My Second Greatest Challenge free porn video

Copyright© 2001-2003

A pathetic old maid of Bordeaux
Fell in love with a dashing young beau.
To arrest his regard
She would squat in his yard
And longingly pee in the sneaux.

I've had three primary sexual relationships in my life, up to this wild juncture.

The first, Erika, was a girl whom had come from a nasty household. Drunk mother, physically and sexually abusive father. Her claim to fame to me was that she was the first girl to spread her legs. She was also the first girl whom I had discovered my pleasure in sexually commanding another person.

I was like a child in an unknown world at that point.

Erika ran away from her family and me five months after the first time I sunk my dick into her, to the day. The rumour mill said she was selling her ass for hits of heroin on East Hastings, in Vancouver.

The second was Camile, beautiful and a very sexy sixteen year old who was also as dumb as an ox. And as such, it was for me a time of sexual discovery; where I was able to experiment with many of the sexual deviant ideas that came upon me. I used and abused that beauty, till my dick was tired of her stupidity and I came to realize she was not a 'true' slave, only an ox.

It was my first taste of desiring a 'natural' submissive and not just a woman or girl who played games.

It was the third that truly allowed me to grow as a dominant - who was truly my slave. Georgia, dark haired and long legged. She was smart, sexy and submissive. We lasted for over a year, when she moved away to go to University. She cried upon my shoulder at the airport, begging me to command her to stay - but I loved her enough to let her go.

Deep huh? I still can not fucking believe I let her go.

That leaves us here and now. A Master with no slave.

There were girls that I rather liked, but none I found that would submit to me how I wished. I wanted full trusting submission from a woman - a virgin to her slave-side, who I could push toward a lifestyle she may not even have imagined but whom was destined for.

Months after Georgia had left, I was still a lone Master.

I went to school, the local College, and lived at home that first year out of High School. It was a year of discovery of how far I would allow my desires to push the envelope of what society would accept.

And it started here...

It was the last thing I would have ever expected to find in my grandmothers bedside table.

I sat down stunned and starred at the object in my hand, the phone forgotten for the moment.

"Hello?"

The caller, "Yes... I'm still here?"

"Did you get that number I gave you James?"

"Yea... yes madam I did." I barely heard her, and most certainly did not take down anything she had told me. Just one of grandma's stupid friends - the old bat would forget she had phoned and left a message regardless!

"OK, tell your grandma to phone me?"

I hung up, my eyes still starring at the object in my hand, the number I was instructed to translate to paper forgotten.

I was in her room, building a shoe rack in her closet when the phone rang. Being by the bed I had, of course, opened the top drawer, which lay beneath the phone, for a paper and pen for the phone message. What I found was not paper nor a pen.

With my free hand I turned the base and the six inch dildo began to vibrate in my hand.

That's when I started to break out laughing. A belly roar that I haven't had in months!

It was all so hysterical, my mothers mother had a dildo and a tube of lubricant in her bedside table!

She knitted sweaters for her family - scolded anyone that said 'hell', went to church each Sunday!

She was, till that very moment, the most uptight person that I know.

And she also owned a six inch dildo.

Grandmother lived in a condo minutes from my College and a twenty minute ride from home. I've never dropped in, unless beckoned, as I had been that fateful day. I had been volunteered by mother, to build some shelving for her mom, and after procrastinating and complaining, I finally went over to do the chore.

That was when I found 'it'.

The next time I went over, it was for a social visit.

"More tea James?" Grandma always had tea in a kettle cuddly that she knitted. Each year she knits a new one, along with bathroom, kitchen and dining room curtains, mats, towels... everything. She has done this militantly since I can remember - and all her grandchildren place bets on the next colour or pattern she was knitting.

Grandma poured enough to top my cup without a word from me. I had not been allowed a sip of coffee or tea until the day I turned eighteen. Now, she delivered it to me without my asking - and you want to know something, I hated fucking tea.

