Story by Custos
(Original posting 1st of September 2025 on https://inkbunny.net/Custos)

Please don’t repost this story, let it remain in my galleries!
This story contains material for adults only, do not read if you’re a minor.
The material presented is fictional and for adult fantasy only.
The author does not condone any of the depicted illegal activity in real life.

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LuluLovesYou commission: Tender Deflowering of a Baby Boy

- “He’s been a handful, Momma Bear. Constantly nagging Mary to latch, and when he finally gets his way, he barely drinks from her and just plays with her boobs. We don’t know where this fascination comes from!”

The male cougar at Momma Bear’s door is tall and handsome, slender of build and suave, yet his upper arms betray he spends a lot of time at the gym. If the ursine had been only twenty years younger, she wouldn’t have hesitated to ask Damon for a fun romp in the sack. But the dad in front of her is happily married, and is currently in the process of giving the mature brown grizzly bear the bag with all of his baby son’s supplies. Momma is already carrying the one-year-old tyke on her arm, with little Jack pawing at the middle-aged woman’s voluptuous bosom. Which embarrasses his dad greatly.

- “See, there he goes again. Jack, stop that! It’s not polite.”

Momma Bear chuckles at her neighbour’s discomfort, confident that the little one-year-old baby won’t be able to open up her blouse without her help. Not for the lack of trying.

“Just a healthy red-blooded American boy, Damon. Haha. He’ll be quite the ladies man when he grows up. Must take after his dear daddy, hehe.”

It doesn’t escape the mature bear woman’s attention the way Damon looks at her, and especially her shapely breasts. The same ones being fondled by his baby son right in front of his eyes. If ever he’d only take the initiative. She wouldn’t mind. She’s a discreet woman. Nothing makes a man appreciate his wife more than the occasional sip from another’s cup.

- “Oh, haha. Yeah, I guess, Momma Bear. Still, if it gets annoying just correct him and distract him with some toys. I’ll come pick Jack up after my shift.”

The bear woman smiles at Damon seductively from behind her glasses, whipping her flowy brown hair as she waves goodbye to her little ward’s daddy by waving Jack’s little arm towards his handsome father. The car honks one time as it disappears from Momma’s driveway, the gentle mature ursine cooing at the widely smiling little Jack as she carries him inside.

“There’s my handsome little man. Did you have a fun party, baby? Already such a big boy!”

Jack babbles happily, smiling and nodding at Momma Bear as she carries him straight to her bathroom. He’s a cute little guy. Sand-coloured fur with lighter hues at the tips of his fluff and tail, as well as on his tummy. Big sky blue eyes, adorable kitten ears, a rosy little cat nose, and small growing fangs from the corners of his mouth. Jack had his first birthday last week, and Momma Bear had been invited to celebrate alongside family and friends. She’s been babysitting Jack ever since he’d gotten home from the hospital after his birth. Momma is known throughout the neighbourhood as a kind mature woman, and many people let her babysit their kids.

The bathroom is decorated with rose petals, scented candles, and warm bath has already been drawn. Momma Bear had promised her special little man a very special surprise, even though at his age the baby boy has no concept of gifts or promises. The beautiful mature ursine had been adamant to give the cute little kitten a day he won’t soon forget.

Momma Bear lays Jack down onto the changing station in her bathroom, closing the door behind her which dims the light to just the soft glow of the candles. Jack coos, his big innocent blue eyes turning to look at the warmly dancing little flames while Momma starts unbuttoning his onesie.

“Nice and warm and cosy, all specially for my handsome little man. Happy birthday, Jackie boy.”

The little cougar baby giggles and cries out in joy when Momma Bear starts pretending eating him, nomming all over his tummy while she’s gently pulling off his sleeves and worming his kicking little feet out of the onesie. Jack’s belly is soft and warm, and Momma Bear can’t help but plant the sweetest of little kisses all over it while the one-year-old gurgles in happiness.

