My Single Greatest Challenge free porn video

Copyright© 2001-2003

There once was a gaucho named Bruno,
Who said, "About sex, well, I do know,
Sheep are just fine,
Chickens, divine,
But iguanas are Numero Uno."

It was a simple question but I felt my heart pounding in my chest and froze with a stupid open-mouthed gaze.

Mom looked from grandmother, her mom, to me and back again.

My frozen stupidity only lasted a mere couple of seconds but it was long enough for me to realize that mom knew something was wrong. For two people to overreact to the simple question of, "What are you two up too?"

I looked over to my grandmother and saw that her face was flush white beneath her makeup, her eyes looking guiltily down toward her feet. The submissive response that I've come to know and enjoy.

Mom had unexpectedly come over to her mothers place, to pick me up for a family supper tonight. No big deal right?

Well, mom was no dummy - she saw the strange reaction we gave her at her seemingly polite question - though she would never imagine her son and her mother were fucking up a storm would she?

In fact, I was staying here at my grandmothers house more nights than staying at home. My excuse was that I was getting busier at college and grandmother lived a few minutes walk from the campus. No one would suspect a senior citizen to be living in complete submission of her grandson - would they?

I rather enjoyed the last couple of months, a slave available at my merest whim. And I used her expeditiously - and she loved every second of it.

You see, grandma had the door to her sexuality opened by me - pleasure and ecstasy were an unknown till I forced her to enjoy what I told her too. She loved me, of course, but more than a grandparent, she loved to pleasure me - because that was the path to her own pleasure. Nether of us, any longer, cared that it was immoral, unethical and illegal.

Never before had our little relationship come so close to being public as in that few seconds when mom saw our reaction to her question.

"Honey - why haven't you been dating anyone lately?"

It was weeks after mom picking me up at grandma's, but I was instantly suspicious of her question. "Ah mom! It just wouldn't be the same since Georgia left." Which was true - Georgia was my third slave and I had been crazy in love with her.

She seemed to drop it, thankfully. "Are you going to be home this Saturday?"

I simply nodded 'no'.

Grandma knelt at my feet in the living room, she wore a towel wrapped just below her armpits and had her head upon my naked thigh. Minutes before we had coupled like animals and then showered together and I knew my grandparent had enjoyed herself immensely, as she usually does.

I was absentmindedly stroking her hair and flipping through the channels on the television when my slave gently commented, "Gail came over today."

I forced myself to simply relax and continue flipping through the channels, but my heart was racing and my mind raging. Mom must have visited while I was at school. "Oh?"

"I think she suspects something."

The blood must have drained from my face and I realized that I sat frozen in that position. Now, I had never seriously thought about the consequences of someone finding out about my relationship with my grandmother, but it was starting to get serious. "Why do you think that?"

Grandma lifted her head from my lap and shrugged, "She is just acting strange. She commented how good I looked today and asked me if I found a boyfriend."

It was true, fucking agreed with grandma - she looked ten years younger in my opinion. The strangest thing, and what grandma never voiced, was that her daughter, my mom, never normally enquired into her mothers love life.

Finally she asked, "Do you think we should slow down a little darling?"

After a lengthy sigh, "Do you want to grandma?"

Immediately, "No."

"Neither do I." My cock twitched beneath my own towel, and I noticed that grandma had quickly looked down at the jerking movement.

Then she continued, "I found what I have with you so late in my life that I'll do anything not to jeopardize that." I wondered what 'anything' meant? "Please don't leave me James?" 'Leave' her meant stop fucking her.

A tear was sliding down one cheek and lifted my hand to cup the side of her face softly, "I have no plans on 'leaving you' my little girl." 'Little girl' was this verbal game we played.

She pressed the side of her face firmly into my hand and smiled up at me. "I want you James." Meaning she wanted to fuck me.

I wanted her too.

"Come here grandma." She quickly shed her towel and crawled up upon my lap - fishing beneath my own wrap, she found me hard and ready.

