The Task Pt. 04

"Whatever you say, Mr. DeMille." In the background I heard a couple of people taking a crack at 'Fat Bottomed Girls.' I drew in a deep breath, holding it for a bit before letting it escape. "Okay. I'm ready for my close-up."

Cass blew me a kiss before centering her phone and pressing the screen, nodding to let me know we were on. For a few seconds I just smiled at the camera, imagining the reactions from my league and the need to let them settle back down again. When I figured it was long enough I gave a little wave and said, "Hey. Not sure if we've met before. I'm Leia."

I paused again. I had used exactly the kind of voice Cass had suggested without being consciously aware I was doing so but the world didn't immediately end so I figured I might as well stick with it.

"As per the rules of our league I hereby submit this video as proof that I am completing the required Task. I would also like to add that I'm doing so looking better than any woman unfortunate enough to have dated Jed."

Cass snorted with laughter. Picking up my drink - ye gods, it was heavy - I nodded at the camera before taking a pretty long pull from the straw. "As you can see I have my mandatory drink, which is absolutely ludicrous in size. Drinking the whole thing rapidly is not an option so we'll probably have a few breaks in the filming - say hi, Cass."

"Hi." She then turned the camera around to show her grinning face for a moment before spinning it back to me.

"To prove I'm not just a pretty face, allow me to show that I have complied with the rules from head to toe." After setting down my drink and standing up, I raised my palms skyward while I did a slow spin in place. Those around me broke into applause again as I made my circuit, tossing in a few catcalls as well. A myriad of sensations washed over me: the bite of the straps on my shoulders as they supported the weight of my breasts; the grip of the welt as the muscles in my thighs rippled beneath them; the smooth kiss from the stockings as my knees brushed against one another; the deliciously rough touch of the skirt rubbing against my bare ass; the mild ache in my flexing calves; and, of course, the twitching of my cock as it rose in response. I almost couldn't believe how sexy and naughty I felt, wearing this second skin of sorts. My nervousness had been reduced to an occasional flutter, my confidence bolstered by my wife and the cast of friends she'd enlisted.

As I faced the camera again I reveled in the look of naked lust on Cassie's face. Our car ride home later was going to be VERY interesting if I had my way. Would be a terrible shame if my skirt just happened to flip up while we were stopped at a traffic light...

That thought put my skirt to the test and I sat back down, making a show out of crossing my long and if I may say so myself quite shapely legs. After taking another pull from my drink, I turned my attention back to the camera. "I would be remiss if I didn't thank the person responsible for helping me do it. I truly hope all of you have or find someone as wonderful as Cassie to spend your life with. You can't have her, though. She's mine." I blew her a kiss before flourishing my hands toward my body. "My wardrobe, my wigs, the expert she brought in for my makeup, even my lovely rack, all of it was her. Couldn't have done it without her."

Cass flashed a knowing smile before laughing. "That is so, so very true."

I took another drink and was gratified to see that the contents of the glass had gone down noticeably. "So enjoy the rest of the video, and hey - it's okay if you think I look hot like this." I made a big, exaggerated wink. "You're not wrong. Anyway, I'm looking forward to finishing not-last next season."

My wife passed the phone over to Emma before coming over and plopping herself on my lap. She gave me a smile before looking back at the camera. "Allow me to offer proof that this is indeed my husband and not some random woman we hired as a stand-in." With that she gave me a kiss that elicited a few howls and made sure I advanced from semi-erect to achingly hard in the few seconds our lips were pressed together.

With the newness of my appearance having worn off a bit some of the coworkers began making trips up to sing as I chatted with others and worked on my drink. I might not have been super boozy but volume is volume and by the time I'd polished off three-quarters of it there was a bit of a buzz present. Perhaps more than a bit, which might explain why when Cass asked if I wanted to sing with her and a few others I didn't even hesitate before agreeing to join in.

