My Boss Is A Mistress Ch 03

This story is about a Mistress / slave relationship, chastise, butt plug, flogging and some more. For the ones following chapter two, Stephan notices he does not have true idea of how deep this new life goes, he admits Veronica is a turn on for him; He also has an eye for Claire who is training him.

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I had my shower when finished I got the cock cage and collar on as Veronica had instructed me. She left early for the office; I finished off my breakfast, made the bed and the rest of the other house duties. Once again Veronica left female clothes for me to wear, giving me the option to use them or not. Last night she said to me depending on how I do receive Claire when the front door is opened, I will be offered further options. She adds that Claire has a free hand on me from now on, excepting for my little penis as she likes to call it which is currently caged until further notice. The news is definitely not something I was eager to know or experience by having another Mistress doing as she likes with me. My doubts appear understanding Veronica wants me having them as part of training and at the same time playing with me. She is, and will carry on entangling my psyche with mind games she duly warned me about she does like getting me into. Now here I am, not knowing what is the correct choice to make. Should I remain nude or dressed in the female clothes left by Veronica for me, should I bow as soon as Claire comes in to get the option from her and if I dress in female clothes and it's not that? What is it I have to do in order to have a choice or avoid Claire deciding all day long?

The phone rang, "Stephan?" Veronica asked.

"Yes Veronica." I said.

"Claire is about to knock on the door have a good day." Veronica said and I heard her giggle as she hanged up.

I hear her knock as I hang up the phone, "Claire?" I asked.

"Yes, open up slave." Claire said.

"Good morning Mistress." I said and kissed her feet. Claire dressed with a long leather overcoat, boots, gloves and a big hand bag.

"Hello slave." Claire said and smiled at me dropping the bag.

"I see you are happy." I said.

"Yes I am you know Veronica gave you an option and if I found you in female clothes I would give you another option you have just lost it. Now, get the bag and put it on the table." Claire said still smiling and enjoying my wrong choice.

"That was unfair." I said getting a little out of my comfort zone.

"Don't push it slave, get my overcoat." Claire said.

"Sorry Mistress." I said getting the overcoat off her and hanging it up. Claire has a crotch less pantyhose, leather top and long leather gloves on, with the boots I had just kissed. I'm totally exited. I cannot believe it; I want to be all over her. I hate the fact of having a cock cage on and being a slave at least right now. Claire knows it and is having fun at my expense, although she would prefer to have the cock free for her personal use.

"It is time you open the bag and as you get the items out, tell me what are they and their purpose." Claire said knowing how turned on I am.

I started off, "A flogger as a warning and hope it is not to use on me." I said and Claire laughed.

"Carry on slave." Claire said truly having a field day.

"Condoms, to use with me! Mistress Veronica let us go for it, have you the key to my liberation?" I asked happy, hoping and confused.

"More rightly in you, carry on." Claire said and I went white as my excitement ended there. It literally disappeared into thin air. What now? I said to myself.

"Lube to lubricate the butt plug that could get inserted into me." I said as I saw the plug in there before getting it out and remained frozen for a second.

"Yes that is right, carry on slave." Claire said knowing it will take some taming.

"Ball gag, inflatable gag, ropes, blindfold to use on me and restrain me." I said.

"Good slave. Now go to Veronica's wardrobe and bring the clothing you see at plain sight including the footwear." Claire said.

I go to the bedroom getting a shock when the clothing turns out to be a maid's uniform with sandals. I take my time to get back to Claire, "Please not this." I said looking at her.

"Remember you are owned. Now dress in them slave." Claire said.

"Please." I said as I get to my knees.

"I thought this would happen with you, follow me slave. I will not tolerate disobedience." Claire said and we go to a bedroom, which has a beam.

"I only requested to you. What is happening?" I asked wondering where the happy Claire has gone to. I'm now getting to know the other Mistress Claire, the strict one.

"You did not obey me. Now, your wrists." Claire said as she puts leather cuffs on me. She then ties ropes to them and these same ropes are now over the beam.

"Mistress please, what is happening?" I asked again as she pulls my arms up high, securing the ropes to a hook I have not noticed up to now and guess its purpose for it.

"It's time for a lesson." Claire said and inserts the inflatable gag in me.

