My First MilkingbyBakeboss©
When Mistress first put me into chastity, she said it was for a trail period. She soon found out it not only keeps me from abusing my worm while she is out it also keeps me more attentive to her needs. Another plus was that now I had to sit to pee, I have always had to relieve myself this way while Mistress was around, but she suspected when she was away I defied her by standing as I emptied my bladder. My one-week trial has now lasted for over a month and I fear it may go on forever.
The only drawback was the need for hygiene, Even though Mistress feels it is disgusting to touch my worm, she refuses to allow me to touch it myself. I am always manacled while my worm is uncaged because I can't be trusted. I know I am weak but after being confined and then to be in the hands of my wonderful Mistress I can't help it my nasty thing becomes erect. Not only is this habit repulsive to my queen it becomes a problem to put it back into its cage once the cleaning is done. The only answer seemed to be Mistress petting my worm until I deviled her palm with my slime. After cleaning Mistress' hand with my tongue she would then put me back in my cage until the next cleaning. Of course, I never told Mistress but this was always the high light of my week and just the anticipation would make my worm try to grow inside my cage.
That all changed the night she had Maxine with her servant over for cocktails. Mistress showed me off in my cage to Ms. Maxine and once again thanking her for informing her about the delights of male chastity. As Ms. Maxine toyed with my cage by pulling on it to make sure it was properly installed, Mistress mentioned my nasty habit of becoming erect upon release.
"Evelyn, you must try milking him before freeing him. I do this to this one all the time and not only does it insure he will remain flaccid during cleaning it has the added plus of giving him no pleasure while he is enduring the procedure."
This statement intrigued my Mistress and after accepting Ms. Maxine's offer to give her a demonstration, her servant was instructed to strip and assume the position.
Once naked I was quick to see how much abuse he had taken from Ms. Maxine. Even though I knew we both to be twenty years of age this boy looked old for his age. I hoped they didn't see my shudder as I noticed all the stripes across his backside. Once again, I was thankful to belong to my Mistress instead of someone like Ms. Maxine. We watched as the servant got on his knees and then leaned forward until his head was on the floor and his derrière was in the air. He used his hands to spread his rump apart thus exposing his anus.
"My boy is quite familiar to this and is required to keep his anus spotless, I need only use my finger to milk him. As your boy is new to this regimen, I would advise using one of the many tools they have for this treatment. You may also wish to use some kind of lube to ease the discomfort but I never bother. Now watch as I insert my finger into him, you see I search for his prostate by probing deep. Ah see that flinch he just made, that is how you know when you find it."
At this point, she asked for a saucer then she placed it under him and as we listened to his moans, we saw a clear discharge begin to dribble from the end of his cage. The servant began to rut like a bitch in heat but a slap on his backside stopped this disgusting behavior. Once he had ceased discharging, he automatically lapped what was on the saucer.
The next day my Mistress came home with a devise called an 'Aneros Prostate Massager' and a smile on her face. I had already been instructed to give myself as many enemas as it took to assure a clean anal tract. As I am always naked in the presence of my Mistress all that remained for me to do was to 'Assume the Position' as we had been shown the night before. I felt the trickle of the lube first and gave a prayer of thanks she had decided not to penetrate me dry. I think more as a sign of submission than anything else Mistress had me kiss the device first and then to wet it with my mouth. The look of the Aneros was both erotic and scary and I have to admit I was nervous about what was about to happen to me.
As my Mistress has violated my backside many times I had no doubt the tool would fit but I was concerned about the pressure the Aneros was giving me as it filled my passage. As soon as the tool found my prostate all thought of discomfort were forgotten as the surges of pleasure shot to my groin. It wasn't until I received a slap on my butt did I realize I too was rutting just as the lad the night before. With my head on the bed looking between my legs, I began to see my issue dripping from my cage but I was not receiving the relief I normally get from an orgasm. My groin still throbbed as the last of my discharge dripped onto the saucer under me. I did not need instructions to perform my next task, as I licked my saucer of 'cream' as a cat would. With the Aneros still violating my rectum I was instructed to lie on my back and put my legs over my head. In this position, Mistress continued my massage and now she was able to watch my discomfort as I tried to control my urges during the procedure.
Only after repeated probes and no further discharges did Mistress remove the Aneros from my backside. She now felt free to remove my cage without restraining my hands and thus my hygiene became my responsibility. Now my little worm is so soft and spent I can do nothing but clean it and await a return to my cage.
I am milked regularly now and although it is both humiliating and uncomfortable, it is something to which I look forward to receiving. Although it is not what I would call enjoyable, it does relieve the pressure and as always, I relish any attention from my Mistress.