The Task Pt. 01

Hi! This is my maiden voyage here. Please feel free to comment pro or con. This could have ended up in Romance, Erotic Couplings, Loving Wives, etc., but as per the guide in How To later chapters will be centered around Transgender/Cross-dressing so here we are. There is a good deal of heat to be found but not in the first few pages. Thanks for reading and future chapters will be posted in, well, the future.

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I knew I was doomed long before the final game had finished. Dead last in my fantasy football league had been all but guaranteed by a mid-season swoon that saw me dropping six games in a row. For most people that would just mean missing out on the playoffs and the chance to win some money but in our league, one made up of friends from college, there were consequences for coming in at the bottom.

You had to do The Task.

Warm lips pressed against the back of my neck as Cassie's arms slipped over my shoulders. "Is it true? Am I really married to the biggest loser of all?" The mirth in her voice made the corner of my mouth edge upward as she shifted, her breath now tickling my ear. "Alas, how shall I bear the shame of knowing that while my betrothed earns a great living and isn't too bad in the rack he is the dregs at picking other men to play a game well?"

"'Isn't too bad in the rack?'" I did my best to sound ridiculously offended. "Well, allow me to prove that incorrect." I spun in my chair, planning on scooping her up and carrying her off to the bedroom, but she eluded my grasp with a grace stemming from a childhood of gymnastics.

"Right now I'm off to work," she said with a playful grin, "but I will take a raincheck."

"Sure you don't want to be a little late? I could have you out of those scrubs pretty quickly."

"The problem isn't how long it takes for you to get them off me," she said as she bounced back in to give me a lingering kiss. "The problem is how long it takes before I'd be able to get them on again. I'll be back sometime after midnight unless my shift runs long, in which case I'll be back even later after midnight." The living room filled with the jingle of keys as she gathered up her things. "When do you find out about your toil?"

"It's The Task, not the Toil, and we're doing a Zoom tomorrow night."

"Fun! I'll be here! I hope you get something good!"

I grimaced as she opened the front door. "It's not going to be good," I called out. "It's The Task."

"I meant good for me!" she said before laughing. "Bye, Luke. I love you!"

The door closed on my echoing reply, leaving me with a semi-hard cock and the knowledge that even if my wife got home when she was supposed to she'd likely be too tired for shenanigans anyway. I tried not to take stuff like that personally - I knew how hard she worked as a nurse, especially now - but at the same time as we hit the seven-year mark in our marriage I couldn't help but feel like things weren't as great as they could be in the bedroom. Not that we were having problems or failures or anything, but rather that it had been feeling a little rote or by-the-numbers for the past few months. Still good, but not... you know. Exciting. Earth-shaking.

Cassie had assured me everything was fine but I'm pretty confident that if there were issues more likely than not they'd be on me. I was brought up in a very strict religious household and it's fair - more than fair, really - to say I was a wee bit naive when I escaped to college. I'd done some fooling around in high school but didn't manage to lose my virginity until almost the end of my freshman year at ASU - and the only reason I was there was because an academic free ride had allowed me to make my own choice of school and push back at the suffocating relationship I'd had with my parents. And while I did enthusiastically enter the world of the sexually active my taste had leaned towards women who were as vanilla as I was - I don't even know if I was consciously aware of it but I went from one monogamous relationship to another with partners who were content to keep it simple, so to speak.

Then I met Cassie, and my brain almost melted.

That was due to a number of reasons but probably most prevalent was her attitude towards sex - she liked it and wasn't afraid to say so. Again, to most of you this wouldn't be a big deal but I was raised to believe that intercourse was for making babies and nothing else and have no problem with the concept that my parents had never had sex again after my younger brother was conceived. I wouldn't be shocked if that had been an immaculate conception, truth be told.

Cassie was the first woman in my life - well, the only one - who didn't wait around for me to initiate sex. She was happy to suggest, or, more accurately, to demand. Not that I was unwilling, but I will confess it took me a while to get used to it and our early relationship almost didn't survive me needing to come to terms with her self-confidence. I know, it probably sounds ridiculous to you that I'd be even remotely put off by a gorgeous woman who brazenly said (and took) what she wanted but again, Bible-thumping parents and the lingering guilt they'd instilled. It was a near thing but I'm glad I managed to unclench enough for us to continue on.