"Mm." I said.

"I'll hear what you have to say after chastise." Claire said.

"Ah, hm." I said trying to move, my hands only moving a little and my feet are now hooked to a spread bar.

"You can now yell as much as you want, you are going nowhere until I'm finished. I'll worm you up and then flog you." Claire said looking at me with a serious face. Then her leathered hands touch me all over, moving now to my back, still touching me. She is obviously enjoying herself fondling me. She makes me feel helpless and dependant of her. She kisses my face tenderly then kisses my back between my shoulder blades. A moment of silence, her hand touches my bottom and a finger starts playing around and with that same finger she goes round my body outlining it as if a belt. Once again at my back her hand slips downwards between my cheeks, her leathered finger goes as a spear head which plays as if to invade me but she doesn't. She decides to just probe making me aware how vulnerable I'm to her. If it were that only I'd love to let her play all day long, but know it's more. I feel her full hand resting on one of the cheeks. Yes my cheek as if marking and measuring the target. The hand lifts and I soon feel it back on my cheek in the way of a spank, it startled me. The lesson has started as she mentioned it would, and then my other cheek meets her hand, gradually getting harder as it goes on. I start feeling the sting on my buttocks; Claire administers a good number of spankings. By now I must have them red because they are stinging.

"Ah." I said muffled by the gag as it gets hard.

"The right call. Now, I'm passing on to the flogger." Claire said.

The flogger is soft on me. I have no previous experience with the leather threads as they swish through the air and they thud on my skin, it gradually starts getting harder. Claire is flogging me in intervals but now hard at least for me. I have a stinging pain and I cannot hold the tear as it flows down my face. She comes round and as the tears are visible to her she decides to stop. I admit she has experience reading my tolerance combining the purpose of the lesson.

"Uhm." I try to cry out loud, the sound is definitively muffled.

"That is it for today if you behave." Claire said and adds, "I want to fuck your arse, which I will call pussy from now on. I understand Veronica has told you about my desire with you."

"Hm." I said as I feel my stinging back side.

"Yes I know, but before I untie you the plug is going into you." Claire said looking at me with the plug in her hand and a condom in the other. I hear her open the latex casing and see as she slides it on covering the plug which shows how invasive and thick it is to my eyes. She then lubes it in front of me and turns onto my back. I feel the sticky goo in my butt; she plays around and pushes a little as I feel the invader.

"Baby push hard as I slowly push into you. It will hurt less." Claire said.

"Ah, mmm, aghh." I said as she tried to get it in.

"The plug is a small one if not the smallest I have. You are truly closed there. I'll have to help you with my fingers." Claire said and she puts a condom over a finger of her leather glove, lubes it and the finger probes me and forcefully goes in.

"Ah, ah." I said it hurt but it's far less invasive than the plug. Claire plays around and finger fucks me until it is acceptable. She withdraws and as she goes in again it feels thicker. It's two fingers and the same treatment is given. She withdraws and it again gets repeated but thicker than the last time and it is not enjoyable. She plays with my arse loosing it up and I do get accustomed now to her invading fingers. I also feel what I suppose is the prostate touched by her fingers and a strange feeling comes over me which I had not ever felt until now.

"I see I'm getting your prostate, you have loosened up a little, soon or in a short time you will like it and I might make you crave it. Now I'll get the plug inserted in you my pet, but a little finger fucking will get you into the mood." Claire said and finger fucks me generously. Her fingers are now withdrawn and she replaces them with the plug, the head of the plug rests in my hole waiting to go in when she is ready to give it to me. The pushing starts, the head stretching my butt hole as it starts going in.

"Ah." I said with discomfort. I'm so helpless no matter how much I try to move.

"More lube dear it is going in now, no matter what." Claire said withdrawing it and lubes it in front of me. Her face is one of who is seriously working on something which has to get it finished with, before getting to the following one. The one she is seeking for and determined to get it her own way. It comes to my attention that Veronica is not too concerned about it and a price she accepts for getting me trained. Claire once ready puts the tip back into my hole, pushing it in going slower as she is doing it. The head goes in and it gets thicker and not much of a struggle as she carries on pushing until the thick part is in and holds it there not moving in or out. A minute later she gives it the extra push and gets past my sphincter as it gets thinner and slips in. The discomfort subsides not having the thick part in my anal ring now and my butt gets familiar with the invader settled there.

