Cute for Generations
Now, what I would like to happen is basically similar things that happened in the previous story. Size Difference, BBW, boobjob/titjob, belly hug and kisses, body sitting and so on, in short Big "torturing" Tails with her body. Tails at some point could try and climb Big's body (again, depending on their size difference) to kiss her, all while teasing her by kissing, touching and cuddling her sensitive body parts (maybe even licking her pussy and nipples).


A few months have passed since Tails had gotten together with the massive girl known as Big the Cat, or Biggie as he affectionately called her, and they’ve been living together in Biggie’s Mystic Ruins wooden hut ever since. The huge cat and the small fox would have tons of sex every day, both were pretty much tireless when it came about making love and could last an entire night just humping each other. Tails woke up one day from his usual resting place, which would either be on Biggie’s massive gut or between her gigantic tits. However, while Biggie prefered to sleep on her back, sometimes she’d roll on her back, which resulted in Tails passing the night under her. This time was no exception and Tails found himself squished between her massive knockers and her huge belly. He groaned and tried to squirm his way out without waking her up, no easy task since his entire weight was about the weight of one of Biggie’s feet. Nevertheless he managed to sneak half of his body out her rack, but he underestimated his morning wood which remained stuck on her nipple, jammed in it and already throbbing, begging him for release. He tried to pull away a few times, but it was pointless: the boner had to go or he wouldn’t get free. He huffed and started to hump her warm tit, gritting his teeth and praying that she wouldn’t wake up, despite the fact that she told him that he could do anything to her, while also cupping a feel of her tit, feeling once more the extreme sensation of his hands sinking in the titflesh, then after a few minutes he bit his lip to not scream and arched his back as he came, his jizz gushing out of Biggie’s tit while all she did was purr lowly. Tails huffed as he could now slide out of her tit and flop on the floor, panting and blushing as that was wild, but he was used to it since it happened basically every day. He got up, stretched and groomed his fur, and went towards Biggie’s huge kitchen table to prepare himself some milk and cereal, the breakfast of champions. 


As he ate the crunchy honey-flavoured cereals, he casually looked at the calendar and gasped: today was Sonic’s birthday and they all agreed to throw him a surprise party, something not very easy since Sonic wasn't easy to surprise. He finished the cereals and got down from the chair, bolting towards the bathroom but he impacted with something bouncy and squishy: he had just slammed against Biggie’s gut, his muzzle pressing against her navel, making him blush as he looked up, unable to see her through her massive rack. She giggled and grabbed him under his armpits, lifting him up and making him sit on her titties, scratching under his chin which made him wag his tails. From the way she looked, she was aroused from what he did before.
“Hey, small fry. What’s the hurry?” she asked, smiling.
“Biggie, it’s Sonic’s birthday today! We gotta go help organize the party!” said Tails. 
“Huh? Oh, right, it was today!” said the huge cat, facepalming “Quick, into the shower!” she said, carrying him into her massive shower. Everything in her house was huge, at least for Tails, but he wasn't complaining about the shower, because it would often end with them doing something naughty, when not full out sexual. Today, of course, was no different as they started out just applying shampoo on their furs, but of course Biggie wanted to tease Tails, so she nudged him in her tits, only his head sticking out, and used them to rub and wash his body, while she giggled as she watched over him like some kind of chubby guardian angel.
“Mmmm… You just love to imprison me with your boobs, don’t you?” asked Tails, squirming a bit as she soaped him up.
“Hihihi, as if you don’t like it yourself…” she giggled as she replied, hugging her tits with one arm as she poured some shampoo on his head and washed his hair, making him coo and wag his tails a bit.
“I won’t lie, it is pretty awesome.” Tails giggled too, then he felt himself pulled out of her tits and brought to her rear. Her fluffy tail was as long as Tails and she used it to wrap him up, three fuzzy coils around his chest to pin his arms to his sides, then she nudged him between her buttocks, his resurrected penis pressing against her butthole.
“Biggie?” he asked, raising a brow while blushing.
“You made me horny, Tailsy. You gotta take your responsability and FUCK my huge ass in my shower…” she whispered as she leaned her ass against the wall, pinning Tails more. He gulped and blushed, but nodded and lined his cock with her asshole and, with a quick thrust of his hips, penetrated her ass. They’ve done anal before, yet her ass was still as tight as the first day they did it, squeezing his cock harshly and dragging it as deep inside as she could. They finished quickly, there would be time for a more thorough sex session after the party, then they washed again, dried and dressed up and finally went out to go to the party.


