A/N: Appreciated the positive reaction to chapter one.

-XXX-

The TV was on and a romantic movie was playing. But the couple on the couch were not even paying attention to the movie; instead they were preoccupied with each other.

Tails and Sally were in a heated make out session, having lost interest in the movie halfway through it. Mostly because when the protagonists started a make out scene, Tails arrogantly bragged that his kisses were better. It was all the first step of a plan to get Sally to put out. The chipmunk took the bait and challenged the fox to prove it.

So far, they had been going at it for five minutes and the furthest Tails had gone to being intimate was tongue wrestling. If he wanted Sally to know how deep he wanted to go, he was going to have to drop his inhibitions.

With a tentative hand, Tails gently brushed her breast. He half expected Sally to stop kissing him and swat his hand away. She did not, so that was a good sign. It emboldened him to fully indulge himself and he cupped the entire breast in his hand, giving it a soft squeeze. Sally responded with a soft moan into his mouth.

So she was OK with him touching her boobs. What about her ass?

Tails turned his attention from her breasts and moved his hands to her thighs. In total contrast to being a princess, Sally's casual attires were always revealing. Her shirts and blouses were always generously parted in the middle to reveal some cleavage and her shorts and skirts always exposed some thigh. Today was no exception. Her excuse was that it was hot out. Well, given that it was summer, she had a plausible reason to dress like that. Just because she was a princess, does not mean she had to keep up appearances every moment of her life. Rapunzel walks barefooted and nobody says anything.

Anyways, back to the action. Tails slowly caressed her thigh, sneaking his way up to the hem of her shorts. Still, the chipmunk did not oppose his advances. He figured "what the hell" and went for it, moving his hand up Sally's ass and giving it a squeeze.

Still, Sally did nothing. In fact, she even did Tails one better and swung her leg over, straddling him. Tails took that as the green light to keep going. All fears evaporated and he leaned into it, his hands wandering all over the chipmunk's body, in particular, her tits and ass, touching, caressing, squeezing... it did not take long for him to get hard. He was sure Sally could feel it, as she was sitting directly on top of it, yet she did not comment. Maybe she was perceptive enough to know where this was going.

It was time to be less subtle and to be more direct.

Tails grabbed the shoulders of Sally's open waistcoat and pulled it down her arms, leaving her in her short sleeved crop-top; still green light. Inside, Tails was smiling in triumph. He grabbed its hem and made to remove that as well.

That was when she reacted and shrugged his hands away. She broke the kiss.

"Tails, what are you doing?"

Tails suddenly felt deflated as all his confidence left him. "Uh... I thought we'd go further than this." He felt like a socially awkward nerd who was taken pity on by a girl, only to jeopardise their budding friendship by trying to make things sexual between them.

"What, you thought we were gonna have sex?" Sally asked incredulously. "Tails, baby, I'm just not ready for that kind of step in our relationship."

"But... we've been dating for two months now. I mean, don't you think it's time our relationship got more intimate?" Tails tried to explain, a blush creeping up on his cheeks. It still felt weird to say it directly.

Sally frowned. "What? Tails, I dated Sonic for six months and never even showed him my boobs. What makes you think I would go all the way with you after just two months into our relationship?" the chipmunk countered with a question of her own. Of course, Tails failed to answer it, so she continued. "Besides, I'm the princess. I have to maintain a dignified figure."

Tails would have laughed if he were not so sexually frustrated. She definitely looked less dignified now, clad in only a crop-top and shorts that barely reached her knees. One would think she is not even a virgin to begin with. "You're also my girlfriend, Sal."

The chipmunk rolled her eyes. "Ugh, you're just like Sonic, or any other boy. When you ask a girl out and she says 'yes', you only have one thing on your mind: 'when do I pull her panties off?' I thought you were different, Tails."

"Well, what do you expect? In any relationship, the girl always has to know that sooner or later, the topic of sex is gonna come up, especially when the relationship has been going on for as long as ours." Tails brought his hands up to gently rub Sally's arms, going all the way up to her shoulders and coming to rest on either side of her cheeks. He looked straight into her blue eyes. "Sally, I really wanna do this with you."

That brought a sigh out of the chipmunk. She wrapped her own hands around Tails' and slowly lowered them. "Not every relationship ends in sex, Tails." Just then, her phone beeped. She got off her boyfriend and picked it from the table. It was a message from her mother. "I have to go. Royal classes."

Tails slumped in the couch, a dejected look on his face. "Fine."

Sally knew his current mood would not get an "I love you" out of him, so she did not bother saying it. She grabbed her car keys and headed for the door. Tails made no move to see her out, instead just staring at the TV with a scowl. She opened the door but before stepping out, wanted to at least show that she still cared about him, that this little fight was not the end of their relationship. "I'll see you later, K?"

The fox only grunted in response. Sally sighed in resignation as she stepped out, closing the door behind her.

The moment Tails heard her car drive away, did he finally let out his anger. "Fuck!" He punched a cushion in frustration.

