Give him advice

Fuck it she thought to herself. Henry was the one that that agreed to this, so why shouldn't she live up to his side of the bargain and give Derrick some advice. It would also allow her to help iron out some annoying shit she's been having to put up with and if he's going to keep trying she might as well make it more enjoyable.

Henry > "Ok first thing you're going to have to do is drop the Assley name. She hates it, and you're going to need to give her a heartfelt apology."

Ashley sat there smirking to herself. She doubted he'd even be do that simple task, and she can just blow this whole thing off.

Derrick > "Wow she really hates that? I thought it was her just being modest and playing it off. You know she's got the best ass at school, why is she embarrassed about it?"

Ashley had to read that a few times as she was stunned. He really thought her ass was the best in the school? She always thought he was just teasing her about it. She looked back at her big ass, trying to admire it. She just couldn't see it, she had too many negative emotions around it to see it as looking good. Still it made her feel a bit better knowing the nickname was a attempt at a compliment, even if it was a horrible one.

Henry > "Those aren't the type of compliments she likes to get, though you should definitely compliment her. Her makeup, her pretty face, her hair, her smarts, hell even her tits would be something she'd like more."

Ashley stressed this in the text, even if he did like her ass that wouldn't change how annoying the nickname was! She could put with him drooling over her tits all night if it meant no more Assley comments.

Derrick > "Dude this is all solid advice, there's no way you're getting my car at this rate."

Being reminded that her boyfriend was betting her over a car just reignited her fury. She wasn't just going to make things better for her, she was going to make things worse for him.

Henry> "Also she loves confidence so just hit on her right in front of me, honestly if you put me down a bit it will actually improve your chances."

She felt a little bad writing that, but couldn't help but smile. It would serve him right, if he was going to wager her, he should get punished by guys that wanted her.

Derrick> "Lol that won't be hard to do, no offense. Maybe I'll even let you be in the room as she rides my cock if you're lucky!"

Ashley actually laughed at that comment. Imagining her riding Derrick while they both teased her boyfriend for getting exactly what he deserved would be too perfect, she then realized she was actually considering letting Derrick win this bet. She didn't have long to contemplate this before his next text

Derrick >"Why don't you send me a preview of what I'm going to be fucking at the party?"