The role of a lifetime 02

Victoria woke the next morning, hungover and alone. pushing off the covers, she swung her legs over the side of the bed and placed her hand against her aching head, regretting drinking so much the night before, and situation it had led to. Standing up gingerly, she found her dressing gown on the back of a chair, and after wrapping it around her toned body, she left the bedroom and descended the stairs to look for Jim.

She found him in the living room, sat in the dark, staring blankly at the back of the menu for Mr Wang’s, having read through the drunken contract she had written on the back so many times he had lost count.

“Did you sleep at all”? Victoria asked yawning.

Jim slowly turned his head and squinted his bloodshot eyes, trying to focus, “Victoria, what the hell, did I agree to last night”? he groaned loudly, shaking the leaflet in his clenched fist.

“Something fucking stupid as usual”, Vitoria replied walking towards him, “I told you your stupid bets were going to get you in trouble one day. You and your fucking male ego”.

“Hey, this is not all on me, you were just as bad as me, and it wasn't me who wrote this fucking contract”, Jim said angrily tossing the leaflet onto the table.

Vitoria sat down and sighed, “It’s that prick friend of yours and his bitch of a girlfriend, they just make me so angry, always acting superior and thinking they’re better than us, and yes, I wrote the contract, but no one forced you to sign it, that’s on you”.

The room fell silent for a moment as Jim absorbed what she had said, “Is it binding”? he asked, already knowing what she was going to say.

“Unfortunately, yes, there are two copies, signed and witnessed, it would hold up in court”, Victoria answered shaking her head”.

“Fuck”, Jim exclaimed, pausing for a moment to think before turning to face his girlfriend, “I can’t do it, Vic, I’ll just concede, Britt can have the money, we don’t need it anyway, I built one company from the ground up, I can do it again”.

“Oh no, no fucking way, are you giving away our future to that arsehole, you may have built that company, but do you realise how much I've had to sacrifice? All the late nights and weekends, hardly seeing each other, the scrimping and saving. Until recently, do you realise we hadn’t had a vacation in two years, I’m not going through that again and having fucking Britt and princess Natalia laud it over us, if you want to start again, you’re doing it on your own”.

“Seriously, you would leave me”? Jim replied, completely blindsided by her response.

“As I said, Jim, I’ve supported you for years, so that we could build a future together and now you’ve risked it all on a stupid bet.", Victoria yelled angrily, "You find a way to fix this, and do it without giving them a penny or I’m walking away”.

There was again a moment of silence in the room, as they sat side by side both in deep thought. Five minutes past before Jim turned to look at her once more, “perhaps I can talk to Britt, I’m sure he’s feeling just as bad as me, he probably woke up this morning regretting that happened, if I talk to him, I’m sure I can get him to rip up the contract”, Jim said hopefully.

“I’d say that was an excellent plan, how about we have some breakfast, and you text him, see what he says”, Victoria said in a calmer voice as Jim nodded in agreement.

After forcing down some cereal, Jim picked up his phone and drafted his message, “hey mate, crazy night last night huh? I guess we were all a bit drunk and got a little carried away, I’m sorry if Vic and I offended you guys in any way, let's just forget about than silly bet, yeah? Do you want to meet up later in the week? Shoot some pool”? After reading over it twice, Jim pressed send, placed his phone face down on the table, and sat back in his chair as the agonizing wait for a reply began.

By early evening Jim still hadn't received a reply, which was out of character as Britt usually replied to him straight away. Picking up his phone again, Jim typed another short message, “Hey mate, everything ok”? Again there was no reply as Jim and Victoria spent the rest of the evening watching a movie, not really speaking and too preoccupied to follow the plot.

Two days later, having sent another three messages with no response, Jim and Victoria were sat watching TV in awkward silence when the familiar sound of a message arriving, rang out through the room. simultaneously, Britt and Victoria looked down at the table in front of them, their eyes focused on the source of the jingle, Victoria’s phone.

Victoria leaned over and picked up her phone, using her fingerprint to unlock it, before stared down at the screen with a horrified look on her face, “who’s it from”? Britt asked nervously.

“It’s from Natalia”, She replied solemnly, continuing to read.

“And”? Britt asked impatiently, “what did she say”?

“Read it yourself”, Victoria said looking glum, passing the phone over.

Britt took the phone and looked down at the screen as his heart sank, “Hey Vicky, how are you? Sorry, we’ve been MIA for the last few days, but we’ve been busy organising things. Britt wanted to text himself, but he didn’t want a fight, but you can tell Jim, there is no chance we're cancelling the bet, Jim’s already been working so hard to get into the mindset of the character, there’s no way we can lose, perhaps you should just quit now and save yourself the embarrassment, anyway speak soon, toodles”.