Her sex, as I have come to expect, was hot wet and ready as she sunk down upon me.

I didn't mean too but I started to think about my mom finding out about grandma and me. What I mean is that I became obsessed on the topic of mom suspecting her son and his grandmother having intercourse. I started to go to lengths to deceive her on my whereabouts and actions. I spent time watching her while trying not to be watched. I wanted to figure out what she knew and what she would do with any knowledge if she knew about it.

It wasn't to great effect - I learnt next to nothing.

But something else happened, actually an idea.

You see, mentally I have been boasting to myself about how great a challenge it was to get my grandmother to be my slave. It was the greatest huddle a man could ever do, I imagined. Yet, there was something, or rather someone, even a greater challenge was there not?

Mother was in her early forties and attractive, in her middle-aged sort of way. I've never, and I mean ever, looked upon her with the gaze that I've only started - as a sexual woman, a possible slave.

Now that, without a doubt, would be my single greatest challenge - would it not?

I already have a slave, of course. One that I was partial too actually - fucking grandma was fun and I did not want it to end. Seducing my own parent, while it seemed impossible, had to be worth the risk. If only for the immoral pleasure of mounting your own mother.

Where grandma had a tiny thin frame, mom had a voluptuous tiny frame. Grandma had average sized breasts, mom had these big mammeries that seemed obnoxious on such a small woman. They actually made her look fat, but I had known since a child, they it was all breasts instead of fat. Grandma had a rather large round ass, mother had a round better proportioned bottom. Grandma had a nest of wrinkles about her eyes and lips, mom only had small barely-noticeable lines.

They were the same but different, one aged the other ancient.

Suddenly, after weeks of watching her and contemplating my options toward getting 'caught', I suddenly found myself desiring my mother.

Could mom be a natural submissive as her mother was?

They certainly had a different background. Grandma grew up in a strict poor household, where anything sexual was taboo and severely extinguished. Mom also grew up in a strict household, but closer to middle-classed, and from what I gathered mom was kind of a tramp before she met dad, rebelling in the values her parents attempted to teach her.

Perhaps this was the one time to test another theory of mine out, if being submissive lay in the genes. Could mother be as submissive to her sexuality, to me, as grandmother is?

Mom picked me up at grandmas after work, as asked. I jumped in the car and quickly leaned over to kiss her. In the process my hand grasped the upper region of her slack-covered thigh and pressed my lips against her cheek, near her mouth.

I sat back, just as quickly, and buckled myself in and pretended to be looking away.

Mother sat frozen for several seconds before putting her BMW into drive to speed away.

Out the corner of my eye I watched her.

She had to know; could she not smell it? Feel it upon her skin? Even see the damp patch on her wool slacks?

You see, I had just come from between my grandmothers legs. Timing it cautiously, I orally pleasured my grandparent to a generous orgasm - meaning I had leisurely licked and fingered her hungry cunt and ass. When I had placed my hand upon moms thigh, it was still dripping with grandma's juices. When my lips pressed upon mom's cheek, near her lips and just below her nose, I left a damp patch of her own mothers sexual spend.

So out of it, after her orgasm, that grandma had no idea I had ran out of her own dripping with her juices - not sure if she would have cared regardless.

Mom, on the other hand, was looking at me frequently, at my face and at my hands. She was sniffing frequently and I saw her reach up to wipe the juice from her cheek before sniffing her fingers deeply.

Her eye widened impossibly and I knew that my own mother now knew of my incestuous relationship with my grandmother.

I never had a plan, so little did I know about my own mothers sexuality, but I went on instinct and my own desire to win this challenge.

Mom received my blatant non-verbal message about her mother and me rather well, considering the subject manner. I mean we didn't get into an accident on the way home or anything.

Sometime that very evening she did come into my room looking like the wrath of god.

"James what the hell is going on with you and your grandmother?"

Its almost comical if you watch someone who is trying to be quiet while acting furious and non-shouting. Mom looked like she was going to pop a blood vassal.

