Q. I want to have anal sex with my girlfriend. I read a few articles from your site about it, but I was hoping you could give me a more detailed explanation of what I need to do, or maybe explain what it is I'm doing wrong. My girl says it still hurts when I do it, even though I go slowly, one finger at a time, lube, and all that.
A. Ensuring that your girlfriend has a great anal sex experience boils down to two parts: firstly, her ability to feel relaxed with you; secondly, the technique that you use. Though her individual state of mind will have a lot to do with how comfortable she is with anal play in general, the methods that you use will be a big influence; so, let's zero in on them step by step.
You've got to have finesse in the bedroom if you want to roger her in the rear. In order for her to be primed for anal sex, she's got to be turned on - and we mean really turned on. Before even thinking about moving south you need to pull out all the stops, making sure to take your time as you … pleasure her clitoris using your mouth or a toy, then ... stimulate her vagina - either with a dildo, your hands, or your penis. If she feels pressure from you to move faster than she's prepared for she'll tighten up, so take your time!
Once you get to her back door, don't head straight in. Even though she's turned on, her anus still needs a warm up -a definite must. Analingus will stimulate the rich nerve endings located at the entrance of the anus, but feel free to slowly and gently rub around it with Anal Fingering instead. Even though these techniques can feel amazing, you'll magnify their effect exponentially by multi-tasking - another must; in other words, stimulate her other erogenous zones while you pleasure her bum.
When she's aroused enough to give you the green light, use a well lubed finger and go in about half an inch; now stay there! You'll feel her sphincter contract and relax in response to your finger. Let this happen without pushing any further. Get her rim used to different sensations like gentle twisting and slow pumping with and without removing your finger completely; she MUST get comfortable to this sensation, so DON'T rush the process. Since you're going to be here for a while, finger her vagina or caress her thighs, basically do anything that will distract her from thinking about what's happening in her rectum.
When she's given you permission to go deeper, ask her simply to 'push out', just as she would if she were to defecate. Insert one finger slowly, but not straight on. Instead, rest it on the rim of her anus closest to the perineum (the patch of skin between her vaginal opening and anus), apply light pressure, and when you sense her sphincter relax, gently insert. Repeat the process described above. Your next step would be to try two fingers or a flexible, non-porous Anal Toy. Why not see if she'd be into penetrating her own anus?
It's likely that you'll have to do this practice a number of times before even attempting penile penetration. When she's ready to go for it, apply the same principles as explained previously; in fact, the bigger the object used to penetrate, the more stimulation she'll probably need on her Erogenous Zones. You can do it for her but she might feel more comfortable getting off herself.
If you catch her taking shallow breaths, gently remind her to slow it down. Though it happens quite naturally as a result of excitement, it can negatively impact her ability to relax. Also, experiment with different Rear Entry sex positions. Some women love anal play while they're standing, and others while lying down on their sides or on their tummies.
Getting to the point where your girlfriend is comfortable with anal sex is going to take some patience on your part. She has to be able to trust you, which means that if she says, "stop", "pull out", or "I'm not feeling up to it", you'll respond immediately and with no questions asked. With trust comes ease and relaxation, and with that, a relaxed anus and pleasurable Anal Sex.