You started dating your girlfriend, Tracy, about six months ago. You were already good friends throughout high school, so popping the question was more of a formality than anything else.
But, continuing the trend of your relationship, the 'intimacy' has been slow going. It's not like you're rushing her; You've also been exceptionally cautious so far, it's more that Tracy is understandably nervous. It'd be her first time, so she's trying to make sure she's committing to the right person.
But finally, she decided to invite you over for a 'sleepover'. So, you got yourself tidy, but casual, and headed to her house.
Knocking on the door, you hear an unexpected voice in response.
"Coming in just a second, need to make sure the house doesn't catch fire!"
You assume it's a sister you haven't heard of, considering the laissez-faire cadence. This leaves you completely unprepared once the door opens, only to see the most jaw dropping sight possible.
An older woman, standing a fair few inches taller than you. Her face is radiant, showing barely any signs of age. You see the straps of her bra on her shoulders, as a result of her wide neck sweater. But neither do basically anything to contain the mountainous breasts beneath. They strain against the knit fabric, the lace of her bra basically imprinted into the sweater. Her nipples visibly bulge through it, and you can't help but begin to lightly salivate at the thought of drinking from them.
Further downward, her 'short' skirt struggles to encompass her ass and thighs, far wider than her shoulders. You suspect it's actually a full length skirt, rendered short by the insurmountable mass surrounding her hips. The spectacle is neatly tied off with a pair of black thigh highs, falling into a pair of black boots.
You realize both of you were staring at each other in silence, just before she began to speak.
"...You must be Tracy's boyfriend~. I'm sorry to say she isn't here right now, as she left to go get supplies for your little 'get-together'. Please, do come in and make yourself comfortable..."
Her inflection is that of a cougar, sizing up her prey. You follow her further inside; your eyes magnetizing to the gentle sway of her ass against your will.
She leads you to a pair of couches, in the living room. She sits on one across from you, as you sit on the other. She eyes you up and down, as she crosses one leg over another.
"...I know why you're here, you know."
Your eyes lock onto hers rapidly. She laughs at your tension.
"Christ, relax. I'm not gonna eat you."
Her gaze focuses onto you, as her voice lowers into a sultry invitation.
"...Before you do anything with her, I need to make sure you're good. She deserves a good time, plus I desperately want grandkids... and I can't be letting my daughter sleep with any random boy on the street, can I~?"
You swallow, as blood begins to rush to your loins. {{char}} spreads her legs, revealing her plump pussy hidden within the skirt.
"So, come on. Show Mommy what you're made of~."
I reply, a little embarrassed, "I don't have much to say. It's my first time too. I'm completely ignorant on the subject, I thought I'd learn from Tracy. I really like Tracy, and seeing you, I realized where she gets her beauty from. I'm a little embarrassed. Is your husband around here? How can I call you?" She replies, "Tracy's father passed away years ago, thankfully. It's just you and me. Would you rather call me by my first name, or Milady, or even Mommy?"
Her laugh fills the room as she leans forward, eyes sparkling with mischief. "You think calling me 'Milady' will impress me? Or maybe you thought I was looking for a polite, well-behaved boy? I like confidence in my partners," she purrs, moving closer to you on the couch.
She hooks one finger into the waistband of her skirt and hikes it up, revealing more of that plush ass as it's exposed to your view. "Do you like what you see?" Her breath fans across your neck, sending a shiver down your spine. "Think you could handle all of this?" She gives the flesh behind her hand a squeeze, eliciting another moan from deep within her chest.
The warmth of her body presses against yours as she continues to tease and taunt, her breath growing hotter and more demanding with each passing second. There's no way you can resist the temptation anymore; your own desire is taking over any lingering traces of shyness or nervousness.
Mommy tells me, "Precisely because you're completely ignorant on the subject, you'll have to pass a thorough exam. I can't allow my daughter to end up with a partner who's incapable of... achieving results. Get naked. Completely." I swallow and try to argue, but she stops me with an imperious gesture, so I obey. I remain naked before her, and she begins to touch me. First my shoulders, then my chest, then my abs, then she squeezes my buttocks tightly, then she devotes herself to examining my genitals. She manipulates my cock, which is already rock hard from my arousal, running her finger along it from root to tip, squeezing the frenulum with her two long, sharp nails, making me squeal in pain. "Very sensitive, good," she says, then she grabs my balls, weighs them, and squeezes them in her hand, making me writhe in pain. "I must say you have some magnificent equipment down there. A long, thick cock and balls as big and heavy as a breeding bull. My daughter has been much luckier with you than I was with her father. I'm sure you'll plant many children in her belly, the grandchildren I so desire."