She sat back down and looked out the window for the sixth time since my visit, almost as if I had been interrupting something with my unplanned visit. "A lovely day don't you think?"

In her defence, I doubt she knew what to say to one of her grandchildren whom she rarely ever saw and knew little to nothing about.

For me, I was feeling awkward for another reason. I had come over to confront her about what I discovered in her bedroom last week. I'm not ever sure why, to tell you the truth, only that I had this intuition.

"How often do you use the vibrator grandma?" It came out softly spoken and just like that, without any warning.

The grandfather clock in the other room chimed loudly and the birds outside sang. But grandmother never said a word so I looked up from my cup of tea to see her bright red face looking at me with horror.

There it was, I knew that she was human after all. Not some strict automation that even my own mother feared to cross. Perhaps this was what scared my grandmother most of all - the discovery of her 'human' side.

Finally she seemed to gain back her resolve and she asked sternly, "What business is that of yours young man!" It wasn't a question.

I had the training of three slaves and the patience to go along with it - and I knew the looks a woman would give to attempt to hide her fear, disgust or humiliation... So I knew grandmothers strength, at that moment, was a mere facade.

"My guess you use it once or twice a week?" I glared right back at her - challenging. No matter how this visit worked out, it couldn't come back to bite me on the ass. Hell, no one in the family would even remember anything about this, if it got out, except that the old matron was using a sex toy!

"You sick little... pervert! Do you think I am some type of degenerate?"

"I think your a horny woman that needs a vibrator to get off." Actually, till the other day, she was nothing but a uptight old woman to me. One that I could barely stand being around.

She disengaged my glaze and looked down at her cup, which she held firmly with both hands. Her knuckles were white and the trembling in her hand threatened to spill her tea.

Finally, "I think you should leave James."

"Not until you answer my question?" I was the picture of calm patience - it had to irritate the old lady to no end.

"Do I need to call your mother young man?" Normally this type of statement would have put the fear of god into my youthful soul, but no longer. It had been used on me often as a child - it had no power now, I knew that she was human. Perhaps like Superman she had a weakness, one that appeared to be her sexuality. Of course she will never call my mother - grandma never wanted another soul alive to know of her weakness.

"Will you tell her how often you use the vibrator grandma?" I knew she couldn't let another human know about my discovery. I let the silence lay for a few lengthy seconds before continuing, "I promise not to tell another soul."

She simply starred at her tea and seemed to be trying to slow her breathing. Strange, since I could not see if she was hyperventilating or not. If anything she looked stunned, like a deer in the headlights of a fast approaching car.

I've never seen her look like this before - as if she was not in control. Which of course, if she realized it or not, was the truth - I was.

Then she whispered, "Twice a month... usually." It was an admission that the earth was not round, that we were not alone in the universe, that god was a woman.

The clock ticked with each swing of its balanced weight - the seconds turned slowly to minutes.

Time to lift her back up from that black pit of despair, "I do it once or twice a day grandma."

With a quick glance over the tops of her glasses, I saw her astonishment and maybe a little disgust.

"Men are different than women James." She was again talking to her cup and saucer.

I laughed lightly, "Evidently not!" I could see, even beneath the layers of makeup, her face pale.

The next visit was completely unannounced, and grandmother did not give me a warm look when she opened the door.

"Aren't you going to let me in grandma?" She stood aside reluctantly and closed the door after I entered. She was dressed in a flowered dress and looked like she was getting ready to go out, "Going somewhere grandma?"

I simply strode confidently into her living room.

"Yes, the church is getting the basement ready for the bake sale this weekend... !" The church was always getting the basement ready for something or another.

I sat down and motioned toward the couch across from me. Like a puppet she silently strode over to the couch and gently sat down.

"I don't have time for a visit right now James?"

I ignored her comment. "So, did you have the guts to tell mom about our little talk the other day?" I glared at her, though she wasn't looking back, as a challenge.

Grandmother never said a word, but again her face paled.

