Mature Lady Seeks a Wimp Ch. 05-06 by submanuk,submanuk

Chapter 5

I did not hear a word from the Mistress for the next week. The silence was difficult to deal with as I was obeying her instruction not to orgasm but couldn’t stop thinking about her. I stroked myself daily while looking at her pictures and relived the image of her boots and voice as she gave herself an orgasm on camera, all while I became more frustrated every day.

From her perspective, she knew that the level of commitment she required from her successful candidate was immense. So she had no intention of rushing the assessment process. She needed to be sure that the slave she took into her home was a completely submissive and obedient wimp. She did not want any nasty surprises later about a temper or disobedient streak etc. The selection process was therefore slow, testing and psychologically challenging for her wimp, just as the role would be if he was selected.

One week after our last contact I received an email.

“9pm online bitch,” was all it said. Again, she included another picture with it and I was excited to see the image. I was not disappointed…

She was pictured showing her wearing a tight, shiny, black catsuit, bending over to stick her curvy ass towards the camera. Again, the camera was placed low down, looking up at her and the caption read “Kiss My Ass, wimp!” She would’ve known exactly what effect it would have on me after she began denying me orgasms and I was predictably, an overly aroused, frustrated wreck looking at it. It had her desired affect upon me as I was now eagerly wanting to kiss her shiny clad ass in her catsuit.

I frantically stroked myself as I looked at the latest pic for the next couple of hours. I was beginning to think that her comment that I had an addiction to masturbating was turning out to be proved right. Usually I would’ve just orgasmed and carried on with my day but since I was now under instruction not to cum, I found it harder to function or stop fantasising about her. This latest image guaranteed that would be the case.

By the time 9pm approached I had been stroking for over six hours. I could barely think clearly as I stripped naked and knelt ready to log in.

At 9pm I logged in as “ownedwimp” and patiently knelt, awaiting Mistress to arrive. She finally arrived at 9.15pm and messaged to say:

“Stand, naked, hands upon your head with camera showing you from the neck down. NOW!”

I Instantly arranged the camera as instructed and switched it on. She silently observed me for a few minutes until her camera flickered into view showing a view of her sat comfortably in large arm chair. Again, the view was from the floor looking upwards to her. I was beginning to think I would only ever see from this angle but I understood why she did it. It made her look extremely imposing and superior, looking down sternly.

As I tried to see the screen from my position stood away from it, I could see that she was fully clothed, wearing jeans, boots, black shiny latex gloves and a casual top. The whole scenario seemed bizarre that I was stood naked while she sat comfortably, fully clothed.

“Stroke that tiny cock as we chat, worm! Do not stop and DO NOT CUM!” she said sternly.

I was beginning to squirm from the humiliation of standing naked in front of her and now being instructed to stroke myself but I was grateful that my face wasn’t in the camera view.

“Have you obeyed my instruction not to cum this week?”

“Yes Mistress,” I spoke quietly in response.

“I hope you are getting used to it wimp. If you are selected to come here you will be locked in to the tightest metal chastity device you can imagine. In fact I already have it my possession. Would you like to see it wimp?”

I really did not want to think about it but I knew that I had agree to see it.

“Yes please Mistress,” I submissively replied.

In her tight, shiny gloves, she held up to the camera, the most gleaming chrome device which, as she suggested, was possibly one of the smallest and unforgiving devices on the market. In contrast to the shiny black of her gloves, it reflected the light from its shiny chrome coating and left me in no doubt that she was certainly serious about locking me into it if I am accepted by her.

“This device will be locked on to your tiny cock and will only ever be removed when your hands are secured and unable to touch that little thing between your legs. Once accepted here I will take full control over that tiny cock.”

“How does that sound to you bitch?”

“Very difficult Mistress. I already find myself fantasising more and more about you as my frustration increases, so I think that would be very tough.”

“Good! What have you fantasised about this week, wanker?”

