The Price of Losing

“Ivysaur, that’s enough come back!”

I activated my Pokéball and recalled Ivysaur. I may have been doomed, but that didn’t mean I had to let my trusted companion get mauled any further than she already had been.

The victorious Tentacruel hissed his anger at being denied his meal. His trainer just looked smug.

“Well, well, well. Not so high and mighty any more, are you?”

And with that, I lost any hope of getting out of this hair-brained bargain. It had seemed reasonable at the time. I thought I was the best. I figured that my grass-type team would let me waltz right through this gym, what with their over-reliance on water type Pokémon. The only problem was, I wasn’t allowed to even try. I was supposed to get a license and go in order. But I didn’t have the cash for that.

Andy had found me after I’d been ejected from the premise. He was a trainer there and told me that he could get me in to face the leader, legit, with a badge if I won and everything. But he wanted to make sure that I wouldn’t waste his leader’s time. So he’d proposed a little wager.

If I won, he’d give me ¥10,000 and let me face Misty.

And if he won…

Well, I didn’t have money. All I had was my body.

And for today, that’s what he’d be getting.

“Please Andy, just let me go. I’ll forget about this whole thing, never bug you again. Just… don’t hurt me!”

I backed away from him as I pleaded. I hoped he was willing to take some sort of mercy on me. I’d been overconfident, yeah. I may have made some boasts. But if I begged…

I feel down to my knees.

“I’m begging you. Please don’t do anything to me. I know I was cocky and you deserve to be able to tell everyone you took me down a peg, but can’t you just settle for that?”

Andy’s grin only grew. “I like the look of you on your knees. I could get used to it.”

Begging seemed to be a clear failure. Which left nothing but running. I jumped to my feet and made to turn. I heard Andy shout something. Before I could get three paces away, something wrapped around my ankle. I tripped and went down hard.

I took a moment to collect myself, before checking to see what had caused me to fall.

With dawning horror, I realized that it was one of Tentacruel’s eighty tentacles. I kicked and struggled against it, but it only wrapped itself more tightly around my leg. I tried to grab it and pry it off, but others quickly joined it.

Within seconds, half a dozen tentacles held me down. There was one for each of my limbs, one wrapped around my mouth, and one around my waist. I could barely wriggle. Screaming, running, even crawling, all of these were impossible.

Andy walked into view. His smirk was back in full force.

“I’m going to give you one last chance to play nicely. In a second, Tentacruel is going to let you speak. All you have to say is that the deal was fair and you’ll do whatever I ask. I’ll make it fun, we’ll both have a good time, then you’ll go on your way, no worse for wear.”

Andy paused for dramatic effect.

“Or, you can say no. In which case Tentacruel will hold you down and I’ll do whatever I want with you. I’ll have fun and you’ll go on your way considerably worse for wear. Which will it be?”

The tentacle receded from my mouth. I took a deep breath. Then I screamed “HEEEEELLLLPPPP!” as loudly as I could.

In retrospect, not one of the smarter things I’ve done. I deliberately chose an out of the way spot for the Pokémon duel. Which of course meant that there was no one to hear me scream and all I managed to do was make Andy angry.

The tentacle was back around my mouth in a second and my scream was cut off with a pained squeak.

Andy’s grin had lost all of its mirth. Now he just looked mean.

“Would you be so kind as to undress her, Tentacruel?”

I struggled against this, but it was pointless. Tentacruel had far more limbs than I did. Several worked their way under my shirt and pulled it over my head. I had hoped for a second with my arms free, but tentacles grabbed them below wherever the shirt was, then moved up as the shirt was pulled off.

My mouth did get free for a split second, but I barely go the chance to scream again before it was covered again.

“Flip her over!” Andy commanded, and suddenly I was facedown in the dirt. I heard his footsteps crunching towards me, then felt his hands on my back as he undid my bra.

“Take that off her too.”

Tentacles repeated the earlier process. I was left bare chested in the ground, with only the angle hiding my tears and embarrassment.

“Stand her up for me, would you please Tentacruel?”

Tentacles roughly forced me upright, standing just in front of Andy, my breasts on display. They rose and fell quickly with my panicked breathing.

He roughly pinched my nipples, until they were elongated and hard. I couldn’t even cry out against the pain, could only sob silently as I was held helpless in the embrace of his Pokémon’s tentacles.

“If common sense won’t make you cooperate, perhaps fear will.”

