Sideways sex issues?

My boyfriend and I have been together 9 months and during these 9 months we have tried to have sex sideways. But every time we try he keeps slipping out or feels he isn't going deep enough so he gives up and we do it in a different position.

I am more than happy with having sex with him in other positions but it's becoming really frustrating for me not being able to do it sideways. I really want to try it and we always get so close to it working but he just keeps slipping out.

I don't mind the fact that his entire penis can't fit inside when we do try sideways (is it all supposed to fit inside when trying sideways?) but I do think it frustrates him that he can't so gives up. There is a height difference between us (he's one foot taller than me) so I'm wondering could that be the cause? Is there a way to correct it? Any advice or tips is greatly appreciated!
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Most Helpful Guys

  • If you are laying straight, he has to try to get his penis between your legs. That is why it keeps slipping out.

    Next time, lay on your side, and bring your knees out in front of you. It will get your legs out of the way, and it'll practically be doggystyle laying down.

    • Quite correct. If the lady has her head at the pillow end, the guy should be almost across the bed.

  • You/him, have to adjust the position.

    You have to arch your back more and to give him a better angle and it less the amount of ass in the way;-) He could also move down more and come up from a lower angle. Basically think of as more of a doggystyle on your side.

Most Helpful Girl

  • Sideways sex is for movies. It does not work out in real life.

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What Girls & Guys Said

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  • We have the same issue and my wife has to change her angle of her body to mine to represent something like the letter "K" so it fits better.