Parole Officer Ch. 01

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He has to fuck his sister’s parole officer to keep her free.
6.1k words
4.13
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Part 1 of the 3 part series

Updated 06/11/2023
Created 05/23/2022
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Alex is in hell right now. The 18 years old high school boy has always been the target of bullying. Ever since he moved here, his timid personality has always made him a feasible victim. But it is the cheerleaders who are the cruelest to him. They always mock him for being so weak and insult his appearance. Their actions have been getting worse and worse over the past weeks. Right now it is just about as horrible as it can get. He is in the changing room with them where they are doing the single most humiliating thing to him anyone can ever do, and he can not escape.

They have tied him up and placed him on the floor, and are now taking turns pissing in his mouth. Being used as a toilet slave is the most degrading thing that he can imagine. It nearly breaks Alex to have to lie there with his mouth hanging open as they pee in it. Feeling their sour piss hit the back of his throat makes him crawl away and hide but he knows he can't do that. They'll stop him and then beat him senseless. He has no choice but to let them do this to him for as long as they want, hooting that one day they will eventually be bored and decide to let him go.

"Look at this beta wimp drinking all our pee," snickers Audrey, a stunning black haired girl who is taller than him at six feet. Her fit, toned legs are spread apart as she directs a geyser of urine down into Alex's waiting mouth. The girl actually has crush on him but she has a serious dilemma about asking him out, being afraid her friends would disapprove. She therefore ended up as a part of the group that's pissing in his mouth since it is a way for her to be very close to him without anyone suspecting about her true feelings for Alex.

Her friend Heather also laughs as she too sprays the inside of his mouth with warm pee. Both girls are pissing in his mouth at the same time before they step back and let two other girls take their place on either side of his head. Heather watches with a wicked gleam in her eyes as her friends urinate in the pathetic dork's mouth, which is already on fire after being filled with hot piss several times in a row. "You are right. He looks like such a fucking loser right now. That's what he is. Just a toy for us to play with."

Now it is Amber who is laughing as she empties her bladder into Alex's mouth. She sneers at him. "You like the taste of our pee, don't you? I can see the tent in your pants." It is true. For some reason his cock is so hard right now as the hot girls all take turns using him as a toilet. He is pulsating as she and her friend pee into his mouth and force him to swallow all of it. "Go on. I want you to swallow all of my piss and thank me for it. Thank me for feeding you with my delicious pee."

Alex couldn't believe she is taking this so far. None of them ever went as far as making him thank her for treating him so horribly be for. It is shocking cruel, even by their standard. She glares at him when he refuses to speak after she stopped pissing. Finally, he puts on a fake smile. He then says "Thank you for letting me drink your piss, Amber." She gives him a satisfied sneer and resumes peeing all over his face as he lies there beneath her. Finally she and her friend are done pissing and they untie both of his wrists, releasing the tormented boy from his bondage.

He goes over to the sink but Heather says "No, you are not allowed to wash your face. We want you to go out with our piss all over your face. That's why we marked you with our scent in the first place." Alex is horrified by this but he does not want to be beaten up and therefore gives in to her demand. The ashamed boy sobs, watching as the beautiful teens put their cheerleading skirt back on to match their tops, and then drag him outside the locker room with him between them. Most other boys would love to be with them but he knows how cruel they can be, having just experienced it first hand himself.

Alex feels humiliation as drops of tears roll down his cheeks. He could hear the other cheerleaders outside laughing at him, pointing at his soiled face. "Look at that whore. I can't believe he let them pee all over his face and inside his mouth," McKenzie teases, giggling with her friends as they high-five Amber and and Audrey. Audrey snickers, eyeing the boy in question out of the corner of her eye. She thought about telling the other girls to leave him alone and that she will torture him herself, but then got scared that they might figure out that she has feelings for him.

Alex cries as the teen cheerleaders all slut shame him for letting the girls use him so easily. Some of the boys join in as well, labelling him a whore. He can't believe how his life has turned out to be this way. To be a sex toy for these evil bitches who treat him as below them. It pains him to be seen as inferior as he has always had a low esteem of himself. All he could do right now is to try to be brave, if not for himself then for those who care about him.

