Tails' Summer Experience/Sally
Index
"So what do you think those two crazy kids are up to right now?" Vanilla asked Sally as they perused through the lingerie store. They were pretty much the only people here aside from another couple and some young teen girls. The place smelled lightly of perfume, which helped to drown out the salty scent of the ocean only a few hundred feet away.
"Back at the hotel, shagging in one of our rooms?" she replied. "Nah, probably not. Tails is too skittish to even ask her out, much less invite her to bed. I'm actually surprised nobody has swooped in sooner."
"Oh, they have. Cream didn't get too far with them, though. They barely got to second base with her before she broke it off."
"That bad, huh?"
"Well, Spike wasn't too bad. Sten was, though! Cream was infuriated after she broke up with him over how he treated her!" Vanilla picked out a camisole from one of the racks. It was a powder blue, and in the breasts of the lingerie, there were vertical folds in the fabric where the partner could stick their hand through to grope the breasts directly. "Ooohh, this is a good one!"
"I like it! You could wear it with this!" Sally held up a harem girl thong with small gold chains dangling from it. The crotch was bare, but was covered by a strip of cloth like a loincloth. "I'm buyin' this one, by the way. Lemme see if I can find another. So Cream is single now?"
"Yeah. Why do you ask?"
"I was just thinking that they might get together. At least, that's my hope, if you don't mind me saying."
"I don't. That actually sounds adorable!"
"There we go. This one should be your size." Sally handed Vanilla a thong similar to the one she found earlier. Vanilla checked the tag to confirm it was the right size for her. "Ready to check out?"
After they paid for the lingerie, Sally and Vanilla left the store and went to return to the hotel to drop off their purchases. Their intention when they arrived back at the hotel room was to fuck like wild rabbits, but when they opened the door, they found Tails laying down on the bed, looking very depressed.
"Oh... snap." Vanilla whispered. "Looks like that's our plans shot."
"Nnhh, I'll talk to him. We'll meet up later, yeah?" Vanilla nodded her head and left the room, closing the door shut behind her. Sally walked over to Tails, dropping her bag at the foot of the bed before sitting down next to him.
"Hey, Tails. What happened?" she asked, placing a hand on his forehead.
"Phuuuhhhh... it didn't go so well." he mumbled. "She tried to help me find a girl, but they weren't interested, and then before I knew it, I was cast to the wayside when they found out who she was."
"Aww, that sucks!"
"I don't even know why I agreed to come here." Tails pouted. "I'm not super charismatic like you or Sonic. Most girls are just gonna pass me up."
Sally scratched him behind the ears. She couldn't help but feel like this was her fault, putting him into a situation where he had almost no experience and expecting him to hit it off well with some random girl. He didn't make a move on Cream, or vice versa, so it was possible they just weren't interested in each other. Sally felt conflicting emotions about what she was about to do next. She always thought of herself as some combination of surrogate mother, older sister, and aunt to Tails. They had no blood relation, but with the history they shared, they might as well have. She sometimes felt some intimate affection for him on account of her wild libido, but she never acted on them. Until now.
"Uaah! Sally, what are you doing?!" Tails exclaimed as Sally threw her leg over his stomach and straddled his body. She smiled at him briefly before leaning down and kissing him on the lips. Her breasts pressed into his chest, and her arms snaked underneath his and wrapped around his back. They locked together to hold him in a tight embrace that he couldn't escape from, not that he would have wanted to.
They continued to kiss each other. Tails' cock grew erect between Sally's legs. She could feel it press against her crotch, eager to plunge into her. Sally broke the kiss and sat up on his lap. She reached behind her neck and unclasped the bra straps, letting it fall off her body and onto his chest. He saw her naked before, but in the current context, they held a whole new intimate meaning to him. It was at this point that Tails saw Sally in a different light. She was more than a caretaker to him now.
Sally tugged at one of the strings to her string bikini, which unravelled easily. She removed the bikini and allowed Tails to take in her beautiful, well-toned body in all its splendor. His cock stood up against her stomach, throbbing violently in his swimsuit and begging for her attention. He was a good six inches; a modest size, considering his age. Tails' face was bright red, and even though he was too embarrassed to say anything, it was clear from the look in his eyes and his pulsing member that he wanted nothing more than to explore her insides.
"S-Sally..." he whispered as she pulled down his swimsuit. Small globs of precum oozed out of the tip of his uncut dick. Sally moved off Tails' lap and cuddled up next to him, holding his face close to her breasts as she gripped his cock and began jerking him off. Tails' hips trembled and he pressed his head into her chest. It had been so long since his encounter with Vanilla, he forgot what it felt like to get handled by someone else. Jerking himself off was nothing compared to this! The way she handled his dick, the alien touch and the unpredictability of it made his skin tingle and his heart race like it wouldn't if he was doing it himself.
Tails reached down between Sally's legs and prodded and poked at her folds. He was surprised to find out that she was radiating an intense heat from her pussy, almost like he held his hand up to an oven. Digging his fingers into her love canal, he expected the flesh to be unyielding and tight as a drum, but she was pretty soft and malleable. When his fingers moved around inside her, Sally's vaginal muscles clamped down around them and conformed their shape to that of the foreign entity, and didn't allow much more movement besides.
"How does it feel?" Sally asked him. Tails almost didn't hear the question, he was so fascinated by her pussy. His breathing was shaking, and he could feel his heart pounding in his chest.
"It's so... soft and warm." he panted.
