If you adhere to these tips, it shouldn't hurt.
Anal sex isn't for everyone, but what better to really try something new in the bedroom? Here are some great tips for trying anal sex without any pain, and quite possibly, finding it orgasmic.
1. If you can't see it happening, it never will happen.
This is probably the most important tip of all. You have to want it and you have to be able to envision it happening successfully. Your mind is a powerful instrument and it's an important element to this type of sex.
2. You must know your own body.
You should feel clean and relaxed. If you have favorite positions for vaginal penetration, try those first for anal penetration as this will help you feel more relaxed. Take a shower first so you're 100 percent confident.
3. Make sure to lubricate.
The best results happen when you use silicone lube. We love the very good silicone lubricant Eros bodyglide by Pjur. Silicone lubes stay silky and slippery, and don't get sticky like water-based lubes can. They won't dry up like water-based lubes, either. Your anus doesn't lubricate like your vagina when you're excited, which is why water-based lubes don't cut it for backdoor action.
4. Use a condom for all anal sex.
Even put a condom on any toys if you're using them anally, as it's much easier to sanitize later. Toys can take on a bad odor if you don't, so help your toys stay nicer longer.
5. Stimulate your clitoris during anal play.
Orgasms or clitoral stimulation can bring blood flow to your pelvic region. When you put a bullet or other toy on your clitoris, it stimulates the "clitoral legs" system and helps the sphincters to relax. If anything hurts, stop; anal penetration shouldn't hurt.
6. Use your fingers or a small anal toy.
Use the Bendi butt plug to warm up for anal sex. Never use a sex toy anally unless it has a stopper on the end so it doesn't get lost in your anal cavity. Excitement can pull toys into the rectum, hence all the 3 AM emergency room stories.
7. Remember that not everything you see in porn is real.
As Jayme Waxman said on Better Sex Radio, porn stars are sexual athletes. Our male partners have to understand that we aren't porn stars. Regular women cannot do what porn stars do; women have to take it slow and control the penetration.
Let the female partner move onto the penis; the man should never be the one controlling the insertion and penetration. No crazy jack-hammer humping your female partner anally ... unless she begs you to, of course.
8. Use your muscles.
Women should use their muscles to push as they move onto the penis. Pushing helps relax the muscle set in the anus and opens it up a bit more to allow for penetration.
Above all, remember that sex is supposed to be fun.