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“Um. I kinda wanted to watch, is that naughty?” she asked so sincerely he couldn’t fault her in the least.
“Not naughty at all. How about you hold his cheeks apart while I lube him up. Then once I’m seated, take up the position? Would that work?”
“That’s the best of both worlds,” she said with a grin as she crawled backward to kneel up beside her bestie. “Like this, Daddy?” she asked, pulling the globes of Sammy’s ass apart.
“Exactly like that,” Jackson praised, not missing the shudder that ran through Sammy when he heard the click of the tube being opened. Moving a bit closer, Jackson raised the tube and with a squeeze of the plastic, allowed a stream of the oil to fall at the very top of Sammy’s crack. He was expecting the slight jerk as the cool unguent surrendered to gravity and slid slowly down the crease to cover and drip into Sammy’s dark, puckered hole. Though Jackson had spent several minutes licking and probing the opening, he knew it hadn’t been enough. Snapping the lid closed, he dropped the tube on the bed and while Maxie seemed mesmerized by the oil, he simply dipped his finger into it and then pressed it into Sammy’s anus. Sammy moaned and Maxie smiled.
“I think he likes that, Daddy,” she said, “but I don’t think you’re going to fit. If you know what I mean?”
Jackson chuckled. “I do, and just like your kitty, his hole will open with a little encouragement.” He added a second finger, scissoring the two apart in order to urge the tight muscle to stretch and relax a bit. Maxine remained quiet, the only sounds Sammy’s soft moans and the squishy noise of the slippery lube being worked into and around his bottomhole.
“Are you ever going to do that to me?” Maxie asked, her face turning pink as if she were ashamed of having the audacity to even ask.
“Have you ever had a man in your bottom before?” he asked.
“No, it’s always scared me, but now—”
“Now,” he prompted when she cut herself off.
“You’re being so careful to make sure he’s ready even though you’ve allowed us to come twice and your cock has been hard for a really long time. It’s not as scary, now.”
“I’m glad to hear that, little one. To answer your question, yes, I do plan on claiming your bottom and your mouth just like I claimed your kitty. There won’t be a hole left unexplored for either of you. Does that help?”
“Yes, Daddy,” she said with a soft smile, her nipples drawing even tighter at his words.
“Good,” Jackson said, pulling his fingers free and moving to grip his cock.
“Can I put it in?” she asked. “You let Sammy put it in me.”
“I did,” Jackson confirmed, moving to replace her hands with his, spreading Sammy’s cheeks apart another inch.
“Sammy, are you ready for me to take that ride I promised you?” Jackson asked as small fingers wrapped around his shaft.
“So ready,” Sammy said.
With a smile, Jackson nodded and let Maxie guide him to his target. She was definitely concentrating on hitting the mark, not releasing him until the very tip of his cockhead was snug against Sammy’s anus.
“I think you’re good to go,” Maxie said, looking up to meet his eyes.
“I think you’re right,” Jackson said, waiting until her eyes dropped before he began to push inside.
When Sammy groaned loudly, Maxie shuddered and looked down at him.
“Does it hurt?” she whispered.
“In the best possible way,” Sammy said, his ass pushing back to help impale himself.
“Go on, little one. Get under Sammy and let him eat your sweet kitty.”
“Okay, Daddy. That was really sexy.”
Jackson chuckled when she rose up to kiss his cheek before scooching over to slide her hips beneath Sammy’s head. Gritting his teeth, Jackson waited until he watched Sammy’s head lower and heard the first moan of pleasure coming from his Little girl. Only then did he begin to push forward again.
Once he was finally balls deep, he paused, forcing himself to hold still. Not entirely for Sammy’s benefit as his body adjusted to the penetration, but partly for his own. He knew if he moved right now, he was going to embarrass himself like some untried teenager. Thankfully, he had something almost as pleasant to focus on as he listened to Maxie’s moans and watched her fingers gripping Sammy’s hair as he feasted. Jackson knew just how good she tasted and how wonderfully his Littles both gave and accepted pleasure.
“Oh, I’m gonna come.”
Maxie’s declaration had Jackson reaching down to wrap his fingers around Sammy’s erection. “We’ll all come together,” he said, pulling back only to thrust hard into the heaven that pulled his cock deep. No longer concerned about coming too quickly, he continued to withdraw and thrust back in as he pumped Sammy’s cock. When he felt his balls drawing up tight against his body, Jackson bellowed, “Come now!”
