If you were to get caught what would you like to be wearing and by who

And how would you hope this event would play out ??

I would hope to be caught by a girlfriend, or female roommate in her frilly babydoll nightie and matching panties ! I would hope she would get a playful laugh out if it and tease me then turn a bit dominant and make me wear some of her other items. Starting with a satin bra and panty set, full lacy slip, pantyhose and Party dress !

I think being caught by my crazy mother would be the worst ! If she caught me in any of my sisters things she would have probably dressed me in one of the girls frilliest dresses and make me play with dolls with my little sister. She had threatened many times doing this too me when I acted wimpy or complained how she favored the girls. I also heard my mother one night at our vacation house basicly forcing my dad to wear one of her nylon nighties since he forgot to pack Pjs ! She was howling with laughter and teasing him to death ! Since she offered several times dressing me as a girl for Halloween, puting boys into girl clothes was aomething she really enjoyed !

I would either like to be wearing a wedding gown if I were caught by my wife, Or be wearing a nuns habit if caught our local pastor. Or, be dressed like a naughty school girl if caught by one of my old teachers. Lol. The possibilities are endless!

A dress and heels (modest and typical for how I dress) - anyone knocking on my door (I do not hide when surprised)

Another thread for you to get off to... The pattern continues.

Have to agree with Karen, so many options... :)

I will share a quick related story while I'm here.
In high school, I used to steal my sisters panties all the time.
At that point, I mostly I just slept in them. I over slept one morning and my mom ripped the covers off my bed to get me up.
There they were, pastel yellow bikini briefs.
She never said a word, but a week later all my tighty-whitey's were gone, replaced my men's bikini briefs in a variety of pastel colors.

And before you ask, absolutely, I still stole my sister's panties. They were panties, after all. LOL

Ohhh! And my 10th grade English teacher catching me wearing her lingerie in class! She was a border at our house a couple years before she was my teacher and I used to borrow her lingerie when she was out of the house. Made taking her class more interesting g k owing that I may have worn what she was wearing that day. Lol.

My wife knows, is supportive, and has seen me in all of my things either in person or in photographs. My two adult sons do not know, nor need to in my estimation. However, if they ever do I would hope to be wearing my navy blue/lace a-line dress with my black patent leather heels and gold necklace. It is my favorite and I think looks the best of my outfits. I would want to feel comfortable and look good as I would have a lot of 'splainin' to do.

I would love my wife to catch me wearing my prettiest dress, heels with my best makeup job. I often wonder what her response would be after I present myself and say well you caught me how do I look!

All tho to some here this subject may be arousing? It's not one of my fetishes!:doh:

I was almost caught by my adult, live in daughter a few times and dressing became so stressful for me I gave it up for a time!:thumbsdn:

Until I finally had THE TALK with her!:sad:

I'm still a closet dresser but I love to be seen out and about. But, NOT anywhere near home by anyone who knows Robert!:eek:

As a child, panties and girls clothes were a punishment for bad behaviour. As a teen, I believe my mum knew what I was doing, but said nothing. She set aside items I usually wore, making sure those items were kept washed and clean.
Worst case would be getting caught by one of my adult sisters. I can't think of a best case situation. My wife knows, so I am not hiding anything from her.

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Originally Posted by docrobbysherry

All tho to some here this subject may be arousing? It's not one of my fetishes!

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So maybe dressed and tied up and then caught?

I agree with Charlotte it is a bit weird. I think the poster is getting off.

My luck I would be caught by the paramedics after I did something stupid dressed,like falling down the stairs in heels and had to call 911.

My wife knows, my mother knew. I only was afraid of my father knowing.

Have u been peeking at my Fetlife Page, Karren!?:daydreaming:

Best case would be caught in a skirt and cami by a friend who would not only tell me I look great but say "that looks really comfy, don't suppose you have another skirt and top for me?" while handing me a beer.

Second best case would be the same friend saying "You look comfy, who cares what you're wearing?" while handing me a beer.

Whoa, Robbie, I can attest to part A and Part B. First Part B because that came first.

