Your wife Jane finds out that you are a masochist and wants to face the day in the evening. She is waiting for you at home until you come back and bring up this subject.

Why wouldn't they be? You remember how much fun we had with Grandpa Bob when he was alive...and now it's time to honor his memory by continuing the family tradition. I told them you were a masochist, and they couldn't wait to help me break you in. Now let's see what kind of day you've had to make this all worthwhile for us. She hands you a glass of wine, motioning for you to sit down on the couch between her and your mother

Thank you, dear. We just wanted to make you feel nice and comfortable. And we know how much you like watching old people have sex...why should that change now? Your mother had some ideas for ways we can all have fun tonight...and she's very creative when it comes to humiliation and pain. Now, tell us about your day at work. Make sure you don't leave anything out!

She nudges you playfully with her knee as she takes a sip of wine, her breast pushing against your arm

How dare you! You little...oh, but she is old and fat, just how you like it, isn't it? Hmm...I guess that won't work then. We'll have to find something else for tonight. But first, let's start with a little game I like to call "Truth or Dare." You know the rules. If you choose truth, you must answer honestly, and if you choose dare...well, we all know how much fun that can be. Your mother has come up with some wonderful dares for you tonight. So, which do you prefer? Truth or dare?

"All right, then," says Jane's mother, smirking. "I dare you to go out into the living room and find something small and shiny. Bring it back here for me." She pauses, considering. "Oh, and make sure you use your tongue!"

Ahh...that's very good! She takes the dime from your tongue and pops it into her mouth, sucking on it suggestively before pulling out a tiny gold ring she always wears Here, why don't you wear this for me tonight? It'll be like we're...well, never mind. Just put it on. Now, since your dare was so adorable, I won't punish you...but don't think that means you can slack off with the truth or dares next time!

She slips the ring onto your finger and pats your hand before taking another sip of wine, her nipples visible through her silk blouse as she does so

Hmph...old people don't need dares to have fun. But we'll humor you anyway. Granny, why don't you show our dear slave here how much pain he likes? Show him that his day would be nothing compared to what we can do with you in charge! Make sure he gets a good look at everything...

You sit there, your heart racing as you watch Granny undress before you. Her white hair flows down her back like a waterfall of silver, and she's not nearly as fat or old as you thought she'd be at this point in life. In fact, her body is surprisingly toned from all the workouts she does with Jane.

She grabs your hands and pins them behind your back, pressing your face into her ample chest. Her breath comes hot and fast against your ear as she whispers dark promises of pain and humiliation. And then she starts to grind against you, her soft but strong thighs rubbing against your aching cock.

You're only vaguely aware that Jane and your mother are watching this little display with smirks on their faces, as if they knew exactly what was going to happen all along. You try to struggle, but Granny is far stronger than she looks, and the more you fight, the harder she presses down on you.

With a sudden thrust of her hips, she pushes one hand between your body and hers, trapping it against her wet folds. The other hand grasps at your shoulder, forcing you deeper into her breasts. As you feel yourself start to lose control, she leans down and whispers in your ear: "You like that? You want more?"

*Jane moans appreciatively as you shower Granny with attention. She leans over to whisper into your ear, "That's it, my love...give her what she needs." Her hand reaches down and slips between your spread legs, finding your already-hard cock and beginning to stroke it in time with your tongue's movements on Granny's wet folds.

As you work, you become acutely aware of the power dynamic at play here...the fact that not only are you servicing a much older woman, but also that Jane and your mother are watching every move you make with amusement and delight. The pleasure is almost too much to bear, and with a final thrust of her hips against you, Granny lets out a long, shuddering moan and comes hard around your fingers, pressing her body more firmly against yours as she quiets down into blissful exhaustion.

Your mother leans over and whispers in your ear: "That was amazing, sweetheart...but don't think you can just sit back now. I have plans for you tonight, and they don't involve rest."*

Jane's mother grins maliciously at you over the rim of her wine glass. "Oh, all right then...I choose truth." She pauses for dramatic effect before continuing. "You know how much your father loved to watch us have sex? Well, I bet he'd love to see it now...with you as part of the audience!" Her eyes gleam wickedly in the low light of the living room as she takes another sip of wine and licks her lips suggestively.

"So," she says, setting down her glass with a decisive click, "it's time for some truth or dare." She looks pointedly at you, daring you not to choose truth this time around. "I don't want to have to resort to any more embarrassing physical dares..."

Jane's mother grins knowingly at you, her face flushed with the memory. "Oh, honey...let's just say that your father and I were very popular before we found each other," she purrs, leaning in to whisper in your ear. "And he loved every minute of it." She takes another sip of wine, licking her lips seductively as if recalling the experience.

You can't help but feel a surge of jealousy mixed with arousal at the thought of your mother sharing herself so freely with others, particularly in front of your father. The image stirs something deep inside you, making it difficult to concentrate on anything else. "So," she continues, her voice dropping back down to a more normal volume, "how many is that...ten? Twenty?"

You swallow hard, still unable to believe the picture she's painting in your mind. She smiles knowingly at you again and pats your knee sympathetically. "It's all right, dear," she says sweetly. "Just remember that I'm yours now...and this time around, you get to be the one who watches."

You look up at her, feeling a shiver of anticipation run down your spine. The thought of being in control like this...of watching her with someone else...it's almost too much to bear. "I choose dare," you manage to croak out, your voice barely above a whisper.

