In a hotel bedroom on the outskirts of Central City sat two teenagers.

Tails and Cream were waiting for the latter's mother. It had been about 15 minutes now, and both were starting to get a little anxious. After all, they were about to have a... unique lesson.

"Nervous?" Cream said, finally breaking the silence between them.

"A little, if I'm honest." Tails replied. "But, I'm also a bit excited."

Cream giggled. "Aw, Tails! I didn't realize you had a naughty side!"

"T-That's not what I meant..." Tails stuttered slightly. "It's just... I'm used to knowing about machines and technology and all that. But this? This is something completely new. I'm really curious to know how this is going to work."

"That makes sense." Cream said with a nod. "But... We both have a rough idea about what we have to do. Are you sure you want to do this?"

"Yes, I am. And besides, your mom's going to be watching over us. I know she'll make sure things go well. I trust her. And I trust you too."

Cream smiled. "I trust you too, Tails. You're a true friend."

Subtly, Cream slipped her hand over Tails'. The trust they had built up over the past couple of years was unshakable. Now, they were ready to put that trust to the ultimate test with Vanilla's imminent lesson.

"Aw, isn't that sweet?"

Tails and Cream jumped slightly on their bed as they looked to the source of the voice. Vanilla had just entered fromthe bathroom, and had clearly been eavesdropping on the conversation.

"It's good to know you trust each other so much. And yes, Miles, I trust both of you too. That's why we're going through with this the way we are."

Tails and Cream straightened up. Their lesson was about to begin.

"Now, you two..." Vanilla began. "It's time to learn about sex."

And so, Vanilla began her explanation. This whole situation had come around because the two teens had become curious to the "facts of life", and Vanilla decided that they were both old enough. However, she didn't really have any reference material on hand, so she had to think of an alternative solution.

It would be a practical demonstration. Once she was finished with her explanation, she would guide Tails and Cream through the process. After all, the best way to learn something is to experience it firsthand, right? She had made some preparations too, making sure to buy some birth control pills, and ensuring that Cream take them over the past couple of weeks, so as to hopefully avoid any unnecessary... complications.

Soon, the lecture was finished, leaving both teens feeling a little embarrassed.

"So you see, sex is an important part of life. It lets the women give birth to children, and it's a way for two people to express their love to each other, or as a form of stress relief."

"It sounds nice when you describe it like that." Cream said, feeling her cheeks heat up.

"It is." Vanilla replied. "But sadly, there are some people out there who don't realize this. Some would try and have sex purely for some cheap thrill, or even without the other's consent. It really shouldn't be like this, but unfortunately, that's the way things are..."

"The reason you two are going through with this," Vanilla continued, "is that you both trust one another, and want to use this as a learning experience. You have each other's consent, as you do mine. But I want you both to promise me to never use sex for your own personal gain. You should only do so to someone you love, and even then, only if they say it's okay to. Understand?"

"We do." Tails and Cream spoke in unison.

"Very good." Vanilla said with a warm smile. "Now, Cream. I believe you should get ready."

Cream nodded, and stepped off the bed, walking into the middle of the room. After a second's hesitation, she reached down, gripped the hem of her dress, and pulled it up over her head, revealing her delicate body.

Tails' eyes widened in awe as he saw his friend stripping down in front of him. Being still fairly young, Cream wasn't as developed as much as the other girls he knew, yet still looked gorgeous. Her breasts were perky and sweet, and her legs were well toned from the exercise provided by helping save the world from Eggman. And between her thighs was a small, fleshy slit, which Tails knew from Vanilla's lecture was her vagina. After posing for a little, the young rabbit delicately walked back to the bed, standing in front of the teenage fox.

"Both of you still need to prepare yourselves." Vanilla spoke. "Miles, try caressing Cream a little to help her get going. The breasts are always a good spot."

Complying, Tails gently scooped Cream's right breast in his hand, and started fondling it. It felt like a water balloon with a fine layer of fur covering it. Reacting to his touch, Cream moaned softly, shuffling about on her feet a little, unused to a boy touching her in such a way. Tails couldn't help but smile. Cream had such a sweet, innocent sounding voice, and her quiet gasps sounded so alluring.

Suddenly, he felt a tingling down in his nether regions, and looked down to see his cock, swelling to just over double its normal size. Cream saw it too, and gasped in surprise. "Is... Is that what a penis looks like?"

"Oh my!" Vanilla exclaimed. "That's certainly big for one of your age, Miles."

"Yeah, I've seen it do this before, but I never knew what it meant. I guess it means I'm turned on?"

"Indeed you are. Now, Cream. How do you feel down in that same area?"

"A little... wet." Cream answered her mother.

"Excellent. That means you're both ready. Now, on the bed, both of you."