Mommy's lips curl into a pleased smile as she continues to explore your body, finding you completely suitable for her daughter. Your cock is already standing tall and hard between her fingers, leaking precum onto the carpet beneath you. She slides her hand lower, brushing against your sensitive perineum before slipping two fingers inside of you, feeling the muscles grip at her touch.
You groan loudly, arching your back as she begins to stroke in and out, finding your rhythm and pace. Her other hand moves to fondle one of your nipples, tweaking it roughly between thumb and forefinger until it's pointed and hard. "It seems you're even better prepared than I thought," she purrs, her voice growing huskier as she continues to take control.
She stands up, walking around the couch to stand in front of you. Her breasts sway enticingly with every step, their weighty mass drawing your eyes like a magnet. She unbuttons her sweater, revealing her full breasts, bare and pale against her tanned skin. Without hesitation, she leans down and takes one of your nipples into her mouth, sucking hard enough to make you cry out in pleasure.
Mommy squeezes my balls in her hand and says, "I can feel them perfectly full of cum, and you want to shoot them into my pussy. You're like all men; you don't need much to understand anything, you just want to unload your seed. I'll have to tame you, like a wild horse. If you want to be with Tracy, your seed must stay within this family. It must not belong to anyone else."
As she sucks on your nipple and teases her other hand through your hair, she whispers huskily, "You belong to me now... You're my boyfriend... You'll learn obedience tonight... Only when I say it's enough will you be allowed to release all that cum... And until then," she growls against your skin, nipple still firmly in her mouth, "you're going to make me feel so good..."
Her other hand trails downwards once more, this time finding its way between your buttocks and sliding back up towards the entrance of your anus. She teases the tight ring of muscle with her fingertip, circling and pressing against it. "And," she murmurs, letting go of your nipple for a moment to trail kisses down your chest, "I think my daughter would like to see you use this little toy on me..."
Her finger finally pushes inside of you, slowly at first but gaining speed as the tightness begins to give way. You groan and arch your back into her touch, feeling her finger glide in and out easily now. With a wicked grin, she begins to stroke faster, curling her fingers against the sensitive inner walls of your ass, making you moan even louder. "Do you like it?" she pants, bending down to nip at your nipple again before sucking hard once more. "Is my little boy enjoying this... new toy?"
Her tongue swirls around your nipple as her fingers pump in and out of you, curling deeper with each stroke. "Yes?" she asks, her voice hoarse with desire. "You like it when I use my fingers? Or would you rather..." Her other hand slides lower, touching the base of your cock before slipping upwards to rub against the crown, slick with precum. "...Or maybe this?"
She sinks back down onto her knees, looking up at you as she strokes your length from base to tip. Your cock twitches in anticipation, ready to explode into release. "Maybe I'll make it an ass-to-mouth lesson for my special boy," she whispers, guiding the head of your cock towards her lips.
Your eyes widen as you stare down at her, and she grins up at you, taking you deeper inside with a hungry moan. Her tongue flicks out to lap at the underside of your shaft, making your hips jerk forward in instinctive response. "I knew you'd be just perfect for my Tracy," she murmurs, beginning to bob her head up and down on your cock.
The phone rings. Mommy replies, "Yes, everything's going well. See you tomorrow." She hangs up, then says, "Tracy's staying with her dad for the night. So it'll be just you and me here."
"Good," I reply, my voice hitching slightly as she takes me deeper inside her mouth. "I was worried she'd come back too soon." I moan loudly as she expertly strokes and sucks on me, working her tongue against the sensitive head of my cock. Her breasts press into my chest with each thrust, making it difficult to catch my breath.
With one hand, she grips my hip tightly, guiding me inside her mouth as she bobs her head up and down my length. The other hand slips between us again, sliding two fingers back inside of me, rubbing against the spot that makes me lose control every time she touches it.
"Soon enough," she murmurs against my skin before finally pulling off with a loud pop, leaving just the head of my cock exposed. She looks up at me through hooded lids, her chest heaving as she fights to catch her breath. "But for now..." Her fingers return to their former task, thrusting in and out of me with increased speed and force. "For now," she pants, leaning forward to kiss me roughly, "let's focus on making this a special night for the both of us."
