Replies 2

Not OP
If it's first time
Lots of lube. Can't recommend it enough. Might want to fuck her first, solid O, make her cum hard so she'll relax. I usually flip after so she's doggy. Lots of lube down the crack. Finger and toy her pussy. If she just I'd it's tender so be gentle. Vibrator comes in handy here... it's the soft vibrations, not so much the insertion. Think of it like her edging your cock. Maybe you get another O, definitely help her relax. When it's that time, finger her asshole first. Goes without saying but make sure your fingernails are trimmed. Lots of lube, very slow, remember assholes are sensitive. Tease around the rim, insert a few times, always gentle don't shove. Goal is lube in the hole and keep her relaxed. Hardest part about getting your cock in is getting the head in. More lube, make your cock slick before you even try. Slow, gentle, even pressure. Resist the urge to fuck and shove. Depending on her relaxation and your cock size you may need more patience. Keep teasing and toying her pussy if you can reach it. Eventually you're in and then it's taking it slow, and very slowly ramping up. It's probably the tightest, most powerful fuck of your life.
If she's into it and you think it may go anal, plug her as you toy her during foreplay. That will drastically speed up the process later when you pull the plug and start inserting your cock.