Only do it when you are ready. Some people can never overcome certain feelings about it being "gross" or "dirty". If you are clean before you do it (water enema, good shower), you may be able to enjoy it more. Finally, relax..It can feel good. Even if you never insert more than a finger or a small plug, that's just fine and is usually enough for me to get me very excited. And if you don't like it, that's ok too.

As far as the kit, that may be a good starter thing, but the safety rating isn't the greatest and the rubber is porous so make sure you are the only one using them or put a condom over the big one. At least with a silicone plug, you could sterilize it better.

Good luck!

Everybody has different tastes and vary in what they like about their sex. My Man and I engage in anal play and anal sex, (me being the receiver only) I know when we started, we didn't start with a toy. He gradually introduced me with his hands and gently got us used to anal play that way. We tried a plug, but I didn't like it so early on. I have to agree that for me at least, real flesh is usually the best way to learn things. But, that's just my opinion. I think Carrie Ann once said, "You don't prepare for vaginal sex by sitting around with a dildo in your pussy all day, do you?" No, you don't. And, while a lot of people like anal toys, we found we only started using them after we got acquainted with anal play and anal sex.

Your mileage may vary. But, for me, I never would have just stuck a plug in my ass on my own. It was part of partner play, and for the most part, always is even at this point.

Kindred made a good point about being well stimulated before even trying anal play. I find this to be true. Even though My Man and I are well acquainted with anal sex, I almost always still have to have an orgasm or more than one to even want it. I CAN do it without coming first, it's just easier and more pleasurable if I get to come first. That being said we DO use anal toys during whatever "foreplay" would be for us, before orgasm, but that is only after a long time of just using body parts in this type of play.

You probably need to experiment to see what works well for you, what you find arousing, what fantasies you have been having about this type of sex, and then decide if you to go Toy First to Flesh First.

Only a few caveats; 1)It if hurts, STOP. If done properly it shouldn't hurt. 2) Do NOT use anything to "anesthetize" the anus. Pain is your body's way of letting you know something is wrong. You could get hurt, badly, if you are numbed and don't realize something is wrong. Please, don't use numbing cremes, ointments or sprays. 3)Use a good lube, preferably not a "warming" or "tingling" lube, but something thick that will last. 4)Go at your own pace.

And like Passion said, some people never come to love anal play. And, that's OK. Do what turns YOU on.