Little did they know that Eggman would strike at that time with the monstrous machine known as Time Eater, which would tear a hole in the fabric of space and time and kidnapped all the guests at the party while also fusing together the Modern and Classic timelines and allowing the two versions of Sonic and Tails to meet and team-up to save their timelines. They had already saved Tails, who met with his younger self, Amy and Knuckles while also facing Metal Sonic and the Death Egg Robot, and now the two Sonics went inside Speed Highway, the stage where Biggie herself was trapped in, and while they were in there, the two Tails were left out to wait.
“Wow, this woman is huge!” said C.T., gasping in awe as he saw Biggie.
“Yes, she is. She’s my… I mean, OUR girlfriend, you know? In this timeline, anyway.” said M.T., making C.T. look at him, slack-jawed.
“Are you serious?! Me and her?!” asked the small fox, in shock, to which the older fox nodded with a proud smirk.
“Weird… So far, I never considered dating someone, let alone someone so… Colossal…” stated C.T., feeling intimidated by her presence. Then M.S. and C.S. returned from the stage and Biggie regained her color and life again. She smiled and twirled a bit, thanking both Sonics, then she went back to her Tails and pulled him into her massive arms, bear-hugging him between her gigantic tits and swinging him around.
“Oooohhhh, Tailsy! I was sooooo scared! It was horrible, I almost thought I’d never see you again!” she bawled as she smothered his face with kisses and nuzzles.
“But now I’m free and with you, so all is good again!” she giggled before resuming the smooches, which made both Sonics snicker. Then, she noticed Classic Tails looking at her, a bit frightened by her size.
“Huh? What the…?” she said, to which Modern Tails had her put him down and explained everything to her, making her shriek.
“An even smaller, even cuter Tailsy?! OH MY GOODNESS!!” she yelled and brought him into her arms, hugging him and kissing his face and cradling him like a baby. Classic Tails was completely overpowered by her, she was so big and strong and he was nothing but a yellow and white speck amidst an ocean of squishy, furry purple arms. Meanwhile, the two Sonics and Tails watched as she cuddled Classic Tails, and Modern Tails sighed a bit.
“Uh, shouldn’t you do something?” Sonic asked his little brother.
“Like what?” Tails asked back, he knew that there was no way for him to get his younger self out of the predicament he got in.
Then C.T. slipped past her arms and inside Biggie’s massive rack, being squished by her warm, furry tits.
“Huh? What the? He’s gone!” she said, looking around while C.T. tried his best to give a sign of his presence but failed spectacularly, since not only his squirms would go unnoticed but he was also half dazed because he was trying to process what went on since the moment she spotted him. This gargantuan woman had lifted him like he was nothing, smothered him in hugs and kisses and now threatened to drown him in her furry, fat boobs. This was a lot to take  for him!


After she found and fished C.T. out of her cleavage, she stayed put until the big showdown, where she cheered for the two Sonics, and then she chilled with everyone else back at Sonic’s birthday party, of course she kept pampering C.T. by hugging, nuzzling and kissing his little head and now the smaller fox started to like the treatment, understanding why his older self fell in love with her: she was so caring, gentle and adoring that he felt like melting in her loving hug. Then, it was time for the Classics to return home and Biggie sighed as she reluctantly let go of Classic Tails, setting him down.
“Bye, little one…” she said, a bit sad that he had to go. C.T.  waved back and headed for the portal, only to come back and kiss her on the lips, shocking her and Modern Tails as he did so.
“I can’t wait to meet you again.” said Classic Tails, smiling and going back to his time while everyone else waved at the two Classics as they left. Biggie and Tails returned home after the insane party and Biggie flopped on bed, still giddy about what happened.
“That was one of the wildest birthday parties I’ve ever had! Right, Tailsy?” she asked, giggling, to Tails, who seemed… off.
“Huh? Oh, yeah, yeah…” he said, sounding distracted by something.
“And small you? My gosh, I had no idea you were this cute in your early age!” she said, wagging her tail and purring as Tails’s off tone flew right over her head.
“Glad you enjoyed it…” he sighed, but this time she caught onto it.
“Tails? Is everything ok?” she asked, blinking.
“To be honest? No. I kinda don’t like how you swooned all over past me. It’s like… You liked him more than me…” he sighed again, lowering his ears.
“Oh…” she said, getting up from the bed and picking him up, settling him right in her tits and petting his head.
“Well, even though I enjoyed his presence, there are things I can do with you and not with him, darling…” she purred, smiling, to which Tails smiled back.
“I know. Just wanting to sound needy for a moment there. Now, my gargantuan wife, how about you give me some?” he asked, giggling.
“Oh, you asked for it, you cunning, adorable sly fox…” she giggled and smothered his lips with hers in a passionate deep French kiss while she leaned back on bed, topping him as they made out. Tails cooed and moaned as she held him so lovingly between her tits and kissed him with all the love in the world, both their tongues friendly wrestling each other for dominance, coiling and rubbing against each other between their mouths. He was pinned down on bed by her superior weight, and he loved to feel her on him. He missed her touch and kisses, even though it was just for a day, and that spoke how much they were addicted to each other, like a loving sickness both of them couldn’t chase off their minds. She pulled away to breathe, then she sat down, making Tails get up as he wasn’t done. He literally climbed her body, hanging on her tits as he resumed making out with her, now while he groped and caressed her gigantic knockers. Why was her size so attractive to him, when he kinda didn’t like it when people remarked how small he was? Maybe it was her sexual aura, her gentle demeanor, or maybe, deep down, he was just that much into size difference. He pulled away and moved down, taking both of her walnut-sized nipples in his mouth and vigorously sucked, being immediately rewarded with her sweet, warm milk, the same milk she made him drink the first time they had sex and that she gave him every morning for breakfast.