"What do you mean mom?"

I could see that she wanted to slam the door but dare not, it closed silently behind her. "Its wrong James and its disgusting! How could you?"

"Your talking about grandma and me having sex aren't you?" I was purposely being obtuse, throwing this into my mothers face. She was libel to figure it out eventually regardless of my callus actions.

Hearing me say those words though, had an instant affect upon my mother, and she stalled in her lashing out. Finally, after a full minute to calm herself, she continued, "When did it start James?"

"Just after I fixed that shelf in her closet."

Mom looked disgusted, "The one I sent you to fix?" More accurately, the one she nagged me to fix. Was she already blaming herself because this started when I was nagged to do some handiwork around grandmothers house.

"Yes."

"It has to stop, now, James." She looked firm but calmer - like this was the the real purpose the middle of the night visit, and mom was thankful to finally get it out.

"No."

That surprised her - that and how calmly I spoke it. She shook her head and expanded upon her order, "You must James! Its wrong. Its illegal. Its... !"

"Mom?"

She stopped in her logical reasoning why a grandson does not have sex with his grandparent, and nodded for me to ask my question. The look of extreme displeasure and forced patience written upon her brow.

"I don't want you to say anything to grandma about what you know." It was calmly spoken but obviously not a request - but an order.

I've never talked to my mom that way before and we both knew it.

Her mouth hung open for several seconds before she asked, "My god, you can't be serious?"

"I am."

Her arms crossed over her chest, "Tell me why I shouldn't ask my own mother why she is molesting my son?"

I couldn't help it, her choice of words seemed so inappropriate to my relationship with grandma, that I broke out laughing. I quickly regained control of my faculties, though I had angered mother even more by me outburst. "Because if you do I'll have to spank you." My heart actually fluttered when I said those words - and though I had not intended on saying it, I had no regrets once the words were out.

It was, after all, my favourite form of punishment for one of my slaves.

My room suddenly seemed dark and cool, the silence now thicker than the air. So much so, that neither of us could breath calmly.

"First thing tomorrow morning I'm going to go over to moms house and confront her James. And you can do nothing about it."

This was it, the moment in our lives when we become adults. Most certainly this could not be the way that the majority handle it.

My heart, pounding fast, allowed me to adjust from a compliant and amused man to an angry, defencive one.

The thought that mother could hurt her mom, my grandmother, so lightly made me furious. With barely contained rage I stood up from my bed.

Mom didn't look to sure of herself now, and I saw her peek behind her at the closed door, probably sorry for closing it in retrospect. She had to see my anger, feel the raw rage in my cluttered room almost electrify the hairs upon our heads.

My hand reached out quickly and grasped the front of her robe, mom opened her mouth in fear even as I yanked her off her feet toward me.

I twisted and she landed among my messy bed, face down. A new energy lay in the air, mothers fear of her son.

I jumped upon her, my knees straddling her waist so that I knelt upon the bed, my hands twisting her head so that her face was exposed to me. Just as her mouth opened, to scream was my guess, I clamped my strong hand over it.

At that second I came to my senses and realized what I had done; knew of the enormous shift to our lives by the actions I had went through. There was only one option now, the only thing I could do in such a situation.

Calmer now, I gently held my mother to my messy bed while I retrieved one of my socks. Quickly, I removed my hand and then shoved the soiled white cotton sock into her mouth.

I expected her to be flailing about, but mother just lay still upon my bed, watching me over her shoulder with something like terror.

Sitting upon the edge of my bed, I then roughly dragged my tiny framed mom over my lap. She didn't resist the whole time, strangely enough. Then tore at her robe and satin nightgown up to her waist. Only then did she attempted to roll away from me - a quick twist of her arm behind her back stilled any remaining rebellion.

Mothers white ass seemed to shine in my dark room and I realized that it wiggled delightfully as mother was undergoing violent shakes ever few seconds.

The path was set and there was no turning away.

