Without considering the threat of HIV, do you have an intention / desire on anal sex either with your gal or WG. I think many guy will answer I wonder try.

To-date, everyone talking about innovation & change, simply speaking what is new to your daily life. If you desire something difference like an iphone and add colour in your sex life, anal sex can be a good answer.

First of all, It’s a matter of sex knowledge and how much satisfaction during intercourse, slightly mature gal & WG will have more open mind in anal sex thereafter I don’t encourage young couple to have anal sex before they really understand what is sex.

Anal sex with gal & WG is no different, we are not talking about technique and skill here, but to elaborate it is not a matter of guilty:

With your gal.
Don’t think it is your duty, it is the couple cooperation in achieving another degree of satisfaction for both. If both of you already try different style of sex, like oral, DATY, surf and turf, analingus, CIM, you can try anal. If not it is not our discussion today. Anal sex like any sex is not a sin, therefore take it easy as usual. Whatever you take a condom or not, you should completely clean your bottom & every step should be slow & until both of you feel comfortable just like normal sex. The use of ky will definitely helpful. Male should not be dominant over the game, female can also pay an important role, therefore I just simply advise a “side by side” position at the beginning. Any other positions leave to the reader.

With the WG
There shall be no different with your gal except that they are “professional”, anal sex for them is just like a coffee, therefore you can pay a dominant part in the game. To my observation, anal sex with slightly mature WG is better than young WG because just what I have mentioned before they knew how to satisfy their client. Moderate to Rough anal sex can be used with WG by multiple positions like doggie. Of course use of ky is important. Some WG told me they eager for anal sex with their private even they do not offer anal sex at works. If you are talking about safety, anal sex with condom and ky may in some degree higher than CIM.

Do have an open dialogue with your gal for anal sex or asking the WG