So you’ve decided to go Greek. Anal sex can be good fun for everyone involved, as long as there is an adequate prelude.
Note that this article will strictly discuss penetration inside a woman’s ass. Pegging, wherein the man’s ass is stimulated by a woman wearing a strap-on, will be the topic of another article. Fun fact: even if the height is the same, a woman’s asshole is considerably smaller than the man’s.
In general, especially for a first timer, or a woman who just doesn’t do anal particularly regularly, it’s good to have a prolonged time of stretching the ass out, lubing it up, and getting it used to sensation there.
You can start with analingus / rimming / licking her asshole if you like. The details of this will be the subject of a different article.
Then lube up a finger and insert it in, slowly sliding it in a circular way a little bit inside, and then gradually push it deeper. A good rule of thumb with any sort of anal activity is that there is no such thing as too much lube. So just keep applying it to your finger and sliding it back in. Do that until you can slide your whole finger in and out, then try to add a second.
You can then use some beads, these are anal toys with progressively increasing size balls, that you can insert into the ass and then vary how much it fills up. Lube it thoroughly and slide back and forth bringing the balls in and out of her ass, keep going until she can take the biggest one in. From that try to gauge her readiness for your cock (as in, if you’re a dude reading this,, she’ll definitely be well ready for yours by the middle ball. in my case she’ll still need to be very gently introduced to my dick after even the biggest ball)
Oftentimes the easiest position to start with is her lying on her stomach (second most common is the standard from behind, maybe 3-1 ratio). Slide it in and immediately take it out put lube on, repeat until it’s well lubed and you can go deeper. Go slow and deep and keep adding lube for a while. Eventually it’ll really feel smooth and you’ll be able to glide in and out well, and at that point she will be well relaxed now. Enjoy 🙂 In regards to positions, from behind and her on her stomach will probably be your gotos, but with a bit of stretching her legs she can take it on her back with you on top. Some connoisseur women like to also ride with their ass, that’s a nice sight.
Fun fact: slapping the ass relaxes her ass muscles, and thus facilitates a more pleasant trajectory for your cock for the both of you. Use this tip liberally during your activity.
I’ve found that about 1/3 of women will not feel much from it, it can be interesting, but is not particularly arousing. Another 1/3 are mildly aroused, and a 1/3 love it, maybe 15%-20% can cum anally.
It depends on the placement of her posterior fornix, the spot at the bottom back of her vagina, in some cases it can be closer to the anus than others, it’s hypothesized that it’s through this area that the anal orgasm takes place, it stimulates that spot or orgasmic tissue around it (part of the “clitoral cluster” note this is still just hypothesized).