tagBDSMMy Halloween Pony Ride

My Halloween Pony Ride

byKathy Gray©

Hi Everyone,


So many people asked me to post a story giving a description of the Nights entire events that took place on Halloween night.

So I'm also going to tell you about the events that went on. EVEN, Before I actually came up on stage for The Wooden Pony Ride.

I think you will ALL enjoy the events of the entire night.

So this is it. It's pretty long because there is so much to tell. Especially about the Pre Pony Ride negotiations to change some of the terms and conditions of the wooden pony ride.

They all seemed like a good deal and OK thing to do to me at the time.

But I found out that I didn't make too smart of decisions.

Although I made what turned out to be some stupid decisions I did come through the whole thing OK


Anyway, The date was changed for the event to Halloween Night.

Since all of the men attending were Quite Wealthy and from all around the world.

Being members of this some what of an Underground Business Men's Club.

They were all able to travel easier during the week then on the week end.

Of coarse being Business Men they need to travel for business. Yeah Right.

But it did work out and there were nearly 300 men present for the event.

They did add a lot to the Event to make it an EXTRAVAGANZA!!!!

Sense it was Halloween night the main member of the Host Club all dressed in Mid Evil Dress and had the Stage Area all Decorated into the Mid Evil scene.

They added five additional females to the Event also.

Two Girls were paid to do a striptease show and then to get their bare butt's paddled.

Two other Girls were paid to do a striptease show and then have their pussies whipped or flogged.

The thing is, just like me and the wooden pony.

I had never ridden the wooden pony before that night.

None of these Girls had ever been paddled or whipped before either.

The whole theme and draw of the Event was that they had females that were basically Virgins to being paddled, whipped, and Riding the Pony.

The fifth Girl was a real surprise.

She was a nearly 6' tall body builder type, But very well built Dominatrix.

She was the one delivering the paddlings and the floggings. As well as the one that would set the wooden ponies crossbar in place for me and whip my cunt at the end of the entire event.

In a few words, She was a very brutal Dominatrix.

She was hired by the club to basically show no mercy what so ever to any of the girls and believe me, she did just what she was hired to do.

To give no mercy and be brutal. "THAT SHE WAS"

On Halloween night the Club house, Which is in a huge warehouse type building somewhere around Chicago. I Had no idea where.

The place was packed with nearly 300 men the female participants & the Dominatrix.

At 6PM. the very first girl came out on stage and did a 30 minute striptease show.

After her show, a bench was rolled out on the stage and She was taken over to it by two men dressed like Mid evil executioners.

They had her kneel on this rail that looked like the kneeling board in a church only much higher off the ground.

The two men pulled her knees wide apart and then put straps around her legs just above her knees so she couldn't shut her legs then they pulled Her feet together and strapped them together at her ankles.

They then bent her over the rail and put straps around her torso so basically, she could not move at all from the waist down.

They put long straps on her wrists, That made it so she could move her hands all around. But she could not get her hand below Her own waist. She did have a couple of hand post she could hold onto up above Her head shoulder width apart.

Basically from the waist up she could move around, Couldn't move at all from the waist down.

Her Bare Butt was really pronated out and was really stretched out tight.

I've been paddled before and I knew this girl was in for much more then she could possibly have expected.

She was paid to do the striptease and then was paid $500. dollars to take 5 whacks with a wood paddle.

The paddle was made out of a regular piece of board. Was probably about 8" wide and at least 2 feet long and I would say 1" thick.

The dominatrix came out with the paddle and turned to the audience and held both arms above her head with the one end of the paddle in each of her hands.

The audience clapped their hands and roared their approval.

She went up to the girl and got in position beside her exposed bare butt.

She pulled way back with the Paddle and then swung forward with and unbelievably loud Whoop Sound, The paddle landed directly on the strippers bare ass.

The girl arched up and SCREAMED like you wouldn't believe.

I think it was then that she realized that she was in way over her head.

She was pleading with the Dominatrix to not do it so hard.

But one minute exactly after the first whack She pulled back and Delivered the 2nd. whack just as hard with and equally loud Whoop sound as it Hit her Butt.

