Tails' Summer Experience/Cream
Index
Maybe it was his fate to be on the very fringes of social circles? He already had problems trying to socialize and find a girlfriend. It didn't help that things like that kept happening, where his quarry's attention will suddenly get drawn elsewhere, and he finds himself watching from the sidelines. The same thing happened whenever Sonic was around, which is partly what led to them drifting apart. Tails didn't want to constantly play the role of second banana.
"That's a bad first impression on this holiday." a voice said. Tails looked over at the boat to his left. Maybe it was due to his depression that he didn't recognize the boat when he should have, but standing on the deck was the familiar face of Knuckles. To his surprise, he was also completely naked. There were no laws against it on the island, of course, but Knuckles was able to get away with it more than anyone else because of his Herculean physique. He worked out a lot, so there was barely an ounce of visible fat on him.
"Hey, Knuckles." Tails said.
"What's eating you?" Knuckles asked. "You can talk to me."
"Just... girl problems, I guess." Tails climbed onto the boat and sat down on one of the seats on the rear of the boat. Knuckles took a seat opposite from him. His monstrous meat lay out on the seat like a third leg. Tails didn't mean to look, but it was difficult not to.
"What kind of girl problems? Can't find one?"
"That's exactly the problem. Not only can I not find one, but I don't have the kind of charisma as either you or Sonic."
"It's not just charisma girls are interested in. A lot of girls like a guy with a big brain, and I know you have that in spades. Like the reactor you built! Or all those planes."
"I tried that earlier. The girl didn't take it at face value, and wanted to see proof that I didn't happen to bring with me."
"Geez, that sucks. Well, if that's the case, make them feel special. Listen to what they have to say, even if it's something you couldn't care less about or understand."
"Cream told me the exact same thing earlier today."
"Cream? You mean you just..." Knuckles leaned forward. "What happened? Did you two not hit it off or what?"
"What are you talking about?"
"You didn't know?" Knuckles rolled his eyes. "Cream has had the hots for you for a long time now! Hell, the whole reason she's even out here for the summer is so she could see you!"
"Really?! But then... why was she... trying to..." Tails stammered, trying to find a logical answer for Cream's behavior.
"Sounds like you're gonna have to sit down and have a talk with her." Knuckles said, standing up. "Well, I'm sorry to cut this short, but I've got to run. Got a meeting scheduled." He hopped off the boat onto the pier, still naked. "I'll trust you with the boat. No joyrides, got it?" he joked, chuckling to himself a bit, but seeing that Tails was in no mood for jokes, he immediately stopped and headed to the shore.
* * *
There was a knock at the door to Sally's room. She opened the door, at first a crack, since the only thing she was wearing was the thong she bought earlier, and to get front seats to the beauty that was her body was a privilege that had to be earned. As she had anticipated, Knuckles was standing there, completely in the buff. He stood a head taller than her, muscles rippling. His dreadlocks were brushed behind his shoulders. All in all, he was the perfect specimen of masculinity.
"How good of you to arrive." Sally purred, stepping aside to let him in. "The prisoner has been very unruly. She thought she could force Her Majesty to cum before I say so. I've called you here for your... expertise. Her arrogance and ambition must be punished!"
"Where is she now?" Knuckles asked. Sally brought him over to the bed, where Vanilla was tied down to the bed. She simply stared at Knuckles, her eyes filled with a knowing lust. Like Sally, she, too, was wearing the lingerie she bought earlier. Her hands were tied around the bedpost behind her, her mouth stuffed with a red ball gag, and her legs splayed out and folded inwards so her heels touched her inner thighs and butt. The mere sight of her caused his cock to jerk up an inch.
"As you can see, she's quite the spunky one." Sally explained. "So, I want you to fill her up with all the spunk you brought with you!"
"You got it." He planned on just fucking Sally when he arrived at the island, but on his way here, he got a call from Sally telling him that there was a change of plans. It suited him just fine, since Vanilla was an extraordinary MILF. The roleplaying was just a kink of Sally's.
He climbed up onto the bed and pulled up the sheer loincloth that covered Vanilla's womanhood. Her position made the lips even more defined and bulbous. Knuckles dipped his fingers in between Vanilla's plump folds. His fingers, unlike Sally's thin, slender digits, were large, twice as thick as hers, and almost seemed to be bulging of muscle like the rest of his body. They dug into her muscles and assaulted her sweet, tender areas. He wasn't gentle about it, but he wasn't looking to hurt her, either. When he found a sweet spot that made Vanilla twitch and jerk, he probed that area mercilessly.
