Well I can say this was a first for me and something I never expected to happen. I first met Mark at a Adult school role play event he was working as a waiter and very good at it he was indeed, as there were more than a few resemblances to Jeeves the Butler.
He was obviously a submissive and his need and desire to please was very apparent, at the after party in the evening I was approached by a friend who asked if I would be interested in giving Mark a spanking and although not totally surprised I was certainly not against giving it a go. I told him to bend over my knee to which he mentioned this would be his first spanking of this kind having usually been spanked flogged over some kind of apparatus bench etc in a more BDSM type environment, anyway I gave him a good long hard hand spanking on his trousers to eventually bare bottom, he was quite resilient and took it very well showing little emotion so I eventually moved to using a leather paddle and strap which seemed to extract a reaction. when id finished and allowed him up we had a customary hug and he said how much he had enjoyed the experience, so much so that we planned another meeting.
Mark arrived with a boxed cake treat for me perhaps he thought this would put me in a more pleasing mood to deal with him.
It had been agreed that he would assume the role of a whipping boy and accept punishment on behalf of my own submissive for naughtiness she had been up to during the week and deserved punishing for.
Mark is not naughty and does things to please rather than deserve punishment, but revels in the acceptance and receiving of the pain being inflicted by a spanking etc. Therefore this scenario was perfect for him to assume.
After an initial discussion and his acceptance of the punishment I put him over my knee and spanked him by hand from trousers to shorts to bare bottom. I then moved onto the tawse and several other implements and eventually ended up with him bent over a chair and gave him 24 strokes of my senior Kaboo cane then 12 with my Dragon by which time he had acquired a slight cut on his right cheek so I decided enough was enough and after treating this with an antiseptic wipe I allowed him to get dressed and the session was over.
Now Spanking adult males is not something im unaccustomed to, in my headmaster role I deal with several Adult boys, but Mark is a Transman in that he was originally a female lesbian but is now making the long journey to becoming male and although he is now after operations flat chested, he still by choice retains female genitalia.
I know this will not be the last time Mark visits me.
If you would like to read more regarding Transmen look here http://en.wikipedia.org/wiki/Trans_man