Kendyll, im assuming your talking about %#@&#! sex?

There are some basics that I can give you before you try or explore that option.

I'm going to be absolutely blunt here at the risk of triggering someone so I am going to put a trigger icon on the post as well. I hope you don't mind.

Play in that area can be fun, for both. Personally for me, I don't enjoy much more than around the outside.. I don't enjoy penetration that way, but some very much do. It can be fun for men, but alot of men are very shy to approach it, thinking it makes them gay or that it means they are wussy boys ect.

Some basics before you start out -

START SLOWLY. If you rush and try to get things in there that are too large too quickly, its only going to hurt, and burn and sting and possibly tear tissue. The thing about this type of sex is that the tissue is MUCH MUCH more fragile than that of the vagina, or of the %#@&#!. So you need to be aware that things need to be somewhat gentler to be comfortable.

Another thing - its likely to be a little uncomfortable with penetration at first. This is ok - again, start small. My reccomendation is to get a set of dildoes that range from very small and skinny up from there. Start with the smallest, or even start with a finger, and get used to that before you move up. This gives the tissue time to stretch and become accustomed.

The other thing is lube, lube, lube, lube. I cannot ENHANCE THIS ENOUGH. If you don't use literally gobs of lube and its dry you are going to again cause trauma to the tissue. IF its something you are doing often, you can literally buy bottles of lube that are like a liter with a pump top. If your not into such a big bottle, I reccomend Eros lube - its silicone based and a little goes a long way. It is expensive however.

For the part of you doing that to him, if you both decide thats what you want to try - there is an area deep in there.. the best way I can describe this is the same as looking for the g spot in the female. If you feel around in there, you will feel almost like a harder area, this is the prostate and this is what they call the "a spot" in men. It can greatly enhance orgasms. but you HAVE to be gentle.

For yourself, personally from what I know, it works best with some time of clitoral stimulation with it. For me I never really got into it, but found it pleasurable to do it to others if they enjoyed it.

So the biggest things are lube, starting small, going slow, making sure its comfortable.

I hope that wasnt too graphic. Let me know if you need any more advice.