Its a hard job

sex stories

Well I suppose I should introduce myself before I tell my tale

I’m a guy employed by women to cause them pain, now a lot of guys cause women pain but I am one of the very very few to get paid for it

So what do I do and how do I do it? Well I run a very exclusive service, its word of mouth recommendation only and I am very careful as to whom I accept as clients.
So I know what you are thinking I am one of those a fabled male prostitutes, a good looking guy that spends his life kneeling between old women’s legs tasting fish and smelling talcum powder

Well no that’s not me I am fat, smell a bit (especially when it is hot) and I work as a dominator but only in the evenings, by day I am just another sad office worker
You see there are a lot of women out there that liked being spanked or caned
Probably similar to the male judges and politicians that enjoy spending their evenings dressing up in women’s clothes. Getting beaten and humiliated by women for their trouble.

What will surprise you is a lot of men like being with women whilst they are humiliated.
Certainly one of my most popular bookings is the ‘man from the ministry’ where I turn up suited and booted to administer a official caning to a lady caught speeding or some such similar crime
A lot of role play and props, I arrive with official looking sheets explaining how the caning will be administered, give formal instructions on where she should be to receive it (as it were) and her man gets to argue with me about how unfair it is and then comfort her after its all over.
Sometimes she will plead with me to sleep with her instead (and if she is fit enough I would certainly consider reducing the number of strokes) but generally it is just a caning.

I will be honest sometimes it feels tacky, sometimes I feel dirty I live my life with a hulking great traveler on speed dial (he spends a lot of his life sitting in cars outside where I am in case something goes wrong)
But anyway I earn a fair bit of dosh (and even pay tax on it) so it’s a good little second job.

As some of you probably know you do have to be careful when you administer a caning that you don’t hit to high (you can damage the back doing that).
Here is an interesting factoid throughout history the majority of canings and floggings were always on the buttocks. Then Hollywood arrived and that wasn’t something they could show on movies in the early part of the century so they moved all the punishments on to the back instead.
The buttocks are practically designed to take punishment without permanent damage

So preamble over, the story I am going to tell you today is about four women and a birthday party
They had booked me up for an entire evening for competitive punishment. Now that is where games are played and the loser has forfeits. It’s not an unusual booking, what was unusual was that they wanted all my equipment

They literally had to clear a room of all furniture and it took me over an hour to set up (still at least it gave me an opportunity to use my highly paid large friend)
So the women were in their fifties, and had that ragged look to them, probably a dozen marriages between them and even more children. They would have been lookers when younger and were still pretty but the hard faces and harder eyes showed the life that they had.

So at first glance I could see this was going to be interesting, girls like this like to hurt, vindictiveness and cruelty is second nature to them (mostly cos that is all they have ever experienced)
So the birthday girl was going to get the first treat (I think we will call her Rose), she was a short blond and as she removed her clothes for me I could see that it had come from a bottle. She had a reasonable boob job and a trim figure though.

As it was her birthday she got to have a go on the belt driven masturbation machine I have
Picture a narrow rubber conveyor belt driven by a power drill at one end standing about two foot of the floor , on the belt every four inches or so are soft v shaped pieces of sponge.
Each piece of sponge is soaked thoroughly with lubricant
Rose was instructed to sit as far forward as she could on a stool (supported by two of her friends) her legs apart and the belt of the machine running just under her bottom.
Then it’s just a question of spinning up the power drill, the tips of the bits of sponge stimulating her as they hit her one after the other. You can vary the speed of the impacts by varying the speed of the power drill
You could see that she was enjoying the experience a lot (the screaming gave it away) and when she came she actually ejaculated so far she made a mess on the carpet, lucky it was her place really
A very definitely happy customer and a good lesson to the other three girls of the potential fun they could have

Win the game and get a go on the masturbation machine, lose it and have a forfeit

And now the fun begins, girl number 2 who I think we will call Alice. The games are simple enough, sub pub quiz level as all the girls had been drinking for a while, and you could have constructed a reasonable sized life raft from the empty bottles lying around. What did women of a certain age do before Tesco’s three bottles for a tenner offers came along?