Vanilla moaned through the ball gag and thrashed around in the bindings. He seemed to have foreknowledge about the most sensitive parts of her insides, and he was very aggressive about violating them. Her urethra felt like it was being tasered as she was sent careening over the edge. Her eyes rolled in the back of her head and she let out a muffled scream. Her hips were bouncing up, fighting against the rope that held them down. Knuckles dipped his head down and closed his lips over the upper half of her womanhood just in time to drink in her delicious girl cum. It was sweet as freshly squeezed peach juice, which was a very appropriate analogy, he decided. His tongue poked between her folds and rolled against the roof of her love canal. Vanilla trembled violently, her breathing erratic. She was already on the verge of another orgasm, but before she could fall off the edge, Knuckles drew his head away. She moaned frustratedly, jerking around in the bindings.
Vanilla didn't have to wait very long, though, for the next stage of her "punishment". Knuckles climbed over her, his masculine scent radiating off his body. His enormous cock prodded against the entrance to her womanhood. She couldn't see it, but she got a good idea of how big it actually was as it slid past her quivering labia and deep into her insides. She gasped at the sheer size of it. It was practically as big around as her forearm and probably just as long! It was a wonder he could even fit inside her!
Knuckles' thrusts were slow, but powerful. Each thrust forward jostled her in her bindings. The ridged head was flared, and every motion going either way scraped against her G-spot. While Vanilla did enjoy it, she knew she wouldn't last long. Barely ten seconds into it, and her mind shattered into a thousand pieces as the pleasure built up before exploded again.
Knuckles and Sally grinned at the sight of her eyes rolling in the back of her head and her pupils dilating. She was babbling incoherently through the ball gag; even if it wasn't there, it was highly unlikely she was even using words.
"Fu fu, how does it feel?" Sally asked, patting Vanilla's stomach. Knuckles dipped his head down and closed his lips around one of the nipples that poked through the folds in the camisole. His mouth was like a vacuum on her tit, easily coaxing out her sweet milk. "I bet it feels excruciatingly pleasant, like every thrust makes you feel like you're gonna cum."
Vanilla looked over at her. Tears were welling up in her eyes, but she wasn't crying. Sally was right. The cock was so big inside her, rubbing against all her sensitive areas at once, she couldn't go a few seconds without feeling like she was about to spray her pussy juices all over the ceiling and the opposite wall.
"This is what the Acorn Kingdom does to their prisoners. You think, because you broke into my chamber, that you are strong? The warden, here, will fuck you until you sing and tell us who you work for!"
Knuckles continued to fuck Vanilla while he sucked on her nipple and drinking her milk. Sally took her place at the other teat, and for the first time in a long while, Vanilla had the pleasure of getting both breasts suckled. It was an experience she longed for, but now was actually the worst time for it, since she was already driven mad by the non-stop, multiple forms of stimulation. It was almost impossible to tell when she was about to cum, when she was cumming, and when she was in the afterglow. And somehow through all this, Knuckles didn't even break a sweat or bust a nut inside her yet. Against everything else she was feeling, she actually wanted to feel his horse cock spray its hot sticky wads all over her cervix.
However long it went on for, Vanilla was uncertain. She drifted in and out of consciousness; the energy drain from one orgasm would cause her to lose track of reality while a second one would launch her right back into the thick of it. Her limbs were sore, her breasts practically numb from all the blissful tingling. It was at this point that Sally finally sat up and looked over at Knuckles.
"I think she's just about done. Finish her off, and then we can begin the interrogation." she ordered. As if on cue, Knuckles grunted and moaned like a pissed-off bull, slamming his hips into Vanilla's pussy. All the veins on his cock throbbed and pulsed as thick gooey ropes coated the back of Vanilla's love canal. It was such a long time since she experienced this that she forgot what it was even like to get a pussy full of cum.
He continued to fire one spurt after another into her until finally his frightening meat shaft stopped throbbing and pulsating. Sally untied Vanilla from the bed and tossed the ropes to the side. She was unshackled, but the ordeal left her in no condition to move. Her heart was racing like it was ready to explode any moment, her face was marked with dried up tears, and her limbs were very sore from fighting against the restraints. Sally knelt over her. Her pussy lips were gaping open and leaking an impressive volume of Echidna spooge.
"Maybe now you're a bit more willing to talk." Sally purred, patting Vanilla's stomach again. "You're gonna tell us everything about who you are and who you work for, or it's back on the rod for you!"