The girl screamed again and then started pleading with the MC of the event and anyone else that was close enough to her.

The Dominatrix simply said to her loud enough so everyone in the building could hear.

"You can plead all you want honey, but you're going to get the 5 whacks and there's nothing you can do about it."


They offered you a deal with certain terms and conditions and if You accepted the deal then you had no way to get out of it or stop it.

You had no choice but to take it all, Be it the paddling, The Whipping, Or Riding The Wooden Pony.

Well, The girl made it through all 5 whacks. She was crying like a baby when they unstrapped Her and took Her off of the paddling bench.

Her ass was a very dark Red and you could see that her butt was going to be black and blue in a short time.

Her legs shook as she walked, I don't think she will ever agree to anything like this again. THEN, The 2nd. Stripper came out from the back room to do her striptease Show.

None of the other girls got to watch or hear what was happening to the other girls before them other then Me.

Because I have already done these things for this club.

Only the paddle was nothing like the one being used and I wasn't whacked that hard.

I couldn't see myself doing that.

Anyway, after the girl got done with her Show they took her to the paddling bench and strapped her in the same way.

She was also paid to do a strip dance, And paid $1000. dollars to take 10 whacks.

The Dominatrix pulled back and again swung forward and delivered another big hard whack.

The Girl yelled out, But more like she was Pissed off rather then hurt.

The woman delivered 4 or 5 more whacks and the girls butt was already a very dark red and was starting to turn black and blue.

After the 7th. whack The girl started yelling at the Dominatrix, cursing at her and calling her a Big Bitch among many other things.

This was not a very smart thing for her to do. On whack #8 the dominatrix pulled back a little further and swung forward a lot harder.

The paddle made a noticeably louder Whoop sound as it landed directly on the girls bare butt.

She swung so hard that it actually moved the bench forward when the paddle landed on her butt.

The girl screamed, The first time she actually screamed in obvious pain. Then started saying, OK, OK, OK, You proved your point. I'm sorry.

The Dominatrix just said aloud,

You should learn to keep your mouth shut Bitch.

After that She gave her two more equally as hard whacks with the paddle. You couldn't help but feel sorry for her but also you couldn't help thinking what a stupid girl she is yelling and calling the woman names that has the paddle and is the one beating your own ass.

Well, They unstrapped Her and She couldn't even stand up on Her own. The men had to help her up.

She could walk but but very very slowly.

Her entire ass was already all black and blue and had several welts bumping up.

Then the 3rd. girl came out and of coarse did her striptease show.

She was also paid to do the Strip Show, And has also been paid $500. dollars

to take 10 Whip Lashes on Her Bare Pussy.

After her show, The men lead her to a bench that was up on the stage and was the same height as those folding banquet tables.

She was laid on her back, They put a big wide strap around her hips to obviously keep Her from being able to move Her torso what so ever.

They then put straps on her wrists kind of handcuffing her hands together and then pulled them straight up above her head and fastened it to a pole.

Then each man grabbed an ankle and put on an ankle restraint. They pulled out two ropes each and hooked them to the ring on the ankle restraints.

Then the mistress started cranking this real large Wood Wheel and as she turned it the girls legs with her feet together started lifting until they were straight up in the air.

Then She cranked another wheel and the Girls legs started spreading apart wider and wider. She cranked them so wide that the Girl was moaning aloud because of the Over spreading of Her legs.

Then she cranked the first crank again and pulled Her feet and legs back even further until they were way back and her Bare Pussy was pointing Straight up in the Air and believe Me Her Pussy was fully exposed and spread open.

The Dominatrix came up with a vibrator and did the girl's clit until it was sticking up and hard.

She then got out the Whip, It was pretty thick and again about 2' long straps.

Again, She turned to the audience and held the whip above her head in both of her hands and again the audience Clapped and yelled their approval.

She turned to the girl, She obviously looked scared and rightfully so.

The Dominatrix stepped up in front of Her Pussy, She slowly pulled the Whip up over her right Shoulder and then swung down fast and landed the Whip directly onto the Girls bare pussy making a loud smacking sound as it hit.

Kind of like a belt hitting something.