“Lately, I seem to be thinking more about licking you and being under your control Mistress. I don’t seem to imagine myself cumming in those fantasies now as I keep imagining you denying that privilege to me. I also struggle to stop my stroking and fantasising Mistress as there is no orgasm or conclusion to end my stroking.” I explained.

She didn’t say it but my response pleased her.

“Look at you, a filthy, perverted wanker standing in front of me stroking that tiny cock. Do you realise how utterly pathetic you are?”

“I do Mistress. I feel very humiliated like this.”

“Awe poor baby… I am so mean to you aren’t I?”

“I don’t see you as mean Mistress. You just know what you want,” I replied.

“This is true wanker. And right now I want to see you stroke for the next two hours. You will not cum or speak. Just continue doing that.

With that, she switched off her camera and I had no idea if she was even still watching me.

Not a word was said as I stood there silently stroking myself on the camera, trying desperately not to get too close to cumming. I had no idea what she was doing but she continued to sit there for a while watching me with her camera switched off. The obvious unfairness of the situation was not lost upon me. The growing power imbalance between us was starting to reflect the attitude she has towards her prospective slave. The lack of reasonableness, empathy or courtesy was now evident in every communication from her. I realised that this was turning into a thorough assessment process which wasn’t going to get any easier.

After about an hour of stroking I was desperate to move or sit down. I was way too scared to ask however so I shuffled from leg to leg to try to reduce the aching as I continued to stroke.

Then her voice startled me :

“You disgust me wanker! Turn around and face the wall as you continue wanking!”

I quickly turned around so that my camera could only see my naked rear and I continued to stroke myself. I felt so humiliated facing the wall and wanking under her supervision but I started to remember her description of the position I had applied for and realised that this could be an example of how things might be if I were accepted to the role.

She relaxed with a coffee as she watched me and thought to herself that I was showing signs of being the complete wimp she hoped existed for the role. She felt that she needed to test me further yet however so she decided to continue ramping up the control and humiliation to gauge my responses.

She decided to leave me there in this position for a few more hours as she watched a movie. From time to time she would glance at the screen to check I was still obeying the instructions but there was no contact at all. I, however, was aching, highly humiliated and desperate to cum to relieve all of the hours of stroking I had been doing.

The humiliation grew more intense as the length of time turned into hours. It now became an arduous task and I started to worry that she would leave me like this all night. I knew it must be nearing midnight and I questioned my own capacity to continue. Luckily there was at least a sign that she was still there as her voice boomed out.

“Absolutely fucking pathetic! You really do deserve to be locked up in my chastity cage. Maybe you’ll experience that soon enough boy.”

“Now, stop stroking. Slap yourself on your ass. And I mean SLAP hard! I want to hear it loudly and see the hand print! NOW!”

I obeyed and did my best to slap myself hard. It did hurt but she was unimpressed.

“You are too weak to even slap yourself properly boy. Maybe you’ll soon experience what a real slap should feel like! Now fuck off.”

This was becoming her usual way of saying goodbye so I meekly said “Thank you Mistress,” and I logged out.

I had spent the whole night stroking, with the last three hours of it on camera as she watched or ignored me as she desired. My mind was a whirl of emotions as I tried to compose myself. I realised that I was fast sinking under her control but I had signed up for that when I replied to her ad and I didn’t want to back out at this stage.

Chapter 6

I struggled to get any sleep that evening. I desperately needed to relieve the frustration and cum but I would not dare disobey the Mistress and ruin the efforts and commitment I had made to be accepted by her. By the time I awoke in the morning I became instantly aroused again as thoughts of her popped straight into my head. I resigned myself to expecting no contact from her for a while again though as I had noticed that she tended to disappear and not allow any contact for days at a time. I was therefore particularly surprised to open my emails and see a message from her already.

“Log in as soon as you are awake bitch!”.

