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“I can’t do that. I might hurt you!”
Her client wanted her to perform anal sex on him with the heel of her shoe.
Gypsy’s voice quivered when he 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, Gypsy 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. He was explaining that she was to lubricate his asshole with spit! Gypsy had read about rim jobs. She always thought they would happen to her, not the other way around. At 18, she was a little taken back but knew her duties. As she leaned in, she placed delicate fingers on either side of his lower cheeks. The young girl pulled them open, her nose wrinkling a bit. She had never thought of putting tongue to ass before, but this is what he wanted.
“Ready for me, Sir?” she asked but didn’t wait for a response.
Her tongue now perched between her teeth, the first punch on his entrance was like an electrical charge. Gypsy 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. The act wasn’t as gross like she thought it would be. Curling her muscle at the tip, a push forward, and she was inside of his anal cavity. All she could think was, Oh god, she was tonguing this stranger’s asshole and not even hating it.
As Gypsy pushed in and out, the tiny hole opened for her, allowing her to go to the farthest depth her tongue could reach. That small pinch of his sphincter was the only hindrance that she felt. He was tight, but Gypsy 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 Gypsy was ready. She knew that he wanted this. Was he was gay, or could this be part of a foot fetish? Either way, she rubbed the lubrication 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, Gypsy didn’t stop until the entire spiked-heel was inside. She couldn’t get any more of the shoe in his tight little starfish.
Gasping, Gypsy was 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,” he screamed.
You’re sure you want it harder?” she asked.
He called out in pleasure, bringing a side of the 18-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 calf ached from the intensity of the fuck, but the pre-cum dripping from the head of his dick was a sign he was close. 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 than 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.
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