Tuesday, September 22, 2026

Stuff 134: Caught

By JJ Atwell

Uh-Oh!

A fellow Femulate reader, Tia, wrote to suggest that some crossdressers secretly want to get caught. I had never considered that before. It seems to me that most of us go to great lengths to avoid getting caught. But the more I thought about her proposition, the more it seemed like a good subject for Stuff.

Please understand that I have never tried to get caught, so these are simply my musings.

Forcing “The Talk”

I wonder whether those who secretly want to get caught see it as a way to finally broach the subject with their friends or perhaps their significant other. If you are in the closet but wish you could talk about your crossdressing with someone, finding the right time to bring it up can certainly be difficult. Maybe some people need that extra push to start the conversation.

I’m not sure getting caught is a good way to introduce the subject, though. It seems to me that you would be starting off on the wrong foot—or stiletto.

My advice, for whatever it’s worth, is not to use this method to initiate “the talk.” Instead, find a quiet time when it’s just the two of you and begin a general conversation to get the words flowing.

During that conversation, perhaps mention that you have always found society’s gender roles interesting. Tell her that you admire the way she dresses and that you appreciate her femininity. Be careful not to make her feel that she is not “woman enough.” That may provide a springboard into the subject of crossdressing and why it interests you.

Or it may not. It really depends on the dynamics of your relationship. No, there are no easy answers here.

Loving Danger

Perhaps the desire to get caught is motivated by pure adrenaline—the same thing that makes roller coasters so thrilling. Some people thrive on that kind of excitement. Could the risk of being discovered provide a similar jolt?

Since I’m not that kind of thrill-seeker, I’m probably not the right person to comment further. But I would love to hear from readers who see it that way. You can leave a comment or email me using the contact information below.

Being “Forced”?

I also wondered whether some people want to “suffer the consequences” of getting caught. Perhaps those consequences might include being forced to remain dressed—or being told to wear something even more feminine.

By being “forced” to dress, they can sidestep the guilt that many crossdressers experience. They can rationalize that someone else is making them do it. That way, they are simply being good partners by complying with another person’s wishes.

These are merely possibilities that occurred to me as I contemplated the subject. I really don’t know the answers, but perhaps you have some thoughts to share.

I’ll Be Back

No, that’s not me getting caught in the picture at the top of the page. I had “the talk” with my wife long before we were married. The image was created by ChatGPT using a simple prompt.

As always, comments are welcome either here on the blog or by email at Jenn6nov at-sign gmail dot com.

JJ is always looking for more Stuff, so if there is something you would like to read about, please let me know!



Source: Ann Taylor
Wearing Ann Taylor


Camdenton, Missouri
Womanless beauty pageant contestant in Camdenton, Missouri, circa 1967

12 comments:

  1. love how you have raised the topic of being caught JJ. for me personally i was taking as much precaution as i could to avoid it happening but as time goes on & the excitement of dressing rises i took more & more risks when i was at my mother-in-law’s. i was probably guilty of not quite putting back in exactly the same place a garment of hers or not folding her underwear neatly enough. i know i laddered her stockings so i discarded them. as it transpires she had her suspicions & caught me full made up wearing one of her smart skirt suits. it was the beginning of our relationship that has now lasted over 11 years. she has been ultra supportive. so for me being caught was probably the best thing that could have happened. that all said my wife is oblivious to my dressing & the relationship i have with her mother.

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    1. Thanks for relating your experience Emma! A very interesting situation. I wonder if you've considered telling your wife. Could it be even more difficult when the MIL passes? Difficult choices indeed. JJ

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    2. JJ interesting questions you raise as my mother-in-law does want to tell her daughter before she passes on but i know that will be the end of my marriage. although my wife & i have not slept together for years it suits both of us to say we are married.. i would love to tell my wife if i thought she would be considerate & even entertain my dressing etc

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  2. Very interesting thoughts...I think my ex had an idea of my sneaks into her things,,and she did make small suggestions about shopping, but I never confessed and the topic dropped....Several years before however,,,I was apartment sitting for a friend, got into her bath powder, and got caught when another neighbor came over for a beer..He just said,,,you smell so good.....Trina

