To a newbie to **** play and prostate massagers, this is a fun little toy. Being a first-timer, I found the 1.4" head ... well, let's say a bit more than I anticipated, but with some patience and plenty of lube I got it in there. This is one time you really don't want to clench up, so a little massage and tip-of-the-finger action first will help. Once past the sphincter, though, it slid in on its own and my **** gripped the tapered shaft firmly. I did find I had to stretch the ring over my **** and balls first, to get enough length on the strap which connects the **** ring to the plug to give me a good angle for insertion. But once the plug was fully inserted, I could slip my balls out of the stretchy ring and let it do its magic on my **** alone. This thing gave me a massive ********, so the 1.5 inch diameter of the **** ring was a perfect size for me, not loose at all. Hopefully, continued use will make insertion a bit easier, and boy, do I ever intend to use it again! I wish the vibrator was a bit more powerful, and had more than just the one speed -- which is why I gave it only 4 stars -- but what do you expect for the price? Particularly for something that feels this good inside, and the sensation as you thrust and it rocks against your prostate is something else. I came like a fire hose.