"Ok, I did a Little prep for this earlier, but you've got to finger my asshole a little to open me up before we try to shove Gigantor in there. That ok?"

“Is it weird that it successfully stokes my ego when you call my cock Gigantor? And yes. It's very ok. Fiona?" He turned to the cat-girl and offered his hand. She had procured some more of the oil and stood beside him to assist in the act.

Fiona obediently poured the oil across his fingers, and he made sure they were good and slippery before turning his attention back to Janette.

"So I just make a fist, shout shoryuken, and then go for it, right?" he asked.

Knowing that she was going to try to take his cock in her butt had made her more than a little tense, and his words managed to successfully melt that tension away with a Loud Laugh that caught her off-guard.

“Sure, you could try that, if you wanted to get kicked back on your ass again. Ooooh!" She yelped when she felt his fingers sliding up between her rear cheeks to gently press against her tight rear hole.

Slipping his other hand beneath her, along her waistline, and down between her legs, he began to gently massage her pink folds whilst drawing tiny circles around her asshole. Each time he reached the top of the circle, he pushed gently against her resistant little rosebud. The first few times he felt her instinctively clench against the potential invader before she closed her eyes and released a slow, steady breath. On his next push, he watched his fingertip disappear into an incredibly tight spot. With a little nod to Fiona, he watched as the girl poured a drop of oil down between those creamy cheeks to further lubricate his fingers and the inside of her ass.

“Holy fuck you are tight back here, Jan. I'm not sure this is going to be physically possible."

“Dammit, Greg. You just helped beat up a pack of pissed off orcs and now my butthole is making you nervous? Man up already!"

“Yes, ma'am." He exchanged a suitably chastised look with Fiona.

“I think I can give him some more incentive," Fiona offered before ducking down to swiftly wrap her Lips around his cock.

"I don't exactly Lack for incent- Oh, ok you're doing that now.

That's... g-good." It was his turn to take a deep breath to control his reaction to the girl's talented tongue wiggling against his granite-hard shaft.

“Push a little harder, Greg!" Janette encouraged. "C'mon! Give it to met"

He was still teasing her pussy with his fingers, and given how wet his hand was, he guessed that her encouragement was utterly genuine. Sticking with what worked, he did the same thing as before. Removing his finger from her butt, he rubbed a wet Little circle around the hole and waited for her breathing to relax once again. Once he knew she was ready, he pushed. This time he went all the way in to the second knuckle before he had to stop, and she let out a little squeak at feeling him inside her. Playfully, he wiggled his finger to test the limits of its new enclosure. She actually squealed at the sensation, and he made sure to rub her pussy a Little faster

"Oh baby, that feels good!" she cried out, turning her head back over her shoulder to look at him.

He took that opportunity to push further into her once again, finally managing to plant his entire finger in her asshole. She cooed at the sensation, and then let out a little breathless squeak again when he wiggled his finger in its tight confines. Gesturing down toward Fiona who was now happily bobbing her head on his cock, he silently pointed to the oil she still carried. After getting somewhat overly-focused on her cock-swallowing antics, she remembered what they were up to and slipped the hard Length from her mouth to stand up once again. She saw Gregory's finger pushed inside Janette's ass, and her eyes widened in surprise that the girl had taken it all. He nodded toward Fiona for her to begin pouring the oil again. When she did he finally moved his finger in and out of Janette with slow, careful strokes in time with her breaths.

Once he felt the oil all the way inside her, he began to slowly finger her ass whilst pressing a second finger just beneath the first. An enthralled Fiona helpfully poured some more oil on his fingers before he pushed that second finger inside Janette to join the first.

! Hold on a sec." Jan noted before drawing her Lower Lip between her teeth and closing her eyes tight. After a moment of fierce concentration, she once again released a slow breath and relaxed around his probing digits.

“Ok, that's alright. Go slow again for a little while, ok honey?"

He nodded to her and did as she asked, although his fingers shifted to concentrate on rubbing her clit whilst he slid his two fingers in and out of her rear hole. Before too long, he was once again managing to push inside her without too much resistance whilst she accommodated to their presence.

“Alright, baby. I'm going to see if I can get my cock inside you now, ok?"

She nibbled her lower lip again, but nodded with a determined resolve. Turning to look at Fiona, he stepped back to prominently display his full-mast.

Do you want to do the honours?" he asked.

"Huh?" Those feline green eyes widened in shock.