MILF Profile
Name: Alicia Acorn
Age: 51
Species: Chipmunk
Spouse: Maximillion Acorn
Children: Elias Acorn, Sally Acorn
Miles 'N MILFs
Chapter 3: Tails X Alicia
Tails slowly opened his eyes. Just as the young fox was about to stretch, he felt something wrapped around his body. As his mind tried to register the situation, he looked down to see that his head wasn't resting on a pillow. The two tailed fox's head laid upon a large set of breasts. Looking up, he saw the face of Cream's mom, Vanilla the rabbit. The older woman appeared to be asleep, as she held his body close to hers.
Memories of what he'd done began to pop into his head. "Oh man, I can't believe I let that happen..." he said, looking at the older woman's body. "Still though, I can't say I didn't enjoy it." said Tails, snuggling his head against her breasts.
"I see that you still have a habit of talking to yourself." said a familiar voice.
The young fox looked up to see that Vanilla was awake. "Ah, V-Vanilla! Um, y-you're awake?!" Tails stammered.
The rabbit MILF giggled. "Yeah, I've been awake for a little bit now." she started rubbing her hand up and down his back. "I've just been enjoying snuggling with a certain little fox. You do look rather cute when you're sleeping Tails." said Vanilla, scratching behind his ear.
Tails blushed a little upon hearing her response. Though in his mind, he was still processing what had happened. Not only did he have sex with Cream's mom, but he went as far as to cumming inside her, possibly knocking her up. Oh, who was he kidding? The possibility of her falling pregnant was second to none. Fertility was rather rampant in the Prower family.
Tails looked up into Vanilla's eyes. "Um Vanilla... d-do you think what we did back there was a good idea? I mean, you know... wanting me to get you pregnant and whatnot..." asked the young fox.
Vanilla smiled and held him more tightly. "A good idea? Perhaps not. Something that I wanted? Yes! Like I told you Tails, us rabbits don't have a strong sexual desire just for pleasure. No, we have it so that we can produce as many offspring as possible. Have as much sex with me as you'd like, I'd never be satisfied until I fell pregnant. That's just our biology." said the rabbit MILF.
"I-I mean I'm glad to help, but I don't know... I'm kinda unsure about this... I mean, even if no one discovers that I'm the father, or I'm not obligated to help raise it... It's still going to be my child at the end of the day." Tails responded.
Vanilla then rolled them over so that she laid on top of him. "Well, if you wanted to, perhaps you and I could be a couple. Then we could both raise the child together, hmm?" she asked, winking at him.
Tails was rather shocked by Vanilla's suggestion. Was she seriously suggesting that they should be a couple? While Vanilla was a nice woman, she was clearly too old for him. While yes, he had sex with with her, being in a relationship with her was a different topic all together. Like, what would people think if they saw the two of them dating in public? And what about his mother? Rosemary would never be okay with Tails dating a woman almost as old as she was. Heck, if she found out that he got Vanilla pregnant, that would be enough to sign his death warrent.
"Um, sorry Vanilla. Listen, you're a very nice woman, but I don't think I'm interested in having a relationship with you, sorry." Tails said, almost begrudgingly.
Vanilla shrugged her shoulders. "A woman can try, can't she?" she looked back down at him. "Don't worry Tails, I understand. And don't worry about everything else. Just like I promised, no one will find out that you're the father and you don't have to worry about taking care of it. That's fine by me." said the rabbit mother, giving him a kiss.
"Well, thanks for understanding, Vanilla. And if you're okay with all that, then I accept." Tails said happily.
"And I'm fine with it. Just don't forget what you promised me." said Vanilla, giving him a sly smirk.
Tails laid there for a moment, wondering what she meant. What again was it that he promised her? Everything that had happened earlier today was a blur. If he promised something, he had completely forgotten what that something was. He tried his hardest to remember. Though, no matter how much he tried, he just couldn't remember.
"Um... wh-what again did I promise you?" Tails asked in a confused tone.
"Remember, Tails, you promised me that you'd give me the same treatment that you've been giving Bernadette. You know, stopping by every once in a while to pleasure me for a little bit?" said Vanilla, smirking down at the young fox.
Tails felt rather dumb for forgetting about that. "O-Oh yeah, th-that. Of course, V-Vanilla." he said, scratching his head.
"Well then, I look forward to having you in my bed more often." she said, giving him a quick kiss on the lips.
Tails returned the kiss. "N-No problem, Vanilla." he said, looking up at the rabbit MILF.
"So Tails, what do you say we have another round?" asked Vanilla, winking at him.
Tails really wanted to say yes, but knew that he had to meet with Bernadette soon and couldn't waste anymore sexual energy on Vanilla. "S-Sorry, Vanilla, but I have to be going." he said hesitantly, looking up at her hot body.
"Aawwww, that's a shame... but, I understand." said Vanilla, crawling off of his body. "But, before you leave, take these." said the rabbit MILF, handing the young fox her crimson red panties.
Tails blushed as he grabbed them out of her hands. "V-Vanilla?..." was all that he could say.
"A little gift from me to say 'thank you', Tails. Please take them, keep them." she said with a smile.
Tails could still smell Vanilla's strong sexual scent on the crimson red panties. He was a little hesitate to take them, but figured that he'd best not argue. It seemed that from here on out, he was going to have to satisfy two sex deprived MILFs. But, little did he know, this was only the beginning. He was completely oblivious to just how many of his friend's mothers seeked the same thing. But, he would soon find out as his adventure continued.
"W-Well, I guess I must head out now." said Tails, scratching the back of his head.
Vanilla gave him yet another kiss on the lips. "Well, I look forward to seeing you next time, Tails." she said, smiling at him.
"Um, s-same..." said Tails, crawling off the bed and opening her bedroom door.
The two tailed fox exited Vanilla's room and slowly shut the door... only to be suddenly hugged by Cream the Rabbit. "Oh, thank you, Tails! Thank you, thank you, thank you for helping my mommy!" Cream shouted happily.
