my change he said " pal this isn't the best place to be dressing like that " I hurried out of there as fast as my heels would let me . After calming down I changed into a little pink and white nightie , drank the rum and coke and went to sleep . The next morning at about 10:30 I was awakened by a knock on the door and again the door was open . The cleaning lady saw me and said " at least let me give you some clean towels " she came in , took the dirty towels and left clean ones. Before leaving she said " have fun today " Thru all this I just sat there and said nothing . 0 for 2 with the door chain .
A few years later I decided to go to a therapist to find out more about my crossdressing . The therapist suggested that I bring an outfit I could change into for our next session . I picked a conservative knee length dress .,black panty hose and 2 inch heels . When I arrived at her office she said she'd have a cup of coffee in the break room while I changed . Just as I was finishing up , adjusting my wig in the mirror behind the door , the door suddenly opens. There's me and the receptionist face to face . She apologized and said she didn't know anyone was in this office having seen the doctor in the break room . After the session as I was leaving she apologized again and said " see you next week " with a big smile .
This next one happened only 3 years ago . One night I couldn't sleep so I decided to do some house work . I like getting dressed when I do my cleaning . I wore my short denim skirt , a floral top and sandles . Eyeliner and lipstick was all I wore . I folded my laundry , cleaned and moped the bathroom and the kitchen . All done except the trash . At 3:00 in the morning I figured it was safe to go to the trash can in the driveway . As I approached the cans here comes Sandy . Sandy my neighbor is a nurse and works crazy hours . As she pulled into her parking spot I was engulfed in the head lights . I quickly dumped the trash and went back inside . A few days later I saw Sandy and wanted to explain but she said " don't worry about it , if that's what you want to do Do It " she also complemented my blouse
All these encounters now seem harmless but at the time they were not . I think back and wonder " did I want to get caught ? "
Thanks
Xoxo
Linda Taz
Hi Linda, from the sounds of it your not trying to get caught, but it's inevitable these days that people are going to see you dressed. Whilst I was a private dresser I was seen multiple times. I think it's how we react to being seen that matters. I think society is getting much better these days do it matters less if we're seen by strangers.
Love Trisha
Thanks Linda for sharing these stories!
Must not have felt good at the time. I haven't been caught yet… not that I know of.
Love and hugs, Stephanie 💖
Statistically it's bound to happen sometime.
Last time it happened to me I was on holiday with the SO for a few days overlapping a music festival. We had rented a private cottage. Madam had an afternoon booked in the local spa and I thought I'd have a Jen afternoon enjoying the garden on a sunny day. Relaxing in six inch heels and a LBD I had just settled down in the summer house, with a long drink and a good book, when the gardeners arrived unannounced to do some emergency work on a tree (there had been high winds)! I was like a rabbit in headlights, not knowing whether to run for the house or just hide! I decided my killer heels would have cut the lawn to pieces, or I'd break an ankle in the attempt to make the house. So, I resorted to keeping my head down in my book, a polite wave and fervent hope that they wouldn't try to make conversation. Sod's law but they wanted to apologise for the interruption to my afternoon!
Goodness knows what they made of me. As a small mercy, the music festival does attract a lot of alternative types to an otherwise quiet backwater, so it can be a bit more metropolitan than other rural areas.
I certainly didn't want to be caught. The adrenaline buzz was sure for real!
However, reflecting on it, there is some part of me that would be happier if my secret was more broadly known and accepted.
Isn't great just thinking back to some of our near misses ? Always thinking what if.What if one of those cleaning ladies screamed or the receptionist laughed or my neighbor started nasty rumors
Those times getting caught was always scary. But afterwards and reflecting on it, they were some of the most exciting of my dressing experiences.
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The thing is, though, that the cleaning lady didn't scream, the receptionist didn't laugh and your neighbour didn't get nasty.
Maybe, just maybe, society is broadly more accepting than we think and maybe, just maybe, a lot of the worry over non-acceptance is simply our own guilt and fears. Not that that thought is going to encourage me to pop out to the local store in a Hell Bunny dress and some stiletto heels!
I'll answer you privately.
Diane
Hi Linda Jen wrote: However, reflecting on it, there is some part of me that would be happier if my secret was more broadly known and accepted. Isn't that the truth Stephanie
It seems like the Universe is determined to put you.😊
Hi Jen. I’ve had a few near misses, and one caught. All by family members. A couple of times my adult children (they don’t know). showed up and I barely made it to change. A few times my wife (who knows) came home early. I got changed a few times but the last time I had a skirt top tights shoes and all. Got to the bedroom to change but wasn’t going to happen before she got in the house so I just went and sat in the living room and said hello. :). She knows I dress but doesn’t like it. But to her credit( and mine) we sat there and talked normally about her day. I stayed dressed through dinner. It was a breakthrough. She still doesn’t approve but we are working through it. And yes I agree. Sub consciously I think I want to be caught.
Hugs...Billie
My wife knows. My son at least suspects, but my wife and I agree he doesn't need to see that, at least not yet. I'm fairly sure at least one of the neighbors knows, is bound to have seen me at some point, it's a decent way from the house to the car, overlooked by two other homes.
Yesterday I had some time to dress with the wife having the son out of the house for a few hours. I ended up spending a lot of time on the porch reading, and I do think that part of me wants to be seen by someone. The girl who does my toes knows, so that's nice. I think we all want acceptance.
Bridgette
Speaking of “wanting to get caught”. I have such a desire. I want to leave a pic of me fully en femme open on my phone and have my wife “happen” to see it. I’ve seen advice given to NOT do this. Just wondering what other girls opinions might be. BTW. This is why I love CDH.
Hugs...Billie
Linda seen on the News about your story being told now 24/7 hehe just kidding been caught many times sometimes on purpose other times accident.
hugs
Donna
Almost caught, once. My elder son came by once, sooner than expected, and I was in the middle of changing. When he rang the doorbell, I had to kick off my ballet flats, drop my skirt, pull on a pair of jeans and wipe my makeup with a couple of paper towels before I could answer the door. I do want to be caught, but I promised my wife to keep Bettylou hidden from the kids and her friends; otherwise.....
I'm sure the neighbors have seen Bettylou put out the trash or feed the stray cats which hang around. Doesn't bother me at all.