Momma’s hot breath washes over the baby’s groin while she gently pulls off his diaper, causing a shiver and a happy little sigh as little Jack instinctively raises up his legs to present his bottom for changing. The gentle mature ursine woman has other plans, though, seeing as little Jack is completely clean. Probably changed just before bringing him over by his handsome daddy.

“Now, look at that. If that isn’t the sweetest most beautiful sight.”

Momma Bear involuntarily clenches her thighs together, grinding her crotch against the changing station subconsciously. Her panties are already damp underneath her homely skirt, and her large swollen nipples are stiff as pins while they prick through the blouse barely containing her ample breasts.

Jack’s cute little bottom is presented to the hungry eyes of his mature babysitter, the kitten sucking on his thumb while his big blue eyes look up at Momma Bear with the utmost trust and happiness. He always comes home to his parents in the best of moods whenever Momma Bear watched him. Little do they know why.

“What adorable little boy jewels, Jackie. Just let Momma kiss that sweet little boy pussy for a moment, baby. Momma needs her baby boy!”

The grizzly bear gently takes hold of Jack’s little ankles and keeps his legs up, presenting his adorably pink little hole before her eyes as it opens up like a little rosy flower. A set of cute fuzzy little balls adorn the cute little hole, and an adorable little uncut humanoid boy penis rests comfortably on Jack’s tummy. His long slender cougar tail swishes back and forth excitedly, knowing just how deep and intense Momma’s kisses can be!

Momma Bear manages to only pop a few buttons of her blouse before she dives onto the baby’s little hole like a woman dying of thirst, releasing her big heavy breasts from their fabric prison while her military-grade strength bra holds back the brunt of their heft. Her rosy areolae already squirming to escape that final barrier as well.

Little baby Jack’s eyes fall halfway shut, sighing out the most wonderful of high-pitched coos as his little legs flinch in Momma’s strong grip. Her warm breath washes moistly over the one-year-old’s winking rosy hole and twitching little boy penis, making the baby shudder and mewl in pleasures most infants never get to experience.

“Mm. Sweet and fresh. And ever so sweet. You’re Momma Bear’s sweet little honey pot, Jackie boy. Yes, you are!”

The one-year-old cub squirms in the mature ursine woman’s grasp, thrusting his cute little bum up to meet her smacking wet lips as they seal themselves vacuum to the boy’s tiny hole before Momma’s slick and expert tongue skilfully stretches Jack’s tiny sphincter and slithers effortless inside. The broad slimy organ thrashing around while pushing all of the infant’s pleasure spots, especially that tiny bump that is Jack’s immature prostate.

The middle-aged woman is in heaven, fluttering her seductive feminine eyelids while grabbing both of the baby boy’s buttocks firmly in her palms, intensively and passionately french kissing one-year-old Jack’s tiny tail hole as it spasms and contracts joyfully around her thick slick tongue. Passionate as the foreplay is, Momma Bear has no attention to decorum, and her sloppy deep kisses cause Jack’s little bottom and crotch to be completely soaked in her spittle as well as her own ample bosom.

Little Jack’s tiny cocklet is already stiff as a nail by the time Momma’s tongue finally slips out of his yearning tiny boy pussy and her mouth instead swallows the infant’s penis just shy of one inch long. The creamy soft foreskin is expertly drawn back by the mature grizzly bear woman, and the tiny cherry pink crown of Jackie’s cocklet is lovingly bathed in sloppy suckles and kisses.

“Ooh, Jackie. My sweet little baby boy. Momma has missed your touch, baby. Always so eager and happy to play with Momma, eh? I’m gonna give you the most wonderful gift for a big one-year-old boy like you, baby. Today I’m gonna make you a man, honey. Momma will always be your first!”

