""It's sad, the first experience can make or break the entire idea of anal sex, it's like hard mode and you only have one life""
So you're interested in anal, huh? We have something in common!
I've always been an anal fanatic and throughout the years I've introduced many women to the pleasurable (and not-so-pleasurable) effects of anal sex, and although a lot of it varies from person to person, I think I've got a solid technique going.
First of all, ask yourself "Am I okay with getting a little poop on my dick?" because if the answer is no, anal is not for you. You will inevitably end up with a little mess from anal, especially if you intend on doing it frequently. This is just a matter-of-fact kind of thing, because believe it or not, anal porn is not an accurate representation of anal sex.
Second, do you have lube? Lube is an absolute necessity for anal. Do not expect to make progress otherwise. The kind of lube you use however can vary. There are 3 kinds of lube: water-based, silicone-based, and oil-based. Oil based lasts the longest, but will harm condoms and toys. Silicone based lube is pretty sticky and lasts a while, but will wear down silicone toys. Water based lube is the safest of the 3, but it also dries out the quickest and is the most sticky.
Third, will you use a condom? Even though pregnancy is not an issue with anal sex, STDs (Sexually Transmitted Diseases) and STIs (Sexually Transmitted Infections) still are. UTIs {Urinary Tract Infections) can be avoided simply by clearing your urethra after anal sex, aka: peeing. If you are with a long term partner that you trust, you should be safe to engage in anal sex without a condom, if you have any doubts or disbeliefs I highly recommend using a condom and water- or silicone-based lubes. Oil based lube will wear down a condom and render it ineffective. Of the two, I would recommend silicone-based lube more, because of how sticky and long lasting it is.
Fourth, consider your size! If you are relatively big, I recommend you urge your partner to sleep with a butt plug in, in order to make the whole ordeal as painless and pleasurable as possible. It can be any size, but the closer it is to you, the less issues you'll run into. I have a Doc Johnson classic medium plug and it has worked like a charm, not to mention my partner loves it.
Last, positioning is everything! If you ever want to have anal again, make sure you gauge how your partner is reacting to what you do. If you're going balls deep in-and-out and you can see your partner in pain, you know you're doing something wrong. Some tried and true positions for anal beginners are: cowgirl, reverse cowgirl (because it gives the woman control of the speed/depth of penetration, which is more helpful than you may thing), and of course doggy style.
There you have it, 5 basic steps. When you think about it, it's a cheap trade-off for a great time. I strongly believe anyone can enjoy anal if properly introduced to it. I have rarely had been able to not make a girl orgasm from anal sex. Good luck and have fun!