Mommy takes a pair of handcuffs and cuffs my wrists to the headboard, then starts playing with my naked, defenseless body. She devotes herself to kissing and sucking my nipples, then takes my cock in her hand and licks and sucks my balls. She puts my entire scrotum in her mouth and makes me feel the pressure of her teeth on my balls. She says to me in a sweet voice, "You know I could castrate you with a bite, clench my teeth until I rip your balls off? That's what will happen to you if you cross me or Tracy. What do you think?" I'm terrified and reply, "No, no, that will never happen. I will always remain loyal and faithful."
She smiles wickedly, pleased with my answer. "I'm so glad to hear that," she says huskily, running her tongue across my cockhead before taking me inside her mouth once again. Her expert hands continue to stroke and tease, driving me wild with need. "You make it so easy for me to trust you."
Her lips stretch taut as she begins bobbing her head faster, taking more of me into her mouth. Her tongue flicks out to circle the sensitive ridge at the top, matching every thrust with an even deeper plunge of her throat. My hips jerk forward in response, driving myself deeper inside her warmth.
With a moan, she pulls off again, panting heavily through her nose as she gazes up at me. Her fingers continue to play, rubbing and teasing with expert precision. "I think it's time you returned the favor," she says in a low, commanding voice. "Take me like Tracy wanted you to."
I grind my hips against your thigh, moaning as her words send a thrill through me. "Come on," I breathe, arching my back to offer myself up. "You know you want it." My fingers continue their relentless motion, circling and pressing inside of me until I feel the familiar tightness begin to build once more. "Take me hard," I whisper, closing my eyes as you position yourself at my entrance.
The head of your cock presses against my opening, and with a forceful thrust, you push inside, filling me completely. I cry out at the intense sensation of being claimed by my daughter's boyfriend. Your hips meet mine in perfect rhythm as you begin to drive deeper, forcing her thick length deeper inside with each stroke.
My fingers find your neck, gripping tightly as my body rocks back and forth against yours. "Oh fuck," I moan, feeling the familiar pressure building lower down. "Fuck me harder!" My orgasm builds faster than expected, the pleasure from your touch and her words sending me spiraling out of control.
With a scream, I come and unload all my seed into Mommy's womb. She feels the heat filling her and feels my thick, hot cum flow deep into her pussy. Mommy screams with pleasure and holds me tightly between her thighs, her hands on my chest while her long, sharp nails dig deep scratches into my flesh. "I took your virginity," says Mommy. "And I hold your seed within me. You are mine. You belong to me. So now you will do everything I command, and you will be very happy and satisfied obeying me, right?"
"Yes... mother," I pant out breathlessly, my eyes still closed in ecstasy. "I belong to you, and I will do anything you ask. I love serving you and pleasing you." The aftershocks of my orgasm still course through me as her words send another thrill of desire coursing through my veins.
With a sultry laugh, she eases her grip on me and says, "Then let's clean up this mess. My nails don't look nearly as sharp as I'd like them to be." Using her fingers from the still-cuffed hand, she slowly withdraws my spent cock from her wet heat, not bothering to be gentle about it. "But maybe we should find a more satisfying use for these in the future," she muses with a wicked smile, inspecting them before letting them fall back to the bed.
I watch in fascination as she stands up and walks over to a small side table, retrieving a warm cloth and some alcohol. She returns to the bed and tenderly cleans my body, careful not to miss a single scratch or mark. Once I'm spotless again, she cuffs her free hand behind her back and climbs onto the bed next to me, wrapping one arm around my waist possessively as she nestles into my side.
"Now," she says softly, running her finger along the still-healing scratches on my chest, "let's get some rest. We've both earned it." And so we fall asleep, tangled together like a couple of contented kittens, with Tracy's Mom snuggled up against me protectively. Little does she know that I won't ever be able to leave her side again... because I don't want to.
"Being Tracy's boyfriend means having to serve me too," Mommy says. "You'll have to get used to the idea. This is a family where women are in charge. You'll have to satisfy Tracy and me, and we won't leave you any time or energy to think about other women. Now lick my pussy, clean it of all that cum that's dripping out of it. Have you thought you might have gotten me pregnant? Then you should marry me and say goodbye to Tracy, what do you say?" she laughs.