The movie still played on, this time showing a couple making out, with the boy undoing the girl's clothes and the girl doing likewise. Tails angrily turned off the TV. It was as if the movie was mocking him that he did not get some.

Now he fully understood why Sonic broke up with Sally before. Sonic had always told him that they broke up because of certain disagreements he never mentioned. Now, he understood what those "disagreements" were. Eventually Sonic started dating Amy, a girl that was all too happy to spread her legs for him.

That was two years ago, when Sally was eighteen. She had been single ever since... until Tails asked her out and she accepted.

But like Sonic, Tails was a person who believed in sexual relationships. To him, no relationship could survive without sex. If a couple were spending their "quality time" just talking and making out without any form of sexual activity, a relationship always tended to stagnate and become bland... at least from his perspective. Sally might think their relationship was still going strong but to Tails, it was stagnating. He saw sex as the only way to stir it up again; Sally thought otherwise. And if Sally was not going to put out, then he might as well break up with her. But he could not bring himself to do it. If he did, not only would he break her heart, he would also prove Sally right that all boys are merely after sex in every relationship.

He still loved Sally, but he also had his sexual needs to think about. If Sally was not going to satisfy them...

Tails sat up as an idea crept into his mind. An idea that would leave both parties getting what they want. Sally would still remain a virgin and Tails would still get to lose his virginity. Everybody would win.

"Maybe, just maybe... I could cheat on Sally."

Only when saying it out loud, did Tails feel like a jerk. But his sexual urges were getting the better of him. If his girlfriend was not putting out, then he would find another girl who will. But the question was, who?

That was something he would have to worry about later. Now, he had the issue of his still hard dick in his pants. Like seriously, Sally was sitting right on top of it. She could feel his heat, his arousal, yet she still had the gall to say no and just walk away? Even when she refused the sex, could she not have at least taken care of him? Maybe give him a blowjob, handjob, something; another reason that all but reaffirmed his decision to cheat on her.

"Sorry, Sally. I love you, but you've forced my hand."

-XXX-

Yep. His hand was forced, alright.

That night saw Tails once again seated at his laptop, in the nude, streaming yet another porno. This one involving a muscular lion sharing his dick with two thick cheetahs. One was bouncing up and down his dick while the other squatted over his face as he licked her pussy.

Tails slowly stroked his dick, which was already oozing a good amount of pre-cum. He had to go slow, as it was more sensitive this time and it twitched frequently.

Tails' had cranked the volume up so the entire room was filled with the erotic sounds of the video. He was glad to be living alone, as no one other than himself could hear the moaning, slapping and slurping.

The camera zoomed in on the lion's mouth as his tongue continued to lick away at the cheetah's clit. Then she gave off a loud moan and squirted her love juices into the lion's open mouth, with a few stray drops landing on his muzzle and chest.

That proved to be a massive turn on for Tails, as his hand tightened around his shaft and his stroking increased in speed. He let out a moan as his climax edged ever closer.

The cheetahs then got off the lion and knelt before him, preparing for the moneyshot as he jerked off. His cum shot out into their mouths with some getting onto their faces. The cheetahs cleaned off his dick together and then started to lick the stray shots of cum off each other's faces.

Tails let out a loud moan as his dick twitched and his cum shot out with greater force than usual. But his eyes were glued to the video; he did not glance under the table to witness his sperm shooting out. He kept stroking until his dick gave off its final pulses and the last drops of cum dripped onto the floor, missing his cum towel. When he finished, he finally relaxed and slumped into the chair.

The familiar feeling of post-masturbation disgust once again settled on him. Of course he would not have done this if Sally had just been a good girlfriend and put out. All this was her fault. She had better not blame him when he starts cheating on her and she finds out.

Tails laughed to himself. Was he really that confident that he could find the girl to give him pussy just like that? It was definitely gonna be harder than he thought.

When he felt comfortable to move again, he pulled out two tissues from the box and wiped his dick. As he glanced at his cum-stained towel under the table, he was surprised to see that other than the towel, the wall was also stained with fresh splotches of his sperm. He had almost forgotten that his new diet not only increased his sperm count but also the power of his ejaculation.

While Tails marvelled at this, he was also gonna have to clean that up. He pulled out three more tissues and wiped his sperm off the wall. He tossed the used tissues into the bin, before walking to his bed and getting under the covers.

While saying "cheating on Sally" was easy, actually doing it was hard.

For starters, finding the ideal girl to do it with. Most people considered Tails to be a stereotypical nerd: socially awkward, especially around girls but it was quite the opposite. He was actually pretty good at talking to girls. Some of his peers in high school were girls and he occasionally ran into a few. But he could not just say "hey, (insert girl name here), wanna go have sex?"

Not only that, but Tails had a very picky mindset on the type of body the girl he sleeps with should have. It was no secret, judging from the types of porn videos he watched that he was attracted to thick girls; the bustier and curvier, the better. Those were the kinds of girls he wanted to take his virginity from him. Despite Sally's own curves, which were still enticing enough, she was not really up to Tails' standards. He only knew two women who fit that bill.

