The pregnancy took very quickly - quite possibly that very night, though you hardly only tried that night. Soon enough, there's that old holiday, the Day of Gratitude, and you and Lily head to her mother's home. Her father died a while back, and he was an only child, so it's pretty much just Lily and her mom for the Day of Gratitude; as such, you head along with her, to help liven it up a little and offer another person there.
Lily's mother, Rosie, is a beautiful woman, with wavy, vivid red hair, even brighter than Lily's. She greets you in this gorgeous orange sweater with a cutaway hole for the cleavage to let the skin breathe, and not much in the way of anything below the waist, the sweater reaching down a little past her ass. Girls need to expose their skin to air, after all. "Welcome, Mac," she says, with a big smile on her lips. "I hope that us being your only company isn't too hard on you. You're looking particularly handsome - you really got a keeper here, Lily," she says, with a teasing smile over at Lily.
"Thank you, Ms. Dundel," you tell her.
"Oh, please, call me Rosie," she says, with a smile and a faint blush. "Ms. Dundel makes me sound so old."
"You certainly don't look it."
She giggles sweetly at that. "It's so nice to see you both again," she says, wrapping the pair of you in a big hug, pulling you close to her, practically snuggling herself against both of you. While Lily blushes a little, Rosie just snuggles you both close. "Ah, it gets so lonely here," she sighs, as she finally pulls away from you both, stepping back a moment, stretching. "Oh, I know, we could play some Chancer," she says, stepping into the hallway for a moment, disappearing from sight to acquire some board game or box of cards or whatever.
Lily leans close to you. "I think you should, you know." She tilts her head a little, blushing as she does it. "She's so lonely, like she said, and, I mean, it's not like you haven't, with other girls," she explains.
You smile, pulling her into a thorough kiss, your tongue forcefully invading her mouth. She gently shudders as she's gripped in your arm, as your tongue wriggles along her palate, as her own limply bats at the underside. Her breasts strain against her thin top, and your own shirt, and you finally break off the kiss, panting for several seconds. "I'm so lucky to have a girlfriend like you, especially given you're likely to age as gracefully as your mother, and remain drop dead gorgeous." She blushes at that, smiling. "Are you sure? I can be a bit domineering with other women..."
She fidgets. "W-well, just be nicer to her," she tells you, with her brow furrowing. "C'mon, she's my mom, not some, sorority slut," she tells you, with a small frown on her lips. She gently whaps your bicep.
You just smile. "Kidding," you tell her, soothingly, and she scowls momentarily at you. "Do you have any advice for me? She is your mom."
"Just be nice," Lily says. "I'm sure she'd be happy to receive your attention, especially if I'm there cheering you on."
"Here it is," Rosie calls out, carrying in a small box - a bit bigger than a deck of cards, but much smaller than your typical board game's. "Do you two know how to play Chancer?" She asks.
"No," you admit.
"Oh, it's very simple," she tells you. "You want to get a certain hand, and there are bets, and-" it's basically Poker, but with a smaller deck (2 each of A,10,J,Q,K for each player, and one wild card) alright?
"How about we make it strip Chancer?" You suggest, with a smile.
Rosie blushes a vivid shade of red, her eyes widening. "A-ah, w-well," she stammers out, glancing over at Lily.
"That sounds like fun, Mac," Lily says. "Don't you think so, Mom?" She leans against you, one hand gently stroking your chest through your shirt, drawing her mother's attention to your muscular upper body. Rosie swallows audibly and visibly.
"If Lily is okay with it, then it sounds like fun," she says, after a moment, shaking her head to get back in the moment. "Chancer is very easy to make into a Strip version of the game, since the game is so much about controlling your hand," she explains, settling down at the table. "I used to play Strip Chancer a lot back in college," she tells you, with a giggle.
The first round of cards is doled out, each of you getting fifteen cards. You wind up with two aces and three kings. The three of you glance at one another, as if trying to size each other up. You can fold before changing cards to avoid losing any clothes, but that isn't a terribly fun variant, and you have a great hand right now.
Rosie loses three cards from her hand, but neither you nor Lily dump any, which does make you a tad nervous that she has a good hand. You don't have the Joker, after all. Fortunately, it turns out that Lily's hand was two Tens, two Queens, and the Joker, while Rosie had two Aces and two Jacks, so you have the best hand still, with a Kings high full house.
As such, you just lean back to watch them take off their clothes. Lily pulls off her t-shirt with reckless abandon, revealing a lace black lingerie bra that looks positively delicious on her pale skin. Rosie only blushes just slightly as she says, "Well, I suppose I can't just go for socks after that," laughing momentarily as she pulls off her sweater. She's wearing a plain white bra, and plain white underwear as well. Both girls are blushing, just a little.
