The Wager Pt. 01

Hello, my name is Tom.

Lets start by me telling the world that I'm an idiot.

There it is, my big admission.

One reason for this self declaration is the bet I made with my best friend.

The bet was, could I meet a girl whom I could seduce, and convince to becoming my submissive, in one week or less.

The prize was nothing more than bragging rights.

We had a habit of making stupid wagers all the time.

Everything from when a pigeon would fly away, to how long it would take for a long freight train to pass the crossing we were stuck at.

Anyways, the first few nights after we set the wager, we began scoping out various hangouts, while I began flirting with girls that struck my fancy.

So far, I have gotten my face slapped a total of three times by three different girls, given five phone numbers that turned out to be fake, along with a lot of disgusted looks from others, and one enraged boyfriend who showed up out of nowhere, allowing me to discover just how fast my feet could take me in the other direction.

On the forth night we found a small pub that we had never been too before.

While we sat there, my eyes scanning the room, I was drawn to a girl sitting alone at the far end of the bar.

It was hard to tell how tall she was while sitting on her stool, but I would have to guess she was about five feet tall.

Atop her head was an unruly mop of strawberry blond hair, that fell to just bellow her shoulders.

Skin that was flawless, with a smattering of freckles that crossed her face.

Remembering to pick my jaw up off of the floor, I watched her shoot down at least four guys who had the balls to attempt to begin a conversation with her.

Everyone of them slunk away with their tails between their legs.   

My friend began nudging my arm urging me to take the chance, and go, and to speak to her.

Gathering my courage, leaving our spot, and ever so slowly shuffled my feet over towards where she was sitting.

As I neared her, every ounce of courage I had fled.

Halting my approach, I stood about five feet behind her, trying to get my feet to move, they on the other hand decided to cement themselves to the floor where I stood.

An onlooker would have surmised that I was lost in the wilderness, and wracked with indecision as what I needed to do to extricate myself from my predicament.

I have no idea how long I stood there like an idiot, but my guess was about three minutes.

Until the moment she turned her head, and looked directly at me.

Internally I was shaking like the proverbial leaf on a tree.   

Her gaze drilled through through my soul, with a single glance she leveled me.

Lifting her right hand, she made a single come here gesture with her finger.

With great effort, I willed first my left foot to move, followed by it's companion, until I was standing next to her.

As her eyes scanned me from head to toe, I felt like I had been placed on a slide, and slid under the lens of a microscope.

Parting her lips, this Goddess spoke.

"Well, what do we have here, a young man who would like to favor me with his presence.

So tell me, why would I even bother to waste my time speaking to such a pathetic creature as you?

Do you have any redeeming value as a human being, or are you just a collection of cells that came together in the shape of a person?

Well speak up, now is the time to plead your case!"

"I'm sorry for disturbing you, I'll leave you alone, and not bother you any longer."

As I turned to leave, shot down like all those before, I heard her command me to stop where I was.

Halting my retreat, I turned back to face her, my feet moving on their own pulling me towards her.

When she patted the stool next to hers, I sat awaiting her next words.

"OK, young man, tell me about yourself, and why I should even bother to continue this conversation.

From you I want absolute honesty or you can head back from whence you came.

You can begin to plead your case now."

Over the next twenty minutes or so, I told her about myself, and the wager that my friend hooked me into playing.

When she asked about the courses I was taking at the university, I told her that I was studying to get my degree in electrical engineering, along with my minor in psychology.

"What makes you think that you have what it takes to take on the role of a Dom?

The little man I see sitting before me, doesn't appear capable of that type of lifestyle, if anything you might be good material for being someones submissive.   

When you walked up behind my seat, I watched you in the mirror behind the bar, if you were as confident you thought, you wouldn't have stood frozen in your tracks."

"No you are correct, I'm not really a Dom, it's just that those were the terms of our wager, to tell the truth, I never had any luck with finding girls to date, let alone playing in the D&S world.

In reality, one of the reasons for this is my lack of confidence is, well, I'm not very big down there if you know what I mean.

The last time I managed to find a girl that I began dating, we went back to my place after the third date, and when we undressed, she looked at my shortcomings, and began laughing at me.

Needless to say, that managed to kill the mood, followed by her dressing, and walking out.

She never returned my calls or emails.

So that in a nutshell is my pathetic dating history."

While I had been telling her my story, I tended to keep my head bowed, not making eye contact out of fear that I would see the same old look of disdain on her face.

What I wasn't prepared for was her reaching out, placing her fingertips gently under my chin, while, lifting me up to look directly into my eyes, and lightly stroking my cheek, along with a look of compassion across her face.

At that moment I turned my face away from her gaze as a tear began to fall from my eyes.

The hand that before stroked my cheek, turned my head to face her.