"Chao chao!" said Cheese, holding onto his ear.
"I-It was no problem, Cream." Tails said nervously.
"So, is my mommy feeling better?" asked Cream, letting go of her fox friend.
"Y-Yeah, she seems a lot better... though she did also ask if I could come back and help a few more times." Tails said with a blush.
"Well, I'm glad you're going to continue to help my mommy. You're a really good friend, Tails." said Cream with a smile.
"Chao chao chao!" said Cheese happily.
"Oh Tails, I..." Cream began to say, before pinching her nose. "Tails, you stink." she said.
"Chao chao..." said Cheese, doing the same.
Tails sniffed himself, smelling the sexual musky smell from him and Vanilla's Intercourse. "Um... mind if I use your shower?" asked Tails, wanting to wash himself before getting home, just in case his mother was there and could smell the evidence of his deeds.
"Sure Tails, go right ahead." said Cream.
"Th-Thanks..." said Tails, walking into the guest bathroom.
While Tails went off to take his shower, Cream walked inside of her mother's room and saw her resting in her bed. "So, did it work, mommy?" asked Cream.
"Mmmmm, it did Cream dear, it did..." said Vanilla, feeling all relaxed.
"Sooooo... I couldn't help but overhear... that Tails might have made you a mommy again?" asked the young rabbit.
"Oh, you were listening in? Well, I don't want to get your hopes up, but yes, there's a strong possibility that you're going to be a big sister soon." said Vanilla with a smile.
Cream jumped for joy and started dancing around. "I'm gonna be a big sister! I'm gonna be a big sister! I'm gonna be a big sister!" she said continuing to dance around happily.
Back at Castle Acorn, Max and Jules were still talking. The king sat there in his wheelchair, lookingat the robotic hedgehog with a confused look on his face. Jules went into detail about everything. From using his frozen seed to get Bernadette pregnant, finding out that Tails was into older women, convincing Tails to have sex with his wife, everything. Max could hardly believe that someone as innocent as Tails could possibly be a "MILF Man". Even more so, banging his best friend's mother...
"And that's basically everything that happened." said Jules, finishing his story.
"So let me get this straight... you got Tails to have sex with your wife?" asked Max, still in disbelief.
"Yes, that is correct. Fixed Bernadette's issue completely." replied the robotisized hedgehog.
"And now, you're telling me that I should do the same thing? You seriously want me to ask Tails to bang my wife?!" replied the old king.
"Well, if it fixed Bernadette's issue, then it should fix Alicia's issue as well. Plus, you're the king. Even if he says he doesn't want to, you could simply order him to do so." Jules replied.
"I don't think you understand how absurd this sounds! Besides, I'm not sure I feel comfortable having another guy screw my wife..." Max said with a sigh.
Jules could see the doubt in Maximillion's eyes. Walking over to the wheelchair bound king, the robotic hedgehog placed a hand on his shoulder. "You know, I had similar doubts about it. Despite those doubts, I went ahead and asked Tails to do it. In the end, Bernadette is now happier than ever. Plus, this isn't some random stranger doing it, this is Tails that we're talking about. One of the nicest and most reliable guys I know. Not only do I trust him with my wife, I trust him with your wife as well." Jules said, retracting his hand from the kings shoulder.
King Max thought for a moment. He knew that since Jules was robotisized, there was no way he could satisfy his wife's sexual needs. Now, he was in a similar position, due to his erectile disfunction. If Tails really satisfied Bernadette like Jules said, perhaps the two tailed fox boy could do the same for Alicia. Even though he was still rather hesitant about it, he knew that it was perhaps necessary to satisfy his wife's lust. As much as he hated to admit it, he was going to need someone to pleasure his wife for him. And like Jules said, Tails was both nice and trustworthy. So, it would probably be best to have him do it, rather than anyone else.
"I... I guess you're right..." Max finally admitted...
"Yeah, though I guess Tails might need to wear a condom, before he has sex with your wife. I mean, Bernadette was already pregnant from my sperm that I had frozen, so I didn't have to worry about Tails getting her pregnant. Alicia on the other hand..." Jules said, scratching his metal head.
"Actually... that won't be necessary. You see, Alicia went through menopause last year... she is no longer fertile and is incapable of getting pregnant..." Max admitted, slightly embarrassed about telling someone something so personal about his wife.
"Oh, well then, that makes things even better for the young fox." said Jules with a robotic chuckle.
"Yeah, and besides, I'm pretty sure Alicia will prefer to do it bareback as well. Ah, I guess I'm really about to let this happen..." the old king said with a sigh.
"Look, I know that you're still uneasy about this wholething, but you've gotta trust me." the robotisized hedgehog gave the old man a pat on the back, then started to walk back into the castle. "Anyways, I have to be off now. Give it some thought, okay." said Jules, walking away.
Max sighed. "Sure thing Jules, thank you..." he replied.
The old man sat there in his wheelchair, thinking to himself. The king knew that there was no other way to fix Alicia's problem. Jules giving him this information, was definitely a gods sent. Maximillion, still in deep thought, began to wheel his way back into the castle. Eventually, he found his way back into the royal bedroom, where he found his wife laying on the bed reading a book. Or rather, trying to, due to her trying to suppress her sexual urges.
"Oh, you're back." said Alicia, turning a page in her book, her hands slightly twitchy.
"Yeah, um... listen Alicia... about your issue..." Max began to say.
"I already told you Max, it's not your fault. You don't have to dread upon it." the queen said, cutting him off mid sentence.
"W-Well, the thing is Alicia, I think I found the solution to your problem..." the king replied...
As Tails walked home, the young fox had a lot on his mind. First of all, he was banging his best friend's mother. Satisfying Bernadette was already enough of a risk, considering what would happen if Sonic or Rosemary found out. Now on top of that, he promised to do the same with Vanilla. Not to mention, he most likely got her pregnant for crying out loud! Little did he know however, things were about to get even more spicy as time went on.
