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Chapter 6
by Control Freak
Will you wait for Caitlin to arrive, or find someone else to inspect?
Might as well wait for Caitlin at this point
It doesn't take very long for you to decide that waiting for Caitlin to arrive would be more than worth it. After all, you've already fucked one of your sisters, so you might as well go all in and screw the other too, right? You finish up your pancakes, then excuse yourself from the table and head to your room. You take the remaining time you have to get dressed and clean up your room a bit in preparation. You debate also taking a shower, but given what you have planned, it would probably be a waste of time at this point. And it's a good thing you didn't, because just as you were finishing making your room 'not-a-disaster-area', you hear someone knocking on the front door.
You come downstairs in time to see your mom opening the door to let Caitlin in. Your older sister has a lot in common with Dana, including the same golden blonde hair and pale skin. But whereas Dana is short and slim, to the point of looking younger than she was, Caitlin was the opposite: tall, curvy, and knowing exactly how sexy she was and how to flaunt it. You've fantasized about her countless times growing up, and now you'll finally get a chance to live those fantasies out.
When Caitlin sees you coming down to meet her, she smiles and says, "Hey bro, congrats on the new job."
"Thanks," you say, reaching around the laundry basket under her right arm to embrace her. Knowing that you can get away with it, you do so by wrapping your left arm around her back, your right hand down the back of her jeans to grope her ass, and pulling her in to kiss your sister on her glossy pink lips.
Caitlin reacts with shock at first, but it isn't long before she starts kissing back, albeit somewhat hesitantly. She continues to do so until you pull back, at which point she gives you a half-hearted smile and says, "Not even going to say a whole sentence to me before giving me a surprise inspection, huh?"
"Your brother's taking his new job very seriously," your mom says to her, "He was inspecting Dana less than five minutes after getting the position. Although he was way more thorough with her..."
"Oh, that was just Caitlin's chance to make a good first impression," you reply with a smirk as you let go of your older sister, "I'm going to be examining her more closely in a bit, but I wanted to give her a chance to at least start her laundry first."
"Well that's pretty generous of you," Caitlin says with a more genuine smile.
Before anything else can be said, Dana runs up and excitedly squeals, "Caitlin! You've got to check out my evaluation sheet, I scored really really well!"
You see both your mom and Caitlin visibly shudder at the sound of Dana's high-pitched tone of voice. Caitlin blushes as she composes herself and mutters, "Damn sis, you must've scored pretty high with a voice like that..."
"Yeah, a 9!" Dana replies with a grin, "It's my best feature, but I scored high overall! You've got to see!"
"Maybe later," you tell your younger sister, "Caitlin's about to have her inspection."
"Yeah, wouldn't want to put that off," Caitlin adds. You can't help but notice that your normally confident older sister actually looks slightly intimidated.
"Oh okay," Dana says, "But right after you're done, we should compare our scores!"
"Sounds fun," your sister says with a nervous smile.
"Well, we should probably get moving then!" you say eagerly, "Caitlin, put your clothes in the wash, including what you're wearing now since you won't need them, then meet me in my room. I'll be conducting your inspection in there."
And away from an audience, you think to yourself as you go to collect your clipboard from where you left it in the kitchen. As amusing as it was to have your mother act as cheerleader for Dana, you would rather not have any distractions while you 'inspected' Caitlin. Her body was something that should truly be savored.
A few minutes later, a nude Caitlin comes into your room and shuts the door behind her. You can't help but take a moment to admire her toned, sexy body. Her job as a fitness instructor has had an obvious role in keeping her looking fantastic, though the D-Cups on her chest certainly helped with that as well. Seeing that she was struggling to keep herself from covering herself up, you ask, "Nervous?"
"A little," she admits with a frown, then asks, "So Dana really got a 9 in Vocalization?"
