When she was on the verge of her next climax, I pulled away, and moved forward to line my penis up with the gates of heaven.
What followed wasn’t making love, it was nothing more than raw unbridled fucking.
To those around us, what they heard was the wet squishing sound of our bodied covered in sweat, as our hips slapped against each other, along with the sound of my penis slipping through Jill’s soaking wet pussy.
“Jill, I’m cumming, cum with me, cum with me NOW!” I yelled.
Jill climaxed first, followed by my orgasm seconds later.
Stabbing my penis deeper into her body as my balls emptied themselves deep into Jill’s body.
Falling away from Jill, I rolled onto my back, it was then that Jill leaned over my worn out body, and began kissing me with an ardor, I wouldn’t believe possible.
Returning the kiss, I decided that I was falling in love.
As we lay there Mistress came forward, and took the two of us in hand.
Leading us to a side room, we were told to crawl into the bed, and rest for a bit, that she would return to collect us in about an hour.
Pulling the covers over us, Jill and I began talking about what was happening to the two of us.
“Jill, I have to admit that when Mistress pulled the hood from your head, I almost fell over from the shock of seeing you underneath the hood.
What ever prompted you to turn yourself over to Mistress’s control?”
“Tom when I discovered that you were wearing a chastity cage, I was at a loss for words if you recall, well at least for the first few moments.
However, my curiosity quickly got the better of me.
I wanted to understand why a person would relegate control of their lives to another.
As I mulled over these questions, I thought back to the Tom I knew.
The Tom I knew was a bit of a jerk, who would go to the pub trying to pick up woman with a cocky attitude, and in some ways very misogynistic.
Yet after we talked the other day, I witnessed a different Thomas, someone who was more demure, introspective, and thoughtful.
I wanted to understand how this happened.
So it was that I called the number that you gave me.
That very evening, I called your, now our Mistress, and arranged a meeting with her.
She agreed to meet with me the next morning.
I admit that I was frightened to meet with her, I had no idea what to expect.
Was she some kind of monster who had you under some type of spell, or was she manipulating you via psychological trickery?
What I discover was an incredibly kind, and thoughtful person.
Not only did she answer all my questions with complete honesty.
At the conclusion of our meeting, she asked me to think over what we discussed, and if I was still intrigued, that I should come back later that evening and she would start me on my journey.”
While I thought over all that Jill had just told me, Jill moved closer, and wrapped her leg over my hip, drawing us closer.
Leaning onward Jill began delivering a series of soul shaking kisses.
The passion embodied in those kisses drew me inward, a moth to a flame.
During the next few minutes we bound our souls together in the simple act of sharing those kisses.
As Jill’s hand slid downward,
cupping my balls, and penis with a hand heated to a volcanic level.
If I thought I was spent from my previous orgasm, I was sadly mistaken.
As Jill stroked my penis, I reached between her legs, and began to diddle her clit, not enough to make her cum, just enough to cause her to clamp her legs, trapping my hand in place.
Tossing the covers back, Jill slid down the length of my body to take my penis between her lips.
I was now on the receiving end of a Bj that caused my eyes to roll back in my head, while my toes curled.
Over, and over Jill took me to the edge, and then backing off, driving me crazy.
In the midst of this Jill reached underneath me, and began worming her finger into my bottom.
As she twisted the finger around, I began to see stars, as she rocked my world.
Pulling her away from my penis, I lifted her up, and resumed kissing those wonderful lips.
Pushing me away, Jill said, “Tom, I need you to fuck me, and fuck me hard.
I don’t want soft, I want rough, and sweaty sex, make me scream.”
Flipping her over, and pulling her up to her knees, grabbed her by the hair, as I drove my penis into her in a single violent thrust.
From the depth of her soul, came a moan that began low, and grew in intensity until the walls of the room began to quiver from sympathetic vibrations.
“Fuck me Tom, fuck me harder, I want my pussy to feel sore for days.”
Pulling harder on her hair was driving her to the edge.
Pounding her as hard as I could, she began the journey towards her orgasm.
Moments before she climaxed, I spit on her rosebud followed by driving a finger deep inside her bottom.
The moment I began to swirl it around inside, her body began to shake uncontrollably.
When at last her orgasm overtook her, she emitted a loud moan, followed by a whimper that overshadowed the sound of our fucking.
Followed by Jill collapsing face down upon the mattress.
My immediate reaction was to fall in beside her, and draw her into my arms.
The next few minutes were spent by the two of us kissing, and grinning like a pair of fools.
Closing my eyes for a minute to gather myself, found me opening them again to daylight streaming through the windows.
Jill was wrapped around me, spooning as we slept.
Seconds later there came a knock upon the door.
Without waiting for a response from us, the door swung open, revealing our Mistress entering the room.
Well, well, well, what do we ave here, a pair of my subs wiping the sand from their eyes.
After last nights party, I came to fetch the two of you, and bring you home.
However, when we looked in the room, we saw how peacefully the two of you looked wrapped around each other while sleeping.
It was then that our hostess suggested that the two of you, and myself stay, and spend the night here.
That was fine by me, as I was a bit drunk.
On the plus side, Suki and I spent the night together.
That woman is a smoking cauldron of sexuality, I’m no amateur, but Suki wore me out, I don’t know if I’ll be able walk right for a couple of days.
OK now, the two of you get dressed, and we’ll go out for some breakfast.
Tom before you get dressed, I need to lock you up, please come over here.”
Reaching into her purse Mistress removed my cage, and began pulling first my balls, followed by placing my penis inside the cage.
Once this was accomplished, Mistress attached the padlock.
Effectively making my penis out of commission.
“Jill, come over here, I haven’t forgotten about you.
I have a gift for you.”
