Okay, from a guy perspective, I love doing anal. Is it because of the taboo thing? Probably somewhat. But it also feels so damn good! Mostly, I've been the penetrater, but lately I've also been getting the urge to get fucked myself. I've never been able to stimulate my prostrate from the inside (had my partners' fingers and a dildo up there before to try it), but I'm hoping someday to find out what it feels like.
Anyway, orgasms from anal.... do you get them? how do they feel? same/stronger/weaker/different than vaginal/clitoral orgasms? My experience has been that there are a lot more women that enjoy anal than people would think. I know it's not for everyone, and that's cool too. But here are some of the things I've done that's helped to result in orgasms (sometimes multiple ones) from my female partners....
Let her set the pace, and pay explicit attention to her, what you're doing, and how she's reacting. In order for it to be good for you, it has to be good for her FIRST.
The way I tend to start off is when I'm going down on her. I use my tongue/mouth on her clit, the fingers from one hand to massage her G-spot, and take a finger from the other hand (lubricated) and just start by gently stroking and making circles around the outside of the anus. Eventually, I put a subtle amount of pressure on the anus while massaging it in a circular motion. My finger is not pointed in towards her ass, but actually the pad of the fingertip (where your fingerprint is) is what makes contact with her opening, and usually the tip is pointed towards the vagina.
With subtle pressure and circles, and plenty of lube, eventually her anus relaxes and the end of the finger starts to enter her ass. As this does, I start to reposition my finger so it's pointing into her ass. The motion starts to change to more of an in/out than circular motion, making sure that it stays well lubricated. As she loosens up and takes more of my finger in, I position my hand/finger and move it in a direction that follows the natural shape of her rectum (so I am not stretching her anus too much or poking her inside). I slide it out, relubricate and slide it back in periodically. If she loosens up enough, I will introduce a second finger. If it's too tight to fit a second finger inside, then I just let the other finger or fingers rest against the outside of her anus, rubbing it.
When she feels ready, we can choose several different positions (whichever is most comfortable for her). She can be on her back w/her knees pulled up towards her chest, rubbing her clit with one hand. Or she can be on her side, with the leg not on the bed bent and the knee pulled up towards her chest. Or on her hands and knees with her ass angled in such a way that my cock will follow the natural shape of her ass/rectum. Or (my favorite), her lying on her stomach, legs together, with me lying on top of her, supported by my elbows and knees (which are straddling her ass).
I then make sure more lube is applied in and around her ass, and a lot on my cock. I hold my cock by the base with one hand, rub the tip in a circular motion around her ass w/subtle pressure while massaging her clit with the other hand (or she does that herself). I add just a little more pressure while making the circles smaller. Then (very important) I have HER start to slowly push back against me until the tip slides inside. Usually (unless she's loosened up or pushes all the way back onto me), we stay in that position for some time until she's comfortable with it and adjusts to it being inside. Then she slowly (with my help pushing if she wants) pushes more back, and we both rock as its slides in and out deeper and deeper until I'm all the way in. I let her set the pace in terms of movement (fast/slow, deeper/more shallow penetration, harder thrusts, etc.). I also try to simulate other areas of her (neck, nipples, ears, clit, thighs, breasts, collarbones, etc.).
The key is lots of lube, lots of time, let her set the pace. Sometimes, I'll just massage her anus, and the following times we have sex we'll add a little more. Sometimes we'll do everything. WHATEVER SHE WANTS is fine by me. If she wants me to rim her, I will (works best either in or just out of the shower). The big thing for me is: getting her off turns me on.
I've found that when done properly, anal stimulation/sex can be incredible. One previous GF had hated it before me, b/c the two times she tried it with her ex before it hurt like hell. But after we tried the above method, she started having orgasms before I was even all the way inside her, and she also has multiple anal orgasms. My last ex completely swore it off before we hooked up as she was raped (sodomized) many years before. She was willing to give it another shot, and the first two sessions, the only thing I did was rub her anus during oral and rim her on a second occasion. The third time around, she came from oral w/my finger in her ass. The forth time, she had multiple orgasms when we finally had anal intercourse, and now she swears she can come from anal stimulation alone and her anal orgasms are stronger than any other types. The last time we did anal, she actually passed out after her 3rd orgasm in a row.
Anyway, just thought sharing our experiences might be helpful to others....
PS: remember, Lube, Patience, Let her run the show....
PPS: Safe sex: if you use condoms, use a water based lubricant (and lots of it) if you are using latex condoms. Oils will start to dissolve latex condoms...a BAD thing.
If you choose to go bareback, just remember that besides the disease issue, if you come in her ass, there is still a small possibility she can get pregnant if your cum leaks out of her ass and drips down and makes contact with her vaginal opening. Be extra careful when you withdraw after cumming that she is on her side or in such a way that gravity will not cause any leaking cum to run down into/across her pussy.