You want to fuck Isabella's ass

"Isabella, Jacob tells me you like it up the ass? He's always bragging about it."

This is not strictly true, Isabella thinks, but doesn't explain that to you. Her boyfriend is obsessed with anal sex and starting from their third date together he pressured her into giving up her tight ass. It's what I deserve for putting out on the first date, she figured - he figured I was a slut. Well he was more or less right about that, because eventually she did let Jacob take her anal virginity.

She thought that that would get it out of his system, but that was far from what happened. His obsession just grew stronger and he wanted to fuck her ass more than he wanted her pussy. Isabella didn't put up much of a fight, she began to always clean herself thoroughly in the shower after every time she went to the bathroom in case the urge hit Jacob. She did like pleasing him. And she liked to think she was giving him some satisfaction that most women wouldn't do. So she didn't necessarily like it up the ass, but she liked that she could please Jacob by taking it up her ass.

"I'm going to fuck you in the ass, OK?"

She thought she would say no, but then heard herself say, "That's gonna cost you more."

"I'll give you $100. That's it," you say, haggling for Isabella's ass.

"For my ass! That'll cost way more."

"Maybe if your ass was less-used, but I'm sure Jacob has already stretched you out to be pretty lose!"

"Jacob's cock is like half the size of yours!" Isabella says and realizes she shouldn't talk like that about her boyfriend when she sees you smile.

"$100," you insist.

"Double it," she counters quickly and then immediately regrets it when she realizes that $200 is not a lot of money for what she's selling.

"Deal," you say and slap Isabella on her bum.

"I've never even fucked Emma in the butt, you know," you explain to Isabella. "I'm not sure she's ready for it yet, but maybe she can learn something by watch her good friend Isabella take it like a pro."

Isabella didn't know if she should be insulted that you were treating more like a slut than your girlfriend or turned on that she was giving you something you couldn't get from Emma. She settled on being turned on.

"Give Isabella the money, dear." you say to your girlfriend who is still half-wearing her dress, but has been busy rubbing her clit while you fucked your whore.

Emma grabs your wallet and takes out two $100 bills. You brought a lot more money with you, not sure of how cheaply Isabella would sell her ass to you.

"What do you think about all this, Emma?" you ask as she cash the money to her friend.

"I think it's very hot and I hope to learn a few things," she says, and you and Isabella can both easily see how incredibly turned on your girlfriend truly is.