Progressing to penetration

"That sounds fun," said Josh, eager to get his cock more involved in the action.

Rachel stood up and motioned for Josh to sit back down on the chair. "It'll be easier with your pants totally off..." she said, tugging on them, and he let her take his pants off.

She straddled his lap, facing him with her cleavage near his eye level, and started humping him, rubbing her naked wet pussy lips over his naked hard cock.

"Mmmmm..." she moaned, her lustful eyes gazing down at him again. "Fuck, that feels good. Soooo good. Ooooh... so good to just let go and relax with a nice grinding... and I can tell from your rock hard cock that you're loving this as much as I am, aren't you Joshie?"

"Yeah," said Josh, wishing she would hurry up and take it inside her.

Rachel seemed to be thinking along the same lines. "Mmm... I wonder what it would feel like with your pleasure stick inside me... Maybe we could try it with just the tip?" she suggested slyly.

Josh almost burst out laughing. He wondered if guys actually fell for that. But he managed to keep a straight face. "Uh, sure Rachel."

The sex-obsessed MILF boss reached down and slipped the head of his dick between her wet cunt lips, which opened like a flower for him. "Mmmmm... it feels so good inside me Josh. It feels so fucking good, doesn't it?"

It did feel good, her pussy clinging to his tip as if inviting him inside. Josh pretended not to notice that Rachel was ever so slowly sliding her pussy deeper and deeper onto his cock. She took the upper quarter, then the upper half, then the upper three-quarters...

As she finally touched down balls-deep on his cock, Rachel giggled. "OH! Oops... but it feels too good to stop now doesn't it?"

She started riding up and down, up and down, her MILF melons bouncing. "Ohhhh... ohhhh... ohhhh..." she moaned, a look of perverted "conquering" triumph in her eyes. Josh found it so cute and relatable, knowing what a satisfying sense of achievement she must be feeling.

He played along, thrusting up into her to go deeper. "Oooh... yeah, I ended up inside you in such a natural accidental way, but now I don't want it to stop either!"

"Mmmmmmm... that's a good boy Josh... giving into your primal masculine urge to be ridden." The lusty busty woman rode him faster and faster, getting up a rhythm.

He pulled down her top to let her tits out again. "You're such a sexy seductress, Rachel," he flattered her. "I can't resist your charms."

"Ohhhh I know... I know what you boys are like, Joshie... You act so above it all, but when a woman knows how to handle you, your cocks are just as horny as our clits!" She hugged him tightly to her bare breasts as she fucked him.

Her slick wet cunt slid up and down his throbbing tingling swollen shaft. He wasn't sure how much longer he could last if she kept this up.

"Ohh, ohh, ohh, I love your BIG fucking DICK! OH!" Rachel screamed.

Josh suspected this world's women had more sensitive pussies with a lower threshold for what they considered a big dick, but he was happy to take the compliment. "Haha, are you a bit of a size queen, Rachel?"

"Oh, oh, ohh, you're like a walking DILDO! OH! You're just a cock on legs! OHHH give it to me you FUCKING SEX MACHINE! OOOOH!" This world's women also seemingly couldn't keep quiet during masturbation or sex, so the whole office would know she was fucking an underling again. "Give it to me harder!"

Josh obligingly grabbed her bottomless hips and thrust harder. "Yeah, you like that Rachel? Ohhhh fuck it does feel so fucking good..."

"Mmmmm yes that's it Josh... OHHH YEAH fuck me just like that, you fucking cum-dispenser!"

Her charming seductress mask was slipping as she revealed the conquering male-objectifying filthy-mouthed horndog underneath. Josh loved the conqueress as much as the seductress, having never experienced these vibes from a woman in the old world. His already rock-hard shaft seemed to somehow swell even bigger, feeling almost impossibly big and hard as if it had discovered extra veins to pump more blood into.

Rachel's eyes burned with that raw primal conquering lust. "Oh, oh, use that dick for its natural purpose of - OH! - pleasuring a woman's cunt!" She didn't seem to realize she was doing most of the pleasuring work, sliding her warm wet welcoming fuckhole up and down his shaft, even flexing her pussy muscles to better stimulate him. He could get lost in her sexy lusty eyes and horny intimate moans as his cock tingled and throbbed and twitched...

Before Josh knew it, he was cumming. Knowing she would happily take his jizz, he felt free to just zone out listening to her sexy moans, and fire jets of pure pleasure deep inside her warm pussy.