The Deep End

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

With Mistress Michelle, we never got to the whipping phase. After her approach and my introduction, I looked up at her beauty and smiling said that I had watched her for years every weekend as she presented the local weather report and blurted out that I had a crush on her and thought that she looked fantastic.

"Do you wish to taste your weathergirl william."

"It would be an honour Mistress," I replied and then proceeded to place my head between her legs as she raised her dress. She was hot and wet and in need of an orgasm. My tongue worked hard on her clitoris as she pumped her body into my face. When it was swollen, I was able to hold it with my lips as my tongue ran over it. It was not long before she was moaning with an orgasm and love juices covered my face. Then she stepped back dropping the whip and walked over to my Mistress asking her in jest if she would sell me to her.

After I had gone through my meetings with each of the Mistresses, I knelt with head bowed and knew that Mistress Brianna stood before me. " Greetings Mistress Brianna. I am your slave, slave william."

"Raise your head slave"

As I did so, I knew why I was there that night as her beauty was captivating and I truly loved her. She held no clothespins but she did hold a small whip in her right hand, which I immediately knew what it was for, but in her left hand she held a ball gag.

"Well done slave. Soon your trial will be over and the Ladies have agreed to allow you the release of screaming into the gag when necessary for the rest of the evening. Nita, put his gag on tight then full frontal suspension for the boy."

Nita took the gag and none too softly rammed it into my mouth and secured the gag tightly after shoving my head done. The Ladies watched all this especially when she pulled me to my feet by the clamps and for the first time I screamed into the gag. I was raised in full suspension for all to see. When Nita was told to remove the clamps, the Ladies watched with great interest my reaction to the removal to each as I screamed and struggled trying to comfort my nipples. Then Brianna approached and stood in front of me.

"Please william, prove to everyone that you are my slave. I will now remove all your clothespins with my pussywhip and none too softly. They are all watching your reaction to what I do so let's make it good."

I nodded and closed my eyes determined not to utter one more scream as the lashes started to land wherever a clothespin had been placed but most were on my cock and balls. I moaned and struggled trying to escape the whip until finally it stopped and I opened my eyes to a smiling Domme.

"Well done william," she stated and then turned to her guests. "There will be a short intermission before the Gallows Spin is presented. Will you please join me in a glass of Ice-Wine from my estate as the girls prepare the final entertainment of the evening?"

'What the fuck is she talking about,' I thought. 'Gallows Spin? Are they going to hang me?' I was then lowered to the ground and told to kneel as Nita and Karen busied themselves in preparation of what? My death? I was too exhausted to do anything even when the heavy bar was disconnected from the cable and placed behind me. When I looked down at my cock, I saw it hanging limply and knew that even Viagra would not be of use at that time. In amazement, I watched as Nita and Karen wheeled out some type of motor, which they connected, to the cable and then after plugging it in, tested to ensure it worked. Then the bar holding the chains to my wrist cuffs was attached to the bottom of the device and the whole thing was raised up taking me with it until I was suspended again. This time, they removed the spreader bar at my ankles and took it away as they lowered me to my feet. Karen then placed heavy leather cuffs on my thighs just above the knees and when both were buckled on tight; I was lowered to a sitting position. I felt numb all over and did not fear any further attempts at inflicting pain on me. A chain was then attached from each thigh cuff to the overhead bar and tightened until it appeared that I was in a sitting position with my legs spread wide apart as the cable pulled me up until I was about 5 feet above the ground level.

"Karen, let's test this out before the final hook up." Nita mentioned quietly and then picked up an electric cable attached to the device above me. What looked like a control box of some sort was attached to the cable that Nita started to run her fingers over.

First I was turned clockwise and then counter clockwise in full turns at various speeds and then jerked up and down as well. Satisfied, Nita then ordered Karen to prepare the last piece, which I watched from above. They carried a round heavy steel pole, which was over 4 feet in length to a position directly below me and screwed it into what I thought was a drain hole embedded in concrete at ground level. After they ensured it was in tight with no loose movement, Nita took a stainless steel cone from a box and started to screw that into the top of the metal pole. By this time, all of this was happening directly below my body so I got a good view of what was being done and what I thought would happen which kicked off a session of hard struggling on my part as I wanted no part of this.

Nita immediately grabbed the base of my balls, squeezed and punched the bag she held as hard as she could with her right fist which resulted in my screaming into the bag as all I saw then were shiny black spots in front of my eyes. "Stop it william or I'll keep hitting you until you pass out. Understood?" Nita asked.

I stopped but for two reasons one of which was the threat from Nita and the other was the fact that my body was all in. It could take no more as the suspension did me in and I knew that for the rest of this I would simply hang here in pain. I worked on trying to catch my breath as I took a closer look at the cone. Although it was hard to tell, the top was rounded and seemed to be about one half inch in diameter. This increased over its 10-inch length to a diameter of 2 or 3 inches at the base, which looked like 10 feet to me. Karen then covered all of it with a heavy layer of a lubricant and then putting a substantial amount on the tips of her fingers, started to rub my asshole with it. She chuckled as I squired trying to get away from her fingers, which suddenly ended up inside of me causing me to gasp and moan.

While my ass was being attended to, Nita had hooked up a CD player and quickly tested her chosen song for this fucking event of hers, which I hoped to repay in kind one day. I recognized the music immediately... it was 'When The Lights Go Out by The Black Keys'...and I knew that it's slow heavy beat would get all the Ladies excited but would cause me a lot of grief. The CD player was also attached to the control box for the device.

