Tails loitered around the corner from the hall that led to Cream's apartment. He had been hovering there for at least ten minutes, trying to muster the courage to walk up and knock on the door. He had a crush on Cream. He knew her ever since elementary school, but it was only earlier this year that he started to have a crush on her. He didn't care that she was promiscuous; he was in love with her. He wanted to make her happy in a way that riding a bunch of prodigously-sized cocks could not.

After mustering up the courage, he knocked on the apartment door. He didn't have any sort of big speech prepared; he was just going to wing it, ask if she wanted to go out. Worst case scenario, he could still shoot to have sex with her. Sure, he wasn't as big as the meatheads on the football team, but it's not like she'd turn him down for that, right?

His plan was instantly dashed when the door opened. Standing there in the threshold was Vanilla, of whom Cream was practically a mirror image. Supposedly she was about thirty, which would mean she gave birth to Cream when she was still in high school. Tails thought for a brief moment about all the promiscuous sex Cream was having, and if that meant she, too, could become pregnant if she wasn't on the pill.

Those thoughts were fleeting in his mind as he looked up at the buxom rabbit. She had a body that hid well the experience and mileage behind it, between being pregnant at a young age and then spending many dozens of hours at the gym afterwards, beating back the pregnancy weight and added fat. He was able to tell this because she answered the door, for all intents and purposes, almost completely naked. All she wore was an open front chemise and a thong so tiny it seemed to be in the process of being devoured by her plump labia.

"Well hello there!" she said, staring down at him. "Can I help you with something?"

"U-uh, is Cream here?" Tails asked through a stutter.

"No, she isn't. I think she's out and about with some friends, but she should be back soon." Vanilla replied. "Would you like to come inside and wait for her?"

"S-sure." he couldn't explain why, but in the back of his mind, Tails had the vaguest sense that saying yes was actively walking into and inviting trouble. He ignored the errant thought; he wasn't about to let a random sour gut instinct get in the way of love.

Vanilla stood aside to let him in. Tails removed his shoes and sat down on the couch in the living room area. The TV was on, and she appeared to be in the middle of watching a superhero movie, but so many had come out starting since before he was born, he couldn't tell which one it was just from a single frozen frame.

"You'll have to forgive me." Vanilla called out as she went to her room. "It's been slow at the office for me, so I took the day off to laze about at home. I wasn't expecting visitors." She returned, now wearing a rather small and ill-fitting bathrobe over her half-naked form.

"Of course, I bet you loved what you saw." she added, sitting down on the chair to the left of the couch. "Never met a man that doesn't love taking in an eyeful."

Tails didn't say anything out loud, instead trying to not stare at her half-naked form too much. It was true, she was very attractive and seeing an almost naked body in person was much different from seeing it on a screen, but Tails also didn't find it very appropriate to be ogling the mother of the girl he was here to ask out on a date.

"So what's your name, big guy?" Vanilla asked. Tails was taken off-guard being called "big guy"; if it was anyone else, he would have thought it was an insult, but Vanilla seemed to be acting playful.

"My name? It's Miles, but my friends call me Tails." he said, then gestured half-heartedly at his two tails swishing around behind him. "You know, for... obvious reasons."

"Well it's nice to meet you, Tails." Vanilla said, then stood up. "Can I interest you in a drink? I'm not actually sure when Cream is supposed to get home."

"I wouldn't want to trouble you." Tails said.

"It's no trouble at all!" Vanilla insisted. "Besides, what kind of host would I be if I didn't offer some kind of refreshment?"

"Well, okay, then, if you insist." Tails said, but Vanilla was already standing up to head to the kitchen. The bathrobe was very short, and only served to accentuate the length of her legs even more. Tails may not have been confident enough to look fully at her when she was watching him, but with her back to him, he did subconsciously glance over at her. The bathrobe was short enough that he could just barely see her butt, and it only served to accentuate her legs. She had it going on, indeed, but he was not going to be deterred from his goal.

Vanilla returned less than a minute later with a glass of juice of some descriptor. It was dark pink, opaque, and ice cold.

"Thank you." Tails said, taking the glass. He gave it an experimental sip. At first he thought it was pink lemonade or perhaps some sort of passion fruit, but it was sweet in a way that he did not expect. Guava? It had to have been guava.

It was quite delicious, and before he knew it, Tails had drank the whole thing. He set the empty glass down on a coaster on the coffee table between the couch and chair.

"So tell me, what did you plan on doing with my daughter?" Vanilla asked. From anyone else - a very protective dad, for example - it would have been said with a challenging tone, judging his character even before he could provide an answer. Vanilla's tone, however, suggested... condescension? Was she mocking him?

That aside, though, it did make Tails stop and reevaluate what he was doing here. What was he looking for by pursuing a relationship with Cream? Was it just an awakened crush, or was he also looking to protect her or give her some sort of fulfillment that men could not??

"I... I..." he stammered.

"What did you plan to do together?" Vanilla asked. "Go to the movies? Take a trip down to the malt shop? Maybe win her a kewpie doll at the county fair?"

