Bard, Rogue & Sorcerer: Stealth and trickery

ROGUE, whispering: ”Alright, here's the plan. I'll need a distraction from both of you. Bard, how about you pretend to trip and bump into her arms as she walks by, and maybe strike up a conversation while you’re at it, but whatever you do try to divert her attention with your touch. Sorcerer, once I got the clasp undone join in by politely pushing your way past the two of them on your way across the room. The more touch the better; that way she’s less likely to notice me rummaging around behind her back.”

BARD, with a playful grin: ”I've got this. Watch and learn.” I go over to the barmaid, trip into her arms and start distracting her.

DM: Roll a Deception check for me please.

BARD: >diceclatter< Easy as pie, a 27!

DM: I don’t know why I even ask anymore, with those absurd modifiers. Well, anyway, you put on a convincing little show, pretending to trip and stumble just as the barmaid is walking past. She instinctively reaches out and catches you, and you strike up a friendly conversation, all the while retaining contact with the barmaid’s hands or forearms. She is a little startled by the incident: ”Oh, are you alright?”

BARD, chuckling lightheartedly: ”Yes, yes, just a little clumsy, my dear. Apologies!”

ROGUE: While her attention is on the bard I’ll come up behind her and start trying to undo her bra as sneakily as I can.

DM: Make a Sleight of hand check please.

ROGUE: >Diceroll< Natural 20!!

There was a round of woohoo’s and cheers around the table.

DM: Stunning! The rogue positions herself strategically, waiting for the opportune moment. The bard plays her part impeccably, deftly redirecting the barmaid's attention to her. Upon identifying at what height the clasp of her bra is located, timed to coincide with the moment the bard’s fingers brush against the skin of the barmaid’s hands and forearms, the rogue strikes with an inhuman finesse. With but a fleeting touch - barely noticeable amidst the barmaid’s friendly interaction with the bard - the bra is unhooked through the fabric of the blouse, using little more than a deft twist of the hand so light an onlooker would have trouble registering there had even been any physical contact at all. From the front the bard can see how the barmaid's cleavage sags slightly though, as its support is loosened.

SORCERER: I make my way through the crowd while they’re chatting, and put on my best apologetic smile as I gently press past them and accidentally bump into her, ensuring that my touch lingers just long enough to keep her focused on the two of us while the rogue does her thing.

DM: Roll a Deception check for me, please.

SORCERER: >Diceclatter< Deception is a... 21, long live my high Charisma score.

DM: You guys are on a roll today! Based on that roll, and the rogue’s natural 20 just now, you smoothly navigate through the crowd, deftly brushing against the barmaid as you squeeze past her in the narrow pathways between the tables, nudging her a step aside for a moment. She was already too focussed on her chat with the bard to think much of it. The rogue manages to gracefully move a hand underneath the barmaid’s loose blouse and, dancing in tune with the rhythm of the various distractions, skillfully slips out a lovely crimson bra. Amidst the hearty bustle of the tavern and with all the barmaid’s attention and senses firmly directed forwards due to the bard and sorcerer’s expertly timed stumbles, touches and nudges, the barmaid remains blissfully unaware of the extraction operation that just took place beneath her top. As the rogue slyly tucks the stolen underwear away, the barmaid continues her conversation, none the wiser that she's now missing one key undergarment, though the bard catches… let’s just say a hint of the natural firmness of the barmaid’s bosom.

BARD: Alright, I wrap up the conversation and we reconvene at the table.

ROGUE: That’s the hard part done - you’re welcome - and now there’s just one piece left to go.