Our expert says:
The best positions for deep penetration would be either female superior (this might be tricky if she is a little heavy as she may struggle to support herself) or rear entry. You will just need to experiment with the angles that are best for both of you as these can also be uncomfortable too.
The question I have is, deep enough for what? If you are not getting enough friction for your pleasure you (or your gf) can hold the base of your penis to add depth to the friction for you. If it is for her benefit, whilst some women find deep thrusting pleasurable, the erogenous spots are mainly in the first 1/3rd of the vagina, so one doesn't need to penetrate more that say 3 inches for her pleasure and the added help of manual stimulation of the clitoris can help too. So unless she is looking for the deeper/cervical stimulation, it may not be necessary.
Claire - SASHA
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