Three days after Tiffany made him ejaculate inside her, Simon now finds himself waiting outside the door to her house. She apologized to him yesterday and said that she would like to treat him to some coffee and see if she could get to know him better. He was quite angry at her for the first twenty-four hours after what she did, but is now calmer, figuring that if he doesn't agree she can get upset and take it out on Sasha. It was a surreal experience, one that he still couldn't comprehend. Simon did say that he would take responsibility for any child that may be the result of their trust, and he meant it. He is already looking for jobs that he could take in order to provide, should he need to.

Suddenly, a middle-aged man opens the door and brings Simon right out of his brief reverie. He did knock on the door but expected Tiffany to be the one to open, which, in retrospect, is kind of dumb, given that other people clearly live with her too. Namely, her parents. "Oh, hi, sir. My name is Simon. I'm here because I have a date with Tiffany," he awkwardly introduces himself. God, he really sucks at meeting new people. Oh, he is nice enough but his tongue just always gets lodged in his throat!

Tiffany's father, Harold, stares at him for a long moment before finally offering Simon a surprising, warm smile. His kindly demeanor provides a stark contrast with his daughter's behavior. "You must be Simon," he says to the dorky teenager, extending his arm for a handshake. "My troublesome daughter mentioned you several times over the past couple of days. She didn't really blackmail you into going on a date with her, right? I heard her muttering something along that line but thought that she was probably just kidding with her friends over the phone."

Simon finds himself very surprised that Tiffany has mentioned him to her dad and awkwardly smiles, scratching the back of his neck. He wants to ask her father some questions about how Tiffany talked about him, but at that moment, the African American arrives at the door and beams at him. For a moment, Simon is awed by how gorgeous she looks in that tight T-shirt that reveals the outline of her full boobs and the black miniskirt that reaches just below the bottom of her booty, fitting snugly around the large asscheeks. Tiffany's muscled thighs almost make his mouth water as they get leave the house to go on their first date.

They get to her favorite restaurant and sit down together at the table with him still scowling slightly. Just because he's cooled his head doesn't mean Simon is now completely over what she did to him. "Oh come on, sweetie. Cheer up," Tiffany says to him. "We're on our first date, after all." She reaches over and then places her hand on the back of his, and he hates himself for feeling sparks from the contact. Why does he have to be so weak in her presence like this?

Not that he is any stronger elsewhere but usually, he isn't sweating profusely and whimpering inside. His heat just doesn't go racing at 100 mph like it does when he is with her. Tiffany seems to know full well the effects she has on him and she smirks. "Um, yeah. Just a little nervous, that's all," he mumbles to her, looking down at the utensils. "So please tell me. You did take the plan B pill, didn't you? I mean, it's for the best of you did. You're an excellent athlete with a great career in basketball in front of you, if you are planning to go professional, that is. And I want to go to college and set up a good career too."

Tiffany smiles mischievously. She did take the morning-after pill, and in only half an hour since he cummed inside her, so it's extremely effective. But he doesn't have to know that. She could have some fun. "Nope. So maybe you are now bound to me for life. That is pretty exciting, isn't it? If we have a child together, you can never leave me. Even when high school is over and I no longer have your little sister as a pawn to manipulate you with." She gives him a very flirtatious smile as she says this.

Simon gulps very nervously. But then the fear leaves his eyes as he realizes what he has to do. He suddenly seems galvanized, confusing Tiffany with his confidence that came out of nowhere. "Fine," he says to the startled ebony. "I can not force you to take the pill. But if you get pregnant, like I said before, then that is my child too and I will have a say in how he or she is raised. Neither of us are perfect, with you being a mean and manipulative bully, and me being a dumbass who started catching feelings for you, but I'm going to make sure our child is as near to perfect as I can get him."

It's only after he's already said this that Simon realizes what he just admitted to and he gasps in horror as her lips curl up into a grin. Oh, dear god. He just told her he caught feelings for her! This is so, so bad. "That is so very sweet of you, baby," Tiffany titters as he blushes and wishes the ground would open up and swallow him whole. But it won't so he is forced to sit right there and face her after his massive blunder, with no possible escape route in sight. "I'm so touched."