My hand came down with a deafening smack, her ass flattened and reverberated wildly. Mother suddenly straightened out her back and screamed into my sock, already, visible in this dim light, a large red hand-print was appearing upon her skin.

Again my hand came down and again. She was jerking about my lap, not so much to get away but as a response to the pain stimuli her bottom was undergoing.

I have no clue how many times I struck my own parent - but when my arm was too sore to lift and my hand throbbing in time to the red welts upon moms ass, I stopped.

I simply lowered my knees and mother rolled off my lap to the carpeted floor before me.

That next moment, several things happened. First I realized I had one huge aching hard cock - mother had to have felt it against her hip, there would be no mistaking the aggressive bulge in my cotton warm up pants. Second I looked down toward my boner and saw a dark spot upon the gray cotton pants, directly where mothers sex had hovered over. Finally, mother curled up into a ball before me and sobbed silently. Her eyes, though, watched me with something between awe and terror. I reached over and pulled the sock from her mouth and her gown over her still exposed ass.

My anger was gone - but I felt no regret for what I did. "Grandma is happy, maybe for the first time in her life... and you want to destroy that?" Mom's only answer was to sob loudly - staring at me with a strange hard look.

"Get out mom."

She began to claw her way to the door, crying all the way.

Nothing happened - nothing. Mom certainly did not talk with her mother about me. In fact, she never said anything at all to me about her midnight intrusion or the spanking she received. I did notice her wince a few times when she moved or sat that week, but no one else seemed too.

A week passed when I came up to mom in the kitchen, "Mom, can you drive me to grandma's?"

She looked wearily toward me, knowing why I was going, but nodded her reluctant acceptance anyway. Outside grandmothers home, I unbuckled my seat-belt and just as I was opening the passenger side door I instructed a humiliating demand, "Come back in ninety minutes mom - I'll be finished with grandma then."

When I exited grandmothers home, mother was sitting in the running car, waiting as instructed. I slipped into the passenger seat and leaned over to kiss mom.

She turned her cheek away, guessing where my lips had recently been, so that I moistened a point just below her ear with my cunt-wet lips.

"Lets go mom. What's for supper - grandma really worked up an appetite in me?"

Mother simply looked horrified at me.

That was the way it went the next month, mother dropping me off or picking me up at my slave's residence.

At some point soon after that first ride, I would begin to give mother some of the details of what I had done to her mom. Fuck, suck, lick... mother heard me describe my actions with her mom, in great detail. At first she appeared horrified and disgusted, but by the end of the month she appeared to ignore me.

She asked me to stop of course, but I only laughed and told her, "I would have thought you would want to know what makes grandma happy mom?" That shut her up.

Was my mom a submissive like grandma?

Other than driving me to and from the slave's home, there was not much evidence to go. I certainly had not pushed the boundaries, as I had with grandma those first few weeks. Oh certainly I pushed the limits of our prior relationship to new heights, but it was probably because of mothers silence rather than any submissive quality I may or may not have sensed.

I had to push her further, faster.

So, the next time mom and I drove home from grandma's, with me reliving every sordid detail to mom, I slipped my hand over to her lap. Mom almost got in an accident as I slipped it beneath her long woollen skirt, then tried to tear at my hand even as it found and cupped the crotch of her cotton panties and her treasure beneath.

"Well, well. Looks like you enjoy hearing about grandma and me!" Mom was indeed wet and warm between her legs - the cotton noticeably soaked.

"Please James... please!"

She drove up into our garage and put the car into park, my hand still where I had initially placed it. Mom turned toward me in her seat, but said nothing - she looked rather sever though.

"Did you know that grandma loved to masturbate - used a vibrator too?"

After all the other details she had heard, mother never visually responded to this piece of information but I thought I felt her sex twitch beneath my hand.

"Do you masturbate often mom?"

"I'm getting out of this car right this minute James." She didn't move and neither did my hand.

"Grandma's vibrator was white, what colour is yours mom?"

"This isn't right James and it has to stop."

