Chapter 50: I am seeing black Sir

Tuesday was my last session with Sir. It is Friday now. I needed more aftercare than usual, since I felt like a failure. Today I am going to get punished for having those negative thoughts. The toys I need are the clamps, both dildos, the crop, spoon and butt plug. I only have one request for Sir, to spare my calves, since I need to use them a lot this week.

Before we begin, Sir wants me to say why I am being punished. It is important to Sir that the reason must be strongly in my mind during our playtime.

“Do you recall why you are being punished?”

“Yes Sir, for having failure thoughts.”

“Yes. More specifically?”

I feel a bit busted for not being specific, but answer my Sir: “during our last session, I felt like failing. It took me so long to cum.”

“Correct.”

Sir educates me. The lesson is to not feel negatively about anything my body does or doesn’t. Those feelings don’t serve a purpose at all. Always trying my best at the objective and accept any consequences, no matter the result, is what Sir wants. Sometimes being unable to success is the objective.

“You do as you are told, you accept being used, or hurt, or humiliated, however I see fit. You accept whatever happens.

Remember these things during today’s session.”

“OK Sir. I will do my best!”

“Good girl.”

I am not in the sex room today, because my little Bobby put all the laundry there. Such a good boy, doing his chores. But no worries, there is a bed in the living room too. Sir wants me to show him around, to see how the new environment can be used. Sir needs an open wall where I can mount the small dildo on. I test all the walls, but the dildo always fails to stay put. The door works! It sticks. Sir approves. The session can begin.

“First, we have to prepare you.

That means plug in your cute little ass and nipple clamps on.”

I am on my back, on the bed with the camera pointed on my ass. Sir instructs me to bring my knees up to my chest with toes pointed down. Then I can insert the plug. I use a bit of lube and let is slowly slide in my tight little hole.

“Good girl.

Pull your knees up with your arms and stay like that for a moment.”

I do as told. Sir’s gaze is powerful.

“Very cute.

Open your knees.

Put your feet together.”

How will this be when Sir is doing this to me for real? Correcting my position. Touching me slightly and staring at me. I wonder. I crave.

“Very cute, little one!

I could enjoy the view for quite a while, but we must continue.

You may sit up and apply the clamps.”

Hmm, I feel comfortable again. Clamps on, no problem. They are as tight as they can be.

“Now, assume position four.”

I do my best to give Sir a good view. I aim the camera at the white wall on the right side of the bed. Perfect! I walk back to the wall, but realize I can’t see Jack shit of the Skype chat. I grab my phone and put it in front of my feet. Finally… I can assume position four and I am excited for the next thing. It has been a long time I showed my body like this to Sir.

“Now, I will test you – as a MERCY – for your calves.

Go on up on your toes for a moment…

Then tell me if your calves are too sore.”

Sir calls it mercy. I call it testing my limits. Damn, I don’t get some slack. Sir is pushing me. I do it and will tell Sir honestly if I am hurting or not. I lift myself up, standing on my toes. My calves don’t feel painful, guess I have good muscles in my lower legs. I nod at Sir that I am fine.

“All right, then that is your first position.

Remember your punishment purpose.

Keep thinking of that.

Begin.

I will wave when you are finished and ready for next.”

OK. Breathe in and out. I can do this. I carefully stand on my toes. Inch by inch. I try to relax. Clear my mind and focus on the purpose. Wait… Sir is leaving me. Where is he going? Is he watching me from a distance? I am curious.

I don’t know how many minutes have passed, but I am having a hard time to keep my balance. I do my best to control myself with my hands interlocked behind my head. Fuck! I fell anyways. I was just in time to break my fall with both hands in front of me. I look up at the screen. Sir isn’t back yet. I quickly correct myself to the position, but secretly laugh inside. That must have looked pretty clumsy. I feel like a naughty little girl. I see Sir coming back. Sir stares at me.

“You may now come down from your toes.

You can lower your arms.

Come closer to the camera and hold open your pussy for me.

I want to see it.”

I walk to the camera and open my legs. I show my glistering lips and moist pussy to Sir. I am surprised myself.

“Very nice.

You may stroke it slightly.”

Hmm, I am rewarded.

“That is enough.

Your next position will involve you on your knees, in front of the wall, but upright…

I want you facing the wall, with your hips, tits and nose very close but not touching.

You may kneel on something soft.

Your hands will be behind your back with each hand touching the opposite elbow.”

Wow, that is a lot of information. I read it twice and think I understand.

“Show me your hands behind your back in this way.”

Sir is so good with explaining and making sure I am getting it right. I show Sir my hands behind my back, but I need them more upright and horizontal. Sir wants me to demonstrate the position in front of the wall. I place the camera on the bed for this. Sir can correct me and watch me from my left side now. I have to keep my back and neck straight. I quickly grab some pillows for my knees and think I am ready.

“Begin.”

I close my eyes and focus on my breath. I worry for a second that I need to check in with Sir from time to time. But I don’t want to, else I can’t give myself to this position. I have to trust Sir that he will find a way to reach me.

