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.
Once this monster had reached it’s full potential, Jill dropped to her knees.
While the minutes ticked by, Jill began inspecting her prize, lifting his balls, to feel their weight, and heft.
When her attention focused on the cock in front of her, Jill ran her tongue along the crown, causing it to twitch in response.
Looking back towards me, Jill smiled, and winked.
Turning back, Jill opened her mouth, and took the tip between her lips.
Try as she might, Jill could get no more than the first couple on inches in her mouth.
Reaching down, the butler lifted Jill from her kneeling position, and carried her over to the coffee table in the middle of the room.
Placing her face down upon the table, her knees on the floor, he beckoned for me to come over to the table.
Telling me to hold her arms stretched above her head as she lay across the table, a task that fired my imagination, and kept my little penis rock hard.
As he knelt behind her, he began running the tip of his cock along the length of Jill’s slit.
While this was happening, I kept my gaze locked on Jill’s face.
Each time he swiped his monster along her pussy, her eyes began losing their focus.
When at last he began to press forward, taking his time to open her up, each minute thrust found him going deeper than the last.
With every inch of ground he plowed, Jill’s eyes began rolling around in his her head, followed by a deep groan emanating from the bottom of her being.
It took about five minutes for him to get most of his cock seated to the deepest depth of Jill’s pussy.
This still left about six or so inches of his cock outside of Jill’s body.
The moment he began in earnest, Jill’s body began sliding back and forth upon the table.
After the first few seconds, I could tell that Jill was no longer on this or any other planet in our solar system.
With every thrust, Jill would moan in a mixture of pain, and pleasure.
Beads of sweet ran down her face only to drip onto the table below.
Before he or Jill could climax, Mistress called out telling him to stop.
He withdrew his cock, and stepped away from the table.
The second Jill realized that she was going to have her orgasm unfulfilled, she cried out in frustration, begging him to come back.
Releasing my grip on Jill’s arms, I moved around to the back of the table, and took Jill into my arms, holding her tightly as she came back down to earth.
When at last her breathing returned to normal, she tried to focus her eyes on her surroundings.
Finally turning her head towards me, Jill pulled me down for a deeply invasive kiss, a kiss that found our tongues twisting around the others.
Breaking away, Mistress ordered me to take Jill’s place upon the table.
As I lay face down on the table, my legs were strapped to the legs of the table, a strap was wound around my middle holding me fast to the top of the table.
Jill was told to take, and hold my wrists above my head.
Watching Jill’s face, I witnessed a smirk develop, and spread across her face.
Within seconds I felt what caused her smirk, as Suki’s maids hand landed across my bottom.
Over, and over her hand slammed into my bottom.
I couldn’t believe that such a tiny girl could deliver spanks of such intensity.
Moments later there was a break in the spanks I had been receiving, within seconds I learned the reason for the break as she switched over to a leather belt.
After twenty swats, the belt was retired, in it’s place were the hands of my tormentor.
This time however, those same hands began rubbing lotion into my sore bottom.
As my bottom was being soothed, Jill leaned inward kissing my lips, and face.
Seconds later, the straps binding me were released, and I was flipped onto my back.
I next discovered this table had a secret, as a pair of stirrups were attached to the sides of the table.
My legs were raised, and strapped onto them.
On my back, my legs in the air, Suki’s maid returned.
This time she had a strap-on affixed around her waist.
As a large amount of lube was slathered on, and into my bottom, the girl moved into position, her new penis looked monstrously huge.
When she began pressing against my little hole, I began gasping for breath.
After a few minutes, she had breached the hole in my bottom.
Starting slowly, the strap-on began sawing inward, the feeling this generated was beyond anything I had ever felt before.
Seconds later ten pairs of hand began caressing my body, as all of Suki’s guests got in on the action.
When at last someone touched my little penis, I almost launched myself off the table.
Between my bottom being hammered, the ladies touching me, I didn’t think I was going to last very long.
That feeling was reinforced seconds later when Jill moved from holding my wrists while being fucked by the butler to climbing atop the table, and disconnecting from the monster that was stretching her beyond anything she had ever encountered.
Seconds later, my vision was cut off as Jill knelt above my face, her bare pussy hovering above my lips.
As she lowered herself, my tongue probed upward to taste her ambrosia.
Slipping my tongue between those lips, brought a loud moan deep from Jill’s soul.
With all those hands touching my body, along with my bottom being plundered, and Jill’s pussy dripping it’s nectar onto my lips, I wasn’t going to last very long.
Wen my body began shaking from it’s impending climax, a voice in the background called a halt to the proceedings.
All the hands along with the maid pulling her strap-on out of my bottom, and finally Jill slipping off the table, left me alone, and gasping for breath, my orgasm denied.
Laying there the shaking of my body ever so slowly dissipating, leaving me a broken husk.
Minutes later, my legs were unstrapped from the stirrups that held me open, I was helped off the table by Suki.
She led me off down the hall, and led me into the nearest bathroom.
Once inside Suki helped me into the shower stall.
