I've been fortunate enough in my past to have been involved with some wonderful girls who were inclined to be sex fiends. One of them, I could get off an absurd number of times just by poking around in her vagina; the other, would require minimal amounts of foreplay and then penetration to get off. And, I found myself to be a pretty great fit as far as size goes for both of them.

Well, about ten months ago I started dating this girl who was considerably taller than me (I'm relatively short; 5'5" - and she's about 5'9"). We have a pretty great relationship. I was her first about 5 months ago... and she's never really had a strong sexual appetite apparently. She masturbates rarely and has never been able to get herself off. When we first started having sex (first two months or so), about five to ten minutes in she'd hop off, lay down, and tell me she was in extreme discomfort. This didn't bother me other than the fact that I would always have to ASK her to finish me, which was frustrating... but that has changed and is no longer an issue.

Anyway, the current issue is that I still haven't been able to get her to orgasm. At first I thought (and of course, this is devastating) that I couldn't fill her up properly. I think she has a slightly more spacious vagina than average. So I started to go down on her more often. I've been praised by several women for my oral sex skills and was pretty confident that this would work on her. Nope. In fact, she'll moan a little bit and then later seems to be in a relatively calm and unaffected state while I'm down on her. So, that didn't work.

I have to treat her, both with tongue and fingers, extremely gently until she's completely worked up. She's come to enjoy sex. She says penetration is far better than oral or fingering, so that's just what we stick to.

I love her a lot, but I'm starting to feel really insecure about myself and I don't know if this is a healthy relationship for me to be in. My main problem now, I guess, is that during sex there is a period of about five minutes that I work her toward what sounds like might be an orgasm. Around the fifth minute or whatever it is, she'll moan and tremble and I feel quite happy with myself for being able to make this beautiful woman moan for me, blah blah blah... and then... there's just a complete drop off point. The moaning stops... her vagina gets incredibly wet, and the rest of the experience is not so pleasant. It has come down to me just pounding away to finish while she experiences little pleasure.

Some observations I've made is that there's FAR less friction after this drop off point. She gets really really wet and gets wider inside. I know this is natural, but it makes me feel insufficient for the first time in my life... so is there anything we can do to get her to tighten up a little again after this point for more contact?

And it's not like it turns into an expansive and dark cave where there's no contact whatsoever. I still feel myself touching her everywhere... but there's a really thick mucus-y layer over everything and it gets a bit wider. And if friction isn't the issue, what the hell else might it be? I try to keep in mind that she can't get herself off and that going down doesn't work on her.

Perhaps stopping entirely when she starts to reach that drop off point (somewhere during the moaning and groaning) and letting things settle down and refresh a bit?

I don't know.

you should ask her to give you dOm3(haed)

She gets me to bust nutz every time now. That's not the issue. I can't get her to bust.

As i once learned from a reall casanova......with a small penis

The art is to find the positions where it's tight anyways. If you cant think 'm up yourself, GOOGLE

If this fails, there's always the buyin a vibrator and pushin it against her clit from the drop point off...

eat her out, find that magical clitoris my friend...

Before the people you were with were faking, you are a pussy.

Alternately, she is too tense, needs lots of foreplay, or had a bad sexual experience.

The 'drop off point' sounds exactly like she's having an orgasm. She gets really into it, heavy breathing, moaning and all that, then all of a sudden is way wetter and the touching isn't pleasant any more? Are you sure she knows what an orgasm feels like?

Maybe she has weak orgasms? Do those exist?

She hardly reacts to oral sex. I know well enough how to generally get a girl off through oral sex and she truly, in comparison to the other girls i've been with, must be sexually dysfunctional. Gets her nowhere.

Absolutely. You should have her do Kegels regularly; she'll strengthen her muscles so she'll have stronger orgasms, and she'll be tighter for you.