Ian had to be just about the cutest little thirteen year old boy you could find! At barely five feet tall, he was indeed diminutive and elflike. He had a cherubic face: chubby cheeks, bright green eyes, shaggy red hair, little button nose and a tiny little pointed chin. He was pretty fat too for his age, almost one hundred and twenty pounds! Oddly enough most of it avoided his belly and went into his hips, thighs, bulging butt and perky, budding little b cup boytits, his nipples constantly erect and rosy pink,poking through whatever fabric he was wearing over his chest. His butt was especially big and wide for a boy his age, his ass easily swallowing his tight white briefs. The only thing truly small on him had to be his tiny little five inch dick. Ian had known the very nice lady who lived down the street for as long as he could remember. She was very fond of him, playing with him often, and everytime there was the need she begged to babysit him. Little was he aware of her true, dark, sexual intentions, which she had been waiting to spring upon him for some time, at least until he had started puberty. Ian didn't mind much because she was so beautiful. Besides her features she had an incredible body: She was very tall, chubby, and had absolutely massive breasts and asscheeks, so big that most of Ians body could probably be smothered by her clevage. Ian was walking home from school, unaware that she had already had pulled some strings and had blackmailed Ians parents to give him to her and was now speeding toward his normal route from school to catch him before he got home and realized something was out of place.

(I'm thinking that she should pull up  in front of Ian and tell him his parents told her she could have him for a few days since they decided to go on an impromptu vacation, maybe she offers him a ride home to her place, but she carries him into the passenger seat, and she puts him into a car seat in the passenger seat, and as she's buckling him in, her massive tits smush and jiggle all over him before she gets back in the drivers seat and drives off with him. I'm thinking maybe the carseat itself has like a bump in the seat where his asshole is and the strap acts like a bra that gives him epic boy clevage.)

Regan Leer had sped most of the way towards Ian's school, but now that she had him in her sights, the shemale slowed down, cruising by the young boy as her window rolled down slowly. "Hi, honey~" she said with her trademarked, honeysuckle voice, "Your parents sent me to pick you up from school today, sweety... They're going away for a while, so they wanted me to look after you." She blushed a little, eyefucking the fat ass on the teenager, wishing she could be seeing it jiggle naked in front of her at that moment. Stopping the car, not even waiting for him to agree, she got out of the driver's side door, slinking around her impressively-sized sedan and pressing the boy into a hug, lifting him up off the ground, his face buried in her massive cleavage.  Rubbing his face across her tits, Regan purred down at him, "You'll be my little baby from today on, alright?"  Opening the door for Ian, there was already a car seat prepared, and she seated him down in it, hands caressing his tender body. Fingers rubbed at his nipples coyly, tucking under his breasts and rubbing at his tight little package, all bulged up at the front. Clicking the pink seatbelt around him, she adjusted the straps in the middle to push up his tits, wiggling her finger between them as she stroked his lips with the other finger, "Now, what do you have to say to Mommy Regan?"

Ian was a little surprised but still exquisitely happy to see one of his most favorite people. “Aunty Regan! So nice to see you! What are you doing here?” Ian was a little perplexed at the unusualness of it all, this had certainly never happened before, but he trusted Regan with his life and was about to agree when she rushed out of the car and came around to immediately grab him and pick him up by his fat booty and shoving him face first into her gigantic breasts before he could so much as protest. Ian wasn't sure what to make all of this, but it could be certain he was getting turned on like he never had been before. As she pressed his face into her ass his little five inch cock began to harden and began to poke at the underside of her bosom. If this was being a baby, Ian liked it so far. Ian was a little uneasy when he saw the carseat though. “Is that really neccesary?” Ian protested weakly. It certainly didn't stop Regan from stuffing his fat ass into the carseat. She pressed him into it, rubbing his nipples. Ian shuddered, amazed that she so blatantly rubbed his package and then began playing with his tits,  setting them so that they made some beautiful clevage, which frankly embarrassed him a little. In response to Regans question, he answered. “Um, thank you?” Ian was a little too perplexed and a little to horny to think straight as she got back into her side of the car and began to speed back to her home.

(How about as she's driving Regan says something like she just so happy to have me over she can't wait, and then maybe she makes a comment about how eager my dick seems, but then she degrades it as being too small, but then reassures me that she actuallky likes the fact that I have a small dick, maybe she even pats it  or something, then maybe she changes the subject to like how fat I'm getting, but she talks about it like it's a good thing, maybe she makes a comment about my boytits in particular before we arrive and she carries me inside her house, maybe carrying me by my ass and holding me so that my face is shoved into your clevage, maybe then you take me into the family room and sit me on your lap and tell me that I'm actually going to be your son from now on or something like that.)

