The role of a lifetime 03

A few days later on a warm and pleasant afternoon, Britt sat in the outdoor seating area of a local coffee shop, waiting for Natalia to arrive back with their drinks. 

He scanned his surroundings once more, taking note of the people around him and feeling very out of place. Opposite him sat an old couple, smiling and chatting about book one of them had recently read as the woman enthusiastically told the man about the story. Behind them sat a middle-aged woman, busily typing away on her laptop perhaps trying to meet a work deadline. To the woman's left sat a relaxed-looking middle-aged man who kept unnervingly kept looking over at Britt, making him feel very uncomfortable, as he failed to hide the fact he was checking him out. Britt tried not to make eye contact with the man, as he remembered Natalia telling him to expect some male attention dressed as he was, but knowing and experience it were two very different things, and being on the receiving end of the man's flirtatious looks was something very alien to him.

It had been over a week now, dressing as a woman, and although he tried to tell himself, it was no different to playing any other acting role, he still felt incredibly uncomfortable being out in public in the female clothing. Take the casual outfit, Natalia had chosen for him that morning, The denim jeans he wore were in a lot of ways similar to menswear, he had worn tight jeans before and this pair felt no different, except for the crotch area, that hadn’t been designed to accommodate the extra parts he had between his legs, meaning he had to tuck away his bits tightly between his legs to keep up appearances, leaving him with an eery feeling of pressure whenever he moved.

On his upper body, he wore a soft white blouse with a ruffle design on the shoulders, and a thin black belt cinching in his waist, again wearing the top was not too dissimilar to wearing a man’s short sleeve shirt, apart from the softer and thinner material was, and the protruding mounds, sticking out from the front, thanks to his padded bra beneath.  

But perhaps the biggest difference to the type of things he normally wore, were his shoes. The peep-toe black pumps surrounding his feet felt completely foreign to his male mind, especially not wearing socks, which Natalia insisted wouldn't fit his look.

It was a strange sight looking down and seeing his painted white toenails extending out from the open front of the shoes, not to mention the blocky heel at the back. It had taken him a few days to get used to walking in heels, struggling at first, but after a lot of practice and changing the way in which he moved his body, he found that albeit tiring, walking around on heels, like the one he currently wore, wasn’t so bad.

With everything considered, Britt though he was adjusting well to such a dramatic change to his lifestyle, he was no longer constantly fiddled with the wig dangling down at the sides of his head, which at first drove him crazy as for most of his life he had just had a shaved head.

He had also got used to the feeling of wearing makeup, he still had a long way to go in terms of applying it effectively, but a week after first having his face painted, he almost forgot he was wearing it apart from the occasional time where he left a colourful mark on the rim of a glass or wiped his mouth after eating, smearing lipstick across the back of his hand.

As Britt sat in the warm glow of the sun, waiting for Natalia, he started thinking about the picture she had sent to Victoria a few days earlier and wondered how the Jim and Victoria had reacted to his feminine image. They must have been shocked, he thought, hell, he had been knocked for six the first time he saw himself in the mirror that day after Natalia had made him up. He remembered standing in front of the mirror for what seemed like an eternity, examining every detail of his hair, makeup, and outfit, amazed that she could do such a good job of erasing his male appearance, without a massive amount of effort.

After dressing him up that day, they had gone out to eat at a top restaurant, Natalia telling him he needed to get used to being out in public dressed as a woman and to think of it as research for the part. 

That evening was Britt’s first experience of being out of the house dressed in women’s clothes and he remembered feeling incredibly nervous as he left the house, repeatedly looking left and right up the street, as he tottered quickly to the car on a pair of tall wedge heels than even after all his hours of practice, he still struggled to walk in. 

Entering the hotel lobby and standing next to Natalia as she asked the receptionist where their restaurant was, Britt had been terrified, fidgeting and twitching unnaturally and garnering quite a few odd looks butut after being seated at their table and sampling some of the delicious food on offer, he had relaxed and actually enjoyed the evening.

Britt looked up and smiled as he saw Natalia returning with their coffee’s, “I’m back, Gabriella, did you miss me”? Natalia said cheerfully, using the name of the character from the movie, he was preparing to audition for.

(See image 3.1)

“Well let's put it this way, I’m glad you’re back, It was a little scary sat here alone, dressed like this, especially with that man over there, who keeps looking over and smiling at me”, Britt replied. 

Natalia turned, “which man”? she asked.

Britt became a little flustered, “Hey, don’t look”, he said in a hushed voice.

Natalia turned back and chuckling before sitting down, “ha, I told you, hun, you need to get used to men looking at you, it’s part of being an attractive woman, now how would Gabriella react to him smiling at her”?

Britt thought for a second, trying to imagine himself as the 22-year-old woman from the movie script, “hmm, well she’s young and attractive, but also a bit shy and reserved having recently moved to the city from a small town, she would probably feel uncomfortable with the attention and try to avoid eye contact”.

Natalia squinted, “hmm, I’m not so sure, I think that's what you want to do, remember I’ve read the script too, and have been thinking about her longer than you, yes she’s new to the city, and a little introverted, but she has also had her fair share of relationships back in her hometown, I doubt she would be as shy as you make out”.

“So how do you think she would react to a stranger smiling at her”? Britt asked.

“Well, that depends, is he attractive”? Natalia shot back.

Caught off guard by the question, Britt got a little flustered, “I…I... don’t know, Vic, I don’t think of men in that way”.

“Well, you aren’t thinking like Britt now, are you? You’re a young attractive woman called Gabriella, would Gabriella find him attractive”?

Britt glanced across the outdoor patio and studied the man, tall, athletic, nothing too unusual about him, dressed smartly. He turned back to Natalia, “yes, I guess, she might”, he said cringing.

“Ok then Gabriella, the next time you catch his eye, I want you to give him your warmest smile, look him directly in the eyes and hold your stare for three seconds”, Natalia replied.

“Really? I can’t do that, what if he thinks I’m interested in him and comes over”? Britt said worriedly.

Natalia smiled, “you are interested in him Gabriella, you just said he’s attractive, you’re new to the city and don’t know many people, if he comes over, talk to him, and if he asks for your number give it to him”.

Britt looked down stunned, he picked up his coffee, sliding his white nails through the handle, picked up the cup and taking a sip, with no intention of looking in the direction of the man’s table again for the duration of their outing.

He was about to change the topic of the conversation when Natalia’s phone beeped. She picked up her handbag from the chair next to her and located her phone. Unlocking it she just stared down with a blank expression on her face, as Britt looked on confused.

“What’s wrong”? Britt asked.

A smile crept back across Natalia’s lips, “you won’t believe this, it’s from Victoria, listen to what she's got to say”, she said, before proceeding to read the message aloud, “Hi Victoria, thank you for messaging me, and the picture you sent, Britt looks lovely in that outfit, did he choose it himself? Sorry about the message last week asking to cancel the bet, I don’t know what we were thinking, I mean why on Earth would we cancel when Jim’s going to wipe the floor with Britt, let’s catch up soon ok? Toodles”.

Britt smirked, “so much for him quitting them, he never could back down from a bet, even when he knows he was going to lose”.

Natalia shook her head and passed her phone across the table, “Well, I wouldn’t be so sure about that, Jim looks like he’s playing to win!”

Britt took the phone from Natalia and looked down, as the smile on his face quickly disappeared, “Holy shit", he cried out, almost falling off his chair.

(See image 3.2)