Andy took in my vacant expression and laughed a sharp cruel laugh.

“Tentacruel can choose to make its tentacles into stingers. Because I’ve wanted to convince you, I haven’t had it do that yet. But perhaps it’s time for me to show you what it will feel like.”

I tried to shake my head, tried to promise that I’d stop struggling, that he could do whatever he wanted with me and I wouldn’t try and stop him, but my head was held fast.

“Tentacruel, sting one of her nipples.”

A tentacle slowly emerged from the writhing mass of all of the others on Tentacruel’s body. Unlike the others, this one was covered in sharp barbs. They expanded and contracted to the beat of something I couldn’t hear.

The tentacle slowly drew closer to my left breast. I fought as hard as I could against my bonds, tried every trick I knew to break a grip, but I was held helpless and hoarse as the barbed tentacle approached me.

The tentacle touched my left nipple and I felt fire coarse through me. The pain was different from a fall or a slash. It felt like my nipple was dissolving, being pierced and seared by hot iron all at the same time. The tentacle around my mouth muffled my frantic screams.

Minutes later, the pain receded and all the tension slowly drained from my body. I stopped screaming and I felt like a marionette with her strings cut.

Andy was grinning at me.

“I bet you’ll be a lot more cooperative now. How about you be good and take off your shorts and your panties.”

The tentacles on my loosened, although one stayed wrapped gently around my mouth and another on my left arm.

Sobbing and nodding, I slowly unbuttoned my shorts and let them fall. A quick, embarrassed step and I was out of them.

I tried to pull down my underwear, but I just couldn’t make myself do it. I felt too embarrassed, too violated. Taking them off and exposing myself to Andy would be one step too far.

Andy saw my hesitation. He gave me a frosty glare.

“I’ve given you every opportunity. But you just won’t listen. This was your last chance to have things happen on your terms, your last chance to walk away from this. But you’ve been stuck up the whole time, so I’m going to make you mine forever. Tentacruel, strip her and force her to the ground.”

I was lifted up for an awful gut-wrenching second. I felt the tentacles slither around my panties and then pull them down, exposing me to Andy. Then I was slammed down into the ground, so hard that I lost my breath and all sense of where I was.

When I recovered, Andy was standing over me. He was naked and his cock was hard.

“I’m going to fuck you eventually. But Tentacruel deserves some reward first. Play around with both of her holes and get her ready for me, won’t you sport?”

He patted one of the tentacles affectionately.

There was a second of stillness, before the tentacles were all around me.

I tried to scream, but a tentacle still blocked my mouth. And all my struggles were pointless, covered as I was in layers of them. Tentacruel loomed over me and I felt lost in the sea of tentacles and his large red jewel. I heard a humming just outside of my hearing that set my teeth on edge.

After a few seconds, the tentacle’s activity mostly stopped, with all but three falling quiescent. One tentacle covered in suckers was slowly grabbing my unhurt nipple, pulling it to extend it, then letting it free. The nipple was rapidly hardening and the sensation felt shockingly good.

Another was slowly working its way inside of my ass. It had shrunk down to a size that didn’t make it hurt, but that didn’t stop it from giving me a sensation of fullness that I fought against but couldn’t prevent.

A third was stroking the lips of my vag.

After the second tentacle firmly lodged itself in my ass (was it expanding?), the tentacle playing with my lips became more active. It parted my folds and pushed inside of me a bit, before withdrawing. Then it found my clit and stroked it for a few seconds, drawing an involuntary gasp and a whimper.

I wanted to be terrified, but there was something comforting about all of the tentacles around me. I was held fast, but with the fullness in my ass and the pleasure on my clit (and it was real pleasure now, as the tentacles found my rhythm and I ground involuntarily against them). I tried to fight against it, but I couldn’t see the point anymore. I was just so confused and the tentacles inside of me felt so nice, filling me up and making me feel better than any boy could. I could feel an orgasm coming. A few minutes of this and I’d be gushing onto the dirt. I didn’t even care about the embarrassment.

The tentacle stroking my clit withdrew. I whimpered in complaint. I had gone from struggling to compliant and I didn’t know why, I only knew that there was a confusing, soothing hum in the air and that I wanted the tentacle to be touching me.

Tentatively the tentacle returned, but this time it was pushing its way inside of me. It pushed just an inch in at first, testing the waters and finding me soaked and inviting. It withdrew all the way out, before slowly pushing itself back in, a bit deeper.

