The Task Pt. 02

Hi! Part Two of 'The Task' follows as Cassie and Luke continue their preparations for Luke's new look. Welcome back to those who read Part One and thank you for returning. Your patience is appreciated - none of this was written in advance so there will be a bit of lag between chapters - sorry!

If you're new to this story you might want to read Part One first but it's not absolutely necessary in order to follow along. There's a bunch of different things going on but in the end it's a story about cross-dressing and that's why it's in this category.

As always, comments both good and bad are welcomed and if you enjoyed this please take a moment and leave a good rating. Part Three, which should be the final chapter of this tale, will be along as quickly as I can write and edit it.

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"There you are!" Cassie gave a tiny jerk of her head before patting the cushion next to her. "Come over here, please. I need to ask you some questions." Her fingers returned to dancing along the keyboard of the laptop that was appropriately perched on the top of her lap.

I didn't need to be asked twice when it came to sitting next to my wife, especially when she was wearing leggings that showed off her thickly muscled legs and a tank top that was struggling to keep her contained. Plopping down on the couch, I cracked open the beer I'd been carrying. "Sorry it took me so long. I do love me a long, hot shower, especially after class."

She didn't look away from the screen but still managed to snag the bottle as I raised it, firing down a swig. "I hope you were smart enough to bring two," she said, smiling as I raised the one in my other hand. "Look at me, marrying a clever one. So glad you've been able to learn from your previous follies."

I let my gaze linger on her dark eyes, her high cheekbones, her nose (in her opinion 'way too fucking big' and 'potato-shaped' but I loved the way it fit her), the lock of curly black hair that had escaped the bun on top of her head to hang next to her ear. "Has anyone ever told you how gorgeous you are?"

"Sure, but they were usually just trying to get into my pants." She took another long pull from her bottle before setting it down on the table at the end of the couch. She started typing again before pausing and raising an eyebrow. "You are trying to get into my pants, right?"

"I mean, I can wait until we go to bed and you take them off if you don't want me to be like all the other guys. No pants to be gotten into then."

"Look at you, assuming only dudes tried to get me into the sack. Tsk tsk tsk." She wiggled the mouse that sat on a little extended panel, squinted at the screen. "I'm going to cut you some slack because you were raised by troglodytes and should be wayyyy more messed up than you actually are. Then again, I'm the one doing my best to turn you into a filthy whore so I suppose I deserve some credit there." She cracked a huge smile and gave me an exaggerated wink. "BUT - to put your mind at ease after your weak and obvious attempt to see if you're going to get laid tonight, well, you're going to get laid tonight."

"By you?"

That earned me a poke in the ribs. "It better be by me. You think I've been a big supporter of your martial arts training because I want to see you master the two-inch punch?"

"It's 'one inch,' and -"

"Don't care. I'm just here for the washboard abs and ropy arm muscles, kid. Only thing I plan to use your eventual black belt for is to tie you to the bedposts."

I shook my head, grinning like a fool. "I don't think you'll be able to accomplish that with one belt, Cass."

She made a dismissive noise.. "How dare you besmirch the life skills I learned in Girl Scouts?" The mouse clicked a few times. "If you're that concerned then earn more than one black belt, you lazy slob. How difficult can that be?"

"Considering what I'm going through to get just this one, I'm going to say it's pretty difficult. Can't you use some of the lower belts instead?"

"Unnggghhh." She shook her head. "Such a plebian. No appreciation for the aesthetic tableau I'm trying to create. ANYWAY." Cassie turned her computer so I had a better view. "Not that you asked, but I've been working on prepping for THE TASK." She said the final words with exaggerated enthusiasm.

Ah, yes. My punishment for finishing last in my fantasy football league meant that I was required to imbibe one full drink in a bar of my choice while dressed as a woman. When I first found this out, given my religious and conservative upbringing, it sounded like the end of the world to me. However, I have been blessed with a wife who is wonderful in any number of ways, one of which was convincing me that this could be treated as a feature rather than a bug. Inwardly I was still nervous and dubious, but I'd put the whole shebang into her loving hands and it was difficult not to get caught up in her whirlwind of enthusiasm.

"So. One thing we don't have to worry about is shoes - you're going to have to wear flats."

"Oh." I felt disappointed although I had no idea why.

