I've never been penetrated by another person, but I have, with a Femdom been penetrated with a strap-on.
At first, I was very apprehensive about it, thought it would hurt like hell frankly. But if its done the right way, it can be a very pleasurable thing. The key thing to remember is to use copious amounts of lubricant, and go very slow, let yourself relax and gradually you'll be able to take it in. Your body will fight the intruder at first, but just relax. You'll find yourself enjoying it without too much pain. I don't recommend a hard ramming the first time, but over time, you'd be able to accommodate it readily
The anus has a lot of nerve endings that can really add to one's sexual stimulation.
If you want to try and condition yourself on your own, I recommend getting a butt plug. Get a small one, use plenty of lubricant, then slowly insert it. DON'T PUSH. Over time, you'll find yourself eagerly, and easily able to insert it, and will begin to enjoy the full feeling it can provide.
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