While playing video games with your brother.

You and Your brother Jason are playing Guilty Gear Strive, a fighting game, on his PS5 in his room. Your phone chimes with your second challenge.

"Up the stakes with strip the loser. (Challenge complete once one of you has zero clothes on)"

You look at it in between matches. You take a deep breath then taunt Jason.

"Let's make this more interesting." You say.

"How so, money?"

"Hmm, lets say $10 for each article of clothing still on."

"What do you mean?"

"Loser of a round takes off a piece of clothes. Loser at the end pays the winner for each piece of clothes they still have on."

"Jen, I don't know, that's kind of-"

"Sounds like you are chicken, or have a tiny cock."

"Fuck it, you're on."

You glance at what he is wearing, shorts, presumably boxers underneath, and a t-shirt. You are wearing panties, shorts, and a sleeveless shirt. It seems even to you. You pick your main and he changes characters. You silently question it until he starts kicking your ass, he wins the first round.

"Dammit, what was that about?" You ask

"Well, playing for stakes I figured I should play my true main." He says with a sly smile.

You pout but slide your shorts off. You sit back down next to him and play another round. You lose again, but it was close.

"I'm learning your patterns, you wont be so lucky next round." You say.

You turn sideways and slide your panties off.

"Panties before shirt, interesting choice." He says.

"Yeah well, you can't see my pussy while I'm sitting, my tits are a different story." You say.

"Works for me, less distraction." He says.

You wince at the realization that distracting him might have been better. You steel yourself for the next round and win. He removes his shorts, revealing his boxers underneath. You win the next round as well and he removes his boxers.

"I was right, cock looks kinda small." You say teasingly.

"It's just not hard. It grows." He says.

"Yeah, right."

"Have you never?..."

"This would be the first I have seen in person." You say.

"Well some cocks grow when they get touched."

"Show me."

"What?"

"I want to see if what you say is true, It's something I need to know for the future."

"I guess... It would probably grow quicker if you touch it though."

"You are just lazy."

You reach out and start poking his dick. You play with it in your hand for a few minutes when his cock starts to harden. You keep playing with it and soon it grows to it's full size.

"Well I guess you weren't lying. That's so cool. How do you get it to shrink back?" You ask

"By cumming."

"Uh, I won't be helping you with that."

"Aren't you curious what that's like?"

"Yes, but... Let's finish the game."

You sit back down next to him and play, but you can't keep your eyes off his cock and you lose. You sigh and take off your top, your breasts bouncing into the open. Your phone chimes with completion, you can get dressed anytime now, but.

"Nice." Jason says, eyeing your chest. "Hey, I will drop what you owe me for losing if you watch me cum. What do you say?"

"Sounds too easy." You say.

"Okay, stay naked and sit on the floor in front of me. okay, now lean back. Just like that, now don't move."

He starts stroking his hard cock in front of you. You sit on the floor in front of him, your legs spread with your knees up, your hands on the floor behind you.

"You watching? I'm about to cum." He says.

You watch as his cock starts to pulse and then it shoots out a stream of white cum straight at you hitting your mouth and chin.

"Uh, dude you didn't say it would-"

The second stream goes into your open mouth as you talked. You taste it on your tongue as you watch the next weaker stream land on your chest. You watch as every bit of cum shoots from his cock. Then it slows to just dribbling out of his cock and landing on your exposed pussy. You stay still until he is finished cumming.

"What did you think?" He asks.

You lick your lips and say "A lot more forceful than I expected."

"Yeah, Hey you want to keep playing? We can up the stakes even." He says

You look at your phone, no current challenges...