The girls head popped up and She yelled out as Her entire body flinched & jumped.

She really didn't say anything.

Then Lash number 2 came and again the girl jumped and yelled out, Then lashes 3, 4, & 5 came.

The Girl then started saying that oh Please Stop, I can't take it. over & over again.

No one said nothing including the dominatrix. She just delivered lash #6, then 7, and 8.

The girl quit saying anything and just held on and braced herself.

Number 9 and 10 lashes were obviously harder and the girl screamed out even louder.

The uncranked the wheels and lowered the girl's legs part way and the men unhooked the ropes and straps and helped her up.

Her pussy was very very red and You could see that they were a little swollen.

It was obvious by the way she was walking that it was very very tender as well.

But she didn't seem in too bad of shape though.

I don't think she will ever do it again, however.

Then the 4th girl came out. She again was paid to do a strip show and was also being paid $1000. dollars to get 20 lashes on Her Bare Pussy.

It all went the same, as the first girl and they strapped her in on the bench in the same way with her legs spread wide open.

This girl was a really surprised after the first lash Hit her Pussy and She screamed aloud and right away started yelling out.

"Wait a minute, Wait a minute, there's no way I can do this. We've got to stop.

The dominatrix said aloud. "Yell all you want honey, But Your getting 20 lashes."

The Girl did yell and scream on each and every lash. Each lash was very hard.

You could see that Her Pussy was quite swollen for the last 3 or 4 lashes and was very swollen after it was over.

Her cunt lips were very very puffy and were all bruised pretty bad. She was obviously in a lot of pain.

They lowered her legs and unstrapped her and helped her up, She could barely move.


It was time to go to the stage where the Host Clubs Leader or president of the Club was to make me offers to change the terms and conditions of the wooden pony ride.

I had the option to either accept or refuse any offer.

The first thing was that they had purchased and given me a pair of very high spike high heels to wear during My Striptease Show, The walk around and during the pony ride.

They said they wanted me to wear them because they looked so much sexier.

I guessed them to be about 5" heels. I always wear 3" heels. But these heels were very expensive shoes and felt and looked fantastic.

They offered Me an additional $500. dollars to wear them.

So I agreed to wear them. I figured it would be better for the pony ride anyway.

( My 1st. mistake)

The 2nd. offer they made was they wanted to know if it would be OK to move the ropes holding my arms and wrists above my head forward a few inches every 15 minutes during the ride and for this they would give me an additional $500. dollars.

I thought it shouldn't make that much difference one way or the other. So I agreed.

( Mistake #2 )

Their next offer was this, They wanted to be able to pull on the chains hooked to My ankles half way through the ride or at the 30 Minute point of My ride.

They wanted to spread them apart so that My feet are No longer on the floor.

They went on to explain, That after 30 minutes I would not be able to stay up on My toes any longer anyway. So it wouldn't really make a difference.

This I knew was some what true because I had been practicing being up on my toes and after 25 to 30 minutes I could barely get up on them anymore.

They said they wanted to spread my legs apart at the 30 minute mark just to make the

Pony ride look more exciting for the audience. "Which it obviously would".

I knew it would cause more pressure on my cunt but I didn't think it would make that much difference since I wouldn't be able to be on my toes anyway.

For this they offered Me an Additional $500. dollars.

I thought what the heck, For another five hundred dollars it was worth it.

So I agreed to the spreading of My legs.

( Mistake #3 )

Finally, They wanted Me to get into the spreader bench and to let the Dominatrix do a 10 to 20 minute masturbation of My Cunt just before the pony ride.

They said again to make it more exciting for the audience. Especially sense they know that i tend to have very wet and gushing orgasms.

Since I love that anyway, I agreed to that without a second thought.

Anyway, All together The Club offered me $2000. for the wooden pony ride, Plus an additional $500. dollars to let them spread my legs at the 30 min. mark another $500. dollars to allow them to move the ropes holding my wrists forward and $500. dollars to wear the 5" high heels.

So it all came to $3500. dollars in all, to Ride the Wooden Pony for 1 Hour.

Now that the deals were all made it was time to get on with the Show.

