Painal to take Hannah's anal virginity

After a good dinner, Jack left the girl alone for a while. He was stuffed, and Hannah needed to shower. He intended to take her ass next, and he wanted her to be clean for it. It would also be a lot more fun to ruin her again before she went to bed. So he let Diana and Hannah hang out while he went for a walk and spent some time on the computer until it was getting late. Hannah was clean and getting ready for bed, so it was time to get to work. He went upstairs and entered the guest bedroom as Hannah was undressing.

- Could you at least knock, Hannah asked with a hint of annoyance.

- Hannah, I think we're past that stage. I fucked you in the living room. I don't think seeing you naked is much worse.

-Whatever. Do you need something? I was getting ready to go to bed.

- Yea, I think I can go one more time today and figured you could help me with that. You are my guest after all so that would be the polite thing to do.

-Sure, what do you want? A blowjob or my pussy?

- Neither. I've had my eyes on your ass since you arrived and I think it's time my cock to find out how tight it is. Just get on the bed on your stomach and let me do the rest.

- Y-you mean anal? Won't that hurt?

- Don't worry, I'm sure you can handle it. Besides, remember you're my guest. The least you can do is sacrifice your comfort for a few minutes to help me.

Hannah was visibly nervous but she got on the bed, spreading her legs and waiting. Jack grabbed a bottle of lube from the dresser and climbed on the bed. Spreading Hannah's cheeks with one hand, he poured a generous amount in her crack before pressing his thumb inside Hannah's asshole to work some of the lube in. She shuddered and whimpered, and Jack's cock became rock hard, eager to spread her tight ring. He pulled his thumb about and lubed his cock before getting in position, ready to fuck Hannah's ass prone bone. His penis slid between Hannah's cheeks and the tip pressed against Hannah's virgin asshole. Jack's cock was painfully hard at this point, and it was time to transfer this pain. Jack thrust.

Hannah cried out. Jack's thick dick split her open and felt much bigger going through her ass than it did in her pussy. The stretch was painful and knocked the wind out of her. Her anus had definitely not been built to be penetrated this way and every one of her nerves let her know. Jack had only pushed in a few inches, and she was already thinking about tapping out, but she couldn't. What would people think of her if she acted this way when she was a guest? Hannah grit her teeth, and tried to brace herself for what was to come.

Jack held himself halfway inside Hannah's amazing ass. The discomfort that had been building inside his cock vanished and was replaced by a feeling of pure pleasure. He could feel his cock stretching out the girl's tight ring and could only imagine that all the bliss he felt, she felt as pain. The thought of it made his cock twitch with excitement, and even that made Hannah react. His cock completely dominated her ass. He grabbed Hannah's arms and pinned them under his hands. He was ready to start pounding.

Jack pulled out completely before thrusting back in. All the way in. It felt exactly like both of them expected it to: excruciating for Hannah, and heavenly for Jack. But this time, Jack wasn't staying still. He started pounding into Hannah, trying to get the most out of her asshole's first time, always thrusting his full length in and out of the poor girl. His pleasure was the only thing on his mind, and if it required a rough painal session to maximize it, then so be it. The petite blonde just had to endure. Hannah was being pretty loud about it, so he moved one of his hands to press her face into the pillow. He didn't want to bother Diana and Katey, but they clearly knew what he was doing with Hannah by now.

Jack slowly felt his climax build up. Normally, with how good this felt, he would have been done a while ago. Thanks to the multiple loads he had dumped in the girl during the day, he was able to last a lot longer, but it was time. He gave a few last shallow and quick thrusts, using her ring to stimulate the tip of his cock, before plunging one last time, shooting his load deep inside her ass. He emptied every last drop he still somehow had inside him before pulling his dick out, leaving Hannah's asshole a gaping, leaking mess. Jack smiled. That's how you properly deflower an ass, he thought.

He let go of the girl's head before grabbing the pillow which was now wet with tears. He rubbed his deflating cock all over it, coating it with the mixture of fluids on his cock and cleaning himself with it. He threw it back at Hannah, who just lay still, trying to recover from the intense anal fucking she had just endured.

Jack got up and left without a word. He took one last look at the girl before leaving the guest bedroom. This had been a great day, he thought. His cock got to taste all of Hannah's holes in a single day. Better yet, he still had two months with this nice little fucktoy. He went to the bathroom and then to bed, thinking of all the ways he could use Hannah's body.