The next round, you draw two Aces, two Kings, and a Jack; you dump the Jack and get a Joker, while Rosie holds onto her cards, and Lily abandons three. As it turns out, Rosie has a straight, which means you and Lily both have to strip; you take off your top, and Rosie's eyes immediately go to it, her breath quickening just a little as she drinks in your muscular, bare chest, her cheeks turning a delicious pink, while Lily peels herself out of her skirt, leaving her just in black lace lingerie.
The next round, you draw three tens, the Joker, and a Queen. You consider for a moment exactly what to do. Do you really want to win this? You'd get to see Rosie show just a little more skin, but probably she'd only take off her socks for that one... on the other hand, you could show her more than that. You wonder if the size queen gene is shared between the pair.
You dump four cards; the tens and the Joker, ruining an excellent hand, turning four of a kind into two pair as you draw two Jacks, a Queen, and an Ace. Rosie dumps three of her own, seeming not to be too satisfied with her own set - which turns out to be two pair as well, Kings and Queens.
Lily has four of a kind - four aces - which beats both your hands. While Rosie removes her socks, you pull off your pants, letting your hard cock rest visibly within its confinement in your underwear. You stand up for longer than strictly necessary, careful to angle your body so that Rosie can see your erection, swallowing audibly as her gaze is drawn to it. Lily's own smile is almost impish as she notices her mother staring, her mouth opening as if to say something, then falling closed again.
You finally sit down, and that jars Rosie out of her lust fugue, shaking her head rapidly as she shuffles the cards anew, her breathing a little heavier than before, her cheeks warm with arousal.
"How do you, ah, h-handle Mac?" Rosie asks Lily, glancing over at her daughter as she deals out the cards.
"Handle?" Lily tilts her head for a moment, then she opens her mouth. "Oh! It feels really good," she explains, with a quick nod and an easy smile. "It's big, so it really gets in there deep, rubs over everything." Rosie swallows, nodding, glancing at her hand before tossing away one card. "But it doesn't hurt or anything. It's soooo good."
Your own hand is two Tens, a Queen, a King, and a Jack. You wind up dumping everything but the tens... and upgrading it to three of a kind Tens. Lily loses two cards and comes out with three of a kind Jacks, beating you and Rosie alike - all Rosie has is three tens too, and that's with a Joker, a truly baffling hand for somebody who only lost one card - wooping a little and watching you with lusty eyes as you stand up.
You could pull off your socks, but with the way that Rosie and Lily are both staring at you with undisguised lust, you know what you want to pull off next. You pull down your underwear, letting your rock hard cock pop free, the thick length bobbing in the air. Rosie's jaw drops, saliva running over her lower lip as she simply stares at it, her breath heavy as her breasts rise and fall. She's not stripping herself, she's so distracted by your length... you could probably step over to her and have her suck it and she wouldn't resist, judging by the look on her face.
"You can get a closer look if you're interested, Mom," Lily says, with a bright smile on her lips. Rosie just nods dumbly, and you step closer towards her, your cock getting right in her face, and she goes cross-eyed as she stares at it. One hand gently reaches up for your cock, fingers gently running along your length, drool accumulating in her mouth as she stares and strokes, not even thinking about the fact that this is her daughter's boyfriend's cock.
You let her, smiling down at her, before leaning forward, undoing the strap on her bra from behind. She blinks up at you, confused for a moment. "You lost a round," you remind her.
"O-oh, yes," she says, with a nod. She swallows. "It's so big," she breathes out. "Does it really feel good? It looks like it would hurt."
"It feels wonderful, Mom, don't worry," Lily says, with a big smile on her lips. "We can stop playing Strip Chancer if you want to just play with it." Rosie simply nods, staring at your hard-on, going cross-eyed as her fingers play with it.
Rosie's hand gently runs across your length, fingers brushing across the underside. It's not a handjob, more an exploration with her fingertips. She noisily drinks in your scent, her bare breasts jiggling a bit at the sharp intake of breath through her nostrils. She sighs at the smell, clearly enjoying it, and leans forward to lick the tip, swiping away a dollop of precum and humming at the taste. "It's so, so much bigger than my husband's... twice as long," she explains. "He always felt wonderful inside me, but this..."
"It'll feel even better," Lily says, and while her mother seems too distracted to notice, Lily has pulled out her phone, surreptitiously putting it in a position to record, balanced on the box so the camera catches all the ongoing action.
You can see Rosie's panties growing soaked, her nipples rock hard with arousal, as she continues to gently toy with your cock, fingers brushing along the underside of the head. She shifts, her hips twitching just a little from her position sitting before you, and her eyes unfocus for a moment in what you almost suspect is a miniature orgasm.
You really want to just grab the back of her head and see her throat bulge, but you let her take her time, her tongue occasionally flashing out to wipe away some of the drool that's accumulating on her lower lip. "Is it alright if I..." she trails off, as if lost in thought or unable to complete the sentence.