She stood up and moved over to the couch, right next to Tails. The robe slipped down her shoulder a bit. Her huge breasts began to peek out. He looked away, trying to hide his embarrassment.

"M-miss Vanilla, I just-" he began. Why did he feel so hot all of a sudden?

"Do you think those sort of vapid expressions of love will make her happy?" she asked, shaking her head. "Oh, you sweet, naive summer child. Cream is not a delicate flower to be put on a pedestal and viewed from a distance. She's not the gentle-hearted girl next door.

"She's a fuck doll. She's the girl who likes it rough. If you are unable to keep up with her, she'll wring you dry like a sponge and discard you without a second thought."

"Miss Vanilla!" Tails exclaimed. "That is your own daughter you're talking about!" As much as he was aghast about Vanilla's incredibly lewd descriptions, he found himself getting excited at the thought of Cream moaning in sheer bliss on top of him. Or just in general.

"How do you think I know about all this?" Vanilla asked. "We fuck intensely, repeatedly, almost every night, now." She was getting very close to him. Uncomfortably so. "If you're going to come onto Cream, I gotta make sure you are -up- to the task." She placed a slender hand on his crotch and gave him a gentle rub. "It's been a few minutes, so the juice should be kicking in any minute now."

"AAHH! Vanilla, stop!" Tails exclaimed, though despite his protests, he couldn't bring himself to try and move her hand away from his junk. He was made very aware of the substantial bulge that he was now sporting. How long was that there?! More importantly, it felt like a much larger and much harder erection than any he could ever remember having.

"Well now!" Vanilla said in surprise. "How long were you planning on keeping this a secret?! This isn't just any ordinary cock; it's a weapon!" Vanilla leaned more into Tails, pressing her boobs into the side of his face.

"It's not that big, is it?" Tails asked. He never saw another dick before unless it was in porn, and the guys in porn all had dicks like a third arm.

"You'd be surprised how many guys are actually not this big!" Vanilla said. "And you're still a growing boy! Just imagine what you'll be like once you grow up!"

Tails could appreciate such a compliment, even if she was actually lying to him. The fact that she was rubbing his dick through his pants, however, was something he still couldn't comprehend!

Vanilla unzipped Tails' pants and pulled down the front enough to reveal his thick cock. The fur on it was white like on his chest and stomach. The foreskin strained to stretch with the length and threatened to pull back over the head. Beads of precum were oozing out of the meatus and dripping down the length.

Vanilla gripped the dick and slowly, expertly jerked him off. Tails knew he was being molested, he knew this was wrong because he was underaged, but at the same time, he didn't care. His heart was pounding in his chest. His loins were burning with a need for release like nothing he ever felt before.

"So you said you wanted to see Cream, right?" Vanilla asked. Tails nodded his head, but he would have said yes to anything at the moment. His brain felt hazy, and all he could think was how good her delicate hands felt on his dick. "Well, since she won't be back for a while, you will get to entertain me in the meantime."

Vanilla broke away from him and stood up from the couch. She sauntered exaggeratedly to her bedroom. Halfway across the living room, she undid the tie on her bathrobe and cast it off, letting it fall to the floor. The thong she wore was so small and thin from behind that it took Tails a second to realize she was still wearing it. A few steps away from the robe, she threw off the chemise as well in one graceful shrug. She disappeared around the corner into her bedroom.

Tails hopped up off the couch after her. He didn't remember throwing off his clothes, but by the time he went through the doorway into Vanilla's bedroom, he was already naked. Vanilla was laying on her back on the bed. She had discarded her thong on the floor, which was currently next to Tails' feet, and her legs were spread apart. His gaze moved down from her eyes to her gooch. She was trimmed down there so her pubic hair didn't stand out so prominently from the rest of her fur.

"Well, are you gonna keep staring, or are you gonna come let mommy take care of you?" Vanilla asked sweetly. Tails' dick throbbed at the prospect, but what part of him could still think rationally through whatever was in that fruit drink hesitated.

"This... this would be my first time." Tails mumbled awkwardly. "I wanted my first time to be with Cream..."

"Oh come on, don't be like that." Vanilla said. "There's nothing special about having your first time with anyone. The only thing that matters in the long run is if it was a truly enjoyable experience, and that your first time didn't sour the entire concept of sex for you. You do find me attractive, don't you?"

"Uh huh."

"Then stop waffling and cum to mama!" She said. Tails climbed onto the bed with her, his heart continuing to pound. It was ringing in his head. He crawled on top of her, resting his weight on top of her. He had hugged his own mom many times before, but this was completely different. He could feel Vanilla's warmth across his entire body, the softness of her stomach pressing against his, her enormous breasts pressing against both of his cheeks, and most prominently, the heat emanating from her crotch against his dick.

He really was about to lose his virginity, and to the mother of the girl he sought to be with, no less.

"Does this feel good, Tails?" Vanilla asked.

"It's so soft and warm." Tails said, though even he wasn't entirely certain if he was referring to her body or the entrance to her pussy.