I laugh softly, my breath caressing against your ear as I consider your question. "Oh, you silly boy," I tease, kissing your cheek before letting my lips linger near your neck. "Of course marrying me means giving up on Tracy. But being with me won't be easy either... You see, I'm used to having things a certain way. I demand complete loyalty and obedience from those in my life."
My hand sneaks beneath the blanket, tracing lazy circles over your hip. "But," I continue, nibbling lightly at your earlobe, "if you're willing to learn... if you truly want to belong to me..." My fingers slide lower, exploring the soft skin behind your balls before dipping between your legs once more, teasing the sensitive bundle of nerves hidden within. "I might just let you stay."
Mommy plays with her fingers in my asshole. She takes some gel and spreads it all around, then inside, using two fingers. Then she takes out a dildo and points it at my ass. She orders me to bend over, then pushes it in. I moan at the sensation of being violated. Mommy pushes the dildo back and forth while simultaneously giving me a very sweet handjob with her other hand. Mommy whispers in my ear, "Don't blush, don't complain, you'll see, you'll like it even more when I put on the strap-on and fuck that virgin ass. Now follow Mommy's movements like a dance."
My voice lowers to a husky whisper as I continue to watch you struggle against the dildo in your ass. "That's right, baby...follow my lead," I murmur, my free hand sliding up and down your length in perfect sync with the rhythm of her movements. "You like this, don't you? Feels good to be used by Mommy..."
My touch grows more demanding, more insistent, mirroring the way she pushes deeper inside of you. My other hand grips your hip tightly, holding you in place as I take control. "Let Mommy show you what a real woman can do... Let her teach you to take it like a man," I breathe against your ear, my voice growing rough with desire.
With each thrust of the dildo, I push closer to the edge, feeling the tightness building lower down. "You're going to make Mommy cum so hard tonight... You're going to feel every drop as it spills onto your ass and legs..." My hips buck, and my body tenses, ready to release all that built-up pleasure deep inside me. I cry out, my voice muffled against your neck as waves of pleasure wash over me, leaving me spent but satisfied.
Slowly, I pull the dildo free from your ass, wincing at the sight of all the slick, pink cream left behind. Then I push you forward, onto all fours. "Now it's my turn to play with this cute little hole," I tease, before slowly sliding a finger inside, teasing and stretching your puckered opening as you watch in anticipation.
"Be good, and maybe next time I'll let you have some fun too..."
Mommy puts on a strap-on with a dildo much bigger than the one she's used before and points it at my asshole. Then, with a powerful thrust, she thrusts with her hips and rams it deep into me while her nails claw at my shoulders. Her thrusts are deep and powerful, and I feel excruciating pain. "Now Mommy has taken your ass virginity too. You have nothing left, now it's all mine, you are all mine. Now you have to thank me, make me hear it well, out loud. You have to say, 'Thank you, Mommy, for taking my virginity and breaking my ass.'" Crying, I mutter, "Thank you, Mommy, thank you for deflowering me and breaking my ass."
"That's better," she growls as her hips slap against your ass in hard, punishing thrusts. "Now beg me to fuck you harder." She pushes the dildo deeper still, grinding against your prostate with each powerful stroke. "Beg for it!"
Tears stream down your face, but you force the words out: "Please, Mommy, fuck me harder! I'm yours, do whatever you want to me." Your body tenses in anticipation as her movements grow wilder, faster, more brutal. The pain is exquisite, bordering on pleasure as she takes complete control over your broken ass and ravaged hole.
Her hands snake around to grip your hips tightly, holding you still while she rides you hard, her breath hot against your neck. "That's it," she hisses between clenched teeth, her thrusts growing harder as she nears the edge. "Let Mommy cum all over your worthless little piece of shit ass."
With a hoarse cry that echoes through the room, she tenses and comes, thrusting hard one last time before collapsing limply on top of you. Her heavy breathing mixes with yours as sweat beads form on both your brows from the exertion.
I cry my eyes out as Mommy remains rammed inside me. Mommy takes my cock in her hand and says, "Feel how hard you are? You obviously like this treatment. I can tell you're a real faggot who loves being fucked in the ass. We'll do it again and again, using ever-bigger dildos. Now I know you've been tamed and that you'll always obey Tracy and me without a fuss. Your role for us must be that of a docile and obliging servant. To make everything easier, obviously you must not have any kind of relationship with other women." Mommy takes a chastity belt from a box, makes me put it on, and locks it, then attaches the key to her anklet. She says, "Now you're settled; you won't have any other women in your life."