Still holding me upright, Suki began washing my body starting at the top, and working downward. When I was at last able to stand on my own, I turned Suki around, and returned the favor.
I loved washing her body, so thin yet curvy in all the right places, her small breasts were a delight to tease, and play with.
When I slipped my soaped up hands between the cheeks of her bottom, Suki gave a small gasp as I wormed a finger deep into her little hole.
Reaching around with my other hand, I began my assault on her pussy.
The fingers of my left hand sliding in and out of her bottom, and those of my right hand thrusting into the depths of her pussy, Suki began huffing, her breath becoming ragged as her body convulsed in its orgasm.
When at last her climax overtook her, she began to slump towards the floor of the shower stall.
Holding her tightly, we slid downward only to rest upon the floor, the warm water cascading down upon our bodies.
Her senses once again working, Suki took her hands, and pulled me into a deep kiss.
Moments later we stood, and dried each other off.
As we stood there, Suki reached into a pocket of her robe, and produced my chastity cage.
Seeing this brought a groan from me.
Reaching down, Suki began fitting the cage back onto my penis where it belongs.
When the cage was in place, I turned to look in the mirror.
This is me naked, my penis caged, my body used for the pleasure of others, and truth be told, I loved it.
Taking me by the hand, Suki led me back into the main room.
As we turned the corner, I discovered that all the others were gone with the exception of Mistress, Jill, and the servants.
Looking around the room, Mistress told Jill, and myself that she had sent them away until later that evening when she was hosting a private dinner for a select few.
“Now I want the two of you to go home, and wait until tomorrow when I will need both of you to meet me at the address on this calling card.
You will be there at seven pm on the dot, if you are late, you will be severely punished, is that understood?”
While she was talking I saw Suki fitting Jill with her chastity belt.
Once the lock was in place, we were told to head upstairs, and get dressed.
When were done her chauffeur would drive us back to our dorms.
Twenty minutes later we sat in the back of the limo as we were driven home.
During the ride back Jill, and I kept silent, both of us were lost in our own thoughts.
I could imagine that Jill’s thoughts were pretty much in line with mine.
IE, what were doing mixed up in this lifestyle, how did we get here, how far are we willing to go in this odd relationship with Mistress?
After being dropped off, Jill and I retreated to my room.
Stripping off our clothes, we crawled under the covers of my bed while cuddling each other.
“Jill, what are you thinking.”
“I’ve been thinking about my relationship with Mistress.
Where is this going, how far am I willing to go to please Mistress?
Among everything else, I’m beginning to discover the changes in myself, that my relationship with Mistress has wrought.”
“Jill, I know, I have been thinking along the same lines.
I’m seeing changes in myself that I never even considered.
I never thought that I would do the things that I have done in the last couple of weeks.
A year ago if you asked me if I would allow myself to be fucked by a girl with a strap-on, I would have laughed in your face.
As to myself becoming a submissive slut boy, only fit to be used by others for their pleasure, I would have argued with you that I wasn’t in any way submissive, in fact if anything, I was an Alpha male, and would never allow myself to be anything other than that.”
While we lay there under the covers, Jill began playing with my cage causing my little penis to attempt to escape it’s confines.
Since that wasn’t about to happen, my cage exerted it’s will.
As the cage did it’s thing, I was forced to pull away from Jill ministrations, or suffer extreme pain.
I turned my attention towards Jill’s chastity belt.
While I couldn’t penetrate the metal plate that covered Jill’s pussy, I could press the belt against her pussy, creating a small amount friction against her clit.
Within seconds Jill pushed my hands away as she began the journey towards an orgasm.
“Tom, as much as I want to make love to you, please don’t make me cum.
I would have to tell Mistress that I had an orgasm that she didn’t control.
I don’t want to take the chance that she might keep us apart because I disobeyed her.
The truth is, that I have discovered that I have begun having feelings for you.
The funny thing is, that before we met Mistress, I wouldn’t have given you a second thought.
I saw you as a creep, who had a strong misogynistic streak.
Yet the more time we spent together, I was amazed at the changes that Mistress has drawn out of you.
Now I see a man who has discovered his softer, and more thoughtful side.
All that I saw in the man who was, is no longer within you.
It was all a bullshit cover for your fears, and insecurities, those have been stripped away exposing the real person behind all the other crap.”
As Jill finished her little speech, something inside of me broke.
Tears began streaming from my eyes, followed by my beginning to sob like a child.
The truth of who I was hit me hard, causing my heart to open itself to my personal truth.
Jill pulled me closer, and brought us face to face, where she began kissing away the tears that fell from my eyes.
Whispering in my ear that she loved me, renewed those same tears.
While girls have said that to me in the past, I never really believed them.
This however was vastly different, for the first time in my life, someone really cared about me.
As we drifted off to sleep, we held onto each other, hoping that when we awoke, the other would still be there.
Source: reddit.com/r/Erotica/comments/yggfbe/mff_the_wager_part_8_chastity_bdsm_18