I've posted this before, hope some of it's helpful.
Anal sex tips to help your girl enjoy it.
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Most women are afraid to try anal sex. Many who have tried it have had bad experiences that have turned them off anal sex completely. I hope that this will help make the experience a good one for both the woman and the man. Women...don't be afraid! Men...be patient!
I don't know what, if any, attempts you've made to enjoy anal sex, but let me tell you, it's absolutely wonderful. My most intense orgasms come from anal. Once you let yourself go, it's a feeling like no other orgasm produces.
Instead of the typical g-spot or clitoral orgasms, anal seems to combine the g-spot along with whatever other pleasure receptors are in the ass to produce mind blowing sensations that just go on and on, very deeply, very intensely, and for longer stretches than the usual orgasms. Most of the time when we're having anal, either my husband or I will also be playing with my clit and/or pussy using a vibe, a dildo or just fingers.
Positions ... three favorites of mine are: me on my knees with my legs spread fairly wide, my ass angled up towards him while my chest down against the bed, my husband standing behind me at the edge of the bed; me on my back at the edge of the bed, my legs spread in a wide "v" with my husband standing; me on my back on the bed, my legs spread in a wide "v" with my ankles at about shoulder height, my hips raised up naturally with my legs being so high, my husband on his knees either with his body erect or leaning over me. All of those positions allow us easy access to my pussy and clit for more stimulation.
Obviously lube is a must for anal (water based only if you're using a condom). You should begin to loosen her up with your lubed finger. Put a good amount of lube on your fingertips and gently caress her hole, applying a little pressure on the entire area, not just going immediately in. Play with her clit and/or pussy gently while you're warming up her ass. SLOWLY take one fingertip and massage her hole with little motions of going in. She needs to really relax her muscles or it's gonna hurt. Pain is part of the game though and the pleasure she will eventually receive will be well worth the moments of initial pain. Once you've maneuvered a fingertip in, say to the first or second nuckel, move your finger in a circular motion slowly loosening up the rim. It's kind of like a stretching exercise. Keep doing this and add in a little in and out stroking as she becomes more comfortable and is feeling pleasure from your finger.
Next I would go for a small vibe or dildo...very well lubed, and gently slide it into her ass. If she says stop, you stop. Don't pull out though. If you just leave it alone held in place, her hole will loosen up to accommodate the toy. Again, once she's comfortable, slide it in and out and in a circular rotation to loosen her up some more. You should continue to stimulate her pussy/clit during all of this.
You may have given her an orgasm by now.
When you both think she's ready for your cock, make sure you've lubed yourself up well. Just like with the toy...it will hurt unless she's completely relaxed so listen to her, when she says stop, you stop. I've had to have my husband stop and be still for a good 30 seconds due to the pain, but I KNOW how good it's going to feel once I can get beyond that. I think much of the reason I wind up in pain is that I'm too excited and simply can't relax my muscles well enough. Anyway, take her cues and go slowly.
Once you get past the head of your cock by about an inch, the rest will go smoothly, slowly, perhaps pausing for a while until it's all the way in. The skin in-between her ass and her pussy is almost paper thin...she will feel your cock hitting her g-spot. You will love how different her ass feels on your cock, so tight and hot!
After a little slow fucking, you will be able to fuck her ass harder and faster, sending her into some very deep and intense orgasms. One of you should continue to pay attention to her clit too...it's just absolutely mind blowing!!! Nipple stimulation is always a good thing to add in too. If she slides her fingers inside her pussy she'll be able to feel your cock with her fingers.
If she's very nervous about trying anal and she can enjoy a drink or two, this would be a perfect time, as it will help her relax. If either of you are worried about any possible mess, the man can just slip a condom on so clean-up is simple. For sanitary reasons, any toys or what ever has been in the ass must be washed well before going back into the pussy, a liquid antibacterial soap will work perfectly.
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