Upon arriving at home, he found that both of his parents were still at work. He breathed a quick sigh of relief before walking inside. Once inside, he went to his bedroom, still deep in thought. Sitting down on his bed, he looked at the panties that Vanilla gave him. The fabric still smelled of the MILF's sexual musk. Even with all the chaos that would come from him being found out, he couldn't deny that he loved every second of his time with Bernadette and Vanilla.
Getting up off of his bed, he walked over to his dresser. "I guess I'll put these in here." Tails said to himself, opening his sock drawer and placing Vanilla's panties under his socks, before shutting the drawer back.
Now that that was done with, he had to be on his way. He had to meet up with Bernadette soon for, well... you know what. Just as he was about to head out, he heard a sudden knock on the door. The fox boy's ears twitched at the sudden noise, wondering who it could be. It was way too early for his parents to get off work. Leaving his room, he walked over to the front door, just as he heard another knock upon the door.
Opening the door, it was revealed to be Sally Acorn. "Hey there, Tails. How're you today?" Sally greeted.
Tails smiled at her. "Oh, hello Sally, I'm fine today. What brings you here?" the two tailed fox asked.
"Well, my father currently is requesting your presence." Sally replied.
"Your father? Did he say why?" Tails asked.
"No, he didn't. But king and country and what not. If my father has requested your presence, it must be important."
Tails pondered for a moment. He was supposed to head on over to the Hedgehog residence in a bit so that he and Bernadette could... well, you know... But, like Sally said, king and country. Heck, if he was indeed requesting his presence, then it must be urgent. Eggman may be up to something. Not only that, but always being in Sonic's shadow, the young fox was always excited when someone needed his help specifically.
"Okay Sally, I'll head on over to Castle Acorn as soon as I can. Just um... give me a couple of minutes, okay..." said Tails.
"Sure thing, Tails. Just be quick about it. My father isn't exactly the most patient man, as I'm sure you know." the princess then turned around and began to walk away. "Anyways, that's all I needed to tell you. I best be heading off now. Later Tails." she said, waving to him as she walked off.
"Alright Sally, later." he replied, slowly shutting the door.
Oh great, now he was going to have to cancel his little visit with Bernadette. Granted, Vanilla had already more than satisfied his sexual cravings for the day. Though, he was less worried about satisfying himself and more worried about satisfying her. Canceling their little sex session, well... hopefully she'll understand. Taking out his phone, he scrolled down to Bernadette's name and hit "Call". The two of them had always contacted each other through calls rather than texts, this way Sonic could never stumble upon any evidence.
The phone rang for a bit, until the hedgehog MILF answered. "Oh, hello there sweetie. I was just getting ready for your company. Mmm, I can't wait either, I'm extra horny today." Bernadette said, purring into the phone.
'Oh man, I hope she takes this well.' he thought to himself. "Um, B-Bernadette... about that..." he said, trying to find the right words to say.
"Mmm, I've got something special for you too. I bought a whole can of cool whip from the store." Tails could hear the sound of cool whip being sprayed. "I'm already naked and covered in cool whip. Mmmm, I want that fox tongue of yours tasting every part of my body." said the horny MILF.
'Good grief, she is NOT making this easy!' Tails cleared his throat. "Yeah, um... you see, the thing is..." he began to say, before she interupted him.
"I left the front door unlocked, so don't even bother knocking today. Just walk right on inside. Heh, maybe after you get a good taste of my body, I can spray some cool whip on you. I can't wait to have a good taste of yah." the motherly hedgehog said, continuing to talk away.
Tails started to slowly form an erection from Bernadette's description. 'King and country, king and country!' He kept saying in his head, trying not to fold on his duties and give into his horny mind. "B-Bernadette... I'm not going to be able to come over today!" Tails suddenly blurted out.
"And then after that we can... wait... what do you mean you're not able to come over?!" the hedgehog MILF responded, not necessarily angrily, but more so annoyed.
"Well, you see... something kinda, came up..." the fox boy responded, knowing just how disappointed she probably was.
"Tails, you could have told me this like ten minutes ago... I'm literally laying on my bed right now, naked and covered in cool whip. Not to mention, extremely horny!" Bernadette said, still a little agitated.
"Look, I'm sorry okay. I promise I'll make it up to you, but I've been told to go to Castle Acorn. Apparently the king himself is requesting my presence. It might be really important." he said.
Tails could hear the hedgehog woman sigh. "Fine, but the next time you come over, I want two rounds to make up for this lost one." she responded, still annoyed but rather understanding.
Tails chuckled at the hedgehog woman's response. "Okay, that sounds fair." he responded.
"Okay, well I guess I'm going to go wash this cool whip off of me. Take care, Tails." said Bernadette.
"Okay, take care, Bernadette." said Tails, before they both hung up. "Okay, now I better hurry and get to Castle Acorn. If the king needs to see me, it must be urgent." He said, walking out his front door.
At castle Acorn, Rosemary Prower and Isabella Mongoose were doing paperwork, both currently wearing their Acorn Council uniforms. Both women however, were distracted, but by different things. Rosemary's motherly intuition was still skeptical of Tails. She knew something was up with her son and she was going to get to the bottom of it. Isabella on the other hand, had a completely different issue. As the mongoose woman tried to do her paperwork, she was fidgeting in her seat.
"Isabella, if you have to go to the restroom, then go." said Rosemary, not looking up from her paperwork.
"That... That's not the problem." said Isabella, still fidgeting and wiggling around in her seat.
"Hm, then what is the problem?" asked Rosemary, looking up at her co-worker.
"Rose, w-we're both women here. S-So I think I can tell you... I'm currently suffering from some, um... lack of sexual satisfaction..." said the mongoose woman, as a blush appeared on her face.
Rosemary's eyes shot open upon hearing that. "Lack of sexual satisfaction?" the fox woman asked, rather surprised.