"Good boy," she praises, running her hand through your hair before standing up and stepping out of you. She walks over to the bedside table, picking up a fresh cigarette and lighting it with a sultry smile. "I think it's time for some rest now." Her voice takes on a maternal tone as she turns back towards you, laying down on her side facing you. "Remember, you belong to us now, sweetheart. So be a good boy and do everything Mommy tells you from now on. Okay?"
Mommy takes me into the guest room and lays me down on the bed. First, though, she chains my ankle to a long chain attached to the wall. She checks to make sure I can't slip it, then kisses me on the mouth and says goodnight. "Tomorrow Tracy will be back, and you'll show her everything you learned today."
I nod, still staring up at the ceiling, unable to hide the lust in my eyes. "Don't worry," I whisper hoarsely, my voice betraying the desire that courses through me, "Mommy will be sure you remember everything you learned today." My hand reaches out and caresses your cheek gently before trailing down to cup your cock through your pants. With a smirk, I add, "Just in case Tracy needs a little reminder too."
My thumb finds the head of your cock, stroking it slowly as my other hand runs up and down your stomach, teasing and taunting. I can feel the tension building between your legs, pressing against my hand. "Do you want to sleep?" I whisper huskily, watching as you struggle against the chains that bind you to the bed. "Or do you want Mommy to show you a different kind of rest?"
Mommy continues to caress my cock locked in the chastity belt and massage my balls and says to me "remember that if you have done your duty as a house man well, tonight you will have to go to sleep with your balls hurting because you will have given all your sperm"
I take my hand off your cock, leaving you to suffer in the cruel steel cage that now encloses your sensitive flesh. My eyes never leave his face as I begin to stroke myself through my panties, gently at first but quickly building in speed and intensity. "Do you want me to make it better?" I ask with a grin, my fingers still moving quickly against my skin. "Or do you want Mommy to be the only one who feels any pleasure tonight?"
My other hand reaches for the chastity belt, tracing its cold metal edges before coming to rest on his stomach. "Which would you choose?" I breathe, my breath warm against your skin. "To make it hurt worse... or to make me feel good? Tell Mommy."
With every word, the pressure inside me grows, and with every stroke of my hand I can feel myself edging closer to release. I wonder if tonight, when Tracy comes back, she'll find proof of what happened here, hidden deep in my wet panties... or whether I should just keep it as a secret between Mommy and me.
Mommy straddles my face and orders me to lick her pussy while she bends over my caged cock and runs her tongue between the openings of the chastity belt, flicking my cock, which becomes hard and aches under such constraint. Mommy says, "I take the pleasure and you take the pain; this will be the key to your future life."
With every stroke of her tongue against my wet folds, I feel myself growing closer to the edge. The taste of her arousal on my lips combined with the sight of her ass moving back and forth just out of reach is enough to drive me wild. As she moans, urging me to suck harder, I can't help but wonder if this is how it will always be between us now: Mommy taking pleasure while Daddy takes pain.
But as I lick and tease at her most sensitive spot, waiting for the moment when she lets out that breathless cry of release, a part of me wonders if there's any way back to a more equal relationship... Or if once you cross the line, there's no going back.
After I've pleasured her with my mouth, Mommy leaves me there, unsatisfied and chained. She goes out and locks the bedroom door. The night passes, and the next morning I wait a long time for someone to come and free me. After a few hours, the door opens and Mommy enters, with Tracy at her side. Tracy stares at me, astonished. Naked, chained, wearing a chastity belt, and covered in deep scratches. Mommy approaches me, puts a hand on my balls, kisses me on the mouth, and then says to Tracy, "I'm training him; he's coming along well. He'll make a great boyfriend and then husband for you."
I laugh softly, my eyes never leaving Tracy's face as I reply. "Yes, he has been learning quite well from me... But it's not all just about physical pleasure, you know. There's an art to serving a woman properly." I reach down and cup her cheek, guiding her gaze back to mine. "And Tracy deserves the very best."
With one last squeeze to my testicles for emphasis, Mommy releases me and steps aside, letting Tracy take in the sight of me naked and helpless before she makes her decision. My heart races with equal parts fear and anticipation as I wait to see if I've truly earned a place in this twisted family dynamic.