The first was Vanilla, the mother of one of his friends. Sure, she was twenty years older than him but that still did not stop Tails from lusting after her. In spite of how shameful it felt to admit it, she was the cause of his thick girl fetish. She was widowed; her husband passed away with a severe bout of pneumonia long before they knew each other. And since she made no attempt to get back into the dating world (as far as he knew), she would not feel any guilt of infidelity if he chose to sleep with her. Tails smiled to himself. He could already imagine her on top of him, fully naked as she bounced up and down his dick while he squeezed her enormous breasts and spanked her luscious ass.

But unfortunately, Vanilla was very moral. Tails could not imagine her readily agreeing to have sex with him. Worst case scenario, she could say no and snitch to his mother. The last thing he wanted was his parents knowing about his sexual urges. He was never given "the talk" since he was precocious enough to find out about the birds and the bees on his own. Anyways, he could only imagine the type of scenario that would play out if he asked Vanilla: she would mention their age difference, pointing out that if word got out, she would be seen as a paedophile and be sent to jail, regardless if it was his idea. Then she would also give him a boring lecture about sex, restraint, waiting until marriage... he did not need all that noise. So Vanilla was ruled out; which left him with girl number two:

Rouge.

She was the perfect choice for Tails. Not only did she have the body, but she also had the sexual experience. Sure, Vanilla boasted a thicker body, but Rouge was definitely uninhibited when it came to sex. There was no way Tails could imagine something like "age" or "immorality" get in the way of Rouge's sex life. She had her many sexual trysts to prove it; and that was one of the issues the fox had to address. It was no secret that the bat had many sexual partners. Most people would consider her promiscuous or just a dirty slut. Maybe that was also what Tails thought, since he was just considering her for sex. Given her sex life, a logical person would assume she's a prostitute carrying a disease but Tails was looking beyond that. They were friends... of sorts but Tails could not help but feel that she wanted to go a step further.

In the first seven months after his birthday, most of their conversations never failed to have Rouge throwing in teasing remarks or sexual innuendos. Every time they texted over the phone, Rouge never failed to send him provocative photos; there were never nudes but ranged from pictures of her dressed in sleeveless crop-tops and bum-shorts to pictures of her in her bras and panties, all of which came with the caption "when you're ready". But that was when Tails' mind was still innocent

Well, now Tails was ready.

If that was not enough, one time, when she had a little too much to drink, she claimed to have a boy crush on him and wanted to be his first.

Looks like she would get her wish.

But Tails could not prematurely get his hopes up. It was, after all, in Rouge's nature to sexually tease someone just for the fun of it. Of course, her sex life said otherwise, but there was no guarantee that she would all too gladly accept sleeping with him.

Still there was no harm in trying. What's the worst that could happen?

Well, she could say no, humiliate him in front of his friends as well as hers, and make him feel so ashamed of showing his face in public ever again.

That worst case scenario was enough to have Tails resign himself to remaining a virgin until Sally gave him the say so. No! He would not just back down based on what his imagination is telling him. But rather, what Rouge herself would tell him.

Rolling over in his bed, Tails reached for his phone on the nightstand. He opened his messaging app and scrolled down until he reached Rouge's chat. His finger tapped her icon and the chat opened. Their last conversation was two days ago and it was merely about Rouge asking for assistance on how to fix a minor problem on her laptop. Ever since Rouge stopped her teasing, their conversations had become so few and far between, the fox wondered if the provocative photos were the basis for starting one in the first place.

Tails activated the keypad, typed in a "hey" and hit "send". Then, he waited.

A minute passed. Nothing. Two minutes. Still nothing. Three. Four. Five...

It became clear that she was not online. Maybe she was already asleep. Or her phone was dead. Or she had left it in another room. His dirty mind suggested she had most likely invited one of her sexual partners over for a night of hot sex and she was simply ignoring her phone. But whatever the reason, it did not appear as if she was going to answer anytime tonight.

With a sigh –he did not know whether it was of relief or resignation- Tails locked his phone, put it back on his nightstand and tried to sleep but he could not. His mind was screaming at him for what he had just set in motion: inevitably, tomorrow she's gonna find your text and when she replies, will you have the guts to tell her what's on your mind?

Sleep eventually overcame him. As he drifted, he left his ears perked up, in the slim hope that his phone beeped to notify him of a new message.

-XXX-

A/N: OK, first off, I know I promised some of you (who will remain nameless) that this chapter would start the lemon-fest. Well, sorry to postpone. To be honest, I had different other ideas for how this chapter would end and this one I've chosen isn't even sitting well with me. I have half a mind to rub it off and put in another one of the many ideas I have but that would mean more work. I've already rewritten this chapter like five times already. Anyways, I hope you like what you're getting now, coz this is just a tip of the iceberg.

Enjoy.

J.W.H. 10