[M/F] The wager [Femdom] [Part 2] [18]

Halting the paddling for a moment, she began to lube up the little hole in my bottom.
The next thing I knew was her inserting something like a plug into my bottom.
What really blew my mind was when the plug began expanding inside my bottom.
With each pump the plug expanded more, and more, until I had felt fuller than I had ever felt before.
When my body began to cramp up, I used my safe-word, “Yellow” to tell her I couldn’t take any more of the plugs inflation., at which point she halted what she was doing.

“Tom, how are you doing?
I hope you are willing to continue our little drama, I have so many ideas percolating through my head right now, that it would be quite the shame to waste them.
If you are ready to continue, please let me know.”
I gave Mistress the go ahead, and that I had recovered from the intense feeling of having my bottom inflated with the butt plug.

Returning to the plug in my bottom, she began to re-inflating it, but to a lesser size.
Once she was satisfied that I wasn’t in too much pain, the paddle returned to pummel my bottom red, and throbbing.
Over, and over it fell across my bottom, as I counted out the number of impacts upon my bottom.
By the time the count reached thirty, Mistress withdrew the paddle, only to switch over to only using her hands.
The sting of her hands accentuated the throbbing that was left over from her use of the paddle.

Releasing me from the bonds that held me fast to the tabletop, she had me stand, and face her.
Reaching over to a small stand, Mistress took a long leather leash with a soft looking loop at one end.
Taking my little penis, and balls in hand, Mistress wrapped the loop around the base of my cock, and balls.
I was now being led around the room on a leash, attached to my nether regions.
If I slowed down, Mistress would give a yank on her end of the leash.
This had the effect of getting me to pay attention to my pace, and speed of movement.
Three or four laps around her playroom, and I was ready to follow her without any slips in my attention.

While in the middle of the room, Mistress pushed me to my knees, followed by her lifting the hem of her dress, it was now that I discovered that she wasn’t wearing any panties, and that her pussy was shaved smooth.
Pulling my face between her legs, I knew what required of me.
As her dress fell over my head, I was now in the darkness that allowed my imagination to run wild.
At the first touch of my tongue to her pussy, Mistresses legs clamped around my head holding me tightly in place as I worked her pussy into a dripping mess.
I could tell she favored my skills, by the sounds emanating from deep within her.

In only moments Mistresses legs began shaking, along with her hands pressing my face harder into her pussy.
Lifting her dress, she pushed my head away. Her face underwent a transformation as her climax took over her body.
Minutes later, she had regained control of herself, and began to applaud my skills.
“My, My, my, you have really proven to be a most excellent oral provider.
I am very pleased with what your tongue, and lips can do, to that end I think you are to be rewarded.”

With that, the leash around my cock was pulled upward, causing me to rise from the floor, and to follow where Mistress was leading me.
Standing me in front of her spanking bench, I was instructed to lay face down upon the bench.
A quick description of this bench.
Think of a sawhorse that was padded, and covered with plush leather.
There was a lower set of padded arms that a persons legs could rest upon.
To cap it off, there were sets of restraints for each arm, and leg, along with a wide leather strap that is used to secure your waist tightly to the top of the bench.

Once I was strapped down, I discovered that my body was for the most part immobile.
I could move my wrists, and feet, along with lifting my head a bit.
From behind, Mistress began lubing up my bottom again.
I feared that she was going to use her inflatable plug once again.
Minutes later I was proven wrong, as she walked in front of me.
What I beheld, was Mistress naked, and wearing a strap-on dildo.
My first thought was “Oh shit, I don’t think I could take that thing.”

From behind, I felt Mistress probing around my little hole.
As she zeroed in on her target, the head of the strap-on began to push inward.
My hole began to open wider, and wider, as she slid her strap-on into my bottom.
Ever so slowly I was being stretched open wider, and wider.
I couldn’t believe I was able to open that wide without being torn apart.

Once fully seated in my bottom, she began to establish a rhythm, starting with long slow strokes, alternating with wild, and hard thrusting, my bottom was feeling the impact each time she would slam the strap-on deeply into my bottom.
To drive me even further into madness, Mistress reached underneath my body, and took hold of my little penis.
Each time she pushed forward, my penis would slide between her fingers.
Mistress had an uncanny ability to sense when I was close to cumming, she would stop holding my penis until I calmed down a bit before beginning again.
Over the next fifteen or so minutes, Mistress pounded my bottom, while keeping me edged to the point of exploding.

When she thought I was ripe, Mistress released me from my bonds, and had me lay back on a nearby bench.
As I lay there she slid a smaller dildo into my bottom, as she leaned forward, and wrapped her lips around my cock.
The pure heaven I was now experiencing was short lived, as she switched to using her hands alone.
Taking me to the edge over, and over, she tortured me with denial.
I was almost afraid of doing internal damage when I finally allowed my orgasm.
With the dildo running in and out of my bottom, she zeroed in on hitting my prostate with the head of the dildo.

Pressing the dildo hard against my prostate, Mistress squeezed my cock hard, while giving it a few last strokes.
“Cum for me my little boy, cum for me now.”
The orgasm the blasted through my soul, was unlike anything I had ever experienced before.
Rope after rope of cum poured out from somewhere within my body, covering my face, and chest.

Allowing me to cool down, Mistress left the room only to return a few moments later with a basin of warm water, and a couple of towels.
Taking the towels, she washed my cock, and balls.
Just her handling my penis was beginning to cause it to harden once again.
To prevent this Mistress flicked her fingertip against my balls, causing my little erection to fall by the wayside.
“Now my little boy, I want you to lay back, and keep your eyes closed.
If you peek, you will be severely punished, is that understood?”
Giving her my agreement, I lay back with my eyes clamped shut.

What I felt, was her holding my balls up while pulling them and my cock through something cold, and metallic.
Followed by my cock being surrounded by a similar metallic item.
What really caught my attention was the sound of a very solid “click”.
“OK my boy keep your eyes closed, and reach down with one hand, and feel what I have done.”
Reaching down with my right hand, I encountered a metal object surrounding my cock, along with a large metal ring that encircled my balls.
I was now told to stand, and face the full length mirror on the wall next to me.

OK now I know what was what, Mistress had locked my cock, and balls in a chastity cage.
This one had the look of an old fashioned birdcage with a downward bend.
It wasn’t uncomfortable, but you knew you were wearing it, every time you moved, it would remind you of it’s presence.
Giving my hips a little wiggle, I watched as my cage swung side to side.
It was at that moment, I discovered another aspect of a chastity cage, if I began to get an erection, the cage prevented that with a dose of pain as the cage asserted it’s dominance.
“Mistress, I have an appointment to go to an hour from now, I love this cage, but I need to be going soon. May I have the key please.”

“My boy, maybe I should have been clearer in my intentions.
You are to wear this cage until I decide to remove it.
Now since you are new to all of this, I will see you tomorrow at three pm.
So be here tomorrow, and we will talk about what is going to be expected of you from here on out, is that understood?
Now get dressed, and ready for the rest of your day.”

Once dressed, I was ushered out of the penthouse, and into the elevator.
As the door closed, Mistress blew me a kiss, and a wink.

Source: reddit.com/r/Erotica/comments/wpyn1m/mf_the_wager_femdom_part_2_18