The Administrative Assistant Job

This was humiliating, or at least Aaron thought it would be. Doing administrative work as a woman? It was insane, but it’s what he had to do. Sarah’s laughter at his predicament didn’t help either.

“What are you laughing at?” Aaron scowled through his painted-on face, “You did this!”

“Hey, lighten up!”, Sarah looked remorseful yet happy, “being a girl isn’t that bad, and this is good money regardless! Maybe you’ll even want to stay a woman!”

“Shut up.” Aaron mumbled, his face turning a bright shade of crimson.

The silence was broken by a DING; a text.

“They need me to fill out employment paperwork.”, Aaron took a deep breath, dreading the next day.

Sarah ran into his room in the morning, blinding Aaron with the lights as she flicked them on.

“Wake up, mom!”, she laughed.

“W..what time is it?”, Aaron looked at the green glow of his digital clock.

6 am.

“But I need to go in at 10.” He let out, groggily.

“Not looking like that you won’t! Get out of bed.” She pulled her father out of bed and handed him a couple bottles, “Go take a shower and use these.”

“Fine.” Aaron stumbled over to the shower and turned it on. The ache in his foot was still pronounced, so he hopped under the water and without really looking, began to slather the liquid from the bottle all over him. It was fruity in smell, and as he spread it all over, he felt his skin, realizing that it was doing a lot of work in softening it.

He spent a lot of time in the shower, letting the warm water wash over him, almost dozing off a few times. Finally starting to wake up, he got out of the shower and grabbed a towel, wrapping it around his body just like Sarah had shown him. Looking in the mirror, he was surprised at how much he looked like a woman, even with the makeup washed away. His hair was still that ridiculous shade and style, and the corset must’ve had some residual effects because he looked thinner. The breast forms sure didn’t help.

Drying himself off, he went out to find Sarah all ready, stacks of clothes lined up on the bed.

“Ok, mom! Let’s get you ready.” Sarah smiled, tapping on the bed as a gesture for her father, now mother, to sit down.

“What now?” Aaron asked, a bit of concern tinging his voice.

“Don’t worry, we won’t be dressing you in an outfit as revealing as yesterday. Here, put these on first.” She tossed him a pair of flesh colored panties and looked away.

Aaron knew what to do, and began to pull the panties up his legs, resting them on his hips. They were really tight, and he could feel his man business being crushed down with them. Sarah turned around and tossed him a second pair of panties, this time pink.

“Wait, what are these for?” He asked, gesturing at the panties currently sitting on his crotch.

“Oh, that first pair was just to keep everything bundled. The second pair is your real pair.” She explained.

Aaron nodded, pulling the panties up and with that, Sarah tossed him a matching pink bra. He fit it over his breasts and tried to clasp it, but just couldn’t get the right angle. Sarah started giggling and made her way behind him, clasping the bra in place.

“I got something simple. An old pair of my jeans and a blouse. Shouldn’t be too revealing and looks feminine enough for you to easily pass.” She explained.

“Ok, thanks” Aaron looked incredibly embarrassed, but grabbed the jeans and pulled them up his legs. They were tight, and he had a hard time getting them on there, but he was able to get them in place and zip up the fly. It really accentuated his ass, which was odd to him. Sarah pulled out the corset from the day before and clipped it onto him, getting Aaron to take a deep breath before she pulled the strings in. Looser this time, but still pretty tight.

The blouse was pretty easy, going on as a buttoned-up shirts and flaring out a little bit. It was conservative, buttoned all the way up to his neck, so he felt good about that. He wouldn’t attract many eyes with this look, and that was good.

“Time to put your face on, mom” Sarah joked, pulling her father back into the bathroom, where she had placed a few containers. Mascara, foundation, concealer, blush, eyeliner; the works.

With each step, Sarah explained what she was doing in a lot of detail. Oddly enough, Aaron found a lot of it very interesting, and particularly liked how passionate Sarah was about the kind of stuff he never even thought about. With a nice, neutral foundation on, she contoured his face with concealer and painted his lips with a darker pastel pale color. She did one of his eyes with light eyeliner and mascara and even handed her father the brush, allowing him to finish the second eye. He was even smiling a bit. For some reason, this time he was spending with his daughter made him forget the humiliation of his circumstance, if only for a moment.

They finished up, and Aaron was now Erin, at least in looks. Sarah gave him a pair of sensible black flats, which he slipped on. They were comfortable.

“Ok, off to work.” Aaron smiled, nervously exhaling.

“Not yet! Here!” Sarah tossed him a purse, which he looked through, finding Erin’s ID and a tube of lipstick, chapstick, a couple spare breath mints, and his phone. Sarah must’ve been busy last night, because she replaced his phone case with hers. White and purple, it was definitely a girl’s phone, but when Aaron opened it up, it was still his.

“Thanks.” Aaron walked out the door, and off to his new job.

When he got there, they immediately brought him in to fill out some new hire paperwork. The forms were pretty simple, and having remembered his wife’s social security number, everything was in order. He went to sign the bottom of the last page:

Aar- shit.

He scribbled the mistake out and wrote in ERIN.

It felt weird signing his dead wife’s name, but he didn’t really think too much into it. The hospital was pretty busy, and when Aaron was done, the HR people gave him the room number. He walked over, trying not to make eye contact with anyone. It was pretty embarrassing, after all. That would come back to bite him when a doctor, running down the hall, collided with him, sending him to the ground. When Aaron got up, he looked down in horror to see that the top buttons on his blouse had come loose, hanging down at best, and on the floor at worst. The blouse now furled open, showing a lot of cleavage and little peaks of his bra.

His face turned red, and unable to get a word to leave his mouth, he just ran on until he made it to Brad’s office. He was greeted by Brad himself, who brought him inside and sat him down at the receptionist’s desk. Brad explained that all he needed to do was answer calls and get everything sorted. While he explained, Aaron felt Brad’s eyes drifting downward, looking at his cleavage. It made Aaron feel really uncomfortable, but Brad was with a patient soon after, so it wasn’t a big deal. Before he left, however, Brad added one more thing.

“Oh, and Erin. We have a dress code. This is ok because it’s your first day, but we expect a skirt, blouse, pantyhose and heels. I’ll make an exception on the heels until your sprain is healed, but no pants here.” He smiled before leaving.

The day was pretty noneventful, all things considered. Aaron kept getting texts from Ted, which he responded to quickly, trying to help Ted understand that he wasn’t interested. Ted clearly didn’t understand, so eventually, Aaron just ignored the texts.

After the day was done, Aaron came home and hit the couch. Almost immediately, Sarah was over him smiling, “So how was your first day at work, mom!”

“It was fine. We have a dress code. I need a skirt, some pantyhose, and a few more blouses.”, Aaron explained, gesturing at his almost exposed breasts.

“Wait, so does that mean?” Sarah began, and Aaron dreaded the next words to come out of her mouth

"SHOPPING SPREE!"