I don’t understand why there is so much hype against anal sex. It constantly gets a bad rep. But I tend to like it. A lot. And with the proper preparations, both partners will find it pleasurable.
And preparations are important, even for an anal veteran. You need lube, a lot of it. Your ass will not lubricate itself, like a vagina. And use lube, not spit. Saliva won’t keep up. You may also want a condom, which is a must if it’s someone you don’t know well or has not been tested for STDs, as the lining of the rectum is much thinner than your vagina, so it is more likely to rip or tear.
Make sure you don’t bounce back and forth from pussy to ass, as this can give you a nasty infection. Always make sure he washes his junk if he’s switching back and forth. Or use a condom. Or something. This was a hard one for me to learn, as I really like going back and forth. But after a few UTIs, I finally started getting better at this.
Gradually working up to anal has worked well for me. During the first 5 or so years of our relationship, M and I had anal a few times a year. It was always a little painful and we would have to go really slow at the beginning. This would often deter us for a while, but we would eventually
always come back to it. I made the decision that I was going to do some thing about it, because I liked the way it felt, it just always took so long to actually enjoy it. We started engaging in anal play more often, with M using a finger while going down on me or while I rode him. Then I ordered a three set of butt plugs from extremerestraints. We stated playing with these, until I was able to wear any of the three (small, which is very small, not much bigger than a finger, medium, a little smaller than the “average” butt plug I’ve encountered, and large, which was a jump from the medium, but oh my, do I love it!). Now, with some playing before hand, and lots of lube, anal doesn’t hurt at all. Just all pleasure.
So if you’re interested in it, I’d recommend to do it. Be patient. Stay relaxed. Use lots of lube. And have fun!