"Y-Yeah, I've just been sexually deprived for so long and it's driving me crazy! I have trouble sleeping at night, concentrating during the day, heck, I can barely focus on this paperwork right now!" said Isabella, continuing to fidget in her seat.
'I can't believe I am having this conversation right now...' Rosemary thought to herself. "Is this really the kind of conversation you should have with your co-worker?" she asked.
"P-Probably not, but it's driving me insane! I just can't do my work effectively." replied Isabella.
"Can't you just, well you know, use some tools?" asked the fox woman, looking back down at her paperwork.
"If you mean dildos and vibraters, then I've already tried! It's just not the same as the real thing, you know?" the mongoose woman the sighed. "If only Arthur was still with me..." she said somberly.
Rosemary then felt her heart skip a beat, as she was reminded on Isabella's deceased husband. "Well Isabella, perhaps you could find another guy." she said, looking over at her co-worker.
"No, no, no, I can't! I promised myself upon Arthur's death that he'd forever be the only man I'd love. I can't be in a relationship with another guy!" said Isabella, flipping out a little.
"Who said anything about a relationship?" retorted Rosemary.
"Huh?!" the mongoose woman asked.
"What I'm suggesting, is that you simply get a guy to satisfy those sexual needs of yours. No relationship, no love, just sex." said the fox woman.
The mongoose mother thought for a moment upon what Rosemary said. "I-I guess... it's not like I have any other options. B-But who?!" Isabella asked.
The fox mother then stood up and collected all of the paperwork upon her desk. "I don't know, but make sure it's a guy you can trust. Someone that you'd know would be safe, preferably someone you already know well." walking to the door, she looked back at her co-worker. "Anyway, I've gotta take this paperwork to the front office. I hope everything works out for you." said Rosemary, before leaving.
"Th-Thanks, Rosemary." replied Isabella, continuing to fidget in her seat. 'Someone that would be safe? Someone that I already know well?' she thought to herself.
Rosemary walked down the halls of Castle Acorn, readjusting the stack of papers in her hands. As the fox woman was walking, she thought about her case with Tails. Her mother's intuition was bugging herconstantly. She knew something was up with her son and she was going to get to the bottom of it. What ever that something was. She then lowered the stack of papers and immediately saw none other than her own son, Miles "Tails" Prower, walking down the hall in the opposite direction.
"Miles?" Rosemary blurted out upon seeing him.
"Wha... oh, h-hey mom." Tails responded, as she slightly surprised him.
"Um, what are you doing here, Miles?" asked the motherly fox.
"Oh um, Sally told me that her father needs to see me." the two tailed fox responded.
"King Max needs to see you? Well, then it must be important." she said, smiling down at her son, proud of the fact that the king himself needs him.
"Yeah, it might be, but I won't kow until I speak to him." said Tails.
"Well then, I won't keep him waiting then." said Rosemary, stepping out of his way.
"Thanks, mom. I'll see you later. Love yah!" said Tails, walking in the direction of the throne room.
"Alright, take care now, Miles. Love you!" said Rosemary, walking towards the front office. 'Perhaps I shouldn't be too worried about him. He's such a good kid. Still though, my mother's tuition has yet to be wrong.' she thought to herself.
As Tails walked away from his mother, he approached the throne room. It appeared that the guards had been told of his arrival ahead of time, as they let him past without saying a word. Tails then saw Maximillion himself, sitting upon his throne. There appeared to be no one else present, no Sally, no Elias, no Megan, not even Alicia, the queen herself. Tails then approached the king and got down in a bowing position. To which, Max stopped him as he did so.
"Don't worry about being so formal, Mr. Prower." said Max.
"Oh, um ah, s-sorry your majesty." replied Tails.
"And don't worry about calling me 'majesty'. Just Max will do fine." said the king.
"Oh, o-of course, Max." replied the nervous foxboy.
"Good, now that that's out of the way, I need to ask something of you. Something that I can trust you and only you with." said Max in a very serious tone.
'Me and only me? Oh, this must be important and the king himself trusts me over anyone else. I must really be moving up! I wonder what it is?!' the young fox thought to himself. "What is it that you need, King Max?" asked Tails.
"Well... how do I put this... It's less so that I need your help... but, more so my wife, Alicia that needs your help..." the king stuttered, trying to find the right words to say.
"Um... Queen Alicia needs my help? Um, with what?" asked the young fox.
"Well Tails, it has come to my attention... that you helped Jules' wife, Bernadette, with a... similar problem that my wife is currently having..." said Max, trying not to be too blunt.
Tails' eyes immediately shot open. 'W-Wait, he's not talking about... THAT, is he?! How could he possibly know about him and Bernadette?!' the two tailed fox thought to himself, panicking immensely. "A-And what would that problem b-be?" Tails asked nervously.
"Look Mr. Prower, there's no easy way for me to ask this, so I'm going to just come out and say it. I know that you had sex with Bernadette to satisfy her sexual desires, at Jules' request." said the king.
Tails felt his heart beat rapidly upon hearing that. "Wh-What?!... H-How did you find out about that?!" asked the panicked fox.
"Because I told him." said a familiar robotic voice.
Tails turned around, only to see none other than Jules Hedgehog, walking towards him. "Y-You WHAT?!" he said, continuing to freak out.
"That's right, Mr. Prower. Jules told me everything." said Max.
"B-But WHY?!" Tails asked, looking over at the robotic hedgehog.
"Simple really. You see, Max and I were having a little discussion and he brought up the fact that Alicia was currently having... some sexual issues..." Jules began to say.
"It was then, that he brought up the fact that Bernadette was having the same issues days ago." said the king.
"I then brought up my solution. AKA, you! I told him all about how you helped satisfy my wife's sexual urges and have been continuing to do so." said the robotic hedgehog.
"And then he suggested that I get you to do the same. After a bit of hesitation from myself, I soon realized that I didn't have another option. You see Mr. Prower, I am quite old. Because of this, I am currently suffering from erectile disfunction and am unable to get it up. Because of this, I am incapable of satisfying my wife." said Max.