“Mmmmmm, I just love breastfeeding you, Tailsy… You’re always so greedy with my tits…” she lovingly moaned and purred as Tails squeezed her boobs to get more milk out for him to drink, it came out so hard that it started to trickle down his muzzle. Not that he cared at all, he was so much into her that basically anything could happen and he’d just shrug it off.
“Geez, look at you. You’re making such a mess…” she giggled and grabbed him under his armpits, getting him near her face so she could lick the excessive milk off his chin, and then she started her flurry of kisses on his entire being, starting by his face and going all the way down, until he was covered in purple lipstick marks to the point where there was almost any trace left of his former color.
“Mmmbbb… God, you spoil me, Biggie… More… Pamper me more… Treat me like your baby…” he moaned, his dick already growing hard.
“Hihihi, don't be silly.” she said, placing him down on bed “If you were my baby, I wouldn’t be able to do this…” she said, before lifting her massive butt and sitting on Tails’s entire body, squishing him under her massive fat dump truck. He moaned and giggled as the fat flesh of her butt pressed and squished him from every direction, enveloping him in her warm embrace, while she heard her faint giggle as if she was miles away. She rubbed her booty on him a few times, even putting more weight on him just to hear him whimper and grope her massive asscheeks while his cock grew hard again. There was simply no part of her that didn’t turn him on. She lifted off of him after a few more minutes of body sitting, only to then smother all but his head under her gigantic tits, pressing them harder around him and giving him the titjob he so desperately craved.
“Hihihihi, I love being so big and fat and curvy, because you love my big fat curves, Tailsy. And I’ll use every one of them to bring you joy and pleasure.” she giggled as she rubbed her boobs on him, wagging her tail as she watched him bite his lip while blushing and sweating a lot, squirming pathetically between her tits, which she clamped tightly around him so he couldn’t move, something she knew he craved for: to be unable to move as she “tortured” him with her body. He felt his own cock starting to throb, the titjob quickly eroded any control he had and made him arch his back as much as he could and moan in bliss as he came. As usual, no cum could leak out of the massive ocean of her tits, but she seemed to love it anyway as she dismounted him and loomed above him, her belly obscuring the dim light of the lightbulb hanging from the ceiling.
“You thought I’d forget this? Not gonna happen. Hug and kiss this massive belly of mine, Tailsy, before we move over the main course…” she giggled sensually before pressing her fat belly on him, completely smothering him again with it.


Tails tried his best to hug that gargantuan belly but he could barely slide his hands out of it and there was no way in Mobius that he’d manage to fully embrace her, but she loved the try anyway. He pressed his muzzle against her belly and showered it in kisses while his rock hard cock thrusted inside it, making him moan as her warm fat and fur made it for one hell of a sensation. She moaned a bit, purring as she loved what Tails was doing, and rocked back and forth on him, making sure that every single part of him would feel her weight, another thing Tails loved and made sure to tell her to do every time they’d do this. His hands sank in her flesh as he groped it, along with his cock and lips, and he kept tending to her gut until she decided that she was ready for the main course and lifted off of him, giggling as she saw him pant and blush and shiver as he really needed to have full sex with her. She leaned back and spreaded her legs, inviting Tails to come in by waving her tail like a hand. He gulped, got on his knees and crawled between her legs, getting up by holding on to her squishy thighs and lining his cock with her pussy. He bit his lips as he was waiting for it, finally he’d be one with Biggie again. With a quick thrust, knowing that she could take some roughness, he slid his cock inside her vagina, making her moan and hold onto her sheets as Tails penetrated her deeply.
“AHN! Mmmmm, it’s in. Oh, it’s always so big inside me!” she moaned and suddenly closed her legs around him, trapping him against her. He gulped as his arms had been pinned to their sides and only his head, shoulder and chest were visible and, as he wondered how they were going to do it, she started moving him with her legs, making him thrust inside her at quite the speed and power. She told him many times that, being a big girl, she could endure some rough sex and also that she wanted it, but Tails was always afraid to hurt her, knowing that a woman’s vagina is a very sensitive spot. Yet Biggie would always manage to convince him to go hard on her and this time was no exception. And since they did anal this morning, now they could fully focus on her pussy. Tails was being used by Biggie to feel good, but he didn’t mind that. The feeling of her divine pussy mixed with, again, the fact that he couldn’t move while doing so was a massive turn on for him so he just let her do her thing as he just moaned and clenched his fists. They kept having sex for a rather long time, and during all that Tails managed to not cum but eventually he lost it and yelled as his sperm gushed out of his urethra and into her womb, making her moan and purr too as she felt him filling her. Finally, Tails’s cock slid out of her pussy and both stood there, panting and sweating as the afterglow deprived them of any strength. Of course, Biggie being Biggie, she still managed to free Tails and placing him between her boobs, his favourite resting place, and gave him a peck on the forehead, which for him felt like she’d just swallow his entire upper head with her lips, before passing out from tiredness, a dopey, horny smile on her face. Tails followed her in the dream world, him too smiling in satisfaction as a sweet slumber took over them.


The End