Earlier in the thread someone made the comment about, "How many of you guy's were the GIRL'S worst time?" and it got me thinking...
As far as I know or an concerned, I am my second fling's worst time. (The story about the couch)
BUT
The first time I ever fingered a girl, the girl who became my first girlfriend, oh man.
She stayed over at my apartment, there had been some incredible flirting through the day. Sometime during the night she breaks the pillow-barrier I've made in my bed (because I'm a polite and innocent virgin) and we make out.
Making out leads to playing with boobies. Playing with boobies leads to groping her butt. Eventually this leads to my left hand rubbing on her vag through her panties. (I'm laying on my right side.) The panties move out of the way, and I'm fingering a girl for the first time! It is AWESOME.
But my hand hurts because this angle I'm at sucks. So I pull my hand out and go in from the front.
She stops me and repositions my hand, and I go back to work.
After a while we stop, I don't remember if she came or not (probably not) but I found out that, oh hey, when I repositioned my hand? I accidentally went too far and stuck my finger up her butthole! Whoops! That's why she grabbed my hand and repositioned it for me.
Hahahahaha oh God.