Jim dropped the phone on his lap and placed his head in his hands, “so much for feeling as bad as you”, Victoria remarked.

“This can’t be happening, Vic, what are we going to do”? Jim asked.

“Well, you’re not conceding that’s for sure, what we’re going to do is head upstairs and try out a few things”, she replied.

“You mean... like... dress up”? Jim said forcing out the words.

Victoria nodded, “Exactly, we need to see if we have any chance of making this work”.

“I don’t know, Vic, I have a bad feeling about this”, Jim replied.

“It's too late to feel sorry for yourself now, Jim, you gambled with our future, the least you can do is show a bit of that competitive spirit you're usually so full off, stop acting like a loser and put up a bit of fight”, Victoria answered with a forceful tone.

Jim looked up, “ok, Vic", he mumbled",  I guess we could at least see what I look like, what do we have to do”?

Four days later

“Jim, can you come down here for a minute”? Victoria shouted from downstairs.

“Ok, coming”, Jim yelled back from the bedroom, where he had been watching some YouTube videos, trying to avoid Victoria as he felt incredibly embarrassed and emasculated in her presence. 

He looked down and grimaced, seeing a tight black material wrapped around his compressed legs, and shook his head gazing upon his flat crotch area, where his usual bulge had been painfully strapped back and hidden inside the panties, he wore beneath his leggings.

He got to his feet, feeling the pinch in his toes, and the still unfamiliar angled position of his feet, stuffed inside a pair of Victoria’s wedge pumps. Leaving the bedroom, Jim approached the staircase, where he stopped and took a deep breath, knowing he’d need to tread carefully if he was to avoid another slip like a few days ago. He pressed his back up against the bannister, gripped it tightly with both hands, and placing one foot at a time, he tentatively made his way down, too scared to move from his sideways position.

Reaching the bottom, he let out a sigh of relief, having made it safely down in one piece. looking up to see Victoria waiting for him in the hallway.

(See image 2.1)

She smiled upon seeing him, “you’re moving a lot better today, are you feeling a little more comfortable”? she asked.

Jim just glared at her, feeling ridiculous, dressed in her clothes, with a long dark wig sat on top of his head, “I don’t think I’ll ever feel comfortable dressed like this”, he replied pouting.

Victoria smiled, “oh, come on, that outfit is not much different to the stuff you normally wear, those leggings are just like your tight jeans, and the rest is just a T-shirt and a denim jacket”.

What about the underwear”? Jim asked looking down at the small mounds, pushing out of from the front of his T-shirt and feeling pressure between his legs.

“Ok, that I guess must feel a little new, but you'll get used to it, who knows? You might even come to like the silkier material”.

Jim looked at her astonished by the comment and feeling slightly embarrassed thinking about the silky navy-blue bra and panty set with the frilly edges, hidden away below Victoria’s clothes, which he was currently wearing, “Very unlikely, you and I have a different part down there, and you can’t imagine how uncomfortable it is having it tucked up between my legs”.

“I know honey, and I know you’re really trying, perhaps later we could let out Mr happy for a little exercise”?

A smile formed on Jim’s lips, as he felt a tightness in his groin followed by a small jolt of pain, “sure thing babe, your man is ready and eager to please, how about I go change now and take a shower,  you can come and join me in a few minutes”, Jim replied enthusiastically.

“Not right now, we’ll save it for later, first we need to talk”, Victoria replied in a more serious tone.

“Talk, about what? Has something happened”? Jim asked concerned.

Victoria looked him in the eyes, “Well, you could say that, let me ask you how are you getting on in those pumps”?

“What? These shoes? They’re awful, my ankles are aching, and can walk for 30 seconds without tripping over, but why are you asking about them now”?

Victoria pulled her phone from her pocket, “well, take a look at this, it looks like Britt and Natalia have really committed to winning this bet, I think we’re going to have to up our game a little, starting with some higher heels”.

Jim looked confused as she thrust her phone into his face, where he looked down confused at a picture of a smiling woman.

It took him a second to realise who he was looking at until something clicked in his mind as his eyes widened, and his mouth dropped open, “shit, no way”, Jim muttered.

“I know, crazy right? Looks like Britt's been working on his look a little more than you”, Victoria answered.

“Oh, this is bad, how am I supposed to compete with that”? Jim stated, looking down and not believing his eyes, seeing his old friend, out in what looked like a hotel lobby, dressed in a tight black one-piece outfit, perched on towering wedge heels, which made his own look like child’s play.

(See image 2.2)