Blackmailing Bitch Ch. 01

Tom is just minding his own business as usual in the library. He is reading his copy of The Handmaid's Tale. It is the novel he is studying for his literature class. He isn't just reading it because he has to though. The teen finds it to be a genuinely interesting book and has been riveted to it from the first time he read it, unable to put the book down. He was so enthralled he even started to read Oryx and Crake, another one of Margaret Atwood's works, even though Tom had never read anything remotely resembling science fiction before. It is a massive change for the scrawny boy.

Suddenly, he could hear giggling from a group of girls entering the library. He sighs. Tom likes to come here to use the place as an escape from his troubles ever since his mom got convicted for murder four years ago. His dad also died in Afghanistan at around the same time so he had to go live with his uncle, who was in the Army like his dad but survived the war and was honorably discharged. Nobody at the school has a clue about his life. Yet now he can not just use it as a way to escape anymore as there is the sound of people chatting loudly and it is bothering him a lot. Still, he is too polite to tell anyone to shut up, even if he really wants to do that.

"Oi, can't you kids read the signs? It clearly says 'No loud noises inside the library!" the librarian thunders. Tom is bemused and turns to look.

Facing the librarian is Leslie, one of the best pole vaulters in their school and easily the most beautiful and richest girl, with her perfect face, toned body and thick ass. Her round backside has been jerked off to by many guys and she knows and is proud of it.

"We can read it and we were loud, but not as loud as you were seconds ago," she remarks. The middle aged woman glares at her as she and her team mates all titter. "Sorry, I was just having fun and messing around. We'll clear out of here now. Really sorry for us being a nuisance."

"You better go now. I can't believe how you kids behave these days," answers the librarian. "And don't wear those tight, revealing shorts here again. It makes you look like a tramp." Dead silence. It is now so quiet you could hear a pin drop.

Everyone knows that Leslie wears these short shorts since they are really tight and accentuates her curves, showing off her delicious booty. She is proud of her large ass and revels in the fact that many guys masturbate to her. Hell, she regularly posts photos of her ass in a bikini on Instagram, along with some captions encouraging guys to wank to her.

"Mrs Alvin, I find your double standard to be quite interesting," he says to the librarian, who immediately swivels her head around to face him. Leslie and her friends also stare at the usually quiet boy. Everyone in the library looks at him, amazed that he is speaking up of his own accord without being having to be promoted by a teacher.

"What double standards are you talking about now, Tom?" Mrs Alvin asks. "I'm fairly sure I treat every student in here the same way. So if you think that I've been showing preferential treatment to anyone, then speak up now please." She waits expectantly for the boy to say something, and he doesn't disappoint.

"When Gary was here yesterday, he was really loud and also wore those sports clothes right after football practice," he remarks. "But you didn't seem to have problems with that. Maybe it's because you were drooling all over him, just checking out his muscles?" He could hear snickering from others around the library as the librarian goes red in the face.

"I, um, ah, I don't, I don't know what you are talking about," Mrs Alvin now says nervously, clearly embarrassed he caught her checking out a student. "I'll let them stay here if they don't make any loud noises," she says hastily, then turns to the girls. "You can stay here if you want to."

"Thank you!" Leslie replies, flashing a very infectious grin. Then she turns her pretty face around to look at Tom, who can feel his heart skipping a beat. She whispers something to her friend and then walks over to his desk. He tries to get up in his panic but she sits down and grabs his wrist. "Sit back down. We need to talk." He gulps and obeys her.

"Um, hi," he says nervously. Leslie is looking deep into his eyes and he could feel the sweat forming on his forehead and his dick stiffening in his pants. Her round boobs thrust sexily against the top she is wearing and her lips curl into a smile as he fails to avoid sneaking a little glimpse.

"That was quite cool of you to stand up to her for me like that," she says as she twirls her hair distractingly.

"Thanks! Uh, I just thought that she was being unfair, you know, and I hate unfair treatment and stuff," he mutters, looking away from her firm, perky tits.

"It's okay, I like it when guys stare at my boobs," she tells him. "Almost as much as I like them looking at my ass too. How often do you masturbate to the pictures of my ass on Instagram?" Tom quickly shakes his head. "Oh, don't lie, baby. I know you jerk off to my ass. Every guy in the school does it."

"I really don't," he tells her. She frowns at this.