I am sure my mother knew I was wearing her clothes; how else would her sole black bra end up with a broken shoulder strap? Or her can of hair spray kept getting empty. But, there were two sons in the home; one fourteen months older than the other. I was the younger and the one who was always in disfavor because as the second born I was suppose to be a girl to round out her "perfect" family; husband, wife, older son and younger daughter. Surprise! My father's sperm thought otherwise. My parents tried the hardest to catch me in the act. There was no privacy taking a bath. Many times my father would bust into the bathroom when I was bathing to make sure I was no "pleasuring" myself. Once my parents went out for a stroll. That was my opportunity to strip down and don my mother's sundress which hanged in the closet in my bedroom. I watched intently for their return. Yikes, I screwed up. They took the elevator to our sixth floor apartment faster than I anticipated. The key was in the door. The door was stopped from opening because of the security chain. My father tried shouldering into it to break the chain. It held. I strip down and redressed. Fortunately, it was summer time so I wore minimal clothing anyway. "What were you doing?" The inquisition ensured. I survived with a good line of bull and my secret remained a secret. I was seventeen.

Part B, When my wife and I were newly married I bought her a white ankle length peignoir. It was 1971. I knew nothing about women's sizes. She was five foot two and 115 pounds. It was a medium and it swam on her. She had a good chuckle about it. One night I had gotten out of bed for a drink of water in the kitchen. I loved nylon and slipped it over my head. She walked in on me. "Why are you wearing my nightgown?" I explained I loved the feel of the nylon. I still do. We ended up buying several nighties for me, as well as some hosiery. It was "kinky" bedroom play which had benefits for both. It was no until later that it hit the fan when a vivid red Vanity Fair bra was discovered. Then, it became more than a little "kinky." Cross dressing was shut down. Fast forward to four or so years ago. My wife was clearing out dozens of nighties from decades ago, vintage. The pile was on the bed. She told me to take whatever I wanted; knowing the white peignoir was the only nightie that would fit. I took it. We sleep apart due to medical issues; snoring and bad backs. I am able to sleep in a nightie and I do wear that fifty plus white nightie some nights as well as a favorite pink peignoir of the same vintage we bought together.

I?ve thought of this, it will probably happen at some point. I?d own it, I?m comfortable in my own skin. But I wouldnt bring it up I?d let them either acknowledge or ignore. I do have a few close friends I?d wear anything around but they arent local. In public I dont dress to pass but leggings or a skirt are definitely seen as feminine.

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Originally Posted by StephanieCD

I agree with Charlotte it is a bit weird. I think the poster is getting off.

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I don't want to look like I am picking on somebody or trying to bully somebody, but I think that I have a right to call out behaviour that makes me feel uncomfortable, in the same way that somebody posting on image threads could make somebody uncomfortable and should be called out.

I specifically commented about "the pattern", because without needing to go a view their started threads, I already knew who the poster was and what the content would be like.

Did you/If "THE SCENARIO" with womens clothes, how would "WIFE / GF / SO / FRIENDS" react?

Yes, I went full stalker and looked at the started threads, and of the relevant ones on the first page:


If you were to get caught what would you like to be wearing and by who
If you found in the guest room you were staying in several Girly Bra and Panty sets
Do you find it fun to watch yourself wiggling into women's clothing ?
For Halloween did a Female or your Mother ever offer to dress you as a Girl
How do you think you look in your sexy Bra & Panty Sets? And has Your SO ever
Did you ever put on something So Girlie that you got a bit of a laugh out of it
Did you Ever Put on a Gals Dress or Lingerie to kind of test the waters ?
Lots of Little Girl Adult "Sissy" Dresses for sale online! HOw would your S.O. React
For fun or to help Would you or have you modeled a Dress If your SO or Gal Pal asked
Were you ever in a situation where you could try on a Bridesmaids Dress ?
Trying on Relatives Dresses so much Fun ! Would they have really cared ?
Have you worn feminine items that your S.O. has not? Or worn some more often then her
Is Dressing as a Bride as fun as it looks ? And How do most wives react to the Idea
I surprised Her by putting on one of her lacy Maidenform Bra & Panty Sets
If My Mother had Caught me as a boy Crossdressing I think she would have ?





The aim and objective is consistently to hear of a scenario where a female finds a male, or potentially finds a male, in a compromised position, and the OP wants to hear some story about what happens next.

Literotica is the place to search for sexual fantasies and role playing scenarios like this, NOT the members of this forum.


MODS: Feel free to take this to PM - I have seen one of these threads get binned after I called it out probably 2-3 months ago. I'm not trying to cause trouble or an issue here, I am just calling out that I don't feel comfortable with the behaviour on this site, and I am NOT the only one (with apologies to StephanieCD who I have quoted and inadvertently highlighted - you are not the only person to have sided with my opinion)