That being said, I'm still not what you'd categorize as sexually adventurous. I'm trying - I really am - but more often than not the gentle nudges Cassie gives me in new directions either don't get acted on or go right over my head. Not everything - we've done some light bondage and spanking, for instance, but I know she's got to be somewhat frustrated. Not going to lie, I'm a little concerned. About her, about us, and about The Task.

Suppose I should elaborate on that a bit - The Task, I mean. Like I said the loser in our league pays for coming in last. At the beginning of each season we all send Preet - Darryl's our commissioner and Preet's his wife - an email with our version of what should serve as the booby prize. After the playoffs are over we do a Zoom call and Preet pulls one of them randomly from a bingo hopper. They can be pretty out there but there's a sort of natural check and balance set to the system - sure, you could say that the loser has to streak through a local park, but what if you're the loser and that one gets chosen? Two years ago Jasper had to wear Broncos gear to the bar he watched his beloved Chiefs from every Sunday; last year Vatch did 20 hours of community service in a soup kitchen (that was my suggestion, thank you very much). As I settled onto the couch and popped open my laptop I hoped mine got chosen again - 20 hours at Habitat for Humanity would do me good (and I did a few hours a month there with them anyway). I was mildly surprised when Cass plopped down beside me but happy to feel her body pressed up against mine as I prepared to learn my fate. As others signed on there was several minutes of congrats and good-natured ribbing before Darryl yelled to get our attention.

"Okay, okay, as much as it would be fun to drag this out and make him squirm even longer we should probably get to naming The Task before my kids remember that they haven't fought with one another for at least eight minutes now." His picture shifted as Preet popped into view next to him, hooking a bang of dark hair out of her eyes before waving at us.

"Hi, everyone! So good to see most of you," she said with a laugh. "Oh! Cassie! Hi! Thank you for the advice the other day!"

Cass smiled and waved it away with the air of a medical professional who does it all the time. "Glad to help, anytime."

"Scintillating stuff and all, but can we get to The Task already?" That was Jed - some people moved beyond being an asshole in college, while others just leveled up. "I want to see Loser Boy get mine and have to do the Cinnamon Challenge."

Darryl rolled his eyes while dragging one of those bingo hoppers into view. "Okay, okay, here we go." His voice took on the air of a game show host as he continued. "As usual, you can see I have bingo balls numbered from one to twelve - well, B1 to B12 if you want to be pedantic about it - which I will now dump into the spinner thing. Preet has your Task suggestions as sent in before the season started, which have been randomly assigned a number." Closing the door, he began to crank the handle and make the hopper spin. "She did not tell me who contributed what but in any case I am very, very happy not to be the one getting The Task this year because they all suck."

Cass gave my arm a squeeze as I grimaced. "Bring it on," I said with a noticeable lack of enthusiasm.

With a flourish Darryl gave the hopper a final spin before letting it come to a stop. "Preet? Would you like to pick?" Reaching across, his wife scrabbled around inside with her hand for a couple of seconds before pulling out a ball. Squinting a bit, she announced "B7!" before turning it so we could all see. Handing it to Darryl, she glanced down at a piece of paper on the table - we couldn't see what was on it but couldn't miss her eyebrows raising as she gave a low chuckle.

"Okay. Well. Wow. Luke, as the last-place finisher this year you are required to complete The Task as follows: you must post a video of yourself having a drink - an entire drink, not just a shot - in a bar." She paused for a second, the corners of her mouth twitching upwards. "Uhm, you must do this dressed as a woman."

Absolute bedlam reigned, Zoom style, while I sat there with my jaw dropped and my face reddening. Beside me Cassie gave a loud gasp, eyes widening as her free hand went to her mouth. Darryl called on the person who put it in to identify themselves but after a few moments of silence, during which nobody stepped up, shouting started again. I was stunned beyond speech. Who would have had the balls to put that in as something that could have fallen on them? How was I going to do this? What the hell?

Chaos still ensued online as, with no idea how else to respond, I closed my laptop and sat back with a shudder. What a nightmare! This was unfair and unreasonable and I had half a mind to quit the league instead of doing it, no matter how much fun it was each year. A deep sigh escaped me as I wiped at what may or may not have been tears beginning to well up at the corners of my eyes. I felt Cassie's arms sliding around my shoulders as she gave me an awkwardly-framed but extremely welcome hug. My chest hitched as a drew in a ragged breath.