Simon stammers, now trying to take back what he said, but he knows that it is futile, given how earnestly he has just professed his feelings for her. No way would she buy that it was nothing more than a slip of the tongue. To be honest, neither would he believe that, after all the butterflies in his stomach. "I mean, I suppose it is only natural," the boy attempts valiantly. "We are two young people who just popped each other's cherry. There's obviously going to be an attachment forming between us."

Truthfully, Tiffany's already been very attracted to Simon for some time now. But after all the years of bullying other people, she actually has many moments where she questions herself and thinks that she is unworthy of love because of her actions, especially from someone as wonderful as Simon. All of the times she tormented other students, she was acting out, lashing out at other people because of the way she feels she has been neglected by her father, who may have always bought her whatever she wanted but was rarely home to connect with her. So she only says, "Thank you for that," instead of admitting her own feelings to Simon.

Simon can not believe he finds himself disappointed. Did a part of him expect her to say she likes him? No, that can't be it, he reasons in his mind. It's just the idea that Tiffany might find him to be just a cheap whore. So he shrugs it aside and says, "Oh, okay. I think we should just order our lunch now." She agrees, flagging down a waiter and then giving him her orders before Simon does the same. He can't get rid of the feeling that she might be hiding her feelings though, as she surreptitiously glances at him several times.

It turns out to be a surprisingly enjoyable date, in spite of the fact that he was kind of coerced into going on it in the first place. Sure, a part of it could be due to how he has never gone out with anyone before. But he still can't deny that he feels really different from how he usually does. Her presence fills him with warmth. Of course, he then recalls her treatment of his sister and other girls, and then there'd be some disgust. It makes him very confused about how he is truly feeling about her and how he should be, as they head back to her place and he says bye to her at the door.

When she is back inside, Harold is waiting. He knows he's not been as involved in his daughter's life as he ought to have been and now wishes to try to play a bigger part in it. The man smiles at his daughter. "Simon seemed like a pretty nice kid," he says to her as she sets her purse down on a desk in the living room, taking a sip from a cup of coffee. "Did you two have a good time?" It's more difficult than he thought as she seems to not be so interested in having a conversation.

Tiffany smiles lightly as she thinks about what just happened earlier. Simon told her he started to like her. That is definitely a clear sign of it being a good date. But then she frowns as she thinks of how she couldn't get herself to tell him she feels the same way. "I don't know," Tiffany finally says. "I mean, it went pretty well, I guess. Given that it's the first time I've ever been on a date before. It's still kind of difficult to wrap my head around the idea."

Harold Allens nods, thinking back to how he and his wife first met. He knows he should have spent more time with Tiffany from when she was a kid but he was always busy with his work and left it all up to his wife. The man coughs slightly before setting his coffee down and then asking, "So how did you and him get together anyway? You never told me how you asked Simon out. And I know you did the asking from how awkward he was."

This is the part where it gets tricky. She knows her father well. Harold has heard some ridiculous whoppers as a lawyer. He's practically a human bullshit detector. There is no point in trying to lie to him. It would only get her into much more trouble when he cross-examines her and forces her to tell the truth. So she decides to take it slow and reveal small bits and pieces at a time. "I just broke his sister's glasses and told her she's ugly when he showed up to defend her," she says as her father's eyes go wide. "So I told him that if he has sex with me, I'll leave her alone."

Harold is now staring at his daughter, aghast. He could not believe what he just heard from her and is most disappointed by her flippant attitude towards her own actions. "I can’t believe you are such a bitch.”

"It's not my fault I’m this way. You weren’t around to teach me to be better!”

As she walks away, back to her bedroom, the shocked graying lawyer calls out after her "I'm not going to represent you if he files charges!"

…………

A couple of hours after his date with Tiffany, Simon is back at home in his room, trying to understand the themes and motifs of 'The Handmaid's Tale.' He is most likely the only one in his Literature class who enjoys the assignment and reads the material even when not required to do so. Suddenly, there is the sound of knocking on the door. "Come in!" he calls out. Glancing up from his paperback, he is surprised to see Sasha enter. "Have a seat. Is there anything you want to talk about?" he queries, placing the novel back on his desk. She nods. "Well, go on then. You know you can tell me anything."

His little sister looks restless. It bothers him to see his sister this way, acting depressed. He has never seen Sasha with such an expression on her face before and knows that he doesn't want to see it ever again, even before knowing what the cause is. "It's about you and Tiffany," she says to him. Here it is. He should have known that this is coming. "I really want to thank you for going out with her. I really do. Thank you so much. She's left me alone and her friend has too. If you weren't dating her, then my school life would be so horrible right now."