My thought-to-be-vanquished nerves re-established their presence with authority during our walk to the stage. It's doubtful that every pair of eyes in the place were judging me but my imagination sure wanted me to believe that was the case. The urge to bolt came out of nowhere and I was scoping out an exit when Cass, who somehow knew, grabbed my left hand. That would have been enough to break the spell even without the additional boost of Tamra grabbing my right a few seconds later. Instead of faltering, my stride grew stronger and soon the five of us - the others were an older woman named Misha and a guy in scrubs I'd never met before - were on stage. Given that under normal conditions my singing voice sounds like someone doing unspeakable things to a cat with a fork I had no intention of taking a chance with Leia's, uhm, smokey pipes and so was happy to mouth the words to their selection of '7' by Prince. They absolutely KILLED it, but to be fair I was both biased and a wee bit drunk. In any case, I had a blast dancing along to my fake singing. It was pretty hot up there, though, and as I felt myself start to perspire I toned my gyrations a little so I wouldn't be in danger of launching one of my boobs into the audience.

Yes, I know that's a ridiculous thing to worry about but one should keep in mind the gigantic bucket of Nuclear Meltdown I'd been swilling from. In any case there were no flying prosthetics to speak of and we shared a group hug before heading off stage, during which Cass grabbed my ass.

I sure *hoped* it had been Cass.

Back at the table we discovered that our party was now intermingled with other folks, most of them dudes chatting up the nurses. Cass headed off to the bathroom while I flopped back into my seat, draining half of what had been left of my drink without coming up for air. Grabbing a nearby napkin I dabbed at the sweat beaded up on my forehead, hoping it didn't take too much of the foundation away.

"Is it okay if I sit here?"

I started, surprised, before looking over. A guy with long blond hair pulled back in a ponytail was pointing at the seat next to me. I assumed he wanted to take the chair itself to another table but at my nod he popped open the button on his suit jacket and sat down. On the short side and slender, he took a swig from his bottle of beer before setting it on the table.

"Thanks. I'm Ken."

Ah. Another thing we hadn't foreseen as a possibility. "Uhm, hi," I said, shaking his proffered hand. For a moment I dithered - who was I right now? - before figuring 'fuck it.' "I'm Leia. Nice to meet you."

"Likewise." He gave me a frank and appraising look. "Do you mind if I ask you something?"

Oh, brother. Here we go. If he asks me why we didn't sing 'Dude Looks Like A Lady' instead I might just pop him one. "Sure."

"Excuse my forwardness but did you do your own makeup? Because it's fantastic."

Okay, that's not what I was expecting. "Ah, no. My wife's coworker is a cosmetologist. And a nurse. She's, uhm, both." I wished I had a mirror on me to check the current condition. "I thought it looked okay but I don't have a lot of experience with this sort of thing."

"First time? I wish I'd had a friend like that for mine," he said with a laugh. "Went way too heavy with the eyeshadow. Learned a valuable lesson from that one."

I furrowed my brow, waved a finger at his clothes. "But you're not..." I trailed off.

Ken sighed. "Yeah, but I wish I was." He gestured at the far side of the room. "Here with a bunch of dude bro coworkers for a 'morale building' outing. Don't think they'd be okay with me showing up to this exercise as Kendra." The corner of his mouth curled. "Of course, if they met me as Kendra elsewhere they'd probably fight each other to be the one who gets to try to impress me with tales of financial derring-do."

"Oh. You, uhm, look good?"

He nodded. "Allow me to toss aside false modesty - I'm a fucking smoke show. I'm comfortable and confident and it radiates off me like heat from the Sun." He took another drink. "Looking forward to when I can be who I want to be - who I'm supposed to be - full time."

"Ah." I wasn't quite sure what I had walked into here. "I hope you get to be yourself sooner rather than later."

He held up a hand and waved long, graceful fingers. No nail polish, though. "Sorry. Sometimes it gets frustrating but that doesn't mean I should unload on someone I just met who is enjoying their first time out. I'm right, no? First time out?"

"Is it that obvious?" I wondered what I'd done wrong.

"Oh, not in the 'everyone is staring at me because I look ridiculous' sense. I can spot it because, well, been there done that, you know?" Ken reached out and gave my hand a quick squeeze. "You look terrific. Really. In fact, you and her -' he pointed at Tamra - 'have my coworkers fantasizing about being in the middle of, as they put it, 'an Amazon sandwich.'" He rolled his eyes. "Eternal frat boys, I swear."

I had no idea how to process the knowledge that a group of guys wanted to fuck me. Well, as part of what they thought would be a MFF threesome, but still. It wasn't something I wanted to have happen but at the same time I felt a little thrill at being desired by people who thought I was a woman.