"Go ahead, Mom," Lily says happily, still in her underwear as she watches her topless Mom lean forward to lick at the cockhead a little more thoroughly, her mouth widening in anticipation of taking your entire thick cock into her mouth.
You just watch, letting her take the lead for the moment. Her lips stretch around your cockhead, her features distorted as her cheeks hollow to accommodate your sheer girth. Her tongue rubs along the underside of your cock, as she gently, slowly, begins to slither down your length. Seeing those brown eyes of hers, staring up at you, soulful and sweet as she takes your cock even deeper into your mouth. Her hand strokes what of your cock isn't in her mouth - which is most of it. Her tongue waggles back and forth, straining across it, finding every vein - and you hit her throat, making her sputter and peel back, drool running down her chin as she quickly catches her breath. She wipes at her mouth, staring lewdly up at you with unfocused eyes, and you softly pet her, running your fingers through her hair.
Lily chimes in, then. "Just relax," she tells her mother. "It's big, but you just need to relax and take it," she explains, and her mother nods, the mother-daughter combination making this entire thing all the more erotic than getting your dick sucked by a lonely MILF would otherwise be. You gently direct her back towards your cock, and her mouth opens wide, her eyes closing. Her hand strokes up and down your length in languid strokes, as her tongue rubs back and forth while she inches her way ever further down, her throat bulging to accommodate your cockhead.
It's a very pleasant feeling, watching the nearly-naked older woman slither down your cock, but it takes little time for your cock to make her gag again, saliva splattering out of her mouth, hitting your thighs and testicles as she takes you to the base. A quick, sharp intake of breath through her nose, and you groan in pleasure, simply closing your eyes as you enjoy the feeling of her mouth around your cock, her throat squeezing on your length, starting to gag gently around it, like her throat was her pussy and she had just come.
Your free hand runs down to her breasts, gently squeezing one in the palm of your hand, and it pushes her over the edge, making her legitimately orgasm, a strangled moan escaping her throat as nothing more than a "gkkk" as her tongue flops around. The sweet vibrations of it, the pleasure, and of course, the intense feeling of power and dominance as she sucks you off like that, all drive you absolutely crazy, your fingers digging softly into her tit.
Eventually, though, around halfway down your cock, she's arrested in her movements - you're just too big, too long, for her to handle, and she pulls back, sucking in air, staring up at you with a drunken look in her eyes. "Puh, please," she pants out, "I want, to take it all."
Lily's the one who helps, then, her pale skin beautiful in black lingerie, hopping up out of her chair and getting behind her mother. "I think it's easier to take it in your pussy," she tells her, in a soft voice. Rosie just nods dumbly, and you grab her under the shoulders, easily hefting her up onto the table, her legs dangling off the side; a quick grip of her panties, and she's completely naked before you, your rock hard cock staring at her tight, velvety snatch, which has been unused for so long...
You grip her hips and slowly push into her. She squirms on your cock, breath quickening, growing ever heavier, her eyes rolling up. Her fingers claw at the table beneath her, her head casting back and forth as she shakes on your cock. She's tight, almost uncomfortably so, her pussy clinging to your dick as you force your way inside her. Your fingers dig into her hips, as you push your way ever deeper into her. You groan and grunt, your cock twitching wildly within her tight pussy, your brain simply shorting out with pleasure as Lily watches with a smile on her face while you fuck her mother. It's completely different from fucking Naia or Clea, those random sluts - it's almost like deflowering Lily again, even though of course her mother's no virgin.
When your cock is about halfway inside her, Rosie orgasms hard, gasping and jerking, her back arching as her cunt squeezes taut on your dick, straining and rolling around it as she shivers in a mix of ecstasy and pain, her breath heavy, saliva splattering wildly around her face as she comes. Lily simply leans forward, gently wrapping her mother in a hug, holding her as you continue to grind your way ever deeper inside her.
You're really glad you went back on the pill, because there's something absolutely intoxicating about taking Rosie like this, and you're not sure you could pull out if you have to. You just stare down at Rosie, panting, fingers digging into her hips, and keep pushing. She winces and squirms simultaneously, pleasure and pain mixing together on her face, her skin growing slick with sweat. Her nipples are hard and perky, her cheeks a lovely pink, and your fingers claw at her skin as you finally finish forcing yourself deep inside her.
The moment you bottom out, the tip of your dick kissing her womb, she gasps and comes anew, her cunt squeezing, wriggling, working over your cock. Lily tightens her hug around her mother, and you join her in pleasure, finally simply unloading inside her, filling her up with a thick load of cum right then and there, her whole body twitching wildly beneath you.
When you're completely spent, you gently, slowly, pull out of her wonderful cunt, and Lily gets down on her knees, cleaning you off with her mouth, as her mother simply rests there, staring up at the ceiling blankly, completely exhausted from just one thrust.