Chapter 2: Makeup
Jay
What did I just agree to?
The way Steph smiled at Jay was unnerving. He — no, she now — gave her a nervous smile in return, which only seemed to encourage Steph more.
“So… um…” Jay cleared her throat. “What now?”
Steph shrugged. “Now, you’re my girlfriend. Any more questions?”
“That’s it?”
Steph nodded. “That’s it.”
Jay frowned. “What do you mean? No makeup? No girly clothes?”
“Do you want makeup and girly clothes, Jay?”
“I–” Jay swallowed, her throat suddenly feeling dry. “N-not really, but if I’m a girl–”
“Ok, well, if you don’t want, then that’s fine. Guess my girlfriend’s more of a tomboy, huh?”
Jay groaned. “But shouldn’t I, you know, look the part?”
“Look the part?”
“You know, more… more like a girl.”
“Do you want to look more like a girl, Jay?”
Yes.
“Um-” Jay shrugged, letting out a small huff. “Yes? No? Maybe? I don’t know!”
Steph nodded slowly. “Would you like to find out, Jay?”
Jay froze, then, ever so slightly, nodded her head.
Steph
Steph could tell that Jay wasn’t going to crack that easy. At this point, it was almost certain Jay was an egg. Most cis men wouldn’t have even agreed to Steph’s idea in the first place!
And the look of longing on Jay’s face at the idea of wearing makeup and women’s clothing… it was almost nostalgic for Steph. She remembered being in that exact position, staring wistfully at pretty skirts and dress and whatnot, constantly having to suppress her jealousy at other girls for managing to look so effortlessly pretty. Well, Steph looked effortlessly pretty now — which she could acknowledge most of the time — but, the point is, she had a good idea of what was going through her girlfriend’s head.
Steph took Jay’s shaking hand, and led her into Steph’s bedroom — which had previously been Jay’s roommate’s.
“Alight, Jay,” Steph said. “I am going to put makeup on you unless you tell me no. I am going to pick out an outfit for you to wear unless you tell me no. I will even paint your nails unless you tell me no. Is that ok?”
Hesitation, and then — Jay nodded, staring at the ground, her cheeks flushed.
“Great! We’re close enough in skin tone, so I can use some of my unopened stuff for you. We’re around the same height, so my clothes should fit just fine. What nail colour would you prefer?”
“Um- I don’t know. You pick?” Jay looked anxious, but she had stopped fidgeting, and was now sitting on the edge of Steph’s bed.
“Ok,” Steph said.
“You won’t tell me which one?”
“Haven’t decided yet.”
“Oh. That makes sense.”
“Nervous?”
Jay nodded. “Very.”
“Hey, hey,” Steph said, soothingly, running a hand through her girlfriend’s soft hair. “So was I my first time. It’ll be fine. I’ll make you look really pretty. Trust me.”
Jay’s eyes went wide. “P-pretty?”
Steph smiled warmly. “Very pretty.”
She dug through her makeup supplies, finding an unopened tube of concealer, eyeliner, lipstick, eye shadow, and soma mascara.
“You just sit still, cutie. This won’t take long.” Steph started with the concealer, covering Jay’s faint beard shadow until it was no longer visible. Afterwards, she applied the eye shadow and liner, followed by the mascara. It took a few tries before she could get Jay to sit still.
“It’s just scary, having something that close to my eye!”
“I know,” Steph replied. “You get used to it.”
Finally, Steph applied the lipstick to Jay’s lips, then took a step back to admire her handiwork. Admittedly, Jay didn’t look much different, but she did look really pretty.
“Wanna see?” Steph asked.
Jay nodded, and Steph took her hand, leading her towards the floor length mirror on the closet door.
Jay
She’s pretty.
She’s me.
I’m pretty.
Jay stood, transfixed by the cute girl she saw in the mirror. Her makeup was light, the eyeliner serving to draw attention to her cute blue eyes. The lipstick wasn’t that far off her natural lip colour, but it somehow made them look… kissable.
