A/N: The idea for this story comes from my best friend! Without her this never would have come to pass.
"Oh Willy," the toothless old woman whistled out, "There's no reason to be afraid," holding the cigarette between her lips she took her hand and ran it through his hair, "I'll take good care of you I promise."
It took everything Willy Wonka had not to run screaming from the room.
"Oh, okay," he stuttered uncomfortably while chewing the inside of his cheek to calm his nerves.
"You said that you've never done this before?" the wrinkly old woman asked, taking the cigarette from her mouth and dropping on the floor of the dirty motel room and stubbing it out with the toe of her pointed shoe.
"No. Never," he stated stiffly, not being able to look directly at the woman. His heart was racing and it was becoming increasingly difficult to breathe.
"Don't you worry, sonny. Grandma knows just how to make a man happy," she smiled a gummy smile at him.
Wonka just nodded and clasped his hands tightly in his lap. She did have one tooth. It was brown and jagged, but it was there.
I know we talked about rates, but you never told me what services that you want."
He thought he was going to puke, "Just, uh," he wiped the sweat that was beading at his forehead, "Just you know. The uh," he coughed, "You know."
"Just a basic fuck," she stated crudely, "No blow job? Golden showers? Eating your ass? None of it?"
Wonka shook his head, "Just the basic," his voice was barely audibly.
"Ah, Willy. You're making my night easy. Generally when Johns come to me it's because they are into some freaky shit," she smiled at him, "Got a rubber?"
He swallowed hard, "A what?"
"A rubber," she repeated, "You know a condom. It's like a glove for your Johnson."
"My Johnson?" he questioned curiously.
"Your dick!" she barked, growing increasingly impatient.
"I don't have one of those," he stated, fidgeting nervously.
"You don't have a dick?" she snapped, "I thought you were a man!"
Wonka closed his eyes tightly, "No. I meant a condom. I don't have a condom."
The woman groaned, "Jesus Christ," she took a deep breath, "Okay, fine," she walked over to the trashcan, "I had a John in here earlier," she said, picking the small can up and sifting through the contents before pulling out the used latex tube, "I'll be right back," she said to him as she stepped into the bathroom.
Wonka could hear the water running in the bathroom, but he didn't get up from the bed. A huge part of him wanted to dart out the door and never look back, but he felt like he was welded to the bed and he couldn't move. And a few moments later the hooker was back.
"It's clean," she explained, "Put it on."
He took the wet condom and held the cusp between his thumb and index finger examining it as if it were the most interesting thing he had ever seen in his entire life.
"Come on, young'un, I don't have all night."
Wonka finally looked up at her, a look of pure terror on his face, "Should…. Should I got to the bathroom?"
"For crying out loud!" the woman whined, "Can we get this show on the road already?"
Wonka fidgeted but pulled down his pants and his briefs so that they rested mid-thigh and he started working to condom on to the best of his ability.
"What the hell?" the woman asked, looking at his lap, "What's on your knickers?"
He looked up from his condom project and smiled, "Gunny bears!" he said happily, the first not terrified sentence he had managed, "See, I'm a chocolatier and-"
She cut him off, "Sorry kid. I couldn't care less if I tried. You ready?"
Wonka had only managed to get the condom on over the head of his penis, so most of it was just handing limply but if the prostitute didn't correct him he must be doing it right. Quickly he nodded once again looking away from her.
"Good," she said, reaching up under her skintight dress and dropped her faded and stretched out thong on the ground before straddling his lap and sinking down on him. She was holding on to his shoulders to keep herself balanced since they were both sitting in an upright position.
The candy man slammed his eyes shut, grabbed fistfuls of the blanket, and let out a shrill whine. The hooker took complete control and thirty seconds later it was all over and she was seated on the edge of the bed reapplying her lipstick and wiping herself down with a baby wipe.
"I hope you know that you still have to pay for the full hour," she informed him.
Wonka got his gummy bear underwear back up but his pants were down around his knees as he slowly curled up into a ball on the filthy motel bed. He hugged his knees to his chest as he burst into tears.
The woman looked over at him and scoffed, "Oh calm down, Willy."
But he couldn't calm down. All he could do was sit there with his underwear showing and sob.
"Can you just pay me so I can go?" her frustration was obvious in her voice.
After that night Willy Wonka went back to his chocolate factory and stayed there. It was YEARS before he could even be in the same room as a woman without bursting into tears. Thankfully for him all of the Oompa Loompas were male.