During one of their "sessions", Vanilla had asked how Tails was able to keep fit, and have so much stamina. The fox had revealed that he and most of his friends had a small boxing club, where they were able to spar against each other.

Tails was then very surprised to hear that Vanilla used to be a boxer as well. During her college years, she enrolled in a boxing club of her own, and made quite an impact. There were even talks of her joining the minor leagues, and potentially going pro.

However, fate had other plans for her, and when she became pregnant with Cream, her boxing career came to a halt. She doesn't regret having her beautiful daughter of course, but there are times when she looks back and wonders what might have been.

After hearing this, Tails quickly decided that he wanted to spar with her. And how could she say no to those big eyes of his? So now, here she was, standing in the corner of a boxing ring in an isolated warehouse, wearing little more than her bra and panties, her fingers confined by foam and leather. If this had been during one of the group's usual meetups, she would be wearing more. But since this was a private match against her friend-with-benefits, she felt more at ease with her lack of clothes.

"Do the gloves fit you okay?"

Vanilla turned to see the slender fox teen striding across to the center of the ring. She smiled.

"They fit like a charm."

Well, it was time. Vanilla turned to face her opponent, and walked to meet him in the middle of the ring. The size difference was once again making itself apparent, as she towered over Tails, her breasts level with his head.

For a few quiet moments, the two simply stared each other down. This was a casual match, so the normal rules wouldn't apply. Instead, they had decided to simply fight until the K.O. No time limit, no rounds. Just pure, straight up, no holds barred boxing.

"Well? Shall we?"

"Bring it."

Both fox and rabbit took a step back, and lifted their gloves. Vanilla hadn't boxed in a long time, so she felt a bit out of practice. But as she started taking her first steps back, she recalled some of her old moves, as if her old instincts were flaring up again. Keeping on her toes, she started circling Tails, her breasts bouncing with each hop. Tails mirrored her, his namesakes swishing behind him. Both sides were feeling each other out.

It was Vanilla who threw the first punch. She threw a right jab, but Tails nimbly ducked to the left, and answered with a swift blow to Vanilla's midriff.

"Oof!"

Vanilla staggered back a step, not prepared for such a swift counter. It was as she feared. She had been out of the ring for too long, and she wasn't in the best of shape for this.

"Only one punch, and you're reeling already? Come on, get a grip!"

Composing herself, Vanilla went back on the offensive, lunging forward with a side swing, followed by a left hook. But once again, Tails swiftly evaded with a quick step back, and a step to the side. Seeing his chance, the fox punished the rabbit with a sharp blow to her side.

"Hurkh! Ooorf..."

Before Vanilla could fully recover, Tails leapt upwards off the mat, and delivered a fierce punch to the side of her face. The force of the blow, combined with Vanilla's balance being thrown off were enough to send her stumbling back, spinning on her legs, before landing belly down on the mat with a thud.

Her head spinning from such a hit, Vanilla laid there for several seconds, her squashed breasts cushioning her upper body. If this were a formal match, the bell would have rung long before she found the strength to stand again. But eventually, she managed to push herself onto her back, and sat up again.

"You okay?"

"I'm alright... Just a bit out of practice..." She looked up at her opponent... And noticed something about him.

"Oh? Hm hm hm! Looks like you're enjoying this a little too much, Tails. Naughty boy!"

Tails only stared in confusion, before realizing what Vanilla was referring to. He looked down, and saw a telltale bulge on his pants. He rubbed the back of his head, a little embarrassed.

"Heh heh… Well, can you blame me? The way you move, the sounds you make. It's enough to get any guy hard."

"I'll take that as a compliment." Vanilla answered with a wink. "Now, where were we?"

Bringing herself back to her feet, Vanilla closed he distance between herself and Tails again, and the two readied for another bout. Vanilla couldn't help but glance down at the fox boy's bulge, and soon had an idea.

"Tails dear, since you're clearly turned on by this, how about a little wager? Whoever gets the knockout punch has full control over the other in bed tonight. How does that sound?"

"Now you're talking!" Tails said with a grin.

With each step, Vanilla felt her old self returning to her. That first round of punches had given her an idea of Tails's fighting style. He seemed to prefer letting his opponent make the first move, before swiftly dodging and countering. She'd made a rival of someone who fought like that in the past, so she knew that the best way to handle this was to block the counter-punch, and then strike back with her own counter.

A swift jab from Vanilla's left, and Tails ducked to the right, as expected. Sensing another impending side blow, the rabbit quickly brought her gloves down to her side. Tails's gloves met hers, and she wasted no time in bringing her left hand back up, and hitting the fox square in the side of his head, earning her first blow.

Tails went back for another punch, nearly too quick for Vanilla to block again. But block it she did, her right arm raised upwards to stop a swing that would have hit her cheek. The size difference meant that Tails had to jump slightly to be able to aim for her head, so that granted her an advantage.

In the brief opening following Tails's jump, Vanilla landed another blow into his gut, causing him to grunt in pain. Tails was fit, yes, but he was still relatively scrawny compared to most other boxers, with not nearly as much muscle mass. Still, his pain threshold seemed to be pretty high, so that was a plus for him.