"Thought not. You don't want anyone to know that you have a little plastic friend you use to help you get off."

"James!" She looked angry at my bravado, glaring suddenly at me with a new spark. Or rather, the old spark.

"Well its true isn't it?" When her face hung back down, her eyes staring at the tops of her self-knit slippers, the same colour as the mats here in the living room, I let out a soft malicious laugh. "You know what grandma, you really are stuck in another time - girls like to masturbate as much as guys do."

Just a whisper, "Please leave here James." I pretended I never heard her.

"In fact, after our little talk the other day, I was so hot I went right home and jerked off - twice!"

Her eyebrows rose in surprise and I didn't miss the rapid glance down at my denim covered crotch.

Her gaze changed to bewilderment, grandmother had no clue why I jerked off after my last visit was my guess. "You don't realize how attractive you are do you grandma?"

I thought I saw a spark of pleasure in her eyes just before they again dropped down to stare at her feet.

And it was true, after all. She was, of course, not a thirty or forty year old woman any longer, but looked rather fine for woman of her maturity.

"In fact that's what I came over to find out - if you liked our little talk last time as much as I did?"

Nothing.

"Grandma? Did you get off since I was last here?"

Not a sound, but her lips moved, "No."

That surprised me, and I wondered if I was here, manipulating and humiliating my grandparent, wrongly. That intuition I had, that she was a woman from a different era, an era where the man was the boss and where her pleasure only made her only feel guilt - was I wrong?

"No?"

Again the minutes passed by with not a movement or a word.

"I'm starting to worry about you grandma, you are a beautiful sexy woman, I thought you would have used your little toy in the last few days?"

She ignored my obvious attempts at flattery when she boldly looked up into my eyes, "I threw it away."

That surprised me, "What? The vibrator."

"Its over James, it never existed. Now just leave my home and I will forgive you for these ungentlemanly questions."

At first I thought I had guessed wrong about my grandmother - that she was not the submissive woman beneath a strong tough shell after all. But I began to understand; the source of her humiliation and embarrassment was that vibrator - its use obvious. With it gone, her deep ingrained guilt at using such a thing for her natural urges, was but a memory. And grandmother was famous in our family for ignoring or forgetting things that she did not like.

My next visit was two weeks later - and her face looked stern with displeasure at another unexpected visit.

"What is it James?" Her free hand went to her hip in a firm resolved stance - effectively blocking the door.

I held it up and the meek and defenceless gaze returned and I strode past her into her home.

Grandma came into the room and sat down, in the same couch, me across from her as before. She didn't need to be instructed this time, much to my pleasure.

The vibrator, six inches and white, was still held in my hand before me. She was staring at it with something resembling defeat and disgust.

My other hand slipped into my coat and retrieved three attachments for the vibrator, rubber sleeves for a different feeling - the sales lady had said.

"Go call mom and tell her I'm fixing your door handle or something - and tell her I'm staying for supper."

Like a zombie grandmother stood up and I heard her do as I ordered in the den, from her side of the conversation with my mother.

When she returned I stood up and blocked her entrance to the living room - handing her the hard plastic cock. She took it in forefinger and thumb, like a thing diseased.

"Its new grandma, and clean." She gave me a look as if she had never seen a vibrator before but understood its purpose - and it appeared to disgust her.

"I want you to use it."

Her face snapped up, staring at me with astonishment and a little humiliation. I had expected anger - but I could see none.

"Right now - before supper." And yes, I did intend to spend supper here.

She just stood there.

I softened my gaze and voice, "I worry about you grandma - I think you are stuck in the morals from fifty years ago." Nothing. "Its OK, I'll read the paper in the living room - and I'll wait however long it takes." And finally, "I'm doing this because I love you grandma."

Her eyes blinked and she had to be thinking that this was all a crazy nightmare, but I kept the humour of this situation from my eyes. I would have time enough to laugh later, when I got home.

