5 points, 1 point outfit.

You think for a bit before stumbling on a dress you were given as a gift once. It covers everything.

It's a strapless dress that thanks to your bust size has plenty to hold it up. The bottom of the dress is split on both sides. You put it on and look in the mirror. The split sides come up to your belly button in height so a good view from the side might reveal your lack of underwear. The dress goes down to your knees which should be good. The only problem is the dress is see through in the right light. You scan your outfit into the app and go to your dad. He gives you a look and says.

"Should I have dressed up too?" with a slight chuckle.

"Come on let's go, I'm starved." You say.

"Just a moment, we are waiting on Dave."

You sigh and wait. The doorbell rings 5 minutes later and your dad yells from the kitchen for you to answer the door. Dave is your dad's friend but ever since you turned 21 he has been looking at you with lust in his eyes so you always try to remain extra clothed around him but you already started the challenge and canceling too many times can end up in a lifetime ban. You open the door and you get hit with the setting sun pointing all it's light right at you. After your eyes adjust You see Dave and he definitely sees you.

"What is it? Do I have something-" You say as you look down where he is looking "-on... me... Dave my eyes are up here."

When you looked down you could see your entire body illuminated under the dress by the direct sunlight. Your face burns red as you get more and more embarrassed.

"Your eyes may be, but... damn Jen, you looking good in that dress." He says.

He never looks above your breasts until your dad rounds the corner.

"Everyone ready?" He asks as he squeezes past you. You follow him and Dave follows you. Not much happens on the way there and you hurry inside the restaurant. You three get seated and your dad and Dave talk for a while. Then your dad excuses himself to the bathroom. It's just you and Dave.

"You have become a beautiful woman Jen." He says.

"Thank you" You say dismissively.

"Man, what I would do to you if I could."

"...and what might that be?"

He scoots closer to you and places a hand on your bare thigh, your dress sits between your legs. He leans close to your ear.

"I would massage you all over. Every inch of your body would experience my touch. For hours I would continue, never once touching your pussy or your nipples. You would quickly crave it but I would deny you until you begged and begged. Then I would slide my hard cock between your legs slowly and deliberately down into your waiting pussy. My cock would kiss your cervix before slowly sliding back out. Then back in just as slow. You would try to grind yourself onto me but I would hold you in place. Then I-" He says, answering your rhetorical question.

"Please stop." You whisper.

"Hmm? Why? Getting aroused already?"

"N-no."

"Prove it and I will leave you alone."

"How so?"

He grabs the front of your dress and moves it from covering your pussy to over your other leg.

"If you aren't wet in there, I will stop." He says.

You spread your legs knowing you can't be wet from his silly speech. He however doesn't go for your pussy. He gropes your thighs softly. He climbs his hand higher and higher until right before your pussy and the pulls his hand back down your leg. Your dad returns while Dave's hand is almost at your pussy and without thinking you close your legs and cover your crotch back up with your dress. However, Dave's hand got pushed against your pussy and is locked there by your legs. You let out a quiet moan at the sudden touch he made you crave. You spread you legs again to let him pull his hand away but he first, very slowly slides a finger into you. He slowly slides his middle finger along the top of your vagina. You bite your bottom lip and hope your Dad won't notice. Thankfully the waiter is bringing out your table's food now and your Dad is distracted. Dave's finger reaches your cervix and he curls his finger slightly. You grab onto the table and his leg as your body starts cumming. You try to hide your orgasm as the waiter places everyone's food down. You notice the waiter pause as he places yours down, but he remains professional. Your Dad is too engrossed with his steak to look up at you.

Dave removes his finger from you when your Dad does eventually look up. Dave looks at you and says:

"Thanks for. cumming. Jennifer." with a smirk.

"Yeah, thank for coming, dear." Your Dad adds.

Your face flushes red.

"N-no p-problem." You say shyly.

You all eat your dinner and afterwards the sun has already gone down. Your Dad drives Dave home since he walked to your house. He gets out of the car.

"Hey John, can I borrow Jen for a bit? I want to show her something that I was telling her about at dinner." Dave asks.

"Yeah sure, I will wait right here. Don't take too long." Your Dad says.

Dave opens your car door and you step out and follow him to his back yard.

"What is it you want to show me?" You ask.

"I made you cum. Only right that you return the favor." He says whiling tugging his pants down.

"I didn't want you to do that, and this is gonna take too long, my Dad will get suspicious."

"Not if you hurry up."

You glare at him for a moment then scan his yard for something to rest on. You see some cushions and grab one. You toss it at his feet and kneel down.

"You could have just bent over. Would have been a lot quicker." He says.

"I hab mo impention po-" You try to say with his cock already in your mouth.

"Don't talk with your mouth full."

You roll your eyes and just go back to sucking his cock. You bob your head along his shaft while making a mental note of just how large his cock is. You suck for a while and then you hear your dad calling for you.

"Come on Jen, we gotta go." He calls from his car still.

"Sounds like your dad is telling me what to do." Dave chuckles.

It takes you a moment to get it but when you do you pull back to say.

"Do not cum on me."

You return to sucking his cock. After another few minutes you hear your dad getting closer while calling you.

"Are you almost there?" You ask after pulling your mouth off his cock again.

"Not close enough. Let me see your body real quick."

"What?"

"Just do it."

You curl up your dress to above your chest. He takes a picture of you and goes inside while telling you to stall. You lower your dress just in time as your dad appears around the corner. You stall while saying Dave is getting something for you. After a couple minutes he returns with a glass. He hands it to you. It's full with white translucent liquid. You look in shock.

"Is this all just...?" You ask

"Yup, just my special drink I was telling you about, no dilution." He says smirking. "Drink up, tell me what you think."

Your Dad just looks at you trying to hurry you up to drink it. You put it to your lips and let it flow into your mouth. You swallow as you continue to pour it into your mouth. Over and over, gulp after gulp. You feel some slip out of your mouth and down onto your dress. After a solid 60 seconds of swallowing his cum, you gasp and hand back the empty cup.

"T-that was so much." You say with some of his cum still lingering in your mouth. "Do you always make so much?"

"Sometimes more, but that is my normal amount." He says.

Your Dad starts heading to the car and calls back for you to hurry along. You look down and place your hands on your belly and accidentally think aloud.

"What if he came that much in my pussy? I would be pregnant for sure."

You look up and he says.

"Maybe someday we can figure that out."

You run after your dad and he drives home. You earned $5000 and think to yourself that it was worth it.