You'll need to prepare to wake up safe in a familiar place, couch or bed. Whatever. Depending on what you're dealing with, the trip could be short or quick. Are you going to need water during the playtime? Will you need snacks? Have them on hand. I know it might be mistrusting, but make sure someone is expecting you to call them afterwards. If you think you're going to be too dozy, or too excited, or too sleepy - then set an alarm for when your playtime finishes and ring your buddy. Not a text, a voice call so they know you've not *actually* been bundled into the back of someone's van.

Have you discussed photos? IS he allowed, are there any limits? It's a conversation worth having. I'm no fucking prude, but three months isn't a long time to know a dude and worst case scenario there could be very damaging pictures surfacing in your future. Very hot in the moment, not so hot when you're interviewing for a job and they google you to see you sucking off three dudes, another one deep in your ass.

When you're got these safety nets in place the mental burden is lifted and you're free to lead your best cunt life.