O365 - Outlook

corygreen With Outlook 2016 (comes with E3 subscription), you can create a meeting request, submit it to your supervisor, wait for him to acknowledge, then simply delete it and select to not send a meeting update.  This will leave it on his calendar but remove it from yours.

Of course, if you had access to his calendar, you could create the invitation directly on it, but I'm doubting you have it else you wouldn't be asking!

Another option would be to create a shared calendar with your supervisor for these types of events (it's actually what I do with my team).  This way my staff can add PTO requests and maintain our on-call rotation so everyone can see it and edit it from the shared calendar.  I did this using Office 365 Groups.

Hope this helps.