We Have to Win!

"We have to WIN!" my wife slammed her fist in mock anger as we sat on our deck, drinks in hand.

"Okay, okay!" I laughed, holding my hands up in the universal signal for "I give up!"

Every year our friends hosted a costume party for Halloween and every year, in large part due to our crazy, hectic schedules, Donna and I ended up cobbling together last-minute costumes for the festivities. It was only when we showed up at the party, and saw some of the extravagant efforts by others, that Donna would bemoan our lost chance to be creative. For some reason, my wife's competitive streak was showing itself early this year.

"So what have you got!?" My wife challenged me. "We need a great idea..."

"I'm empty," I laughed, clinking the ice cubs in my glass together.

"Me too," Donna agreed, handing me her glass. "Freshen those up and meet me in the closet, we're figuring something out!"

I shook my head playfully as she pushed past me inside the house and up the stairs to our bedroom. I took my time pouring two more gin and tonics, hoping that a bolt of inspiration would hit her before I finished.

Unfortunately, that was not the case. As I joined her upstairs, she was pondering a pair of dresses, one in each hand. I wasn't sure what she was thinking but I did know I liked the idea of her sliding into one of the slinky numbers.

"I'm thinking famous couples..." she thought out loud. "But you know, with a twist. Something like Angelina Jolie and Brad Pitt as zombies. We need that extra something..."

"Well," I joined in half-heartedly, shoving through some of my older things towards the back of the closet. "I've got this old Yankees jersey... and you've got that low-cut white dress... we could do a Marilyn Monroe/Joe DiMaggio thing. Blonde wig for you... baseball for me... and... uh... some zombie make-up?"

"Ugh, with the zombies," Donna rolled her eyes.

Wait, wasn't that her fucking idea?

"But I like Monroe/DiMaggio, that's a good start... " she continued, pulling the white dress I was referring to from her side of the closet. "What's the twist... what's the twist..."

It was then that my own thought-thunderbolt struck me. It wasn't the most original idea in the world, but it would nevertheless be well-received among our friends... VERY well-received. But did I really want to go there?

"What?!" Donna stepped towards me, clearly catching the thoughtful look on my face. "What are you thinking?"

I stood there without answering for a second. The one thing I was certain of, even more than our friends loving the idea in my head, was my WIFE loving it. As soon as I uttered it, she would pounce, I just knew it. So in a split second I had to decide if I wanted to bring it up. I'm not sure how far the process got in my head. I just know that the idea flew out of my mouth.

"What if..." I paused, reaching out and taking the dress from Donna and pushing the throwback Yankees jersey towards her. "What if I was Marilyn and you were Joltin' Joe?"

Donna's eyes lit up as I knew they would. In voicing the idea I had doomed myself to being Marilyn Monroe for Halloween.

"Yes! Yes yes yes yes yes!" She actually jumped up and down, hugging the jersey to her chest. "Oh my God, you're going to be fantastic!"

"Yes, yes..." I said, looking at the dress in my hand and wondering what in the world I had gotten myself into. "I have a bad feeling that's exactly what the guys are going to say. That I look fantastic..."

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I really didn't think about it all that much over the next few weeks. But as Halloween approached, my own competitive nature started to take over. Sure, I was nervous, even at times mortified about the thought of dressing in drag. But I was even more nervous about not pulling it off. Should I shave my legs? What about make-up? How the hell was I going to pull this off???

It turns out I had nothing to worry about because Donna was on it. When I finally expressed my concerns the weekend before the party, she leapt into action.

"I've been thinking about that," she said. "What if I get you into my spa? We can get your legs shaved, your eyebrows plucked... and I can help you with the make-up obviously, we could even get some eye-lashes if you want..."

"Wait, wait... " I put up a hand to stop her roll. "Eyelashes if I want? Eyebrows plucked? I...make-up?"

"We have to WIN!" She said with a big smile, grabbing me by the shoulders.

"Oh God..."

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My wife has said before what a blessing it is to be friends with someone who works at a spa. She can get in after hours or sneak in when others wouldn't be able to. I never paid much attention. But clearly it was in my head somewhere because I insisted that if I was to go to a spa to get this, uh, work done, there was no way I was doing it in front of a room full of women.