"Yeah, but she didn't mention that she didn't score quite as well in other areas," you say as you take your sister's hand and lead her to the center of the room. Once she is in place, you let go and start running your hands over her body, beginning at her shoulders and moving to her taut belly. It isn't very long after that before you are squeezing her soft tits in your hands, "For example, I have a pretty good idea of at least one area you will be scoring higher than her in."
"Mmmmm... yeah, my boobs are pretty great, huh?" Caitlin says in a breathy moan.
"Yeah," you agree, before asking her, "Is this turning you on?"
"A little bit," she admits with a blush, "But probably not as much as it's turning you on."
Feeling the raging erection threatening to burst out of your pants, you're inclined to agree with her. Still...
"I know one way to find out," you say to her with a smirk, before dropping your right hand down to her crotch. Your hand brushed against her fuzz briefly before coming into contact with her slit. You rub your fingers against her moist pussy, causing her to shudder in your grasp.
"Well, you do seem to be getting wet down there," you say, bringing your hand back up to show Caitlin the juices now coating it, "See?"
Caitlin goes red with embarrassment and says, "Ohmigod, I'm so sorry! I shouldn't be getting this turned on from being touched by my brother, even if he is the Female Body Inspector."
"It's quite alright," you reassure her with a chuckle, "Good lubrication is one of the things I need to check a vagina for. If anything, I take it as a compliment of my own skills."
"Oh," she says, looking down at the floor nervously, "So, um... is it, uh... 'lubricating' well enough?"
"You tell me," you say, holding your hand up to her mouth, "Go ahead and clean it off for me."
Caitlin looks at the hand hesitantly, then at you, then back at the hand. She then slowly takes your fingers into her mouth and sucks her own cum off of them. The feeling of her tongue lashing against your fingers feels fantastic, though you only get to enjoy it for a little bit before she pulls off and wipes her mouth.
"So?" you ask, wiping her saliva off on her shoulder.
"It tastes... well, like pussy," she says, "Not really sure what else to say."
You frown at this, which caused Caitlin's eyes to widen. She must think that there was something wrong with the answer she gave you. Really, you just wished she had more to say, but you might as well roll with it at this point. It might motivate her to do more to please you.
"I see," you say, trying your best to sound like you were a health inspector in a not-so-clean kitchen, "Well, let's move on to the next part of the inspection."
Caitlin watches anxiously as you pull down your pants and boxers, freeing your rock-hard cock from confinement. You gesture to it and tell her, "I want you to suck my dick. Do your best to get it nice and wet for me, okay?"
Your sister nods, then drops to her knees in front of you. She takes a moment to psych herself up, then takes your dick into her mouth and starts sucking. Her mouth feels like heaven on your aching cock, especially her tongue running along the bottom of your shaft. You let out a groan of your own and put your hands on her shoulders, holding Caitlin in place as her head continues to bob up and down on your cock. Caitlin takes this as a sign she is doing a good job, and starts getting into it more.
It isn't very long until you feel like you're about ready to let loose. You are tempted to let Caitlin finish you off right there, but you have something better in mind. You somewhat reluctantly tap her on the shoulder and tell her, "Okay, stop. Let's see how you did."
Caitlin runs her soft pink lips down your shaft one last time before pulling off, leaving a small string of drool momentarily connecting her mouth to the head of your penis. Her spit now generously coats your cock, which is exactly what you were aiming for. Now for phase 2 of your plan.
"Looks good," you say to her, causing her to smile, "Alright, now I want you to get on the bed and present your backside to me. Make it look like you want me to fuck you right now."
Caitlin nods, then gets up and hops onto your bed. She lays face down on top of it and raises her juicy ass into the air in order to show you her still-wet pussy. She then looks back towards you and wiggles her ass enticingly, saying, "Please fuck me, John... I need your cock so bad. Don't make me wait for it any longer. Let me show you how good my pussy feels."
Wow, guess she really was trying to impress you now. If you could, you'd definitely give her an 'A' for effort.
