Wednesday, February 16, 2011

Thing 296 Dress as a Woman

Yeah. That's me. Dan Mooney. I'm a twenty six year old MALE, who apparently can make a pretty passable woman. Pony Boy will never recover. I think he threw up in his mouth about fifteen times. The Frenchman looked ill, and while she helped, I think Little Flower was secretly disgusted with me too.

Initially I had help from Pony Boy and The Canuck, who helpfully looked up how to make male cleavage online, and then taped up my recently shaved chest to make it look like I'd boobs. It was upsetting on many levels. How many times in your life will you thank two of your best mates for duct taping fake boobs into your chest? Speaking of upsetting, here's a photo of me putting on a bra... I'm not what most people will call sexy...
After that, the cavalry arrived. There's no way a bunch of dudes are going to be able to womanify me to the standard required. I'm not talking about looking like a Drag Queen, mostly because I look like that when I put on a wig and have a few drinks, so there's nothing new about that. I was going for proper woman, or at least to see if I could convince friends and family that I'd pass as a woman. I like to think that based on that photo up there it's a case of mission accomplished. But for that kind of look, the cavalry really was required...
Enter Little Flower, Clo Bear, Talker, Tiny Fairy and Blond Boss. A note on Blond Boss - the woman can get so excited that she's like a six year old child, stuffed with skittles, coke and crack. She's an absolute legend though. And she painted my face goodo. I think it was needed. The more makeup the better, I'm hardly an oil painting as a man, trying to look convincing as a woman is going to require about two and a half inches of makeup.... at least.

Just look at that photo. Is it weird that I'm trying to look down my own top every time I see it?
When we were all done applying two and a half hours worth of makeup to my face, and stuffing me into a pair of shoes, it's time to hit the town. It was CiCi Doo's birthday, she's been my older sister since I was born. So the four siblings decided to go for a few bevvies. That's drinks for those who didn't get that. Poor Thorny Wire didn't know where to look, the man was never so uncomfortable in all his life. "I've feckin' three sisters all of a sudden", he said, with a scowl...

So there's his three sisters: Me, Bean Bag and CiCi Doo.
Yep. This is the weirdest, strangest, most unsettling night out ever. We hit five pubs, Blond Boss joined in, and I spent the night looking for friends and people I knew, popping over to them in the pubs, tapping them on the shoulder and seeing if they'd recognise me. Not a lot of them did. In retrospect, when you're a man, dressed as a convincing woman, the last thing you should be doing is drawing attention to yourself.

Mind you, the reactions were funny. The lesson learned: High heels are dreadfully uncomfortable. Sympathy for all women who wear them. I feel your pain sisters.


  1. Dan, You have a fine set on pins on ye there.

  2. dan you are soooo pretty......

  3. You could of combined a number of your challenges into one here. Dress as a woman, wear women's undersware, buy a vibrator, wear false nails, bikini waxing, wax your eyebrows, shave your chest, go on a double date (with a guy), so thats 9 in one night. Then add a few more like spend 24 hours as a woman, use a vibrator, french kiss a man, sex with a man, then take a pregnancy test, enter the alternative Miss Ireland. Maybe for your 30th you should do these?

  4. Unsettling because it wasnt that unpleasant after 5 minutes...?

  5. Come on Dan tell us the looked a little too good.
    Not the first time you've done this right?
    Or you can't wait to do it again?

  6. Welcome aboard girl friend!!!

    It would be ashamed to do it just once!

  7. Putting on a dress for the first time has to be something similar to eating just one Lays Potato chip. You just can't stop at once! You look awesome! and welcome to the wild side!

  8. You failed, Dan. You didn't dress like a woman at all. To do that you should have skipped the make-up and just thrown on some sweat pants and flip-flops, because that's what all the women I see these days look like.

  9. Dan, you looked great. Sounds like you had a fun time (except for the heels :) Is your cavalry available to help other girls look as good as you did?

  10. Ah, Dan ... the real question is with whom did you go home at the end of the evening? And, when you did, how did she react? Wasn't it a wee bit fun to let the (other) girl take charge?

  11. You are very pretty as a girl, dressed again next year.