miztig69, good that you are planning for your encounter.
i second what a few have said - communicate w/ the woman. if she knows what she's doing, she'll have plenty of advice and reassurance.
good luck!!!
a few nights ago, a woman used a lipstick diameter sized vibe on me while working over lil delites.
when it was first going in, it felt great. i could feel the vibe itself and the vibrations.
but after an inch or two in, i could barely feel the vibe and almost all the sensations were way muted.
she pulled it back to just be inside and it felt much better, dare i say deliteful ?
so, i second what zoey wrote - if my anus had been "numbed" or anesthesized, i prolly wouldnt have been able to feel a thing. and not been able to tell if it felt deliteful or not. kind of defeats the purpose.
the few times that a woman has used a dildo on me, we made sure that it and my anus were liberally lubed. unfortunately, for the next two days, my colon and anus didnt at all like the effects of the pre-session enema and all that action.
better to know than to jump straight in blindly.
to each their own.