Boy Skips Class and Gets a Spanking from his Sister

David is a 6’ something die hard sweetie with a penchant for gadfly-like antics on the internet (Jordan Peterson, anyone?). He’s cheeky, and so are his fantasies. His smile is big and broad, his eyes are blue, he cries when he’s beaten, and he perspires when he masturbates. He’s a big teddy bear with a smart brain which adeptly spins sexy fantasies, but think 16 year old boy fantasies rather than collars and whips.

I love receiving The Script because it’s when the session actually starts. The conjuring, the day dreaming, the naughty glint in his mind’s eye. This particular one arrives in the form of an early morning email sent from a hotel room on a business trip. Hotel rooms remind him of his youth - lack of parental supervision, the feelings of freedom and anonymity. I like to think he spent the night tossing and turning as his perverted thoughts mapped out a new role play, one which we will play out and enjoy to it’s utmost, squeezing it until the last juicy drop has fallen.

The scene starts on a school day while our parents are vacationing in Europe. I’m his older sister and have my hot but sexually innocent friend over (played by Ms. Veronica Sway). David has been left in my care and is lounging on the couch when the phone rings. It’s Mom, and she is furious! She received a call from school indicating David had skipped school that day. To my defence, I had dropped him off that morning.

Mom is a spanker. She doesn’t want to wait two weeks until she is back home to spank him. She tells me to do it, but I protest, arguing that it’s not my fault, and that I’m busy hanging out with Veronica. I’m now so annoyed by my little brother that it’s going to take a lot to convince me to mete out the punishment. Mom offers me $100, and adds another $20 for Veronica to stay and watch. She also demands a text with photographic evidence of his bare, rosy bottom. I finally agree.

I hang up and tell David the bad news. He begs me not to! But I want my money, plus David has been quite naughty… I tell Veronica about the spanking and of course offer to cut her in if she stays. Sure! She’s excited to see me spank him actually. David wails that Mom was away, that he thought he was free to skip ‘cause she’s on vacation (what an idiot - cell phones still work in Europe!).

I make him strip to his underpants and already a tent is evident in his shorts. Both myself and Veronica notice it right away; we point it out and tease him about it. Veronica wants to see it as she has never seen a boy’s penis before (she has no brothers and her parents are very strict). I have way more experience with boys, and have seen my brother stripped for his spanking on various occasions. So I pull his underpants down and make David put his hands at his sides so that Veronica can give his erect cock a long, good look. 

I take him across my knee and deliver a pretty hard spanking. I use my hand to warm up and then a wooden hairbrush. Not light, not viciously hard, but more like a thorough, drawn out, disciplinary spanking. I ask if Veronica wishes to take a turn also. She does! When his cheeks are rosy and bruised we make him pose for the pictures for Mom. We both tease him about how he carried on, kicking and whimpering like a teenage girl. This teasing gives me an evil thought! I make David bend over and hold his cheeks apart. He complains loudly which leads me to threaten to tell Mom that he’s been disobedient about the spanking. He wants no part of that so reluctantly does as he is told. I lube up his bottom hole and then insert a tampon! We both laugh, and make “Little Miss Cotton Tail” hop around the room, giggling as his naked cock and tampon string bounce with each step.

We’re having such a laugh at his expense when Veronica asks if she can touch his penis. Of course! She pokes at it, squeezes it, bats it around a bit. She examines his balls. Squeezes them. She is fascinated! She rubs it a bit and watches David’s knees shake. What fun! She wants to put her mouth around it (she has heard of that) so I let her try that out. It’s her first time! She asks about ejaculations. She wonders if he is old enough to spurt? I’m not sure if she is joking or just really innocent, but I tell her that his bedroom is right next door to mine, and that I hear him jerking off practically every night! (David is mortified at this realization!) Veronica then asks if she can watch him do that...

I make David go upstairs to his room and instruct him to pull out the Playboy magazine from under his bed. He is horrified to discover that I know his dirty secrets, but can’t help rubbing his erect cock as he stares at the centrefold. For inspiration I suggest that Veronica expose some skin - she does and he’s clearly excited. I allow David to touch her a bit, but then Veronica suggests that he also look at me while he’s rubbing himself! I laugh, saying that he’s not turned on by his own sister. We decide to experiment, and David only seems more turned on. Ha! What a pervert.

Amidst all the rubbing and visual stimulation he makes a mess all over himself. I’m completely unbothered by it and roll my eyes at Veronica before ordering him to clean himself up. He sheepishly scoops all of the white, thick cum into his mouth and swallows it.