Richard gives her time to get used to things first

"Ow ow ow ow ow..." Anne was starting to say it to herself as a sort of mantra. A burning and a painful pressure spread through ass her with every thrust.

The initial shock had worn off, and now she was starting to try to get used to it somehow. It felt like she was... pooping? But backwards. Paradoxically, she was worried that she might be going to the bathroom right now, even though she knew that was impossible with daddy's cock taking up all the space in her ass. But it sure felt like it.

It couldn't have been long, but it seemed like it had been going on forever. Time seemed to warp while she squeaked with every thrust. Once, she felt him push into her and cum in her asshole, but he didn't stop. He just paused for a moment, and then kept on fucking. She heard her daddy start to speak.

"Mmmm. Your fucking ass is so tight. I guess now you can say I've cum in all your holes, babygirl." He slapped her ass, hard, as he said this. "It sounds like you're starting to get a little used to it?"

"Ow... a lit... ow... a little. It doesn't... hhhng... hurt as much as earlier, but could... uhhn... you go softer, daddy?"

"No, babygirl." And Richard increased the intensity - pulling almost all the way out, then slamming himself as deep as he could go. He felt like her tight asshole was truly **** his cock to ****, but he kept going. "This is the first part of your punishment. I'm going to teach you to withdraw from the feeling of cumming while I'm inside you. After a little while, this is going to start to feel a little good. I want you to tell me when that happens."

"OW fuck!" Anne felt herself start to cry a little. This new pace felt like she was... well, shitting a red-hot iron rod. "I don't think that's... I don't think that's going to happen. This hurts so so so bad, daddy."

"Don't worry, baby. It will. Just endure until then."

And so Anne tried to relax. It felt like days passed, but it was probably just a few minutes. Eventually, though... as daddy had said, it started to feel... a little good. "I think... I think I can feel what you're talking about. I think I can..."

"I'm so proud of you, babygirl. Good job. Now, I want you to finger yourself while I fuck your ass. Tell me when you get close." Anne smiled, and Richard realized that she seems to have forgotten that this was, overall, going to be a punishment. Well, she'd remember soon

Anne slid her fingers under her and started rubbing her clit violently. She actually started to feel... pretty good. She found that she was starting to love the feeling of daddy slamming into her asshole. She started to moan.

"Oh, babygirl. Sounds like you enjoy being my little anal whore. Keep it up."

Anne kept rubbing her clit, getting closer and closer. Finally - "Oh, fuck, daddy - I feel like I'm starting to get close."

"A little while longer like that and I'm gonna cu -"

"No, babygirl. You may not cum tonight." And upon saying this, Richard bottomed out into her butthole and came for a second time. Fuck, those pills really did the job. "You seem to have forgotten. You've been naughty, and this is a punishment." Anne's face fell. "No. Cumming." Richard said as he moaned into her ear and ground his dick into her ass.

He pushed in his dick as deep as he could get it, hearing her whimpers as he lost himself in pleasure for a moment.

Then he picked up once more, fucking for all he was worth. "Alright, babygirl. You say you're close. Time to start the second phase of your punishment."

"What do you mea... GUH." Anne's voice cut out as something... new... happened.