Regan Leer: :smiled to herself as she got back into the car, her fat booty smooshing down onto the seats, making the car lean to one side just a bit.  The shemale drove off to her house, stealing sideways glances at Ian, the smile still pasted onto her face. "I see someone's happy to see me~" she teased, reaching over with one finger to stroke up and down the underside of his cock slowly, gently caressing his tiny prick.  "Your little willy likes me, Ian..." she pursed her lips, bringing the moist finger up to his lips and rubbing it across them, "You look like you've gained weight, too..." She reached down, sticking her hand between his breasts and giving his boy orbs a few gentle gropes, "Soon we might have to get you a training bra!" Regan beamed, pulling into her driveway, "I can't wait to take you shopping for one, sweety!"  Stepping out of the parked car, Regan went around to the other side, disengaging the child locks from the outside, and admiring Ian for a few seconds. She tussled his hair and pinched his cheeks, gurgling cute nonsense talk for a while before unbuckling the seat, lifting him up into her bosom once more.  Sitting him down in the family room, Regan kept him in her lap, one hand around his tummy, rubbing it playfully as the other mussed his hair up. "I've got some good news, Ian... Your parents are going to be living abroad for two years, and they've passed your legal guardianship onto.... Me!" she squealed in delight at the end, kissing his face with a big, sloppy kiss. "Isn't that wonderful! Now I can be your Momma, and you can be my pretty little baby boy!" 

Ian was a little perplexed by all of this, certainly feeling quite embarrassed but at the same time incredibly turned on by all the attention she was giving him. Ian was outright shocked as she felt down and stroked his cock a bit. All he could do was further blush as he stammered “d-don't call it little.” Ian was not quite as shocked but was still getting used to the pattern as she began to comment on his weight and in a happy voice said she'd have to take him shopping for a training bra. Her groping hands sending shivers down his spine. Ian could only smile as she loved him more, shoving her tits in his face and picking him up out of the carseat as she carried him into the house, her busom jiggling against him with each step. Due to being pressed into her busom by her immense strength, Ian couldn't see much other than her massive boobs and her face as she carried him and put him in her lap on the couch. Ian listened intently as she held him to her breast, playfully fondling his belly. His jaw dropped as she told him she was now his legal guardian, but for reasons he couldn't fathom, it made his little pecker all the harder, making poke into her massive jiggling busom. “T-thats great” Ian stammered, not precisely sure what this would mean for him.

(How about she begins to lay down some rules and tell him about some things shes going to change, like maybe she asks him how he would like to lose his virginity, maybe she tells him that he'll need to start gaining weight on a regular basis, oh, and maybe it would be hot if she stripped him naked and tied that little ribbon around his cock, afterwhich she could give him his first feeding as she vigorously jacked him off.)

Regan Leer murred softly, stroking Ian's tummy fondly as she wiggled her fingers down into his pants. Thick digits rubbed across considerably smaller length as they trapped his member between them. Gently rubbing him, Regan cooed softly as she bounced her chest up and down around his face. Working his pants off, the fox nuzzled his face affectionately, "I'm going to make you the prettiest little girlie ever..." she whispered, stroking his cock with every word. She stopped rubbing him, and pulled out a little baby blue ribbon, tieing it around the base of his cock snugly. Lifting off the rest of his clothes, she stripped him naked, cuddling him up to her massive breasts. "I think it's time for baby to get fed~" she teased, slipping one gigantic breast out of her shirt, rubbing the drooling nipple across his lips. "Open up!" she said, fingers wrapping around his tool, wanking him off quickly. "Be a good girl and eat your fill, and Mommy'll make you feel good~"

Ian nearly froze as his dick was touched for the first time by someone else. Ian was well aware of her strength as she grabbed his dick in a nearly iron grip. Slapping Ians face around with her tits also served to further distract him from the fact that Regan was slipping off his pants. Ian closed his eyes and rubbed his face back against her ni kind, feeling her warm cheek rub against his. Girl, the thought of being transformed into one made a chill go down his spine, knowing he would be further reviled and made fun of by those who knew him if he went out in public again. His dick however had other plans and grew even harder as she jacked him off a bit before tieing the ribbon around the base of his cock. It made him feel a little uncomfortable and really showed just how small Ian was. No sooner done did she strip him completely naked. He really was at her mercy now. Ians eyes however glazed over in wonder as she finally revealed one of her massive breasts to him and forced his mouth over her nipple, holding his head to her breast as she began to vigorously jack him off. Ian drank heartily as he felt the warm, delicious milk flow down his throat, warming his body. He particularly began to feel a tingling and warming sensation in his butt, crotch and breasts as his belly slowly filled up. His belly would soon begin to round and bulge, the sensations becoming more and more intense until Ian came in her hand, milk dribbling from his lips and his jizz coating her hand and the underside of her breasts.

(I'd like it if she was proud of him cumming, calling him a good boy and stuff like that, maybe some of his cum got on her dress so she needs to disrobe and how him her cock and her massive ass. Maybe she takes him into the bathroom and they have a bath together and mommy cleans every little crevice of her baby and maybe asks him how he'd like to lose his virginity, like she sort of sees it as a pity thing because in her mind, that will be the last time he puts his cock in any woman. Maybe after that if you're willing to go this far she takes him dries him off and puts him in front of a vanity mirror and does his hair and makeup and picks out a very skimpy, slutty outfit for him.)

