Okay, new idea that won't leave me alone. I don't really know much about crossdressing or professional makeup and modeling, so this is very fictional.

Playing Second Fiddle to Himself: Chapter 1

By: Mizzlizdiz


Isaac took one last look in the mirror, checking his hair and makeup as he always did before leaving his boyfriend's apartment.

When he was dressed and decked out as he currently was, he was Isabella, the face of Sassy makeup. He had been the spokes model for the company for 5 years and he'd been the lover of the owner of the company, David, for almost the same amount of time.

He hadn't always had an interest in crossdressing, it wasn't until after he met David that the idea had even occurred to him. David had been the first person to put makeup on him and had been the one to encourage him, first with women's underwear, then eventually into a dress. At first it had seemed so strange, but now it was routine. Now dressing as a man felt foreign.

It was a rather large transformation from Isaac to Isabella. As Isabella, he wore blue colored contacts, a flowing blonde wig, false eyelashes with eye shadow, eyeliner, mascara, blush, and his lips were always glossed. He had always been rather slender and willowy, so finding woman's clothing that suited him wasn't that much of a challenge, as long as it wasn't too low cut. Isaac hadn't gone as far as having surgery.

Isaac strode through the building, his high heels clicking the steady beat of his walk as he went. He had a photo shoot, one that he'd been looking forward to for months now. It was for a new line of makeup under Sassy that was going to be called Temptations.

He entered the area reserved for the photo shoot only to find that the photographer was already taking pictures.

A buxom brunette woman was currently modeling in front of the camera, with Mike, the photographer, yelling encouraging comments.

Isaac stormed up to him. "Mike, what's going on?"

"Sorry Isabella, I'm just doing what I was told to. You'll have to talk to the boss," he continued to snap pictures.

Isaac resisted the urge to begin screaming, and headed to David's office. He stormed past David's secretary, who feebly attempted to stop him.

"What is going on?" He slammed a hand on David's desk.

"Isabella, how are you?" he answered calmly.

"What? That's all you say to me? There's a woman doing MY photoshoot downstairs and I want to know why!"

"There's been a change in the image of Sassy makeup."

"Change? I have a contract! You can't change it until the end of the year!" Isaac protested.

"Oh, you'll still have some photo and press opportunities and you'll be compensated. But we feel that for the new line, we need a new face."

"You can't be serious? David, baby, what the hell?"

David's nose wrinkled. "Oh yes, also, I'll need you to remove all your things from my penthouse by this Friday."

"What?" Isaac's voice was small, barely a whisper.

"It's been fun, but really, you knew this wasn't going to last."

Isaac was frozen in shock and speechless. Was this some sort of twisted nightmare? He was getting the boot from his job and dumped in the same millisecond? He couldn't believe that this was really happening, that this cold man in front of him was his lover. He hadn't even seen a hint that any of this was coming.

"Now, if that is all, I'm late for a meeting." David stood, waiting for Isaac to leave.

"I…You are serious."

David sighed and rolled his eyes. "Yes. Now please leave."

Isaac didn't know what else to do so he went to his little office slash changing room. He sat at his desk, dazed. He couldn't wrap his mind around what just happened.

There was a knock at his door. He looked up to see the tall frame of one of the personal assistants, Jared, in the doorway.

"Hey Isabella. I brought you a latte. That's what you drink right?"

Isaac nodded. "Thank you. Where's Anna?" Anna was his regular personal assistant. She had worked with him since the beginning of his career and was his best friend in the world.

Jared appeared uncomfortable, shifting his weight nervously. "Anna is working with Lauren now."

"The woman in the photoshoot?"

Jared nodded.

"Great. I can't even keep my PA? Can this day get any worse?" Isaac put his head in his hands, frustrated.

Jared stepped closer and put his large hand on Isabella's shoulder. "I'm not sure what's going on, but I'm going to be here from now on, whenever you need me."

Isaac blinked rapidly, trying not to cry. Jared handed him a tissue.

"Thank you Jared," Isaac spoke softly.

Jared gave him a small smile, "I know you're not real excited to be working with me, but I want to tell you that I'm excited. I'm going to do my best to make everything easier for you. Anything you need just let me know okay?"

Isaac nodded.

This was the longest Isaac had ever spoken to the other man, and surprisingly, he was comforted by his presence.

Embarrassingly enough, Isaac didn't think he'd ever spared the other man more than a glance. It was a shame that he hadn't. Jared was an attractive man. He was tall, over six feet tall, and seemed pretty built. He had floppy brown hair and chocolate brown eyes.

"Hey Jared?"

"Yeah?" Jared seemed eager for whatever Isaac was going to say.

"Is it okay if I take a half day today? I need to take care of some things."

"Let me double check your schedule, but I think it's okay," Jared began to type into his blackberry. "Looks like you'd be fine Isabella, um… even if you wanted to leave now."

"Okay." Isaac paused. "If you're my personal assistant now, you take the time off too."

Jared looked surprised. "Are you sure? I could try to see if your agent can get you some interviews or signings or meet and greets."

"It's fine Jared. Take a break okay?"

Jared smiled and listened to him.


Isaac went straight to David's penthouse.

Maybe David just wanted some space. Isaac figured that he would do what David asked, give him some space, then see if he wanted to have dinner later in the week to talk.