Momma Bear’s pussy is sopping wet, her panties and skirt already soaked through the fabric by just the foreplay. Horning herself further up by her own sweet yet dirty talk to the innocent baby boy under her care. She finally manages to worm out of her skirt and panties, ripping off her own bra to let her heavy breasts dangle and bounce like the beautiful globes of womanhood they are. Filled to the brim with her milk, despite her mature age. The many cubs she keeps being entrusted under her care never go hungry, and perpetually keep her milk production flowing by suckling from those delicious big sensitive nubs that ache every minute of every day for a little mouth to feed.

The grizzly bear woman’s body is beautiful and gracefully aged. Her stomach is a little plump, just like her vulva and basically every other curve on her body, without veering into unhealthy territory. Her pussy is glistening in her own arousal, the muscle spasms of her excitement already causing Momma Bear’s slit to ‘wink’, while she desperately pets the throbbing little pleasure pearl at the top of her vertical smile. The button is about the same size as little Jackie’s tiny cock head.

“Let’s get nice and clean before we get dirty, baby.”

Momma bear lifts the blissfully cooing little baby boy in her arms and lowers herself slowly down into the tub of pleasantly warm water. Jack’s big innocent eyes are fluttering in the after shocks of the pleasure his underdeveloped body can barely handle, when he suddenly becomes aware of Momma Bear’s big rosy nipple sliding into view. His extremely young body jerks immediately, thrusting his tiny hard cocklet into the soft mass of Momma’s tummy while he reaches for her breast.

- “Ungh! Ungh! Titti.”

The mature ursine woman chuckles and cradles little Jack to her bosom with one arm while her free hand dives down to diddle with her own aching loins. Her pussy ablaze with the sheer genuine pleasure her touches can deliver to such a wonderful little boy as Jackie.

“Titti, eh? What a polite boy to ask! Alrighty, honey. Now titti. And after the bath, clitty!”

Momma Bear presents the baby cougar boy with her enlarged nipple as she hefts her own heavy breast for him, Jack mewling and humping his tiny erection into her belly button while he gratefully latches on. The middle-aged ursine woman moans loudly and leans back into the bathtub, just losing herself for a moment while her warm motherly milk palpably flows from her aching heavy breast through her sensitive nipple before it is gluttonously swallowed by the hungry little one-year-old boy.

“Mm. Drink up, baby. A boy needs lots of mother’s milk and love to grow all big and strong into a virile stud of a man. Like your daddy.”

Jack just hums as he holds Momma Bear’s ample udder steady with his small paws, his little eyes closed and his tiny cocklet flexing in rhythm with the waves of pleasure and deliciousness rolling down his infantile spine and tongue. A little coarse, like all feline tongues tend to be, but soft and slick on the drawback. With his tiny fingers digging rhythmically into the grizzly bear’s mammaries while purring up a storm.

Momma Bear’s fingers trace all over her swollen cunt lips, teasing herself in anticipation of the big event. Edging herself on the brink of complete pleasure a few times while she nurses the little one-year-old baby she intends to deflower that very same day. Her digits find her pleasure pearl and circle the softest of delightful caresses all around it, causing it to pulse and jerk like a tiny penis. Making Momma shudder in the bathtub while she feeds her neighbour’s baby.

To grant herself stay from execution, Momma Bear’s fingers once again dip into the crevice of Jack’s tiny bottom, eagerly sliding underneath the curling little feline tail as the baby instinctually pushes out his sphincter for her to touch. Enjoying the gentle caresses Momma Bear delivers to his tender sensitive baby anus, almost equally as sensitive as the adult woman’s aching pussy is. And equally hungry to be molested.

“Good boy, Jackie. You’re gonna make some boy or girl very happy some day. And Momma is gonna be very proud to have taught you everything you know and enjoy!”

The bath is warm and cosy, with continuous heavy petting and showers of kisses from Momma Bear for her very special little guy. When she simply can’t take any more, the ursine lifts herself out of the water and tenderly dries both herself and Jack.

