To reduce pain/discomfort as much as possible, here's my plan:. . A few months before the magic moment, you should try to start stretching yourself. You can do this several ways- the 'home' method, or the 'professional' method. The home version just consists of going slow; every day, spend a half hour or so either having your partner or yourself inserting fingers. Start with one; a week later, try two, and so on, and so on. The professional method includes buying a variety of dildos and butt-plugs in various sizes, going from small to approximately the size of what you eventually plan to take, and use them in increments, just like the fingers. Remember, always space it out between a week or so- no fast rushing. Let your body adjust to it. If you are seriously dedicated to enjoying anal sex and want to get there, you can purchase a flexible (emphasis here on flexible) buttplug that comes with ties that can be fastened around your hips/thighs, keeping it in place. You can then discreetly wear it all throughout the day without anyone noticing (believe me), and really fitting you perfectly- not to mention maybe giving you a little sexual buzz during the day! Continue up in size until you're able to take what you want. It might still feel like a bowel movement, but I'm betting that once you get more accustomed, either the feeling will go away, or you'll be used to it.. . Now, when the big day comes, or even as a preclude to the special moments I described above, this is the routine you want to follow:. . First off, you want to make sure you're completely empty- go and sit on the pot for a while beforehand and make sure you truly are empty and nothing will be lying in wait, so to speak. That's not to say that you won't get that customary 'I'm going to have a bowel movement' feeling that is often a part of anal sex, but you'll know it means nothing. After that, you can clean yourself out, either just with some soapy fingers in the shower/tub, or a full-on enema that will ensure that you are completely clean. Then you're ready to go! After that, you need lube, lube, lube, and more lube. Only- please don't use numbing sprays! They're not a good idea; you do anal sex for the pleasurable feeling, and masking that is sad. Not to mention that if anything bad happens, like an anal tear or something, you won't be able to feel it- risking sexual health and possible big injury. Use a good, thick, lube, and a lot of it, deep inside you.. . Next step- a vibrating buttplug- one that doesn't have to be big at all, if you don't want. It's just pretty much necessary if you don't find yourself opening up easily or feeling uncomfortable during anal sex. Lube it up and insert it, and then turn that sucker on. While it's running, that's your time to start pleasing yourself, since anal sex is all about relaxation. Either you or your partner can do a variety of foreplay-like actions, and if you can have an orgasm or two (from clitorial stimulation) within that time, all the better! It will relax you a lot. All in all, the plug should stay in and vibrating for about fifteen minutes to shake you all loose and get you ready.. . After that, it's all about how you feel. If you think you're ready, start the penetration . . . if not, your partner can continue some playing with the anus to help you. But eventually you can go- remember, to help take whatever it is, you can always 'bear down' like you're trying to have a bowel movement, which can help slide it in easier. Go slow, breathe (it helps to push it in a centimeter at a time as you breathe out), and use your fingers or have your partner use theirs to manually stimulate you- that sensation can shift your focus so you don't feel whatever's going on back there so much. And that's about all you can do, in the end.. . Those are just some tips I've le