I pulled my hand from beneath her skirt, "Your right mom." I brought my hand to my face and laughed silently as mom watched me smell and then taste her juices from my digits.

"Hum... not as strong as grandma's."

"God your disgusting... !" Mom slammed the car after she got out.

That was the start of me openly fondling mother outside her panties or pants - rubbing gently as I told her what I wanted to do with her mother or what I had done. She never stopped me but she always acted disgusted at my actions - her sex, though, lubricated quickly and warmed my hand delightfully.

The chauffeured rides to grandmothers never stopped - my mother always seemed available for that chore.

Grandmother noticed as well - and peering out of her closed curtains at the running car before her home, she whispered as if her daughter could hear her, "Do you think she knows?"

I was seated, naked, upon the couch - attempting to catch my breath from the rather delightful sexual escapade we had just completed. "Yea, she knows."

Grandma turned her face toward me, her mouth open in horror - the blood already drained from the skin of her cheeks. Her naked exposed thin body seemed to shrink before me.

The clock in the corner chimed and I realized with a malicious grin that mother had been waiting for her son for nearly a half hour.

My grandmother brought her hands up, rather ridicules knowing how intimately I knew every inch of her person, to cover her breasts.

Even tired as I was I sat up and growled, "What did you expect? Mom only wants you to be happy." Not really true - but I felt no guilt at this little lie.

Stammering, "Really?"

I nodded. "Hell, I think she actually enjoys the thought of you and I... together!"

Grandma's eyes got larger before she got up the nerve to ask, "Does anyone else know?"

"Nope."

That seemed to revive her a little, and her breasts were again exposed. Grandma peeked out the front window yet again, "Your mother was always the wild one of my kids." This was spoken mostly to herself rather than to me.

"We both love you grandma." She turned her head in surprise at my statement - the word 'love' used so rarely between us.

"I love you too." She used the word frequently between us, but this time her statement seemed to bring tears of joy to her soft eyes.

I stood up, my strength rapidly returning, and looked around for my hastily discarded clothing. "Good - from know on I'll tell mom she can wait for me here rather than in the car."

Grandmothers eyes shot up in surprise, but she continued to look out the window between a crack in the drawn curtains.

Mom was staring at a magazine when I descended the stairs and came into the living room. She was attempting to ignore me.

I was only wearing my boxer shorts and carrying the remainder of my clothing when I came before her and pulled the magazine from her her hands. She looked up at me in surprise, not from my appearance but by my actions, and I turned the magazine over and pushed it back into her hand.

Mother turned red, the magazine had been upside down.

As I sat across from mom and pulled on my socks, grandmother finally followed me into the living room. She was wearing a new silk bathrobe that I had purchased as a gift for her some weeks before. The robe, which stopped just above her knees, allowed her white stocking-clad legs to be revealed.

My mom could not take her eyes from her mother as the elder matron came into the room. "Can I get either of you something to drink before you go?"

I was proud of grandma, she was trying very hard to be casual about our little circle of knowledge. Its only been a week since learning that our relationship was known to her daughter - and in that week I had dominated her into accepting the inevitable. The clothes she was wearing now was what I had ordered her to wear minutes before.

"No thanks grandma. Mom?"

Mother was open mouth looking at her parent in such a foreign garb - and do you know why, the older woman looked good.

Finally mom nodded negatively, still staring.

Grandma was slowly turning red from the scrutiny of her daughter before her lover. It was obvious where we had just come from - what we had been doing. Even if mother had not been waiting almost twenty minutes and had to have heard her mother squeal in orgasm minutes before - the situation was obvious.

Dressed I stood and cleared my throat to get mom's attention; "OK, lets go mom." Grandma looked thankful that I was taking this awkward situation out of her home. She would do what I ordered but she could not silence decades of morality that went against nearly anything I asked of her.