So after a couple of phone calls, during which Donna giggled way too much for my liking, my wife announced I had a private appointment at her friend's spa after hours. So it was that I showed up at 9:00 p.m. on a Wednesday night (turning down an invite to watch the Lakers at a sports bar with buddies) to meet Melanie, Donna's energetic friend, who was tasked with turning Charlie into Marilyn.

"Oh my God this is going to be so fun!" She gushed, as she unlocked the door and physically pulled me into the lobby, locking the door behind me. "We've got work to do, let's go!"

We started at the top and I'm not going to lie, getting your eyebrows plucked? Not fun. I've always assumed that of course, but I earned new-found respect for what women go through on a semi-regular basis. That said, Melanie seemed to really know what she was doing. She put a hot towel on my face first (apparently to open the pores) and then, after the semi-tortuous process of pulling eyebrow hairs from my face one-by-one with a tweezer, put an equally cold towel on my face to help the skin recover.

She also gave me an old-fashioned razor's edge shave. Not my face, mind you (I'd have to shave Saturday before we left for the party for sure) but my chest. I hadn't even thought about that until she brought it up and was admittedly a little self-conscious lying in nothing but my shorts while she gelled and shaved my chest bare. I'm not an overly hair guy anyway, which helped. It didn't get any more comfortable for me when she asked me to raise my arms over my head... it took me half-a-beat to realize

"Shit, she's gotta shave my armpits!"

But the real adventure came after that. With my face and body from the waist up dealt with appropriately, Melanie took a deep breath and giggled.

"Okay, Charlie... shorts off!"

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Let me rewind a bit here. Before I left the house to see Melanie I had jumped in the shower. While thinking about what was to come, it occurred to me that in order to have my legs shaved, I was obviously going to have to sit there in nothing more than a pair of briefs (I should probably mention that as a boxer brief guy I actually had to go out and buy a pair of regular briefs for the occasion. I won't embarrass myself by admitting how long it took me to decide on which pair to buy for the occasion). And that realization led me to the following thought:

"Do I need to jack off right now?"

Because all I could think is how horrifying it was going to be when I was laying there in my briefs and Melanie, who doubled as a yoga instructor and was more than attractive enough to gain my attention, ran her hands down my legs. Ultimately I decided that the process itself would keep me, uh, down. After all, I've sat in a doctor's office in nothing more than a paper gown while an attractive nurse took my temperature and blood pressure. right?

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So now here we were. I slipped my shorts off, revealing the brand-spanking new blue briefs I was wearing and, what I hoped would remain, a calm package underneath.

"Okay, first things first," she smiled and pulled out a trimmer like you'd find when you went to get your haircut. "Let's shear you like a sheep!"

Melanie started down by my ankles and moved the trimmer up my left leg, trimming my leg hairs to short stubble. She went up to my knees on my left leg, shaving the shin and then gliding around to get my calf before repeating the process on my right leg. She then bounced back to my left side and began running it up my thigh. This is when the problems started.

Because, you see, those trimmers... well, they have these little razors that slide rapidly back and forth to trim the hair. And that rapid back and forth causes a bit of a vibration. And the vibration moving upward along my inner thigh, coupled with her hand on my leg as she used it... well, let's just say it started to get my attention.

"Oh no," I thought as I lay there feeling the vibration and the twitching beneath my briefs. "Shit shit shit..."

I lifted my head to look down where she was trimming and managed to look right down her tank top. Have I mentioned that Melanie was also a yoga instructor? She had a great tight body and perky tits and I was now looking right at them, with her left hand on my thigh and her right hand running a goddamn vibrating trimmer on the inside of my leg towards my crotch. Not good. I mean, GREAT. But not good.

By the time she finished my left leg, things were pronounced enough that there was no way she couldn't notice. As she moved to the right she glanced up at me with playful grin.

"I was wondering how this felt..." she teased. "I guess I have my answer!"

"I'm... I'm sorry..." I responded weakly, having no idea what else to say.

Melanie just responded with a giggle.

A few minutes later, she was done with my right leg, the trimmer once again sliding along my brief line as she finished my inner thigh. Somehow I managed to keep my mind focused enough on other things to not explode or pop out of the briefs.

"Let's go!" Melanie suddenly said, bouncing up and heading away from the chair.

