after solving the storyline visit jenna in the wee hours of the morning. she will be asleep under the covers. you can strip off the covers and pull her to the edge of the bed and position her for whatever kind of fun you want. However, she does wake up quickly once you start. i guess that could be a new story line for this girl if you were to option her staying asleep or waking.

It would be fun to see how far exactly players can go without waking her.
I have managed to drag her around, accidentally banging her head on the headboard, dropping her unto the floor and twisting her into uncomfortable positions. And she still sleeps.
But one poke with the winky, and she springs awake.

Yes, she has a strange sleeping pattern

You just have to be VERY careful and sloooooooow..

Proof: Here and here