Mistress The Pimp by WM

That feeling when a hard rubber cock enters your arse for the first time, is hard to describe. A deep warm, electric feeling boring inside. Physically, a culmination of a month or so of training with various butt plugs and months of psychological training from Mistress. The physical sensation whilst incredible was an absolute second to the torrent and tumult of emotions raging inside my quivering body. This is the ultimate in submission to my mistress, my Empress, my Owner, so many fetish firsts have fallen with her over the last year that having my anal virginity taken by her seems right and is the logical step in her use of me. Her capitalisation of me, if you like. For although this union between slave and owner has been sensual and orgasmic and about trust and furthering the bonds between us. I know Empress’s over-riding desire is to prepare me for the market.. Capitalisation was certainly the right word.

When I first came to see Mistress I had expressed a desire to learn to love to lick other men’s cum. This wasn’t unusual for her, many submissive men crave the humiliation and the degradation of being made to suck another mans cock, or lick their cum. One Mistress once told me that a sub can never really count themselves as a slave until they have given up their barriers to their owner. So I suggested to my beautiful, jet-black hared Mistress, that maybe licking someone else’s cum, direct from condom to her shoe might be a palatable way to start and then to graduate on, she agreed and said to leave it to her. At this time I didn’t realise the true majesty of Mistress’s plans for me but boy, did she have plans.

The next session we had, I lay below Mistress as she sat imperiously upon a chair above me. Wearing a little summer dress, as beautiful as it was simple and classy, her jet black hair swept luxuriously over shoulders and her glinting eyes a well of elemental power, she pushed her retch-inducingly filthy shoes towards my face. I licked and worshipped every remnant of dog shit and kebab, every cigarette butt from her gorgeous shoes. I writhed with pleasure as she rubbed them mercilessly across my face and nipples. I gasped and begged for more as she kicked me and kicked me and kicked me. She smashed me in the side, in the stomach in the balls. I eagerly sniffed and sucked my own cum from her shoes and felt rightly humbled by the honour of being her kick bag and the privilege of being allowed to pay to clean her shoes. Turning with a smile Mistress retrieved something from a container, facing me she showed me what she held in her now glove shielded hands. A condom filled with the jolly consequence of another mans pleasure. Although slightly alarmed somewhere deep within my psyche, my hard-on was raging, my blood was up and my desperation was to serve. Trapped beneath her shoes I watched and listened silently to her orders. Cum drizzled out of the condom, all over the shiny toe of her shoes, a little on my chin, most down the soles of both of her shoes. Then the shoes were upon my tongue, then pushing, raspingly deep in my mouth as deep as she could push that shoe!

And I tasted it, not another guys cum but the elixir of service and submission to a dominant, naturally incredible woman. I licked and sucked eagerly at every last drop and then afterwards, panting, I responded to mistress’s inquiry with a simple ‘Thank you.’ She then dangled the spent condom before my eyes, inches from my wanton mouth, it glistened with residue, she placed it between my eager lips and instructed me to suck and lick and I sucked everything I could from within, her shoes ground and rasped red crop circles across my naked chest and one pressed and pressured upon my aching penis and balls. I looked past the condom to Mistress’s delighted smile

“Slut” she said, “you are going to be my Slut. You are a filthy, cum loving loser”. And this was the start.

The next session, it was two condoms and the session after a three. Mistress and I no longer communicated about the content of our sessions. I just turned up and obeyed and everything was perfect , as if in seamless synthesis. Her emails were playful and controlling. Teasing and inspiring. All I wanted to do was serve and my boundaries and limits were being broken and stretched with every visit. I called it communion, going for my Holy communion with Mistress. Seeing her, existing as part of her incredible life took on a religious intensity.

