Parole Officer

The next day

Alex has never felt more nervous before in his entire life. He does like Miranda so that makes what he is about to do a lot easier. But still, he'd rather have lunch with her and go to some romantic places together first, before giving her his virginity. He wants his first time to be a special experience that he can cherish, not one that is coerced with a threat to his sister's freedom. Yet the parole officer's dominance over him also makes him hard. He looks down at his pants to see that his cock is already straining against it. Shame fills him as he realises how desperate for intimacy he is, to have his dick throbbing for a woman who is treating him like a toy.

She is sitting next to him on the bed right now. Her lower body is bare, revealing a very hairy pussy. She wraps one arm around his shoulders and then leans in to kiss the teen on the lips. He moans and she bites his lower lip. Surprised, Alex gasps and she takes this opportunity to slip her tongue inside his mouth. French-kissing the innocent boy, Miranda inhales him, holding him tight against her stronger body before pushing him down on his back. Miranda pins his wrists above his head as she continues their passionate make out session, not letting him rest.

The older woman slides down, taking his T-shirt and pants off, letting her blonde hair touch his stomach. She slides his boxers off, revealing the five inches erection. With a smirk, Miranda begins to stroke him, caressing the engorged tool. Her hand focuses on the swollen knob, paying attention to the most sensitive part of his body. "For someone who claimed he didn't want this yet, you got extremely hard, baby," she teases him with a lecherous grin. Her eyes glow with unconcealed lust as she jerks him off with one hand, playing with his balls with the other, making him buckle his hips up uncontrollably.

It's all Alex can do not to cum immediately. He has never felt another person's hand on his dick before, other than his own. None of his masturbating session ever felt this good. Miranda grins as she keeps on lewdly stroking his cock. Her fist is flying up and down the pole no and she does something that shocks him. She bends down to kiss the spongy tip before taking the entire rod inside her mouth. "No, stop! Please stop or I'll cum right away!" She ignores this, sucking him off hard. Her head bobs up and down on his lap. Alex's brain melts as he feels the wetness of her mouth engulfing him completely, devouring his prick.

The blonde greedily sucks his cock, sliding her lips up to the tip and then back down to around the base of his pole. Her tongue attacks his bundle of nerves, making him cry out in incredible pleasure. It feels far better than anything he could have ever imagined and he quickly warns her that he is about to release. This makes her suck harder and faster and soon he cums inside her mouth. She withdraws her mouth from around his cock to keep on jerking him off, making him spray her face with the rest of his jizz. He can't stop himself from glazing her and pumps more semen onto her cheek, his ejaculate splattering against her perfect face. Miranda's cheek is soon glazed with his creamy cum and she smiles. Finally he stops cumming, after having already cummed all over Miranda's face for several seconds.

"That was really delicious sweetie," she says, making him blush as she gets up. She then grabs a box of condom. Keeping her eyes on him, she rolls one over his still hard penis. "Now it's time for the main course." Then she slides up on top of him, straddling the boy. Miranda aims the head of his cock at her entrance before dropping her weight. Her tunnel sheathes him and his dick enters her in one movement, completely inside. Alex gasps in shock. Her blowjob felt good but this is even better. It's so wonderful to be defiled by her pussy.

After taking his virginity, Miranda rests for a moment on top of him before she starts moving. Riding Alex slowly at first, her cunt grips him tightly. He moans as her fleshy insides bunch around him, caressing his prick as she slides her pussy up and down. It is amazing how wonderful sex feels. Now he knows why the other guys are so crazy about it. "Ahhh, fuck me please," he finds himself begging her.

She smirks, realising that she has started to break him already. Using her vagina as a vice, she squeezes his cock, making his eyes go wide as the tightness increases. "Beg me for it," Miranda hisses, lifting her cunt up and then slamming back down. "Beg me to use you as a toy. Beg me to fuck you so hard you won't be able to walk straight tomorrow. Beg me to make you my whore." She clenches her pussy around him tightly as her hips violently ram down onto him again and againg.

