(Author’s Note: Moving forward, assume Chris is speaking in his feminine voice unless otherwise noted. I imagine the italics would get old really quickly if I did that for the whole story!)
Part Twelve
Less than an hour ago, Chris would not have remotely entertained what his cousin was suggesting.
Thanks to how Amy had strung him along step by step, however, it was impossible to refuse this latest demand. No matter what he said or didn’t say, she had already captured the image of him wearing her shorts and bra. That was on top of the picture(s) she already had of him wearing panties. If he had known she was going to take things this far, he might have considered saying ‘no’ at the beginning. The blow to his reputation would have been painful, but at least he wouldn’t have to deal with what ended up being so much more leverage than she had started with.
Now that he was in this deep, it felt more and more like the only way out of all this was by pushing through. He had already shaved his whole body, and Amy had made it pretty clear that she planned on dressing him up like a girl from head to toe. Once she was done with all the listed things, he would demand that she follow through on her end. In the back of his mind, he knew that going along with the feminine transformation was a bad idea, but he couldn’t think of any other solution while currently being put on the spot.
“My name is Chrissy,” he reluctantly said, committing to the higher tone, “I want to- wear a dress . . . ” It sounded even worse out of context, which is why he hesitated. Putting on a dress was supposed to be a penalty for if he couldn’t keep the voice up. Not something he actually wanted to do. Although that was true for literally everything Amy was pushing on him.
“Well, duh,” Amy giggled, “You may think you hide it well, but I’ve always known you’ve secretly wanted to be a girly girl. Don’t worry, Chrissy. I can make your wish come true! Now, sit.” She gestured to the chair by her desk.
Opting to ignore her completely off base reading of his hidden desires, Chris focused on the exterior matters at hand. “Can’t I-” he started, before clearing his throat to make sure the feminine voice was just right, “Umm, a tank top?” There was no good way to say it.
With a small smile, Amy clarified what he actually wanted. “What, you don’t want to sit around in just your bra? Chrissy, this is what girls do. We’re a lot more comfortable around each other than dumb boys. Besides, your padding hasn’t arrived yet, so you’ll just have to be patient.”
What did that mean? “Amy-”
“This is just going to take longer if you complain the whole time,” Amy pointed out, “Come on, have a seat. I need to get started on your nails.”
Chris had so much more that he wanted to say, though none of it would come across particularly seriously when he looked and sounded like he did. So he sat down. His cousin’s words were a reminder of his own justification, anyway. The sooner she was done having her fun, the sooner he could tell her to delete everything. Better to embarrass himself in front of his brat of a cousin than across his various social media platforms.
Still smiling, Amy said, “Wait right there, Chrissy. I’ll be right back.”
He was tempted to pilfer through her desk drawers on the off chance there was some dirt he could use to counter what she had on him, but Amy didn’t go very far. She started by turning on her bluetooth speaker in the corner and putting on some pop music in the background. It was some girl band that Chris may or may not have heard before; he couldn’t tell if Amy was playing what she liked or leaning into the ‘girl bonding’ thing.
She returned a minute later with a handful of things she haphazardly placed on the desk. A make-up kit, a pink hairband, and a vial of nail polish. “Bubblegum pink will be so cute on a girl like you,” Amy said. She took Chris’s hand and lifted it up to inspect. “Not terrible, I guess. Could use a bit of filing, but we already have so much to do. How about this? We can skip that step. IF you ask me nicely to paint your nails.”
She wasn’t recording this time, which made Chris more willing to suck it up and say what she wanted. Plus it was nearly as bad as echoing the false name and his interest in wearing a dress. “Please paint my nails, Amy?” he asked. Even in the female voice, it came across a little begrudging.
Amy just sighed. “We’ll have to work on that attitude, Chrissy. Try it with a smile this time. Bonus points if you can make it demure.”
Demure . . . ? Unlikely. Still, he forced the best smile he could manage under the mortifying conditions. “Paint my nails, Amy? Pretty please?”
“Better, I guess,” she scoffed, “Okay, hold still.”
Chris did his best to do just that, though he couldn’t help but fidget in the unfamiliar chair as Amy positioned herself for the job. She was leaning back against the desk, automatically taller than him due to being the only one standing. The two of them also weren’t touchy in the slightest as cousins. At most, they’d do an awkward side hug for the sake of acting happy to see each other when parents were watching. Now Chris had to deal with Amy more or less holding his hand as she got started on the first nail.
Rather than further taunting, Amy simply hummed to the music as she worked. One by one, she carefully painted each of Chris’s nails light pink. When she was done with the hand, she held it up to her lips and gently blew on his fingertips. After succeeding in making him feel even more uncomfortable than before, she placed his hand down on her thigh and told him to not move an inch.
There was nothing flirty or sexual in the slightest when it came to her approach. It was just a lot of gestures and contact that were completely opposite to their normal dynamic and proximity. At the same time, she clearly knew what she was doing with her latest move. Idly smirking at his hand’s presence on her bare leg, Amy began working on his second hand.
“Let’s do a second coat, just in case,” she said, “You do want your nails nice and pink, right?”
Chris just gave a small nod, until Amy told him to speak up. “Yes. Nice and pink . . . ”
“Good girl,” she replied.
Then she went through the entire process again, while Chris figured out after a couple songs that they were only listening to girl bands. Never quite getting comfortable with his palm resting on Amy’s thigh or the face to face position they were in, he mostly averted his gaze and impatiently waited for her to finish the job.
After what felt like forever, she signaled that she was done by guiding his second hand to her leg. “There. That wasn’t so bad, was it?” Amy asked, “Now, hold still for another minute or two. In the meantime, do you want me to do your make-up? If so, you know how to ask!”
He did, indeed. Once again forcing the awkward smile, he also willed himself to meet her amused gaze as he looked up at her and said, “Will you please do my make-up, Amy?”
“Of course, Chrissy. Your voice is getting better, by the way. Keep it up, and you might just be rewarded. Now then . . . ” She picked up the hairband off to her side, “Your hair is so boy-ish. I’m still not sure what to do about that. But this will work for now.” Not bothering to tease what was coming, Amy simply leaned forward and used the pink accessory to push his hair back. Adjusting it into place once it was settled behind his ears, she said, “Perfect. Well, not perfect, but good enough. And totally out of the way. Just have to grab my brushes!”
She opened her make-up kit and spent a minute or two contorted sideways as she pulled out a small collection of things. Her partially-seated spot on the desk probably wasn’t ideal for the coming task, but she seemed committed to standing over her cousin as she worked.
Meanwhile, Chris had shifted his attention to his hands. He had never worn nail polish before, and now they were thoroughly coated in a pink that was quite similar to the bra he was wearing.
And there was still plenty more to come.
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