The bedroom is equally decorated with rose petals and candles, which Momma Bear lights while her sexy little man wriggles all bare and seductively on the covers of her bed. Without taking her eye off of Jack, Momma Bear takes out a very shear lace set of black lingerie and seductively starts pulling it on for the cub’s curious eyes. Jack seems to like it. His stiff little nail flexes up and down against his little tummy while he keeps his legs up, continuing to expose his pink little bottom for Momma Bear.

“Greedy boy. It’s Momma’s turn for some intimate kisses now.”

Draped in lace garters and stockings, Momma Bear sensually crawls up to the cooing one-year-old baby on the bed, letting her heat warm the infant cub while she seductively lowers her exposed pussy and grinds it against Jack’s penis and tummy. She’s still sopping wet, and strands of her womanly arousal stick to the baby’s fur and penis, connecting the heated genitals of two people with an age gab of over five decades.

Jack’s little penis dances in delight as the heated moist slick warmth of Momma Bear’s vulva caresses the tiny nail up and down, teasing her little man’s hard little length while equally making herself cross-eyed with desire. The mature grizzly bear woman hefts her own breasts in the black lace bra, her fingers digging into the heavy mammaries while she massages herself. Pinches her own aching nipples while moaning in dire need of a man’s love. Even if that man is just one-year-old. Actually, she prefers them this way.

“Ooh, Jackie. Sweettie. You’re making Momma all hot and bothered. Get Momma ready for you, baby. Suck Momma’s clitty, little stud.”

The tickling sensation of the mesh lace fabric against her fur and skin make the woman’s mature cunt sop even more, laying her ample covered breasts over the baby’s face for a moment, letting the one-year-old soak in her motherly warmth and scent. She can feel his tiny length spasm and tap against her swollen slit, the lips of her vulva thicker than his tiny balls are. Longing to devour the tiny innocence in her lustful womanly furnace. Imprint upon Jackie’s young mind the scent, taste, and feel of a woman’s embrace. Subconsciously implanting the seed, the concept of her. She shall always be his first, and the only woman to make his dick harder than any other.

Momma Bear scoots up and presents her aching leaking pussy to the baby’s face, Jack wearing the most wonderful smile after having been smothered in Momma Bear’s ample breasts. The ursine’s clitoris is aching and throbbing, as it is slowly being guided to Jack’s infant lips.

“There you go, baby. Suck mommy’s clitty. Make Momma’s pussy nice and wet for that cute little dick of yours.”

There is no hesitation. Jack’s feline muzzle eagerly seeks and latches onto Momma Bear’s hot pleasure button, making her moan out sluttily while she pinches her own nipples through the lingerie. The boy’s eyes close and his raspy pink cat tongue laps quick shallow licks along the underside of the grizzly bear’s clitoris while his lips suck vacuum around it. The warm swollen lips of Momma Bear’s cunt are naturally spread while she straddles the baby, allowing her vertical smile to place sticky wet smooches all over Jack’s tummy, chest, and neck while the baby boy nurses hungrily from her clit.

“Ooh, Jack! Such an eager little gentleman! You make Momma feel so so good, baby boy. I… I can’t wait any longer. I need you inside me, baby. Happy first birthday, little stud.”

Finally, Momma Bear cannot deny herself any longer and scoots down to straddle the one-year-old kitten’s lap, dragging the chubby lips of her swollen vulva down Jack’s entire body and leaving a sticky trail. Bathing the baby in the scent of her aroused womanhood.

Briefly, Momma Bear grinds her enlarged clitty against the baby’s cocklet, duelling the tiny glans in a miniature sword fight. And then, without even needing to reach down and guide her immature lover, Momma Bear’s pussy seems to take in a deep gulp and swallows the one-year-old baby’s stiffy in one smooth motion. All the way down to the root, squeezing her sopping wet cunt lips against Jack’s tiny balls as the baby gasps in surprise. A wet velvety heat enveloping his cocklet like he’s never known before, even more heavenly than Momma Bear’s luscious lips. Momma Bear feels the small length pulse inside her, her mature pussy clenching down on the throbbing tiny penis as if trying to suck it right off Jack’s infant body.

