This article will address two topics that may be interconnected. Perhaps someone has dressed you, or wanted to dress you as a woman or girl? And maybe you didn’t accept it, but ended up regretting it? … or not!
Sometimes, people don’t introduce crossdressing into their lives themselves – it is introduced to them by other people. Imagine some hypothetical situations.
— When you were a child, your mother, sister or someone dressed you as a girl. Whether it was to take you to a party, as a punishment, for a bet, or just for fun. Or maybe you, now grown up, are a police investigator and your superior tells you to disguise yourself as a woman to work on a case. You enjoyed the experience, but you never admit that to anyone.
— Your school had a “Womanless” event – or your friends simply decided to have a “sex change day” (where teenage students dress up as the opposite sex) and you were invited to participate. But you refused, even though you already like crossdressing.
— Someone wanted to put you in some lingerie: your mother lent you a pair of your sister’s panties because all your underwear was still in the wash; or when you were a teenager, she suggested a bra for your gynecomastia; or, years later, your girlfriend or wife asks you to try on some of her intimates because she has a fetish. And you come to a standstill: boys and men don’t wear lingerie.
But is masculinity so fragile that it can be compromised by simple items of clothing?
You may never have even thought about wearing something of the opposite sex until you were presented with one of the situations described above. You may like it and repeat the experience (even if secretly), or not. You may simply refuse out of fear and shame. Another situation is that you like crossdressing, but refuse to participate in events with the theme, out of fear and shame of doing it in public.
Generally, mothers who dress their sons as girls for parties, do not expect them to like feminine clothes so much that they would want to dress up at other times. Perhaps mothers who turned their sons into princesses to win a charity Womanless would freak out if they caught them wearing feminine things in another context. The “problem” is that it was probably the mother herself who made her son discover this pleasurable hobby of wearing things of the opposite sex, when she put him in a dress, jewellery, shoes, makeup and even lingerie, so that he could win a simple contest. But the boy likes the experience and wants to do it again – after all, Womanless parades do not happen every day … but he needs to hide it, even from those who encouraged him to do it.
But what if you refused to participate in a Womanless parade or a school gender-reassignment day, when even the bullies in class dressed as girls?
On the one hand, you missed out on an experience that you might have enjoyed if you had never done it. Or worse, you missed out on an experience that you know you would have enjoyed, and that you could do in public without being frowned upon by society. But there is another side. You might have been ridiculed by the bullies (even if they were also dressed as girls). Plus, today we have the internet and social media – it is normal for teenagers to post pictures of events they attend and things they see. Imagine, years later, your prospective girlfriend or boss checking you out online and finding pictures of you from 10 years ago, wearing a dress, wig and bra. That could be embarrassing.
Isn’t an easy choice. Either you miss out on enjoyment, possibly of something really amazing, or you could deal with a future problem.
In addition, there is the issue of masculinity. A boy may refuse to wear his sister’s panties even if his own underwear is dirty, for example. Underwear is for boys, panties are for girls. A teenager with gynecomastia may rebel if his mother or sister suggests he wear a bra. Bras are for girls. A man may even be suspicious of his girlfriend’s or wife’s intentions if she asks him to try on panties during an intimate or fetishistic moment. He may think that trying on panties is an attack on his masculinity.
But is someone’s masculinity so sensitive that it can be shaken by a simple piece of clothing? Not a real and strong masculinity; that wouldn’t stop someone from having this new experience.
On the other hand, if your sister finds out that you wear panties, she may use this against you. If you accept your wife’s challenge and start wearing panties during intimate moments, she may use this to attack you when your relationship is going through a difficult time.
There is no easy answer.
If in the past someone dressed you as a girl and you liked and enjoyed the experience, that was amazing. If in the past someone wanted to dress you as a girl or woman and you didn’t let them, even though you wanted to or were curious, don’t blame yourself. You had your reasons – which, considering the society we have, are more than fair!
