View Full Version : Caught on Purpose?
Sasha_inside
09-23-2025, 10:45 AM
My wife and I were talking this morning and she asked me a question - Have I ever done something to get caught on purpose?
I had to think about it for a minute. Normally I make sure I don't show when I under-dress, but have been caught/seen/clocked before, many times.
But, on purpose, not that I could think of, other than when I went in to a store and talked to an SA about what I was looking for, or when I get bra fittings, dress fittings.
Has anyone else ever done anything on purpose to get caught? If this has been asked before, mea culpa.
sometimes_miss
09-23-2025, 11:12 AM
When I was a late teenager, I would do things like stay dressed for as long as I could, towards when the rest of the family would come home for dinnertime. I came very close to getting caught several times, including going outside the cellar to make it almost certain that I wouldn't be able to escape. But when my sister came home unexpectedly, I stripped completely and tossed my girl clothes in the washing machine and turned it on, and put whatever I could in that wash load (none of which was anyone else's clothing). All in the foolish belief that my crossdressing wasn't all that serious an issue, and that it would be easily overlooked because of all the good things about me. OH, how wrong I was. For, three decades later when I came out to my mom and sister, both were horrified; My mother dismissed the whole thing, ignoring that I ever said anything about it. My sister essentially cut off contact with me as much as she could, if I dared call her, she wouldn't say much, just answer questions with single word answers as much as she could, trying to get me to hang up the phone if it was a call, or leave if I actually went to visit her.
All because I couldn't bring myself to believe that crossdressing was such a big deal to so many people in this country. So if you don't think anyone cares, I would say you are wrong. The best we can currently say, is that people prefer the 'don't ask, don't tell' policy. They don't like it. So don't pretend that silence means acceptance. It doesn't.
docrobbysherry
09-23-2025, 11:41 AM
No. Altho, I came out to my immediate family after I was almost caught several times by my adult, live at home, daughter!:doh:
Staci
09-23-2025, 08:57 PM
My response is no. I never tried to be “accidentally on purpose “ caught. I couldn’t, and still don’t, see any positive that would come from the shock they would experience and then need to overcome.
Lacey New
09-24-2025, 05:57 AM
Aside from trying on a dress and showing the sales associate how I looked wearing it, no, I have never been caught on purpose. I have purchased lots of lingerie that was obviously a larger size and I?m sure that the sales associates probably guessed that it was fo me but I never came out and confirmed it.m
April Rose
09-24-2025, 08:42 AM
I got caught a few times when I was very young and too dumb to know better. Later as a young adult I pushed my luck pretty hard a few times, to the point where people might have figured me out. But I was never blatantly caught.
Nowadays, when I go out fully dressed(not often) I just assume people realize that I'm a male dressed as a female, so it's not quite the same thing.
JesseVF
09-24-2025, 09:26 AM
Looking back a few years ago I?m realizing I was actually trying to get caught by my wife as the urge to CD was becoming more intense. During our normal day of going out I would wear a bra and large breast forms - although with a loose black t shirt. It seemed very obvious but she never said anything. Finally I just came out to her. One of her comments was she should have known.
Raychel
09-24-2025, 10:22 AM
I don't think I have ever gone out on a mission to get caught.
Not mentally doing if for the sole reason of getting caught.
I have gone out at time just dressed the way I prefer not to get caught, but
more to step outside that box I have built for myself. I have gone out for
drive thru ice cream, And I have driven for a full day dressed. Not with the purpose
of getting caught, but more to push my personal limits. There were people that saw me
but that was just me living my life. Not really caring if they saw me. So is that caught.
Not in my mind.
Monique65
09-24-2025, 12:27 PM
When I first retired I wore my wife’s panties full time wanting to tell her without using words. When she finally found me wearing them (it didn’t take long), she suggested I get some of my own so I wouldn’t stretch hers. She even picked out several pair for me. Although we have never formally had “The Talk”, her acceptance of my femme side is quite obvious.
I've definitely never tried to get "caught" as such, but I have interacted with my brother on a social media account of mine that has several pictures of me dressed (including the profile pic), in the hopes that he would ask me about it, and save me some of the hassle of having to come out directly. However, to date, he has never mentioned anything about it, so now I'm just left wondering if he somehow never noticed, or he just finds it too awkward to say anything. At any rate, it was a pretty dumb way of trying to "come out".
SaraLin
09-25-2025, 05:56 AM
On purpose? NEVER!!
I have been caught a few times in something <um>inappropriate, but it was never on purpose.
Jillcder
09-25-2025, 07:38 AM
A couple times while fully dressed at home while my wife was out I thought very seriously about staying dressed and having her catch me in full Jill mode i never went through with it worried that it would be too hurtful for her. I often fantasized that if she caught me she would help with my feminization (dream on).
