I suppose even with someone who is as sexually experienced as me, there is still a first time for everything.
One night, I had the hot idea of inviting this gorgeous Naval Officer up that I had met in San Diego for a night with me, and he agreed to come up.
When we start fooling around, he was the first one to dive into foreplay. I'm on my hands and knees while he's going down on me and at some point or another, decides to stick his fingers inside. I end up on my backside and about twenty minutes into it, he's still fingering me but at some point he had slipped in an extra finger. I LOVE being fingered as that is the easiest way to get me to climax and he had just the right hands for it. So about another ten minutes go by and I have my 5th orgasm (not joking) and he has managed to slip an extra one in there.
As time went on, my screams got louder and eventually went from being screams of joy to screams of pain without my realizing it. I finally thought, "This really isn't normal for me to be screaming like this." Even HE was trying to get me to shut up. I look down and I don't see any free fingers, so of course I have to ask.
"Dude, what are you doing?"
"What? Ah've got muh entar fist in thar!" (he's from the South)
"WHAT? NO NO NO NO NO! STOP!"
He withdraws, continues going down on me, then REINSERTS four fingers back into my birth canal.
"Oh, that's so hot, baby. You know you want this."
"NO NO NO NO, I DON'T WANT THIS!"
And in between the "no no noes," I manage to climax again as he had reinserted his thumb in between my fleshy walls and his inner palm. He went deeper.
"OH MY GOD, STOP."
I was freaked out. I had never been fisted before.
"You sure you want me to stop? You sound jes' like yer enjoyin' it!"
"STOP, JUST STOP. OH MY GOD."
We finish our foreplay and get to the dickin' (which was actually quite delightful as I came about another three times). After we're finished, I had to ask him.
"So, how far in did you get?"
"Oh, about this far."
He makes an elongated left fist and demonstrates how far in by cupping his right hand just a half inch above his left wrist.
I was in pain for many days after that.