"I don't believe this. How could this happen?" I twisted a little to face her. "This is nuts, right?"

She shrugged. "Whatever it is, it's what you have to do."

"I don't. I could, I could just leave or something."

Her lips twisted into a frown, dark eyes narrowing. "You could, but that's kind of shitty, don't you think?"

Another heavy sigh. "Ugh. Yeah, it is."

"That's not you," she said, giving me a kiss on the cheek. "You're bigger and braver than that."

"Am I?" I blew a raspberry. "I suppose I'll have to be." With a little wiggling I managed to snake one of my arms around her back. "I mean, I can just, you know, make it a big joke. Ridiculous wig, giant balloons as boobs, over the top makeup. Hit a place when they open in the morning, chug my drink... it'll be okay."

Cass drew back a bit and locked her eyes with mine. "You could do that. You could go that way." She paused for a moment, leaving something unspoken hanging between us.

After a few seconds I felt compelled to pick it up. "Or?"

She flashed me a brilliant smile. "Or you could fucking *own* it. Take it, run with it, and make it an absolute and total win."

My brow furrowed. "And how would I do that?"

Her eyes were aglitter, dancing with something I couldn't quite place. "Like I said, you own it. Lean into it. You embrace the challenge and crush it. Absolutely nail it."

I'm not the brightest star in the galaxy but I managed to figure out what she was saying. "Instead of making a goof of it you want me to... like, try to look good? Like an actual woman?"

"Yes, exactly." She tightened her grip around me. "I think we could have a lot of fun with it."

"We?"

"Of course. You don't think I'd let you face this by yourself?" Cassie brought one of her hands to the side of my face, caressing my cheek. "I know this is way outside of your comfort zone and you're angry and maybe a little upset right now. But I still think this 'task' is actually an opportunity in disguise. You need this, Luke. It'll help you branch out a little, to experience something new and alien and kind of frightening. You need this." Leaning in, she gave me a kiss before whispering, "We need this."

Oh. Again, slow on the uptake but not a complete dolt. Cassie... shit, the idea of me doing this was turning her on. Plus she seemed excited about it in general as well. The knot of dread that had gathered in my chest at Preet's announcement loosened a bit - not much, but some. "You really think so?"

She gave me a slow nod, an odd little smirk on her face. "Oh, definitely. We will make this experience a fantastic thing from start to finish."

A question jumped into my head and I started to ask it, decided it was dumb and stopped, but after seeing her quizzical expression figured 'what the fuck' and let it out. "Do you think... I can't believe I'm asking this."

"Ask, love."

I could feel my cheeks blazing. "I mean, do you think you'll make me, I don't know, pretty?" I dropped my head and rubbed at my brow. "I can't believe I just asked that," I muttered.

My wife's strong hand gently but firmly pushed my chin back up until we were eye to eye again. "Hey," she said, her tone silk wrapped around steel, "don't be ashamed to ask that. Don't be ashamed to ask anything." A smile played on her lips. "When it comes to something between the two of us you shouldn't be afraid to do or suggest anything. The worst you're ever going to hear is a 'no'." She shifted her hips a bit. "If this were erotica you'd emerge from my ministrations so gorgeous that you could easily win the Miss World beauty pageant. That, unfortunately, is not likely to happen."

"Oh." Why was I a little crestfallen about that? "I... okay."

Laughter fairly exploded out of her. "Look at you going from being a wreck about doing this to being concerned about how hot you'll be. You are absolutely adorable." Tilting her head, she looked me over for a moment or two. "In those stories the guy is usually like 5'6" or so, maybe 125 pounds. You, on the other hand, are a pretty big dude - 6'1", 195, right?"

"Hey! Not an ounce over 189, thank you very much. Well, on most days."

Her grin widened. "Sorry. Also your features are what are traditionally considered to be 'masculine,' although that line of thinking is pretty outdated." Her lips pursed as she turned my face first left, then right. "I think you'll end up more handsome than pretty, but that's not a bad thing. I think 'attractive' is a given."