So Alice went for the high/low card game I’m sure you have since Bruce doing it on TV, it really isn’t too difficult. You get a playing card and then have to guess whether the next card is higher or lower.

Not really a spectator game either but with a potential forfeit everyone was excited.
So she lost and it was time for the forfeit.
Her forfeit was a spell on the caning of strokes to be determined by a D20 I always carry
Now for those of you that didn’t have a sad childhood like mine a d20 is a twenty sided dice popular with players of dungeons and dragons Yes that ever popular role playing game for thirteen year old boys that all sit at the front of the bus and smell of cheese (at any temperature above freezing)
Why do I still carry a d20, cos it amuses me that something used by so many sad kids could be used for such fun sexual games.
And of course the same sort of girls that picked on me for being nerdy at school are the ones that now derive pleasure from hurting their friends

So anyway Alice rolled a five (lucky break there) and was helped out of her clothes by her friends
Now here is one of those tricky and thorny legal problems, if it’s a one on one I always get the girl to give me a safety word, you know a word that says basically cease and desist
That way legally I should be ok and able to avoid any charges, though it is a grey area as if the damage shifted towards ABH or GBH you could still be prosecuted even with a willing participant
But in a group I can avoid being involved so much, and many times the group doesn’t want me to be involved at all.

So Alice was yet another bottle blond, short stubby and no doubt attractive after a few pints, her friends gleefully followed my instructions to attach her to the caning machine
Simple enough bit of kit (though very expensive) cannee (is that a real word?) starts in a standing position with a metal bar at crotch level in front of her
Her hands are strapped to two cables that lead into the base of the machine in front of her and her feet are strapped together and attached to the rear of the machine
A further strap secures her knees to the machine so she can’t fall over sideways and break her ankles
Then there is a cane on a arm behind her that is set to just touch her bottom when she is bent over
The machine is then programmed with hardness and number of strokes and everyone stands back to enjoy the fun

Now Alice is half cut on cheap white wine that I doubt was made with grapes and doesn’t know what to expect
The machine sparks up, the cables holding her arms tighten and she is slowly pulled down until her bottom is the highest point of her, a similar position to if she was holding her ankles
The machine then administers the first stroke, as you would expect a loud crack and a bright red line appears straight across her bottom
Now when you are hit that hard it takes you a few seconds to realize how much it has hurt, in that time the cables have loosened to allow you to regain a standing position and you suddenly realize you can’t move away from the source of the pain and there are strokes still to come.
And that’s when the pleading and cursing start, the limited numbing effect of consumed alcohol wears of quite quickly and no one wants any more pain. People will start by pleading, its human nature, I didn’t realize, it hurts to much, I’m sorry etc etc etc

About 30 seconds into the pleading phase the cables start to tighten again and the hands start going down
This usually inspires the threatening phase, the let me out or else stage now that is when you have to apply a bit of psychology explain she knew the risks before she started playing and its hardly fair to back out now etc etc

This argument is usually interrupted by the second strike which tends to escalate the threats
At this point I produce a ball gag and offer it to her friends. They are creased up and have no hesitation in gagging her (it is always important to think of the neighbours as well, they tend to get angsty about people screaming next door)
So the third stroke brings the tears, tears of rage, tears of pain and tears of impotence she doesn’t like this at all now
Fourth stroke she tries to shove her bottom as far forward as possible, her skin goes bright white where the bar touches her. Now that isn’t a good plan as it gives the cane more time to flex, if you are ever strapped to a caning machine just stay where you are put anywhere else is going to hurt more
Fourth stroke really hurts her and she wets herself, why do girls wet themselves when caned? Dunno a fair few do though and it is worth bearing it in mind if it is your carpet
Now she has drunk a lot of wine and my plastic sheet isn’t quite big enough, bit of seepage and it’s a fair guess that the carpet is a gonna. Owner looks less pleased; she probably has a man away fishing or something and will need to explain the stain somehow