The minutes rolled past and I changed my voice and my attitude, roughly I ordered, "Go up to your room and use this between your legs right now or by god I'm going to spank you!" I put a hand on my leather belt about my waist for emphasis. My grandfather had been a strict disciplinarian, from the stories my mother and her two sisters told, and I had guessed it wasn't only toward his kids.

Grandmothers eyes widened in surprise, and I thought she would throw the vibrator at me and scream for an hour. If she did that, it would be the end of my little charade - at my attempt to discovering if she was submissive or not. It was the deal I had agreed with myself.

Instead, grandma, slowly turned and began to shuffle down the hallway toward her room. I stood there, my heart beating impossibly fast, as I watched her enter the door at the end of the hall and close it behind her.

My god, she was doing it!

I had been right, my guess at the submissive learning of a girl so many years ago and a wife to a strong demanding man, had been right.

Of course she was no longer a little girl, nor was she a married woman - but the decades long lessons had ingrained into her soul.

I sat down in the living room holding the paper before me as if reading, though I never saw a written word, and waited.

An hour passed before the door to her room opened and she shuffled down the hall, quickly turned and went into the kitchen where I heard her preparing for my supper.

I left her alone till she shuffled back to her room, leaving a steaming plate of leftover tuna casserole on the dining room table. I ate alone.

Shouldn't a grandson feel guilt at forcing his mothers mother to humiliate herself like this? Of course.

But I didn't.

A week later, I called her from school, a pay phone. "... something besides casserole grandma?" Nothing but her silence. "I'll be there in ninety minutes, go to your room and do it again grandma." I was watching about me, making sure no one could hear my commanding words to my own grandparent.

I did not wait for her acceptance before I hung up.

Three more times that month I went over for supper, either her going to her room before I got there or afterwards. Each time she would make me supper after, leaving it on the table, and disappearing to her room.

This time was different, when she shuffled with defeat, by her walk and that heavy invisible burden on her shoulders, into the kitchen she found me there by the sink, with only my boxer shorts on. I turned to see her opened mouthed gaze, her surprise. She wore an ancient ugly pink bathrobe and knit slippers.

Grandma had just completed my instruction; her face looking drawn and tired as I would expect.

I pretended surprise at her silent look, "What did you expect - I have needs too grandma."

I set the empty cup down on the counter, the ruse that I was getting water no longer needed.

"What... where are your clothes?"

"In the living room." I pretended to misunderstand her gaze, "Don't worry, I used a tissue so there was no mess."

"But... ?" She didn't know what to say and I fought hard not to break out laughing at this comical situation.

"Can you eat with me tonight grandma?" She nodded and quickly turned her eyes away from my near-naked body, and shuffled over to the fridge to retrieve the leftovers to roast pork.

Grandma frequently stole glances at my teenage body for the rest of my visit.

To see me at her church was almost too much for the widow.

Grandma grasped my elbow roughly, smiled over her shoulder at the other white and gray haired ladies, and pushed me to a table in the far corner of the church basement.

"Get out of here right now James."

"You didn't say 'please'?"

Her eyes were roared with anger... and a hint of fear.

With a forced calmness, "Please James, go home."

"What if I wanted to go to your home and wait for you?"

Suddenly the fire was out and she hung her head in shame or humiliation, "If you wish - just please please leave here?" This time there was the proper amount of submission in her voice to excite me.

I looked over at the three elder ladies, attempting to ignore my grandmother and I - but they were not doing a very good job of it. From our distance, they sounded like a gaggle of geese as they chatted and frequently looked toward us. My grandma knew it too - we were the subject of intense scrutiny. I smiled at the ladies and waved - my grandmother turned bright red.

"Will you agree to do something for me?" I looked back at her to see fear at agreeing to an unknown request from her grandson who ordered her to retreat and masturbate at his discretion.

The ladies were edging closer as they set booklets on the folding tables situated about the room. Grandmother heard and knew it as well - "Yes, anything, just leave James?" There was a little amount of pleading in her voice. It as only a matter of time before the old busy-bodies interrupted us.

