Younger Man And Older Woman

“Tell me again why my heels turn you on” Ana started to gently kiss her way down Simon’s body, starting with his neck, collarbones, nipples, then his stomach.

Simon moaned, enjoying the feeling of Ana’s lips, remembering last night when they had made out after coming home from dinner and she had left lipstick all over his torso.


He had regretted taking the marks off in the shower, before bed. Maybe next time he’d leave them. Or at least leave one. He shifted over to his back, gently spreading his legs to give Ana room.

With his eyes closed, he was surprised when she changed directions above him. Instead of kneeling between his legs, she straddled his torso, knees bent, legs spread so he could see, and touch her pussy, clit and ass, but not so close that he could raise his mouth and lips to them.

He tried anyways, his arms wrapping around her legs so his palms were on her upper thighs.

She shook her ass gently, and resumed gently stroking his cock, just touching the tips of her fingers to the shaft. On every stroke, she revealed the head of his cock, then let his foreskin slide up again to conceal it. “Mmm, honey. No. I want you to tell me, while I enjoy your cock”.

Simon blushed, but lay his head back down on the chair again. He absolutely loved hearing Ana using words like that. But he knew she was serious, and she wanted him to answer.

“Again?” Her heels were right by the side of his head, and he brought his hands up, touching her shoes, her feet, tracing the details in his fingers.

Ana leaned forward a bit, “Yes. You didn’t really answer, last time” she kissed the side of the shaft, releasing it to take Simon’s balls into her hands, and gently massage them.

“I love how you look when you’re wearing heels” he said softly.

Ana gently rubbed her cheek against the shaft of his cock, feeling it’s length against her face. “Louder, honey. I want to hear you, and nobody else can hear us. And” she kissed the shaft, three times in succession “more details. Be explicit”

“I love how you look when you wear heels. What they do to your legs, to your ass. I love feeling them against me when you wear them” Ana smiled, and pulled down to show the head of his cock then kissed it, and ran her tongue around around the rim of the glans.

“Tell me how you want them to touch you. And how you want to touch them” Ana instructed, then started taking his shaft into her mouth, slowly lowering her jaw, working to take in as much of his length as she could. Simon just mumbled, until she very gently touched his shaft with her teeth as a reminder.

“Oh God, it’s hard to focus.” he shook his head, and his hands found and gripped the ankle straps of her shoes.

Ana just breathed in gently, easings another few millimeters of Simon’s cock into her mouth, and using the tip of her tongue on it where she could.

Have to focus, and answer, Simon thought. He’d never experienced anything like this before.. Maybe if he answered she’d do it again. “I want to feel your heels digging into my back as I eat you out.” He paused, as she wiggled her mouth back and forth, taking even more in.

“I want to feel them on my legs, as I fuck you. I want to feel you rubbing my cock with your cock through my pants when we’re out for dinner. I want you to hold onto your heels, as you ride me.”

Ana started slowly pulling his cock out of her mouth, playing with his balls with one hand as she did so.

“I just love knowing you wear heels, it’s so hot” Simon said, finally. Ana grinned “I know honey. I love it so much when you tell me these things.”

She took just the head of his cock into her mouth, sucking on it and using her tongue, while stroking the entire length of his shaft. Satisfied with his hardness, she gently hit her face with the length of his cock, getting precum in her hair and eyebrows.

“God, you’re so wet” Simon murmured. He pulled her back towards him, and she finally relented, sitting up and allowing him to steer her so he had the best access.

Ana tried to slow her breathing, as Simon let go of her for a second. Then, he was touching her again. His mouth was on her pussy lips, his tongue gently parting them.

His left hand was on her clit… and suddenly she felt his right hand, with a good amount of lube, start teasing and playing with her ass.

“Oh Honey” It was Ana’s time to be surprised. She had mentioned her love of anal play a few days before when her new butt plug had arrived in the mail, but it hadn’t come up again, and she hadn’t had a chance to try it out.

He applied more lube, and then suddenly she felt the warm, firm pointed end of one of her new glass plug putting pressure on her anus. “Oh, honey” Ana repeated.




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