My overnight session for Mistress Vonn was probably the most memorable and enjoyable night of my entire life.
I was yet again ordered to wear my girlfriend’s panties and wide leather belt and to do lines on the journey in.
This was so very humiliating and I don’t think I will ever get used to the feeling of shame this causes me.
I was in Glasgow city center for lunchtime and Mistress ordered me to walk along Argyle Street knowing full well that this was the time that the offices would be having their lunch break.
As I am under contract to Mistress and one of the clauses is that I am fine £1 for every dirty thought the sight of so many pretty girls in short skirts was always going to rack up the total.
I started the day at £11 and after twenty minutes the total had reached £30.
Being under orgasm control for 15 days really did not help the tension one little bit but of course, that is my problem and as Mistress is in charge I would not dare complain.
All-day Mistress sent me texts teasing me and warning me of the dire punishments that awaited me which really racked up the tension.
On an impulse, I headed out to the West End to kill some time and keep my mind off dirty thoughts.
At the Botanic Gardens whilst keeping my head down to avoid seeing the sunbathing girls, I had to use the public lavatories.
The Gents was very busy and I had to wait in a queue of twelve people to use the urinals.
When space appeared I headed for it. I undid my girlfriend’s belt but forgot that as it is over two and a half inches wide, thick, and with a heavy silver buckle the weight of it made my trousers fall down to just below my knees.
I managed to catch my trousers before they hit the floor but then realized to my absolute horror that I was standing in the toilets with my trousers at my ankles in front of over twenty men and I was showing off the pink lace French knickers I was wearing.
I had no choice but to use the toilet as I was desperate but I was worried two things would happen
1 I would be beaten up
2 I would be followed out the toilets and chatted up.
Thankfully neither happened and I left with as much dignity as a man showing off his woman’s panties in public could muster.
I ended up in the Glasgow Art Gallery to kill some time and stay away from temptations and therefore fines where I made a bit of a fool of myself* but I still could not keep my mind off what was to happen later.
*A very Bohemian styled lady was taking a group of trendy art students around looking at the paintings and she was wearing a very short tight leather skirt with black tights(Kerching and other £1 to the total)
I was listening to some of the ways she was describing a horrid modern art painting(an interesting form of social commentary whilst still surreal and accessible) while I was engrossed in looking at a Lowry painting of a crowd scene of factory workers leaving the building.
I realized I was in her way and apologized but she said she noticed I was enjoying looking at the painting and asked if I would share my thoughts with her students as it was interesting to hear the views of a layman on art so I said.
‘look there are lots of dogs in this picture and there is one big one who is off the lead’
She and the rest of her class made a hasty retreat as they probably feared I was a raving lunatic.
I killed enough time and headed out to see Mistress.
An elderly couple sitting on the wall across from the building said good evening to me as I passed them.
Of course, I was still a bit of a mental shambles and I forgot the number of the building, and when I texted Mistress to ask I was told that as punishment I was to walk around the building again.
I did so.
The same elderly couple said good evening to me as I passed them again.
I returned to the building again only to get another text telling me to walk around the building again.
Once more full of excitement and tension I walked around the building.
Again as I passed them the elderly couple wished me a good evening but looked a little worried.
Again on pressing the buzzer, a text arrived.This time I was to walk around to the park and bring Mistress four different leaves.
This I did bring four nice leaves* as I was sure if any were not nice looking this would be held against me an punishment would be issued.
Stopping only to pass a football back to some local kids showing off my amazing skills** I headed back to Mistress.
Again I returned holding the leaves carefully in my outstretched arms and passing the old couple who were by this stage calling the neighborhood watch, police, and mental asylum in that order about the strange man who kept passing them by.
They did not wish me a good evening.
*Finally I was admitted to enter the building and then the butterflies really started.
It was so wonderful to see Mistress again. I also forget how stunning she is until I see her and also amazingly she is a member of one of the most exclusive clubs in Scotland*
We had a really nice long chat then Mistress did a lovely thing and made me a nice meal.
In a way, time stood still and I almost forgot I was going to have an overnight session, and to be perfectly honest I was so comfortable happy, and relaxed in Mistress’s company it wouldn’t have bothered me if I didn’t.
