"I wouldn't," is let out in a quick, low breath before he breathes in deep and starts lowering Charlie the rest of the way. Honestly, if he thought any of this would be painful other than what is sure to be a dull ache later, this would not be happening. Charlie is precious to him. So much more precious than any sex or dream.

But as it is, his dick is disappearing into Charlie's ass, getting squeezed to within an inch of his life, and by the time he puts Charlie down, by the time he bottoms out, he almost writhes underneath him.

"Do you- can you- does it still feel good, Charlie?"

His hand and the tentacles go around the back, cup the cheeks of his ass, and lightly knead them against his length. His hips haven't moved yet, at least as best as he can keep them.