“I can’t do that. I might hurt you!” He wanted me to perform anal sex on him with the heel of my shoe.

Her voice quivered when he asked. He had asked her to fuck his ass with the pointed heel of that stiletto. To push in the tip and manipulate his tiny entrance till she reached the full 5 inches inside. Was this even possible without causing damage to his anal cavity?
He was paying for this, so turning him down would not be acceptable. If he told the service she worked for that she was not compliant. Bianca would lose her job on the spot and her name in the Escort business ruined.

“How do we proceed with this anal sex?”

Still a bit nervous, the man handed her a bottle of lubrication. Explaining that she was to lubricate his asshole with spit! Bianca had read about rim jobs. She always thought they would happen her. She never thought about the reverse use of them.
At 19, she was a little taken back, but knew her duties. Leaning in, her delicate fingers on either side of his lower cheeks. The young girl pulled them open, her nose crinkling a bit. She had never thought of putting tongue to ass before, but this is what he was asking for.
“Ready for me, Sir?”
Asking, she didn’t wait for him to respond. Leaning in, her tongue now perched between her teeth. The first punch on his entrance was like an electrical charge. Bianca didn’t know what to expect, but it wasn’t that. He was spotless in hygiene, and the hint of old spice was all she smelled. This wasn’t gross like she thought it would be.
Curling her muscle at the tip, a push forward and she was in. Oh god, she was tonguing this stranger’s asshole and not even hating it. Pushing in, and out, the tiny hole opened for her, allowing her to push to the farthest depth her tongue could reach. No shit, not gas, not even an odor offended her.
That tiny pinch of his sphincter was the only hindrance that she felt. He was tight, but Bianca was sure there had been more in his ass than a tongue, or even a shoe. His moaning was a dead giveaway. As he uttered obscenities. Her mouth ached from the consistent deepening into the anal cavity.

“Stop! Lube the heel of your shoe and slip it into my asshole. I’ll hold the chair and you get that beautiful red heel deep in my shithole. I need a anal fucking!”

His words sent shivers up and down her spine, but Bianca was ready. She knew that his wanted this. He was gay, or could this be part of a foot fetish? Either way, she rubbed the wet onto the heel, leaning back on the bed and lifting her foot to his asshole.
Resting the tip on the top of his crack. She pushed against his entrance, groaning as she pushed inside of his tight walls. Closing her eyes, Bianca didn’t stop till there was nothing left. She couldn’t get any more of the shoe in his tight little starfish. Gasping, amazed, this Man was moaning and telling her to fuck his ass harder. What if she punctured his walls? A shoe was not a sex toy, well she thought.
“Harder? You’re sure you want it harder?”
He called out in pleasure, bringing a side of the 19-year-old that she hadn’t explored yet. With increase momentum, her foot slammed against his anus with a loud thud. Something came over her then. A part of her she hadn’t see yet emerged from the teen. A filthy mouthed little whore!

“You fucking like it in the ass don’t you. You’re a bitch! Take that fucking shoe in your asshole bitch boy.”

Her foot pumped into him deep, hard, and like she was stepping on the gas pedal. So much so that his cock started to drip cum from the tip, spilling out like a trickle of white cream. One more groan from him and he lost it.
Her heel pushed to the hilt and he shot all over the chair. Rope after rope, the cum pumped from his elongated shaft. Pouring more then she had ever seen. It was mesmerizing to watch, but deep inside of the young beauty. She was quite satisfied with her first time anal accomplishments.