My hips arced to meet it and I couldn’t stop them.

The tentacle pushed deeper with each stroke, until it was filling me up all the way. Then it began to expand. It was pushing against my walls, giving me every last possible shred of pleasure and I loved it. I pushed into it, I moaned freely and discovered that my mouth was free. I didn’t want to call out anymore. I didn’t want this to ever stop.

There was a delightful feeling of fullness, whenever the tentacle was buried in me. Both of my holes were stuffed and the tentacles held me tight. I couldn’t ever remember feeling this comfortable.

Even seeing Andy looming over me couldn’t ruin my feeling of contentedness. He was stroking his cock and I couldn’t help but idly wondering how it would feel inside me as well.

He crouched over me and forced it into my mouth and I didn’t complain or fight. I accepted it into my mouth and stroked it with my tongue.

I could hear him speaking, but his words meant nothing to me.

“You used supersonic or her, didn’t you? Well done Tentacruel! I thought we’d have to torture her and break her the old fashioned way, but this will be much more fun.”

The words were so confusing better just to focus on the feeling of the tentacles, deep inside of me, or the tentacle that was now gently stroking me clit, or the interesting feeling of the cock in my mouth. There were so many fascinating things to feel and I was lost in the feeling of them.

Andy moved quicker and quicker, his cock going into my throat. I gagged a few times, but I was only dimly aware of the fact. I tried to keep up with him, tried to lick him and keep my mouth available. It felt nice to be used. It felt nice to have another hole filled.

Andy said more words, but I couldn’t understand them. They didn’t even register.

Suddenly he was withdrawing from my mouth and the tentacles were withdrawing. They must have been bad words, words that heralded the end of my pleasure.

Before I could complain or cry, Andy lying on top of me and I felt his cock slip inside of me. It wasn’t as filling as the tentacle had been, but it was harder and curved and it pushed up against my insides in a way that felt interesting and new. His lips found mine and I kissed him greedily, opening my mouth to his probing tongue.

The tentacles had released my arms and I wrapped them around Andy, pulling him close to me so that he couldn’t get away or stop. I pushed up into each of his strokes and I felt the tentacle in my ass supporting me, helping me to push up into him.

There was a pressure building inside of me that didn’t come from the tentacles. I couldn’t really remember the word for it, couldn’t remember what it meant. All I knew is that I wanted to feel it and feel it soon. I had to tell Andy so he could make it happen. The word has just on the edge of my consciousness. What was it, what was it?

Come.

“C-c-c-ome?” I managed to stammer out.

“She’s begging us to come Tentacruel. How about you help her out with one of your tentacles?”

I felt a tentacle slide between my body and Andy’s, but it didn’t separate us. Instead it latched onto my clit and began frantically flicking it. I redoubled my efforts to fuck Andy, pushing myself up into him as frantically as I could.

The pressure inside of me was building, growing to the point where I couldn’t think about anything but it. I was moaning now, moaning desperately. I could dimly hear Andy moaning too, and swearing on top of it. His words hardly registered on top of my mountain of bliss.

“Fuck she’s horny, fuck, fuck, fuck, I’m coming, I’m coming!”

I couldn’t even try to parse it because fireworks were exploding behind my eyes, no, wait, everything was exploding, all I could feel was pleasure, radiating from the tentacles and from the cock buried inside of me and twitching to a rhythm I couldn’t understand.

I couldn’t breathe; I couldn’t do anything but moan, one long continuous moan as the pleasure overtook me. I ground frantically into the cock, into the tentacles, I pulled Andy as close to me as I could. I need to hold on to him, there was too much pleasure it was too intense and I was drowning.

For an endless moment, a tiny eternity, I was completely helpless.

Slowly, the pleasure receded.

Slowly, I came back to my senses.

Andy was sitting up next to me. My hands and legs were still pinned down by Tentacruel. The fear tried to reassert itself in the pit of my stomach, but the calming buzz started again and confusion replaced the fear.

Andy smiled at me.

“You did well pet. I think I’m going to extend our deal quite considerably. I’m going to train you to be the perfect toy. And I think you’re going to like it, won’t you?”

Words were difficult, but I managed to stammer out: “will you always make me feel like this?”

“If you’re good.”

The decision was easy to make despite the fog clouding my brain.

“I want you to teach me how to be good then.”

Andy smiled at me. The tentacles began to tease my skin again. And slowly, Andy began to explain my new life to me.

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