"Uh, where are we going?"

"To the steam room," she said, matter-of-factly and then dropped her shoulders. "Silly guys, you have no idea. It's tough enough for me to shave your legs honey, you certainly don't want me trying it dry. I'm going to have you sit in the steam room for a bit and then we'll go to work!"

She walked me over to the steam room, opened the door and, as the steam rushed out to meet me, she told me to take a seat and she'd be in in a few minutes. I took a seat on the bench as the door closed and for the second time in a few hours contemplated if I should be rubbing one out quickly.

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"Okay," Melanie said, entering the steam room with a bucket full of suds. "Now to get a really close shave I would shave against the hair but... given that you're going to be wearing pantyhose, Donna didn't think you needed to be that perfect. So I'm going to shave down your leg... it'll be easier."

"I'm sorry, did you say pantyhose?"

"Charlie, hon, you have great legs, but they're unquestionably MAN legs. If you're going to pull this off, pantyhose will help... "

"Pull this off..." I muttered. "It's just a costume party for Godsake!"

Melanie laughed and took suds out of the bowl and ran them along my thighs. And then, with a straight edge, started shaving down my leg, starting on the outside of my thigh and then moving inwards. This time, I must admit, the act of a blade sliding downward along my leg helped counteract the view through the steam of Melanie's steam covered breasts under her tank-top. Eventually I leaned back and let her go to work, practically drifting off amidst the steam and heat. It felt like only seconds before Melanie asked me to flip over on the bench so she could do the back of my legs.

"And.... that's it!" Melanie announced several minutes later. "I won't say you're as smooth as a baby's bottom but you're close enough for Saturday night!"

It took everything I had to lift myself up. I ran a hand down one of my legs, the soft feel of hair replaced with a the smooth feel of wet skin.

"Now," Melanie said, looking up at me with sweat rolling down her face. "I'm going to grab you some aloe lotion. You can take a shower here or at home but either way, be sure to get this aloe on tonight to help skin abrasions. And Charlie, I'm not going to lie, it's going to itch a bit as it grows back in. The lotion will help with that too..."

I managed a weak smile.

"Thanks Melanie. I think I'll just get moving. It's late and I have to work tomorrow. I really appreciate you taking the time... I think..."

Melanie laughed again.

"Anytime Charlie! This is something I definitely don't get to do nearly as often as I'd like!"

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You know how long it takes for Thursday morning to turn into the weekend? How those last two days at work seem to take forever as you approach the fun of Saturday? Yeah, not the case here. I swear I put my head down on the pillow Wednesday night after my spa adventure and woke up Saturday morning to begin what could be... well, what was it going to be? The most humiliating night of my life? The most exciting night of my life? The only thing I knew for sure is it wasn't something I (or my friends) were going to forget anytime soon.

The party didn't start until 8:00 p.m. so we had time to get through our normal Saturday routine before heading to the hotel. The Johnson's Halloween party is held at a nearby hotel ballroom, think, wedding reception-type place. It's expensive but worth it, open bar, catered, etc... So we checked in at 3:00 p.m. and soon Donna was bouncing around downright giddy.

"Let's make you Marilyn!" she announced with an effusive flair.

"You are enjoying this way too much," I grumbled, putting down my iPad.

"Hey, this was YOUR idea!" she reminded me. "And, I should mention, you are sooooo going to get laid tonight for doing this!"

Well, okay then.

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First thing was to shave. I'm fortunately not one of those werewolf guys whose facial hair starts to come back in force hours later, but I still waited as long as I reasonably could. From there, Donna took over.

In the chair I went and out came the make-up. Guys, this is fucking torture. I cannot even begin to imagine how we, the gender who can't sit through a commercial or two without changing channels with the remote, could possibly be expected to do this every morning. Powder, blush, eyeliner, what the fuck is all this shit? Seriously, if I had to do any one of them on a daily basis I'd go nuts.

Donna, however, was loving it. I sat with my back to the mirror as she went to work, humming and giggling the whole time I might add, because she wanted me to see the "final product." It was like I was on that "Extreme Makeover" show, I felt like when it was all over I was going to have to walk through a curtain and have everyone cheer as my mother cried in delight and my father shook his head in shock.