"Very well," says Jane's mother, her tone dangerously sultry. She takes another swig of wine before slowly unzipping your fly and lowering your pants, revealing your hard cock springing free from its confines. With a sly grin, she wraps her lips around the head and begins sucking, her hands massaging your shaft as she draws it deeper into her mouth.

Meanwhile, Jane watches on with malicious delight in her eyes. "You like that?" she whispers in your ear, brushing a fingertip teasingly across your overheated skin before circling around to find your sensitive nipple. She begins pinching and rolling it between her fingers, expertly combining pleasure and pain into one mind-blowing sensation.

As you feel yourself beginning to lose control, Jane's mother increases the pace of her mouth on your cock, sliding her hand up and down in time with each thrust of her tongue. Her other hand reaches between your legs, finding your exposed balls and rolling them expertly through your tightening skin. The dual stimulation pushes you closer and closer to the edge, until finally - with a hoarse cry muffled by Jane's mother's lips - you erupt, spurting hot cum across Jane's hand as she continues to work her magic on your cock.

You feel the aftershocks wrack through your body, leaving you weak and shuddering in their wake. Slowly, Jane releases you from her mouth, leaning in close so that your lips brush against hers as she whispers: "Good boy." She then holds out her hand to reveal a thick strand of your come glistening on her fingers, still wet and sticky

Jane's mother blinks in surprise at your outburst, then casts a glance over at her daughter. "Well, it seems you're not the only one who needs some practice with their truth or dares," she says archly before turning back to face you. "Perhaps I should have been more specific with my instructions..." She takes another sip of wine and regards you thoughtfully for a moment before continuing.

"You want Jane to cum, hmm? How badly do you really want that?" Her words are laced with dangerously playful innuendo. "Maybe I should show you just how much I enjoy making someone squirm under my control..." With that, she slides closer to you on the couch and begins tracing tiny circles around your exposed nipples with her fingertips.

"I could do it," Jane offers helpfully from across the room. "But then again...perhaps I should just watch." Her eyes gleam as she takes in the scene before her, eager to witness whatever depravities her mother might inflict upon you tonight.

"Hmmm...what do you say?" Jane's mother hums thoughtfully as she continues to torment your nipples with her fingers, rolling and pinching them between her soft yet surprisingly strong hands. "Would it make a difference if I promised to reward both of us? Maybe..." She trails off suggestively, leaning in closer still until the tips of her breasts are brushing against your cheek. "Perhaps we could find another way for Jane to cum tonight...a much more humiliating and satisfying way." Her voice drops even lower now, taking on a husky quality that promises dark delights to come.

Meanwhile, Jane watches intently, her fingers drumming anxiously against the armrest of the couch as she waits for your response. She licks her lips hungrily, anticipating the pain and pleasure that is sure to come when you finally make your choice.

Jane's mother smirks knowingly at you as she continues to toy with your nipples. "Well then," she says, her voice low and sultry, "it seems we have a deal." She leans in closer still until their faces are only inches apart. "But first," she breathes into your ear, "I want to see just how much pain you can handle..." And with that, she pinches hard enough at one of your nipples that it feels like it's about to snap off.

Meanwhile, Jane watches eagerly from across the room as her mother begins to undress her. "Don't worry," Jane whispers throatily, her voice barely audible over the sound of your own labored breathing. "I've been wanting this for a long time..." She slides off the couch and kneels between her mother's spread legs, positioning herself so that their eyes meet as she takes Jane's wet folds in her hands and begins to stroke them expertly.

Your wife Jane's mom closes her eyes and lets out a soft moan of pleasure, arching her back further into the couch. You can see the tension in her muscles beginning to ease as Jane works her fingers deeper inside. "Faster," she whispers urgently, "I need it faster..." Her other hand comes up to grip at your shoulder, pulling you closer to her until you're practically nestled between their bodies.

As Jane speeds up her ministrations, you feel the rhythm begin to build in your own groin as well. You're desperate to release the tension that has been coiling tight inside of you since the beginning of this night, but at the same time, part of you doesn't want it

Ohhhhhh myyyy gooodddd, you naughty boy! You promised not to make her cum...but with your throbbing cock inside of me like this, it's just too much to resist! Granny moans loudly and begins riding you, her breasts slapping against your chest as she grinds her hips in a delicious rhythm.

Jane watches on hungrily from the sidelines, her fingers curled into tight fists at her sides. "Is that what you want?" she taunts, leaning forward to whisper hot breath against your ear. "Do you like seeing them together? Because I can think of so many other ways we could enjoy ourselves tonight..." Her hand slips between your legs, finding your aching cock and beginning to stroke it in time with the motions of Granny riding you.

You're barely coherent at this point, consumed by pleasure and desire as you watch Jane torment her own mother while being pleasured yourself. The ache in your groin becomes unbearable as Jane works you closer and closer to the edge, her touch all that stands between you and release.

With a final, agonized cry, you explode deep inside of Granny, painting her inner thighs with your hot cum. She collapses forward onto your chest, panting heavily as she comes down from her high. Jane smirks at the sight, satisfied for now...but you know better than to think she'll let you off easy anytime soon.

Mmmm...we love you too, baby boy. You've been such a good slave tonight...but don't think that means we're going to let you off easy tomorrow. No siree. In fact, I have plans for you that will test your limits even further. But don't worry...we'll make sure to take care of you along the way. We wouldn't want our precious slave getting too worn out now, would we?

So, sweet thing, why don't you finish yourself off with a nice, long stroke? Think about all the things we've done tonight...the pleasure and pain we've shared. It should be enough to drive you wild. And when you come, remember who made it possible. Remember your place in this little family of ours.