Ken must have read it in my face. "I get it." He reached into his inside jacket pocket and produced a business card. "The front of this is my business info, which you're probably not going to care about unless you need lending for your corporation. On the back, though, I've written down a website and a password that allows access. It's sort of a support group but it's also pretty social, and it doesn't matter if it's something you only do occasionally or if you're transitioning or fully transitioned - everyone is welcome." He made a face. "I'm not going to say there aren't a few cliques because some people refuse to let high school go but I know I find it warm, supportive, and a goddamn blessing. Some nights a bunch of us go over to someone's house and just enjoy being ourselves in a safe and accepting environment. Gotta tell you, it doesn't suck."

"Thanks." I took the card from him with no idea if I'd use it, but I was touched by the gesture. "And also thanks for your kind words. This is both nerve wracking and enjoyable but having someone who doesn't already know me say I'm doing okay is wonderful."

Ken's smile lit up his face and made it easy to see how he'd make an extremely attractive woman. "You are welcome. I would ask that you be careful with what I've given you - if you're not interested that's fine but please don't let anything happen that would jeopardize the site and those on it." Standing up, he held out his hand again. "Very nice to meet you, Leia. I'm going to go back and tell the dolts I work with that you shot me down. Hope to see you again." He walked away after we shook, leaving me to mull over the strange and interesting new developments in my life.

Cassie sat down in the chair next to me and shook her head. "I go to the bathroom for a couple of minutes and you're already taking cards from guys. What sort of wanton, libidinous trollop am I married to?"

Even though I knew she was teasing me I could feel my cheeks burning. "He was... he does..." I blew out an exasperated sigh, took a deep breath, and managed to explain what had happened without stammering again.

"That's really cool - both him coming over and the support thing." She arched an eyebrow. "Not to mention that you look good enough to fuck."

I picked up my drink, which was pretty much down to the dregs. "Well, as part of a package."

"Wait!" She pulled out her phone. "We have to film you polishing off your drink. Otherwise we'd have to do this again and I know what torture that would be for you." It was impossible to miss the smirk on her face. "Okay, suck that thing dry."

I almost choked at her words but with a wave at the camera I emptied the glass and, when finished, smacked my lips. "All done! Task accomplished!"

Those close enough to hear cheered. Cass stopped filming and leaned in to give me a hug. "So proud of you for doing this. You were amazing. Not to mention that you look good enough to fuck."

"That's me, the desire of financial bro dudes everywhere."

My wife leaned back, closed her eyes, and shook her head. "Not. To. Mention. That. You. Look. Good. Enough. To. Fuck."

"Yeah, you said that and I... oh."

Her lips, shining with freshly deployed bronze lipstick, curled into a smile. "Do you want to stay longer, or shall we go? I'd strongly suggest the latter because I have access to confidential information that indicates you're going to like what happens after that."

Judging by the way it hardened and pushed up against the front of my skirt my cock was a big fan of that idea. "Do you think we've been here long enough? I mean, for the video?"

Cass showed teeth. "We've been here for over two hours, Leia. If I didn't know any better I'd say you've enjoyed yourself."

I never wear a watch and she had my phone in her purse, so I had no idea it had been that long. "Wow. Time flies when you're cross-dressing."

She leaned in close to me. I thought she was doing so to whisper something but instead her teeth tugged at my earlobe while one of her hands found my knee and began sliding up my leg, disappearing under my skirt. I gave a sharp intake as she roamed past the edge of the welt and onto my bare thigh, her knuckles bumping against the underside of my cock. "I'm not saying we *have* to go, but... I'm thinkin' you might *want* to go. This night isn't over yet."

"Check, please," I said in a whisper. "Although now I have to try to get up to say goodbye before anyone sees how my skirt is tented."

She elicited a groan from me by flipping her hand over and giving my shaft a firm squeeze before vacating the premises, so to speak. Standing up, Cass tilted her head and tapped her lips. "So, stay or go?"

For the first time tonight I was happy about the ridiculous size of my drink glass as I was able to use it for concealment as I did a quick adjustment. My getting things under control coincided with the end of someone singing 'I Will Survive' and allowed me to be heard by most of our crew. "Everyone - we're going. Thank you all so much for being here and being supportive. I mean."

