Some recommended dildos but I will walk around (and sit on) one of my favorite butt plugs in for at least 1/2hr before an appt where I will be expecting greek
Sylvia, my massive 5 incher could be just what you are looking for to help ease on in for the first time. Well, from where i stand it appears to be a massive 5 incher. What say u?
Trust & time. Take the advice of White Chocolate and TxCwby6.
Find someone that you're extremely comfortable with. Find someone that you KNOW will take all the time YOU need. Find someone that loves to DATO.
DATO, DATO, DATO. Then add some finger action. Not in, but around. Light touch around and around. Gradually increasing the pressure, but not inserting. Then some DATO, DATO, DATO. Then more finger action, not forgetting the other areas close by. More DATO, DATO, DATO. Then some light, not deep insertion, almost massaging around the rings. Then some more DATO, DATO, DATO. Then replace the fingers with his penis for more massage, not insertion. Sort of like an anal stripper slide. Then more DATO, DATO, DATO. Throw in some DATY for good measure any time you want him to. At least this works very well for my current FWB.
At some point in this YOU will know when YOU'RE ready. As much lube as you feel you need, but for the first time don't underestimate, but also leave it until you're ready (DATO isn't good once the lube is on!!!). As WC said, if you've got this far, he should slide in very easily.
For me greek is the icing on the cake, not the main event itself.