10 Best and Worst Things About Dating A Crossdresser

10 Best and Worst Things About Dating A Crossdresser

I'm having a little...well, crisis is too strong a word, but let's say I'm having a bad patch this morning. I got my period back after many, many months, which not only signals that my body is getting back to "normal" but that Rose is beginning to wean. Since I have a love/hate relationship with breastfeeding, it's both a good and bad thing. The bottom line is that the hormone overload is making me emotional, it's making me second-guess myself, and it's making me neurotic.

One of the biggest areas for me to be neurotic is my relationship with my husband. "I like that dress" turns into "Why was he looking at her dress?" very easily. The simple answer is he's a cross-dresser, and he legitimately was looking at her dress. It's a passing phase, this paranoia, and it lasts exactly as long as my period, so at least I know where it stems from. To get through it, I like to "psych myself out of" it...so today, I'm listing the ten best and worst reasons why it's great to be dating (married to) a cross-dresser.

Sewing Machine

Image: isafmediavia Flickr


1. At least once, you will find clothes that are not your size and you will be sure he's cheating on you. You will only stop yourself from accusing him when you realize there's no way he's bringing a girl into that mad jungle you call a bedroom.

2. You are never going to know if you just caught him looking at a dress or an ass. Or both.

3. Sometimes he's going to look better than you. No, really. He has to do a lot more maintenance to show his feminine side, so while you're rocking your yoga pants and a boob-milk-stained tank top and haven't yet washed the spit up out of your hair (don't get me started on not having time to shower), he's rocking sequins and Ravishing Red lipstick. This can be fairly demoralizing, especially on a Monday.

4. It can get expensive. Now, money is already the number one problem in most relationships, so trying to fund a second wardrobe for one person in the relationship can cause some friction, to say the least. I recommend taking advantage of some BOGO sales to make it a little more fair.

5. You're stuck with a secret. This really is the toughest problem. Cross-dressers live with the secret of who they are until/if they ever become ready to share it with others. That means when you're "in" on the secret, you can't call up your bestie or your mom to complain that he's spending too much money on a second wardrobe and you're still wearing the underwear you had to cut to fit you when you were pregnant. (What? It happens, ok?) Their secret becomes yours. It can make you feel like you're lying to your loved ones when you answer their worried "Is everything ok?" with "Oh. You know. Same old." (Same old underwear!)

painted toenails


1. Clothes, clothes, clothes- Ok, Coffeeguy and I are nowhere near the same size, so I can't share anything that I don't want stretched out of shape--he not only is broad-shouldered, he's about a foot and a half taller than I am. His "gurl shoes" are size 12's, while mine are a puny 6.5 (unless, of course, I buy them in the kids department, where a youth 5 fits just fine--really, try it.) We not only like to look at pretty things together, we get to take advantage of a lot of the aforementioned BOGO sales without over-loading our sides of the closet.

Image: kthread via Flickr

2. Fancy Clothes- I know, I just covered clothes, but these deserve their own category. Most cross-dressers don't start out with an extensive women's wardrobe, so they pick pieces that are super-feminine to start. This means that every so often when the kids sleep over Nana's (they've never seen him "dressed up"), Coffeeguy will be sitting in the living room watching television in his prettiest outfit waiting for me to notice his fabulous legs. After a few months of this, it sort of forces you to re-evaluate your wardrobe. I mean, he's dressed to the nines. Why can't you wear your Calvin Klein cocktail dress to watch television on a Monday? I have found that it gives me motivation and opportunity to use my prettiest outfit, to feel sexy, and to (almost) never feel silly doing it.

3. Makeup skills- I have found that, in trying to help Coffeeguy with makeup, I have become better at using it myself. Men tend to have much bigger features to accentuate, so it's a lot easier to practice on them!

4. Better Sex- That's right, I said it. It really should be number one, but I didn't want to scare you off. Men who cross-dress want to feel pretty, just like you do, so they know which buttons are the right buttons to push. Ahem. So to speak. If maybe once or twice they dress up before-hand, the turn-on for them when you don't turn away, when you embrace them for who they are, is huge. HUGE, I say.

5. Closeness/Commitment- Most cross dressers don't start out a relationship by telling you "Hey by the way..." It's something they keep close, and they only share it when they think, "Maybe this one is the one." (Unless you're me. I don't think Coffeeguy realized I was the one until about eight years into our fifteen years of marriage.) If a cross-dresser has shared his secret with you, chances are he wants to share so much more. The seven years after Coffeeguy let me in on his secret were infinitely closer than the first eight--something I never would have thought possible.

So there you have it. Take it from me...the good far outweighs the bad. If you're not dating a cross-dresser, well, you can either use this list as a bargaining chip with your current boyfriend, or you can look around the office for the guy with the bright-colored shoes and start up a conversation.

www.suckathomemom.blogspot.com I'm a 40 something year old with two tweens and a new baby. This is my effort to keep my sanity after leaving the workforce, taking up breastfeeding, and managing the kids. I'm mostly failing at it.

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