"So am I not boner material? Am I not hot enough for you to masturbate to?" Leslie asks, sounding very offended. He shakes his head again.

"You're really attractive!" he says. "It's just that I don't use Instagram. And also, it would be weird for me to jerk off to you when you didn't post those pictures with that intention in mind.."

"Baby, I posted pictures of my ass in a bikini on Instagram, knowing that I've got dozens of male followers," she tells him. "I not only know that they stroke to me but I encourage it. I want them to masturbate to me every night before I go to sleep. I want them to cum on my pictures."

"Oh wow. Well, okay. I mean, whatever gets you going, I guess," Tom says with a nervous chuckle. "So what did you want to talk to me about anyways? You said we have to talk, right? Surely not just about those guys jerking to you at night."

"Yes, I wanted to talk about something more than that," Leslie says. Her best friend Sarah leans in and whispers in her ear. Leslie giggles then says "No, Sarah! Not that soon." Then she says to Tom "Sarah just told me to suck your dick today but I think we should go on a first date first."

"I didn't say you have to do it today!" Sarah says. "I said do it soon."

"Hold up!" Tom interrupts the girls, his eyes wide. "Did you just say date? I heard that correctly, didn't I?" Leslie nods. "Wow, I didn't expect this at all! I mean, you're really beautiful, confident and popular, and I'm just me!"

"Honey, that's really sweet of you to say," Leslie tells him. "I think you are a really cute boy and I want to go on a date with you tomorrow. Would you go on a date with me, baby?" Tom could feel some guys sitting on a nearby table staring at him enviously.

"Sure!" he replies, blushing. "I'd love to go out with you." Leslie grins and then writes her number and address down on a piece of paper. She hands it to him and he ticks it in his pocket. Then he places his stuff back in his bag and is about ready to leave now.

"Wait, baby!" Leslie says. "I want you number too. Give me your number and your address." He quickly writes them down for her and she folds it and puts it away carefully. Then she leans in to kiss him gently on the cheek. After a brief moment of hesitation, she kisses the still shocked boy on his lips.

He could hear Sarah giggling as Leslie kisses him. His cheeks are burning up and when she backs away, Leslie laughs at how red his face is. "Aww, you are so cute!" she says. "I can't wait to go out with you tomorrow afternoon, baby." Then she walks away from the table, swaying her heart shaped ass. Looking back over her shoulder, she says "Stare all you want now, baby. It will be the last thing you see tomorrow before I sit on your face."

Sarah giggles at this and Tom blushes even more than before. He gets up and adjusts his pants in an attempt to hide his erection. The gangly boy heads off to his class, not sure if he dreamed up the whole thing or not. It's so surreal! God she really is something different isn't she? Nothing like other girls he'd had conversations with before. Not that he talked to many girls.

When he is settled on his seat in his afternoon class, he feels his phone go beeping. He frowns and looks at it. His face goes red again as he sees the image he received. Leslie sent him a photo of her famous ass, completely naked. It is so thick and round that he nearly cums in his pants just looking at it. He never felt so horny in his life.

'Jerk off to this picture and cum on it tonight' she texts him. 'Do it on a second screen and send me proof of the aftermath. I want to go to sleep after seeing your cum on my huge ass.'

The rest of the class, he tries to focus on what the teacher is saying, trying to ignore the throbbing boner. He could not wait for class to be over to go home and rub one out to the image Leslie just sent him. God she is so fucking sexy!

As soon as he is back home, he rushes up to his room where he locks the door. Then he removes his pants and looks at her picture. He takes a picture of that on his iPad and jerks off to it. The boy only has to beat his meat for two or three minutes before cumming on the picture. Then he sends a photo of the mess he made to her and waits for her reply.

"Good job! I knew you would follow my orders," she tells him when she calls him later. "I will pick you up at around this time tomorrow. You can go home first and put your stuff away before we go on our date. Sounds good to you?" He tells her yes and they talk for a few more minutes before she hangs up. The boy heads into the living room where he finds his uncle back from a jog.

"What are you smiling about?" Fritz asks his nephew curiously. "Not that I'm not glad to see you happy. You just look so exuberant."

"I got a date tomorrow, Uncle Fritz," Tom tells his uncle excitedly. Fritz is shocked but then breaks into a wide grin. He then hugs the boy and pats him on the back, before coughing. This immediately makes Tom frown. His uncle is dealing with cancer right now and the doctor said he is handling it well, but then again, anything can happen. "Let me cook you dinner while you clean up," he says. "Take a shower and I'll whip something up."