The next few minutes were spent getting hugs, congratulations, and a giggly, whispered request for a private showing 'if Cassie was okay with it.' Once we'd finished the goodbye queue I mentioned it to Cass, who made a disgusted noise and glared back over her shoulder.

"Let me guess - short, pale, freckles, braids?"

I searched my memory. "Uhm... sounds right. I don't think I've met her before."

"Yeah, that's Fiona. She's relatively new. Nice enough, but when she gets a few drinks in her she wants to get something else in her." She tapped my leg. "It's a few inches to the left, in case I was being too vague."

"I got it, I got it." Glancing around as we got close to the exit, I made eye contact with Ken. He gave me a slight nod, which I returned. Cass clucked her tongue as she pushed the door open.

"Wow, slap a pair of tits on you and what a shameless flirt you become." She laughed and took my arm. "I hope you remain shameless forever. Well, except about things that deserve shame. Nothing you've done tonight qualifies."

I hadn't realized how warm it had been inside until the cool night air wrapped itself around us. Heels clicking in unison as we walked across the parking lot, my cock twitched at my plan to tease her on the drive home."Night's not over yet."

She gave me a sideways glance as a big, slow grin crept into place. "Indeed. I bought the deluxe 'Husband as a Hot, Sexy Woman' package and you're still under contract."

I started to slow as we neared her car but she kept her pace, pulling me along by our linked arms. Our destination appeared to be the entrance of the Hyatt Suites, and for a moment I grinned at her planning. Then I felt a flutter of fear in my stomach at the thought of us checking in. Being surrounded by compatriots in a dimly-lit bar was a lot different than standing under harsh lights in front of a welcome desk. The night air suddenly didn't feel quite as chilly.

Cassie's arm tightened around mine, possibly due to her feeling me tensing up. "Do I need to remind you how fucking glorious you are right now?"

I released a breath I hadn't realized I'd been holding. "No, but..." As the automatic doors whizzed open at our approach I toyed with the idea of claiming to need the bathroom while she got the key but dammit, I didn't want to be a coward, did I? For fuck's sake, I got up on a stage in a bar while dressed as a woman and sang karaoke - well, I pretended to sing. Despite knowing this was something I could easily navigate, the dread in my gut remained, with the restroom plan sounding more and more plausible. But no! Cassie was right, wasn't she? I was killing this. And JFC, look at my legs! I was -

Cass didn't so much as pause as we passed the front desk, murmuring a 'good evening' to the receptionist as we swept by. Moments later we walked into a waiting elevator as a guy already in there held the door for us. He had several bags of takeout Chinese food hanging from his arms but still asked what floor we wanted, punching the top button when my wife replied. We moved to the back, still arm in arm, as the box surged upward. The guy got off at the fourth floor and before the doors had finished closing Cass had me pinned against the wall with her mouth on mine, kissing me with hunger. I was oblivious to us reaching the top floor - didn't even hear the bell ding - until she left me gaping like a fish out of water as she broke free and exited the elevator. Still stunned, I shook my head for a moment or two and looked up to find her waiting outside the doors, crooking a finger.

"You're going to want to follow me."

With that she headed off down the hallway, leaving me to scramble out just ahead of the closing doors. I licked my lips as I watched her magnificent ass move within the tight confines of her dress, not even bothering to try to adjust the bulge under my skirt. As she reached the door at the end of the hallway she gave me a come-hither look over her shoulder that was in danger of activating the sprinkler system. Without a word she passed a keycard over the sensor and pushed the door open, tossing her purse aside as I followed her into a room with mirrors. Like, A LOT of mirrors. On the ceiling, on the walls, above the headboard... everywhere. We weren't even close to the bed yet and I could see numerous reflections of us and... damn. I could really get used to wearing stockings if they were going to keep making my legs look like this.

Cassie waited patiently while I goggled, an affectionate look on her face. When I finally stopped staring at myself she flashed her palms in all directions. "Welcome to the honeymoon suite! Your wonderful wife thought this might be the very best way to finish off your big evening and wow, isn't she a smart one?" She pointed to the right. "The bathroom is over there. Why don't you make use of it first?"

I nodded and started to move, but she caught my arm. "You'll need this," she said, tossing something shiny up in the air for me to catch. It was a tube of lipstick - since it was the lipstick I was wearing, I guess that makes it my lipstick tube - and after making the grab I bowed in her direction before heading off.