Jay had to admit - she made a very pretty girl.
There was just one problem.
“Hmmm, definitely need a change of clothes,” Steph said. “Let’s see…”
Steph started poking around in her closet, hunting for some clothes. She grabbed a floral print skirt, laying it on her bed. Jay started getting a little anxious. That was so girly…
But then again, so was Jay, with that makeup. She didn’t even know concealer could so effectively hide her facial hair like that. It was… It felt really nice.
Steph eventually assembled a full outfit: the floral print skirt, a pair of plain black leggings, and a black v-neck t-shirt.
Jay stared at the clothing with apprehension. “Aren’t those your clothes?”
Steph nodded. “It’s ok, you can wear them. I want you to wear them, Jay.”
Jay swallowed. She picked up the shirt, since it felt like the safest one to start with.
“I can give you some privacy.” Steph left the room, closing the door behind her, leaving Jay alone. Jay stripped off her hoodie and the ratty old t-shirt she had on underneath, quickly replacing them with the v-neck t-shirt. It was soft — softer than her old clothes. It hugged her torso, although it felt a little baggy in the chest area — which made sense, Steph was a bit more well-endowed than Jay was, on account of actually having been on estrogen.
Then came the bottoms. Jay undid her jeans, slipping them off and leaving them in a heap on the floor. She grabbed the leggings and, before she could chicken out, pulled them on. The fit really snug, which felt amazing, except for one small problem - the hairs on her legs. She pulled the leggings back off, then popped her head out of the bedroom, quickly finding Steph.
“Hey!” Jay called.
Steph looked up from her phone. “What’s up?”
“I uh… hair. On my legs. Help. Please.”
Steph blinked. Then she giggled. “Oh, right. Forgot about that. You want to shave that?”
Jay nodded.
“Ok. You can borrow my razor.”
Jay stepped out of the bedroom, forgetting about her lack of pants. Steph didn’t comment on it, instead taking Jay’s hand and leading her into the bathroom.
Steph held up her razor, handle pointed towards Jay for her to take. “So,” she said. “First things first: you’re going to want to use some of this.” Steph held up a bottle of shaving cream. “Helps make sure the razor doesn’t irritate your skin. You’ll also want to shave against the direction your hair grows. It allows you to get a closer shave that way. And finally, you should moisturize afterwards. Make sense?”
Jay nodded.
“Alright then! I’ll leave you to it. Call me when you’re done.” Steph started to leave, but stopped. “Oh, also, you’ll probably notice that different patches of hair grows in different directions, so you’ll want to pay attention to that.”
Jay had shaved her legs. And then her arms. And chest. Afterwards, she rubbed moisturizer all over her body. And then continued brushing her hands over the smooth skin left behind.
This is incredible.
Jay resolved to continue shaving her body regularly, even if she did go back to being a boy. It just felt too good not to.
She left the bathroom, standing proudly in front of Steph.
Steph looked Jay up and down. “Looking good, cutie.”
Jay blushed. “Th-thanks.”
Steph grabbed Jay’s hand. “Now, come on. Clothes are waiting.” She lead Jay back to her bedroom.
Jay eagerly slid the leggings back onto her legs, appreciating just how good they felt against her much smoother skin.
And then, finally, she picked up the skirt. She turned to Steph, hoping Steph could pick up on how nervous she was feeling.
Steph gave her an encouraging smile. “Go on, cutie.”
Jay liked being called a cutie.
She put on the skirt, then turned to face Steph, a nervous smile on her face.
Steph smiled back. “Not quite, cutie. Here, let me help.” Steph pulled Jay towards her, then adjusted Jay’s skirt so it sat a bit higher on her waist. “There we go.” She gave Jay a quick kiss on the cheek. “Have a look.” She gestured to the mirror.
Jay stepped in front of the mirror, her eyes shut, anxious she’d looked ridiculous.
Then she opened her eyes.
Oh.