Let her give you a makeover

"Fine." You say defeated. "Let's just get through this round." Olivia jumps up excitedly.

"Excellent!" She says as she begins riffling though her makeup bag. "And stop being so grumpy. This is fun!"

"Easy for you to say. You haven't had to do anything embarrassing." You say as you watch her carefully selecting things from the bag.

"Oh, stop being a sore loser." She says as she removes a few items from the bag and moves back towards you. "And you never have to be embarrassed around me." She smiles before sitting down in front of you. She takes out a brush and begins swiping it against your cheek. "I luckily have a shade perfect for your complexion."

You wait patiently as she gets to work. She brushes and rubs and marks all over your face. You have no idea how she can do this to herself every morning as it feels like it's going on forever. She eventually puts her brushes down and picks up a small box containing false eyelashes.

"Isn't that a little much?" You say. Slightly concerned by how involved this is getting.

"Go big or go home." She says cheerfully as she carefully pastes them onto you eyelids. Once done, she takes a step back, admiring her work. "You're beautiful!" She says. "Just a few more things." She says as she gets up and goes to the closet.

You're not sure if you believe you don't look completely ridiculous right now, but at least she's almost done.

She soon comes back, this time with what appears to be a shoulder length blonde wig. You can see her holding something in her other hand, but can't tell what it is.

"A wig?" You ask, discouraged. "I thought you were just doing makeup."

"Everyone knows that hair and makeup go together." She says as she tosses it onto your head. She makes some adjustments before moving her hands down towards your chest. She pulls on the bra and slips something inside.

"What's that?" You ask as you feel something cool and soft stick onto your chest.

"Breast forms." She says as she moves the bra back in place. "They'll help the bra fit better."

She takes a step back, looking at you. Her face looks almost surprised as she stares at you.

"Are we done?" You ask. Having breasts has pushed you over the edge patience wise.

"Just one last thing!" She says before holding up a bottle of shaving cream and a plastic razor.

"No way!" You shout in response. "I don't need to shave my legs."

"Look, I'm not saying the natural look can't be sexy, but now your hair colors don't match." She says.

It's now that you start to wonder if this is all worth it. This was supposed to just be a game after all. However, winning would allow you to have one of the best nights of your life. You once again swallow your pride and hold out your leg. She immediately gets to work removing all of the hair from your legs. Once again, you zone out as time passes by slowly. Luckily this seems a bit quicker as before you know it she's wiping your legs clean with a towel. You look down to see them, now shiny and hairless.

"Perfect!" Olivia shouts. As she once again admires her work. "You're almost hotter than me now."

"What do you want me to do for the picture." You ask, a bit annoyed that your turn has gone on for this long.

"Get on the bed." She says as she picks the camera back up.

You do as you're told and lay down on your bed. Thoughts of underwear models begin popping in your head as you lean on your side, your head propped up looking forward.

"My god! You're a natural!" Olivia says as you hear the camera click. "I didn't even have to tell you how to pose."

You feel your face getting warm, embarrassed by her reaction, but also a little excited as well.

"Okay, that was a good formal one, now lets get a little dirtier." She says "Lay on your back." You do as instructed. Oliva comes closer holding the camera above you. "Now slide your hand into your underwear, like your pleasuring yourself." This excites you. You slide your hand in. Your cock is still soft but you can feel it twitch a bit from your touch. "Don't actually do it though." She says. "If your dicks hard it'll show up in the pictures." You immediately move you hand to the side, simply grazing it. "Now, your other hand on your breast." She commands. You do as told, grabbing your left cup softly. "Good. Now look at the camera like you want to be fucked." This throws you off a bit. You've never heard Olivia talk like that, but also you don't know how to make that look. You do your best, thinking back to all the porn you've seen, women getting railed while gasping from pleasure. You part your lips and roll your eyes back.

"PERFECT!" Olivia shouts as she snaps another picture.

She quickly turns the camera to you, so you can see the image. You're shocked. You can't even tell that's you. The worst part is, it's hot! As if a screenshot from a porn video.

"That's a keeper!" She says as she begins to move the camera away. Your eyes follow, attempting to get one more look at that sexy woman. "Looks like you really like it." Olivia says, as her attention turns towards your crotch. You look down to see your cock pushing the underwear up as it hardens.

"Well. I guess that photo shoots over." Olivia says. putting the camera away.

"That still counts though, right?" You ask, there's no way did all that for nothing.

"Fine fine." She says "Since that las one was so hot, I'll let it count. But you have to let me take 3 more pictures of you before the night is over."

"Deal!" You say as you get up to move your piece. Thrilled that your turn is finally over.

Olivia takes the dice and rolls a 6.

"I honestly thought you'd back out of that one, I guess this game's going to be closer than I thought." She says as she picks a card.