Yes. You strip down to your underwear.

You listened as Chelsea's footsteps thumped up the stairs to her bedroom. Reaching down to your belt you feel a sudden rush of embarrassment, your cheeks flush and you suddenly realize that your nipples are hard, making it so you feel every brush of your shirts fabric. was the thought of stripping down making you aroused as well as embarrassed? It wasn't something you had ever experienced or even thought about before. But you needed to get this over with, if you wait until Chelsea returns it will only be worse. Instead of your belt you decide to start with your socks, taking them off and placing them on the floor near the couch, you figure that's as good a place as any for a pile of discarded clothing. Your bare feet actually feel pretty good on her wooden floor, which was surprisingly warm, she must have radiant floor heating you think. Stalling and thinking about the floor is not helping, and you hear Chelsea walking around upstairs, probably about to return at any moment. The phone in your pocket vibrates.

"I need proof that you followed instructions. send me a selfie and I better not see any clothes on you but your little undies"

That was pretty much all the motivation you needed, the thought of Gale messaging Chelsea flooding into your mind. Without any more hesitation you undo your belt and pants, letting them fall to the floor. You step out of your jeans and put them with your socks, finally pulling your t-shirt up over your head and discarding it as well. You look down at your small pile of clothing and all the initial shame and embarrassment come back, but you can't let Chelsea know that's how you feel, you need to pretend that you are an eager nudist. Grabbing your phone you take a quick selfie from a high angle, making sure to get your full body in the shot. Yeah, your nipples were definitely hard and the semi-erection pressing against your black cotton boxers was noticeable. In fact, your boxers were soft enough that if you get any harder the outline of your dick will be surprisingly detailed. You send the picture to Gale, sighing at the fact that you are supplying her with more ammo to get you in trouble. The reply comes fast.

"Ooooh look at that! If I didn't know better I might think that you like having your clothes taken away. Shame I let you keep your boxers. Well have fun spending the night letting your little friend look you over nearly naked. But not too much fun because I will be checking in on you nudist boy"

Just as you finish reading the text Chelsea walks back in to the living room. She is carrying a red N64 controller in one hand and a large glass bong in the other. She stops as she enters, looking you up and down. You notice her gaze lingers on the only part of you that is still clothed. The silence lingers for a moment and you worry that she might actually not be okay with this, but then she breaks the silence by saying...

"My nipples look like milk duds!" She lets out a laugh at her own reference while walking over and placing the bong on the coffee table. Chelsea looks at your confused expression. "What? You haven't seen Kung-Pow Enter the Fist? Fucking stupid movie... its great."

"N-no I haven't... uhh nice controller" you say, trying to change the subject.

"Oh, well we should watch it later its totally your humor. There's a guy in it who says that, sorry I couldn't help myself." She walks over to the tv stand, bending down and turning on a small PC that's plugged in to the television. You cant help but look at her ass as she bends down, you had never noticed how great it looked, especially in tight jeans. "You up for Mario Party 2? that's the best one... and yeah I'm emulating it cause fuck Nintendo's bullshit."

"Oh! hey you know Im always down to win at Mario Party" You say, suddenly not so embarrassed. Chelsea seemed to be totally fine with you in just your underwear, even if it was a little revealing. Her joke, even at the expense of you and your hard nipples, was heling to put you at ease.

"pfffff yeah right man, how many times have you won in the past 10 games we played? Like 3? And those were the switch Mario Party games which are way easier. Mario Party 2 is for real men... and ladies" she said, looking at you coyly and fluttering her eyelashes to emphasize the word ladies.

"uh huh, I'm sure when this game came out in the 90's you were a real hardcore gamer." You say rolling your eyes. For a moment you forget your state of undress, but as you shift your bare feet you feel the soft cotton of your boxers rub the head of your cock, realizing that at any time Chelsea could look at your crotch and see the partial arousal. In fact, you realize she had to have noticed it when she entered the room and got a good look at you. The blush comes back to your cheeks.

"Hey we burned holes in our palms for this shit back in the day. Who knew a Mario game would give kids a stigmata on the playground." Chelsea turns to you and tosses you a second controller. For a second you think her eyes may have flicked downwards to your private regions.... "But if you're so sure of yourself why don't we make this a little more interesting?"

"How so?" you ask. Apparently Chelsea was feeling a little extra competitive tonight.

"Hmmmm... Welllll maybe I was going to suggest that the loser of each game takes off a piece of clothing. But I mean I would have a huge advantage and its not like it would be much of a punishment for you since you are a nudist and all..." Chelsea smiles. Her calling you a nudist made you blush even harder. It looks like your best friend really thinks you enjoy going around with no clothes, but You suppose you can't blame her, as you are sitting in her apartment with barely anything on.

"How about this..." she says. "when someone gets a star the other person takes a bong hit." she leaned forward on the couch and tapped the glass bong on the table for emphasis. You notice that the bowl is already packed and its a pretty big one. You enjoyed smoking a bit after a long work day, but more than one or two bong hits would get you fried. "and to make it more interesting, if you lose a minigame you gotta take a drink. Can't let that six pack go to waste!"

"Alright then, you're on but I hope you are ready to get toasted in more ways than one." You say, sparking up some fake confidence, both in your ability to play the game while nearly nude, and in your ability to be nearly nude around your tomboy best friend. Suddenly you realize that in your nervousness you left the 6 pack of beer in your car. "Oh shit, let me go grab the beers from my car, cant just bum your drinks all night." You reach for your pants on the floor before Chelsea interrupts you.

"Just go grab it real quick like that, It took you long enough to work up the courage to be yourself... and I want to get this night started!" She laughed but you couldn't believe that was a serious suggestion.

"Go outside to my car in my boxers? What if someone sees?" The thoughts of her neighbors seeing you running around so skimpily dressed bored into your mind. Thinking about it made your cock twitch and stiffen a bit. Shit if Chelsea looked now she would definitely be able to tell something was up.

"Why not? Your bits are covered and this is private property. If anyone says anything I'll tell them to fuck off." She said with a wink and a smile.