Sassy Samantha

Sassy Samantha

As I made my way to Branch Place I wondered how I would find Samantha. I knew she was going out for lunch with her good friend Carrie and I just wanted to give her a big hug and sit down for a few minutes for a drink and a chat. Play time would be a wonderful bonus but only if Samantha was 100% up for it.

I telephoned when I was 5 minutes away and arrived to find the door already open. Samantha greeted me with a glowing smile in a lovely little black dress and we enjoyed a wonderfully warm embrace. She offered me a drink and we went into the lounge. As we talked she was far more cheerful than I had any right to expect so I asked the inevitable question. “Of course I’m up for it!” she replied. “Would you like a role play?” We decided on the young lady visiting the Headmaster who lived next door hoping to relive some of the punishments she had secretly enjoyed back in the day.

The role play

Samantha peeped round the door with a cheeky smile on her face.

“Are you home alone?” she asked. “Yes” I replied inviting her in. “It’s lovely to see you but to what do I owe the pleasure?”

“Well actually I’ve been very naughty and I deserve to be punished. I know it’s not allowed now but I used to get spanked at school. Did you ever spank a student?”

“Occasionally when they deserved it” I replied, trying to hide my embarrassment.

“On the bus I let a boy put his hand up my skirt and play with me in full public view. Would you spank me Headmaster? I’m sure you’ll agree I deserve it.”

She was totally unabashed and my embarrassment soon disappeared.

“If I do this I will do it properly.”

“I wouldn’t have it any other way” she replied as I sat down in the middle of the large settee and beckoned her over my knee. There were plenty of sounds of pleasure not pain as I rubbed and spanked her lovely bottom through her dress and then with the dress raised. I felt distinct signs of dampness between her legs.

“You’re enjoying this rather too much young lady. I need to use an implement”.

“I agree. Your hand needs rest Sir” she replied, finding me a paddle and obligingly bending over the bench. Neither of us felt the need to count and a couple of minutes later she admitted she was still enjoying her punishment.

“This time I deserve the plimsoll” she said. I suggested 12 of the best, which she took without a murmur and then raised her dress and asked for 12 more. Then incorrigible as ever she bared her bottom for 16 more to bring the total to 40. I felt sure she must have had enough.

Samantha disagreed. “We mustn’t stop yet. I haven’t had the cane!”

She placed 4 canes on the settee, 1 junior, 1 senior and 2 dragon canes. I was anxious not to give her too much and suggested 6 strokes with each in turn. She took them all with obvious relish and they made a lovely sound through her little black dress.

Surely that was enough? Absolutely not! Amazingly 24 became 48 became 60 then 70 then 80 and finally 100 strokes as Samantha kept offering me each of the 4 canes in turn. There were plenty of hugs and rubs along the way as we moved towards her target and by the time we had finished the atmosphere in the room was simply electric!

I left delighted to have found you so cheerful and upbeat. It was an absolute privilege to play with you Samantha. Thank you so so much. I hope you really do get well soon.


Dear Headmaster,

Many thanks. A joy to play with you again xxx

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