CynthiaD
09-25-2025, 08:49 AM
When I first came out to my wife, I put on a pair of black lace panties and told her I?d be wearing such things in the future. Her reaction was "Yeah, OK." I had expected something more angry, but no.
Then there was the time, more recently. I was in the emergency room with a broken hip and a broken shoulder. They had to cut me out of my clothes. When they cut off my shirt, I was wearing a white lace bra. I felt absolutely NO embarrassment. Quite the contrary. I felt an incredible surge of pride for them to see me wearing a bra. Although it wasn?t deliberate, I?m glad it happened. FYI they didn?t cut off my bra, even though I said the could. They managed to unhook it and take it off the regular way. I?ve still got it, and I feel a surge of pride every time I wear it.
I want to add, that the emergency room incident made me realize how proud I am to be a cross dresser. I want to be seen in female clothing, and I don?t care if someone recognizes me. Accepting myself as who I am has given me the self confidence I?d been seeking all my life. So, ladies, put on your dress an be proud.
I think I would have to be in a very bad way before I even let medical personal see what I'm wearing underneath my clothes, lol. I was in a motorcycle crash a couple of years back, and while covered in blood and in immense pain, I still went back home first and changed into male underwear before going to the hospital to get patched up.
OrdinaryAverageGuy
09-26-2025, 05:24 AM
The only times I intentionally got caught were with my wife. The first time she knew I had a skirt but didn't know I had lingerie and she basically dared me to shock her, so I did. This led to "the talk", which went well. Later on now and then I'd get something new that I thought might push the boundaries a little I'd push through the fear and let her "catch" me in whatever it was. Most of those times also went well and the couple that didn't got fixed a day or so later.
Taylor186
09-26-2025, 08:55 AM
I was in a motorcycle crash a couple of years back, and while covered in blood and in immense pain, I still went back home first and changed into male underwear before going to the hospital to get patched up.
LOL, I would do that.
That said, in the late 80s/early 90s I got into running (during the Lycra revolution) and all my running gear came from the women's side of the aisle. I was a solo evening runner and through the neighborhood I would travel resplendent in 80s colors and sleekness. I was wearing it presenting as a guy running. It was crazy when I think about it now, but the unisex look seemed right to me at the time. Was I trying to be caught? Not really. No one called me on it but who knows what they were thinking.
cosmolovesph
09-26-2025, 09:30 AM
I would say - Yes with underdressing and if you knew to look, you'd see my nylons underneath at the ankles and could have been with some shoes that would have leaned female but close enough to pass the unsuspecting eye) ... then there is the occasional wearing of pantyhose/sheer tights under shorts.... guessing not subtle but again, close to my skin tone so you have to look or also be a nylon lover like me!
Rare i will throw on a bra under a shirt but hey, at that point.... you were looking :)
Given today's styles and pushing the "boundaries" i am very subtle in comparison vs some others.
alwayshave
09-28-2025, 06:16 AM
I have never tried to be caught. I use to spent a lot of time attempting not to be caught.
Mercedes
09-29-2025, 05:25 PM
I was going to post my thoughts but Crissandra covered it very well. Lately I have been wearing a bra under my shirt when out for short trips, today I wore natural tone nylons under my shorts on a walk. Lately I have been feeling that I want Mercedes to be noticed, but not dressing to be caught. Some days, things are just confusing.
jjjjohanne
10-07-2025, 06:53 AM
I don't know what the definition of "caught" is...
I have never tried to be caught by my family. I have always had this steady push inside of me to do more and more risky things.
At first, it was to walk around the house at night in all women's clothing. I did not want the neighbors to catch me. I just wanted to get out.
Later, I ran around the neighborhood in order to exercise, like usual. But a few of those times, I did it with skin-colored pantyhose on.
I wore some of my mom's shorts and T-shirt in front of my grandmother once. She seemed to realize something, so I went away and changed.
blah blah blah...
I have gone out in public many times over the years. I have intentionally gone out in women's clothing where I would have to do normal things like grocery shopping, hair cuts, etc. I don't think of being seen in this mode as being caught, though.
So, no. I have not *tried* to get caught.
countrygirl
10-07-2025, 05:08 PM
No not on purpose, there have been times when items were discovered such pantyhose or other items. But never on purpose.
BLUE ORCHID
10-07-2025, 08:36 PM
Hi Sasha :hugs:, Just a Bra Fitting, But it was in a CD Shop.
Christie ann
10-07-2025, 10:27 PM
Caught on purpose or just not caring that someone knows
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