Mom went out the front door with me following, just inside the house I turned and pulled grandmother to me suddenly. We kissed, my tongue spearing into her mouth aggressively. I slipped my hand up between the silk folds of her robe, pulling it wide apart, and fondled her soft exposed average-sized breasts. Grandmother balked and froze at my forwardness in such a public forum, her own daughter feet away, but submissively did what I wished.

When I finally disengaged and turned I found mom standing a few feet behind me with mouth open and eyes wide. Both ladies had red embarrassed faces as we parted company.

Grandma pulled closed her robe even as I was climbing into mom's BMW, her daughter not able to stop staring at her.

Minutes later, after turning away from grandmothers street, I softly ordered, "Spread your legs mom."

Turning to me slowly we shared a look before mother spread her knees as far as the drivers seat would allow.

My hand slipped beneath her skirt, across her hot thigh and directly over the crotch of her panties.

Mother never said a word and simply kept driving.

Cupping her sex, which was wet enough to soak the cotton brief, I started to press into the top of the groove with the tips of two fingers - rotating and grinding them as I knew grandmother loved.

In response, mother hissed and grasped but did not attempt to close her legs.

The the remainder of our drive I spoke softly, lewdly in her ear as I fondled her clitoris through her panties. "Like listening to your mom and son fuck don't you mom?" She never spoke a word. "Gets you hot just listening to grandma scream in passion doesn't it?"

Mother barely got the car into our garage without hitting both the edge of the wide door or putting it through the far wall. Yet as soon as the BMW was out of drive she dropped her head back onto the neck rest and allowed the orgasm to come.

Mother gasped, so much like her mother does, as the orgasm washed through her body.

I slipped out of the car, knowing that I would not be missed for some minutes - so out of reality had I left my own parent.

Mom knew I was boning grandma of course but she only started to realize that it was something else, something more sinister about the relationship. It was not a case of Spring - Winter passion, two people, regardless of age, enjoying the passions of the other.

No, she started to realize that I was the dominant with grandmother. With her too, she knew.

I openly fondled my grandparent before my mother now and grandma had found a deviant joy in allowing her daughter to see her happiness. I ordered my grandparent to wear some of the skimpiest clothing - sheer lace often - parading her before mom's wide eyes. I would ask grandma the lewdest questions regarding our intimacy and get a lewd answer back - all within mothers range of hearing.

Between mother and I, I had withdrawn actually. After giving her the orgasm in the car I rarely did more than pat her round sexy ass.

This forced mother to show her hand, to ask me if she could drive me to my slave's home, asking me if the clothing she wore would be acceptable and if it was anything but a skirt it never was. I would succumb to some requests, letting her drive me to and from grandma's, I would critique her clothing till she wore what I wished. But it never went past that.

Mother wanted more but I never delivered - was it her submissive side that drove her passions or only a middle-aged horny woman?

All this time Grandma was a happy woman - getting more and better cock than any other period in her life. She worshipped me, bowed to my phallus altar. Nothing I told her to do was denied.

Then, kneeling between her raised legs - my cock hard and immersed in her sex, I told her, "I'm going to add mom to our fun grandma."

I felt her body almost chill - her sex seemed to freeze about my cock and her passion died in seconds. Our eyes met and I saw hers tear up.

"Its that or our secret may get out."

She just stared at me.

Downstairs mother waited, frustrated but silent. I had found something within her that she never knew existed - what was mirrored in her parent. Grandma had a desperate desire within her - almost as if she wanted to get as much of my cock for her pleasure before time caught up with her. Mother on the other hand, was in that early stage of my domination - and I did not know what was laying within her soul and unsure how right and wrong could possibly be accountable to her forbidden passions.

I felt the need to reason with my slave, "You told me many times that you would do anything to keep what we have?"

A tear rolled down her cheek.

"You have enjoyed these last couple of weeks, with mom seeing how much of a slut you are?" Grandma, even after all this time, still hated to be called a 'slut'.

Finally, she speaks, "That was different!"

"How is that different?"

She just swallowed loudly and turned her head away from me - suddenly ashamed I would guess.