Simon pats her shoulder reassuringly. He hates seeing her worry about something. It's the big brother instinct that made him agree to be Tiffany's whore in the first place. Well, that and the stirring in his groin that he likes to pretend isn't there. "It's okay, Sasha. You know I would do anything to protect you," he says. "Just remember. If anyone gives you a hard time, you come to me and mom and dad, okay? We're all here for you." He has actually never followed his own advice before, always keeping things from his parents back when he was bullied, but that's because he thought it's not worth getting them worried over. It's only now that he's seen it happen to someone else that he knows how problematic bullying is, witnessing it from another perspective.

She seems to be struggling to say something and he urges her to take her time if she has to, because he will always be here. He'll wait however long it takes for her to open up. It doesn't take as long as he feared though and soon she is continuing. "There is something else too, though," Sasha tells him, and he prompts her to go on. "I've been thinking about this for a time now. Her family is really loaded. She has so much money. Wouldn't it be so good if you could get into a serious relationship and then leech off her parents? It would be nice payback too."

The boy stares at her in disbelief. He never thought he would hear his younger sister say something like that to him. It is truly very disappointing and he doesn't know what to say. "Hey! Wait a minute," Simon finally manages, getting up from his seat. "Are you trying to pimp me out or something? And leech on her mom and dad? No! I can understand you hating Tiffany but her parents never hurt you. They are both innocent and you shouldn't try to get revenge on them. Leave the family out of this."

"Innocent? They raised Tiffany! Their daughter is a monster who takes pleasure in torturing others. If they had done their job properly, she wouldn't have ended up that way," Sasha cries out, getting to her feet too, squaring up to her brother. "And pimping you out? I only asked you once and you did it without really protesting against the idea! It was way too easy. Maybe you really are a whore like everyone's been saying!"

Simon glares at her. "Oh, so you're calling me a whore now? I gave in so easily because it's all for you! To protect you, my sister! That's the only reason I agreed. I thought you were better than this, Sasha." He sighs exasperated, grabbing a glass of cold water and gulping it down, trying to avoid the incoming migraine. "You know I love you. I want to protect you from her and I agreed to fuck her in exchange for her leaving you alone. And you repay me by calling me a whore like everyone else has been?"

The younger sibling now realises she has taken this too far and her gaze softens. "I'm sorry, Simon," she whispers. "I just worry about you, the way you care about me. I don't want you gaining a reputation as a loose boy who spreads his legs like it's no big deal, you know?" He scoffs in disbelief as she heads for the door. "I mean it. A lot of my friends actually think you are pretty cute. I've been promising each of them a date with you if they do me favours like completing my homework for me and stuff." Then Sasha leaves the room.

Simon sits down on his bed, looking at the empty wall, trying to comprehend what he's just been told. It's unbelievable. To be objectified by Tiffany is one thing. But his own sister treating him like an object and offering him up as a reward? That's almost as bad as he wanting him to be a gigolo and get money from Tiffany's family! He could perfectly understand if she loathes the ebony beauty, but to plot against her parents is taking a step way too far in his opinion.

He finds himself questioning if he's been a really shitty brother to let her think this way. As he lies under the covers that night, resting his body on the thick mattress and staring up at the ceiling, Simon ponders on everything that has been going on over the past several days. This is all way more than he thinks he can handle. He knows he just told her that she should talk to their parents if she's facing any trouble, but what he's facing is something he isn't sure he should tell them. In a way, Simon guesses his little sister is right. He is kind of a whore; not just with how he expressed himself with Tiffany but also how he traded sex for something.

…………

The next day, he is at Tiffany's place again, this time more willing than before. They are both lying naked on her bed, touching each other's genitals. Her fist is wrapped around his rod, tugging it gently, while he cups her vagina, inserting his fingers and rubbing his thumb across her swollen clit. "Let me eat you out again," he begs her. It's just so that she would be happy and wouldn't hurt Sasha, Simon reasons with himself, but he knows that that's not true. Deep down in places he doesn't want to think about, he really likes her a lot now.

Tiffany shakes her head, confusing him. She is still pumping his...