If your're thinking of buying the most popular inflatable plug (sold here as Deluxe wonder plug or Expando butt plug) don't. It's not a beginner toy and people with tight asses (me) have trouble taking it after playing with something smaller and/or fingers. It would just frustrate you. It's wonderful when I finally manage to get it in.

The thing that is tight is your sphincter - not your rectum that is stretched by inflatable things. If you pump an inflatable toy up the air would even out the pressure by going to the part that's squeezed the least.

Try taking your time, working out fingering techniques that work (for example less thrusting - that tires out your ass before the thing you're prepping for happens), breathing exercises and visualizations. For example: you breathe out, relax and open the muscle, slide a finger partway in, and then clamp down on the inhale. Another exhale, you open your ass, finger goes in deeper. Slowly, without rush until you manage as many fingers and as deep as you want and you feel open and relaxed.

You can also shop by diameter on Eden. There are some awesome smaller but toys.

As long as you listen to your body and don't try to ignore pain you should be fine. Tears happen when people use desensitizers, are drunk or stoned or simply don't feel able to speak up when it hurts. If it hurts slow down, try something smaller or reschedule anal for a "good-butt-day&qu ot;.