Fritz nods. "Listen," he says, coughing again. "When you're on that date, you need to be a gentleman. Listen to her talk and pay attention, even if you feel bored. Got it? I know it's your first date which is why you have to focus on it."

Tom nods and his uncle walks to the bathroom to get a shower.

........

Leslie is feeling kind of nervous. Even though she is the hottest girl in school, the tall brunette rarely went on dates before. It's not because of lack of choice or anything. All of the boys want her a lot, except for the gays. No, it's because they all wanted her for her body and also her money. She is, after all, a filthy rich heiress who has even more money than the second, third, fourth and fifth richest students combined.

Tom is different though. He has never looked at her in a creepy way. Yeah, he glances at her boobs and ass whenever he walks past her in the corridor, but he only glanced at them briefly before looking away. He has also always been polite and respectful. Yes, she loves how other boys masturbate to her but the things they say to her are always too rude, too arrogant, too cocky for her liking. Tom doesn't behave that way though.

He is a soft-spoken, well mannered guy who makes her feel warm inside as she looks at him. When she sat with him at the table, she felt safe. He made her feel at ease. So comfortable she actually teased him in person, when before this, she only teased guys on social media, and never a specific guy either. Just the guys on her profile page in general. In short, he made her do something that she never did before.

When she arrives, the girl is a bit upset. Her date lives in a shabby house that is run down. This annoys her since she is rich and wants her date to be rich too. But then she thinks of how cute he is and decides to overlook this in favor of going out and being with him. Leslie then knocks on the door and waits.

A few minutes later, Fritz opens the door. He looks at the beautiful young woman in front of him and asks "Are you Leslie?" Leslie immediately nods. He smiles kindly at the teenage girl. "I'm Fritz Long, Tom's uncle. Tom is getting ready in his room right now. He's very excited. It's my nephew's first date ever."

Leslie asks "Why is he living with you, Mr Long?"

"You can call me Fritz, and he is living with me because my brother is dead, and my sister in law is in prison," Fritz explains, taking off his glasses, wiping it with his green shirt.

"I'm so sorry Mr Long, I mean Fritz," she says. "What happened to them?"

"Well, my brother went to Afghanistan with me but he came back in a casket. I didn't come back unscathed myself but here I am now. His wife, um, well, she embezzled some money after that to try to make ends meet. So now she is in prison," Fritz says. His eyes grow misty as he thinks of the day he and his brother were shot in an ambush. He survived and came back home with a Purple Heart, but had to tell their mom about how his brother died in his arms, a whole continent away from home.

Leslie waits with the middle aged man until Tom emerges from inside the tiny house. He smiles shyly at her and walks towards the girl, who bends down a bit to peck him on the lips. Tom blushes and his uncle chuckle. "You can come home late today," Fritz says to his young nephew. "Enjoy yourself, kiddo. Have a good time."

The boy waves bye to his uncle and heads out before pausing. His jaw drops open as he takes in Leslie's car. Leslie smiles proudly, leaning on the BMW her dad bought her for her 18th birthday. She says "I know, I'm really loaded," before getting in behind the steering wheel. Tom then gets in right after her and she starts driving.

Leslie gives him a smirk as they stop at a red light intersection. She loves how he is staring at her muscular thigh. The girl is very proud of her muscular thighs and subtly flexes them, making his Adam's apple bob up and down as he gulps. Then she looks straight into his eyes so he knows that she caught him checking her out. She chuckles at how embarrassed he is, loving that he can still get so easily flustered around her, what with her teasing ways.

At the restaurant, they sit down together, with her telling him what the best dish to order is. He takes her advice and they sit and talk while waiting for the food to arrive.

"So tell me more about yourself," she says. His eyes go wide with panic. Tom knew he would end up having to tell her about himself at some point but didn't expect it on the first date. He feels his tongue twisting about like his stomach. Why does he have to be so nervous? This is his first date and he should be enjoying! Not freaking out just because of a simple question like this. "Why are you still single? You're really cute and should have girls asking you out left and right."

