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Challenge: Dont cum until you’ve learnt to cum anally!
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Once he’s been locked long enough, there’s always some winning combination of anal, electricity, breath restriction, and hitachi that ensures he cums when I want him to. Chastity cage on or not.
Was that your first time being pegged? I guess I could’ve been more gentle, it’s just…I’m not unlocking your cage until I get to see you cum through it.And I thought you wanted out soon.I know, I know. We didn’t quite get there. But I’ll
Got a surprise for you, boy. I got a squirting dildo to humiliate you more. Want you to feel cum bursting deep inside your ass when I peg you.But then I realized: if you wear it & that burst of happy juice satisfies me right…I could probably
I will set goals for you, and when you achieve them, you will get a short release from chastity.Your first goal is to learn to cum from anal stimulation only. I will peg you often, but you can train yourself as well. I want you to drink a ruined orgasm.
I had a lovely time with you. Date night’s never been so fun.Wasn’t so nice for you? You said you wanted to try anal.What? No, I lied. The key’s at home, safe.
Asking me to release you from chastity is bad enough, but you KNOW I’d never do it before a pegging!
I only have one rule: He can’t ask for release unless my thick rubber cock is balls deep in his ass.This makes him beg for the peg when he gets desperate for release.The cruelest thing was denying him even the pegging. Until he REALLY begged for
Pegging is just so much better when he’s caged.
Pegging all night
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