You'll be wearing a vibrating cock ring

You drop Kim's order off to the bartender, a redhead who looked like she was about Your age.
She told you to return in a few minutes to pick up the drink.
In the mean time You left for Sarah's office to ask about what to do next.

You knocked lightly on the door and called out "Sarah?"
The door creaked open and the young businesswoman glanced up from her work for a moment, then returned to her keyboard.

"Hey, come on in," she said without lifting her eyes from the screen. "Have you finished that order with your teacher?"

"No, not yet," You replied. "She wanted the birthday suit special, with a ring on it. I don't have a clue what that means."

Sarah let out a whistle. "Damn, she's going all out tonight. That'll probably cost her more than her whole tab combined."

"Wait, what is it?" You asked, intrigued by her reaction.

"It's an add-on item we offer our guests. It can be controlled through our app." She pulled open a drawer and retrieved a metallic ring.

"What does it do?"

"It's a vibrating ring that you wear around the base of your shaft," she explained, holding it up for you to see. "There's a QR code on the top of it, so make sure to present your member to her so she can scan it."

You hold the ring, shocked and unable to really process what your boss just told you. A call soon came from the phone on her desk, prompting her to usher you out of her office.

"I need to take this now John," she said as she led you to the door. "Why don't you use the changing room to get undressed. And don't keep that beauty waiting too long. She's paying good money to see you." She said as she moved you out of her office.

Your hands are shaking as you quickly start stripping off your clothes. Shirt, shoes, socks, briefs. You hastily throw them into your locker, barely managing to get the lock closed. The frigid air in the locker room causes your skin to break out in goosebumps and makes you feel unbearably exposed. The reverberating chatter and music from the main hall isn't helping your frayed nerves either.

The faint clinking of the metal ring fills the empty locker room as it fits snugly to the base of your penis. This, along with a flustered look on your face, will be the only things you have to wear for the next few hours.
Taking a deep breath, you try to steady your trembling legs as you move towards the restaurant door, barefoot across the cold tile floor.

The moment you stepped into the room, the girls nearby erupted in a chorus of naughty laughter . Whistles and cheers filled the space, making it painfully obvious that all eyes were on you as you moved forward. And even though you weren't the first guy to walk through the door with your cock out, the ladies seemed particularly enamored with you. You tried to pay them no mind, the only focus for you was Kim's drink.

Returning to the bar, the redhead who had paid you little attention before suddenly seemed to take an avid interest in you. You swore you heard her murmur something about how much she loved her job, but you couldn't be sure over the sound of your pounding heart.

Shifting uncomfortably, you tried to press yourself against the bar to make sure your penis was hidden from sight. "Um.. Hi. Is my whiskey highball ready?" You stammered, averting her gaze.

"What was that, good-looking?" She spoke before the words clicked with her. "Ah, your guest's order. Here it is... umm."
The girl giggled before continuing. "I'm sorry but I totally forgot to read your nametag last time we met. I didn't expect you to be naked the next time around."

"It's John."

"Well, John, I'm excited to work with you," she said, her grin growing wider as she placed the drink on your tray. You picked up your tray and prepared to leave, but then you noticed she was still staring at you, clearly eager to catch another glimpse of you in the buff.

You blush, but pay her no mind. As you move away she shouts "Nice ass, John!", you hear her cackle behind you.
Flustered, you think about turning around to shout something back, but decide against it. knowing that the last thing you need is for her to catch another glimpse of your ring-bound member.

Your steps hurry across the restaurant Kim began to come into view. You pause nervously, suddenly aware that your English teacher is about to witness you wearing nothing but a cock ring.
The perverted irony of the situation is unignorable - all those days you used to discreetly stare at her chest, and now she was going to be graced with a full view of your most intimate assets.

Taking a few deep breaths to steady your nerves, reminding yourself that this is just a job. Even though you know Kim well, you have to stay professional. Serving food and drink in the nude is what you get paid for now, so there's no need to make it any more uncomfortable than it already is.

As you strutted towards Kim her eyes widened and drank in your form. She tracked the swing of your hips and the gleam of the silver ring around your penis, as it swayed hypnotically with each step. Her intense gaze made it twitch with arousal. That was all the encouragement she needed to let out a low whistle as you halted in front of her.

"Your drink, Kim." You mumble, your face burning with embarrassment as you try to maintain composure. You carefully place the whiskey on a napkin before setting the meal menu beside it.

"Excellent presentation John. You made carrying that drink look like a work of art." Kim clapped as she drew her eyes away from your penis long enough to talk to you. "The way you stretched to place that drink, what an view of those pecks in motion. Not to mention that strut of yours when you where balancing that tray. Have you been practicing or are you just a natural at this?"

"Y-yeah, I guess," you stutter. "I'm still not used to being naked in front of people though."

Kim smiles coyly and takes a closer look at your cock ring. "I can tell you're still getting used to it," she teases. "But you seem to enjoy it, don't you?" She reaches out her hand to touch the ring, but you take a step back.

"Sorry John, didn't mean to frighten you. I just have to scan the code." Kim spoke while holding her phone in her hand.

"Oh, right." You remembered the QR code on top of the silver band and obediently presented your penis to Kim.

Kim held the phone between you two, her other hand clasped firmly around the ring. Your shaft brushed against her soft, delicate palm as you both breathed heavily. The blue light radiating from the phone backlit Kim's face as your naked member filled the display. She quickly zoomed in, capturing the code and unlocking a control app for the ring.

"Well then, how about we give this thing a test run?"