I think of the purpose of this session and the feelings I had during the previous one. I start to talk to myself with my inner voice. I should never feel like a failure again. It is stopping me from getting in touch with myself, to ultimately let go. I deserve to feel pleasure and that pleasure can be achieved if I am me. Doesn’t matter if I am clumsy, goofy or whatever. I need to embrace everything that I am. I feel tears and my body starts to shock a bit. What have I done to myself all this time? Suddenly I feel proud, because this feels like a break through. A soothing feeling like a warm blanket overcomes me. I feel relaxed, so relaxed I almost fall asleep. Wow, I almost hit my head against the wall. I am so silly, but hey, I am me.

“Come back to me,” I hear Sir’s voice.

Sir wakes me up from my slumber journey. I feel a bit dazed.

“Let me see you.”

I show my sleepy face to Sir. I wonder what he is thinking. Did he laugh? When I almost hit my head? I think it is sweet that he checks on me.

“Now, I want to make that little bottom of yours pink.

Assume position two, mind the clamps.

And use your hand, 10 spanks each cheek.

Begin.”

This is a nice change, almost feels like home to get spanked again. I move the laptop towards the headboard and assume position two, ass to the camera and face in the mattress. I hit myself. I like it. I love it.

“Good.

Reach between your legs and stroke your pussy for me.”

Hmm, my pussy is spoiled.

“Perfect.

Is that little pussy wet? What a little slut I have.”

“Yes. Slippery,” I tell my Sir.

“Good. Show me your eyes.

Now tell me…

Is your pussy wet from being punished?”

“Yes.”

“Good girl.

Your next position will be right here, on the bed, on your tummy, facing the camera…

You will bring your feet up towards your bum and reach back with your hands to hold your ankles.

This will cause your lower back to do a reverse arch.”

I think I can manage that. Lucky for Sir that I am quite flexible. Still… Sir corrects me.

“Keep your knees apart.

I want your head up, facing the camera.

And that cute little mouth open to receive a cock.

Lower the camera, I need to see that mouth.”

Is he for real? I feel myself struggling with the thought of presenting myself in this new position, especially with my mouth open. I have to collect all my guts to finally open up my mouth. Fuck, I see myself on the screen too. I feel ashamed. I want to cry. My mind can’t take this. I am seeing black…

“I am seeing black Sir.”

“You can rest for 15 seconds.

Then resume.

Be a good girl.”

I guess this is all the mercy I get. And Sir is right. I need to be a good girl. I am not giving up. Fuck it, if Sir needs to see me like this then I want to give it my all. I resume and put my mouth open with tongue out. I am embracing all the emotions and feel extremely submissive… Obedient…

“OK baby.

You may rest.”

I survived. I make good use of my rest, because this was very humiliating.

“That’s enough.

I want you back in position two.

This time we are using the spoon.

10 slaps each cheek again.

Begin.”

Damn. Again. This feels like coming home. The playground I know. The playground were I feel comfortable.

“Good girl.

You may stroke your pussy again.

Reach between your legs and touch your pussy for me.

Go to position two and do as I have said.”

It is like time stands still. I go into an ecstatic high.

“That looks so good, little one.

That sweet pussy, ready to be used.

OK, time for the next position…

There are two left.

Let me decide which to use.”

Sir has his thinking face on. Sir’s face looks super cute this way. I want to eat him alive. Sir explains to me what a Strappado position is and wants to do something similar with me. It will be my final position. I move myself to the door on the left side of the bed. My small dildo is still glued to it, but needs to be moved lower. The perfect height is when my mouth can lick the small dildo and the chain of the nipple clamp is touching the ground while I am on my knees.

I interrupt Sir. I know it is rude, but I really need to pee. Holding it in, will be disobeying Sir too. Because that means I am not listening to my body. Sir is OK with me going to the toilet, but I need to take him with me. OK, this is awkward… I am thinking. I put the laptop down and take a pee. I don’t know where to watch. Sir is really keeping an eye on me. I am done and ready for the final position.

“Put the large dildo on the chain.

Mouth on the small dildo.

Hands behind back.”

I am a bit hesitant and clumsy. This is complex.

“Yes, get on it.

Just get it in your mouth and keep it there.”

I do my best, but my back is hurting. I need to bend over so low to keep the big dildo on my chain. Guess it is the burden of small boobs. Fuck, my back is really hurting. My legs too. I want to lift myself a bit to stop the pain in my back. But my nipples are aching this way, because the weight of the dildo is pushing the chain down. I stop and ask Sir if I am doing something wrong.

“Dildo is a little too low.

Spread your knees more and move your bum closer to your ankles.

The large dildo will pull on your nipples.”

“My back is not working with me. I am sweating a lot because of that,” I say.

“This is an example of Predicament Bondage.

It is supposed to be hard on your back or your nipples.

You must choose which gets rest.

Do your best little one.”

OK, this is another new thing for me. I will do my best for Sir.

“One thing.

Just put the toy in your mouth AND DON’T MOVE.”

