I’m 48 and finally with the woman of my dreams. We’re in love and our life sex is outstanding. We’ve figured out how to make her squirt and she loves anal sex. I’m the first guy she did it with so it was a bit of a process.

Anyway, she’s been playing with my ass the last several months. She has always loved rimming me and she worked up to a couple of fingers and she has given me really intense orgasms.

But, we both know we’re just missing the magical spot in my ass and not getting my prostate to its maximum. Shes described her squirting orgasms and I think she almost has me there.

My problem is that we bought a slightly bigger anal toy (specifically made for prostate) and I can’t handle it. It’s not that the pain is unbearable but it literally feels like my ass is going to tear.

But, the pain isn’t that bad. It’s just a feeling like it’s going to tear.

We’ve been working at this awhile. She can get three fingers in if she doesn’t go to deep. I’m talking like an inch, lol.

I’m about to break down and try some numbing cream. I’m he heard nothing but bad things but I think it’s a mental block and just easing that tearing feeling will get us there.

She REALLY wants to peg me. She can have an orgasm without touching herself with anything in my ass.

I need advice. We both want this so bad.