"Listen to you, all bummed because you can't wear fuck-me pumps. I don't need you spraining an ankle AND, in case you haven't noticed, you're already like eleventy-bajllion feet tall. Besides," she said with a wink, "all shoes are fuck-me shoes if wear 'em right."

I had no smart-ass comment for that and suffered her smirk with dignity.

"First things first. You need to pick out a wig." She gestured toward the screen. "This site has a pretty good selection."

"A wig?"

"Yes, a wig, you big doof. Your high and tight may look good on you but it's not the softest of hairstyles, know what I mean?"

I sighed. "No, not really. But you're in charge, so I reckon I need to pick out a wig."

"'Reckon?' You slip off to the Deep South when I wasn't looking? If you did and came back without biscuits we are Going. To. Have. Words." She held a glare for a few seconds before melting back into a smile. "Anyway, a wig is a good starting point. Helps set the theme."

"Isn't the theme 'Doofy Dude Tries to Pass Himself Off as Hot Woman, Fails Miserably'?"

That earned me a genuine scowl. "Oh ye of little faith, Nancy Negativity. If you decide to go with, say, something orange-y then I know not to buy a red sweater because it would clash." At my blank expression - fashion is not my forte - she rolled her eyes and said, "Just look at some wigs."

Turning my attention to the site allowed me to quickly understand that there were A LOT of wigs to choose from. I'd expected there to be different lengths and colors but was stunned by the hundreds of different styles. Part of me was like 'oh just pick one already, who cares,' but that previously silent part of me that was more excited about all this than I was willing to admit to myself was not interested in glossing this choice over. That being said, ye gods there were a lot of wigs to go through.

Cassie was more patient than I would have been in her position but after a solid fifteen minutes of watching me bouncing around the site with no real rhyme or reason she cleared her throat. "I'm starting to see that this might be a bit overwhelming. Would you, maybe, like some help?"

I rocked my head side to side. "I feel like if I can get one aspect down it'll get easier after that."

"Okay." She peered at the screen, one of her hands dropping to the inside of my thigh. "Let's go with length. Extra-short, short, medium, long, or extra-long?" She sighed at the confused noise I emitted. "Let's narrow it down. We can get rid of the extras, I think."

"Why?" I was genuinely curious.

"Well, your hair right now is extra-short, so that's just boring. Extra-long might look good but - and I can speak from experience - it tends to get in the way while you're sucking cock." She gave me a knowing look.

"Oh, I understand what you're - wait, what?"

Cass gave my leg a squeeze, her dark eyes dancing with mischief. "You could pull off a short style if it's a busy one, but between your height and your long neck I think something that hangs below your shoulders will be the most flattering." She paused. "And hide things better off hidden."

My brow furrowed. "I have a long neck?"

"Like a goose, babe, like a goose." With the swiftness of a striking cobra she twisted and planted her lips against the side of my neck, right on that spot she knew reduced me to jelly. Well, not all of me. A groan escaped my lips as I first felt her teeth worrying the skin before her tongue traced a path to the junction with my shoulder. The pajama pants I was wearing became noticeably tighter as her mouth worked its magic and I had collected my wits enough to grab at her when she pulled away.

"Nuh-uh," she said, color evident in her cheeks. "Playtime later. Work now."

I scowled. "But you started it!"

"I know! I'm an awful, awful tease. Kinda feel like you should have figured this out over the past decade or so." She glanced down at the obvious bulge in my pants and smiled. "You sure do know how to make a girl feel wanted, but let's get back to trying to make you a wanted girl."

"You've been saving that one, haven't you?"

"I admit to nothing." She jabbed a finger at the screen. "So, long then? Seems appropriate," she said with a smirk.

I gave her the fish-eye before returning to our quest. As I'd hoped being pointed in a direction made the ensuing choices easier, and before long I felt I'd found one that might work. Cassie rubbed her chin as she considered my potential selection.

"Hmm. Shoulder-length, face-framing bangs, layers of loose curls that are a little bit messy... interesting." She nodded. "You wear that and it'll look like you got railed good and hard and did some minimal primping before heading out. You good with the color?"