I was shocked at how much that prediction mollified me. This was INSANE. And yet, here we were. "I'll put my faith - and my face - in your hands."

"That's not all you'll be putting into my hands," Cassie said, waggling her eyebrows. "But in all seriousness, I need to know that you're going to both commit to this and be willing to let me call the shots." She grabbed my hands and gave them a squeeze. "I know this is scary for you - absolutely terrifying, I imagine. But this is a great way to give double middle fingers to your upbringing. And to your parents, who fucking deserve it."

No argument from me there. Getting some space from my mother and father had allowed me to be able to comprehend how toxic and controlling they were. Doing so had only made them angrier and more domineering, which reached a boiling point when first I introduced them to Cassie. Not only was she not the quiet, subservient little Evangelical church mouse they'd expected me to spend my life with but, even worse, she wasn't white at all! How dare I bring home a woman who was GASP both black AND Puerto Rican? They acted like I'd spat into their faces. I'd just stood there, paralyzed by a lifetime of knuckling under to their cruelty, but Cassie was strong enough for both of us. She let them have both barrels of her righteous fury before pulling me back to our car and speeding off. I think we were a good ten miles away before I was able to speak and once it hit me what had happened, there was no thought of going back. We'd sent them an invite to our elopement but never heard back. That wasn't a surprise.

And she was right. It *was* scary for me, all of this. I'd always been resistant to trying new things sexually - old habits die hard, I guess - and this was so far out of my comfort zone it was in a different galaxy. The thought of being essentially powerless, well, I'm not going to lie, that was freaking me out as well. Maybe I wasn't as bad as those who'd raised me - hell, I definitely wasn't - but I wasn't so myopic that I didn't see shadows of them still within me, still responsible for the way they'd shaped me. Maybe I wasn't a control freak like they were but wanting my world and everything in it to be neat and orderly, the way I felt the most comfortable, well, that was trying to exert control, wasn't it? I was probably fortunate Cass hadn't gotten fed up and bolted at some point after being stifled by me and my rigidity. Well, maybe not the good kind of rigidity, but you know what I mean.

I drew in a long, deep breath, holding it for a few seconds before letting it hiss out of me. "Yeah, you're not wrong about them. I can't believe these words are coming out of my mouth but I think you might be right about this - about it being a good thing for me. For us." The warmth coming from her smile gave me the courage to ask another question I wasn't sure I wanted to know the answer to. "I'm glad you're excited about it but - " my voice cracked a little - "does this mean you're, you know, bored with our sex? I mean, I love it but I get if you -"

Cass shut me up by pressing fingers against my mouth. "No. There is nothing wrong with the sex we have, Luke. It's wonderful. But sometimes different can be wonderful too." She looked down and gave her lips a quick lick. Untangling herself from me, she hopped to her feet and grabbed one of my hands. Giving it a tug, she said, "C'mon."

Pretty sure I was going to like where this was going. "And what do you have in mind, miss?"

She jerked her head toward our bedroom. "Showing you all about 'different.'"

She didn't have to ask twice.

Once there I made use of the bathroom while she started pulling open various drawers. When I emerged she greeted me with a large smile and zero clothing, allowing me to appreciate her generous curves. Some guys like the stick-thin supermodel body type and that's cool for them and all but I am partial to the swells and valleys that make up Cassie, as evidenced by the growing bulge in my shorts. I reached for her but she stepped back and waggled a finger at me, her grin widening.

"Slow down, big fella. I'm the engineer for this train, remember?" She raised her other hand and I saw what was dangling from a finger - the fancy blindfold we'd used once or twice before. She twirled it a few times while looking me up and down. "Why don't you make yourself useful and get rid of your clothes? They're just going to be in the way."

It's pretty unlikely that there's an Olympic event for stripping off your own clothes but if there were I would have been on the medal podium with at least a silver. By the time I tossed my underwear over my shoulder my cock was clearly interested in what was going on. I reached for Cass again but she gave my hand a playful swat before pointing at the floor.

"On your knees, boyo." At my hesitation she rolled her eyes and said, "I need to put the blindfold on and you're too damn tall while standing up. I'm not going to make you crawl around on all fours and bark like a dog or anything." She paused. "Not tonight, anyway. Paws to yourself for now."