The First Time

Story by Kinky Chameleon on SoFurry

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Diego has been planning his perfect bondage fantasy for weeks. All he needs now is to get his classmate Huan into it. But he might be in for a bit of a surprise!


Diego had to stop himself from yanking the front door open the second he heard the doorbell ring. He took a deep breath, counting slowly from one to ten. Then, when he was sure that enough time had passed to make it seem like he hadn't been waiting by the door, he turned the handle and tried to open the door casually.

"Hey, Huan! Come in, please." He took another deep breath as the lithe fennec fox female stepped into his front room. She was dressed casually in a T-shirt and jeans, nothing particularly sexy. Well, he'd have to fix that.

"Thanks. I should have worn a jacket. It's colder than I expected." She smiled at him, her huge ears tilting in just the right way to make him feel like his intestines had melted together. Keep it together, Diego, he thought to himself as he led her inside. You'll have plenty of time to look at her once everything is ready.

Of course, Huan didn't know why she was here. Not yet. It had only been a week prior that the grey wolf boy in her World History class had started talking to her. Diego had been planning this day for at least a month, picking out the right girl, figuring out what she liked, running the conversations he'd use to get her attracted to him over and over in his head. And now the fact that everything was almost in place was causing sweat to soak into his forehead fur.

He'd managed to lead her to the end of the hallway before she spoke up. "Um...so, can you tell me why you invited me over now?"

Diego smiled in a way that he hoped was confident instead of terrified. "It's like I told you before. I want to show you something."

"Yes, but...what exactly?"

"It wouldn't be a surprise if I told you now, would it?" He attempted a teasing wink, but in his nervousness his other eye closed at the same time. Ugh, just hurry up and do this before you mess everything up!

Trying his best to be suave, he reached forward and opened the doorway to his right. A cool puff of air ruffled their fur as a narrow stone stairway came into view, leading down into what was currently a blob of darkness. "The light switch is at the bottom," he said, gently taking her paw in his own and starting to walk down the steps. To the credit of his work over the past week, she only hesitated for a moment before allowing him to pull her along.

For a few seconds, the two of them stood at the bottom of the staircase in darkness. He'd spent calm, boring afternoons trying to decide how to do the reveal. He'd settled on showing it all at once, but then he'd deliberated about how to do it. Then, we he'd chosen a dramatic flip of the light switch, he'd agonized about how long to wait in the darkness. Of course, now that it was really happening, his paw was shaking so bad that he missed the light switch on his first try. A couple seconds later, he managed to flip it on the second try.

He blinked in the sudden electrical light, focusing his attention on Huan's face before anything else. He watched her eyes adjusting, followed by her taking in the contents of the room. He felt a surge of joy as her mouth dropped open and her eyes widened in shock, so much so that he couldn't help turning to look at the room, even though he knew exactly what he'd see.

In front of them, laid out so carefully that it could have been a magazine photo, was a giant basement that had been transformed into the perfect sex bondage dungeon. Diego still felt a chill running up his spine every time he looked at it, even after working on it for so long. He'd been curious about BDSM for years, and when his parents left on a business trip for a few months, leaving him with an allowance that most kids would salivate at, he'd known exactly what he wanted to do.

Along the walls, dozens and dozens of bondage toys of all shapes and sizes--from whips to ball-gags to rope--hung from hooks, reaching from the floor to the ceiling. The main bulk of the room had been stuffed with whatever furniture Diego could find on the internet: a bed, several tables, a cage in the corner, an assortment of bondage chairs, and even some harnesses hanging from the ceiling. Every item was laid out with care and precision, nothing even an inch out of alignment. The entire room felt like it was crouching down, unused but waiting for the first opportunity to pounce on an unsuspecting victim.

Diego licked his lips and cleared his throat. He'd gone over this day a dozen times in his mind, rehearsing and perfectly exactly what he would say and do. But in none of those personal simulations had his blood felt like rivers or ice or his bladder like a balloon about to pop, despite the fact that he'd just used the restroom a half hour ago. Already his nerves had ruined what would have otherwise been a perfect fantasy...he couldn't let himself ruin this chance!

