My Boss Is Your Boss
Scenes 12 min
Cruel Girlfriend

My Boss Is Your Boss

Cast
Jessie Jensen
Release date
Runtime
12 min
Studio
Cruel Girlfriend
Tags
Chastity ToysCuckoldingHumiliationMissing Cover ImageSissification
Code
676

So I think it's about time you came in to the office to meet my new boss. I've told you so much about him already it'll be good for you to actually meet him - after all if I'm the boss of our relationship and he's the boss of me that means technically he's the boss of you too. Aw I know beta wimps like you get shy meeting new people - especially confident alpha types like him, but he's already kinda insisted on you coming in to see him. Y'know, I've got to know my new boss quite well over the last few weeks - we've gone out for lunch a few times, drinks after work and the more frequent out-of-town meetings we've had to stay away together for. In all that time I've told him a lot about 'us' and how you're basically my submissive, obedient little slaveboi and that I totally dominate you - which he found hilarious. My boss thought it would be a great idea if we BOTH dominated you. Him and I would start to date, you'd become our cuckold and you'd learn to serve us both. Aw don't look too upset cucky - you still get to see me every day, you just don't have boyfriend status any more. My boss wants you to come in to the office so we can explain the rules to you together but just to give you a little advance preview - you basically don't get any sex anymore - your cock stays locked in chastity. You have to wear girl's clothes around us to remind you of your emasculated status and you have to serve us ALL the time - that means at work and at home! We're going to give you a demeaning position at the company and a humiliating life at home. Any questions cuckold

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    Sources StashDB 2026-10-06

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