As he is getting aggressively pounded into the bed, Alex's eyes roll into the back of his head. His mouth hangs open as he can do nothing but lie there and take the fucking like a good slut. She stops for a moment and he immediately begs "Please keep fucking me! I love your pussy so much! Make me your slut Miranda!" His pleading satisfies her and she resumes ravishing him, her cunt sucking his dick really hard now as he gets closer and closer to his orgasm.

She suddenly comes down hard on him and buries his prick all the way inside her as he cries out, cumming really hard. The condom is soon filled up with his cum and she gets up, lying down next to Alex on the bed. "Make me cum too," she orders." Alex dumbly nods, crawling down to kiss her puffy cunt and lick her. He eats her out gently, probing inside her with his tongue before sucking on her clitoris. It doesn't take very long before she too climaxes, squirting all over his face, drenching him with her sticky pussy juices.

Alex passes out after that, exhausted after getting fucked so hard on his first time. "You're mine now. I marked your cock with my pussy juices. You are my lover, bitch and sex slave," she tells him, kissing him tenderly on the cheek. Alex finds himself blushing again. His first time didn't hurt like he feared, even though she got quite rough. It actually felt pretty good. Being so naive when it comes to intercourse, he didn't know that he isn't supposed to feel any pain in the first place, and is relieved that he didn't.

He leans into her arms subconsciously and lets her hold him. It feels so safe in her embrace. Alex almost can't believe she is the same woman who casually blackmailed him into fucking her. Not to mention that she did it so soon after meeting him for the first time. "Okay, Miranda. But you will not take my big sister back to prison, right?" Alex asks just to make sure he didn't give her his body for nothing. "You promised me. Tell me you meant what you said." He starts panicking, thinking she might have used him.

"Of course I'll keep my word, since you kept your promise too," Miranda says, rolling her eyes. "But there's something else that you have to do too. I want one more load of your baby batter on my fucking face, baby. So you better climb up here now and start stroking. Give me another facial." Alex does what she says, sitting below her chest and caressing his warm penis. It is still slick with her lady juices, enough to use as lubrication as he masturbates. "I want to feel it on my lips and chin, sweetie. Make sure to hit my cheek as well, just like you did the last time."

Hearing her tell him to give her a cum facial proves too much to handle and he has his third orgasm of the session. Alex's dick throbs violently and erupts, blasting the waiting blonde's perfect face with jizz. He keeps firing strands of cum onto her face and covers her lovely cheeks with his seed. Soon, her beautiful face is soaked in his semen. Miranda's cheeks have his pearly cum all over them and she smiles. "Look at how weak you are. You are such a pathetic slut, letting me have your cock and cum so easily. You've always been a slutty boy. You just never knew until you met me."

She then gets up from the bed and puts her thong and skirt back on, leaving the semen on her cheeks and lips, deciding not to wash it away. "I won't get your sister into any trouble but you will have to keep doing this for me. You are my cum dispenser now. All you are is my property and I don't care about your feelings. When I tell you to fuck me and cum on my face, you will do it, even if you don't feel like doing it that day. Or else you can say goodbye to Kathy for the next five years." She then kisses him forcefully, making him taste his own cum on her pouty lips.

She watches him get dressed and then slaps him on his ass, before offering to take him home. Alex graciously accepts and she drives him back there. As he is about to leave, she leans over and then kisses him hard, palming his private areas to remind him that she owns his cock and balls now. The flustered boy could barely hide his embarrassment as he disembarks from the car, making the walk of shame back up to his own house. This is something he knows he will have to get used to pretty soon.

When he is inside, his sister confronts him. Alex feels upset that she is looking at him with such judgmental eyes when he only went out to do what he did to protect her. Or did he really? Would he have given in to Miranda anyway even if she didn't threaten him? He knows he likes her a lot. It would only be a matter of time. "Where the hell were you for the last couple of hours? You weren't in school! They called mom and she asked me to try to contact you. But you wouldn't pick up or answer any of my damn texts!"

He sighs, thinking about how maybe he shouldn't have switched off his phone. But if he didn't and she called when he was fucking Miranda, it might piss the blonde bombshell off. So naturally he turned off his phone. "I went to talk to Miranda and beg her not to take you back to prison," Alex tells her, looking Kathy straight in the eyes. "You were drinking, which is a violation of one of you parole conditions. She almost had you taken back in, so please don't do it again. It was your friend Allie, by the way, who reported you. She got upset that I wouldn't sleep with her so she decided to get revenge."

