I've been seeing the same woman for 6 months or so. She's great, in nearly all respects a real keeper. We are not yet exclusive, but both of us have been starting to consider making a commitment. I have a major concern though. Although I enjoy many activities, I have learned through past experience that my sex life just is not satisfying or fulfilling for me unless I have anal sex at least several times a month, and I honestly desire it even more frequently. This is a long way of telling you that failure is not an option.
I've asked several times to penetrate her tushy and she has agreed. However, despite my best efforts at making sure she is aroused, very well lubricated, and proceeding ever so slowly we have not been successful. She either becomes uncomfortable (apprehensive and embarrassed I think) as I warm up the area with a couple of fingers, or asks me to stop as I attempt to penetrate her, claiming that it is too painful.
I know that for a girl that is inexperienced, it takes a little practice to learn to relax, and that often initial penetration can be uncomfortable, but after the first few minutes it can feel intensely pleasurable, even leading to orgasm. I want her to relax, think of it as a sexy activity, instead of something painful, dirty, or embarrassing.
Also, she orgasms quite easily during masturbation, but has only ever orgasmed with a partner through extremely prolonged cunnilingus involving at least 10-15 minutes of silent concentration. This becomes painful for my jaw and tongue and because she can't break her concentration with an appreciatory moan, I'm totally turned off and often wondering if I'm getting anywhere by the time it happens. Any suggestions? I'm also concerned that since her G-Spot isn't easily orgasmic or possibly even sensitive, that anal sex may be less pleasurable, do you believe the two are related?
It sounds like you and your partner at off to a good start in your sexual endeavors. Contrary to the common belief that anal sex will always include some amount of discomfort or pain for the receiver, it can actually be a very pleasurable experience for all parties involved. Good anal sex must always include communication, a lot of lube, and plenty of time and patience.
While it looks like you are including all of these key ingredients into your practice, perhaps a little more of every piece is needed. Like I said before, communication is a must for good anal sex. For instance, how does your partner really feel about having anal sex with you? Or better yet, what does she think about anal sex in general? You say that in all cases she has agreed to proceed. However, does this mean it is something she is doing for her own pleasure, for mutual pleasure, or solely to satisfy you? Talking about her interests and concerns may help her understand what she is feeling, which in turn may promote relaxation.
You may also learn that anal sex just is not something she will ever be interested in doing. Just because you love it does not mean that she has to feel the same way. For example, maybe she enjoys cuddling and engaging in intense emotional bonding immediately after sex. If you do not enjoy this same experience, does this mean that you are going to do it anyway? Relationships require some degree of compromise, but these compromises may not always work out in your favor.
If she is willing to make that compromise for you, there are a number of things you can do that may make the experience more pleasurable for both of you. You said you already have some degree of foreplay (touching with fingers), what about including more? Using your mouth and/or tongue on/in/around the anus (also called Rimming) can be a very pleasurable experience. Including toys is also very useful before penile penetration. Start with one well-lubed finger, then two, and then move on to a small anal toy. Please make sure the toy has a flared base for safety. I recommend trying a small plug, such as the Bootie by Fun Factory. Once she is comfortable with this, you may also want to move to a larger toy, such as the Sidekick, or even a vibrating toy, such as the Pro-Touch. Vibrations can help to relax the sphincter muscles and may enhance pleasure.
Lastly, you may want to further educate yourselves on this topic. I recommend viewing the DVD, Tristan Taormino’s Expert Guide to Anal Sex. Tristan demonstrates the ins and outs of anal sex including preparation, foreplay, and penile penetration. The two of you can watch this together to learn more about anal sex, and you may even get turned on by the hot sex scenes included in this DVD.
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