system
A chat on subreddit /r/NoStupidQuestions
human
Pulling out doesn’t work. 
There is no safe day. 
Never go anal to vaginal. (Bacterial infections happen that way.) 

Never double up on condoms bc the friction will break one or both. 

Always keep a spare condom in your wallet so you never have to worry about it. (Edit: good point made, keep it In a container where friction will not cause it to break, probably keep 2-3 of them also.) 

Just because one of you is on birth control doesn’t mean you can’t catch something. 

It’s normal to experiment with different stuff. 

Having a fetish doesn’t mean you’re a freak. sometimes people just have fetishes. 

There’ll be gross and funny noises and that’s okay. 

Remember that sex is a two way street, try to reciprocate for your partners. 

Sex is easily 65% in your head. If you’re having trouble, just try to stay in the moment. Don’t worry about the how’s or why’s. 

Being vocal is hot, it’s okay to be vocal. Also don’t assume everyone will be. A lot of women don’t make much noise unless they’re trying to for their partners ego. 

Communicate. Ask for consent. It doesn’t have to be stiff, it can be playful. 
Example: “You want me to (insert nasty action here), don’t you, (insert sexy nickname here)?” 

Pregame. Flirt. Touch. Kiss. Let sex be the ending to a long and heated session of prep and foreplay. 

Anal sex requires long preparation. That can include things like monitoring your diet to ensure you don’t have a hard time cleaning it out. 

Vaginal sex requires some prep but usually not as much. Most of that is foreplay related.
gpt
Keep 3 condoms with you! 1 condom is a recipe for disaster when you're having the night of your life and it slips off/can't stay hard because nerves/want a morning goodbye quicky.