Milly takes him up a peg

You pull up your chair to watch as Milly tutors Daryl, maybe you’ll learn something. Milly isn’t shy about flaunting her tight little body for him.

“Daryl, I’m going to teach you how to have a sissygasm.”

He tries to withdraw and she sits herself on his lap “No, not like that!” She takes his hand and lets him feel her cage “I’m going to teach your ass to cum, no infection required!”

“Don’t be like that, it’ll be fun. No! It’ll blow your mind” She smiles hungrily “and your load.” You can both feel the tension in the air, it almost radiates off of him. It’s been too long since he has cum. In the face of her temptations some might call his resistance heroic, though you’d call it stupid. “It’s fine Daryl, we can’t really fuck. Butt…”

Milly pulls the harness out of the bottom of her teaching materials, good for her she’d fully explored her box. She purrs at him “Daryl, I want you to put me in my place.” She reaches down around his waist securing the strap on right next to his cage which looks to be painfully full. She rests her flat stomach across his desk and lifts her skirt “Make me your little sissy bitch!” You stroke faster as you watch him accept her invitation, he lines up behind her and starts to slide deeper into her. She moans loudly encouraging him to new heights or would that be depths? He powers on fucking her good and hard. She plays the role of the horny little cock slut perfectly. She’s moaning so good that you join in cumming across your desk as she cums on his. When she manages to lift her head she looks you in the eyes and winks conspiratorially.

“You made me cum so hard, was it good for you?” It’s obvious that he isn’t satisfied. You didn’t expect him to answer, but then he growls at her “No!” She turns over and pulls up her shirt only to begin kneading and pinching her breasts. “How can I help master?” He doesn’t seem to know, but you’re sure that Milly does. “Would you like me to pleasure you Master?” He nods and she latches her lips around one of his nipples sucking it hard as she rubs her breasts against him. His eyes close and his lips open, he’s feeling it. She takes her chance and slides the tip of her index finger up his ass. His eyes snap open wide. Milly swirls her tongue around his hard nipple and asks innocently “Have I done bad Master? I just want to please you.” He hesitates and her finger slides deeper, he gasps as she wiggles her finger up against his sensitive insides.

She works her way deeper and deeper until her finger is swallowed by his ass, all the while she’s calling him “Master”...

When she’s sliding the well lubed up strap-on up his ass, it’s on his orders and he’s convinced it’s his own idea. He’s bent over a desk as she enthusiastically plows him. She helps him find his anal pleasure and he achieves release dropping his small load on the floor. When he rises off the desk she dives to the floor to lick up his cum. She looks up at him on her knees and opens her mouth to show him his load, then she loudly swallows.

“Master you taste so good!”