His older sister Kathy, who has been imprisoned for embezzlement, is now coming home on parole. Alex knows he has to make himself presentable when he gets home tonight, so that she does not worry about him. He knows how super protective of him she can be and that if she knows he's been defiled by the nasty cheerleaders, she might just kill them. Alex doesn't want that, since as much as he hates the girls who are bullying him, he doesn't want anyone killed. Not for him, and especially not by his sister, who just got out of prison and would be back in again for a much longer period of time if she murders someone now.

On his way home, Alex recalls how this all started. A month ago, the same girls who initially only insulted him decided that getting physical would degrade him even more. They forced him to eat their pussies at first, using only the womanly juices to soil his face. After that they progressed to using piss, realising that it will humiliate him even more than they already did. In hindsight, if he acted like some depraved psycho who enjoyed what they were doing, it might have stopped them from doing it again.

Unfortunately he wasn't so bright and here he is, still getting bullied by these sickos. As he gets back inside his house, he is pleased to see that his parents aren't back yet. He rushes to get his clothes in the laundry and washes his face as much as he can, in order to get rid of all traces of piss that the cheerleaders poured all over him. Fortunately, their piss isn't really a sticky thing and he manages to clean himself up rather well. Then he puts on some new clothes.

After that he goes into his bedroom, sitting by the window and reading his history textbook. It helps distract him from his woes as he studies, all while thinking about Kathy. It has been so long since he last saw her, after she got arrested for all those financial crimes. She's about ten years older than him and has helped his mom raise him after his dad left them for his secretary. Now he is going to see Kathy again, after the past few years of not seeing her once. She didn't want him to visit her in prison and told his mother not to take him there.

Suddenly, she enters through the front door. His sister was really hot before going behind bars. She is still good-looking, but has aged far beyond her 28 years. Alex pretends not to notice how haggard she is and rushes over to hug her tightly. Her hair is unkempt as she hugs him back, shedding silent tears of joy as she is reunited with her brother. "Oh, I missed you so much!" Alex exclaims, leaning back after the two have been hugging for sometime now. He really did miss her a lot and has been desperately waiting for the day she can come home.

"I missed you too, Alex," Kathy sniffles. She looks at her cute brother proudly. Although Alex's cuteness can also bring trouble, as she had to keep one of her friends from molesting him back before she was arrested. He has blossomed into a very endearing, sweet young man who does not know how attractive he is. "I promise I will never, ever do anything so stupid again. I'm never going back to that place. I give you my word." She kisses him gently on his forehead before enveloping him in her arms once more.

Alex hugs her back for a moment and then extracts himself from her warm embrace. "Good! I don't know if me and mom will be able to handle it if they take you away from us again," the boy says, wiping away his tears. He's already cried twice in one day. "Come on. Let's get you inside. You can go shower in your own bathroom now. It should be nice after years of prison." She laughs lightly, nodding. Both of them head inside the house together, chatting about how life has been behind bars for her, and at school for him.

The teenage boy knows that his overprotective sister would flip if she finds out he has been subjected to golden showers against his will. He decides to obscure that bit, only revealing the parts where he was made fun of for his shitty hairstyle and the like. Still she frowns, almost as if she knows he is hiding something from her. "Are you sure you are telling me everything, Alex? You look like you've got something else on your mind. You know you can tell me everything right?"

This makes him gulp. He considers lying through his teeth but then remembers that Kathy is a human bullshit detector. Lying to her almost never works. Only their dad managed it, hiding his affair with his secretary quite well for a period of over two years. "Well, some of the girls in my year have been pissing all over my face and into my mouth," he says, making her eyes go wide. "They'd drag me into the changing room and drench me in their pee. But nothing harmful! I swear, I'm okay. There's no need for you to worry about it."

He regrets not trying to cook up some elaborate lie. At least she doesn't know any names. That should prevent Kathy from going on a blood streak of revenge that will land her back in prison, with a much longer sentence than the one she received before. As it is, she is now growling angrily. He places a hand on her arm, trying desperately to calm her down. "I'm going to kill them," she snarls, making him rapidly pale. "I'm going to slit their throats. My cellmate showed me how. She killed her cheating husband when he tried to take their son away from her."

