ds1000
patreon
The role of a lifetime 07
🕑 Added 2021-02-12 22:20:01 +0000 UTCEarlier than evening.
“Are you sure I look ok”? Britt asked Natalia as he looked at his feminized image in the bedroom mirror.
“You look gorgeous”, Natalia responded from the next-door bathroom, as she finished applying her makeup, “what’s the problem”?
“I don’t know”, Britt replied despondently, “don’t you think this outfit is a bit flashy”? He asked, looking down at his shiny legs encased in sheer hose and the baby blue flared mini skirt wrapped around his waist.
Natalia stepped out of the bathroom and shook her head, “Flashy is what we’re going for, remember? Have you forgotten who you are? Tell me your name”?
Britt sighed, “Do we have to do this again”? he moaned, tired from having to constantly be in character, 24 hours a day.
“Yes, we do, as it seems, you’ve forgotten, now tell me your name”? Natalia demanded.
Britt turned on his tall cream coloured patent pumps and flashed her a smile, “I’m Brittany Anne St’ Clare”, he replied in a high cheerful voice.
Natalia nodded, “And what’s do you do to make a living, Brittany”?
“I’m an actress and model”, Britt replied happily.
She nodded again, “And what’s your dream”? Natalia asked walking towards him.
“My dream is to be famous and have people all over the world know my name”, Britt said confidently, having rehearsed the answer many times.
“Good”, Natalia said happily, “final question, why is important to always dress sexy and look your best”?
Britt looked back at his reflection once more, his plump pink lips shinning back at him from under their generous coating of gloss, and his eyes sparkled, looking sexy and alluring under the feathery fake lashes glued to his lids, “I need to look my best, so people notice me. Looking sexy will open doors and create opportunities for me, helping me to achieve my goals”, Britt announce feeling foolish as he shuffled his feet inside his towering heels.
“Exactly”, Natalia announced, “now let's hear no more complaints, it’s almost time to go and I still have to dry my hair, we can’t all just throw on a wig and be good to go”, she said before putting and heading back into the bathroom.
Having taken a taxi, Britt and Natalia arrived early at Bar No.7 and found a free spot to sit by the bar.
Natalia smiled seeing her former macho chauvinistic boyfriend struggle to lift himself onto the tall bar stool without exposing his panties to the group of men stood opposite, who had been staring at them since the teetered in through the door.
“What”? Britt remarked, seeing Natalia grinning at him.
(See image 7.1)
“Oh, Nothing, just admiring your beautiful figure in that sexy outfit, now what do you want to drink, Brittney”? She replied gesturing to the barmaid.
Britt rolled his eyes, ignoring the remark, “I’ll take a vodka spritz”, he replied, placing one of his aching feet on the footrest of the stool and hoisting himself up before shuffling around on top trying to find a comfortable position.
Feeling exposed and on show, perched awkwardly with his shiny knees pressed together, Britt looked over towards the door waiting for Jim to make his entrance. He thought back to the previous week and remembered how awkward Jim had been out in public dressed as a woman. He didn’t enjoy these outings himself, but at least he felt happy knowing he was doing better than his old friend.
Picking up his drink and taking a sip, Jim saw his inflated lips wrap around the straw provided, and wondered if he had gone too far in getting the facial fillers. He had been reluctant at first when Natalia suggested them, but having been convinced they were temporary and for the best, he caved in and gone along with the idea.
Seeing the door open out of the corner of his eye, Britt glanced over and did a double-take, not believing what he was seeing, and if it wasn’t for the fact, he knew he would ruin his makeup, he would have rubbed his eyes in disbelief, as the sight before him was utterly unbelievable.
It was Victoria he recognised, even with her out of character-heavy makeup and sexy outfit, but as she sauntered towards him, it was the dark-haired beauty with the resting bitch face, confidently walking by her side, that made his jaw drop open in surprise.
“Hi Brittney”, Jim announced cheerfully, as he tottered over on his sparkly boots and planted a kiss on Britt’s cheek, leaving behind a red lipstick mark on his cheek”.
“Uhm… Jim.”, Britt muttered, dumbstruck as he blankly stared at his friend's altered face, amazed by the size of his lips that wouldn’t look out of place on a blow-up doll.
“Who’s Jim”? Jim replied giggling”, I’m Jem silly”.
“Yeah, sorry, Jem, you look so…so...”, “pretty”, Jim said finishing his sentence for him, “well, I saw you looking so hot, on you’re Instagram, and couldn’t resist getting a little filler myself, what do you think, do I look as hot as you"? He added giggling once more.