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    1. Thanks for the amusing comment Trina. Must have left you squirming while you drank that beer! JJ

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  3. There is a difference between the question of why a man may cross dress and what he may get out of it. Long before the advent of the internet or before cross dressing was even freely talked about in society, I got "caught." No I was not dolled up and she walked in on me. Our toddler daughter pulled open the bottom drawer of my armoire and took the lid off a box I kept my small collection of femme items. She yanked out a vivid red Vanity Fair bra. "The Talk" ensued. "Why would a man wear a bra when he has nothing to pack into it?" she asked. I gave her a BS answer that set her off. Something to the effect of wanting to get in touch with my feminine side. "Tell me about your feminine side when you can have a baby!, she threw back at me". Ouch! There was no coaching from any internet site or reference book. That was my independent thoughts. I told her "I do not know, why I do, what I do!" Realistically, why would a man dress as a woman and incur the negativity of societal scorn. This was the early 1980's, not now. Yes, there are personal differences among men that may differentiate one from another, but that does not answer the "why" question. I wear dresses only, never a pair of female pants will I ever wear. I love floral patterns, as well as tending our flower garden. That's my way of expressing myself. If and when you decide to have "The Talk," perhaps a little thinking before "getting caught" is worthwhile. Get ready for the onslaught of questions.

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    1. Your conclusion is well stated. I encourage others to carefully consider how they approach having the talk. Be ready with answers to the typical questions of "do you want to be a woman", "are you gay?" "will you transition?"
      As far as why we do this goes, I've long ago given up finding a reason other than I enjoy it. To me, that's good enough. JJ

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    2. A counselor for war related PTSD is of the opinion that each man and woman has some dna of the opposite gender in his or her profile, in some people it is more than others. Sort of dragging a cursor along a line. On each end is the 100% man or woman. When things get tough, how does one cope? I have many friends who sought relief with drugs and alcohol. Total destruction to the body. Me? Call it what you want, escapism? That cursor is dragged along that linear line and creeps into self-expression as those genes associated with the opposite gender express themselves.

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  4. Getting caught? That is so far in the past I barely remember. Years back I was a car dealer runner taking care of title applications at a county tax office in Texas. One fine Halloween I decided to go out in a dress and heels, sneaking behind my wife's back. She did not like that I did it. In time she grew to accept my dressing "en femme" except if I went somewhere with her.
    Now, presenting "en femme" is my default, whether I'm walking, shopping, doctor appointments, renewing my driver's license (gender designation as male), and even church where I doll myself up more.
    -John

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  5. Thinking back to college days,,one more episode of getting caught...Junior year I lived in an apartment, and so thought I could avoid any embarassing situations...wrong!! A friend came over on a Saturday to watch some game,,used the bathroom and came out confused,,,3 pair of pantyhose drying on shower rod! He was a psych major,,and also a senior,,didnt say anything then...Sunday he called, picked me up, and we went to open air type market,,,,hanging in the center of the ladies clothes,,a lovely satin and lace long flowing night gown,,turned to me and said,,,,you would look so nice in that,,scared me to death!!! He knew....Trina

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    1. Wow Trina, you've had some interesting "caught" interactions! The closest I ever had (besides a gf) was while working from home several years ago in my bachelor pad days. There was an insistent knock at my door that would not go away, so I pulled the forms out of my bra, kicked off my heels, pulled on a pair of sweatpants to cover my miniskirt and pantyhose, and headed to the door. I opened the door to a salesman of some type that I was able to shoo away rather quickly. I often wonder if he was there long enough to notice the bra beneath my graphic tee or my nylon-covered feet which I forgot to cover!

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  6. In a past chapter of my life, I let a gf "accidentally" catch me in her pantyhose. Her only negative comment was that, since I was several inches taller than her, I would stretch out her hose. Next chance I had, I bought her a replacement pair and a pair of the correct size for myself. I wore them a few times around her apartment with her and I was in nylon heaven. But we broke up before I ever had the chance to show or tell her I was wearing so much more than just hose around my own apartment.

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