Isaac was still reeling from that morning's events. It was all so sudden and felt like it was without any warning. He was thrown and still in mid air. He figured that this would be the best course of action, to follow what David wanted.

He packed up his suitcase, gazing around the apartment. He couldn't imagine not staying there anymore. He had hardly even been to the apartment he rented for himself. David's place was more of a home than his own. It was kind of a dramatic thing to have to leave a place that he'd found comfort and love, or so he thought.

He placed the key on the table and locked the door, closing it for the final time.

Isaac hailed a cab and headed to his apartment. It had been months since he was even there. It felt like a strange place. He unpacked his suitcase.

Walking through his apartment, he realized he didn't have anything there, no food or drinks, no shampoo, no toothpaste, things that he shared with David.

He sighed and hopped into the shower. Guess he had to run errands.


One of the good things about being a cross dresser was that when Isaac dressed as a man, he was never recognized in public. His natural hair color was red, his eyes grey, and without makeup, his face was dramatically different. Not to mention, wearing jeans and a t-shirt looked a lot different than a dress.

So Isaac ran his errands, comforted in his anonymity.

While he was grocery shopping, he heard a quick intake of breath and glanced up to see Jared looking at him with a strange expression on his face.

Dear God, please don't recognize me, ran through Isaac's head.

"You…" Jared paused.

Isaac was about to admit defeat and ask Jared not to say anything when Jared said:

"You are the most gorgeous man I've ever seen."

"Excuse me?" Isaac was surprised.

Jared grinned. "I know, it sounds like a cheesy pick-up, but I'm being serious. I'm Jared. What's your name?"

"Are you making fun of me?" Isaac snapped, his eyebrows drawing together in a frown.

Jared's smiling expression faded. "Oh. I'm sorry. You don't like men? I'm usually pretty good at picking up on vibes. I'm sorry."

He moved to leave.

Something made Isaac stop him. "I'm Isaac."

Jared smiled a big beaming smile at him and offered his hand to shake. "I'm Jared. I'm sorry about the lame ice-breaker, I just had to talk to you."

It seemed that Jared truly didn't recognize him.

Isaac found himself smiling back. "It's ok. I'm sorry I overreacted." He paused. "I've been having a strange day."

"Would you want to get a coffee and talk about it?" Jared offered

"We don't even know each other."

Jared looked a little sheepish. "I kind of want to know everything about you."

Isaac stared at him a minute, before answering "Okay." Surprising himself, but pleasing Jared.

Jared was beaming at him excitedly. "That's fantastic."

They agreed to meet at a local café and Isaac quickly finished his shopping. As he headed there, he was wondering if he was making a giant mistake agreeing to this and not telling Jared that he was Isabella. Isaac was kind of flattered that Jared found him attractive as a man.

Isaac ordered a coffee and situated himself at a table, facing the doorway. Jared arrived a few minutes later, looking eager. He waved before he went to order.

"So, what is considered a strange day?" Jared asked as he sat across from him.

Isaac sighed. "It just started bad and got worse. I found out that I was replaced on an important project at work and that I'm basically being downsized. When I went to confront my boss, he asked me to move out of his apartment."

"You were living with your boss?"

"He's been my lover for five years."

"Ohhh," Jared appeared sympathetic.

"Now I'm back in an apartment I don't like, alone, and losing my job. I know it's not the worst thing ever, but my job and my lover are…were my whole life."

Jared took his hand over the table. "It sounds tough. And a lot to take at once."

"Thank you. You're very kind."

"Very kind?" Jared leaned closer. "That's all? Not amazingly attractive and attentive?" His voice had a teasing quality and a smile was tugging at his lips.

"You're so modest," Isaac grinned. "So, what about you?"

"What about me?"

"How was your day?"

"Well, I actually got promoted at work," Jared answered what Isaac figured he'd answer.

"What do you do?"

"I'm a personal assistant. Have you heard of Sassy makeup?"

Isaac nodded.

"I was just promoted to being the personal assistant to the spokeswoman…man…person." Jared fumbled over how to describe Isabella.

Isaac played dumb. "Who?"

"Well, he's a cross dresser, named Isabella."

"Do you like him?" Isaac asked, curious to hear what Jared would say about him.

"I don't know him that well yet, but he's really polite. He's thanked me for things that other people I've worked with have just expected me to do. I like that he doesn't treat me like garbage, well, at least he hasn't yet. It doesn't hurt that he's absolutely beautiful. I have eye candy at work everyday now."

"You think he's beautiful? Don't you prefer men?"

Jared laughed. "I pretty much prefer anyone I'm drawn to. I do like men, but I've been with women too."

"Oh. So you're drawn to me?"

"Are you flirting with me, gorgeous?" Jared joked.

"I'm not sure. I think I am," Isaac answered honestly.

He enjoyed Jared's company. While he loved David and hoped to re-connect with him, Jared was very relaxing to be around. He had this laid back aura and was so reassuring. He wanted to get to know him better.

Jared was running a finger gently along Isaac's knuckle, grinning so wide, Isaac was amazed he could still see Jared's cheeks.

"Are you free for dinner?" Jared asked.

"When were you thinking?"

"Tomorrow night?"

Isaac found himself agreeing, and had this sinking feeling that he was about to go in over his head.


Ummmm…yeah, I'm not really sure where this is going. It started as just an idea for a plot and I feel like the characters need to form a little more. I don't quite have the feeling for them. Hope you enjoy! Thanks!