"Yeah, I think so." After checking out the available palette I'd settled on a dark brown with auburn and blond highlights. Cass was dead on with her description - it did look like the hair of someone who'd just been well-fucked. I tried to imagine my face there instead of the model's, looking all tousled and satisfied, and my still semi-hard cock immediately became a shaft of stone again. I kept waiting for the shame to kick in but instead I realized I was running my tongue along my upper lip.

"Oh, my." Cassie was looking at me with the same expression our cat got when we started opening up a can of tuna. "This is going to be fucking amazing. Damn, I wish you'd sucked at fantasy football years ago."

I should have given her a sneer but was still too transfixed by the image of me wearing that wig that was running amok in my head. "So, this one? Will that fit with your clothing plans?"

She laughed. "Oh sugar, even if it didn't there's no way I'd do anything to keep you away from something that's ringing your chimes like that wig is. Don't you worry, I'll make it work." Cass turned the computer back to facing her, bonking my straining shaft on the way. "Oops. Let me tell you, that thing is always in the way."

No objection if you want to make it go away, I thought. "Is that real hair? I mean, to make the wig?"

"Not for this price, no. If it was something you were going to wear every day we'd go for that extra expense, but even so we're not ordering a wig from Spirit Halloween here." She tapped at keys for a bit. "Okay, ordered. A good beginning. Now, let's talk tits."

I blinked several times, which made her giggle. "Uhm."

"Gotta figure out cup size first. An A is going to be way too small for your build, and a D or above might be overkill, although they would distract. Hmmm." Cass gnawed at her lower lip. "I'm going to suggest a nice, full C cup. Big enough to catch the eye but not make it seem like you're smuggling cantaloupes."

"They have different sizes in padded bras?" My eyes widened as a thought occurred to me."You aren't planning on getting me implants, are you?"

My wife is a person who COMMITS to a belly laugh. She doesn't try to fight it at all but rather embraces it fully and lets herself be swept away. I felt obliged to grab the laptop as she folded up, helpless in her laughter. I wanted to be grumpy but it was damn near impossible when in the presence of so much radiating joy, so I spent the time trying to keep from smiling as she wound down. After a few deep breaths, Cass wiped at her eyes before kissing me on the cheek.

"Why... ah, I'm going to start laughing again... why would I go to the hassle of implants when I've been putting estrogen in your food since we started on this thing?" My terrified gaze nearly set her off again. "No, love, no implants. And I'm not serious about drugging you." She dabbed away a lingering tear. "We are not going with a padded bra because when you wear a padded bra, guess what it looks like?" She didn't wait for me to answer. "Right, it looks like you're wearing a padded bra and I, sir, will not allow us to present a slipshod end product." Reclaiming her laptop, she clicked on one of the several million tabs she appeared to have open. "So, there's this."

I leaned over to see what looked like a high-throated tank top that sported an impressive set of breasts. "That's... interesting."

"Yeah, and again, if you were going to be doing this every day instead of for your Task I'd be recommending this route but it might be more than we'll need." She tapped a finger against her cheek. "See, I like that it's designed to cover up the Adam's apple." She paused to squint at me critically. "You don't really need that, though. Yours isn't very pronounced. Plus, I've heard that these can get hot and uncomfortable to wear for a long time."

"Makes sense." I peered in. "Also, I'm not sure I'm the exact match for any of the colors they have there."

"Another issue we'd rather not have to deal with, along with make-up to conceal the edge... we're much better off with another option." She clicked on a different tab. "Like these."

"Hmm." I cleared my throat. "I mean, they look like boobs. I guess you just shove 'em into a bra?"

Cass put a protective arm over her bosom. "You don't just 'shove' things into a bra, real or otherwise. And no, they'd look terrible if that's what you did. These stick to your chest via adhesive."

"Adhesive?" I pulled my shirt collar out and gave a dubious look at my somewhat hairy chest. "That sounds like it's going to hurt like hell when they come off."

"Mmm, no." Shifting her position, Cass stuck out her right leg and pointed her toes until she was able to hook the backpack on the floor that she usually took with her to work. With a grunt she pulled it over to the couch and, after unzipping a pocket, started rooting around inside. After about thirty seconds she rolled her eyes and started digging around with both hands, grumbling under her breath. The laptop started to list in that direction and I was just about to grab it when she let out a triumphant HA! and brandished something over her head.

"Try to hide from me in the exact place that I put you, eh? Now who looks foolish?" She gave me a smug look while nodding her head. "You know you married a crazy person, right?"