Both obeying their teacher, Tails slipped back onto the bed, Cream following suit. She laid down onto her back, letting the twin tailed fox getting into position.

"Um... Mom? Are you sure that will fit inside me?"

"Honestly, it might not fit entirely." Vanilla answered, sitting on the bed herself. "But it doesn't need to go in all the way. Miles just happens to be exceptionally big. And that's always a good thing. Now, spread your legs a little. Let Miles reach you easier."

Cream nodded, widening the space between her legs. Tails, now fully committed to going through with this, held Cream's thighs, and moved closer. He was just about to get started, when Vanilla interrupted.

"Oh, one second. Cream, this part is going to hurt quite a bit. It's always painful the first time. But it's only for a second, and it will feel good afterwards. Are you both ready?"

"Yes." Tails responded, though it took Cream a couple more seconds to answer "I'm ready.", clearly a little nervous about being put in pain.

Now fully prepared, Tails shoved his member straight into Cream's pussy. He felt something trying to stop it partway through, but it soon gave way, causing Cream to shriek out in pain.

"Are you okay?" Tails asked, concerned.

"I-I'm fine..."

"Alright, Miles." Vanilla started again. "Thrust your hips. Make it so your penis is constantly moving back and forth. Make sure Cream is kept aroused. Remember, sex is a two-way act, so always think of your partner."

Hearing Vanilla's advice, Tails started moving, in and out, over and over. He panted with each thrust, the feeling of Cream's inner walls sliding against his cock triggering a primal urge to fuck.

Cream herself was completely giving in to Tails, feeling his throbbing erection moving through her insides. Her mother was right, it felt really good. whimpering in both pleasure and pain, she gripped the bed sheets tightly, almost in danger of ripping them.

Vanilla meanwhile was witnessing the whole affair, and couldn't help but feel turned on herself. With her busy, single mother lifestyle, she had little time to relieve any stress with masturbating, and as a rule, she avoided pornography as much as possible. But now, watching her daughter being banged by the young fox made urges that had long been dormant start flaring up again. Before she knew it, she had unbuttoned her dress, revealing her shapely, tights clad legs, in the hopes that would help her cool down.

Before long, Tails found himself slowing down. His stamina was getting the better of him, and he was finding it harder to keep up the pace. Noticing this, Cream opened an eye.

"T-Tails, are you o-okay?"

"I... I can't... I can't keep going..."

"Don't worry, Miles." Vanilla spoke up softly. "If you get tired, Cream can take over if she feels up to it. Do you think you can take over, sweetheart?"

"Okay... Let me just get on top first..."

Both gripping each other in a tight hug, Tails and Cream rolled over on the bed 180 degrees, leaving Cream to be the one looking down on Tails. After staring into each others eyes for a moment, the young rabbit sat upright, still attached to the kitsune, and used her legs to lift herself upwards, before sliding down again. Again and again, she repeated the process, essentially riding Tails like a horse.

"Cowboy style..." Vanilla thought. "That was always one of my favorites"

Vanilla's heat was starting to overcome her. She didn't even realize until she looked down that she was massaging her breast through her vest. Giving in, the mother rabbit started rubbing her clit through her panties, softly moaning to herself, unknowingly joining in with the chorus of the two teens' gasps of pleasure.

Suddenly, Cream let out a shriek. She felt the juices inside her suddenly flow out in short, strong spurts, and her body bucked back and forth with each release. Feeling this covering his cock, Tails came too, his load shooting out straight into Cream's vagina, again, in short, strong bursts. The teens rocked back and forth for a couple of seconds, before the feeling finally subsided. Using the little strength she had left, Cream lifted herself off of Tails' member, and slumped down next to him on the bed, both desperately trying to catch their breath.

"That... That was... Amazing..." Tails spoke between pants.

"Tails?" Cream whispered softly. "I'm glad you were my first..."

The two teens smiled sweetly to each other. But their thoughts were soon interrupted by the sound of breathy moaning from the foot of the bed. Looking upwards, they saw that Vanilla had completely lost focus on them, and was now rubbing herself through her clothes.

"Tails, what is she doing?"

"I'm not sure. But it kind of looks like she wants to have sex. She's rubbing her breast and vagina, so it would make sense."

Looking back at each other, both had the same idea at the same time, a devious look spreading across their faces...

Vanilla was so into her masturbating, that she had no idea what was about to happen. Suddenly she felt someone grab her arm, and pull her down onto the bed. Yelping in fright, the milf quickly found herself being pinned down by both Tails and Cream, who smirked naughtily down at her.

"You look a little bothered there, miss Vanilla." Tails said. "Seems like you could use some stress relief yourself."