"Are you Betty's grandson?" It was asked half ways across the long room, but the click of the heels on the tiles loud. I saw the fear in my grandmothers eyes.

I looked quickly down at my grandma, her eyes waiting for me to agree to leave, pleading with me. "Come home by six o'clock tonight." She nodded quickly, almost thankfully. Then I smiled and swung the final blow, "I want to watch you tonight." She almost collapsed and probably would have if not for the three ladies and the younger one who had called to me from across the room finally reached us.

My hand shook all three ladies paws in turn, as they fussed and chatted up with me. My grandmother silent and white as a sheet behind the small crowd, she stared at me with a unreadable face.

When it was time to go, I leaned in and gave my grandmother a quick hug - and whispered, "Don't be late grandmother dearest."

She came home to find all the rooms dark - all except her bedroom, where a single candle was lit.

That was where she found me, "James... ?" I was seated in a hard back chair at the foot of her double bed. When she started to talk, to tell me that she could not do this, that it was wrong and immoral, maybe even evil - when I put a single finger over my lips to shush her.

We both looked down to my lap at the same time. Across my lap lay my belt, bent in half and held in one hand. The threat obvious.

Finally, grandmother looked about her room as if she never saw it before, swallowing loudly when she saw the vibrator I gave her and her tube of lubricant sitting on her bed. I saw the tremors that her body underwent starting then as well - this was pushing her boundaries probably further than she had ever imagined.

When she stood there silent for nearly a minute, I thought I would have to get tough with her - remind her who had the power in our relationship. Then she simply turned and shuffled with a defeated walk to her private bathroom.

I sat silently, patiently, as the minutes passed. Ten minutes and she finally emerged. I'm not sure what I expected, but her neck to ankle flannel nightie was not it. I couldn't see a thing but her hands, feet and head.

Grandma crawled up into her bed, pushing the toy out of her way, and lay down upon it almost at attention. I saw that her eyes were half open, and staring down her body to me... at me.

She had piled her hair into a bun on the top of her head, and had removed most of her makeup in her earlier retreat to the bathroom - so that in her white nightly in the pale light she looked younger, a different woman.

Then still looked at me, she lifted the hem of her gown slowly to mid thigh, showing more bare leg of hers than I've ever seen, before stopping.

She reached over and found the vibrator, strangely silent and non-combative in my request, then squirted a large amount of lube upon the length and about the head.

Grandma turned back to me, and spread her ankles a meter apart and with the dim light I could not see anything but darkness up her gown, believe me I tried. Then she lifted one knee and shoved her ankle into her soft bed. Slowly she slipped her hand, and the prepared vibrator, under her gown and between her white soft thighs.

I couldn't see where it went but found my cock hardening painfully in my jeans.

Still watching me, grandmother wiggled her hips, adjusted her legs and then reached down with her free hand and fumbled for a brief second before I heard the buzz of the sex toy. The unused hand came out from the darkness between her legs and grasped her raised thigh, near the knee.

Her eyes watching me, looking into mine, staring down at my rapidly moving chest and maybe lower... then I heard it. The obvious sound of the little electronic motor as it was stuffed repeatedly in the sheath of a woman's folds. Grandmothers face never registered what I knew to be going on between her legs. The sound of the buzzing rising and falling in volume as it moved slowly in and out of her vagina.

My god, how easy this all was - forcing her to submit herself to my wish like this! I sat and watched, listened, to her masturbate. My fucking grandmother for gods sake!

She had to be a natural submissive, she just had to be! Grandpa must have beat her black and blue, before climbing upon her - she submitted easier than I would have ever guessed.

Finally she closed her eyes and swallowed loudly for a brief second before again opening them and staring at me firmly.

I could jump her right then, replace that fake cock with my hard shaft! Or at the very least, I should pull out my dick and give it some relief, it was down right hurting in my jeans!