"Ah, hm, ah." I still complain.

"Don't worry dear the worst has passed; your pussy is now open." Claire said and gets the spread bar off me and my arms are lowered to be untied. I still have watery eyes; it is my ego the one shattered, overridden, my hole well it's open now. The gag deflated and removed.

"Why?" I asked.

"You needed a lesson, understand I love you also and you do have to understand your place as a submissive. Remember you are a slave to Veronica and for me to train. When any of us chastise you there's nothing you can do but withstand whatever is done to you. This way you will learn and accept your superiors. With playtime you will have safe words. About the plug, well, truth is said I want to peg you and since Veronica gives me a free hand with you I'll fuck you. If you want to know when it will take place, if possible my idea is just before I finish training you. It will be given by me as a graduation gift. After that I will have to ask permission to have you as the pussy I want you to be with me." Claire said looking at me in a hungry way.

"You could have advised me about chastisement Mistress." I said.

"If you had obeyed me it would have been playtime. Now kiss my feet and thank me for the lesson slave." Claire said.

"Sorry Mistress, thank you Mistress." I said as I watch the glitter in her pussy.

"Kiss it slave." Claire said and I happily kiss her wet pussy.

"Thank you Mistress." I said.

"Now dress as a maid." Claire said.

"Yes Mistress and the plug?" I asked.

"It remains in. Get dressed." Claire said so a crotch less pantyhose, panty and the shiny maids' outfit is on me now which Claire helps zip up and in the rings it has at the top she adds a padlock locking me up in this attire.

"Why do you have to put the padlock on me?" I asked.

"Veronica told me that if nude the padlock comes on and she will get it off you when she is back." Claire said.

"That is unfair." I said.

"Not again slave. If I hear you say that one more time today, I will fuck you." Claire said looking serious into my eyes.

"May I ask you a question?"I asked trying to change the mood.

"You may." Claire said.

"Will I be able to tell if chastisement is coming my way?" I asked.

"You'll certainly will. It is quite simple obey your Mistress or..." Claire said.

"Thank you Mistress." I said.

"Let me tell you a little about me which might give you a better idea about who is dealing with you. This said not to consider you are played upon. Veronica once we became friends and Jennifer already living with me told me that the only basic difference between a Master and me is that I have a pussy and a missing a cock. I like giving anal sex and now that I have said this to you I recognize I'm quite similar to a guy. I like giving I do admit I like receiving every now and then, for the rest cunnilingus is best. Veronica is right again for a change. Do you know what that means?" Claire said watching my face.

"Truth, I would like to avoid you telling me, but I have a hunch you will anyway." I said not wanting to hear.

"Good you mentioned that. Another word of advice, don't challenge as you have just done. Your words are not that of a slave but of a freeman and you are not one any longer. I add as well not to ever let your dominant with without an answer that is expected from you. I learnt through experience and it's another lesson to be learned the hard way if you know what I mean. Metaphorically speaking you started a being a stallion with Veronica and unless she changes or is truly into the mood she would let you remain as you are or were. In time she would finger fuck you and later on fuck you only if that makes you more subservient to her. She is not much into anal that I know of. That is certainly not me from stallion, I'm in the process of turning you into a gelding and if living with me I would make you become my mare, bitch and slut." Claire said now acknowledging she is quite a bitch of a Mistress.

"Just as well I belong to Mistress Veronica." I said and happy about it.

"Let me settle the maid's cap on you." Claire said ignoring my comment.

"Definitely not very sexy." I said.

"Oh, don't think so, as soon as your pussy is settled I'll be fucking you sexy thing. Now get cooking for Veronica." Claire said playing out her own agenda with me.

I did all the cooking as indicated by Claire, and as done before once I cleaned everything up. We both have a beverage this time latte, "Is this the way my life will be from now on?" I asked.

"Regarding being a slave yes and all that Veronica wants from you is a command. About the maid's outfit yes and no. You will not necessarily have it on every day; at least I do not think so." Claire said.

"I wonder if I'll be able to go with this regime." I said watching Claire who is turned on by this uniform I have on.