Reaching into a bag, Mistress removed a smaller package wrapped in silk.
Handing it to Jill, she asked her to open it.
With the gift unwrapped, Jill held out a leather chastity belt.
It looked like it was made of a very soft suede like leather.
The under strap had a stainless steel plate with a hole in the center.
“Mistress, you don’t expect me to wear this thing, do you?
I mean, it’s archaic, woman haven’t been forced to wear these in a hundred years!
Besides, how am I supposed to go through my day with this contraption strapped around me?”
As Jill was speaking, Mistress’s face turned stern.
Taking Jill by the wrist, she pulled her across her lap, and began spanking her bottom.
There was nothing gentle about this spanking, it was done to exert her will over that of Jill’s.
Somewhere around the thirtieth spank, Jill gave up, and told Mistress that she was sorry for questioning her decisions, and sorry for talking back.
Returning to the task at hand, Mistress began fitting the belt around Jill’s waist.
Once the belt’s width was adjusted, Mistress reached between Jill’s legs to pull up the center strap.
Once in place, Mistress slipped the strap in place, and snapped the padlock in place.
“OK, now the two of you can continue dressing.
By the way, if you check the closet over there, you will find some clothes I picked out.”
Jill, and I opened the closet to find two sets of clothes ready for us.
For myself, I found a pair of nice slacks, a polo shirt, and a new pair of shoes.
How she managed to figure out my size for the clothes, especially the shoes was beyond me.
As for Jill, Mistress had picked out an outfit, that looked like a Catholic school girls uniform.
Knee high white socks, saddle shoes, a short pleated skirt, along with a starched white button down shirt.
Once we were dressed, we checked ourselves in the full length mirror.
The fit of the clothes was perfect, I should have Mistress go through my closet at home, and weed out the worst of my clothes.
Turning towards Jill, I saw standing in front of me, every man’s dirty fantasy.
Her outfit drove every man to wonder if he would every stand a chance in having such as her, if even for a second.
From downstairs, we heard our names being called.
Shutting off the light as we rushed out of the room, and flying down the stairs, we found Mistress waiting for us.
She was dressed in her signature Victorian style dress.
Today the dress was a light blue crushed velvet, with a paisley pattern.
As we left the house, a limo was waiting for us just outside the front door.
As the chauffeur held open the door for Mistress, she beckoned for us to sit on either side of her.
As the driver took off, I asked Mistress where we were having breakfast.
Her response was short, We are having breakfast at Suki’s home.
Fifteen minutes later, we arrived at another mansion.
This place was even larger than the house we spent the night at.
Awaiting us at the front door was a man, and a girl, both were dressed the part.
The man was outfitted like a classic butler, the girl was dressed as the perfect French maid.
Welcoming us into the house, we were shown to the dining room.
Rounding the corner, we entered the dinning room only to find that others had been invited to this repast.
I counted five other woman mulling about waiting for the meal to be served.
The second I formed these thoughts, a bell rang announcing that the meal was about to be served.
Each of us was directed to our seats, as a cart was wheeled out from the kitchen.
All those present waited for our hostess before sitting.
It was only a few moments before Suki made her entrance.
What an amazing looking woman, Suki was dressed in a magnificent Kimono, pure white, with a cherry blossom motif, her Obi, was pink with white stripes.
Once Suki sat, her guests were permitted to take their seats.
What struck me as odd, is that Jill, and I were the only subs present.
The two of us knew that we were to keep our mouths closed unless we were asked a direct question, or told to speak.
As we sat there, we listened to the ladies talking about everything from the weather, an assortment of risque jokes, to their gripes about ever day life.
As the meal concluded, we rose from our seats, while Suki led everyone to her living room.
As everyone filed into the other room, Jill, and I were told to stand in the middle of the room.
While the ladies found their seats, the butler, and the maid we met earlier, came in through a side door.
Suki was the first to speak.
“My friends, I have gathered you here this morning to help initiate Mistress Jane’s new subs.
Mistress Jane, do I have your permission to put your subs through some, shall we say tests, if so may I have the keys to their chastity devices?”
It was now Mistress Jane’s turn.
“Why yes, Suki you may.”
Reaching into her blouse, Mistress produced the keys in question.
Handing the keys to her servants, Suki asked her maid to undress me and unlock my cage.
The second key was handed to her butler with the same instructions.
The maid was a tiny slip of a girl, no more than five feet tall, if she broke a hundred pound it would be amazing.
Starting with my shirt, she undid each button with agonizing slowness.
As each piece of my clothing was discarded, my anticipation grew.
When at last I was naked, I looked around the room, and discovered that I was standing naked in a room full of starving wolves, judging by the looks upon their faces.
Turning back to the girl in front of me, I watched as she removed her clothes.
My god, she looked even smaller naked.
Reaching out, she took the key, and unlocked my cage, followed by her removing the ring that held it all together.
From a side table she produced a washcloth, and a small basin of warm water that she proceeded to use to wash my genitals.
With her hands on my little penis, I quickly rose to the occasion.
Looking over at Jill, I saw that she was receiving the same treatment.
What shocked the hell out of me was the moment the butler removed his clothes.
When he dropped his boxers, Jill let out a gasp that caused me to scan downward.
Everyone has heard the expression “Hung like a horse”, well this is the horse that everyone talked about.
Even flaccid, his cock had to be ten inches long, and thick as hell.
Taking Jill’s hand, he placed it upon his cock.
Jill looked almost afraid to touch this monster, yet as the seconds ticked by, she began stroking his cock.
As it rose to the occasion, Jill’s face underwent a transformation, from fear, and uncertainty, to joy, and anticipation.
Source: reddit.com/r/Erotica/comments/xtpd5y/mf_the_wager_part_7_bdsm_chastity_18