Finger in the Ass

[Thought30]

Sammyfan's post above mentioned how the wife never was prepared for full on anal and that reminded me of this incident.

Maybe the 3rd year my (then girlfriend, now wife) and I were going out we were having sex in my living room one day and the phone rang. I picked up and it was her mom calling looking for my gf. I handed the phone to her but we keep on fucking--I thought it was amusing.
Anyway as the conversation went on, I stand her up and turn her around to start in on her doggie.
She is soaked at this point and as I am sliding my cock around to get into her pussy and, *pop*, the head is suddenly in her ass!
it slipped in so easy. I guess she was relaxed talking to her mom or something and that combined with the outrageous wetness made this accidental anal possible.
She didn't react in a negative way she just kept talking to her mom and I'm barely registering what's going on. I grab her hips and pushed in just a touch further and it hits me--this feels different.
I spread her open and see what's up and basically instantly start cumming in her ass. It was just too much!

She said it didn't even hurt her at all. we tried again another time a long while later and it was too painful so we never attempted it again.

Even since that event I will occasionally search for "accidental anal" clips and while most are fake the ones that are real are generally horrendous with lots of pain involved and I am not watching that.
There have been a couple of legit ones that end in pleasure and i find that incredibly hot but it seems like a one in a million sort of moment.

I was lucky.