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Training Emily - Taking Toys

By SassyinCali​(sub female)     May 5, 2023
I push open the heavy door and the room looks the same as last time. I stand in the middle of the room and wait for Professor. I should start wearing a watch since he takes my phone and I never know what time it is. Maybe that’ll be the first thing I buy myself once I am done paying Amber back and have my bills on track. The door opens behind me, and he enters the room. His shirt sleeves are rolled up.

“I need you to pay close attention to what I say and think before your open your mouth and react. Do you understand?”, he says sternly.

My stomach drops, this can’t be good.

“Okay, I understand.”

His jaw twitches, but he does not say anything. He walks over to the thing that looks like a vaulting horse that he spanked me over. He presses a button, and it lowers. When he stops it is at a height where I can easily sit on it. It annoys me that he made me struggle to climb up on it last time.

He opens a box that I had not noticed on a nearby bench. Inside are a bunch of dildos. Oh fuck! I don’t like where this is heading. He pulls out one of the fake cocks and attaches it to the padded vault beam. It stands obscenely erect. He turns to me.

“You will straddle this and ride it. For every toy you take in your pussy, I will add to your pay. This is only a five-inch toy, you should have no problem taking it in. You’ll ride each cock for five minutes. You may not cum. You’ll get $100 each for the five and six-inch toys. You’ll receive $150 for the seven and eight-inch toys. If you take the nine-inch toy in your pussy, you’ll get $200. If you want more money, you will take the toys in your ass as well. I can put a three-inch or four-inch on here for your ass if you want to try it. You will get higher amounts for the toys you take in your ass.”

“I’m not taking anything in my ass! You can forget about that!”

He watches me and I wait for him to deduct money or something, but he doesn’t.

“That’s your choice…today. You will take up to the seven-inch cock in your pussy today. You take them willingly and earn money. Or I will happily force you to take them for free. If I force you, I may continue to use bigger toys if it fucking amuses me. Don’t test me, young lady.”

His tone is quiet, but fierce. I bite my lip to keep from responding, I have no doubt he would force me and then send me home without any money.

“Now, straddle this toy and take it in your pussy. I’ll tell you when the five minutes is up.”

“Um…do I get lube?”

“No, either suck on it to wet it or figure out how to get your pussy ready. You only get lube for your ass.”

“You want me to suck a fake cock too? I just sucked yours!”

He steps closer to me, and it takes everything inside me to not step back.

“I don’t care if you fuck the toy dry. Now, take the fucking panties off and straddle the toy. I will not tell you again.”

I’m trembling as I remove the panties. I cross to the toy and touch it. I lean forward and take it into my mouth and try to get as much saliva on it as I can so it will not hurt entering me. My jaw is sore, and my lips are tender from earlier. I straddle the vault and line up the toy with my opening. I part my lower lips and press down. It has been a long time since I have had sex and it is uncomfortable at first. I really do not want to do this. But I know he will force me if I don’t and then I get no money. I slowing take more inside myself. I rub at my clit to try to get myself wet. It slides in and I adjust to it quickly.

“Now ride it, your time starts now.”

I rotate my hips and move up and down on the toy. It is uncomfortable at first, but I start to feel it rubbing against me and I feel myself become wetter. I close my eyes and imagine it is my ex-boyfriend’s cock that I’m riding. It’s not so bad after a couple minutes.

“Time’s up.”

I lift myself off the toy. He detaches it and hands it to me.

“Suck it clean and then put it in that bucket over there so it can be washed.”, he commands.

“I’m not going to suck it! It will taste like me!”

He attaches the next bigger dildo. He moves to me, holds the back of head firmly and takes the toy in his hand.

“Open your fucking mouth now!”

I try to push him away from me. He pulls me roughly to the ground and uses his weight to pin me between his thighs. He wraps his hand around my neck.

“Open your mouth and clean the toy. You’ll be tasting your pussy juices often! Fucking get used to it!”

He squeezes my neck tightly and I feel like I cannot take a breath. I open my mouth and he pushes the toy roughly into my mouth. He fucks my mouth with it hard. Tears form in my eyes and start to pour down my face.

“Suck it and lick it clean!”

I suck and lick at the toy. The taste is not as bad as I imagined. It does smell like me and silicone. But it is not horrible. I’m embarrassed by my behavior. I know I’ve probably lost the money I’d earned. I’ll be lucky if he doesn’t make me take the other toys and not pay me anything. He removes the toy and gets up off me. I’m breathing hard as I lie on the floor where he left me.