Nita had pre-recorded the first few instrumental bars of the song and now played it to get the attention of the Ladies to indicate that she was ready. I watched as the Ladies came and stood in a semi-circle around me about 5 feet away and saw Nita nod to Mistress Brianna as she turned the music off.

"Ladies, this is a short presentation that Nita came up with and which she calls the Gallows Spin. Slave william was not told of this until minutes ago and it is a good way for my slave to learn that he must always expect the unexpected. You may continue Nita." Brianna said.

"Thank you Mistress," replied Nita. "I hope that you enjoy the show which I call the Gallows Spin and which all males should endure for the Gynarchy Dominion." Nita then turned and proceeded to the control box and flip a few switches, which resulted in my body being lowered and guided by Karen onto the cone, which entered the first few inches of my asshole. I screamed into the gag at this penetration and at the same time notice that all the Ladies had joined arms and were watching intently this humiliation of my body.

The music then started and for the first minute my body was taken up an inch and down two or up two inches and down one inch all in time to the music. The Ladies, arm in arm, seemed to be moving to the music as well as best I could tell. I also overheard them yell out things like 'This should happen to all men', 'women rule', 'men are scum', ' long live the Gynarchy Dominion', with cheers and claps for the entire song. I knew that the bitch Nita would be rewarded well for this and there was nothing I could do as I just hung there screaming whenever I was penetrated in virgin territory.

For the second minute of the song, I must have been penetrated 3 or 4 inches as I no longer moved up and down but now was spun on the cone in small movements to the left and right.

Then the last minute...it was one in which I screamed for the whole minute it seemed. Not only did the spinning increase but also so did my movement up and down on the cone. I could only hear muffled roars of approval from the crowd and I knew that I was starting to loose consciousness with every beat and finally, with the song ending, the spinning stopped and my body dropped onto the cone; my weight driving it down as far as it could go. I then screamed harder than I ever had in my life and then passed out.

When I awoke, I was alone ... no one was there. Day had turned to night and the lights from the house and estate provided enough light that I could see where I was. Lying under the gallows structure, a blanket had been cast over my body by someone and looking around, there was no indication that a session of any kind had ever taken place. 'Was I dreaming this?' That thought changed when I tried to move and felt all the pains within my body. I was free of my bonds and gag, naked on the grass and had no idea what to do. Music and laughter came from the house but I wanted no part of that and struggling to my feet, headed off to the utility building where I had been prepared. I stumbled through the building and found my way to my car, which I quickly entered and wanted to start it but could not find the keys.

"Get out of the car boy!"

I looked up and saw Karen dressed in a white blouse and short skirt. No bra, God she's beautiful I though but knew I could do nothing at the moment.

"Did you hear me boy? Get out of the car now. Males must obey all females and that means you william. Now get the fuck out of the car."

Was I too tired to argue or did I now know my place in the group? Anyway I got out of my car and saw Karen holding out clothes for me to put on. Hey, these were mine! "Where did you get these from?" I asked.

"Just get them on and get in the car, I'm to drive you home and take care of you. Mistress Brianna was concerned for your well being."

I was too tired to say anything and grateful that someone would be driving me home. Karen parked to one side of the driveway, not choosing to enter or open the garage. Lights were on in the house and I knew that I had not left any on and then realized that they had taken my keys and prepared this sometime during the evening. After she got me into the house, Karen took me to the bathroom and made me get in the shower, which she entered with me. She washed me off, holding me close to her... she felt so soft and good and I knew that shortly my body would return to normal.

As water splashed over us, I heard a loud noise from the bedroom area. "What was that? Someone must be here?"

"Relax william. That was just the central cooling system or something. You've had a hard day. Let's dry off and get to the bed."

She gently towelled and dried me off kissing my body where it was sore or marked and then finally giving me a hard kiss on my lips with her tongue seeming to massage mine. Oh god, she is getting me excited.

Naked, we went off arm in arm to the guest bedroom, which had lights on, and I thought that Karen had done it. As we entered, I was astonished to see Mistress Brianna lying naked on the bed wearing nothing more than a black thong.

"Ah there are my 2 slaves now. You both look fantastic. Come here Karen and join me. Not you slave william. Your services will not be required tonight so get your ass to the Master bedroom now!"

My heart fell lower than it ever had on hearing her words and with head down, I went to my bedroom. It was dark so I naturally turned on the light and there on the floor of the bedroom was Nita!

She was naked with metal cuffs on her wrists locked behind her back and also on her ankles and drawn up in a hogtie position by having her long hair tied with rope that was tightly tied to her ankle cuffs. A gag contained her muffled screams as she watched me take in her beauty and as she realized what was to happen next.

Beside her was a small leather braided single tailed whip that looked like a miniature bull whip on top of a note. The note was from Mistress Brianna and simple said 'Remember william, always expect the unexpected.'

As I picked up the whip, my manhood returned with a vengeance and I knew from that point on that I would never fear the deep end of the pool.

  • COMMENTS
1 Comments
AnonymousAnonymousover 7 years ago
Bondage pleasure and pain

First off Mr William, thank you for this story! A nice (but rough) intro to consensual BDSM and Femdom, and I hope the vanillas don't run away screaming. A little pain never hurts, n'est-ce pas?

Always expect the unexpected!

Share this Story

Similar Stories

Femdom Between Friends Ch. 01 Office friends discover their darkest secrets are compatible.in BDSM
Wear the Collar Wife hires a pro to train her slut husband.in BDSM
Mistress Monique Discovering my need for a female led relationship.in Fetish
Breaking & Training a Man Ch. 01 A Domme has perfected her technique of breaking and training men.in BDSM
She Claimed Him Older dominant female claims her submissive male colleague.in BDSM
More Stories