My sitter. [MF] [MM]

While I have been sexually active since a very young age, the first time I was in a position that brought out and aimed me at being a sub happened when I was very young.

My love of spanking happened when I was very young, although my dad would spank me before he and mom divorced, my real awaking happened later.

It started when I was a young teen.
My mom would go on week long trips for her work and leave me with a sitter.
Her name was Linda and a freshman in college.

She would always wear these really short skirts and I was always catching a glimpse of her underwear.
One day she caught me looking but said nothing.
The next day was the same but this time when she caught me looking she told me I was going to be punished.
Like any young teenage boy and being the brat that I was I told her there was no way I would let that happen.

It was at that point that she pulled me up by my arm to my room.
Where she yanked down my pants and underwear pulled me across her lap and started to spank me.
At the first blow I let out a Yelp.
“Don’t be a baby.
I’ve only just begun.”
She said.
Over and over her hand came down upon my bottom.
Each stroke landing on a different spot on my bottom.
I could feel the heat this spanking generated.
I couldn’t tell you how many blows she delivered.
Although it was somewhere between twenty five or thirty
She kept at it getting harder and harder until my buns were flaming red.
All this time my penis was rubbing along her leg.
As this was happening I got harder and more aroused.
This rubbing had the expected results and at some point I shot all over her leg.

Standing me up she had me go over to the dresser with my pants and underwear still around my ankles get a tissue and clean her up.
After that she would find any reason each day to spank me.

These spanking took place almost every night after that.
This continued for the entire summer when my mom would have her sit for me. (Which was at least
twice or more during the week.)
Her spanking me made way to her teaching me about sex.
She gave me my first Bj and my first taste of pussy.

One day we forgot that my mom had given her boyfriend a key to the house.
While in the midst of one of these spankings we did not hear him come in to the house and climb the stairs.
As he followed the sounds he discovered her spanking me.
As I lay naked across her lap my bare buns in the air.
Telling her to stop, he yanked me off her lap and made her stand.
Telling her to stand on the side of the bed while he took over the spanking.

After that day my moms boyfriend found many reasons to take me over his knee or lay across the bed while he would either spank me bare handed or use some other implement, his belt or paddle etc.

After awhile he began to push his fingers into my bottom while spanking me.
He would work his fingers in and out of my bottom.
This had the effect of getting him (and me) hot and worked up.

As he was spanking me he would reach under me and play with my penis. This of course had the predicable results of causing a small boner, which he would keep stroking while he continued spanking my bottom.

He would keep stroking my penis and working his fingers in and out of my bottom until I couldn’t stand it any longer.
When I finally came he would stand me up, clean me off and send me to bed.

Many years had passed while the memory was still in my mind, my need and craving for such discipline still remain, I had often thought about pursuing it but never did until much later in my life.

Source: reddit.com/r/eroticliterature/comments/eim8kb/my_sitter_mf_mm