"You are much cuter than me and you're single," he mutters and she grins, clearly happy that he called him cute. "I guess it's my self-esteem issue. I worry about being rejected a lot so whenever I approach someone, I feel my throat squeezing in and I can't breathe. The next thing I know I'm running in the opposite direction." He shrugs as he thinks back to all those times he panicked right when he thought he'd finally stop being alone.

"But how did you manage to stand up for me in the library though?" she questions Tom. Leslie's eyebrows knot together curiously. "That took a great deal of courage. If you have that sort of courage asking a girl out shouldn't be THAT difficult, right? It couldn't be."

"I stood up for you because it's the right thing to do. My dad was the one who told me to always do the right thing, no matter how hard it is." He sighs, growing slightly misty eyed as he thinks of his late father. "Sorry,"the boy apologises to Leslie. "It's just that whenever I think of him, I get all... Sorry, I didn't tell you what happened. He, well, let's just say he.."

"Died," Leslie finishes for him. He stares at her. "I'm so sorry, Tom. Your uncle told me about it. He also told me your mom is in prison for embezzlement."

"Embezzlement," Tom scoffs dryly, not looking at all amused. "I'm sorry, but that's just what he tells people, because it's already tragic enough that my dad is dead. The truth is she's in prison for murder." Leslie gasps in shock. "I'm telling you this now because I trust you. I don't trust other people. You're the only person at school who has been nice to me, other than the teachers. My mom murdered someone and is now serving life in prison in maximum security."

"Oh my god!" she gasps. "I'm so, so sorry, Tom. I had no idea it's this bad." She reaches over to stroke the back of his hands gently and he smiles slightly.

"No, I'm sorry, Leslie," he tells her in a low voice. "This is our first date. I really shouldn't have brought up such a sad subject." He looks sincerely apologetic and she caresses his cheek, giving him a warm smile. He turns bright red from the contact, still not used to Leslie's very flirtatious nature.

"Don't worry about it," she replies. "It is a part of us learning about each other alright? You have no reason to feel any shame for opening up to me. I am your date, after all. In fact, why don't we make us official and exclusive? Will you be my boyfriend please?"

"Yes! Of course! I like you a lot Leslie. I just can't believe you would like a guy like me," Tom says shyly. He is feeling captivated by her eyes and does not know how to handle this, other than to say yes. Because he does like her and he wants this to go really well. And that means saying yes and giving her what she wants. It's also what he wants, not just because it will make him happy but because he wants them to be exclusive too. It is just the only way to go for the young boy.

"Good. I'm so happy you said that," she tells him and their food arrives soon. The two of them start eating and Tom finds himself thinking about how lucky he is to be here on a date with a great girl like Leslie, who likes him enough to ask him to be her boyfriend. He smiles as he eats, happier by far than he's ever been before. God he feels like he could lift the weight of the world right now! Leslie looks at him and smiles too as she sees how happy Tom is.

On the drive back to his place, she rubs his crotch and unzips his pants. The boy blushes madly. He couldn't believe what she is doing when they arrive at a red light intersection. There she pulls his dick out of his pants and strokes him gently, jacking him off. He moans and she grins, delighted by his reaction. It is her first time touching a cock and she is doing very well so far.

Her hand caresses him and tugs his rod, pumping his meat rhythmically. His moans get louder and he finally ends up cumming in her hand, just like she wants. She then places her fingers in her mouth, tasting his semen. "This is the perfect dessert," Leslie remarks. Tom now blushes even more than he did back when she asked him to be her boyfriend. "I'm serious. Your cum is so tasty, baby."

"Thanks," he replies. She soon takes him straight back to his uncle's house. He gives her a goodnight kiss and then gets inside. After closing the door, he leans right back against it, sighing in happiness. He is so glad he decided to take a risk and said yes to her when she asked him out yesterday. If he didn't, then he wouldn't be in a relationship right now. He would've remained alone like he was before this.

Suddenly he could hear the sound of his uncle approaching. "So how was it? Did you two become exclusive?" Fritz asks his teenage nephew. He looks very interested, having grown protective of Tom after the boy's father died. He was already protective before that, of course, but now that Tom's mom is in prison, Fritz is all he has left. Tom nods and Fritz smiles approvingly. "Good. If your dad is here right now, he would be proud of you. Settling down early so you could have loads of time to spend with your special someone." Then the middle aged man pours himself some water and coughs violently, his body shivering. He looks really pale and just standing upright requires a lot of effort, exacting a heavy toll on him.