Castigation22
28-09-2018, 06:38 PM
I recently had a wonderful session with my friend Alan, that will be the last for a while as he is moving to the South coast, and I live in Manchester. As it will be our last session for a while, we made it a good one, with all his favourite bits!
He likes me to cross dress as a schoolgirl, although I look ridiculous in a short blue pleated skirt, thin white knickers, knee socks and a short sleeved blouse. The scenario was that he was a teacher who found me with a boy, and I was sent to his study for a spanking.
It started with an over the knee spanking, the first few spanks across my skirt before that was flipped up and my knickers were spanked. This was not too hard, until he took my knickers down and spanked my bare bottom long and hard. His favourite target is the sweet spot at the junction of my thighs and bottom and he was already making me wriggle and yelp.
A few minutes standing in the corner with my skirt tucked in my waistband and my knickers at knee level left me quite exposed. I then had to stand beside him at his desk and his left hand gently stroked my bottom as he wrote in the punishment book. As my cock became erect (Gee, what a surprise!) He looked shocked and told me I was a naughty girl. He wanted to know if this had happened when I was with the boy, and I had to show him what I did. So I gently stroked his cock, through his trousers and felt his erection. For being such a naughty girl, I was given a dozen hard smacks with a ruler.
Then I showed him how I slipped my hands inside the boys trousers and stroked his cock through his pants. I got 12 with the slipper.
Then I showed him how I slipped my hand in his pants and stroked his cock. I got 12 with a leather paddle.
Then I showed him how I took his cock out of his trousers and stroked it. I got 12 with a wooden paddle.
Then I showed him how I knelt in front of him and kissed his cock. I got 12 with the tawse.
Then I showed him how I sucked his cock. I got 12 with the cane. Then he told me to show him that again, and I got another 12 with the cane. And we repeated that a few more times!
I was reaching my limit by this time, and Alan likes to make sure I am taken a little way past my comfort zones, and also that I pay for my pleasure. I was caned until I said that I had had enough, and was given 12 more hard strokes of the cane, and then 6 more on the sweet spot. He then gently stroked my cock until I was at the point of no return.... and stopped stroking. Curses, a ruined orgasm! I was then given yet another 12 of the very best with the cane before I knelt before him again and sucked him until he came in my mouth with a little sigh (or two!).
My cum was then mopped up with my knickers before I had to put them on and drive home with sticky knickers and an extremely sore bottom. I was certainly reminded of him every time I sat down for the next couple of days.
I will certainly miss our sessions, but I hope to visit him next month.
He likes me to cross dress as a schoolgirl, although I look ridiculous in a short blue pleated skirt, thin white knickers, knee socks and a short sleeved blouse. The scenario was that he was a teacher who found me with a boy, and I was sent to his study for a spanking.
It started with an over the knee spanking, the first few spanks across my skirt before that was flipped up and my knickers were spanked. This was not too hard, until he took my knickers down and spanked my bare bottom long and hard. His favourite target is the sweet spot at the junction of my thighs and bottom and he was already making me wriggle and yelp.
A few minutes standing in the corner with my skirt tucked in my waistband and my knickers at knee level left me quite exposed. I then had to stand beside him at his desk and his left hand gently stroked my bottom as he wrote in the punishment book. As my cock became erect (Gee, what a surprise!) He looked shocked and told me I was a naughty girl. He wanted to know if this had happened when I was with the boy, and I had to show him what I did. So I gently stroked his cock, through his trousers and felt his erection. For being such a naughty girl, I was given a dozen hard smacks with a ruler.
Then I showed him how I slipped my hands inside the boys trousers and stroked his cock through his pants. I got 12 with the slipper.
Then I showed him how I slipped my hand in his pants and stroked his cock. I got 12 with a leather paddle.
Then I showed him how I took his cock out of his trousers and stroked it. I got 12 with a wooden paddle.
Then I showed him how I knelt in front of him and kissed his cock. I got 12 with the tawse.
Then I showed him how I sucked his cock. I got 12 with the cane. Then he told me to show him that again, and I got another 12 with the cane. And we repeated that a few more times!
I was reaching my limit by this time, and Alan likes to make sure I am taken a little way past my comfort zones, and also that I pay for my pleasure. I was caned until I said that I had had enough, and was given 12 more hard strokes of the cane, and then 6 more on the sweet spot. He then gently stroked my cock until I was at the point of no return.... and stopped stroking. Curses, a ruined orgasm! I was then given yet another 12 of the very best with the cane before I knelt before him again and sucked him until he came in my mouth with a little sigh (or two!).
My cum was then mopped up with my knickers before I had to put them on and drive home with sticky knickers and an extremely sore bottom. I was certainly reminded of him every time I sat down for the next couple of days.
I will certainly miss our sessions, but I hope to visit him next month.