Alice gives up at this point, still crying but her body has gone limp, she makes no effort to resist at all as the fifth and final stroke descends and then it is all over
I am over their quick to let her go as rose is going a bit mental about her carpet and wants her given another five strokes
Alice is in my arms and it looks like she doesn’t want to leave them, she is in a really bad way emotionally (she probably hasn’t wet herself since she was six and her bottom will hurt)
I suggest I take her away to the bathroom and punish her on her own for messing up the carpet, rose is ok with that as she is now concentrating on trying to clean the floor up.
The other two girls are looking a bit green now as it could be their turn next on the caning machine.
So I take Alice up to the shower yank my leathers of (hey never pass up the chance to shower with a lady) and drag her into a nice warm shower and start making her feel a bit better as I wash her.
Alice is in a very bad way and wants me to keep her away from the other girls (I think that’s another friendship gone) so I explain she has to be punished again

Oh dear more tears, her body has gone into a floppy sort of state where she has stopped resisting anything and just wants to stop bad things happening to her. I could have sex with her right now if I wanted to, she would do absolutely anything to save her bottom but as I said before I didn’t really fancy her.
But that’s the weird psychology of this, the girls enjoy almost need to be hurt and are grateful to the person that wields the cane. My guess is that a lot of them had bad childhoods and would be doing better with a few trips to a good psychologist.

But I have bills to pay and I am not retraining as a psychologist to explain to endless women that they need to separate an emotional need for love with a desire to be dominated and humiliated.
That said I am not totally heartless and I didn’t want to hurt her any more.
So I told her she was going to lose her bush (and her bush obviously had not been attended to for years) I think she thought I was going to rip it out by the roots but the shaver I always carry was easily up to the task
And of course she will need to explain her new bristly status to her boyfriend/husband which would probably be an amusing conversation

So a quick shave and a blocked plug hole later she was in a deforested state, and whilst shaving her my fingers had slipped inside her a number of times and she was in a better place than before. She had had her fix of humiliation and sex and felt so much better for it
So we went back downstairs where the ‘how do you get piss out of a carpet’ arguments were still raging
I explained she had been punished, didn’t explain someone now needed to unblock the bath and we moved on to lady three
I can’t even remember her name, except she was a clever one, now I am not saying my games all are rigged except that they er are
Well what do you expect? I turn up and leave five minutes later after everyone passes

So she must have guessed the high low card game was a fix and guessed accordingly.
I was really pissed as she was the hottest girl there, a little cutie and I had been looking forward to having her
But she got her go on the masturbation machine and managed to contain herself enough to save the carpet
Now all of you are thinking how mean am I not to let Alice have a go, well its easy she wouldn’t be wanting to sit down anywhere for a while and you can’t use the machine without putting all your weight on the buttocks, I have no idea how these girls get driven home at the end of the evening.

So it is just girl 4 now, who we shall call Mary
She was tall, easily five eleven and blond with curly hair, chunky body but attractive enough
She must have been thick as well as even after seeing what girl 3 achieved she managed to lose the card game, she had initially tried to bottle out but there was no way Alice was letting that happen after what she had been through

Alice was really revved up, she was all for Mary spending the rest of the evening attached to the spanking machine but I had other plans
It’s the nice thing about these group exercises the people going last (who are usually the most reluctant) cant back out by the time it gets to them as their friends won’t let them.
If you get caught in one of these evenings go first and then negotiate your punishment down by pointing out to everyone else they will get hurt as well.
Why go home with a dozen red stripes across your bottom when you could have half a dozen gentle slaps on the bottom with an open hand instead.
But the alcohol usually promotes a sense of false optimism
Anyway we carefully removed Mary's clothes
Nice figure going stocky round the middle and nice large natural breasts (sagging with age) nice big sticky out nipples and that’s what I had been hoping for

