I never would have thought I’d be posting an article of this nature, but the situation amused me so much that I simply could not refuse. Names are changed here to protect the innocent and potentially embarrassed.

I have a friend named Ellen who is married to a man named Keith. They’ve been together since high school and love one another very deeply. Best friends is too loose a term from them – they’re one of the few couples I know that I can honestly say are soul mates. That doesn’t mean that Ellen and Keith don’t have their issues, but they DO usually work them out with a little bit of talking. And cookies. Ellen loves making cookies. I’ve yet to go over to that house without being greeted by cookies. It’s fantastic.

Several months ago I received a call from Ellen. “TheWife,” she said to me, somewhat annoyed, “I need to talk to someone who’ll understand.”
I was elbow deep in laundry at the time so I happily abandoned the chore to chat with her. (Hey, I never said I was a terribly RESPONSIBLE person.)
“So you know how I like (this particular fantasy) right?”
(A quick note on my friends and I. Before some of us moved and our group ended up being scattered to the four winds, the four of us would get together every Tuesday and have a “Girls Night”. These nights rotated to a different house and a different household chore each week. Mine was usually some sort of landscaping, Ellen’s was traditionally scraping paint, so on and so forth. During these chores we’d talk about our lives – work, husbands, families, health, our bodies… and sex. We talked a LOT of sex. Knowing that you’re not the only one who has to pluck your upper lip daily is a glorious and very freeing thing.)

Either way, Ellen was known among our little group for having the most sex but the tamest sex life. Melanie and I were known for being the most “fetishy” but having the least sex. The other two fell in the middle with varying degrees of fetish-indulgence and instances. After a recent bout of just downright dirty in-depth discussion about the various turn-ons and fetishes within the group she wanted to step outside her box and experiment a little.

That’s right. She wanted her husband to wear eyeliner.

Note to young gentlemen who may be considering crossdressing but don’t know how to talk to their wives or girlfriends about your desires. Here’s a hint. Find out if your S.O. likes the Goth or Glam look. Even Emo is acceptable. Because eyeliner is a slippery slope my friend and if they enjoy the Goth look then you’re most likely going to be home free in the long run. Eyeliner on a guy is sexy. There’s something about it that I can’t describe. It just is. I’m not talking about going all out and wearing a dress or whatnot. Just eyeliner, possibly some black nail polish. It’s an easy way to ease your S.O. into the world of crossdressing without being “too girly” if you get my drift. Sure, you come off as Emo, but with only a hint of makeup you get to start your lady off with the best of both worlds!

Now, the thing to know about Keith is that he’s a really good guy. He’s quiet and respectful, funny and kind. He’s a good son and a good husband and he is one of the most supportive, understanding, and caring guy I know. But he didn’t want to wear eyeliner. It wasn’t that Keith was too cool or too macho to wear eyeliner – there were other reasons at work here, specific reasons from his past – but he found eyeliner to be a sticking point. He just didn’t want to do it. He was simply afraid that she would put it on him and then realize that she didn’t like it. He was scared to be ridiculed.

I think we all know that feeling, right? Who hasn’t bought a lovely new dress and put it on for a night out and had that moment of “are they going to like it?” in the back of their mind? It takes immense self-confidence to put yourself out there, even with someone that you LOGICALLY know wouldn’t make fun of you, you still have that trapped pimply teenager within screaming “I’m hideous!!! No one’s going to love me if I look like such a freak!!!”
Even with support and love, this feeling is hard to break. The less comfortable you were with yourself and your body growing up, the stronger that back-of-the-mind demon is.

Ellen eventually convinced her husband to put on the eyeliner. Then she promptly jumped him. I think he still felt a little silly and self-conscious afterward but since she traded the eyeliner for wearing an absolutely boobalicious corset, I think he thought he may have gotten the better end of that bargain.

So here are a few hints if you are trying to convince your man to step into the softer side of sex once in awhile.

1 – Find out how he feels about “experimenting” in the bedroom. It’s important to start off with this step as it will get all sorts of thoughts rolling in his head. Things he’s wanted to ask you to consider for YEARS but was always too scared to do so.
2 – Talk about a trade. If he’s always wanted to see you in a Snow White costume the chances are that you’ll have PLENTY of leverage for a little crossdressing fun. Dependent upon how dressed up you want him to be, you must be willing to go just as far with his fantasy too, even if the idea of it is a little weird to you.
3 – Don’t do anything dangerous. I’m not going to outline how many kinks out there are downright scary in their intensity and possibility of death if handled inappropriately. Do your research and don’t be afraid to say No to his kink if it wanders into the realm of “too scary” for you. Don’t feel guilty about it just offer to trade for a different kink or fantasy.
4 – DO NOT LAUGH AT HIM. It’s okay to laugh with him if he’s chuckling at himself but if he comes out of that bedroom in hooker heels and frilly panties and you start busting a gut you will not only put a big dent in his feelings you’ll also be harming your relationship. Men aren’t currently allowed the right to be feminine. He know, in the back of his mind, that he’s doing something traditionally considered “taboo” just to please you. Be aware of that fact.
5 – Have fun. This might be your only chance to see your guy with a skirt around his hips and smeared eyeliner. The shoe is on the other foot now. Call him a dirty little slut. Spank his butt a little. Think of a really bad porn cliche like the bow-chicka-wow-wow music and have it ready on the stereo to make you both laugh. See how he likes it. More importantly, see how YOU like it. It’s all about enjoying the moment.

Good luck!

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