"And besides..." Cream continued. "We need to thank you for the lesson. I think it's only fair that we return the favor."

"Oh my God..." Vanilla's mind raced. "I've created monsters..."

Before she could object, Vanilla felt her clothes being slipped quickly off of her. With two pairs of hands working in unison, it only took a few seconds for her to be fully nude, her shapely, hourglass figure on display for the pair. Once again, she wanted to object, but was soon silenced by the two, Cream sucking on her nipple, and Tails licking her already wet pussy.

It seemed that consent had been thrown out the window, as Vanilla felt Tails' member enter her, with much more confidence than he had with Cream before him. Cream herself, meanwhile, had moved on from her mother's tit, and went straight for her mouth, kissing her passionately. As Vanilla felt her daughter's tongue stroke and dance around hers, she knew that this was wrong... And yet it somehow felt right at the same time...

"Tails, I have something crazy in mind." Cream spoke, breaking the sound of moaning that had been filling the room beforehand. Moving herself so that she laid on top of Vanilla, she spread her legs again.

"Do you think you could lift me? You could use your mouth to lick me while you do my mom."

"Way ahead of you." Tails answered with a smile.

Doing as he was told, Tails lifted Cream by her thighs, raising her body so that her vag met his mouth. It was a slight struggle, but fortunately, Cream was always light and easy to carry, so he still had the stamina to keep the pace up with Vanilla.

As for Vanilla, she saw her daughter's arms straining, trying to keep her upper body in a comfortable position. Motherly instinct took over, and Vanilla grabbed Cream's shoulders, lifting her upwards, with the younger rabbit's hands resting on the elder's shoulders for added support.

Cream was now completely suspended by both Tails and Vanilla. Her eyes had locked with her mother's, their faces showing pure ecstasy. Tails was doing the work of two, licking Cream's pussy, and thrusting into Vanilla at the same time. It was quite a sight to behold. Or at least it would be if anyone other than the three were there.

The pure insanity of the position they were in, combined with Tails' efforts, meant that a three way orgasm was inevitable. All three cried out into the night, before finally relaxing. Despite the drain in their strength, Tails and Vanilla were still able to gently lower Cream back down onto her mother's body. Tails pulled himself out of the mother's hole, and laid back, thoroughly exhausted.

For several minutes, all three simply laid there on the bed, trying to get their breath back. Eventually, Cream slipped off of her mother's body, and came to rest on her right side. Tails clambered weakly up to join her on Vanilla's other side. As the reality of what had just occurred set in, Tails and Cream's faces turned into a look of guilt.

"Oh man, what have we done...?" Tails spoke awkwardly.

"Mom... I'm sorry..." Cream said, her voice shaking. "I know you said not to do this with without consent... But... I just don't know what came over us..."

Vanilla's expression started stern, before slowly softening, and a smile forming. "I'll let it go this time. You were both caught up in the moment. It's fine. Every teenager goes through urges like that at some point in their life."

The two teens breathed a small sigh of relief.

"Actually..." Vanilla carried on. "This whole thing made me think of something. I think we could all use a little stress relief every now and then. So I have a little proposal for you, Miles. How about you, me and Cream become friends with benefits?"

"Friends with benefits? What does that mean?" Tails asked.

"It's a term for two people, or in this case, three, who are in a sexual relationship, but not necessarily in love. They can use each other to help relieve some stress, and talk to each other about things that you wouldn't normally speak openly about."

Tails' eyes widened slightly. This was sounding intriguing...

"Me and Cream could both be your friends with benefits. You can come to either of us whenever you think you feel the urge again. We could do it individually, or all together, like we did just now. Does that sound good to you, Cream?"

Cream smiled excitedly. "That sounds like it could work! Please say yes, Tails!"

The more Tails thought about it, the more it sounded like a good idea. And besides, how could he say no to that wonderful smile of Cream's?

"Okay, it's a deal! You two are practically family to me anyway. From now on, we're friends with benefits!"

"Yay! Friends with benefits!" Cream cheered with delight.

Vanilla smiled warmly. This might not be conventional. But it was certainly a good decision. Glancing out through a tiny crack in the blinds, she noticed that the sun had long since set. She had no idea what time it was, but it was definitely late.

"Okay, you two. It's time to go to bed. I think it only makes sense that we all sleep together tonight."

Nodding, the two teens laid down, resting their heads on Vanilla's breasts, using them as pillows. Wrapping her arms around both her daughter, and her new "friend", the mother rabbit felt the weight of the nights activities come down on her, and she soon drifted off to sleep. Tails and Cream followed suit, their hands clasped together.

And so, with all three of them now closer than ever before, Vanilla, Tails and Cream slept soundly through the night. This was the beginning of a new chapter in their lives...

Models by KabalMystic
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