Luckily, Huan still hadn't said anything, or even moved from her position at the bottom of the stairs. The only movement was from her giant ears, the fluffy tan fur bouncing as they tilted back and forth in a frenzy. Odd...I've never seen them do that, Diego thought. But he'd wasted enough time...he still needed to finish springing the trap. Doing everything in his power to stuff down his nervousness, he stepped forward, looking around the room and gesturing like a grand businessman showing off his customized office space. What was that speech he'd prepared?

"I-I imagine that you're feeling a little bit overwhelmed, Huan, so let me explain. You see, many people find that a regular romantic life to be...shall we say boring? Some need a bit of extra spice to brighten up their relationships. I'm one of those people. For me, finding innocent young girls and teaching them the ways of submission is a particular delight."

He glanced back at Huan, who still showed no signs of reaction, then reached up, running his right paw along the implements hanging from the walls as he continued. "I brought you here because I think that you'd make an excellent little slave for me. I've been watching you closely, and I know that you crave to be shown your place, even if you don't know it yourself. You crave to have your freedom taken from you and be forced to submit to a strong, virile wolf like myself.

"You don't have to worry, though. I know that this is all new to you, so I won't use my most...intense toys on you right away. We can start slowly. Perhaps just a few ropes to get you situated, and then we can--"

A soft metallic clicking sound interrupted Diego's diatribe. He blinked, his ears twitching towards the noise even as his fur registered a strong, encompassing pressure. When he glanced down, he saw that his left arm, which he had been holding behind his back in an attempt to look like a gentleman, had been given a metal bracelet around the wrist. His eyes flicked up to Huan, whose paws had just finished carefully fastening the handcuff link around his left wrist.

"What are you--" he began in a stupor of thought, but before he could finish, Huan had swooped forward, wrapping her arm around his shoulders and planting a kiss directly on his muzzle. He felt the heat rising to his cheeks as his tongue was wrestled to the bottom of his mouth by her own. He'd imagined his first kiss to be something like this...and yet nothing like this!

After a few seconds, Huan pulled back, a knowing smile on her lips. Diego tried to reach forward for another embrace, but he found his arms pinned behind his back. The horror reached his eyes at the same moment as the realization that his paws had just been cuffed behind his back.

"Honestly, Diego," Huan said with a flick of her ears, "do you think I'm eleven years old or something. I know what BDSM is."

Diego just stared at her for a few seconds, his mouth opening and closing as he tried to find words to say. This had suddenly gone from a carefully planned fantasy evening to an unexpected and uncontrolled situation, and his brain was trying to adjust to being off script. "Wh-Why did you do that? Unlock these handcuffs already!" He winced, knowing how pitiful he already sounded.

By now Huan had wandered over to one of the walls and was casually examining several of the lined-up items. "You certainly seem to have put a lot of work into this. But...well, let's just say that the drama club didn't miss a member in you. It was obvious from the first word out of your mouth that you've never actually done any of this before." Her slim paws unhooked something metallic and cage-like from the wall, the straps hanging down in the air.

Letting his legs do the thinking for him, Diego attempted to dart for the stairs, but he'd only made it a couple of steps before he was pitching forward, slamming his face and chest painfully against the thinly-carpeted floor. Huan sighed, withdrawing her leg and moving forward, straddling the boy on his back. With seemingly practiced hands she brought the metal muzzle around and shoved it over his nose and mouth, tightening the leather straps around the back of his head. The cage was small, barely squeezing over his face, and there was absolutely no room to open his jaw. His attempts at yelling for the girl to release him only resulted in a few garbled mumbles.

Huan stood up and dusted off her paws, looking satisfied to herself. "And what, did you think I was just going to blush and wilt and submit to whatever you said, just like that. You've been reading too much fantasy porn. Well...maybe just the wrong kind of porn."

