joebear, I have found that when the woman (me) has an orgasm or two first, she will be more relaxed and it is MUCH easier and also very enjoyable. The technique is very different than vaginal sex. NO hard thrusting, and if you are big, probably don't put it all the way in at first. Also, many of us prefer double penetration, so a nice vibrator or dildo is helpful. (This also prevents the penis from accidentally ending up in the vagina or rubbing up against the urethra and causing infection.)
If you do it lovingly, and listen to her body (if she is TENSE, it will hurt and you NEED to stop) to guide you. Lube is necessary, but I don't agree with the "desensitizing" lubes, because if it HURTS you are doing it wrong, You should NEVER desensitize the anus or any other part of the person being penetrated. It it hurts, that can damage the anal lining. If it is done properly, and with enough lube, it shouldn't harm anything. The first time my dh and I succeeded (the first few were attempts, because I stopped him) and I really liked it, he just kept saying, "OMG, I love you, I love you SO much." Over and over and that love really made an impact. (he is usually VERY non verbal during sex. I mean, he's a guy.) He always asks first, and if I am uncomfortable with the idea (for various reasons) he doesn't press the issue. Also, he is careful to not let it go on too long. Often he is the one to say, "I think we need to stop, because I don't want to hurt you." if he hasn't come in a few minutes. He usually does come, but if he doesn't, it is NECCESARY to wash the penis if you are going to put it anywhere else. Either vaginal or oral sex after anal, without cleaning the man is really not a good idea, due to the bacteria that can be moved around. (I've had a couple of urinary tract infections and he once got something similar to food poisoning, and I think both were due to our lack of being careful if we switched up.) Now, I go and get a clean wash cloth, and use warm water with a nice, rinsing soap, and clean him up (I have never SEEN anything on there, but I know bacteria is there) before going on to other activities. If we are too lazy to do that, and it's been a while and he hasn't come, he just jerks off, and I talk dirty to him. It works for us. Usually, once we decide we're going to go anal, though, he's "done" in just a few strokes.......
I can be tolerant of almost anything....except Intolerance........and Dairy Products