A month or so after my original cum guzzling incident I arrived for my session and Mistress, garbed in a gorgeous red knee length dress, handed me a little, Zorro-esque eye mask. I thought I looked dashing, she just laughed and said she’d brand a ‘Z’ on my chest for me with her heel later. Mistress left the room and returned a few minutes later with another man, who was naked but for a hood with eyelets. As soon as he entered I knew what Mistress wanted of me, and got on my knees to obey. Needless as it was but sweet as Mistress is and also due to the pleasure she derives from humiliating me, she still kept up a scathing, humiliating verbal commentary. A flow of orders from her cultured tongue. I listened obeyed and did as she taught me to do. I bought the man to arousal and then I licked and sucked his cock as she ordered. After probably twenty minutes I knew he was going to cum. Mistress knew too.

“Swallow it all slut, then lick it clear” she ordered “take it as deep as you can”, and I did. After the guy had left the room, mistress left me for a minutes with strict instructions not to move, I didn’t. When she returned she manacled my hands and feet and proceeded to scratch deep red, rents into my skin. A complex ‘Z’ I assumed in my agony, trying not to scream or shout. Wow, she’s going deep this time I thought. I realised I had squeezed my eyes shut to somehow ward off the pain.

“Open your eyes Slut” Mistress smirked “and suck my heel”. I opened my eyes and guided my lips to her heel, sucking as required, as lustily as I could as if it would distract from the pain of my chest and stomach. I tasted the dull metallic flavour of blood and looked with horror at my chest. Mistress started laughing deeply and genuinely amusedly. She had scratched ‘Slut’ on my chest and stomach, deep enough that I thought it might give a small scar - the kind that lasts for a half year.

“Relax slut, it’ll go down in a couple of months” she giggled “you’re mine now anyway and I’ve got big plans for you!” I peered up at her eyes, utterly humiliated, “now” she said, placing her heels in my nipples, standing full weight upon me twisting slightly every now and again. “If you’re going to cum then you’ve got 1 min, I’m timing you, if you’re not done by then, then bad luck, I’m going to lunch” With a vicious and skin tearing twist of her heels, she looked at her watch “50 seconds” she looked down smirking. It took another 20, so turned on was I by the utter humiliation and degradation I had experienced at my Owner’s hands. I licked that up too and my new life started.

Mistress began seeing me more often, I was tithing her by now, rather than tributing, but the depth of my submission had altered considerably over the course of a few weeks. Now I would turn up and three sometimes four different men would come for my cock sucking services. I was good and they seemed to enjoy Mistress ordering me around. Some didn’t and she left us alone. Mistress had advertised on a gay website and had offered prices for my services, which undercut everyone else. The novelty value of getting a blow-job from a straight guy induced hundreds to come. She was making a packet and told me so herself. I didn’t do ‘Cum In Mouth’ very often anymore, only when Mistress decided it was OK and with regular customers and boy, were there regulars. Kindly after every session Mistress would let me lick her shoes clean and would take the time to show me her cash and tell me what she was going to do with it. She particularly enjoyed telling me that she was putting my tithe up and that she found it hilarious and very sexy that I was worshipping her with a tithe and then spending 90% of our session time being pimping out for her profit! She was happy and I was happy and in a head-space where only sluts and slaves like me could be. Used, abused perhaps but really rather fulfilled.

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And now I was filled with a slight dread as Mistress approached, strap-on secured firmly about her waist, a grin on her face and plain delight in her eyes. This was to be the day that Mistress took my anal virginity. It was an important moment for me. I was giving this woman, this goddess everything of me and she had taken it happily and used it expertly. This was the final frontier of submission for me. I knew also that thereafter I would be feeling many real cocks inside me. A select group of my blowjob regulars were going to be allowed to fuck me too. Mistress had broken me in the gentlest of ways and now I am addicted to serving her and being used for her gain. As she nears I raise my knees above my head and look through my legs at my Goddess’s approach. She pushes the lubricated giant at me. Then I feel a deep warm, electric feeling boring inside me. Physically a culmination of a month or so of training with various butt plugs and months of psychological training from Mistress. The physical sensation whilst incredible was an absolute second to the torrent and tumult of emotions raging inside my quivering body.