"Ugh, fine!" You throw your hands up in defeat before sitting on the edge of Bailey's bed. "So, what does this project of your actually entail?" You ask. "It's to examine how chastity influences a male's psyche and gender identity. Every few days I'll give you a small task to do and analyze your response. Easy enough right?" "What kind of small task?" You narrow your eyes, your bullshit meter spiking. "Oh, you know. Just small, easy things. Tonight why don't we start off with just a simple foot rub?" Bailey extends her feet out at you.

"Ew, I'm not touching your feet." You scrunch up your nose. "Did you want to cum tonight or not?" Bailey tilts her head challengingly. Suddenly feeling much more motivated, you cast aside your disgust and grab one of bailey's feet with both hands. "That's what I thought." Bailey smirks down at you, seemingly enjoying herself as you rub her soles in slow, concentric circles with your thumbs. 'You're only doing this so that you can cum, you're only doing this so that you can cum...' You repeat over and over to yourself. "Mmmm... make sure you get in between my toes as well." Bailey instructs, letting out a contented sigh at your ministrations.

After rubbing Bailey's feet for the better part of an hour, she waves for you to stop. "Not bad little bro. A girl could get used to this kind of treatment." Bailey yawns loudly and stretches, looking so relaxed that she could almost fall asleep.

"Don't get too used to it." You tell your stepsister. "Now, can you unlock me?" "Whatever do you mean?" Bailey looks at you queerly. "You promised that if we started on your project tonight that you would let me out after!" You splutter in indignation. "No, I said that I would let you cum, not that I would unlock you. But, come on then, let's get this over with." Bailey grabs you firmly by the hips before turning you so that your facing away from her. Her hands then tug at your waistband, sending both your trousers and boxers to the floor. "Wait... what are you doing!?" You exclaim as you look back and see Bailey sucking on one of her fingers as a draft caresses your bare ass.

"Making you cum, silly." Bailey replies, taking her saliva covered finger out of her mouth before plunging it deep inside of your virgin rosebud.

"Ah-eeeh!" You let out a very unmanly squeal. "Hold still dumbass. Bailey's looking for the on switch." Your stepsister bites her tongue in concentration as her finger wriggles around inside you. You try to pull away but Bailey brushes against something inside of you that causes your body to light up like a Christmas tree. "There it is." Your sister announces with glee.

"Oh-my-fucking-geeeerd!" You involuntarily sink further onto Baileys finger as she flicks your pleasure switch up and down repeatedly! "What a slutty hole you have Sammie." Bailey giggles. Before you can comprehend what is happening, your cage erupts without you even getting hard. One spurt, two spurts, three spurts, four... you begin to lose count. "Wow, so quick!" Bailey teases, feeling you clench hard around her finger as she milks your prostate. "That's a good girl. Let it all out." She leans round to watch. Only when the last spurt dribbles from your cage, do you feel your stepsisters finger pull out of you with a wet pop.

"I can't believe I- I mean you just did that!" You blush, reaching down and hastily pulling up your trousers. "You're welcome. You know, you're quite the anal slut Sammie." Bailey sniggers, walking over to her nightstand and grabbing a wet wipe to clean herself with. "I've never made a boy cum so quickly from his ass before!" She declares. 'Wait... how many guys asses has your stepsister played with?' You start to wonder before getting back on track "It's just because I haven't cum in so long is all." You say defensively. "No guy could last much longer after being so backed up." "That must be it..." Your sister rolls her eyes, smirking at you as you awkwardly shuffle your tender asshole out of her room. "Come again soon!" She mocks.