Her fingers reached out to wipe away those few tears that rolled down my face.

"Tom, I want you to go over to your friend, and tell him you have just won the bet.

Tell him that he is in his own for tonight, and that you were going home with me."

Sitting there with a stunned look upon my face, I listened to instructions, while nodding my head.

With her permission, I left the bar stool, and headed over to my friend to repeat what I was ordered to say.

Before I turned to leave, he offered a high-five, and congratulations on winning the bet.

I didn't tell him that the terms of this wager had be turned around, as my pickup was now in control of the night.

Following her out of the pub, we walked to the end of the block, turned right, and stopped at a very expensive high-rise condo building.

Swiping her key card on the door, we entered the lobby where she greeted the guy at the desk as we strode past to the elevators.

Inserting a key on the panel I discovered that we were headed to the penthouse apartment.

As the doors closed, she turned towards me making her apologies for not making a formal introduction before.

"Dear me, I'm not being a very good hostess, I didn't tell you my name, so let me rectify that right now.

My name is Jane, however while you are in my home you will address me as Miss, or Mistress, is that clear?"

With a nod of my head, I acknowledged her demand.

"Tom, when I speak to you, you are to answer me properly, a nod of the head is disrespectful and an insult that will not be tolerated, is that understood!

I want you to understand that you are entering into a D&S relationship.

I am not a harsh Mistress, nor am I cruel, but I do expect that you will learn to become a more assured, and self confident young man, while under my tutelage.

In addition, you need to have faith, that I will not cause you undue pain, or hardship.

You will have a set of safe words that will slowdown, or completely stop any action on my part.

Please take a seat at that table, I want you to take your time, and ask me any questions that you need to."

Forty minutes later, with many questions asked, and answered, I was satisfied that I had not walked into the home of a mass murderer.

Rising from the dining room table, I was asked to follow through her home to a door at the end of the hallway.

Swinging the door open, I was greeted by the sight of a BDSM playroom.

Although the lights were set to a low level, I could see well enough to recognize many of the objects in this room.

Against one wall, was a St Andrews cross, nearby was a spanking bench.

In another corner a medical exam table, stirrups and all.

Against the opposite wall there were a set of ropes hanging from above with leather cuffs for both arms, and legs.

Everywhere one looked, there were objects designed for securing a person in place.

"OK young man, remove your clothes, and hang them on those hooks to your right.

When you are done, kneel before me."

Turning away from her, I removed my clothes, and hung them as required.

Returning to Mistress, I knelt at her feet, my hands upon my thighs.

Touching me on my shoulder, I was told to rise.

Reaching out, she began to run her hands along my body inspecting each inch of my body.

When she reached my cock her fingers began to stroke it causing the inevitable, as my cock rose to it's full glory of three inches.

"I want you up on that table over there, face up, legs spread wide."

Moving from one arm to the other, she secured my arms, and then my legs to the corners of the table.

"Now young man, I do not like having my subs crotch covered with hair.

This is something I will remedy now, and for the future, you are to keep yourself shaved smooth, is that understood."

My response was to answer her with,

"Yes Mistress."

From a nearby drawer she produced both an electric trimmer, and a razor, along with a can of shaving cream, and a bowl of water from a small nearby sink.

Running the trimmer over the hair on my crotch, I watched as the hair fell away from my body.

I could hear the hiss as the shaving cream poured forth from the can.

When she spread the handful of shaving cream on my crotch, and penis, the cold came as a bit of a shock.

Seconds later, the cold hard edge of the razor began it's journey through my pubic hair.

Lifting first my balls, followed by my penis, she very quickly, and efficiently removed all the hair, leaving my bald as a young man.

This was followed up by a damp washcloth to clean up any remaining cream from my crotch.

With her fingertips, she began to tease my little cock to full hardness.

When she was satisfied, her breath blew across my cock, causing it to begin throbbing, along with pre cum beginning to flow from the tip.

When at last her lips closed around the head, my body jerked upright, yet my movement was limited to the slack in the bonds that held me fast to the table.

Over, and over she teased my little cock, pulling her lips, and fingers away when she felt I was nearing a climax.

Moments later, she undid the bonds holding me, while having me lay face down on the table.

After re-securing me, I waited to find out what she had in store for me next.

I didn't have to wait much longer to learn the answer to my thoughts, as I heard the whistle of air being displaced as a paddle landed squarely on my bottom.

Over and over the sting of the paddle shot through my bottom, and radiated throughout my body.

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 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 Mistress legs began shaking, along with her hands pressing my face harder into her pussy.

Lifting her dress, she pushed my head away, as her face underwent a transformation while 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 knees 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, 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 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 tormented me with denial.

I was almost afraid of doing internal damage when I was 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 man, cum for me now."

The orgasm that 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 man, 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 fashion 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."