"So, it's quite simple. King Max needs you to satisfy Queen Alicia the same way you helped me satisfy my wife, Bernadette." said Jules.
"Well Mr. Prower, what do you say? Will you help me satisfy my wife?" asked King Max.
Tails was dumbfounded upon hearing this request. Here was the king of the Acorn Kingdom... asking him to have sex with his wife, the queen of the Acorn Kingdom! Tails was just being a generous guy when he accepted to help Bernadette satisfy her sexual desires. But, he never would have thought it would lead to him having sex with Vanilla as well! Now here he was, being asked to have sex with yet another one of his friend's mothers! Sally Acorn's mom, Alicia Acorn!
"I-I don't kn-know about this..." said Tails, rather nervously.
"Listen Tails, I was trying to be formal at first, but now I must be stern! I wanted to ask nicely at first, but if you don't want to do this, then I will order you to do so!" Max said rather firmly.
Tails sighed, knowing that what the king said goes and that he couldn't say no. "W-Well then... I-I guess I'll help, then..." said the two tailed fox.
"You guess?!" the king retorted.
"I-I mean... I will help, then!" the young fox corrected himself.
"Good! Now, Alicia is currently in the royal chambers. Jules will walk you there." said Max, as Jules now stood directly next to Tails.
"W-Wait, I-I don't have any protection on me!" said Tails, suddenly remembering the fact that he most likely got Vanilla pregnant this morning.
Max chuckled. "No need to worry, Mr. Prower. Alicia is much older than Bernadette and with age comes a loss of other things. She's already gone through menopause and is incapable of getting pregnant. You have nothing to worry about." said the king.
Tails gave a quick sigh of relief. "W-Well I guess there's nothing to worry about..." he said nervously.
"Now, if you'll follow me, Tails." said Jules, as he began to walk to the throne room's exit.
Tails followed and the two of them left, walking down the castle hallway. "Why did you tell him about me and Bernadette?!" Tails shouted, as he was a tad bit angry at the robotic hedgehog.
"My apologies, Tails. It's just that when he told me the kind of problems Alicia was having, I knew that I was once in the same situation with my wife. I knew that you could help Max the same way you helped me. Besides, I already know that you like older women." said Jules.
Tails blushed. "Ye-Yeah, I am into... older women... but I was already diving into uncharted waters when I had sex with my best friend's mother. Now I have to do the same with Sally's mom?!" Tails shouted.
"Look, I'm sorry that I set you up with this, but I know that you're someone that can't stand to no not help someone when they need help. Well, I'm the same way." said the robotic hedgehog.
"I-I see... well, I guess that as long as I'm helping someone... I-I guess it'll be fine..." said the two tailed fox, still nervous.
They both eventually reached the royal bedroom and Jules knocked on the door three times. "C-Coming..." said a familiar female voice that sounded rather nervous. The door soon opened, revealing Alicia Acorn, wearing her usual orange dress. "Oh, h-hello there, Tails." said the queen rather nervously.
"H-Hello there y-your majesty." Tails said with a big blush on his face.
"I-I'm sure Jules and my husband filled you in on everything? Th-Thanks for your help..." she said, nervously rubbing her arm.
"Y-Yeah... I-I understand the situation..." he replied, surprised to see how nervous she was.
"Have fun you two." said Jules, walking away, causing the fox and chipmunk to blush simultaneously.
"P-Please come in, Tails." said Alicia, opening the door wider.
"O-Of course, your majesty." said Tails, stepping in.
"Oh, d-don't worry about calling me that, Tails. Alicia will do fine." she said, shutting the door behind him.
"Oh, um... s-sure thing Alicia." he replied.
"So um, Max doesn't want us to do it in our bed. So, I ran us a bath in the royal bathroom. We'll be doing our 'business' in there." Alicia said, nervously rubbing her arm again.
"Oh, well I g-guess I can understand that. Um, l-lead the way." said Tails
Alicia nodded, then walked towards the royal bathroom. Tails followed the older woman who seemed to be about as tall as Bernadette and Vanilla, as his head was leveled with her stomach just like with them. They both entered the bathroom and Tails was taken aback by the size of the tub. It was big enough to be a small pool for crying out loud. Not to mention, it looked as if Alicia took the time to light some candles. A whiff of a cinnamon like smell entered Tails' nostrils, most likely from the candles.
"S-So I um... I guess I should take off my clothes now?..." Alicia said with a blush.
Tails at this point was surprised by just how nervous she was, probably even more nervous than he was. "Alicia, you seem k-kinda nervous." said Tails, as both Bernadette and Vanilla weren't quite like this.
"W-Well, to tell you the truth Tails... I am quite nervous. M-My husband is the only man I have ever revealed my body to. I was a virgin before we married and we didn't have sex until we were married. For thirty years I've only been intimate with him." she said, blushing harder.
"I-I see... well, if you don't want to do this..." he began to say, before being interrupted.
"NO!" she suddenly blurted out. "I-I may be nervous, b-but I know I need this!" said the queen, undoing the buttons on her dress.
"I-If you say so..." said Tails, watching her.
Once she had successfully unbuttoned her dress, she swallowed a big lump in her throat. Closing her eyes, she let the dress fall to the ground. Under her royal dress, she wore a white corset-top, white panties and white stockings. Alicia then tried to hide her body out of embarrassment, wrapping her arms around her MILF body. Tails could tell just how nervous she really was, definitely more than he was. Bernadette and Vanilla took charge before, due to his nervousness, but with Alicia, it seemed as if he was going to have to be the one to take charge.
"A-Alicia, it's okay. If we're going to do this, then you can't be afraid to show off your body." said Tails, reassuringly.
"He made you do it, didn't he?" asked Alicia, catching Tails off guard.
"Wh-What... what do you mean?" asked Tails.