*People who are genuinely glad to see me
I was taken into the bedroom and ordered to strip with the humiliation starting right away as Mistress laughed at the belt and especially the panties she ordered me to wear on the journey.
I was dressed in the tight secretary dress with wide belt and with a stockings bra and tights and wig on I was totally humiliated.
It is the little gold ladies watch that really hits me how much of a sissy and humiliated I am
I was ordered to make Mistress a coffee and as I didn’t know what way Mistress wanted it made I was immediately given 200 lines and told it was my problem to find out what Mistress likes and dislikes.
Mistress left the room to get ready and returned in a long grey skirt looking absolutely stunning and so very strict it took my breath away.
The coffee was not up to the standard expected so I was ordered to do two hundred more lines.
I should have realized something was up. Mistress kept on laughing when I was doing the lines. Not the usual laughing at my discomfort but a more happy and contented laugh.
I should have learned my lesson from a text Mistress sent me months ago*.
I was of course oblivious to this and continued to do my lines.
Mistress decided enough was enough and started my punishment.
I was bent over Mistress’s knee and given a lecture of my bad behavior and spanked very hard with the hairbrush.Despite my protests my skirt was lifted up the panties were taken down and the hairbrush was administer even harder on my bare bottom.
I had to count out the strokes and thank Mistress and I was spanked this way till I was crying genuine tears.
* Expect the unexpected from your Mistress.
Mistress then ordered me to put out the sheets of lines I had done (over 8 thousand) on the floor and lie on them for some pictures to be taken.
Mistress was actually giggling at one point and when she started to video me I knew something was up.
She asked me a number of humiliating questions about how long it took to do the lines.
Then I was asked what I thought she wanted me to do with the lines.
It was then horrible thought occurred and by the look on Mistress face I knew she had the same thought.
‘You’re going to make me rip them all up aren’t you?’
Through her hysterical laughter I managed to hear Mistress say yes.
I have never been so humiliated in my entire life as I ripped hours and hours of hard work into little pieces while Mistress laughed and stood and crunching up all the pieces of paper.
This put Mistress in a really good mood so she decided some caning was in order and I was told to fetch a cane.I chose the whippy thin cane and was thrashed to tears with it.
I keep forgetting how hard Mistress administers the cane and I could tell from her voice how much she enjoys it.
I tried making a joke* to get out of the caning but Mistress wasn’t buying it and laid it on worse.
The black cane or the black and blue cane** as I call it was then used.
I was introduced to the delights of the electrics on both of my bottom cheeks while being shocked and caned over the knee with the black cane.
The pain on my already reddened bottom was very bad and the shocks made it so very much worse.I was offered the chance of the electrics on my penis and testicles but declined as I am a bit of a coward and didn’t have the balls for it***
* Mistress asked if I wanted the black cane and I said no and ‘As I am a hero with cowards legs’. I often think if there was a graveyard for jokes that didn’t get a laugh it would be filled with mine.
Me ‘I’d like to bury this joke please’
Gravedigger ‘I am sorry sir there is no more room in the graveyard thanks to you’
** The colour the bruises it causes on my bottom.
*** Gravedigger ‘Sorry sir I already told you the graveyard is full’
Another stroke of genius was for Mistress to make me bring the full-length mirror in and place it so whole bend over the chair I had the glorious sight of Mistress standing over me and thrashing my bare bottom with the strap/cane.
There were so many highlights of the whole session.
Being made to get the number 2 then black cane and knee before Mistress before being caned to tears with them.
Mistress changing into a black leather skirt and just being so beautiful that I barely could look at her.
Sent to bed in a nightdress and yellow panties and being awake all night expecting the unexpected and Mistress to drag me out of bed for more punishment which even though it didn’t happen didn’t stop me worrying it would.
The next morning I thought Mistress would be tired but she was not.
Indeed she was unhappy with the lack of quality marks on my bottom and said more than once(which made my legs go weak)
I am going to really thrash your bottom till it is red whealed and blistered and you are crying your eyes out.
Mistress was good to her word and to be allowed to relieve myself I had to take 40 full force black cane strokes on the bare.
I had just a wondrous night with an truly amazing Mistress and I can’t thank her enough and I can’t wait to do it again.