I shrugged. "Yeah, but a SEXY crazy person."

"Good choice, since we're the best in bed. AS YOU KNOW." She waggled her eyebrows before tossing me something that was about the size and shape of a tube of toothpaste. "You're going to thank me for the countless tiny cuts this is going to help you avoid."

"Depilatory cream," I read aloud. It took me a moment to remember what that meant. "I... you want me to get rid of my hair?"

"Not the stuff on your head, no." She gave me an appraising look. "Your arm hair is pretty light-colored so that's your call, but I'd recommend at least doing the back of your hands and your knuckles. That's in addition to your chest and your legs, of course. Those forests have *got* to go."

It felt a little more difficult to breathe. "Is... is this necessary? Seems like a lot."

Cass softened the rolling of her eyes with a warm smile. "You shave your face every other day, right? Think of it as expanding that area somewhat." She sighed. "It might seem like a lot and indeed it might be a lot, but everything we do should help make you feel more confident on the day of The Task." Raising a palm skyward, she added, "Don't forget - you were the one concerned whether or not you'd end up being attractive."

Difficult to ignore your own words. "You have a point." I turned the tube over in my hands. "Do you use this?"

She laughed. "Given how many times you've complained about knocking my razor out of the shower caddy you should know that answer. I'm lucky enough that my own body hair is fine and slow-growing enough that infrequent shaving is good enough for me." She blinked a few times. "My grandmother had a mustache to rival Einstein's, though. Not sure how I dodged that genetic bullet but yay me." Reaching over, Cass tapped the instructions printed on the cream. "Make sure you follow those instructions, right down to doing a small test area first. Don't screw around with this stuff - it'll burn the hell out of your skin if you leave it on too long."

I made an involuntary glance downward. "It's safe to use around my, uhm, junk?"

"I love it when you talk all sexy, babe. It would be okay there but since you keep that area well-groomed you're probably okay not worrying about that so much."

Big relief there, but... "The chest and the legs are a must, though?"

"Oh, yeah. You're probably not going to be showing deep cleavage but the last thing you'd want is chest hair poking out." She grabbed my thigh and gave it a squeeze. "As for the legs, well, there's a good chance you're going to be in a skirt or a dress and hairy sasquatch isn't going to fly."

A dress. Or a skirt. That hadn't occurred to me. "Good chance?"

"Better than good chance. Great chance. Bet the over on 'skirt and/or pants.'" She gave me a positively lascivious look. "You have legs I wish I had."

I flexed under her hand. "Really?"

"Look, I love my body but between years of gymnastics and hockey my legs are definitely considered 'bulky' by today's standards." She rubbed her thigh, tilted her head. "I mean, they're sexy as fuck but I'm not going to be kicking with the Rockettes anytime soon."

"I love your legs," I said. "And I think they look great in stockings. Out of them, too. Speaking of..."

"Easy, big fella. We still have work to do here. Since you were kind enough to bring up stockings let me use this moment to alert you to the fact that whether you're in a dress or a skirt you will, without a doubt, be wearing a pair." She made a hungry noise. "You've got legs like a pin-up model yet somehow masculine at the same time. Thinking about them sheathed in black nylon, well, whew." Cass fanned at her face while making playful panting noises. "Hubba hubba, although in this case 'hubba hubba' means 'my panties are soaked through.'"

I was starting to believe I had another fun evening ahead of me. "Hubba hubba indeed. No pantsuit for me, I guess."

She raised an eyebrow. "I mean, you can crush my dreams by going all Hillary but that does mean we'd have to employ some sort of containment system." Turning her attention back to her laptop, Cass popped open a new tab and typed away. "So, let's learn some new words, like 'gaff,' and 'tucking.'"

Learn I did, my mind being somewhat blown in the process. Ye gods, I've led a sheltered life. "Uhm. As you've no doubt noticed I'm surprisingly optimistic, even a bit enthused, about this whole endeavor."

"Indeed. I am both shocked and deeply, deeply excited by those unexpected turns."

I glanced at the screen again and coughed. "That being said, I'm not sure this is a bridge I'm quite ready to cross yet." I paused. "That's not to say I think there's anything wrong with them or that I'd never consider using one of them but, you know?"