But remember: it is not a simple piece of clothing that defines your masculinity or who you are.
Do what makes you feel good.
– Have you ever been dressed as a woman or a girl by someone else?
– Have you ever had the opportunity to be dressed as a woman by someone, but didn’t accept? Why?
– If you could go back in time, would you now have accepted being dressed as a woman where you had previously been invited but refused?
Sincerely,
Marie Claire
More Articles by Marie Claire
- How to retire male underwear and pyjamas and replace them with lingerie?
- The meaning of your female name
- What I Learned from wearing Bras
- Becoming a Princess without having their Bank balance!
- The Man’s Lingerie of the future…
Latest posts by Marie Claire (see all)
- Have you ever been dressed like a girl? What if you had accepted? - April 9, 2025
- How to retire male underwear and pyjamas and replace them with lingerie? - February 17, 2025
- The meaning of your female name - January 7, 2025
- What I Learned from wearing Bras - October 21, 2024
- Becoming a Princess without having their Bank balance! - August 29, 2024
Funny, I thought we all looked at those things in the Sears catalog; albeit not for the same reasons….
Very interesting!
I do have vague memories of being dressed by my older sister once, maybe as a Girl Scout? I so wish I’d been more into it then….
Have you asked her yet?
Alas, I never seem to get the opportunity to have that heart to heart talk with her. She’s some 900 miles away, and life has been getting in my way each time I plan on a visit.
I grew up with an older sister. I recall somehow asking her to try on her panties when I was younger. At one point I do remember asking to try on her pantyhose when I was in high school. I whenever I faked sick for school I’d dress in her clothes. It just felt so right. So off and on it’s been a lifelong pleasure and passion
How did your sister deal with this?
Thank you so much for sharing your experience!
❤️
as alluded to by several others-decades ago every thing femme was looked upon with disgust by most men.once my 2 aunts were gathering things for the salvation army and suggested that I try on their old confirmation dresses. I wanted to badly but my dad was around and he would have erupted.a number of years later I sort of suggested we try an opposite sex couples Halloween outing and 4 of us did so. My 1st time dressing up. But after about 1 hour in a dance club someone entered that I knew and I felt so guilty that I… Read more »
Thank you so much for sharing your experiences!
I know many of us have had that experience of a female dressing them up. I never experienced that but certainly wish that I had. I still like that today! I don’t know if by having a lady dress me. it relieves me is the want/desire to dress or minimizes the guilt of wanting to do that
You have a point!
I was never dressed, unfortunately. But when I was around 12 or 13 I remember telling a friend a made up story about me wearing a female swimsuit so they let me in the dressing room with my mother at a health club. Without any kind of sexual drive, somehow I convinced him to wear swimsuits together in the bathroom of my house. I still can’t believe I did something like that! Perhaps I triggered crossdressing in my friend, or maybe not. I’ll never know.
So interesting
Not so much as actually dressed, but perhaps a subconscious desire to do so, that sprung from my father teasing me at a very young age, by saying he was going to “buy me a pair of pink panties" Perhaps he said it enough times to make we want to try some on? It may have been the genesis of what it now some 70 years later, “the woman within me". Plus of course from early teens i was “into" my mothers lingerie whenever my parents and my younger brother spent winter weekends at our seaside holiday house. “There was… Read more »
Oh I forgot, guess what colour panties I’m wearing as I type?… Pink of course….
So interesting. But why did your father tell you that?
Hi Marie, Thanks for the response. I think it was just his idea of a tease..It all went very “boob shaped" in my teens when one weekend when “home alone" some relatives came to check on me and I was caught red handed.in one of my Mum’s evening gowns. Dear old typical 60’s Dad “had the talk" with me and told me that if I kept up dressing in Mums clothes, “the Boys on the Pub would call me a Queen". Of course this exalted group was the font of all1960’s Australian “wisdom and knowledge" so I was supposed to… Read more »