"Mmmfffff!" Diego shouted, trying to pull himself up to his knees. His handcuffs were making that much, much harder than he'd imagined. Then again, he hadn't really imagined being on this side of the handcuffs. When he'd had a plan, he'd already been nervous and twitchy. Now, when his plan had been totally shredded, he found himself in a haze of panicked thoughts and inability to function.

The fennec fox, on the other hand, was moving with the confidence that Diego wished he could have been showing earlier in the evening. After giving his T-shirt a few experimental tugs, she grabbed it with both paws and tore in opposite directions. The thin fabric didn't put up much resistance to her paws, and a few seconds later he could feel the cool air rubbing against his bare, furry back. He let out a complaining growl at the loss of one of his favorite shirts.

Huan didn't seem to be paying any attention. Tossing the remnants of the shirt to the side, she reached around his waist and unbuckled his slacks. With a determined yank, they came all the way off of his legs, leaving him with just a pair of white cotton briefs on, his sagging tail poking out of a hole in the back. He could feel his fur standing up on end and his face flushing a bright red! He was sure that it couldn't get worse than this.

His scream of surprise into his muzzle flared out as Huan showed the same determination in seizing and yanking down his briefs as well, leaving him completely naked! I wasn't going to undress her all the way! This is completely unfair, he found himself thinking, above more pressing concerns. He felt her hands wrapping around his waist (in a way he would have craved for in different circumstances) as she turned him face up, exposing his complete nude front to the ceiling.

The fox tilted her head a bit, a smirk playing on her lips. "You know, that might be a decent default size, but the fact that you're rock hard right now is definitely a turn off."

Diego blushed more, mumbling excuses into his gag. To have the frail fennec fox he'd courted so carefully standing over him and mocking the size of his junk was almost too much to bear. For the umpteenth time he attempted to free his paws, but the cuffs were on tight, and made of a material that he couldn't break with his own strength. He should know, as he'd bought them specifically for that purpose.

Okay, she's humiliated me. Now she'll let me go, right? The boy felt his hopes surging as Huan helped him roll up onto his knees and then to his feet. She was a lot stronger than he'd thought. But instead of the welcome feeling of his handcuffs unclicking or his muzzle straps loosening, he experienced a stumbling discomfort as the fox pushed him forward, holding onto his trapped paws as leverage. In a few steps, he found himself pushed up against the end of a sturdy wooden table, carefully chosen for its strength and height.

So many times he'd pictured himself in this scenario, but never had he thought he'd be looking through this pair of eyes! Huan forced him to bend at the waist, pressing his naked chest against the rough wood. His face and muzzle were pressed downwards, limiting his vision of what Huan was doing. In no time at all, he felt soft, thick rope being wrapped around his body, tightening him against the table. Damn, she's fast!

Next, his left leg was jerked outwards and tied expertly to the table leg, followed by his right leg on the opposite side. He tried to wiggle, but the ropes didn't offer any give, and the knots didn't seem to be within reach no matter how he twisted. His butt had been forced into the air by the position he was in, his cheeks spread. His cock had been forced to point downwards, trapped against the edge of the table. Why was he feeling so aroused right now? Shouldn't he be flaccid with terror?

Diego spent the next few minutes squirming helplessly against the table and murmuring into his muzzle incomprehensively. He had just started to worry that Huan had just left him there when the slim fennec fox stepped in front of the table and into his view. She still had that smirk plastered across her face, as if this was all just a silly joke.

She shook her head at his garbled attempt to plead for mercy. "You haven't learned your lesson yet. You expected me to be your slave just because you asked. But you don't know what it feels like to submit completely, to feel all of your pride being replaced by shame, piece by piece. Not yet."

What else can you do to me?!, Diego wanted to scream. He'd been stripped, tied up in a humiliating position, and mocked ceaselessly. Yet Huan was still acting like she hadn't even started yet! What could she be planning?

