Over the next month, Blair takes her sweetheart Charles everywhere she goes. The two of them are practically attached at the hips. She has grown to love him and he has also fallen for her. It was, as she expected, not too difficult. After all, she is only one of the most beautiful girls in the city, and also extremely charismatic, with a witty personality to boot. Charles never stood a chance and was hers before he even knew it. He has been ever since the day she first saw him at that party, all alone and scared, waiting for her to swoop into his life and sweep him off his feet.
"Everything is just perfect," Blair tells Anna as the two young friends have some biscuits together in Anna's garden, basking in the sunlight for an hour while Eric is learning some cooking tips in the kitchen with his father in law. Mr Goldberg has been very kind to him in sharing some new tips on how to prepare steak, Anna informed Blair. "Charles is all I ever wanted. I can't wait to get married to him. Maybe you and I can even have a double wedding! Jenna can be your maid of honor and Lavender can be mine." Anna nods at the idea.
"Yeah, that sounds perfect. We should go get our bridal dresses designed soon," the swimmer answers. "My mom wouldn't mind letting me use her credit card for that. In fact, I'm sure she would be even more excited about the wedding than we are." They both snicker, thinking about how she had taught them the various things you can do to a guy's penis with your lips and tongue, and how to turn a boy into your personal sex slave. That's the kind of mother she is, teaching her daughter how to give the perfect blowjob. All while Mark Goldberg is teaching his future son in law cooking and household chores.
Unfortunately, things aren't going to go too smoothly for Blair and Charles as she makes one huge mistake that almost ruins everything. She has gotten overconfident about her looks and charming personality from a long time of getting all the dicks she want, and is now arrogant enough to believe she don't need a filter to her mouth, since she thinks she is able to get away with anything. Things are about to much differently from what she anticipated for the first time in her life. She is about to learn that there can be real consequences to what she says or does.
She is sitting on her bed with the boy right next to her, kissing him and holding his waist, caressing his skin as he runs his hands through her glossy hair. The girl is clearly dominating this one, her tongue making its way inside Charles' mouth as he moans. Blair sneakily moves her hands down to squeeze his ass. The way he reacts to that is so wonderfully pleasant she grins. His dick is pulsating against her thigh the way it should be.
"Charles, I'm getting extremely turned on right now," she tells the blushing teen. "Could you please fuck my ass?" She asks this very bluntly, confident that he would say yes. Guys wouldn't say no to an offer of anal from a normal girl and her heart shaped ass is just far above average. Sure enough, he nods eagerly, quickly agreeing to her request before frowning once he realizes something important and then getting up from his place on the bed. "What are you doing, honey? Are you looking for something?"
"I'll have to walk over to Walmarts to get some lubricant first," he says to her. "Otherwise the anal can be extremely uncomfortable and painful for you, and I don't want that to be the case." Blair is of course touched by the sentiment but getting impatient from all this. She just wants his dick in her asshole and she really wants it right now. Her ass is hungry for cock and he is going to give it to her, and she ain't gonna wait for him to just go get some lube. The girl just shakes her head at him. "What? You want to do it dry? But I can tear your insides and that could even be dangerous for you...."
"Baby, I've had much bigger dicks in my ass before. Yours would be fine," she tells him nonchalantly, before stopping once she realizes her words were insensitive. He just stares at her for a moment before looking at the side awkwardly. Blair thinks 'Screw it' and attacks his lips once again, trying to make out with the boy for the second time as he stands there, steering him back on to the bed. She is going to show him her ass can take him dry. She can easily take it.
But unfortunately for Blair, her callous words has dampened his mood and caused Charles to lose his erection. She unzips his pants to find a soft dick. No matter how much she strokes it, it only hardens slightly before going limp again, much to her annoyance. Blair growls angrily as she tries to pump him to get him stiff and ready to fuck her, but it does not work. It is pissing her off a lot and she can hardly hide her displeasure, about to make things even worse than they already are, I'd that is possible after saying something like what she just said to him.
"What's the matter with you? I'm offering to let you fuck my ass and you can't get it up?" Blair yells at the boy, having snapped after five minutes of failing to produce an erection. "Are you like a faggot or something?" The moment she said this she realizes that she just messed up for the second time in a period of minutes. "Baby, I'm so sorry. I didn't mean it." Too late for that now though, as Charles rushes out of the house, a few drops of tears rolling down his cheeks in humiliation.
