I have wanted this for my partner and women I share my bed with for most of my life. I believe when I unpacked it, it is due to the fact I have sensed that women have had to hold back and restrict their sexual appetites.
As I have personal experience in my current relationship of having to do this, I can say I both empathize and sympathize.
Now because I do like to ensure maximal pleasure in that fantasy of yours, the guys would start smallest to largest, because the little rag doll that is the women at the end will need to feel … oh my god that is bigger … and bigger and fuck me what the hell was that.
If she wins that battle, then I state you know what my dear …. let me lay down and you insert me in …. and the guys can start all over again …
In a funny ha ha to a sad political statement of no child left behind …. I would say no hole left unfilled for my partner ….. :)