"You will, one you settle in. You are a natural." Claire said.

"Does she like sliding things up my hole?" I asked.

"No she doesn't, I do. I want you and if I had you living with me, your pussy would get used often." Claire said looking hungrily at me.

"What do you get out of it?" I asked.

"The power I constantly hold over you turns me on. I'm top you are a bottom I get wet thinking how you have to submit to me. Your behaviour is also inviting when I play male and you play female and getting my cock into you is so sexy. Speaking about that, bend over that table slave." Claire said.

"Yes Mistress." I said and bent over not wanting to get flogged again at least today.

Claire lays her body over my back, "That is what you will feel with me." She then started feign fucking me. With her hand she touches the butt plug which gives me an extra sensation in my butt. Shortly after she gets her hand at the base of the plug pulling and pushing the plug in me but not forcing it out. It does feel as if I'm being the one fucked.

"Please stop." I said.

"Yes for today. Get the idea of what I'll do with my cock in you." Claire said.

"Yes Mistress." I said knowing I no longer can go against her. I know she is taking it easy with me and mostly getting my mind ready for her.

"I'm pulling the plug out of you stay still slave." she said pulling from the base of it. I feel my hole being stretched.

"Ah." I said as I feel it thicken and then get thin as she finally pulls it out.

"Slave, clean it up and bring it back to me." Claire said and I did.

"Here you are Mistress." I said as I handed a clean plug getting rid of the rubber she used it with.

"You now feel emptiness I'll soon fill you up." Claire said knowing the sensation.

"Yes it feels awkward for me and it's that feeling you have just mentioned which I'm experimenting." I said.

"As yesterday it's bondage time." Claire said.

"Not again." I said.

"You now know the drill, lie down." Claire said and gets the restraints as the day before and I passively accepted the bondage.

"Mistress you are leaving now?" I asked.

"Yes dear here to remind you of me." Claire said and puts her finger in her pussy then passing it into my mouth. She then dressed, by that I mean she put her leather overcoat on and left.

I fell asleep again until I heard Veronica come in after her day at the office.

"Mistress is that you?" I asked but I get no answer and hear her foot steps as she goes to the bedroom. After fifteen minutes I hear her come back.

"Hello slave." Veronica said and released me from the bondage.

"Mistress I was missing you." I said as I kiss her feet.

"You are a fast learner slave. I want you to kiss and lick my feet then massage them, when finished eat my pussy." Veronica said, I see she has painted lips and dressed with leather gloves and a pearl necklace.

"You look tired Mistress." I said.

"Yes I am, now get to work." Veronica said and I did, kissing her feet as requested then licking them as she wants soothing her in the process.

"Please Mistress, let me eat you now." I said and Veronica just opens her legs letting me in. I'm licking and nibbling at her pussy and clit until I hear from her the nearly imperceptible moans and soon orgasms letting her release all the day's tension.

"Stop slave, thank you for that. Now it's time for dinner." Veronica said.

"Yes Mistress." I said and set the table getting everything ready as she puts her knickers on I added, "Mistress when you are ready."

"Sorry I'm not normally this way, I've got a lot on my mind." Veronica said.

"Is it all business?" I asked.

"Yes but as you know on occasions that also affects other things." Veronica said.

"Depending on the situation you are up against if it's not for long it does make business worth it." I said.

"Yes, just that in this case it could affect our relationship which I thought it would not." Veronica said.

"By that you mean I'm free do I get back to work?" I said with a hint of happiness and sadness in me.

"No, no. You are not free. Let me tell you, before getting to know you I was told I'd fall in love as I have always wanted, and would for reasons that have and not to do with him in a direct way lose him in the process. I guess that which I have just mentioned must be referring to you, because it is happening. I might have to pass you onto Claire. She wants you desperately and even Jen wants you." Veronica said.

"And you?" I asked, wondering what is happening.

"Of course I want you but I have to travel and have people here at home for some time which makes it difficult for me. I will miss you if I have to let you go and know that I will not get you back if they get to own you after a week. The girls are hungry for you. All I can add, if it's you, this said man is going to love deeply the relationship that comes to his life after me. If any of this is true, when time comes I'll have to find a replacement." Veronica said not licking what she mentions to me, which does make her feel upset about it.