I couldn't of course, I promised myself to be a spectator this time - to be content with getting this far. Afterwards, another step past that invisible line could be crossed - but for right now, let her do this thing I commanded, show her my dominance and self-control... and yes, even my pleasure at this scene. A woman, a slave, need to learn to trust her master.

Her eyes were starting to close more rapidly, the large gasps silent but obvious, the swallows louder. Her hand upon her thigh was clawing at her white skin, the nails biting into flesh. Grandmothers hips were moving in small circles, almost impossible to see in this light, in time to the sexy sound of the movement of that plastic cock.

And something new, something wondrous. The scent of her... her sex, it was filling the room and my head with its earthy aroma. I loved it. Then the sound, of a woman excited, getting louder as the seconds passed - sloppy bawdy echos from between her thighs.

I was all so incredible.

When I looked back to her face, she was again staring at me, sad and pleading silently. She whispered nearly beneath the sound of her sex and the moving electric cock, "I want to stop?"

I didn't understand - stop this show, this command? No, impossible, not now!

My head firmly nodded negatively.

A tear rolled down one of her checks and she whispered again, "Please... ? I always stop now. I can't go on!"

What?

"I have to stop now... please?"

The scene was impossible, it couldn't be stopped and of course immediately grunted, "No!"

Tears were rolling down her cheeks like a river even as her hips started to press upwards, the sounds louder, and the smell stronger. I knew the inevitable was approaching and I painfully clenched the arms of my chair and leaned forwards.

Grandmother was no longer begging to stop, pleading with me to end this - why she started too, I have no clue. It hadn't been the request of a woman in heat, it wasn't brought on by her passion.

Then it happened and grandmother lifted her ass and hips from the bed then held herself there in an arch. She squealed out in pleasure and froze in place in that obtuse position. Time stopped as she hung there, even her breathing had stopped. Seconds later, she fell back to her bed and gasped out for breath.

Even in the dim light I could see her exhaustion, her sadness as she pulled a shiny hand from beneath her thighs and rolled over into a fetal position on her hip. From where I sat, with her knees up nearly to her chest, I could see something poking out from directly between her round ass and thighs, pressing her flannel nightie outwards obscenely. The vibrator had been left in its place, a large round damp circle staining the white flannel gray.

I stood up upon trembling legs, my cock forcing me to stoop over comically, and made my way to the edge of my grandmothers bed. Bending silently over, I sat looking down at her face, the tears streaming down freely now, her humiliation complete. I leaned in and kissed the top of her head before standing and silently leaving.

When my grandmothers voice came across the phone I could not have been more surprised. "Hi James."

"Grandma?"

"Uh... did you want me to fix you supper sometime this week?" I could hear the quiver in her voice, the awkwardness of this situation - having to call her grandson to come to her home.

"I would like that grandma."

A lengthy pause, "I thought maybe... after last time... you didn't want to... ?" I haven't called or dropped in since my voyeur show two weeks ago, somehow she had interpreted this to mean something. What exactly, I wasn't sure. Did she believe I felt disgust at what I had witnessed?

My mom and dad looked up from supper and mom made a motion, as if asking if her mother wanted to talk with her.

"Mom wants to talk with you grandma. I'll come over for supper tomorrow night." I looked at mom across the room and with a smile and nod she confirmed my statement. What else could she do, she was very pleased that some of the burden of spending time with the old broad was off her shoulders.

"I would like that James." Did she rely upon my visits for her pleasure now - was she already submissive to me to this extent?

"I'd like that too grandma. I have something I want to give you too."

A long pause, "OK." She didn't sound too sure at my offer.

Mom was standing next to me with her hand out, "Here's mom... see you tomorrow grandma!"

Tea again!

When both cups were filled, the two of us sitting in her living room again, as if the last weeks had not happened and it was only a rebellious teenager reluctantly visiting his ageing grandmother.

"I wanted to tell you something about your last visit darling."