"No, no, no!" Alex quickly says, hands on his sister's shoulders. "Kathy, you just got out. Please don't do anything that will land you back behind bars. Don't do it to me and don't do it to mom. I'd rather have them roam free than have you imprisoned again. If you get locked for a second time, I'll start cutting myself," he threatens her. This works and she sighs, promising him that she won't use violence, making Alex smile. "Good. Now go take a shower. I'll cook you something."

......

As a parolee, Kathy has to fulfill some conditions in order to stay on the outside. One of those is trying to find a job. Unfortunately, she hasn't always been the most responsible of adults. That's what landed her in prison in the first place. Luckily enough, Alex is more responsible and has secured a few job interviews for her, writing it all down in bold letters on the calendar. He even used flattery and flirtation with one of the people he talked to in order to get his sister an appointment, something which he never did before. Desperate times, desperate measures, Alex tells himself as he eats his cereal.

His sister is putting on her best clothes as she waits for her parole officer Miranda Sheffield to arrive. She thanked him profusely last night when he told her he already arranged some job interviews for her, saying that she will do her best to avoid screwing up. He nodded and then went to bed right after. Now he is waiting for Kathy to get herself ready. She is going to one of the interviews right after Miranda checks in on her. It is supposed to be just a routine check in and nothing special. Neither of them are aware that it will be much different from what they had expected.

Hearing the sound of knocking, Alex goes to peek through the peephole and opens the door. He is caught off guard by the extremely beautiful 30 years old woman who is standing on the other side. She has a gorgeous face framed by long, curly blonde hair that reaches down to the middle of her back. Her breasts are ample, high and round. The white T-shirt she is wearing clings tight to her athletic yet curvaceous frame. Miranda's short shorts reveal half of her muscular thighs. This older woman clearly works out often and is proud of her fit figure, judging by her choice of attire. She clears her throat, giving him a smirk.

Alex snaps out of his reverie. Both of his cheeks are bright red, a visible sign of embarrassment. He stutters for a few seconds, not knowing what he should say to her. Finally he manages to say "I'm so sorry. I didn't mean to stare." She giggles slightly, making him turn even redder, more embarrassed than he was before. At least he's amusing her with his shyness. That has got to mean something, right? Better than for her to be bored. "My name is Alex, by the way. Nice to meet you." He offers a nervous handshake tentatively.

Miranda eyes him hungrily, making the boy go red. He could sort of guess that the older woman's thoughts are sexual, given how her eyes have drifted down to his crotch. The parole officer licks her lips. "It's okay, cutie. I am kind of undressing you with my eyes right now, so we're even," she says teasingly. Her words make him stiffen and she knows this too, looking directly at the growing tent in his trousers. "You know, I feel thirsty right now. Do you maybe have something for me to drink, Alex?"she asks with a mischievous glint in her perfect blue eyes.

He doesn't catch the meaning of her words, being too naive for that, despite having engaged in such lewd acts as serving as a toilet slave for the horrible girls at his school. So the innocent boy says "Let me go get you some coffee. Do you want milk to go with it?" This gives Miranda the opportunity to say a thing that is explicitly dirty to him and Alex does not know it yet, as he goes into the kitchen to get her a cup of coffee and look for some milk to add to it. "Just give me a few moments please. I'll be right there," Alex says to the sexy older woman.

Miranda gives him an impish smirk in response, as she forms her reply in her head. Yes, this would be perfect. She wants to see how Alex react when she says what she is about to say to him. "I think I want something else other than milk," she says flirtatiously, running her hand through her golden tresses in a very seductive way. "You can jerk off and cum in my coffee. Add your semen to it. I bet it would taste so delicious with your warm cum instead of milk." Her face now has a massive grin on it.

Alex gasps in shock at the dirty request. He should not have been this stunned after several girls in his year have done incredibly perverted things to him. Yes, he might be a virgin in the traditional sense of the word, but he is far from a pure boy. Still, to mix his semen in her coffee? "I'm, um, not sure that's how you are supposed to make coffee?" he says in a questioning tone, uncertain over how to proceed with this. He used to think he could handle anything after being forced to drink the cheerleader's piss but this seems to be taking it to a whole new level.

