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Help! My Son is a Crossdresser!

by Jessica De Leon on July 29, 2010

Have you recently discovered that your son is a cross-dresser? Perhaps he told you or you found evidence that would suggest this such as an article of clothing neatly folded in his bureau. Never fear, Jessica De Leon is here to help, so if you are feeling that you are drowning in a sea of uncertainty, grab hold of the life raft to the right as I pull you to safety.

For you mothers and fathers out there, I’ve got good news – your son isn’t a freak, pervert or degenerate. He’s just more expressive and creative than most men and should be treated as such. Any attempt to stunt his feminine side could have seriously harmful repercussions. Keep reading for some words of wisdom.

Advice For Dealing With Your Crossdressing Son?

This will not be your run-of-the-mill advice column. No, I will not be spouting off useless statistics nor will I attempt to get into the psychology of cross-dressing. You’d be better served finding that stuff elsewhere because I wouldn’t do a good job with it.

What this will be is a true tale of my life experience, in condensed form. I hope to serve as an example to illustrate that everything will be alright if you handle things properly. While I can’t speak for all of us, I do represent a significant portion of the crossdressing community.

Crossdresser Fears & Doubts

Be aware that your son likely wrestles with the concept of exploring his femininity and is probably experiencing fear, shame, doubt and embarrassment. In addition, it may be tough to acquire the clothing necessary for self-expression. This is where you can come in, not just in supplying cloth and linens but by being a rock-solid foundation in his life.

If you are there to comfort and support him, things will be a lot easier and he will grow up to be more well-adjusted.

Mamas, Don’t Let Your Babies Grow Up to Be Crossdressers

Just kidding. There is absolutely nothing wrong with cross-dressing and to lead by example I am going to list off all the things that make me a ‘typical’ guy in society as well as successes I have earned along the way.

  • I was always a stand-out in school – honors courses and good grades were commonplace during my school years.
  • Very artistic and creative – I enjoy drawing, singing, writing and painting.
  • I studied Computer Engineering in college and obtained a Bachelor’s Degree from one of the top Universities in the country. I went on to earn a Master’s Degree from one of the top private Universities.
  • I am married and plan on having kids in the future (dogs for now)
  • I have a great job which I love
  • I treat women with the utmost respect
  • I speak 3 languages
  • I have always been active in my church

“Guy Hobbies”

  • I love playing and watching sports – baseball, football, basketball, hockey and tennis
  • I enjoy “hanging with the fellas”
  • Action movies are among my favorites (Rambo, Demolition Man, Terminator)
  • I love dressing formally (tuxedos, suits, button-down shirts and dress pants)
  • My male wardrobe is robust and stylish
  • I love pizza, hot wings and cheeseburgers!
  • I once punched a gorilla (just kidding)
  • I burp outloud

Anyway, I hope this gives you a better outlook on your cross-dressing son. I have known that I was a cross-dresser since I was four years old. I have no intention of transitioning to full womanhood and neither do the majority. Some do, and this is okay as well, just not something that I am qualified to speak about.

Be well and keep this in mind – with unconditional love your family can deal with this and perhaps get some good laughs about it. Remember, positivity is key. Take care!

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{ 8 comments… read them below or add one }

Jessica Sideways July 29, 2010 at 7:46 am

I never thought that you burped aloud, Jessica. But then again, this quote from Dexter sums up that surprise quite well:

“My favourite serial killer is a lozenge eater? How human of him.” – Dexter Morgan

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Gaven July 29, 2010 at 9:04 am

Great post. You are dealing with a tough subject for parents to deal with, with class and a little bit of humor. I posted it on my Google buzz page.

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Penny July 29, 2010 at 11:27 am

These are all great points. The majority of us are productive members of society with interests and goals that extend BEYOND gender and stereotypes. All of the activities you mentioned are healthy and productive … well, with the exception of that Stallone thing =P

It’s a shame more parents aren’t as well-informed. I’ve read SO many stories of relationships ending over something as intrinsic to self as being transgendered. Maybe I’m biased but I do believe cross-dressers tend to be more creative and intellectually curious than most. Parents should ALWAYS help foster their children’s interests and help them discover who they are.

I bet you’re going to make a great father.

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Corey James July 29, 2010 at 5:00 pm

I think you’re wonderful, and a great role model. Although you’ll never get me into a pair of break-neck stilettos in public again. (I’m still in litigation from that car crash I caused – maybe.)

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Julie M Shaw July 29, 2010 at 7:43 pm

I just wish I could have shared this post with my mother – you express it beautifully, sweetie!

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Alice July 29, 2010 at 9:49 pm

First of all, congratulations for the site, it’s really entertaining and informative :D

About the article, well, I just wish I had found it earlier =/
I’m 16 year old, and when I decided to tell my mom about it she reacted really badly.

But life goes on! ;D

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Leslee July 29, 2010 at 10:52 pm

Interesting article. If one doesnt burp out loud does that create a gas problem. My mother knew all along and refered to me as her special child. Mothers are great.

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Jon August 31, 2011 at 7:57 pm

If only my mom thought like you. like Alice, i am rather young as i barely turned 18. she knows i cross dress but she hates it. i just cant bring myself to tell her that i rather enjoy cross dressing. she has even offered to buy me girl clothes but i refused because she would probably feint if i just asked to go shopping for clothes. i plan on talking to my aunt about it though.

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