"Think you can put it in on your own?"

"Y-yeah. I can do it." Tails blindly prodded around with his dick, feeling for Vanilla's entrance. He felt the tip slip in between her pussy lips, and the entire shaft quickly followed suit. He didn't seem to push into her so much as fall in. It was a weird feeling, to say the least; her insides were hot and her muscles seemed to tug at him in an attempt to pull him deeper, but none of it was uncomfortable like he thought it would be. In fact, it was probably the most satisfying thing he had ever experienced. Vanilla had a strong motherly vibe about her that made this hug in all its forms comforting in a way he didn't realize he was missing out on.

"It feels so warm inside you." Tails said. "It also feels really good."

"It'll feel much better once you start pushing in and out." Vanilla said. Tails nodded his head and began moving his hips. With how tightly her vaginal muscles were gripping him, he assumed there would be a lot more resistance, but to his surprise, he glided in and out of her pretty easily. His dick was already fully erect, but something about being inside her pussy was making him even bigger and harder. The muscles in his cock felt like it would shoot off like a rocket from the strain of being at its fullest potential, but now he felt like it was trying to push past that plateau.

"I can feel it twitching inside me!" Vanilla gasped. "You're... getting really worked up, aren't you?"

"It's tingling so much!" Tails panted as he developed a rapid, almost frantic pace. The tip of his dick was burning in a strange way that made it feel very good, and he wanted it to burn even more. Suddenly, an overwhelming wave of bliss surged through his body. His hips went wild, pounding into Vanilla repeatedly. Something hot was coming out of his dick. He felt like he was peeing, but this was clearly different.

"Aaaaahhhnnn! Nnhh! Nnhhhh!" He panted, nuzzling his head into Vanilla's breasts.

"Hmm, I wasn't expecting your first time to be so... quick." Vanilla said, a hint of disappointment in her voice. "How was your first orgasm?"

"That was... intense!" he said through heavy breaths. "My head feels all dizzy now!"

"Yeah, that never goes away, which is good. I love it when I can cum so hard I barely remember my own name."

"Did you cum, too?" Tails asked.

"No... that'll be something you'll want to work on." Vanilla explained. "It's not good to keep a girl wa-HEEHH!!"

Tails suddenly took a more aggressive stance in her arms. He braced his knees against the bed and hiked her legs up around his waist. He pounded into her with incredible vigor. It felt good and right to do this, even without that overwhelming finish. He loved how it felt to be this close and intimate with Vanilla. Aside from the obvious age difference, Cream was definitely a spitting image of her mother. Considering how young Vanilla looked, it was easy to imagine that Cream would look even more like her in about five years. It made it easy to imagine he was having sex with Cream instead of her mother.

"Unnhh, unnhh, f-fuck!" Vanilla gasped. "Now that's more like it! Little boys are so energetic!"

Tails could feel the burning in his dick again. He was going to cum again, and so soon after the first one! He tried to hold himself back this time, at least long enough to make sure that Vanilla could cum, too. She hit her orgasm after a minute or two; Tails could tell when she did because her vaginal muscles suddenly started gripping him in a rhythmic fashion. A few seconds later, she started gasping and moaning very loudly in orgasmic bliss. Given the sizable delay between when she had her orgasm and when she actually responded to it, it was likely she was putting on a show for Tails' sake, make him feel like a stud. In the heat of the moment, Tails was of course not able to make this observation, but it became fairly obvious to him afterwards.

In the heat of the moment, seeing, hearing and feeling Vanilla cum was enough to push him over the edge even harder than the first time. He involuntarily let out a loud, guttural cry as he blew his young, thick wad into Vanilla. He actually did it. This was the first time he ever made a girl cum! It was empowering, invigorating! For a few seconds, he could feel some primal beast awaken within him, whose only goal was to breed and fill as many wombs as it could find with its potent seed.

Then suddenly, his spasm of invincibility was over, and following it was exhaustion like he never felt before. He slumped forward on top of Vanilla, who had stopped squeezing his dick with her vaginal muscles and held him tenderly in her arms. He lay there in a stupor, not able to process much of anything in the afterglow. He didn't know how long he lay there, but at some point his consciousness sprung back to life and he perked up.

"There there, now." Vanilla said, holding him tightly.. "Just relax, little one."

"Huh... huh... that was amazing!" Tails exclaimed. "I've never had sex before, but I always knew it'd be good, but not THIS good!"

"And you are a natural for being so young and inexperienced." Vanilla said lovingly, but then her tone immediately changed. "But the key word there is inexperienced. As you are right now, you'd be able to get with Cream easily... for a night or two. After that? She's going to see you as just another dick to ride when she's bored."

"How do I get with her... you know... longer than that?" Tails asked.

"You'll need to train up. A lot." Vanilla explained. "If you're serious, I can help you with that. Practice your thrusting technique, making you last longer, become more confident."

"Can you? I really like Cream, and I want to be with her." Tails said.

"Then we can start immediately."