So it's going to be my first time doing anal in a couple of days, any tips to make it pleasurable the first time?
1. Make sure YOU want to do it.
2. Practice with fingers, small toys ahead of time to know what to expect.
3. Make SURE you want to do it.
4. Use plenty of lube. No, use LOTS of lube.
5. Start slow. Start with a finger, two fingers…if you don’t like it, STOP.
6. See 1 and 3. If you still say yes, see 2 and 4 and always follow through with 5.
Oh…make sure you relax. In fact, pushing ‘out’ a little as you attempt to insert anything (finger, toy, penis) will make it easier. Lube…don’t forget the lube.
Also, I would tell him to lay still and let YOU do all the work. Tell him until you know what it is like to have him balls deep in your ass, that you are in charge and will control the depth, the speed, and the length of time he remains inside you.
If he doesn’t like that, then pull out your best dildo, lube it up and tell him to bend over so he can tell you what it feels like.