So out comes my third machine, like the old fairground game where you have to move a metal hoop along a bar of twisty metal and if the hoop touches the metal a bell rings (and you lose)
This was the same except there were two loops (one for each hand), she started in the middle and had to move both hoops to the outside (left hand to left outside right hand to right outside)
Oh and her nipples were part of each circuit

Now if you are thinking of building one of these at home DO NOT use mains power, even with voltage and ampage droppers in line if something goes wrong you could kill her
Instead use small batteries, the nipples are sensitive enough that they don’t need a huge jolt through them
Also don’t attach crocodile clips to the nipples (unless you want a nipple less victim) a modified nipple clamp does the trick with a crocodile clip attached to that.
Some girls have permanent nipple piercings of long bits of metal just to facilitate this.
Now this game is tricky if you are cold sober, with six quid of wine inside you no chance
Your best bet is to just take the pain and move the hoops quickly to each side, but who would give up like that.

She had enough sense to only move one hand, her right hand her best chance. She had moved it about three inches (total width of the toy is two feet, but it does bend a lot the wire length is nearer four feet) when she hit.
She didn’t enjoy the jolt of current through her nipples, the jolt through her right nipple made her touch the metal with her left hand as well.
But she got control quickly and got both hoops of the wire so it stopped shocking her.
The pain had sobered her up and she started having a better look at the game, she steadied her left hand and started moving her right hand a lot more slowly and with a lot more care.
But the booze always knackers you, the false confidence it gives made her go to quick and she had another jolt
This time she avoided jolting her left breast as well.

Anyway as you can imagine it took her about ten minutes to finish the game and her nipples were smarting at the end.
So then we were back to the birthday girl Rose who had been enjoying her friends being hurt so much.
At some point in the evening she had got a bit shy about being naked and had thrown a man’s shirt on, no idea why she hadn’t got dressed again properly.
Maybe she had gone into the kitchen when I was upstairs with Alice and hadn’t wanted the neighbours to see her naked, maybe she just felt shy.
Anyway part of the rules I hand out beforehand is that after losing clothing you only get to put it back on with my permission.
There was a lovely range of expressions on the girls’ faces when I pointed this out, and a few glances at the spanking machine.
But this was going to be old school, over the lap special, she took of the shirt (and the pair of panties she had lobbed on) and then stretched out over my lap.

Now a spanking like that loses you control, if you are going to spank over your legs get the girl to stretch out her legs as far as she can go so she is practically on her toes, then have her buttocks above and slightly to the right of your right leg.
Have her lean forwards on to her hands that she must place as far in front of her as possible, then have her give you her left hand.
She is now effectively immobilized she can’t move her right hand without falling on her face (so that stops her reaching back and trying to avoid being hit) and as long as you keep her weight forwards she hasn’t got the leverage to move her legs.

I then invited the other girls to try what is called my star paddle, effectively a rubber paddle with star shapes cut in it. If you hit someone hard enough with it it leaves a star shape on their bottom.
The beauty of this was as she couldn’t see behind her she wouldn’t know who was hitting her.
Well I can’t say who hit her (in case Rose ever reads this) but trust me the girls laid in hard and her bottom was very red at the end of it with a few nice star shapes standing out.
Then that was that, I rang Albie (my traveler) and he came in looked around at the now dressed girls that all looked like they had gone through a war and helped me pack the equipment away into the van and we drove away
What happened to the girls next, are they still friends I have no idea, they probably are but they haven’t booked me again so I don’t know
So that’s a taste of my life, and its up to you reader am I a sad sadist earning extra money providing a special little service or am I a sad 17 year old dreaming of a sad little lifestyle whilst wanking of to the latest teen pop sensation?

story by: weety666



Tags: fantasy sex story

Author: weety666



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