My son is in second grade, and in most ways, he is your typical, overly active little boy. He does, however, have one small secret: he sometimes likes to wear his sister’s dresses or other more feminine clothes. He’s been doing it since he was old enough to start picking what he would wear and would occasionally select his sister’s clothes instead of his own. We did try to redirect him to more “male” clothes at first, but he was insistent enough — and thankfully, his sister was willing to share for once — that we accepted that he was occasionally going to be wearing dresses.
Now that [Son] is older, he has a vague sense that his choices aren’t “normal”, but he still likes to wear dresses on occasion and knows his family will love and support him regardless. Currently, he only wears dresses in the privacy of the house, on vacations far from those who know him, or otherwise on special occasions when it’s unlikely to draw too much negative attention. To be clear, we haven’t refused to allow him to wear a dress more publicly; we had a discussion with him, and this was mostly his decision. He likes wearing dresses on occasion, but it’s not a high priority to him, and he is more worried about the negative repercussions of friends and locals to his wearing a dress. For example, last Halloween, we suggested that we could get a costume for [Son] that included a dress so he would have plausible deniability when wearing it in public, and he told us he still wouldn’t be comfortable wearing one around friends, even as a costume.
It was several weeks ago when one of [Son]’s friends asked him if he wore dresses. Apparently, [Friend] had noticed him wearing a dress in our backyard and/or seen it through a window. I’m getting the details second-hand from [Son], and the hearsay isn’t clear on how the discovery happened. [Son] admitted it to [Friend], and [Friend] didn’t say much about it at the time. This didn’t stop [Son] from worrying that [Friend] would treat him differently or tell others. He was quite relieved when [Friend] didn’t bring it up again afterward.
So, you can imagine my own anxiety when [Friend]’s dad asked me at our local playground if it was true that my son liked to wear dresses. I gave as non-committal an answer as I could manage without outright lying, but apparently, I was still pretty transparent.
Father: “Oh, don’t worry. I already talked to [Friend] about privacy, and he’s promised not to go telling others, so [Son]’s secret is safe with us. I just wanted to mention that next time the kids have a sleepover, if [Son] wants to bring a dress, I’ll wear mine, too.”
It turns out that [Father]’s wife had once ended up with a dress that didn’t fit her but couldn’t be returned, so he had annexed it as his own. Every few months, he would wear it around the house just to get his son accustomed to the idea that men might like to wear a dress, or that someone who looks like a man may not be one. This was apparently part of a larger campaign to expose their son to as many different types of people as possible to encourage the child to be supportive of differences.
At first, [Son] was afraid to wear a dress openly in front of a peer, but after talking to [Friend] a few times and determining that [Friend] really didn’t care if he wore a dress, he finally decided to take them up on the offer. Last weekend, he wore a dress — one purchased just for him, not a hand-me-down from his sister — openly in front of a friend for the first time during their sleepover. It was also the first time he met another man wearing a dress. He loved it and is already talking about how he plans to wear dresses whenever he wants when playing with [Friend] from now on.
[Friend]’s mother has suggested that her son was potentially open to trying wearing a dress once, so there is even a possibility of an all-dress sleepover sometime in the future, depending on whether [Friend] decides he is open to the idea or not.
Given [Son]’s anxiety about others catching him wearing a dress, I’m personally glad that his first time being “caught” ended so well. I’m so thankful [Friend]’s parents for going out of their way to ensure their son would be supportive of my own.
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