Kathy collapses onto the chair behind her. "God, I had no idea. I'm so sorry," she tells Alex. "And thank you too, for whatever you did to convince her." Alex almost giggles at this, since his strict, overprotective sister is unknowingly thanking him for getting laid by the older woman. "I promise I won't drink again. You have my word, Alex." He nods, satisfied with the promise he got from her, before going straight to his room. This is going to be more difficult than he thought. He knows he would sleep with Miranda again, both because she is blackmailing him into it and because he himself is a slut who can't control the urge anymore.

.....

It's been a week since Alex first fucked his sister's hot parole officer. Losing his cherished virginity to her has been far more pleasant than he expected. It was even better than the boy hoped. She'd called him over to meet her two more times after the first time so she can do it with him again and he obliged. Their second tryst was in a hotel room again and the third was at her own home. On both occasions he lied to Kathy about where he was going, so that she won't have to worry about him. It is just a little white lie, Alex reasons to himself. What was he supposed to do? Tell her he is sleeping with a woman 12 years older than him?

No, he can't do that. His sister would definitely throw a fit about it. There is no way her knowing the truth would end well. He has to keep it secret from her until his relationship with Miranda is on stable ground. That would stop any problem from occurring. He is not sure he will be able to handle it well if she starts yelling at him and calling him a whore, and telling him he should be ashamed of himself. That's what happened when a girl he dated spread a rumor that they had sex. She wasn't upset about the cheerleaders but only since it's clear that he was the victim.

Things get messy with her again when she is supposed to go to a job interview that he got her. She has been too lazy to get one herself when he reminded her so he had to make the calls again, after she failed to turn up for the first ones that he got her. Right now he is reading a textbook in the living room, studying after their mother already left. It helps to keep him calm as he tries to navigate his way through all the stuff that life has thrown his way over the past week.

He looks at her as she checks out her appearance in the mirror, not knowing that she is practicing her 'fuck me' eyes. Kathy secretly intends to get laid by a guy she knows and plans to go there now instead of to the job interview. Of course, she never told her brother this. He asks her "You are going to the job interview this time, right? No more drinking, just like we discussed?" Kathy nods. She isn't lying. No drinking, but not no sex. She just can't be bothered with going to a job interview right now. She needs to get fucked really hard.

Kathy looks at her younger brother and lies through her teeth "Of course, Alex. I told you that I would stop drinking and I meant it." She then hugs him and leaves the house, driving away quickly. He goes back to reading, still feeling a bit of unease. His sense is telling him his sister is going to ditch the interview but he could be wrong. Alex then tells himself to just relax for once and trust his older sister to do the right thing by herself. Alas, he was right to be worried and would soon find out just how.

He switches from reading the textbook to a novel after forty minutes, taking a short break. This way he can better focus and absorb the material when he gets back to studying. It's how Alex has always done it. The dork reads on for a few minutes before getting up to walk around the room to loosen up all his muscles, stretching. He also does this a lot after studying too, to get rid of the cramps from sitting in the same pose for an extended period of time. It helps keep him in good mood, getting rid of frustration.

Suddenly, Alex gets a phone call from a woman who he secured an interview with for Kathy. Frowning, the boy picks up the call, answering it the most polite voice. "Hi, Mrs Smith. How did my big sister do in the interview?" he asks her. He found her number after searching for places that are offering jobs for a person with Kathy's credentials and she was very nice to him from the start when he first contacted her. Now she is sighing though, sounding quite tired as though she just went through a rough spot.

He waits patiently, trying not to panic as thousands of scenarios run through his mind. Did her hands tremble like they do when she goes into withdrawal or did her pupils dilate? No, she was off alcohol during the years in prison. She drank for the only time in several years a week ago, the day after she came back home. There is no way Kathy could've gotten addicted again so soon. "I am sorry I have to say this but your sister didn't even show up for the interview," Mrs Smith informs the disappointed boy in a solemn voice.