I trembled a little while reading that and felt just a little disappointed that no pic was attached this time. I did however get myself into position, naked, kneeling with my face out of shot and logged in again immediately. I knelt nervously wondering if she knew I was there but a message came through quite quickly.

“Get your camera on NOW bitch!”

I hastily obeyed and must have looked quite pathetic on my knees again.

“You are not permitted to move from this spot all day unless I give permission. If you need the bathroom or water etc you will need to beg for my permission and if given, you will be on a strict time limit to get back into position. If you had been here right now, you would be kneeling in a cage with your hands cuffed behind your back, so this is a much easier task than you will face if you are accepted by me.

You will of course not know if I am here watching you so you may type your request first before begging verbally for permission. You will not move from that position however if permission is not forthcoming from me. Is that clear worm?”

“Yes Mistress,” was all I could say in reply. I had a feeling that this would be an extremely tough day for me and all of my plans for the day just went out of the window but I didn’t want to fail or disobey.

“This will be a tedious, arduous, mind numbing day for you wanker. But remember this, you deserve every second of mistreatment from me and I will enjoy putting you through it.

If you fail, our contact will cease immediately and permanently. This is a very important part of the role you have applied for, to remain locked up, caged, in solitary confinement etc for prolonged periods at my will. This task is therefore a necessary test which will become a daily part of your life if you are accepted.”

My head bowed as I read her words. It seems like she didn’t even plan to switch her own camera on so the unfairness seemed even more tangible. I was quite shocked at how the day had commenced and I suddenly realised also that there would not even be any TV or radio to listen to as I remained in position. She was indeed correct that this could be a very tough task and one I was scared might be too much for me. I was very conscious however of the consequences of failing it and that it was merely a taster of what might be if I’m selected.

“I hope for your sake that you have used the bathroom and eaten already this morning as there’ll be no permissions granted for the next few hours.”

“Although, to be totally honest with you wimp, I really hope you haven’t done those things as I enjoy being cruel to you.”

“I warned you that I would not be nice!”

“As the day goes on and your begging increases, I will orgasm many times watching you struggle to cope.”

“How does that make you feel wimp?”

“I feel very humiliated kneeling here and scared that I may struggle Mistress but I also feel pleased to hear that it will give you such pleasure.”

I knew that I was immediately off to a bad start as I hadn’t eaten or used the bathroom yet. She had misled me into logging in straight away as I awoke and I didn’t even keep my phone nearby to check emails or pass the time. I suspected that she would not have allowed me to use it anyway, even if it was within reach. Her attitude was clearly very cruel today I noted and I wondered if this was actually just her normal attitude she was displaying.

My mind was already going in to turmoil, anticipating the long day ahead but I sensed that she was already enjoying herself. As if she had read my mind, she suddenly switched her camera on so that she could emphasise her pleasure as she again masturbated at the sight of me kneeling, naked under her total control.

I looked up at the screen to see her from the waist down, sat in the large chair with her pantyhosed legs open wide apart as she writhed and moaned with her right hand tucked deep between her thighs. I wanted to beg for permission to stroke myself but I was too scared to interrupt her pleasure. She wriggled and breathed heavily as a vibrator worked it’s magic and she steadily built towards her orgasm.

“Ooh… Fuck that feels good… ahhh.”

“I’m so wet bitch, I could do with your tongue right now… ohhh fuck.”

I couldn’t see it but her head rolled back as she began to moan more loudly.

“Ahhh… I’m going to cum wimp, while you get nothing!”

With unrestricted moans of pleasure she gasped and pulled her legs together as she came.

A few minutes silence followed it as she basked in her pleasure for a while before composing herself enough to speak again.

“My pantyhose are soaked, bitch. If you were here they would be stuffed into your mouth after you had licked me clean. Oh well, one can’t have everything.”

She laughed to herself and corrected her statement…

“In your case, today you will learn that you can’t have ANYTHING, worm. Fuckwits like you deserve to suffer for my pleasure!”

With that, her camera was switched off and I let out a quiet whimper.

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