GET NASTY

My boyfriend and I recently started to chew chum during anal, at least in the begging, because it helps keep you from overthinking about the first few thrusts.  Simple, effective, and waaaay safer than poppers.  

If chewing gum doesn’t work for you or your boyfriend, I would then just recommend lots of booty foreplay:  Can start to rub the buttocks to help start the mood; when ready, go ahead and make out with the hole–slowly at first, then begin to increase pressure with your tongue; once the rimming is over (or on pause), you can add a drop or tube of (mmm, flavored) lube to one or two fingers and begin to massage the hole, as with the rimming, gradually apply more pressure, switch between one finger and two; eventually let the sphincter “accept” one finger (you can move onto two fingers once the partner feels comfortable enough); if yall have any anal toys, this is when you can bring them out and experiment with them.  ANYTHING THAT YOU PLAN TO STICK INTO THE BOOTYHOLE MUST MUST MUST HAVE A WIDE, SOLID BASE SO IT DOES NOT SLIP INSIDE COMPLETELY; THAT WILL NOT BE FUN FOR EITHER/ANY OF YOU.