whenshewasnice | Windsor Arms Hotel, Toronto, Natalie's Canada, Tuesday

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Windsor Arms Hotel, Toronto, Natalie's Canada, Tuesday

It was New Year's Eve, and time for Natalie to make up for the Christmas she'd managed to miss almost entirely. And what better place to do that than at a lovely upscale hotel, somewhere far away from almost everyone she knew?

Yeah, she was standing in the lobby of the Windsor Arms Hotel, win Toronto. She'd already handled check-in (including the part where she aggressively used the might of her charm stats to convince them Moxy wasn't going to be any trouble at all) and sent all her stuff upstairs to the suite. It was just her, waiting for Jim, looking every bit the barely adult politician's assistant on vacation that she was.

Those were some killer heels.

[ooc: NFB, for the boy!]

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That was when she moved to actually push one finger in. Not too deep, not all at once, though.

See, reassured.

Jim gasped and bit down on his lip. It wasn't painful but it was different. Very different.

"Keep going," he said, voice steady. "I'm fine. I can handle it."

"Okay."

Okay. So, she pushed that finger deeper. Pulled it out a bit, only to push back in. Nothing too fast but it was giving him a taste of the movement.

And Jim was still relaxed and still getting used to the sensation. It was new and it felt different but it didn't feel bad. He kept still and relaxed, feeling her finger move in and out and sighing as it did.

Natalie kept up the movements, though she made a few experimental pushes deeper a couple of times. Still rubbing his back with her other hand.

"Good boy."

Snark never went amiss.

"I'm a man."

And he couldn't resist that even as he gasped again when she went deeper. It was starting to tilt into feeling good. No pain and that was really helping.

"Mm, a manly man, too," Natalie agreed. Finger still moving. Another one just barely teasing him at the entrance, once or twice. "I'll still call you a boy, though."

"Jerk."

That was all he said because he was focusing on what she was doing with her fingers and how it felt and how he needed to keep relaxing.

"Jerk," Natalie agreed again, like it was an endearment. With their history, it was. She kept pushing and pulling back in silence for a moment longer.

"Think you can handle two?"

"Two and more," he said because he was cocky. "Come on, I can take it. Do it."

"You are so arrongant."

And she had a thingy for cocky pretty boys.

She was still going to go with just two fingers for the moment, stretching him out that little bit more. Thrusting with the same pace as before.

"And you love that."

When she added the second finger, Jim tightened up for a moment but relaxed almost immediately. It was just new and he was fine. He felt a little fuller and it was starting to feel a little more pleasurable now.

"Keep going."

"I do. Especially since it's warranted."

He was doing nicely with staying relaxed. So, she even felt comfortable giving him a few slightly quicker strokes now.

"I am pretty amazing," Jim told her, curling his fingers into the sheets briefly. He breathed a little quicker and even pushed back against her fingers subtly.

Subtle or not, it made Natalie smirk to herself.

And maybe push a little deeper again on the next stroke, too. "Yeah, you are."

"Thank you."

Jim was always willing to take a compliment even when her fingers were in his ass. He didn't care. Besides, he was adapting quickly and enjoying the sensations moving through him right now.

"Keep going."

She was slow, okay! And he knew she was being that way on purpose and he appreciated it but still!

Natalie huffed out a chuckle. "You are the least patient person to go slow with," she said. But, he was doing good and reacting well, so... Yeah, she slowed down again to add in a third slim finger.

"Last stage before you get the real thing. And I'm starting to feel like you're really going to like the real thing."

"Good."

He was both eager and curious. The third finger caused some stretching and some slight pain but he dealt with it. His muscles relaxed around her fingers and he even made a little sound of enjoyment.

"I'm fine."

Just more reassurance for her.

Much appreciated. She liked that sound, too. It was encouraging, and something she was hoping to hear more of. She kept her fingers sliding in and out.

For something a little extra, she reached down between his legs with her other hand. She could give his balls a little attention, a little feel.

"Oh, Jesus," Jim hissed, surprised. Good surprised, though! He made another sound, a little moan and pushed back against her fingers again.

"Yeah," Natalie murmured. "Thought you might enjoy that."

So she was going to keep doing it for the moment. Attention on two different spots, both meant to bring him pleasure.

"Yeah," he breathed because he did enjoy it. He even reached a hand down, gave his own cock a few strokes just to keep him as amped up as possible. He felt good. Very good right now.

And Natalie didn't miss that. "That's hot." It was. It sent a shiver down her spine. It also got her to push a little deeper again.

"Good." He kept doing it, jerking his cock a little harder and moving his hips towards his hand and then back towards her fingers. "Come on, keep going."

Now, with the extra stimulus, he was really aroused and wanted more.

It also happened to be the hottest thing Natalie had ever witnessed.

She licked her lips. Smirked. "You want to get fucked?"

Technically, that was happening even now, but he knew what she meant.

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