He is also ashamed to be getting harder so quickly. Before he was only partially erect. Now his prick is harder than it's ever been. Suddenly, Miranda starts to laugh, confusing the boy as he watches her in perplexity. "Oh my god! I'm so sorry," she wheezes out. "I'm not going to force you to feed me your cum today Alex. But I will on our fourth or fifth date. And by the sixth, I'll definitely be drinking it straight from the source." She is now walking towards him, one of her hands cupping Alex's balls gently.

This makes him feel his cheeks burn as he slowly backs away. She leans in to him, sniffing his hair. Her nose on his skull makes him feel shivers running up and down his spine. "Wait just a minute, Miranda. My sister would be finished any second. She wouldn't be happy if she sees us like this," the boy urgently murmurs, knowing how livid Kathy would be. She freaks out enough when a girl his age flirts with him. If she sees a 30 years old woman groping him like this, Kathy would lose her shit.

And it is at that moment that his dear big sister emerges from her room. She immediately sees Miranda with her hands between Alex's legs. Kathy sees red. The only reason she doesn't attack is that Miranda is her parole officer. So she just silently fumes, before putting on a fake smile. "Hi, Miranda! Good to see you," she says, walking over to give a firm handshake, squeezing Miranda's hand hard. Miranda's eyes narrow and she smiles coldly, before squeezing hers back even harder. Kathy winces. She never met a woman stronger than her before, having played multiple sports in college.

Miranda squeezes Kathy's hand really hard for a few seconds then releases it with a flippant attitude. "Sure!" she says to her in a friendly voice, as if they weren't squaring off against each other mere seconds earlier. "You are going to a job interview today, aren't you? You told me that your brother here got it for you. He is a wonderful boy." Alex now blushes again from the compliment as his sister tries to conceal how annoyed she is. "Does he have a girlfriend, by any chance?" She is subtly asserting her control, speaking about him in his presence, instead of to him.

Kathy shakes her head slowly, feeling herself boil with rage. She can tell that this woman thinks her teenage brother is cute. It has happened before with a couple of her friends. "He is still single and I am going to a job interview in a couple of hours," she tells Miranda in a clipped voice. Kathy's face makes her strong disapproval plain. She doesn't want a woman who is more than ten years older than her 18 years old little brother to start hitting on him. She only told the truth that he is single since she knows he won't be able to lie if Miranda ask him after. Otherwise she would have lied that he has a girlfriend, in the hope of that deterring Miranda.

The two converse for a few minutes as Alex sneaks a few glances at Miranda. She knows what he is doing and gives him a smirk, making his cheeks flush again after he managed to make the color go down. It is embarrassing how easily flustered he is. All she has to do is give him a flirtatious smile and he is scarlet red across his face and down to his neck. Sometimes he wishes he'd be able to hide his feelings much better. But all he could do is hope to be able to hide his emotions as he gains more experience in the field.

Once Miranda's left, Kathy drops her act and lets Alex know how angry she is right now. She is glaring at the door as her fists clench and unclench. Alex now retreats, backing away slowly, seeing the sign of a storm brewing underneath her skin. "Why are you like that?" the boy asks her cautiously. "Look, I know that she is a little bit older than I am, but age is just a number, right?" Alex knows that she is 30 since Kathy told him about her before, but he truly does not see anything wrong with the gap.

Kathy's eyes nearly boggle out of their sockets as she stares at her brother, as if he's grown a third arm out of his forehead. "Just a little bit older? Alex, this woman is more than a decade your senior! That's not a small age gap when you are only a teenager. Very far from it, in fact." She starts pacing the room angrily, muttering to herself "I swear, if she isn't my parole officer I would be knocking her pearly teeth out now. How could she perve on a kid like that? This is just plain wrong!"

Alex gets up and walks over to her. He grabs her shoulders gently but looks her firmly in the eyes. His eyes tell her how much he has grown in her absence and she is startled by how much of an adult her baby brother is now. "Listen to me, Kathy. I love you and know that you are only trying to protect me, but I am 18 now. I am an adult now and I know what is best for me, so please let me make my own decisions. I don't want to fight you Kathy, especially so soon after you just got to leave prison."

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