“Now get up and bring the toy to the bucket. Get on the next one and don’t say a fucking word.”

I get to my feet and take the toy from him. I hurry to the bucket and drop the toy inside. Then rush back and climb up on the six-inch dildo. I line it up again and sink down on it. It goes in easier than the last one. I look to him when it’s deep inside me.

“Time starts now.”, he says calmly.

I rotate my hips and ride the toy. It feels pretty good. I want to close my eyes again. But I keep my eyes on his. I expected some heat in his eyes, but he almost seems disinterested. Maybe I pissed him off by having to be forced to suck the toy. The room is so quiet, I can hear how wet my pussy is.

“Time’s up.”

I lift myself off the toy. He detaches it and hands it to me. I know that it will be going in my mouth no matter what I do. So, I keep my eyes on him and suck and lick it. My scent and flavor are stronger on this one. When I think I have it cleaned up enough, I put it in the bucket and return as he is attaching the seven-inch dildo.

“That looks big.”, I say nervously.

“It’s seven inches. You will take it all. After this one, you can stop for today unless you want more money. Now climb on.”

I straddle the vault and must lift myself on my toes to get the tip in. I take about half of it in quickly. Then I slowly slide down on the toy. I move up and down on it a bit to work it in deeper. I rub my clit as the toy goes in deep. I can feel myself stretch to accommodate it. I force the last bit in and gasp at the full feeling and slight discomfort. I don’t think anyone I have been with has been this long. I look up to him as the toy fills me.

“Time starts now.”

I move on the toy and slowly fuck it. I can’t help but wince every time I take it in deeply. I watch him again, this time his eyes are showing more interest. I start to imagine it is him inside of me, filling me. I bet he would feel so powerful inside me. My pussy is even wetter now. I rub against a spot inside that has me moaning in pleasure. It feels incredible.

“Time’s up.”

I keep rubbing the spot.

“Don’t you dare cum!”

I immediately stop and feel the flush of embarrassment. What’s wrong with me? I’m fucking a toy in front of him and getting off on it. I’m almost as fucked up as he is. I lift off the toy and my pussy aches at the loss of pleasure. He detaches it and hands it to me. Once again, I suck and lick at it. It’s a lot to take into my mouth, but I try to do a good job. I drop it in the bucket. When I return he’s holding a very small toy and what looks to be the next larger dildo.

“Let’s see, you lost your first $100 due to bad behavior. You have $100 for the six and $150 for the seven. Only $250 and the rest of the day to fuck up and lose it. Do you want to earn another $150 by taking the seven and a half-inch dildo in your greedy pussy? Or do you want another $250, which would double your money, by taking this little three-inch toy in your ass with lube?”

I really don’t want anything in my ass. But three inches looks like nothing. And with lube, it will probably just slide in. I have no idea if he will give me any more chances to earn money today or just set me up to lose it.

“Would I have to clean the toy with my mouth after it comes out of my ass?”

“No.”, he replies.

I can’t believe that I’m even considering this.

“Okay, I’ll do the three-inch”.

He attaches it. Then he takes a bottle of lube and coats the toy. I straddle it and carefully place the tip against my puckered little hole. I sit down slowly on the toy, and it slides in easily. It’s an uncomfortable feeling, but it does not hurt.

“Breathe through the discomfort.”, he commands.

I breathe slowly and when I let the breath out it does start to feel better. I press down to be sure I have all of it inside me. I do not need him saying I did not take it all.

“Okay, now fuck it slowly. Nice and slow, time starts now.”

I rock on it and move up and down slightly making sure not to pull it all the way out. It feels weird and a bit uncomfortable, but there is something darkly appealing about the feeling. I slowly fuck the toy and I notice that my clit is throbbing. I close my eyes and acclimate to the strange feeling. It starts to feel good.

“Time’s up.”

I stop moving and open my eyes. I lift off the toy. He removes it with a cloth and then drops it in the bucket himself. He returns to the vault and looks at me.

“Good job, young lady. Will it be the seven-in-a half-inch in your pussy now? Or the four-inch in your ass?”

“Um, do I also have the choice to stop?”

“Hmm…yes. But if you take the four-inch in your ass right now, I will bump it up from $250 to $300. That would put your total at $800.”

Earning $800 instead of $500 for the day is huge for me! The last one in my ass was not too bad.

“Okay, I’ll do the four-inch.”

He pulls out the toy. It is thicker than the three-inch was. I think about telling him that I changed my mind, but I have a feeling he would not take it well. He attaches it, covers it in lube and motions for me to get on. I straddle it and line it up with my already lubed ass. I sink down on it and I pause when I get a shot of pain as it stretches me.