“Ooh, Jackie. Baby. I’ve longed for this moment for so long! I’m your first, baby. Momma’s popped your cherry! Your little cocklet is deep inside mommy’s pussy, honey. My good, big little stud!”

Warm creamy mother milk seeps from Momma Bear’s nipples, soaking the lace fabric of her black lingerie while her body starts to move on its own, in pure instinct to breed this baby boy of just one year old. Despite her rampant horniness, Momma is gentle and tender with her infant ward, allowing Jack to soak in the pleasure without becoming frightened of so many overwhelming emotions and sensations.

For his own safety and comfort, Momma Bear’s strong womanly hands grasp his flailing wrists and pin Jack’s arms to the bed while she rides him like a cowgirl. Taking the utmost care not to lean too much weight down upon the fragile little baby, but just enough to bring the both of them heavenly delight. Momma Bear’s vulva is positively oozing her female arousal, soaking the baby’s whole lower body in her scent and juices, producing the lewdest of sexual smacking sounds each time she plops her curvy ass down on Jack’s infantile pelvis. His little one inch penis is stiff as a nail and throbbing chaotically, Jack’s large baby balls nearly swallowed whole by the bear’s pussy as her cunt lips pluck at them with each thrust of her womanly hips.

“Mm. Your little cocklet feels so good, baby. Reaches just all the right places. Breed Momma, little stud. Momma wants to cum together with her little boy!”

Momma Bear is more riling herself up further than expecting a baby to actually cream her aching pussy, the adult woman keeping the baby firmly pinned down into place while gyrating and impaling her squelching womanhood upon his tiny spear.

Jack is nearly folded double with his knees pressed against his tummy like when he’s being changed, Momma Bear fucking herself upon him looking almost as if she’s the one penetrating the baby! His eyelids are fluttering and he’s seeing stars, babbling and mewling in bliss and just a little bit of terror, overwhelmed by the sensations very few babies get to experience.

Finally, the grizzly bear slams down her hips one last down, her heavy breasts bouncing as droplets of motherly milk spray everywhere.

“Yes. Yes! YES! Cum for me, baby! Cum for Momma!”

Momma Bear’s pussy nearly strangles Jack’s tiny cocklet as waves of intense ecstasy ripple through the ursine’s body, making her shudder and convulse. The baby too stiffens like a board, mewling out a pitiful coo while his tiny stiffy pulses with the sensation of his very first intentional dry orgasm. Jack’s tiny balls are drawn up high against his body and swallowed up inside Momma’s winking pussy, and his tiny pink hole equally contracts invitingly towards the otherwise empty room as his small perineum flexes in pumping out non-existent semen.

The mature ursine woman throws back her head into her neck, sending her brown wavy hair flying into all directions while pearls of sweat roll down her neck into her ample bosom. Deep within her loins, Momma Bear can feel those powerful contractions and spasms, her clit throbbing in absolute bliss as she has taken another baby’s virginity. She’ll always be his first. And he’ll always have a place in her lap and bosom. Whenever and wherever he wants.

Jack starts crying a little, his powerful immature orgasm confusing and scaring him just a little bit. Momma Bear gently lies down next to the baby and comforts him, offering Jack her seeping fat nipple once more. She positions the baby boy in such a way he lies in the crux of her neck, with his bottom towards her face, and the lascivious woman tenderly sucks his twitching tiny penis to comfort him further. Adding a finger tenderly rubbing and circling the one-year-old’s infant anus is the last comfort Jack needs, the little boy soon dozing off to dreamland while sleepily continuing to suckle Momma Bear’s breast.

“Sweet dreams, baby. Momma loves you.”