Stories with caring, encouraging, kind spanker and nervous spankee?

Negotiated Babysitter Methods, by Cherry Red in the final part has a description of a babysitter's mixed emotions as she realizes she is to be spanked too. For her part in the weekend, she is corporally punished along with the other girls.

I like that type of story as well. You might like my stories "A Whole Nother Story" and "No Good Deed Goes Unpunished".

'Waiting Ends - Paige's Turn' by the venerable Kilahara is an oldy but a goody. It was one I learned from when trying to start writing my own stories.

I've just sent Flopsy one - 'Journal of a Witch' - that comes roughly into this category.

Keep an eye out for it when it's posted!

Sir Cambornek

An oldie but a goodie is "The Talk" by ChardT, I think it is quite close to what you're looking for. The mother is fairly stern during the spanking itself but is very sensitive, caring, nurturing both before and after the spanking; the result is a close mother/daughter bonding experience.

It was followed by a sequel "A Deal's A Deal", plus if you enjoy these stories I think you will also enjoy the other stories he's written.

I very much like that dynamic as well. Though for me it's important that the spanking is then set at the right level: hard enough that the anxious spankee does feel they've taken a proper punishment and it wasn't all an anti-climax, but not so severe that it seems a jarring jump from the spanker's previous kindness.

WeddingBee
Does my new story, Margot Symthe grammar school tick the box for you?

Kane Strokes

You could try my "For Susan". Kind and loving mother spanks her generally good, but not on this occasion, teenage daughter for the first time.

Geoffrey Stirling.

There's a story called "Compassionate Counselor" on a different story site (not sure if I'm allowed to mention it here so I won't, but you should be able to find it either way), about a student who is sentenced to his first Caning, and is terrified. His fear prompts his teacher to send him to the female school Counselor, who guides him through the process, and also ends up giving him the caning.

I also enjoy stories like the ones you are looking for, and this one totally fits that scenario.

Kailee and Discipline for Good Children by Legion300 belongs on this list. It's part of the Zoey series, but can easily be read as a standalone.