“but… but… I”, Britt trailed off not knowing how to respond to the bubbly sexpot who was acting nothing like his old friend.
“Jem, come and say hello to Natalia, and show her your new hair and nails”, Victoria announced having just greeted Natalia who was looking just as surprised as Britt.
Jim stepping over to Natalia sat on the adjacent stool, flicking his hair with his right hand before fanning out his fingers to show her his set of acrylic extension, "Hi Natty", Jim sang out in a high cheerful tone, "Yeah, I guess I decided to update my look a bit, this long hair has taken a bit of getting used to but its so worth it, the way it looks".
"Yeah, I can see that", Natalia said awkwardly, studying every little detail of the feminized man in front of her, unable to hide her frustration, as Victoria smiled on from behind, loving the fact, she had finally managed to render the bitch speechless.
“You mean that’s not a wig”? Britt asked with a shaky voice.
Jim spun around and moved back towards him, “Eww, a wig, why would I wear a wig”? Jim announced fluffing up his hair once more and pouting, “oh sorry, that was, like, really insensitive of me, you still have that icky boy hair under that thing on your head, right? Sorry babe”. Jim said reaching out to take Britt's hand.
Britt recoiled in horror, almost falling off his stool as his high heeled feet flailed about wildly as tried to regain his balance, “what the hell was happening”? he thought to himself, feeling as if he had suddenly been transported to some alternate reality. This was not how the night was supposed to play out, he was the one who was supposed to be causing the shocks, but Jim with his new look and persona had blown him out of the water
Having steadied himself on his stool, Britt reached out to grab his drink from the bar, tossing the straw to one side, he picked up the glass and gulped down the remainder of his Vodka spritz before slamming the glass back down on the bar, “I’ll take another one”, Britt announced to the passing barmaid, knowing it was going to be a long uncomfortable evening.
The following week was a tense one between Britt and Natalia, with the couple bickering and arguing continuously.
Britt for the first time was actually doubting if he could win the bet as his mind kept fixating on the evening in the bar, still not able to comprehend the perfect girly girl act Jim had put on, not only looking completely natural in his movements but perhaps more shockingly, not slipping out of character once all evening.
Natalia, on the other hand, had reacted to the events of that evening in a different way, becoming even demanding and harsh, she was pushing Britt even further down the path to womanhood.
“Are you going to ignore me all day”? Britt asked Natalia, as she walked past him without making eye contact.
Stopping and turning slowly, she glared at him, “Yes, if you’re going to just roll over and quit, like a loser, you’re not the person I thought you were, and I don’t want to associate myself with a loser”, she spat angrily.
“Roll over, you’ve got to be kidding? look at me, Nat? I went with you to the salon, I let you convince me to get this hair and these god awful nails. What more do you want from me”? Britt exclaimed, taking a handful of his extended hair and clutching it tightly between his acrylic nail extensions.
“It’s not enough, I told you what you need to do? She announced firmly, “But your macho pride is getting in the way, it's going to leave us penniless”.
“Macho”? are you crazy? Nothing about me right now is macho”, Britt said annoyed, “you really expect me to get surgery, it’s going too far”.
Natalia stamped her foot angrily, “too far”? she cried, “for fuck’s sake Brittney, we’re talking about 25 million pounds here, it’s a simple procedure, you’ll be in and out in a day, and you didn’t complain when I had mine done last year”.
“I know, but that was different, I can’t do it,”, he replied confused.
“You’re scared”, she announced.
“I’m not scared”, Britt replied quickly, “it would just be too weird”.
Natalia took out her phone and scrolled through, before thrusting it into Britt’s face, “you need to get your head back in the game, what would you prefer, having breasts for a few months and feeling a bit weird as you put it or lose this bet, along with everything we own and go back to being poor. Do you think he is going to back down”? she said tapping the screen.
Britt looked at the picture on the outstretched phone, seeing an extremely thin-looking Jim sat on the top of a bench, wearing a tight white top, and a leather mini skirt. He was looking at the camera posing, having raised one of his feet on to the armrest of the bench and was balancing his foot precariously on one of his sky-high heels, while clutching his nylon clad knee, showing off his long white nails.
(See image 7.2)
Britt reached up, raked his long nails through his long blonde extended hair and breathed out a heavy sigh. He hated to lose and the thought of Jim winning this bet, the biggest bet they had ever had, filled him with anger and frustration, “they’re easy to remove, right?", he asked looking up at Natalia, "I mean once we win”.
Natalia smiled, knowing she had him, “of course, babe, super easy”.