Regan Leer murred lowly, dragging her tounge across her lips slowly. "Oh honey... I'm so proud of you" she cooed, reaching up with a cumstained hand to stroke his face, marking him with his own seed, ""You're going to be my darling little girl, cumming so easily like that..." Shi looked down and giggled. "Oopsie!  You got some on my dress..." Regan put him down on the couch, slowly stripping out of her dress. The curvy herm's G cup breasts bounced heavily, sloshing with all the milk they contained, while her cock sprang free of its confines, the foot-long semi-hard member backed up by two melon-sized nuts.  "Now... isn't that better?" She turned around, picking up her dress, bending over and showing off that wide, luscious rump, crack deep enough for an equine to lay his pipe down and still disappear between.  Tossing the dress into the laundry room, Regan picked Ian up, and carried him over to the bathroom. "Now, does my widdle baby want a bath or a shower with Mommy?"

Ians eyes gleamed with love for his mommy as well as with the afterglow of that wonderful orgasm he had. Ian could feel the hot seed still on her hand smear onto his face. Ian felt somehow even more aroused by the humiliation, of having his face covered in his own cum. She really was helping him along in becoming even more of a sissified fatty faggot,revealing how weak his little cock was by showing how easily he came. He felt so vulnerable in her arms. She knew how weak and unmanly he was. Ian noticed the cumstain on her dress and watched as she did a lovely striptease for him. Not only did she reveal the total glory of her massive nips, but his mommy massive butt-busting pipe also sprang forth. Ians humiliation knew no bounds to be faced with such a huge cock. He almost felt like crossing his leg over his cock, if his thighs weren't so thick as to make it impossible! Ian continued watching however, enjoying looking at her huge, fat, soft round ass, one that could probably hide him in it with ease. Ian laughed gleefully as she lifted him up into her breasts once more. He shook his head eagerly as she offered. ”Ooh, mommy, I wanna take a bath with you. Thats the best way to make a fat faggy baby like me clean right?”


Regan Leer murred and lead her son off to the bathroom, drawing some water while she cradled him on her lap, stroking his face softly as she forced one of her nipples into his mouth, letting him suckle on her delicious milk.  Her cock sprang up from between his legs, for a few minutes making him look impressively hung. She took hold of his little member in her hand, pressing it up against hers and rubbing them together slowly. Once the tub was full enough, she set him down into the water, standing over him in her impressive fullness.  She practically blotted out the light with her thickness, and she looked down at him, "It's time for you to feel the only pussy you'll every know, Eaan..." She held him down onto his back, lowering herself onto his tiny length, his cock not even penetrating past her labia, "Mhmmm... Are you in yet?"

Ian wiggled his fat little booty on her lap, his belly and boyboobies giving a bit of a jiggle as well. went gaga as she pressed his face into her nipple again, her breastmilk flowing down his throat once more, the effect similar to catnip. Ian wrapped his arms around her gigantic tit. Only to be rather erotically surprised as he felt her gigantic cock rise up from underneath him, giving Ians little cock another raging hard on at knowing how small his cock was compared to his mommys. Ian moaned on her tit as she rubbed their cocks together, the tip of her cock flopping against his face, quite literally rubbing his face in it. With a loud pop Regans nipple came out of his mouth, Ian licking his lips of her milk as she put him in the water. Ian looked up at his mommy with awe as she hovered over him, her massive bulk, her wide hips and gigantic titties pressing against him, her cock trapped in her clevage as she sits on top of Ian, the unbelieveable pressure of her weight making Ian feel really good. Ian couldn't say anything with her tits smashing his face, but Ian eagerly tried to get his cock up into her vag. Ians face was hot and wet against her busom, his breath travelling up her clevage as he desparately wiggled his hips to fuck her pussy.


Regan Leer grinned as she felt him trying to fuck himself into her sopping wet pussy, the herm rubbing herself all over his tiny length.  After a few minutes of riding him, she furrowed her brow, sitting up. She reached down to stroke his flaccid length with a finger, "Awww, does my widdle baby not like his mommy's pussy?" shi teased, flicking his cockhead gently, "Maybe she was right when she thought he was a little bum boy..." She eased him over onto his front, bending him over the side of the tub, careful to make sure he didn't drip everywher onto the floor.  She clicked her tounge at him as she reached down to spread his fat asscheeks, leaning down to nuzzle his tailhole. Her tounge flicked out across the tight pucker, chowing down on his cute little butt for a while before going up to sandwich her cock between his fat cheeks. Taking a handful of assmeat in each paw, shi wrapped it around his meat, gently fucking his rump. "Mhmmm... Isn't that better, baby?"