“Ow, that hurts! I don’t know if I can do this.”, I whine.

“Breathe and take it. Your ass will adjust.”

I can tell by his face that I no longer have a choice. I breathe through it and sink lower on it. It’s much more uncomfortable as it slides in. I push down the rest of the way and pause as I breathe through the discomfort and ache in my gut. I look to him. His eyes are heated. I look down and I can clearly see the outline of his arousal in his pants. It still hurts, but I can feel that I am adjusting to the invasion.

“Time starts now. Fuck that ass.”

I move on the toy. It’s a big difference from the last one. But now I just have to get through it. I move it in and out of my tight ass. As I continue to move it becomes easier and starts to give me a dark pleasure. I close my eyes and ride the rigid toy.

“Time’s up. But stay up there with it inside your ass. Look at me and rub your clit.”

I open my mouth but realize I could quickly lose all the cash if I’m not careful.

“Please, Professor. Please don’t make me do that.”

“If you can make yourself cum with that toy in your ass, I will add another $100. You have five minutes to cum. If you refuse, I will raise up the machine so your feet cannot touch the ground and strap you to it. You will sit with it in your ass for twenty minutes. Your choice.”

I know he’s serious. I rub my clit and rotate against the toy. I feel tears forming in my eyes as I try to get myself to cum with the firm toy inside my ass. I pinch one of my nipples as I press hard against my clit. I continue to move up and down on the dildo. Finally, after a couple minutes, I feel my orgasm approaching. I pinch my nipple harder and then the wave crashes over me and I see spots dance in front of my eyes. When it subsides, I look up at him.

“Nice. Now get up.”

I lift off the toy. He removes it with a cloth and puts it in the bucket.

“Ready for seven and a half-inch in your pussy now? Or are you liking your ass filled and want five inches in that tight hole?”

“Um…I mean, I don’t…”

Professor interrupts me before I figure out what I want to say, “Let’s see, you are now at $900. But still, most of the day to fuck up and lose it. Take the seven and a half-inch dildo in your pussy and another three inch in your ass at the same time and I will be generous and give you another $500. That’s $1400.”

My stomach clenches at the thought of having both my pussy and ass filled at the same time. If I can be obedient for the rest of the day and not mouth off, I can go home with $1400 in one day! That would let me pay Amber back all the back rent I owe. I look up at him and say, “How long do I have to have them in for this time?”

The victory in his gaze is instant, “Ten minutes. But I will allow you to cum if you want.”

Before I can stop myself I reply, “I don’t think I will be tempted to cum!”

He raises an eyebrow but does not respond.

I quickly say, “Okay, I am ready.”

He attaches the large dildo and then attaches the smaller one behind it before adding lube. I straddle the toys and I adjust each so that they are lined up with my holes. He moves forward and helps me guide them in as I lower my body. The toy in my pussy feels huge to me. I feel so full as both toys penetrate. There is discomfort deep inside as the larger toy presses deep inside my core. I look up and notice that Professor is still standing close. I rotate my hips slightly and let out a whimper as both toys are fully inside. I release my breath and look at him.

His heated gaze causes a flush to rise from my chest and burn my face. He commands, “Ride them nice and slow. Your time starts now.

I slowly fuck the toys, being careful to not lift up too high that the toy in my ass slips out. I realize that I do not feel discomfort from the anal toy. It feels good sliding in and out, rubbing against the other toy through the thin barrier inside me. The toy in my pussy is slightly bent and is rubbing against that perfect spot. It is slightly uncomfortable but feels good at the same time. My breasts bounce as I ride the toys. I hear a soft moan and whimper and realize that it is coming from me. I had no idea this would feel so good. I am embarrassed by my twisted pleasure, but I just keep riding.

“Time’s up.”

I stop moving but drop my weight down so that both toys are fully inside me. I look at Professor and he is smirking at me.

He says, “Looks like you enjoyed that more than you anticipated.”

My face instantly heats, and I look down.

“Alright, enough for today. Wash all the toys in the bathroom. There’s a bottle of cleaner specifically marked for toys. Get the water hot and wash them carefully. Then dry them well with the microfiber towel and put them back in the box. When you’re done, you can take your lunch break. You can have an hour today, so you have time to clean yourself. When you are done, go up to my office in your panties.

Blue Eyed
Wow! Sexy!!!!
May 6, 2023, 12:51 PM
roughrider​(dom male)
A good session indeed
May 18, 2023, 3:14 PM