"The only reason you're here, is because Max forced you to, isn't it?" she asked, as Rails just stood their in silence. "As I thought, why else would you wanna have sex with an old lady like me." said the queen, rather somberly.
"Woah, h-hold on now. You're not THAT old. Besides..." Tails said, walking up to her, removing her hands from her body and holding them in his own. "Yes, it's true that he ordered me to do this, but that doesn't mean that I don't want to help you. Your age doesn't bother me, just like it didn't with Bernadette." he said, continuing to hold her hands.
"Yes, Bernadette, the woman who is ten years younger than me... and can still get pregnant..." said Alicia, with a slightly somber tone.
"Alicia, is that what this melancholy tone is all about? Y-Your menopause?" said the two tailed fox, understanding her tone now.
"So, my husband mentioned that too? So yes, I'm nothing but an old lady now. I can't get pregnant anymore and I can't have children..." she said, drooping her head down.
"Like I said before, you're not THAT old. Besides, you may be ten years older than Bernadette, but you look the same age as her." he said, reassuring her, not to mention, nort lying to her either, as she clearly was royalty and took good care of herself though the years.
"Tails, you don't have to say these things, j-just to try and make me feel be..." Alicia began to say, only for him to cut her off mid sentence.
"I'm not saying this to try and make you feel better, Alicia. I'm saying it because I mean every word. Not only have you aged gracefully and look ten years younger than your current age, but you're also a beautiful woman." he then ran his hands down her body. "With an equally beautiful body. A body that I would like to see more of." said Tails, running his hands down her body.
"Tails..." said Alicia, looking down at him with a surprised look on her face.
At first, she couldn't believe what she was hearing. But, when she looked into the young fox's eyes, she could see just how honest he was. Alicia soon found her head tilting forward, as her lips soon met his. Tails was surprised at first, but happily held onto her cheeks and kissed back. Alicia was the next one to feel surprised, as Tails inserted his tongue into her mouth. Alicia always being royalty, always kissed her husband modestly, so she was rather surprised by something like this.
Despite her surprise, Alicia got slightly turned on by Tails' tongue exploring the inside of her mouth. Curiously, she slipped her tongue into his mouth as well. She soon felt the kiss get even more intense, as their tongues wrestled with one another. It was all so much more intense, more so than any kiss her and Max ever shared. Their lips soon parted, as they both gasped for air. The pair then looked into one another's eyes, showing their attraction towards one another.
"T-Tails, that kiss with the tongue. I've never done that before." said Alicia, catching her breathe.
"I-I didn't know that." Tails replied, breathing heavily.
Alicia then blushed and turned around so that her back was facing him. "Tails, you wouldn't mind unzipping my corset for me, would you?" she asked, looking back at him, a big blush still on her face.
Tails blushed, then smiled. "N-No problem, Alicia." he said, stepping closer to her.
Due to their height differences, Tails had to stand on his tippy-toes just so that he could reach the zipper at the top of her white corset-top. Because she was royalty, it would only make sense that she'd wear a corset, rather than a bra. Upon grabbing the zipper, the young fox began to slide the zipper down the older chipmunk's back. Once he unzipped it, the white fabric fell to the floor, leaving Alicia's topless. The queen was still rather nervous, something that could definitely still tell. Due to this, when she turned around, she held her hands over her breasts, hiding them from the two tailed fox before her.
Tails reached his hands up and grabbed her wrists. "Now Alicia, you have nothing to hide." said Tails, pulling her hands away.
"H-Hold on, Tails, th-they aren't what they used to be." said Alicia, still afraid to show her body off to Tails.
Tails soon pulled her hands away, revealing the queen's slightly saggy, yet still nice breasts. "See Alicia, like I said. You're a beautiful woman with a beautiful body." he said, reaching his hands up to massage her boobs.
Alicia moaned and continued to blush. "Y-You're just saying that to make me feel better. You're lying, I know you are. They droop and sag now, unlike Bernadette's..." she said, feeling saddened once more.
Tails looked up at her with a concerned look on his face. He knew that before they could move forward, he had to find out what was truly wrong with Alicia. Not to mention, why did she keep on bringing up Bernadette? Tails then guided her hand over to the large bathtub and had her sit down. The queen's pantie covered butt sat upon the edge of the tub. Tails then held onto her hands and looked her in the eye.
"Alicia, what's the matter? Also, why do you keep on bringing up Bernadette?" Tails asked.
Alicia let out a saddened sigh. "Well, it's just that... ever since I've hit menopause and been told that I could no longer have kids... I've felt a little down about myself. To tell you the truth, I always wanted a third child. As both Sally and Elias grew older, I... I wanted to have that mother's experience once again. But both me and Max where always just so busy, then there were the constant threats to the Acorn Kingdom. We both knew we couldn't bring a child into something like that. But now, I can never have another child..." said Alicia with a somber tone.
"And the reason why you keep mentioning Bernadette?" he asked, rubbing her hands.
"Because... Because I know that she's pregnant... I know that she can still have children and I can't. She sounded so happy when she told me. I felt old, old and useless... and unattractive... Then the rest of my self confidence started to go downhill. To make matters worse, Max suddenly had erectile disfunction and could no longer satisfy me. Then I find out that you and Bernadette had sex and my husband was going to get you to do the same with me... your only here to give me pity sex..." said the queen, looking down.
Tails then cupped Alicia's chin. "Alicia, it may be true that your husband, but I assure you that I'm not here to give you pity sex. The reason that Jules got me to have sex with Bernadette in the first place, was because he found out that I was into MILFs. While I may have done it to help out, I can't deny that I enjoyed every bit of it. It's the same for you my queen. You are an attractive older woman. You are a MILF." said the two tailed fox with a smile.
"T-Tails...d-do you really think I'm a MILF?" she asked, feeling her confidence boost a little.
"I don't think, Alicia, I know." he said, kissing the older woman's lips.