* * *
Tails hung out on the boat, not moping or brooding. He had a strange mix of emotions, including guilt, confusion, and regret. He was trying to rationalize why Cream attempted to hook him up with another girl when she had a crush on him, but his theories were all illogical and inconclusive. The only way he'd get a definitive answer is to ask Cream directly.
Fortunately, he didn't have to wait around very long. He lost track of how long he was sitting on the boat, but eventually Cream stepped onto the deck from the pier. They stared at each other for a moment, each trying to think of something adequate to say to the other.
"Turns out she was a lesbian." Cream said flatly. Tails tried his best to not laugh at that. "She took me to some of her friends and offered to wear me like a hat."
Tails started giggling through his nose. He didn't know why he was laughing. What she said wasn't inherently funny. It was probably the combination of all the stress and then having that dumped on him just broke him.
"Thanks, Cream. I needed that." he said, doubling over and burying his face into the seat. Cream walked up and sat down next to him. "So why didn't you tell me you had a crush on me?"
"You found out?" Cream let out a sigh. "I'm sorry. I should have come clean with you. I just... didn't know if you were even interested in me."
"You're... interested in me, t-" Tails sighed in frustration. "God, we're both idiots. Cream... I really like you. That's... that's all there is to it, really. I thought you wouldn't be interested in me because I'm just some nobody engineer."
"You made an antimatter reactor and a fleet's worth of planes! Nobody else can claim the same thing!"
"So why were you trying to hook me up with another girl?" Tails asked.
"Well, like I said, I thought you weren't interested in me. In light of finding out, though... I guess I was testing you."
"Did I pass the test?"
"No, you failed miserably. Though, to be fair... I did, too." Cream sat down in Tails' lap, straddling his hips. Tails' heart skipped a beat. She was grinding into his crotch! What's more, she grabbed the bottom of her bikini top and pulled it up over her head. He already saw her breasts in her after hours shoots, of course, but seeing them in person, close enough to feel the heat radiating off her body, was a different experience entirely. She hit puberty only recently, so she was only a B cup; defined enough that they were more than slight mounds on her chest, but still quite small.
Cream pressed her chest into his face so her nipples pressed against his lips. At first, Tails thought it was just a coincidence, but then he realized what she was trying to convey and closed his lips around one of the teats.
"Mom and I do this from time to time." she explained. "She says it brings her to a boob orgasm. Think you could do the same to me?"
To Tails, it felt like all the blood in his body immediately rushed to his face. At first, he was excited that this was actually happening, but then anxiety quickly set in, and he was worried that he might not be able to please her. No... he could please her. He was in love with her, and he would do his best to make her feel good.
Tails closed his lips around one of her nipples and sucked on it gently. He pinched and flicked at the other nipple, which quickly erected both of them to rock hard tips. His cock pressed up against Cream's crotch, begging to be released from his shorts.
Cream shivered and held his head to her breasts. Her pussy lips tingled with arousal. She wanted so much to fast forward and get to the part where he plunged his length into her, but to get the most out of the experience, they had to take it nice and slow.
Cream's staggered breathing was a good tell that Tails' effort was paying off. He could feel a damp spot developing on her crotch through her bikini and his shorts, accompanied by a wave of intense heat like his cock was close to a hot oven. He was not nearly experienced enough to understand all the various physical changes that happened to a girl when they were aroused, and he never considered that could even happen. It made him ever more eager to bury his meat into her oven and feel her warmth at its source.
"Mmnn, I'm getting close!" Cream gasped. She reached between her legs and massaged her clit through her swimsuit. The nylon in the weaving rubbed against the sensitive love button and gave her that extra bit of push to go over the edge. Even though stimulating her clit is what caused her to orgasm, all the pleasure seemed to stem from her breasts. They went numb like her pussy lips whenever she massaged it to climax, which created an interesting sensation, to be sure. At the same time, it did nothing to slake her lust like a normal orgasm would surely have done.
"That... was intense!" she panted as she came down from her high. "So... do you wanna head back to the hotel and... join me?"
"Mm? No... no no, completely unnecessary." Tails gestured for Cream to get off his lap, and after he stood up, he grabbed her hand and led her downstairs, underneath the bridge, into the main cabin of the boat. The living space inside was larger than the outside would lead one to believe. There was a small kitchen to their immediate left as they went in, a closet on the wall next to the stairwell, a bathroom and shower room to the right, and directly in front of them, a queen-sized bed with neatly-folded teal sheets.
