Take it easy to start. I generally start with a finger, then two, then when I can stretch the 2 fingers some I'll start with my cock. Even then it's not a slam bam thing, Take it easy getting inside. Loosen that muscle up slowly and your time in there will be much more enjoyable for everyone. Once it's loosened up, if your partner is ok with it you can pick it up. This time Jackie wanted me to pound her harder after we got going, "yes ma'am" as I gave it to her like she wanted.
So while you always read about me and getting my ass played with you don't often read about us playing Backyard-BBQ with Jackie. It's not that she doesn't enjoy it, she'll cum all over the place as we play, in her case it's the repercussions the next day.
Let's face it, when you're playing with someones ass there are several things that can happen -
1) You can aggravate an existing hemorrhiod, or for that matter create one if you're not gentle enough starting out. No one needs anything to do with that. Bleeding, pain, etc are not what anal play is about.
2) There's the STD issues that seem to be worst in anal play. The ass is definitely more sensitive to rip/tear and exposed to the STDs.
3) If you're prone to stomach issues, like Jackie, you would have repercussions in the bathroom later. In Jackies case she winds up getting backed up and it takes her a painful day or two to get relief. For others it might cause just the opposite issue.
How to prevent most of that? First us lube and lots of it. If you think you've got enough lube then add more and you might almost have enough. There is just no such thing as to much lube when playing with an ass.
If you're not monogamous and know it's 100% safe, put a fucking condom on!!! There is no reason to pass anything to or get anything from your partner over pride, or some lame ass excuse. Use a condom and stay safe.
Now there is a lot of reasons for anal play in my books. One the rectal muscle is just super freaking tight. Ok, Jackie is so tight that she'll push me out of her vagina, but the anal is a different tight of tightness that I love.
After taking pictures all day I asked Jackie if she might be up to it, and oh yeah!! I got the green light.
Lots of lube, take it easy to get started, then it was Katy bar the door as we went after it. I know Jackie would do it more if she could, her orgasms were amazing and she was floating when we were done, but repercussions just prevent it from happening all the time.
Hope you get to enjoy a backyard bbq on occasion, and take all the necessary precautions to make your partner enjoy it as much as you do.