"Do you want to be inside me?" Tails tried to say yes, but he couldn't find the words, he was so anxious and excited. He simply nodded his head. Sally released his dick and rolled onto her back, spreading her legs apart slightly. "Then come on, stud muffin. I'm all ready for you."
Tails moved himself between her legs. He tapped his dick against her entrance, which was nearly enough for him to blow his load all over her pussy and abdomen. The only thing that stopped him was sheer willpower and the desire to make her feel good as well. That last plunge into her was a most difficult movement to make. The head was already spreading apart her plump folds. All he had to do was move his hips forward ever so slightly, and he'd be all the way up to the hilt inside her. Why was this slight movement so difficult to make?!
Sally smiled and was at first content enough to watch him muster up the will to push all the way into her, but she got impatient after a few minutes, and decided to help him out. Her legs wrapped around his waist and locked together as she pulled him in. Tails' eyes widened briefly before he doubled over, burying his face into her chest and letting out a cry of shock and pleasure. Sally wrapped her arms around him again and scratched the back of his head.
"There we go. Doesn't that feel much better?" she asked. When Tails had sex with Vanilla six years ago, he didn't remember having this problem. Maybe it was because he was drugged at the time, but back then, he at least had the endurance to last a few minutes before he felt like he was about to cum. Only a few seconds inside Sally, and he felt like he was going to go off like a broken fire hydrant.
"HAAAUHHH!! S-SALLY!" he exclaimed, holding her tightly as he tried to contain himself. Somehow, he managed to hold himself together, though he felt like he was on the verge of an orgasm powerful enough to generate lift. Tails lifted his head up from her heavenly bosom to stare at her in the eyes. She had a light blush across her face from her own arousal. He scooted up onto his knees so he had the ability to move himself, and leaned forward to give her another kiss on the lips.
"I-I can do this." he said. "I'll make you feel good!" He began slowly thrusting in and out of her. Her muscles contracted around his dick like they did with his fingers. He was sober this time, so the pleasure and intimacy was all the more intense. Everything about it was incredible. The feel of Sally's warm fur, her hot clenching vaginal muscles, her arms and legs holding him close to her body. There was nowhere else in the world he'd rather be.
"Keep going, stud." Sally cooed into his ear. "You're making me feel good." Tails was spurred on by her words of encouragement, and he quickened his pace. He made cute squeaking noises with very thrust into Sally. Both his tails twitched and flicked back and forth. The thick, ridged head of his cock brushed against her G-spot with every pass, building up a volcanic heat in the core of her abdomen.
Suddenly, Sally felt something at the base of his cock slowly expanding. It pressed into her labia, spreading out the lips further than she anticipated. She cocked her head to the side and looked down between his legs at his dick. To her surprise and joy, he had a delicious-looking knot. The various guys she had been with over the years - from Geoffrey, Knuckles, Sonic, her brother Elias, and sometimes even Shadow - none of them had knotted cocks, and she always wanted to feel the real thing. Now was the perfect opportunity to experience it.
Once Tails' knot fully formed, he subconsciously attempted to push it into her. It doubled the girth of his dick, which made it a bit more difficult to pop it into her. She wasn't about to tell him to take it slow, however. She wanted to get stretched out by the knot!
"Uuhahh! Sa~lly!" Tails moaned as he slammed the knot against her entrance. When he finally developed the insight to realize that wasn't working, he switched to a humping, grinding motion. This method turned out to have a much greater effect. Slowly but surely, the knot pushed apart Sally's pussy lips. She winced as she felt a slight discomfort. She took some pretty thick cocks and dildos before, but the additional knot made it a bit thicker than what she was used to. After a few more minutes of pushing and grinding, Tails' effort finally paid off, and he suddenly jerked forward an inch as his knot popped into her love canal.
Both of them let out a gasp of surprise and intense pleasure. There seemed to be ten times as many nerve centers in the knot than anywhere else on Tails' dick, and Sally enjoyed how it spread her insides apart.
"Nnghh! I c-can't pull out!" he gasped.
"Don't worry about it! Just keep grinding into me! I'm so close, Tails!"
Tails continued to grind into Sally. The pleasure was so intense at this point, it put his head in a fog, where he couldn't think straight, and the only recurring thought he had was to cum inside his mate.
Sally's eyes rolled in the back of her head when she came. Her vaginal muscles contracted tightly around Tails' cock and held him in place, even though the knot wouldn't allow him to pull out, and that was if he wanted to. Tails doubled over and whimpered. His cock throbbed violently inside Sally as he blew thick creamy ropes of jizz all over her insides. Sally's eyes widened when she realized just how much he was shooting into her. She'd definitely need to get her womb safeguarded by NICOLE again or she'd get pregnant for sure!
Tails collapsed on top of her, breathing laboriously. He wrapped his arms around Sally's body and nestled his head into her bosom. Sally rested her head back on the pillow and gently stroked the back of the boy's head. She considered what to going forward. Would Tails see her as his lover from here on out? She did love him as she would love a sibling or her own son, if she had one.
Sally wouldn't mind adding him to her list of cocks alongside Geoffrey, Sonic, Knuckles and Elias, but what if he wanted their relationship to be more than friends with benefits? She didn't want to break his heart, but with their age difference, that kind of relationship might not work out so well. Maybe what he wanted and/or needed was a confidence booster? Maybe if he got to fuck her on a regular basis, it would improve his confidence with girls? It wouldn't hurt, and at the very least, he'd be putting that wonderful canine cock to work.