Always expect the unexpected. I’ve said it before and I will continue to say it at every given opportunity and especially after taking any of my subs by surprise. When Slave Sissy Mouse gave me a request (something that he rarely does) to dust off his school boy outfit, I knew what he’d be expecting from the session and so I put another twist on it. Actually I gave the session more twists than a Curly Wurly bar. I never cease to amaze myself with my ingenious creativity when it comes to roleplay sessions. I decided that this session would begin the second Mousey walked through the door, even if he didn’t realise it.
The bloody bath brush challenge.
My latest visit to Mistress at the House of Deelight was unusual because I knew what was coming and what the theme would be because I had requested it and set myself up for a hard time in the process. What I forgot was I’m not very experienced in role play whereas Mistress is very accomplished in such things and put me on the spot from the moment I walk through the door.
For this visit I had requested that I dust off the schoolboy outfit that Mistress had instructed me to buy for a cp session back in August 14. I can’t remember the details of that session but what I do know is it was nothing like this one. On my way to the HOD Mistress messaged me to inform me to change in the small hallway and knock on the entrance door. This leaves you with just a full frosted glass door for privacy. I arrive early to calm my nerves a bit and wait by the local Tesco, usually in case Mistress has any last-minute item requests, and wait for the clock to tick around to 11am. With a couple of minutes to go I drive off and park near to the HOD get my stuff and enter the open door. Immediately I am met by Mistress’s voice asking me if I got her text message? I ask if it’s the one about changing in the hall way and it’s not. The message Mistress sent me (which I received at 7pm that evening, nothing like technology letting you down) said Buy an A4 pad and for every minute you are late will result in 1 stroke of the cane. I stand frozen in the hall waiting for Mistress to then say ‘oh don’t worry’ but the reply I got was ‘that’s one stroke already’. With that I get my bumbling self to Tesco and I hate to admit it in a piss to the point where I almost just got in my car and left! What my bumbling brain had not worked out is the session had started already. Mistress had started the roleplay by making me late and as such a valid reason to punish me. Luckily, I found a pad, paid, returned to the HOD, got changed, took a deep breath and knocked on the door as instructed.
When (Head) Mistress opened the door, what happened next completely caught me out. I wasn’t expecting Mistress to grab me by the ear and drag me in front of the school desk tell me to pull my trousers down and bend over it. I didn’t expect Mistress to tell me I was 14 minutes late, I didn’t expect Mistress to cane me so hard that I got myself in such a state that I stopped counting at 4 and Mistress carried on until 6 with me whimpering and begging her to stop.
This is not how we start sessions, we start sessions with me being tied somewhere to relax from the outside world and have a nice chat before being left alone.
Mistress told me to calm down, control my breathing and because I had stopped counting, I was still getting the 14 from the beginning and every time I stopped counting she would start again. I composed myself and Mistress started again with no let-up in the severity of the strokes until I counted to 14. Mistress then told me to pull my pants and trousers up and chastised me for the pink panties I was wearing and the pink stripy tie which was clearly not school uniform. I just stood there with my head held in shame still trying to get my head around what was happening. Mistress then went on the tell me that I was just a closet sissy faggot and that I had been sent to her for touching my male peers inappropriately. I was feeling so utterly small and humiliated that I thought I might start to cry! (Head) Mistress then told me to pull the chair up to the desk, opened the pad that I had bought and instructed me to write the following “I must not touch my male peers inappropriately” and to continue to do so until I was told otherwise. With that Mistress left the room and closed the door. I sat there, wrote that line repeatedly with my mind a blur at what had already happened and I had never been more pleased to be left alone in a session.
I think I had reached line 115 when Mistress returned and sat very provocatively on the bench in front of me and enquired while my already terrible handwriting had got worse? I replied I was feeling slightly uneasy and trying my best to concentrate. I also told Mistress that I had brought her some offerings that were in a bag in the hall and that the dog had ate the apple I had got her (this earned me an extra 10 strokes for lying). Once I had reached line 134 Mistress told me to stop and put my hands on my head. This would be the number of strokes I would be getting plus the 10 for applegate. We then had a bit of a chat about this and that whilst my hands were firmly on my head (I do smile at the bizarre nature of a day in the life of Mistress).
As always Mistress after a while brings the chit chat to a halt and instructs me to put away the desk and chair and pull the whipping bench out into the position Mistress likes it. Mistress then instructs me to go upstairs and fetch the vibrating wand and return. On my return, Mistress invites me to place myself on the bench and straps me in. Once strapped in (Head) Mistress starts and it’s no nice warm up today,12 very hard whacks with the ‘beg for it’ strap and everyone made me wince. Once finished Mistress does something completely new she fires up the wand and starts working it into her pathetic cock until I reach edge. I try and last as long as possible to put off the inevitable hard whacks that will be coming my way once I reach edge. I have no defence against the wand and having reached edge, I then endure 24 very hard whacks with another implement which I have no idea what it was but it hurt and then back to the wand. Once at edge another 12 with another implement and then the wand again. This was a real struggle for me, I have never been whacked with this amount of force before and the stopping and edging wasn’t helping but that was what Mistress wanted.
Today was never going to be an ‘nice’ experience it was amount testing and pushing me!
This repeated several more times until and I was just about coping when a terrible thing happened at the next round of edging after I had begged Mistress to stop I felt the inevitable feeling of what was the worst case possible, I orgasmed. A massive gushing ruin that spelt disaster for me because now Mistress informed me I would not only have to endure post orgasm punishment but also post orgasm torture. The next 12 were difficult and there was still more to come. Once those 12 were finished it was the wand again and that on Mistress’s very sensitive cock made me squeak repeatedly but worse still it was starting to get hard again just to punish me even more.
It was just after this where the wheels almost fell off the session, Mistress got the cane out again and we had reached number 9 when I suddenly felt sick (because I was not regulating my breathing and getting in a panic) and with all the clothes on I was overheating and sweating. Mistress stopped, released me from the bench and with the clothes removed and a short break (including the offer of water which I turned down) it was back down to accept the rest of my allocation. With a very determined ‘9 thank you Head Mistress’ it was the final 3 strokes of the cane and then the crescendo 24 of the bath brush (12 on each cheek). I have been whacked with this before but never with the same vigour and determination that Mistress had that day. Once it was over Mistress had achieved her goals, which was to get the bath brush very bloody (tick) and to put me through a very challenging session (tick).
I was left shaking with adrenaline and I am truly grateful to Mistress for putting me through a very challenging session. After I had calmed down and felt able to stand I got dressed and cleaned up the mess I made (which luckily Mistress didn’t make me lick up as she threatened when I had the accident). We ended with a nice chat and Mistress insisting I look after myself and contact her if I have any adverse reaction to the session (which I haven’t) and then it was time to return to the real world. I must say I felt very odd for the rest of the day and a very early night beckoned. It was the next day that I could really grasp the full enjoyment of the session and marvel at Mistress’s skill in not only her craft but her incredible role play abilities and treating me to another ‘I wasn’t expecting that’ sessions.
Click here to contact and submit to your Mistress.
If you'd like to leave a comment, click the 'comment' button just below the title of this post.
Subscribe to missdeelight.com for all updates including stories, pictures and videos Enter your name (optional) and email address then click subscribe!