The sound of something heavy dragging across the floor made his ears splay in fear, though he wasn't sure why at first. He quickly did a mental list of the room's contents, trying to figure out what she could be moving around. The bed was probably too heavy, the chairs were pointless since he was already tied up, and most of the other stuff was light enough to carry. He only remembered what she could be moving into position when he felt the tip pressed against his rear end.

It had been his last purchase, and he'd debated for a long time about whether to send for it. It was extremely expensive, for one. Plus, what was the point of a machine that did the fucking for you when the whole point was to enjoy her yourself? Eventually he'd given in, reasoning that it would be a good way to keep a slave horny and stretched when he needed a break.

The Thrustcock 400 was a large metallic device steadied on four legs. It had a heavy engine and complicated system of pieces to make the dildo at the very front plunge in and out at varying speeds and pressures. It had come with several different dildo sizes, but Diego could already tell that one pressed against his tail hole was the largest.

"MffffmffffffmmMMMFFFFF!" Diego shouted, trying to appeal to any kind of mercy from his tormenter. Either she didn't hear him or wasn't listening, because in a few seconds the Thrustcock 400 groaned, electricity pouring into it. His entire body tensed as the dildo slowly began to push forward, pinning his body against the table. He groaned in horror as his asshole slowly and painfully bent around the incoming dildo, his cheeks widening from the pressure. Each thrust hurt, but only because it was getting deeper each time. Already he could feel himself getting used to the massive length plugging his rear end.

There were several times that he was sure that the dildo had reached as far into him as it could possibly go, only for a new barrier to be broken and it to slide even further inside. He coughed with discomfort, his entire body feeling like it was being filled up with an expanding balloon. This is supposed to be fun? He knew that some gay couples did anal sex, but he couldn't see why being on the receiving end would be anything but--

Diego's entire body sagged against the table as the dildo suddenly reached a special spot inside of him. The stroking against his prostate was a feeling more intense than any other he had ever had. The pleasure caused his mind to swim, his eyes to roll back, his ears to perk and his tail to wag against the machine piercing him. He felt a little squirt as pre-cum began to ooze out of his cock at a rate he'd never witnessed. All the times he'd pawed himself off, he'd never even gotten close to this level of ecstasy!

Time itself seemed to slow down around him. He found himself moaning with pleasure, actively pushing against his bonds--not to try and escape, but to grind his prostate against the dildo even harder! The speed of the thrusts was increasing. He was panting and drooling from two orifices, somehow both completely ashamed of how he was acting and desperate for the feeling to keep going.

He knew he was getting close to what would be the most intense and amazing orgasm of his life. His cock twitched in anticipation, and he let out a howl as he felt the climax approaching. But suddenly there was a sucking sensation, and the feeling of being plugged was diminished. The dildo was being pulled out! He cried out, desperately attempts to shove his asshole back onto its perch, but it was no use. The machine popped out of his body, and the mounting pleasure of climax suddenly dissipated. He groaned in pain and anguish, his ruined orgasm leaving him with nothing but a sweaty body and a small stain of precum on the floor.

He felt a soft paw ruffling his ears a bit as Huan appeared in front of him again. For a few seconds she just stared down at him with a smile. Diego wished that he could press himself into the floor and just disappear forever. This girl had taken his clothes, his movement, his voice, and now even his ability to pleasure himself. He was completely under her control. But much, much worse was the fact that he knew, he knew, that he had been happier than he'd ever been for just a few seconds.

Huan nodded, looking satisfied. Then, without saying a word, she turned and walked towards the staircase, beginning to climb up. Diego was so exhausted and spent that it took him a few moments to realize what was happening. He screamed at the top of his voice through the muzzle at her, wiggling helplessly in the bonds that she'd left him tied in.

Her ears flicking ever-so-slightly, Huan turned her head around to look at the naked, tied-up boy on the table. Then, with a wicked grin on her face, she shrugged her shoulders. "Sorry, Diego. I'm not really into bondage."

She flicked the lightswitch off as she climbed out of the basement, leaving him in complete darkness.