Alicia could feel the genuineness of Tails' words, as he passionately kissed her lips. But, the fox certainly didn't stop there. He soon began to kiss down her cheek, her neck, her chest, before he finally reached her bare breasts. A small moan escaped the queen's mouth, as he began to suckle on her left breast, while massaging the other with his hand. He soon switched and began to suckle the other. She held the back of his head as he did so, seeing that he truly wanted to have her body, truly finding her attractive and Alicia wanted him too.
"Ah, Tails..." Alicia moaned, feeling his lips going lower.
He soon began to kiss down her body once more. The fox boy kissed down under her breasts, down her stomach, giving her pantie covered crotch a quick kiss, causing her to moan. Tails then undid her stocking strap and began to pull her the right stocking down, kissing along her leg as he did so. Once off, he did the same to her left, sliding it down her leg and leaving a trail of kisses behind it. He then took the rest of her white stockings off and tossed it to the side, right on top of her corset and dress. Tails then reached up and grabbed the hem of Alicia's white panties, then looked up at her.
"Go ahead, take it off me, Tails. I trust you to do so now, please." said Alicia, reassuring him.
"Of course, my queen." Tails responded, before looking back down at her crotch.
Tails began to slowly slide the white fabric down her legs. As he did so, her womanhood was soon revealed to him. The same vagina that had given birth to his close friend, Sally Acorn, was now in his view. Sliding the rest of the white fabric down, he tossed it next to her other cloths. The queen now sat before the fox, completely naked. But, he didn't stop there. Tilting his head forward, he began to kiss the outer lips of her most sacred regions.
"Oh... ah... T-Tails..." Alicia moaned, feeling his lips kiss her womanhood.
Tails didn't stop at kissing though, far from it. He had built up enough experience with oral sex from his time with Bernadette and he wasn't going to let that experience go to waste. Using his two thumbs, he spread her puss lips apart. Sticking out his tongue, he slipped it inside the queen's vagina. Alicia moaned loudly, never feeling anything like it before. Her and Max were always so traditional and old fashion, they never once did oral.
"Oh Tails, t-that feels so good! P-Please, don't stop!" Alicia moaned, enjoying every bit of it.
Tails didn't let up for even a second, circling his tongue inside of the MILF's pussy like a wild tornado. Alicia spread her legs further apart, gripping the bathtubs edge and moaning. She started to loose focus, feeling like melting butter. That loss of focus soon led to a loss of other things. Mainly... her balance. Alicia fell backwards into the bathtub, creating a big splash in the process.
"Alicia!" Tails shouted, hoping she didn't hurt herself.
The young fox was soon relieved when the queen resurfaced, wiping her eyes. "Y-Yeah Tails, I'm fine." said Alicia, gasping for air, not cause of the fact she was just under water, but because of the pleasure Tails had just given her... and she wanted more.
It's a good thing the royal bathtub was big enough to be a small pool, otherwise the MILF before him would of bonked her head. "W-Well... since you're already in the tub, I suppose I should get in as well?" the two tailed fox asked.
"Oh... o-of course, Tails. Please, c-come join me." said the queen.
Tails was so used to having Bernadette take charge when they were together, that it made things feel off due to just how nervous Alicia seemed to be. The fox boy stood up, revealing that he currently had an erection. The royal MILF looked at his manhood with a blush, seeing just how full of energy it was. Not to nock her husband, but he was much older than her and even before the erectile disfunction it always looked... actually... let's not go into detail. This is supposed to be a spicy fanfic, so you probably don't wanna hear about an old man's genitalia. Tails then took off his shoes, socks and gloves, then stepped into the large bathtub.
"Ah, the water feels great." said Tails, sitting down in the tub, feeling what it was like to be royalty for a brief moment.
"S-So um... how're we g-going to you know?..." Alicia said with a blush upon her face.
Tails blushed in response, remembering that he was supposed to have sex with Sally's mom. "Um... lean your back against the edge of the tub." Tails said, scratching the back of his head.
Alicia nodded her head and complied, leaning her back against the edge of the tub. "L-Like this, Tails?" The queen asked.
"Y-Yeah, just like that." he said, scooting forward so that his smaller body was on top of her larger one.
Underwater, Alicia could feel his erection poking against her thigh. Tails tilted his head forward and kissed the queen once more. Alicia couldn't believe that she was about to have sex with a guy younger than her own children. Tails as well couldn't believe he was about to have sex with a woman older than his parents. Sure, Bernadette was slightly older than his mother, but his father was still older than her. This is something that should've sickened both the fox and chipmunk to no end. Instead, it turned them on even more.
"T-Tails... p-please, Tails. It's been so long." said Alicia, feeling his cock now rubbing against her womanhood.
"Of course, my queen." said Tails, taking hold of her waist.
Under the warm bathwater, he poked the tip of his length against her nether lips. Looking into her eyes, Tails began to slowly insert his penis inside of Alicia's waiting vagina. Both let out a soft moan, as the two tailed fox's length was engulfed by the queen's tight vaginal walls. After so long, she was finally filled. But, not by her husband. Instead, it was her daughter's friend who would enter her most private regions.
"Ah, Tails!" Alicia moaned, feeling him stretching her inner walls.
"Oh, Alicia!" moaned Tails, feeling the tightness of her inner walls clamp down upon his length, showing just how long it's truly been for her and how sex deprived she really was.
Tails soon tilted his hips back, then trusted forward, causing the bathwater to splash. He kept on thrusting, keeping up a steady rhythm. Alicia wrapped her arms around his neck and her legs around his waist. The water splashed harder, as he soon increased his speed. Some of the cinnamon scented candles were even extinguished, as water splashed upon them. The young fox soon began to pleasure her breasts with his mouth, causing Alicia to tilt her head back in pleasure.
"Ah, Tails! It feels incredible! Oh, it's been way too long!" Alicia moaned.
