Proprietrix
Posts: 756
Joined: 7/15/2005
From: Ohio/West Virginia
Status: offline
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Suggestions:
Have her go pee and empty her bladder before you get started.
Plenty of foreplay.
Blindfold her. A blindfold can be very powerful as more than just blocking out light. It can be that scrap of a shelter when someone is feeling exposed and vulnerable.
Put her in a comfortable position. (Probably lying on her back.) Use pillows to prop here and prop there. Tell her it is her responsibility to arrange the pillows so she is comfortable. Check in occasionally by asking "Do you need to switch the pillows around?"
Tell her that the goal for the night is for you to try different/certain things and learn her reaction. Let her know that the goal isn’t for her to have an orgasm, but the goal is for her to be honest about what feels good so that you can know her body.
Set the rule: No faking it. A lot of women who can’t orgasm, feel the physical sensations and they feel very very good, but after a while they get so frustrated and annoyed with trying to achieve orgasm that they fake it to get the session done and over with. It’s not necessarily that they want the physical sensations to stop. It’s that they want the mental frustration to stop. Pushing through that frustration is kind of like pushing through being sleepy before you get your second wind, or pushing through mild cramps when exercising. It gets bad, but it does pass. Faking orgasm is the easy way out.
Let her know up front that you are going to be there a while. You may even set a time. "You’re here for the next 2 hours and 45 minutes, so you might as well relax and get comfortable." That takes some of the pressure off of her in two different ways. On the one hand, she’s not going to be thinking to herself "I have to make this orgasm happen because he’s going to get tired of doing this in the next 15 – 20 minutes. Come on orgasm. Hurry up and happen before he quits!" and on the other hand, if she still hasn’t reached an orgasm within an hour or so, she’ll simply "give up" on trying. Many women have found that when they give up trying, it just happens.
Gag her, or even better, flat out tell her she’s to be silent. Some women feel this obligation to moan and groan as a means of saying "Yes. I like what you’re doing." If she’s someone who mentally fantasizes to reach orgasm, that "obligatory verbal feedback" can distract the fantasy. Let her know that she isn’t to give you any kind of pleasure noises unless they are genuine and come naturally.
Feedback is important though. After the deed is said and done, and everyone is cleaned up and cuddling, then ask for feedback through direct questions. Which did you like better? The vibrator or my tongue? When I did XYZ, was I too high or too low? Which part was your favorite? Which part did you not enjoy at all? What do you wish I did more of? Less of? Do you like it better when I switch what I’m doing more often or less often?
Another night you might try a different tactic of doing one particular thing for about 10 minutes and asking her to rate it on a scale of 1 – 10. Then try something else and have her rate that one.
Keep in mind what you like. For the most part, orgasm is achieved in similar manners for both men and women, with subtle differences. A lot of people need a steady rhythm, with consistent pressure, for a certain amount of time, with lube. Fumbling around and alternating too often can cause someone to "get almost there" and then make them have to start completely over on building up.
Keep the whole Master/slave dynamic of you controlling her sexuality on the back burner for a bit. Many people believe that a sub/slave can’t hand over control they don’t have. She has to have control over her orgasms before she can hand that control over to you. The forced cumming, cum on command, refusal to allow orgasm, asking for permission before cumming, etc… really needs to take a back seat. It all just puts more pressure on her to "perform" when she’s already experiencing a road block in the bedroom.
Also keep in mind that a good portion of women can’t orgasm vaginally, only clitorally. Some need both types of stimulation. A good starting point might be to find out exactly what she does when she’s masturbating alone, and use a similar technique. Have her actually show you.
You may want to ask her what she fantasizes about while she’s alone, but I wouldn’t be a bit surprised if she doesn’t tell you. It may be the case that her fantasies are very taboo and on a subconscious level she feels that they are so secret that she can only have them when she’s alone. A better tactic than asking her to tell you the fantasy, might be to have her pick out 10 movies, or 10 pictures, or 10 magazines, that depict her deep fantasies. This kind of says "Hey. It’s ok to have that fantasy. See, 10 other people have it too." and you’ll get 10 points of reference. Find the pattern.
Tell her to not masturbate for a day or two before the two of you are going to try it together.
Then, a week later, go back to step one and repeat. Time, trial, and error.
It may be that she’s never able to orgasm with you. If that ends up being the case, please try not to take it personally. We’re all wired differently. If you do even the slightest things (like sighing in disappointment after a session when she couldn’t get off), she may very well resort to withdrawing her sexuality. Once that happens, it’s a very lonely place to be. Let her know that you love her and accept her for exactly who and what she is, with or without an orgasm.
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IMO, IMHO, YMMV, AFAIK, to me, I see it as, from my perspective, it's been my experience, I only speak for myself, (and all other disclaimers here).
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RE: Unable to orgasm except alone - 
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