Chasing Me Chasing You

An uncollared submissive struggling through depression, motherhood, and the constant craving of her next orgasm.

Training Session, Part I

So I have this fantasy….

Where I am blindfolded and seated next to Sir. We are in a room with a female dominant and others that entered after my eyes were covered. I can hear footsteps and Sir tells me to open my hand and hands me a drink. It is just water, but my body is already shaking in anticipation, so water was fine. Sir sipped his glass of bourbon (I can smell it) and explains to me what is about to happen. When we arrived he said I was to be used to help train some new submissives, and he was going to use the opportunity to train me as well, but that was it. Now he explained that it would be my job to try and make male submissives come, and they would be punished if I succeeded. Their Domme would choose how I was to tempt each one.

I asked about whether I would be allowed to come as well. Sir explained that that would be my training. I was not allowed to touch myself, unless the Domme ordered, but I needed to come at least once with each sub. I thought about this and realized their must be some sort of catch. He laughed as he must have seen my confused face. He grabbed my collar to pull me in close, told me he loved me, and threw me onto the floor. I scrambled into a present position, trying to look graceful and poised. Sir must have had great faith in me to loan me out for a training like this, I wanted to make him look good.

Rye, stand up.

I immediately stood, hands behind my head.

Very pretty girl. Your Sir was right to show you off. My name is Dawn, but you are to call me Mistress, do you understand?

Yes, Mistress

Lovely. You are here to help me with a few of my subs. They aren’t as well trained as you, my dear. You must help them to appreciate their service to me as a fulfillment of my needs, not their own. So, your Sir and I have discussed your talents and how they may help me to test these bulls. You will have three chances to show me how worthless they are. First with that pretty little pussy of yours, then with your mouth, and if they can hold out, your asshole. If they come during any of these tasks, they will be punished, if they do not, then you will be punished. Your Sir highly recommends you, so I expect results. Do you understand?

Yes, Mistress

Now, I understand that your Sir has his own challenge for you. But be aware, my subs have not been given permission to hurt you, though they can touch you, should they wish. However, you are only to take orders from you Sir or myself. Are you ready to begin?

Yes, Mistress

Your Sir will help you up on the bed and we will get started. Also, just for clarification, when I am speaking to you I will call you Rye. My subs all have various names and slurs and I don’t want to confuse you.

Sir helped me up onto the bed. He began rubbing my clit.

You are going to do great, cunt. You never cease to amaze me.

He slapped my ass and moved off the bed as I heard footsteps approach.

I felt a hand on my hip as a cock slammed into me from behind. I felt the body behind me shudder and sigh as he started to move almost immediately. I tried to match the rhythm. If I could come quickly, then I could focus on making him come. The last thing I wanted was to disappoint Sir and be punished. But the sub kept changing his rhythm, making it hard for me to match, or build toward orgasm. It became clear that this was his plan. He would try and keep himself from coming by stops and starts. Not a terrible idea, but that wouldn’t help me. We both wanted to avoid a punishment, so I couldn’t let it rattle me. I started to grind back onto him. He could go as slow or fast as he wanted, but his balls still hit my clit every time he thrust forward. I couldn’t keep from moaning as I found the perfect spot.

Are you pleasuring her, you waste, or just trying not to come? You are being selfish, slave. 

I felt him thrust forward in a jolt and I heard the slap second as it came across his ass. He groaned and I moaned as he ground against me. A few more of those and Mistress would be doing my work for me. The sub slowed again and I pushed back against him in protest. This was almost aggravating. He picked up speed again and I realized it was because his Mistress was walking around the bed. I could hear her heels clicking up by my head. I couldn’t hear Sir though I knew he was there, he would never leave me.

That thought was all I needed to set me off. I picked up my own speed, grinding against him and moaning. He tried to slow my pace as he grabbed my hip, but I was too close. I moaned and grabbed at the bed sheets.

Let her come you selfish worm.

The subsequent slap on his ass was just what I needed. He thrust forward and I cried out. He kept moving inside me, but I stopped pushing back against him. I needed a moment to recover before I set to my task.

Stop slave. Your efforts for her were pitiful, but she came even without your help. Now you will have to let her try her skills. Rye, I want you get up off the bed. Your Sir is to your right and will help you. Scum, you are to lay down on the bed.

I moved to my right and found Sir’s hand waiting for me. He helped me up and kissed me hard. He didn’t have to say he was proud of me, his hands said it for him. He sat in a chair a few steps away and let me sit on his lap. I’m sure it was only for a few minutes, but it felt like hours. I could hear rope and clips over on the bed, but I remained cuffless, so I assumed the other sub was being restrained.

We are ready for you Rye. He has been completely restrained to your will. Your Sir has detailed your talents such that to keep things interesting, you will only have five minutes to make him come. I have no doubt that you will be successful. Please don’t disappoint me.

Yes, Mistress.

Sir helped me back up on the end of the bed. I was between the subs legs. I rubbed up his thighs with both hands to find his cock erect and I could hear his heavy breathing. Without the ability to change rhythm, I knew I could bring him to climax within the time.

I licked up and down his shaft as I massaged his balls. I took him into my mouth to gauge his length and girth. He was slightly longer than Sir, but didn’t have the girth that my Sir possessed. I used my tongue as I pulled out to the tip and back down to take him again. He moaned and struggled against the ropes and I smiled.

She’s good and she knows it, worm. Four minutes left.

I picked up speed and took him as deep as I could. I kept massaging his legs so I could feel his muscles tense. When he started to tighten, I knew I had found the right speed. I reached up and found one of his nipples. I rubbed it slightly until it peaked in my fingers. He groaned and started to thrust his hips. I used my other hand to hold down his pelvis and started to pull gently on his nipple. I kept up the same speed as his legs started to shake and his breathing quickened.

I let go of his hip as I pinched down on his nipple. He immediately began thrusting wildly. I tightened my lips around him. A few groans and strains and hot liquid shot down my throat. I kept him in my mouth as he softened and relaxed. I rubbed his stomach and legs to calm him down. Almost as a way of saying sorry for the punishment he would now receive, because of me.

I sat up to kneeling and laid my hands on my thighs; waiting for further instructions.

Get up scum. She unmanned you. Go back to your cage. Rye, your skills are not exaggerated. Take a few minutes to get some water and see to your Sir. I will go and retrieve your next victim.

Sir helped me off the bed again and handed me the water glass.

It took you three and half minutes, Rye. I am surprised. Next time you will do it in two.

I took a sip of water.

Yes, Sir.

2 Responses to “Training Session, Part I”

  • Sir

    Rye, you will finish writing this story, with one post on Saturday and another on Sunday.

    • Rye

      Yes, Sir

Reply

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