Each thrust caused the head of his penis to make contact with her cervix, creating a suction cup noise, due to the bathwater within her vaginal walls. Both could soon feel their limits approaching, knowing that they couldn't last much longer. Alicia's inner walls clamped down on his length even tighter, as they both couldn't hold back any longer. Simultaneously, they both hit their orgazms. Alicia coated Tails' cock with her infertile juices, as Tails filled her womb with his fertile seed. A small part of Alicia wished that she was still fertile, just so the young fox could knock her up and give her another child. But alas, it could never happen.
"Aaashhhh!" Alicia moaned, as her orgazm subsided and Tails continued to fill her womb.
Eventually, Tails pulled out, allowing their mixed juices to be washed away in the bath water. "So, did that satisfy you, my queen?" Tails asked, smiling at the royal MILF.
Alicia responded not with words, but with a kiss upon his lips. "Yes Tails, I feel soooo much better." she said, rubbing the back of his head.
"Well, I'm glad I could help." he said, stroking her cheek.
"So Tails, I was also told that after you and Bernadette had sex, you continued to help satisfy her needs for the past week and will continue to do so. I was just wondering. C-Could you do the same for me? I'd love to have you come by often and we could... *giggles* have some more fun together." asked the queen, blushing in the process.
Tails was hesitant to say 'yes', due to the fact that he'd already made the same promise with both Bernadette and Vanilla, but he just couldn't say 'no' to that blushing face of hers. "Of course, Alucia. If that's what you'd like, then I'd be happy to continue to help." said the two tailed fox.
"Oh, thank you, Tails!" said Alicia, kissing his lips with passion.
"No problem, Alicia. But for now, I must go. If I stay here any longer, my mother will start asking questions." said Tails, scratching the back of his head.
"Oh, then I guess you better get going then. I think I'll stay and relax in this tub a tad bit longer." she said with a smile.
"Okay, I guess I'll see you around then." he said, getting out of the tub.
Once out, Tails grabbed one of the spare towels off the rack and used it to dry himself off. Once done, he threw it in the hamper and put his socks, shoes and gloves back on. Taking one last look at Alicia's nude MILF body, he exited the royal bathroom and entered the royal bedroom. Opening the bedroom door, he was greeted by King Max, who sat at the door in his wheelchair, as if he'd been waiting there. This of course startled the young fox.
"Aaahhhh!" Tails shouted in surprise, jumping backwards.
"I asume that things went well?" asked Max, as if everything was normal.
"Y-Yeah... I did... well, you know..." the two tailed fox said, still a little startled.
"Thank you, Tails. You don't know how much of a life saver you are." said the king, giving him a firm handshake.
"Heh, n-no problem." said Tails, returning the handshake.
"Well, I suppose you best be off now. I must now tend to my wife. See you around, Tails." said Max.
"Yes sir!" said Tails, before walking away.
Once the young fox had left, Max wheeled his way through the royal bedroom and into the bathroom. Once inside, he saw his wife laying peacefully in the tub. Alicia seemed rather relaxed, having her eyes closed and resting her head on the edge of the tub. It seemed that Tails did a good job. He then wheeled closer to his resting wife.
"So, how was it?" asked Max.
"Absolutely perfect..." replied Alicia.
Tails walked down the halls of Castle Acorn, still in disbelief. First he had sex with Sonic's mom, Bernadette. Then of course that led to him having sex with Cream's mother, Vanilla. Now finally, he just had sex with Sally's mom, Alicia. Not only that, but now all three of them desired constant sexual attention from him, something that he agreed to give them. He didn't know what kind of hole he'd dug himself into, but that hole was about to get even deeper.
"What have I gotten myself into?" Tails asked himself, walking towards the castle entrance.
As he walked towards the exit of the castle, he walked right by Isabella Mongoose, the mother of his friend, Mina Mongoose. She had just finished her stack of paperwork and was taking it to the front office. Due to her sexual deprivation issues, she took much longer to finish her work than Rosemary. Once she submitted it at the office, she received a scolding for taking so long to finish. Once she left the office, she too walked towards the exit of the castle. As she did, she continued to think about what Rosemary had told her.
"Someone that would be safe? Someone that I already know well?" said Isabella to herself, as she walked right past Tails and the two of them walked home in opposite directions.
Isabella eventually reached her house and opened the front door. The first thing that she saw, was her daughter, Mina, sitting on the couch with her boyfriend, Ash. They seemed to be watching something on the television. They then turned to look at her as she entered the house, shutting the door behind her.
"Oh, mom, you're back from work?" asked Mina.
"How was work, Mrs. Mongoose?" asked Ash.
"It was... well... actually Ash, could I have a talk with Mina... alone?" asked Isabella, looking at Ash.
"Oh... no problem, I best be going anyway." said Ash, giving Mina a kiss. "I'll see you later, okay." he said, getting up to leave.
"Okay, bye hun." said Mina, as her boyfriend left. Once he was gone she turned to look at her mother. "Same problem?" she asked her mother.
"Yes Mina, same problem and I don't know how much more of it I can take! It's driving me insane! I-I can't even concentrate on my work!" said Isabella, sitting on the couch next to her daughter.
"Well, how's your search for a guy going?" asked Mina.
Isabella sighed. "Not too well. No one could ever replace your father, no one... so... I've decided to stop looking for a guy to remarry." said the motherly mongoose.
"Well... then how are you going to satisfy your... urges?" asked Mina.
"Well, my co-worker, Rosemary... she suggested that I should just find a guy to help me satisfy those sexual urges of mine and just not be romantically involved with that person. Someone that would be safe. Someone that I already know well." said Isabella.
"Oh, do you have a guy in mind?" asked Mina.
"Well... I was hoping that you'd be okay... with me and Ash..." the mother mongoose began to say, only to be cut off by her daughter.
"NO! ABSOLUTELY NOT! Mom, you are not going to have sex with my boyfriend!" shouted Mina.
"B-But I don't know who else and I can't take it anymore!" said Isabella.
Mina sighed. "Listen mom... I want to help you, but I'm not okay with letting you have sex with my boyfriend. How about... instead... I help you find someone..." said Mina, looking at her mother.