This is really getting hard and difficult. I give it a try again. I want to see if I can endure this.

“Does my little one wants to stop?”

“I don’t.”

“So beg me for mercy.”

I am not going to beg, until I reached my ultimate maximum.

“Ready to accept anything else?

You may always plead with me,” Sir says with a smile.

I am still not giving up. It hurts, yes, but I can get over it. Maybe Sir wanted me to beg. Sir lets me in this position for a few more minutes.

“OK baby girl.

You may rest.”

Finally. I feel proud for not giving up, but my body is covered in sweat because of the pain. Sir is not finished with me. Sir wants me back on the bed with my legs spread. I need to bring both dildos and the crop.

I get to play with my pussy. Sir thinks my pussy is looking so cute and delicious.

“Good girl.

Just how I would touch you.

Gently.

Teasing you.

I would kiss you softly and tell you how proud I am of you.”

Sir drives me crazy. Sir teases me. Sir wants to slide inside and push deeper and deeper, so that I can feel Sir pulsing and throbbing. Oh my God! I wish so hard Sir was here now. I hope I get to play with my dildos soon. I want to imagine Sir fucking me, but I can’t. Sir needs me to hit myself with the crop. I am frustrated, but I won’t go begging for penetration. Obedient as I am, I hit my ass with the crop in position two.

“Good girl.

You may touch again.

I want you to just dip your finger inside…”

Fuck, even one finger feels so good now.

“Good.

Get your wetness.

Then I want you to bring your wetness up to your mouth.

Run it along your lips.”

Hmm, this tastes good. I bet Sir is jealous of it.

“Fuck baby.

I want to kiss you so badly.

Lick your lips.

Taste you.”

I smile inside. Seeing Sir craving awakens my dominant side. I enjoy it. Sir commands me to use the crop again, two more rounds, harder each round. I get to enjoy pushing out the wetness of my pussy in between. I hope I get rewarded soon. And I secretly hope that Sir is going to use both of my holes. I long so much for that… Getting my ass and pussy filled.

“Now, get the large dildo.

I want you licking it, getting it wet.

While you do it, I want you to tug on your chain.”

Seems like we are getting there. In my mind I am begging in secret already.

“OK little one.

I want you to very slowly, very gently, ease that cock into your pussy…

If at any time you want to cum, you may get on the floor and do so.

If the plug comes out, we will replace it with the small dildo.”

I push the big dildo inside my hungry pussy. I do it nice and slow as instructed. But… I want the plug out! And I am going to push it out! I need to feel the anal sensation again.

Success, the plug is out.

“Uh oh.

Get the small dildo.

You may remove the large one.

Get lube and lube everything.

My poor little girl is going to get her holes stretched so wide.

I want you to take your time with the small.

Work it into your ass slowly before using the large.”

Sir guides me like he always does. Sir makes fucking anal so enjoyable, making sure I use enough lube and keep rubbing my clit. Fuck, this is so good. The small dildo is inside my little hole and a few minutes later the big dildo is devoured by my pussy.

“That’s my good baby girl.

Letting me use her holes.

Giving me everything I want.

Good little slut!

Take the clamps off now.

Quickly.”

I fuck myself hard with both dildos. It is no longer too intense, it is just fucking hot. I am so close to cuming.

“Fucking do it you little slut.

Get on the floor if you need to.”

Yes! I need to! I move quickly. I don’t want to be too late.

“That’s a good girl.

This is what you get, being my little fucktoy.

TO use as I desire.

Move the small dildo and keep the large one in.

Slide it in and out for me.

Just relax and let me use your pussy.

You want me to cum deep in that pussy?”

I want it! I need it! Give it to me Sir. Fuck me… Use me… Oh my God! I can’t take it anymore, my eyes are filled with tears. As soon as I move the large dildo out, I squirt a massive amount of transparent fluid. Sir ejects beautiful thick sperm for me. I love it!

“Fuck. I think I shot the cam,” Eric says.

I giggle. Wow, this was a long session. Eric checks in on me after we cleaned up everything. I tell him I feel great. I feel so good.

“We touched on a lot of new things and you did very well.”

I feel extra proud hearing that. I enlighten Eric with all my thoughts of every part of our session and I know he will read this chapter soon :). Thank you for everything Eric. I feel blessed.

To be continued. Follow me to get a notification.

2 thoughts on “Chapter 50: I am seeing black Sir

  1. Do you plan to write anything more that is NOT BDSM based? What’s up with Kevin? Bob? Are you looking for another fuck buddy for real?

    Honestly these BDSM posts are not my thing…

    Liked by 1 person

    1. Thank you for your honesty. If you (only) want to read about Kevin or Bob you can use the categories in the Sidebar.

      I understand if you are not into BDSM. I wish I had more action with Kevin and Bob. The sessions with Eric are all I have at the moment. Kevin is ill (maybe long-term) and Bob is suffering from his hernia. I am not looking for another fuck buddy yet and I will post about Kevin or Bob when there is something happening. I am just not in luck yet.

      Like

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