Olivia Rose had been teasing and tempting you for weeks, promising you a night of anal pleasure on JOI Humiliation. But this bad girl decided to throw a twist into the mix… And now here you were, standing in front of her as she confidently wielded a strap-on dildo. Wait now… YOU are going to be the one who gets anally penetrated? For the very first time? Can you handle your first time pegging with Olivia Rose?
Your mind flashed back to all the times you had begged past girlfriends to let you fuck their tight asses. But they always refused, claiming it would be too painful or they just weren’t into it. But Olivia was different. She not only promised it, but she seemed excited about it. And now you know why… because YOU are the one getting fucked!
“Remember how I said if our date went well enough tonight, you’d get some anal?” Olivia purred, breaking through your thoughts. “Well, I hope pegging is the kind of anal you were thinking about!”
She slowly approached you, the strap-on bobbing between her legs. You felt a mix of desire and fear coursing through your body. This was uncharted territory for you, and yet you couldn’t deny how turned on you were.
“I’ve never been fucked in the ass before,” you admitted, feeling a bit vulnerable under her intense gaze.
“Well then, I’ll make sure your first time is nice and gentle,” Olivia assured with a seductive smile. “I’m going to spread you wide open and pop my big dildo in. And trust me, it’s going to feel so good.”
You couldn’t take your eyes off of her as she moved closer, her long red hair cascading down her shoulders and bright red lipstick accentuating her full lips. She looked absolutely stunning and powerful at the same time.
Without another word, Olivia pushed you onto the bed and climbed on top of you, straddling your hips. She reached behind her back and made sure that the strap-on was perfectly secured around her waist, making sure it was extra secure before leaning down to kiss you forcefully.
Olivia pulled away and looked down at you with a mischievous glint in her eye. “Are you ready for this?” she asked, her voice husky with desire.
“Yes,” you breathed out, barely able to contain your excitement.
With a quick motion, Olivia positioned herself between your legs and slowly began to tease your asshole with the tip of the dildo. You gasped at the sensation as she rubbed it up and down, coating it with lube and preparing you for what was to come.
And then, without warning, she pushed forward and entered in one swift motion. The initial pain was intense, but it quickly melted away as Olivia began to move inside of you. It was unlike anything you had ever experienced before – a combination of pleasure and slight discomfort that only added to the intensity of the moment!
She started off slowly, giving you time to adjust to the new sensations. But soon enough, she picked up speed and began thrusting into you with a steady rhythm. The feeling of being filled by her was indescribable – a mix of fullness and pleasure that had you moaning uncontrollably.
As if sensing your need for more, Olivia reached down and started stroking your cock in time with her thrusts. The dual stimulation was almost too much to handle, but you couldn’t bring yourself to ask her to stop. You wanted this – needed it.
And if you needed THAT, there’s so much more for you to enjoy on JOI Humiliation, not just with Olivia Rose but with her whole cohort of naughty babes! Join JOI Humiliation today and explore your shame kink!