Like the Other Girls I was also Paid to do a Striptease Show before My Event.

I did My B/D&S/M Striptease Show. Putting clothes pins on My nipples & Weighted clothes Pins on My Nipples and Pussy Lips to the Audiences Delight.

After My Strip Show I had an additional condition. I was to Dance and move through the entire audience so that Every Man there could feel, rub, massage, and look at My Cunt Lips and clit So they could all see and feel just how big my cunt lips and clit really are.

Of coarse I knew that they also wanted My cunt lips and clit to be overly aroused and pumped up for the wooden pony ride. But it also got Me turned on and ready for the ride.

After just over a half an hour for My Striptease Show.

I started Dancing around through the audience letting ALL the Men touch feel and look at My cunt all that they wanted to, Which I might say turns Me on to no end having that many Men look at an touch My cunt.

It was now time for the Masturbation, So I went up to the stage where the Host and the two guys dressed like executioners, they then lifted me up on the spreader bench and then hooked up the ankle restraints and ropes and turned the wheel and spread My Legs wide open.

The Big Dominatrix came up to Me with a Vibrator in her hand and to my complete surprise leaned her head over and started licking My cunt.

I had almost an instant orgasm, She licked and tongued My cunt for a very long time and made Me have several Big Orgasms.

She then started masturbating me with her fingers with a side to side motion which really drives me wild.

I started having more orgasms and juice started running out of my cunt with each orgasm.

After what I would say was 10 minutes, She turned on the Electric Vibrator which they called a Sonic Vibrator. She stuck it directly onto my clit very hard.

I have had a lot of different vibrators used on me, but this one was by far the most intense vibrator I had ever felt.

In less then a couple of minutes it became so intense that I was having continual orgasms. She then started running it all over My cunt lips and shoving it in my cunt hole.

She returned to My clit and rather relentlessly kept it on my clit and cunt lips until I was having huge gushing wet orgasms one after the other.

After at least 20 minutes of the masturbation and vibration, She turned it off and then Licked it a few more times making Me gush out a couple of more huge orgasms.

She had definitely accomplished her goal of making sure My cunt lips were all pumped up and My clit was fully erect, believe Me they were too.

They unhooked the ropes and got me down off the spreader table and took me over to the Wooden Pony which had been moved out to the center of the stage.

The two guys dressed like executioners took Me over to it, like it was an execution.

They had me step over the lowered crossbar which was at about knee height and centered me over the bar.

They had left on the ankle restraints and all they had to do was hook up the chains to them. They spread My feet apart wider then I thought they would which was wider then shoulder width and hooked the chains to the outside of My ankles so I could not move My feet closer together.

Then they put Velcro handcuffs on my wrists and hooked the ring at the center of the cuffs to a hook on a chain coming from up above.

They pulled up the chain and My arms rose above my Head until the were straight up above My head.

Then they set up the timer and Had it set for 1 hour. It had a big round face on it and they set it in front and to the right of me where I could clearly see it.

As the ride went along I wished I could not have seen it.

Anyway, Everything was set except for the crossbar.

The Dominatrix came up on the stage and up to the Wooden Pony and turned to the Audience and said: "Is Everyone Ready For This"??

The audience All replied, "YES"!!!!!! VERY LOUDLY.

She bowed to the audience and came around to the side of me and put her hands under my underarms and lifted me WAY UP ON MY TOES.

The two men put blocks of wood under the Heels of My Shoes. (I did not expect this)

The Dominatrix then raised the crossbar up between my legs, I could feel the crossbar touching my clit and She reached under me and pulled my cunt lips out to each side of the crossbar.

I said to the Dominatrix, "I thought the crossbar was NOT to be touching me at all".

She smiled at me Rather menacingly and said,


She again faced the Audience and said, "Are You Ready"????

They again replied all together, ""YES""!!!!!!!!

She said aloud, "Start the Clock AND Pull The Blocks"!!!!!!!!!

Before I could even think about it, The Men jerked the blocks of wood out from under the heels of My Shoes and My Cunt came crashing down on the crossbar.

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byKathy Gray© 13 comments/ 82532 views/ 15 favorites

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