Like said before you should let him fuck your ass and cum in it. Then you should put back the plug in right after that so it keeps his cum inside you.
You definitely should sick his dick after he cums in your ass until you got home. Find a way to persuade him for that ! If you fail your punishment is that you have to spank your ass in the car for the end of the ride 
When you finally get home, invite him inside to fuck you more, and let him know that you will do that again whenever and wherever he want (including office).
Then your final dare, when your home is to put out the plug and let the cum drip out of you in some kind of plate. Then you have to make a video of you while you eat it all, and send this to your boss with a message like " can't wait for more".
Of course you should put the plug back for the night as a memory of your ride
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I am a 20 years old switc searching for dares to do or to give.
Likes : Masturbation, Restrictions/Temporary rules, Bondage, Spanking, Punishment, Nipple torture, Breath play, Anal, Ice, Humiliation/Degradation, Public, cross-Dressing, Pet play, pain, Cum, Deepthroat
Dislikes: Edge, Bladder control, name calling, Hypno, wedgies, messy, ruined orgasm, cbt, chasisty
Limits : Health, Lifestyle, Scat, Enema, illegal, ATM, permanent, pics/vids
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