So I sat there getting my face patted and brushed, my eyes lined and lashed. Then came the clip-on dangly (are they called dangly? Did I make that word up?) earrings Donna picked up at one of those mall jewelry stores and finally, of course, the blonde wig my dear wife scoured the area for. For a brief second I wondered if my wife had ever spent this much time getting ready for an event herself.

When she finally clapped twice and yelped with glee, I was... afraid? What did I want to see when I turned to the mirror? Because, let's be honest, there was part of me that didn't want to turn around and look good, ya know? What guy wants to look in the mirror and think "Hey, I'm a good lookin' woman!"

But of course, I didn't want to look awful either. If I was going to do this, if we were going to WIN, I had to at least be passable, right? Oh boy...

So with those conflicting thoughts doing battle in my brain, I turned and... wow. I looked GOOD. I mean, the closer you looked the more you could pick it all apart, but at a glance, I was downright cute! Oh Jesus what am I saying...

"No no, wait!" Donna said and practically bounced to the light switch. She turned off the light, then turned on the light in the adjoining bathroom, then played with the blinds. As she manipulated the lighting in the room the effect became more pronounced.

"It's going to be darker at the party," Donna explained, returning the spot behind me, looking at the mirror over my shoulder. "Honey, you look great!"

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From there it was a matter of finishing off the look. In I went to the oh-so-Marilyn white dress, complete with gel inserts to make me busty. The dress fell down just below my thigh (wait, wait, did I mention I had to pull it on like pants and pull the straps over my shoulders because, of course, I was already made up so I couldn't pull it on over my head for fear of ruining my make-up? Seriously, how the fuck do you women do this?) and the thigh-high nylons helped my legs look a little smoother than they were and cover up the start of my hair growing back. And yes, it itched like crazy. Oh and under the dress? Yep, peach, lacy panties. I had actually bought those myself. I thought it would make for a good laugh at the end of the night when I slid out of the dress in front of Donna.

While I was pulling on the dress, my wife was getting herself together. We decided she'd go with a "traveling" look for her Joltin' Joe costume, so she wore slacks and a button-down white shirt with a dark tie... and then over it, the old Yankee jersey.

"I've never been so turned on by a baseball player in my life, babe," I winked when she presented her final look to me.

"And I've never been more interested in being a lesbian!" she responded with an evil smile.

Okay. Let's party.

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I don't know that I've ever been more nervous than I was when the elevator doors opened onto the ballroom level around 8:00 p.m. The party invitation said the party began around 7:00 p.m. and the dedicated drunks usually got there shortly thereafter to get started on the open bar. I was hoping as many people as possible had blurry vision by now.

Donna and I had agreed very early on that we would tell NO ONE what our costume idea was, although I had through a couple of people that Donna had been intimating that she planned to take home the "Best Costume" prize this year. Then again, I think she always did that... we just didn't follow up her words with action.

When we arrived, there were a good 60 people or so already there and we instantly became the center of attention. Lots of smiles, some laughs, a bit of pointing. Our friends the Smiths (Johnsons, Smiths, can you tell I'm changing names to protect the innocent?) rolled up to us immediately and Roger went crazy.

"Ho-leeeeeeeee shit!" He half-yelled, breaking out in a huge smile. "Dude, I don't know if I can give you a hug I'm afraid I'll get turned on!"

"Awesome legs!" Gushed his wife Rachel, looking me up and down over the glasses that completed her "naughty librarian" look.

"Oh stop it," I cooed in a mangled attempt at Marilyn. "Now where's that bar?"

"This is going to take some getting used to!" Donna giggled as the four of us headed to grab some much-needed alcohol. "I'M used to being the one who's getting hit on!"

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And so it was for the next hour or so, taking shit from buddies, having their wives/girlfriends "ooh" and "ah" over my look (for which Donna joyfully took credit). Many of the couples we barely knew or didn't know at all took a minute to compliment me on my compelling looks. I took the compliments as best I could, although I'll admit some raging mental confusion. Was it crazy that "being a woman" getting that kind of attention was a total turn-on?

As the drinks went down, I dove into my character more and more. I started playfully flirting with guys, mostly getting roars of laughter, some high fives and, of course, a couple of uncomfortable "Uh, um, I...I gotta go find my wife..." responses.