The headmasters schoolroom

I am a naughty natured BiCD with a very girlie outlook (if not very convincing).  I enjoy the feeling of being punished - spank/ paddle/cane etc, as it makes me feel more femme.

After a session with a dom guy he was chatting to me about just how much punishment I can take, and when it no longer becomes a pleasure.  I bravely told him that I hadnt found that point yet. Even when punished hard  I might cry but I don’t use the safeword.

A couple of weeks later I received a message on my phone to say that Tina  had been invited to the headmasters lodge for an interview. Couple of messages back and forth to make sure it was genuine found me 2 weeks later sitting in a hallway at very posh residence, having done as instructed and put on my skool uniform.

I was duly called into his room, a very traditional office with a leather topped desk, single hard chair in front of it, you get the picture.

Welcome Tina he said, you have been recommended as a naughty pupil that might benefit from a punishment and if deemed appropriate, you may be offered a place at our classroom.  The first thing we must find out is if you are able to handle our type of skool discipline. Are you willing to be disciplined young lady. (shiver  but of pleasure as he called me young lady). Yes Sir I replied. Step forward girl, and bend over the desk. I did so and automatically stretched for the far side – theres a good girl you obviously know the drill.  I am going to start with the traditional skool slipper – are you ready girl ?  Yes sir I replied. 6 firm hard whacks of the slipper onto my skool skirt – not a move or a sound from me.  I felt the skirt being rolled up my back. This time 12 hard whacks on my skool panties – still no response from me, I’ve had much worse. The I felt my panties being tugged down just to the edge of my cheeks and then he gave me 18 whacks with the slipper on my bare bottom – this did elicit a couple of yelps from me but no movement.

Well I can see Tina is experienced in being punished – lets see if we can get a few more yelps out of you girl. I heard the unmistakable swish of a cane then felt the cool rod resting on my slightly tender bottom. You know the counting rules Tina, fail to count and they don’t count remember to say thank you, oh and Tina, what is the safety system……… Yellow sir if its getting too much, and red sir if I want to stop.  Good girl was the reply, followed by the swish of the cane and a line of fire on my bare bottom … One sir, thank you sir, this followed 5 more times to make a set of 6, he changed sides, stroked the cane on my bottom and started again 7 sir, thank you sir, until 12 were delivered.

Tina, you are a very resilient young lady, 12 strokes of the cane, and no tears. I wriggled slightly on the table, and he then said – Tina, stand up girl, turn round and face me the back of my panties were still pulled down, but the front was still at waist level, staying in place due to my hard cock. He ran the tip of the cane gently over my cock that was trying to escape my panties.   It looks like this is more pleasure than punishment Tina. Blushing  I simply said Yes sir.

Right girl – next level then, this time touching your toes – take your skirt and blouse off, you may adjust your panties so they hold you in place. I chose to pull them right up very tight, still gives a bare bottom but captures  the cock. 

Now bend over girl, as I did I allowed my hands to brush over my bra, and promptly felt his hand  land hard on the back of my leg. No touching yourself girl – this is a punishment. 

Another six on each side – I was yelping now, it was on fire. But I knew I wanted more actually said, “Please sir don’t stop yet”, so he carried on with his cane on my bare bottom, after another 3 or 4 strokes I started to cry, real tears. Then it happened, my hands flew up to my tits and squeezed them hard, and I came in my panties – all wet and sticky. To his credit he stopped punishing me – Tina you are dirty little slut. Stand up, I was still sobbing a bit,  Go and stand in the corner and compose yourself – when you are ready you may come back to my desk.

A few mins later I returned to stand in front of him. Well Tina, despite my telling you that you were not to touch yourself you ignored me and played with your breasts.  Show me your breasts Tina – I scrambled to undo my bra and my cute little A cup tits popped out. Hmmm, sensitive are they my girl ?  Yes sir I replied. Put your hands on your head girl, And he picked up a suede flogger from out of hes desk drawer – he was the other side of the desk from me and as he flicked the flogger towards me, just the tips flicked against my breasts, just one strand caught a nipple, again and again, and again, oh I wriggled and squirmed yelped, it was a mixture of sweet sensation and stinging pain. At 18 he stopped – are you breasts sensitive now girl, Oh yes sir I whimpered. Touch your breasts again Tina, like you did before yes squeeze them, grab your nipple, how does it feel now girl. Oh, like nothing I’ve felt before sir – its lovely and sore and frustrating all at once

Well young lady, I think that you have well and truly showed that you are more than capable of handling our type of discipline. I am willing to offer you a place in the schoolroom. Classes are by invitation, with usually 4 students of varying ages, orientation, and dress sense, as far as skool uniform goes. Your invitation will include details of where and when the class will take place.  You must expect to be punished in full view of the other students – as they also will be.

I thanked the headmaster and gingerly pulling up my panties, and putting my skirt & blouse back on, then remembering to pick up my bra, and left his office. The memory of a significant punishment always remains, but it was 3-4 weeks later that I recieved a letter telling me that I was required to report to skool on a Thursday afternoon, and it included a dress code for girls and for boys.

The next story in this set will detail how that first lesson went.