I’m a 53 year old man and I enjoy dressing in women’s clothes sometimes. I don’t want to be a woman or to wear women’s clothes in public. I just like the feel of silky undies and other delicates against my skin. I find it arousing and sexy for me. I’ve been married but it didn’t work out (not because of this), and since then I’ve had one girlfriend. After about a year I felt ready to show her what I liked. She said it was disgusting and I looked ridiculous and we broke up soon after. I’m ready to date again and I’m wondering if there’s a good way to tell someone I like women’s undergarments, as I don’t want to be made to feel so horrible again.
Thank you for your experience and question. It’s not that uncommon for men to enjoy dressing in female underwear and outerwear. I get it! Women have gorgeous, interesting and sexy stuff whereas men are very limited in what they can wear next to their skin. There’s also the thrill of wearing something that you’re not supposed to wear. It’s kind of naughty and taboo. But because it’s taboo, many people struggle with the concept, let alone being faced with a man in suspenders and stockings!
It sounds like you had a very unpleasant experience with your ex, but it may not be that surprising if you simply appeared in lingerie, without giving her any warning. That would be a big shock for anyone. The men I’ve spoken to who enjoy dressing this way tend to opt for the “ambush” approach because they’re afraid that if they ask permission, they’ll be shut down before they get started. It’s true to say that in some circumstances it’s easier to say “sorry” than to ask for permission. But this is never, ever the case when it comes to sexuality, sexual behaviours/practices, or anything that involves another person. They have a right to be asked in advance, and they have a right to say “no”.
Difficult as it is, the most ethical way to approach this is to tell your date up front, that this is something you like to do and that you’d like to bring it into the bedroom sometimes. Let them think about it, research it and talk it through with you. If they decide you’re not for them, fair enough. But at least nobody got hurt, or shamed, and you didn’t take a person’s chance to give consent away.
You might want to try looking for dates on some of the kink sites such as https://www.fetishireland.com. Figure out how important this is for you, how much you need to bring it into the bedroom, if you need it to get turned on, and if you can leave it out of the bedroom some of the time. Once you know these things you’ll be better able to explain to others, and they’ll appreciate your honesty.
I have an amazing, clever, loving and creative boy of 10. He’s always loved dressing up in his sister’s clothes, having his hair done and putting on make-up. We’ve always allowed this at home but not beyond. Now he wants to wear girly clothes and grow his hair, and only play with girls, all the time. Mornings are becoming battles as we fight over what he’ll wear. We don’t want him to get bullied and want to encourage him to get past this phase so he fits in. How can we help him?
This is a great question as it becomes more common for people of all ages to express themselves in non-binary ways. The old binary explanation of gender (everyone has to be either male or female) is outdated and unhelpful. As science and medicine slowly begin to acknowledge what many ancient civilisations have always known: gender is how a person feels, and may not be dictated by their genitals.
It sounds like you’ve given your son a wonderful opportunity to be himself so far and that he really enjoys the freedom. And while for some kids dressing differently from the norm is a phase, for others it’s the start of a genuine expression of who they are.
The first thing is to figure out how you feel about your son continuing to dress how he wants. He may grow out of it, but if he’s insisting on dressing his own way, when it’s causing arguments, there may be more to it. Either way, learning all you can about all the possibilities, and then figuring out how you feel yourself, will help you to understand how best to support him.
Have several short talks with him about how he feels and why he likes his choice of clothes. Take him seriously and don’t diminish how he’s feeling. That in itself will mean a lot. Tell him how much you love him and how proud of him you are, and give him space to explore his feelings with you without being judged.
teni.ie has some good resources to help people understand transgender issues which may feel a bit full on at this stage. But as I’m writing this response I realise I don’t know of any good resource for parents of children who like dressing in a non-binary way, without it meaning the child may be transgender.
I wish you well and if you want to mail me personally for any ongoing advice you’re very welcome.