"I don't think Knuckles will mind if we borrowed his bed for a while, do you?" Tails pulled off his clothes and tossed them to the side. He looked behind him just in time to see Cream wriggling her butt out of her bikini bottom. Once again, all her after hours photos combined didn't compare to the sight before him now. His cock throbbed painfully with anticipation and stood out above the ninety degree angle.
The two climbed onto the bed. Tails laid down on his back and Cream sat down on his lap. His dick submerged between her butt cheeks and probed against her tail on the other side.
"This feels... so surreal." he whispered. Everything felt like it was a dream, but there were too many details he was aware of, from the warmth of her body, the moist heat radiating from her womanhood, the softness of her skin. Even though all the facts that this was reality was laid out bare for him, he still couldn't begin to comprehend that this was actually happening to him.
"Trust me, everything is as real as it can get." Cream assured him, moving her hips back. She dangled herself precariously on his manhood, applying miniscule amounts of pressure against it.
"Do... you remember that time when we had that tainted candy?" Tails asked.
"Y-yeah. Why?" Cream only partly remembered that night. Her mind was in a fog that night, and she didn't remember many of the details outside of Marine and Sally taking turns violating her with dildos of various sizes and shapes. It was a memory of... mixed emotions.
"Your mom mounted me, but the whole time... I was thinking of you."
"Hmm hmm... that's romantically cheesy." Cream teased, then slammed her hips down on his cock. Both of them gasped loudly and wrapped their arms around each other. It was many years since Tails got fucked by Vanilla, and his memory was clouded by the tainted candy, so he long since forgot how it felt inside her. Now that he was fully aware and sober, it was hot, tight and moist. It also felt like her insides were custom-molded to fit around him. He could also feel her labia kissing his pubis; the plump lips felt very nice and soft as well. There was nowhere else in the world he wanted to be than right here, right now.
Cream began to bounce up and down on his lap, setting a nice and steady pace for both of them. Tails gripped her by her firm, tight ass and helped her with her motions. Every motion downwards made her vaginal muscles contract around his member, but it wasn't painful. In fact, it felt very good, for both of them.
Cream leaned down to kiss Tails on the lips. It was an open mouth kiss, and their tongues clashed somewhere between. Her ears draped down over his shoulders and chest. She drew away, leaving a thin string of saliva between them.
Tails held her by her back and flipped both of them around so he was on top. He leaned over her and thrust his dick into her with incredible vigor. Cream wrapped her legs around his back, holding him close. Her pupils were dilated and her face was flushed a light pink.
"Mmn, Tails..." she moaned, pulling him into another kiss. Tails could feel his balls tingling as his orgasm neared. It took a lot of restraint to not try and fast forward to the very end. When he felt like he was on the verge of blowing his load, he stopped and flexed his Kegel muscles, trying to stop the flow. He felt like a small bit of spooge managed to squeeze past into his urethra, but he tried to ignore that feeling lest he lose control.
Once he calmed down a bit, Tails resumed fucking Cream. By the sounds she was making and the expression in her eyes, it was clear she was on the verge of her orgasm as well. He continued to thrust for another few minutes before he felt himself teetering on the edge again. This cycle continued several more times, each thrusting session shorter than the last, and each down time longer.
The very last one was only a few seconds long before Cream gasped and tightened her grip around him. Her vaginal muscles contracted around his cock repeatedly, and like a riptide, it pulled him closer to the edge and there was almost no restraint left in him to prolong it. Tails finished himself off by thrusting wildly into Cream. He gave her a deep, intimate kiss as he came. It felt like he dumped more volume into her than his balls could even hold. After the third spurt, he began to feel dizzy from the endorphin rush. It continued for what felt like several minutes. Cream's vaginal muscles contracted even harder, almost like her love canal was actually milking his dick of every last drop.
The two lay there, basking in the afterglow. When they came back to consciousness, they found themselves kissing and cuddling under the sheets.
"I... I love you, Cream." Tails whispered, placing his hands on her butt and holding her close. He was still inside her, only at half wood, but nonetheless enjoying how her soft warm insides embraced his member.
"I love you, too, Tails." she replied. "You know, I could talk to my agent about moving back to Mobotropolis. That way, you don't have to come fly out every time you want to visit and shag."
"That'd be awesome. You could move back into the castle. I bet Sally misses you and Vanilla."
"She does. Hey, maybe next time, mom could join us!"
"W-wait, what?!"
"She loves the young meat! Besides, I gotta make sure you two are compatible, too! It's just the rule mom set for me once I got old enough to have a boyfriend!"
"Heh, alright. But for the duration of this vacation, I just want it to be about us."