Blair groans as she realizes just how badly she messed up. She thinks about running after him to apologize but then figures that it might not do much good to do so right now, given how fragile he is at the present moment. Instead, the girl decides she is going to go talk to Anna and ask her for some advice. Anna will be able to help her figure out the best course of action, she thinks as she drives over to the other girl's mansion. Her mind is a whirlwind of ideas about how to prevent the fiasco from becoming a bigger clusterfuck, even more than it already is.
"I really, really need your advice, Anna. I fucked up massively today," she says as soon as she's on a beanbag couch in her friend's bedroom, Anna having some coffee. Eric is not there today, out picking a new bed after Anna broke it. "Please, you've gotta help me out. You can call me an asshole later if you want to but you've got to help me first." Anna frowns at this. Blair must have done something atrocious for her to be this worried. She doesn't like where this thing is going at all.
"Go on, then. Tell me what it's all about. Did you get into an argument with Charles?" Anna questions her. She notices how Blair stiffens at this part. "What did you say to him? Tell me. Don't lie. I can't help you if you don't tell me the truth." Blair fidgets around nervously from her seat as her friend peers into her eyes, beckoning her to confide. It is shocking to see her be so nervous. This is very different from the Blair she has always known since the two were children.
"When we were making out, I got turned on and told Charles to fuck my ass," Blair starts. Anna rolls her eyes at this, knowing how much of an anal whore her friend is. "The thing is, he wanted to go get some lubricant from Walmarts. I was impatient and asked him to just fuck me dry, and told him that I've had much bigger cocks in my ass, so it wouldn't hurt at all." Now Anna is watching her friend in shock, not knowing what to say. This is far worse than anything she could have possibly imagined. There is going to be no easy way out from this mess.
"Why would you even say that? Did it never occur to you that he might get upset about it? You really did mess things up," Anna cries out at her friend, shaking her head incredulously. She tries to come up with ideas in her mind about what Blair could say or do to make things better but couldn't find any. That is how fucked up the whole situation is. She can't even begin to think about what would help. It seems so hopeless as she struggles to figure out what suggestion she could give.
"That's not even the worst part. The worst part came right after that," Blair mutters, making Anna's eyes go wide. She truly did not think it could get any worse than what she has already heard. "No, the worst part was when he lost his erection. After I couldn't get him hard again, I snapped. I called him a faggot for not being hard when I told him I'd let him fuck my ass." Anna stares at Blair in horror as she listens to this recollection. This is truly, deeply fucked up. It might just be messed up beyond all hopes of repair.
"That is just ridiculous! I honestly don't know whether I should help you or not," Anna grumbles, not wanting to have to sit here and listen to more of her friend's troubles. "Well, I suppose you can tell him that the bigger dicks were too big and made it painful rather than pleasurable. Say that his is the right size for you." Blair quickly thanks her for the nugget of wisdom and leaves the place, going back to her own home.
She considers what Anna said to her, knowing it to be the best thing that she can do. Hopefully Charles will believe her. Blair can't lose him. He means too much to the brunette cheerleader. The girl calls him and begs him to come over so they could talk, and he agrees. The fact that he isn't angry bodes well for her, since she only has to deal with sadness, which would be much easier. No need to worry about outbursts or anything of that kind.
"Baby, please give me a chance to say me piece," she begins once he's arrived. "Yes, I've had bigger guys fucking my ass, but they were actually too big. It didn't feel very good with them. In fact, it was terrible. It always hurt. Your dick is just the perfect size for me, baby. Please, believe me." Charles takes one look at her, before smiling and throwing himself in her arms with a bright smile on her face.
Minutes later, he is spreading her large asscheeks apart, applying a generous amount of lubricant to her asshole. He shyly pokes through the sphincter with the tip of his cock, entering the anus. Feeling the orifice expand slightly to accommodate his tool before it constricts around the shaft, he cries out in shock at how good her ass feels.
"That's it, my love. Fuck my ass hard. I want to feel you cumming in my ass, Charles," she orders nastily, causing him to gasp before starting to move. He thrusts tentatively, wanting to take things slow, but she rams her buttocks backward, sucking his cock with her shithole, clenching it around his member. Her ass cruelly squeezes the poor boy's dick, defiling Charles as he obeys Blair by fucking her the way she deserves. Finally the boy I love is fucking my ass, Blair thinks to herself happily.
It only lasts five minutes before Charles screams and starts unloading cum in Blair's greedy ass, never having had anything like this before. He cries out loudly as his penis throbs and sprays semen into her waiting ass, filling it up with bucket loads of cum. The force of the orgasm leaves him very shaken and he collapses on the bed next to her.
"I love you, Charles," Blair tells him.
"I love you too," he answers shyly.
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