You just can't use it with other silicone toys or condoms, so that may be out for you guys. And play around with angles and positioning -- there's a big difference between leaning forward and back when you are on top, for example, and equally big changes in every other position from minor differences in approach and angle. This early on, he may not be able to recognize that level of nuance. Be enthusiastic but not insistent, until you two settle into more of a comfort zone with each other. And if he's not, that doesn't necessarily mean he's not into you. I'm a female who dates tall men who've got big penises.
If it's really easy to get him up and running, that doesn't necessarily mean he's aroused or emotionally connected. This is probably a bigger aid if it's girth, rather than length, that's the problem, but for both cases: So shortness matters for certain sexual positions, but isn't any iron-clad predictor of size-compatibility. As some above say, it's more about angles and your own level of relaxation than lubrication. It is really only a partial aid to the problem some of the time, but when you are dealing with tight fits, every little bit helps - that is, while any girl can chafe at times, you've got ahem a bigger problem than most. If he's new to the sex thing, getting him to calm down and take it slow and easy can be tricky. I know for myself it took a lot of bad sex before I could start separating out all the different sensations and figure out how to be more in control of myself. As the more experienced partner, you have the luxury to set the tone. You just can't use it with other silicone toys or condoms, so that may be out for you guys. Lubrication only helps if you're having friction discomfort, which is different. It is also fun to use in the shower. See, the best sex happens when you learn your bodies well enough to take the safeties off and go a little wild. Missionary should be fine, as long as you don't let him wrap his arms under your legs which would prevent you from pushing him away if things get too deep. Fingers first - one, then two, then three - can really help loosen you up. What lightweight but powerful laptop should I buy? Make sure you're working toward that, slowly, rather than finding a lukewarm "safe" level and staying there. You on top is easiest in that situation, in my opinion anyway. It's condom safe, a little goes a long way. Try different positions, go slow, and above all give him feedback both good and bad while you're going at it. Being on top is the obvious answer, but you can also limit his range of motion and therefore depth using your legs in other positions. The wedge pillow idea is a good one; you want your pelvis on the high part and your shoulder blades on the low part, and go from there normal pillows work well too, provided they're not totally shapeless. Let him know that no matter how he comes - oral, vaginal, in your hands, in his - it's all cool, hot, and exciting to you. The stereotype is that male sexuality is simple and straightforward, and it often is. And regarding the positions, I'll just echo that you want to leave yourself some measure of control. Be enthusiastic but not insistent, until you two settle into more of a comfort zone with each other.
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