Anal Sex

I don't have very good experience with anal penetration. Mostly because the guys I've tried with always rushed and wanted to jump right on it without taking care to prepare me.
But I do like rimming a lot tho! Even slightly touching of that area including oral is getting me to orgasm really quick.
 
As a woman it took me a little while to enjoy it but once I got the hang of it (the right position, lube etc) and knew how to prep it was a dream!

For me the orgasms are really deep and when mixed with clit stimulation......its like what I imagine yogis experience when they talk about reaching enlightenment haha.
 
I tried it once with a lot of lube and preparation and it wasn't painful or uncomfortable. A bit weird feeling. Not bad at all but not like wow.
I get why anal stimulation can be nice and it's not supposed to hurt when its done right, but it takes time to prepare and its nothing outstanding for me.
 
I don't have very good experience with anal penetration. Mostly because the guys I've tried with always rushed and wanted to jump right on it without taking care to prepare me.
But I do like rimming a lot tho! Even slightly touching of that area including oral is getting me to orgasm really quick.
I've had many girlfriends that could do anal and I like more capable women. So I've studied the issue a lot. Around 35% or so of my girlfriends overall could do anal sex regularly.

1) Knowing she can do it versus thinking it's not possible or too difficult.

A funny experiment that I have tried that's been unexpectedly very successful is showing anal sex movies to women. This has worked, as many women have no idea that anal sex can be done without blood and extreme pain, as they are thinking. When they see other women on video do it, they realize it's very possible.

Of course women on video are often more experienced, but there is a lot of amateur and regular women on video now. A lot of the issue for many women are horror stories they heard from other women. They think it will be so painful and impossible, because of what they heard. Seeing anal sex is possible helps a lot of women.

2) No surprises and go SLOW!

This is where guys often make the biggest mistake. They try to surprise her or rush. Neither works well with anal sex. They pull the drunk guy slip into the other hole routine with no lube and then cause a ba experience. The women is a bit traumatized, so never tries again.

I want to strongly emphasis to never surprise a woman with anal sex. Get her mentally ready and get her full corporation.

3) Knowledge on ways to get a woman ready

A) Really good lube. Have 2 or 3 kinds ready for newbie women.

I'm not sure why, but different lubes work better with different women. So with a newbie, you might want to experiment.

Very experienced or flexible women who have a more oily type of vaginal juices might can do anal sex without any artificial lubrication, but this is a more rare woman. For the 1st time or with a newbie, a guy should use lube, NOT spit or vaginal juice. It seems some guys don't know this.

B) Make anal play part of your regular sex play.

Not just penis to anal, but using well lubed fingers or your tongue. Lick her clit and finger her anus, then possibly 2 or 3. When she is on top riding you, put a finger in her anus. Rim her anus with your tongue.

You can use toys as well. The best methods that seem to work are anal plug or dual plug vibrators. Both can be bought in Japan at Don Quiote or sex shops (Shinjuku and Shibuya in Tokyo).

What makes a butt plug easy is that you can insert it, and go have regular sex. The butt plug will loosen her up. So then after vaginal sex, you can more easily insert the penis.

4) Relaxing or a bit of wine

The women I've met who could do and enjoy anal sex the most, were the more relaxed types.

When a woman is nervous or uptight, anal sex will be more difficult. A guy should try to recognize this personality type or situation. So to be more successful, do things that get her more relaxed. Some wine, a coconut oil massage, a warm bath or jacuzzi at first, etc...