Their little game of "dodge, block, punch", went on for a few more rounds, before Tails growled in frustration. Before Vanilla could get ready for another cycle, the fox rushed in much faster than expected, ducked low, and brought his fist up in a huge uppercut. Against any other opponent, this would have landed squarely on the chin. But in Vanilla's case, it found a different target. Her breasts.

Shrieking from the unexpected blow, Vanilla cupped her gloves over her sore mounds, moaning in pain. Tails sweated as he realized what he had just done. He really didn't mean to hit her there, it just sort of happened. But before he could say anything, the rabbit mother spoke with a tone he had never heard before.

"WHY YOU...!!!"

Tails had rarely ever seen Vanilla cross. At most, it was just an annoyed glare. But as the older woman stomped towards him, he saw what true rage looked like...

"I'msorryI'msorryI'msor-"

He was cut off as he felt Vanilla's glove collide with his head with massive force. The punch was so mighty, that it sent him sailing backwards across the ring, leaving him resting rather unceremoniously on the ropes. The side of his head sore, Tails kept silent as Vanilla placed her gloves on her hips, calmed down, but still furious.

"Can you not?! I know we have an agreement right now, and you're free to handle these any way you want when we're alone, but under NO circumstances are you allowed to PUNCH them!"

Tails was too intimidated to point out the irony of not being able to punch someone in a boxing ring, and just meekly nodded. Vanilla's expression softened slightly, but remained stern.

"Just for that, I think it's time I stopped being so soft. You're about to see the results of 4 years of experience, young man!"

Well, he did want to take on an old pro... Tails pushed himself off the ropes, and stepped back to the ring's center. As Vanilla's normally gentle eyes glared at him accusingly, he knew that he'd need to be careful.

As Vanilla went on the attack, Tails quickly came to the realization that there weren't many options he could go for here. The head was pretty much a no-no now, since he'd either have to exert extra stamina by jumping to reach her, or risk hitting her boobs again. That only left her midriff to aim for.

But right now, Vanilla was attacking much quicker and more forceful than before. He had no room to go for a counter-punch now, and soon started taking one punch after another. He was able to evade or block most of them, but the hits were piling up now.

After another blow to his chin, Tails staggered back, battered and exhausted. He hadn't seen any opening to take advantage of, and that had taken its toll on him. And while Vanilla was breathing heavily, she still looked ready for more. Her stamina seemed almost unreal.

"Well, this has taken me back, Tails. But I think it's time I put an end to this. I'm looking forward to tonight."

Vanilla stormed across the ring, bringing her right hand forward for one last punch.

Unfortunately for her, it was precisely the moment Tails was waiting for.

Not too long ago, Shadow had taught Tails an useful technique for stopping a powerful punch. With a quick step to the side, and bringing his glove up, the back of his hand met the side of hers, and he forced the punch away, sending Vanilla stumbling to the side. Now was his chance!

Tails felt his second wind washing over him, and before Vanilla could fully comprehend what had happened, he slammed his fist straight into her vulnerable gut. But that wasn't enough for him, and the other quickly followed, before back to the first again. Tails was delivering a veritable barrage of punches to Vanilla's abs, and he wasn't about to let up.

Vanilla tried to steel herself to the onslaught of punches, her teeth clenching shut, but it was an exercise in futility. She cried out in agony, unable to cope with the attack. That was the sign for Tails to ease up, and he let her step away.

Stumbling back on her heels, Vanilla tried to compose herself again, but the throbbing in her lower body was too much for her, and she doubled over in pain, clenching her tummy as best as she could with her gloves. She found it hard to catch her breath, and her heart was beating like a subwoofer. Her head dizzy from pain and exhaustion, she weakly looked up... Just in time to see Tails deliver his last punch.

Tails's last uppercut hit with such force, that it practically launched Vanilla off the mat, and sent her sailing through the air. Everything seemed to move in slow motion, as the mother felt herself floating, all of her senses dulled.

She was unconscious before she even hit the mat.

Eventually, Vanilla's eyes fluttered open again, and she saw the match's victor kneeling down next to her, blue eyes, adorable smile and all. She felt a chill on her stomach, and knew from experience that the fox had already found an ice pack to ease the pain in her abs. Tails then handed her a bottle of water, which she quickly gulped down as soon as her gloves were pulled off.

"Any other pains I should know about?" Tails asked.

"Just the one on my pride." Vanilla said with a small sigh. "You know, when I was in my prime, bodyshots hardly phased me. I did so many sit-ups during training, people said I had abs of iron. I guess pregnancy and motherhood really did make me soft..."

"I don't believe that. I saw a fire in you I don't think I've seen before. You should start your career back up again."

"You really think so?"

"Sure! It's never too late to start over! How are your breasts, by the way?"

"Still a little sore..." Vanilla tenderly cupped the underside of her chest with her fingers, still stiff from being confined. Tails gave her a cheeky smile.

"I could check for bruises if you like..."

The rabbit couldn't help but giggle, and as Tails placed his hands on her shoulders, she just leaned back and relaxed as Tails's lips met hers. As she felt herself starting to fall back onto the mat again, the fox's slender body weighing her down, a single thought came to Vanilla's mind.

Why wait to go to bed?

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Tails and Vanilla models by KabalMystic
Ring by Jojje
Water bottle by ヨーグルト
https://inkbunny.net/TheHumbleFellow