Alex nearly drops the phone but he somehow manages to keep his hand steady enough. "Oh, um, okay. So sorry she did that," he mutters nervously. "I will talk to her once I can get ahold of her. I'm sure it must be an emergency of some sort." They talk and then she hangs up, and he stares at the wall, his fingers drumming his legs as he waits for the shit to hit the fan. Once she is back there would definitely be yelling from both sides. He'd yell at her for how she didn't bother going and she'd then yell to justify not going there.

He supposed he can try to refrain from yelling at her but it would be way too difficult. After her little stunt, Alex is far too livid at her. Normally he doesn't interfere in how other people live their lives. But Kathy has refused to rein in her wild side and acted like she used to before going to prison, and in doing so she is violating multiple of her parole conditions already. Drinking alcohol and not trying to find a job. The gentle boy feels the sudden urge to throw a glass across the wall but then calms down, knowing it won't help a thing.

Suddenly, there are a few knocks on the front door. He finds Miranda waiting for him on the other side of the door, a smirk on her beautiful face. She kisses him roughly and shoves her hand down his pants. The older woman wraps it around Alex's rapidly stiffening penis, tugging it gently. "I just found out that your sister didn't go to a job interview that you got for her today," the blonde bombshell whispers. "You have to do something new with me if you don't want her taken back to prison for not trying to get a job."

Alex moans as she jerks his dick, using her hand to stimulate him until he is fully hard. She leans forward, pressing her large breasts against his shoulder, her lips peppering kisses all over his cheek and neck. "Ahhh what do you want me to do?" he asks Miranda shyly and tries to remove her hand from his prick, not wanting to finish in his pants and get it messy. "Please, wait. Stop for a moment." She ignores him for a while and continues to masturbate his tool, before finally releasing his diamond hard cock.

Miranda gives him another scorching kiss, this one right on the lips. He backs away slowly as she enters the room and kicks the door shut behind her, turning around to lock it. As she does so, she bends over at the waist, thrusting her impressive rear end out. Her buttocks press into Alex's groin. Miranda's huge booty crushes his pulsating erection in between the ass cleavage. She looks at him over her shoulder, saying "You are fucking my ass today, baby. Then, when you've already filled up my ass with your cum, you are going to cum on my face again."

The reluctant boy nods, taking her to his bedroom. He's fucked Miranda in hers before but not his. She makes him lie down as she unzips his trousers and takes his boxers off, freeing his excited shaft. "This looks nice and ready for me," she says teasingly, playing with the underside with her thumb, eliciting a loud moan of pleasure from him. She is an extremely experienced woman who knows how to manipulate a guy's penis, and it is showing in how well she is responding to his noises, finding all his most sensitive spots and targeting them.

After giving him a handjob for a few minutes, Miranda gets rid of her booty shorts. She is wearing no underwear. Her hairy vagina is revealed to him like it was several times before. She sits on his face, almost suffocating him with her thick asscheeks. With her derrière firmly planted on Alex's face, she says "Eat my asshole and loosen me up with your tongue before we get your dick in it." He follows her command, burying his tongue inside the older woman's ass and French kissing her nasty asshole. Miranda's ass tastes like heaven to him and he finds this to be very enjoyable, as his tongue delves deep into her backdoor passage.

She sighs as he tongue fucks her ass and then gets up off his face, before getting on all fours. With her ass in the air, Miranda tells him "Use the lube in my purse and fuck my ass now." Alex grabs the bottle of lubricant and then applies a generous amount to his young cock. He gently presses through her tight sphincter, feeling the anal ring expand slightly. It doesn't really have to dilate much to accommodate him. Soon, his entire penis is inside her ass. He could feel her asshole contracting around the base of his dick. The inside of her ass is searing hot, burning him in the best way possible, making him feel pleasure he never experienced before.

"Oh god!" he moans in shock, stunned by how incredibly tight her large ass is. He couldn't believe it as she tells him to start thrusting. Seesawing in and out of the confines, Alex finds himself lost in the wonderful friction between him and the insides of her ass. Miranda twerks, clenching her asshole around him as he drills her, making it an even tighter experience for him as she fits snugly around his rod. Alex starts pounding her ass harder and faster as she plays with her clitoris. "Your ass is perfect."