yes, lubrication is a good thing. I suggest a basic water based like KY. Not the kind with the warming senstation tho.
Work her up. Put your pleasure aside for a while and really get her aroused then start incorporating you into it. If you can, try to stimulate her to orgasm before you attempt penetration. Go very slow and like little said, a little at a time. Kiss her and caress her the whole time. Put her focus on kissing and caressing you and accepting you in. Kind of a distraction like showing a kid a balloon while giving them a shot. She should be as relaxed as you can help her be and I agree, this doesnt happen in the back seat of a car. Position... her on top lets her control the action which may boost her confidence and help her get through it. Some pain is natural your first time...even first few times but excruciating pain is not.
Does she have some preconceived idea that sex will hurt? Like, did her girlfriends tell her it hurt when they did or they bled and it scarred them or whatever? Its not like this for everyone but if she does have an idea that it will hurt...then it will.




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was struggling with myself to stay out of it, not the best history there with that one for some of the same reasons.



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