"Well, if you insist," you say, climbing onto the bed behind her. You take a moment to take in the sight of your older sister, naked on your bed and begging you to fuck her just like you dreamed. It was almost breathtaking. Not wanting to wait any longer, you spread her cheeks and line up your dick with the intended hole, "But I'm not going to be fucking your pussy."
"Wait, what are you-" Caitlin starts to say, before letting out a scream as you thrust your wet dick into her asshole. She's pretty tight, but thankfully she did a good enough job lubing you up with her mouth that you're able to slide in with a bit of effort. Your sister looks shocked at this sudden turn of events, and in at least a little bit of pain, but the closest she comes to protesting is telling you, "But I've... I've never done anal before!"
"Which is why I need to see if you're any good," you tell her, "Besides, with an ass like this, how could I resist sticking my dick in there? Just try not to fight it and you should be fine."
You start thrusting in and out of her asshole, going slow in order to avoid hurting either of you too much due to the tight fit it had around your cock. Caitlin shuts her eyes and lets out another moan, a mixture of pain and arousal evident in her voice. You weren't sure exactly how much of it was the anal and how much of it was left over from your earlier playing, but you didn't really care at the moment. As you keep fucking her ass though, you notice that she has reached her right hand between her legs and has started playing with herself.
"Naughty girl," you say to her, before giving her a sharp swat on the ass that causes her to let out a yelp, "You're not going to cum before me, understood?"
"Y-Yeah, okay," she says, letting her hand drop.
You give her another hard spank, "I didn't tell you to stop."
Caitlin goes back to masturbating, the side of her face pressed hard into your mattress. You continue to thrust your cock into her ass, occasionally giving her another spank on her voluptuous backside. Eventually, you start speeding up, causing your sister's breathing to grow ragged as she speeds up as well. Before long, you unload your cum into her bowels, and not long afterwords, Caitlin lets out a scream and bucks on your cock. Satisfied, you pull out of her ass and collapse onto the bed next to her.
"That was..." you start to say as you catch your breath, before putting an arm around her head and pulling her in for one more kiss. She returns it here far more eagerly than she did downstairs.
Pulling away, she smiles and says, "Well that's a good sign."
"Maybe it is," you tease, "Or maybe I just wanted to check how well you kiss one last time before I finish."
Caitlin laughs, but you an detect a hint of anxiousness in her voice, "I guess I'll know in a minute, huh?"
"Yeah," you say, grabbing your clipboard off of your bedside table, "Just... give me a second to recover and I'll give you your score."
"Sounds good to me," Caitlin said, "I'm not going anywhere like this. Besides, after what my ass just went through, I'll probably need a minute too."
She looks back and rubs her butt cheeks tenderly while you look over the sheet, debating what exactly you want to do. Caitlin was your sister after all, so you felt almost obligated to give her an honest score. However, the temptation to fool around with the numbers was growing on you, and you did already mess up a bit with Dana's score despite your best effort not to. Perhaps it wouldn't hurt to experiment a bit with Caitlin as well, in order to get a feel for how this scoring system worked. After all, you could always change it later with another 'inspection', which is something you were far from against doing. Then again, this was your sister you were talking about. She was only the second of many women you will be having sex with today. Experimentation might be better suited for someone you wouldn't feel too guilty about screwing around with.
Either way, it wasn't like you were in any rush. You had at least until the wash cycle on Caitlin's laundry was done, or she starts bugging you about it, before you absolutely had to make a decision.
How do you score Caitlin?
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Sexual Privilege
Freeuse for One
These branching stories are going to have 3 very simple premises: 1) You exist in a world where your character AND ONLY your character gets to have sex with whatever group or groups of people you choose wherever and whenever he or she desires. 2) The circumstances under which he or she can have sex with that group can be specified generally or specifically. 3) The response of the people you have sex with and/or the general public can be chosen.
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Updated on Jul 4, 2025
by Cross C
Created on Aug 31, 2017
by SanctifiedVillified
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With every decision at the end of a chapter your score changes. Here are your current variables.
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