My Life with Mistress Pt. 01

"This is Jeffery; he has yet to sample the pleasures of a woman. I wonder if you would have an interest in helping me give him a demonstration in the arts."

As she talked, she continued to stroke the man genitals and soon his erection was obvious and as aroused as he seemed to be it was no surprise when he readily agreed. She stood, took his arm, and instructed me to follow. On the elevator to our deck, Mistress allowed him liberties that I had only dreamed of and at one time, he even had her breasts exposed as he rudely pulled her top down. As he had his lips on her nipple, she caressed his head and I saw her whispering in his ear. He stopped and turned to look at me and then with a leer told Mistress, "Why not."

As we entered our cabin, Mistress turned to me, and instructed me to kneel in front of her soon to be paramour.

"Jeffery, I want you to get a close look at what a real man looks like. Now pull his suit down, go ahead do what I tell you."

I did as instructed and I recoiled with horror as his rigid manhood jumped out at me from his suit. Both of them laughed at me for my timorous reaction and then Mistress gently guided my head closer for a better look. I had never seen an uncircumcised penis before and when Mistress pulled back his foreskin, I was shocked how red and angry the bulbous end looked. Now Mistress had my head in one hand and his monster in the other. To my utter humiliation, she began to tap his member on my lips and I could feel the wetness of his prepublication on my mouth and chin.

"Now Jeffy, I want you to take my friend in your mouth to get him wet so he won't tear me open with is huge cock, OK open up, that's a good boy."

I could not displease my Mistress so I opened up and put just the end in my mouth. The head had a vile tasting substance on it and I suspected that he did not practice diligence with his hygiene. I did my best to cleanse him with my tongue, as I didn't want him to get his stink on my Queen. Without warning, he grabbed my head and brutally shoved his shaft down my throat and he held me in place. I began to gag and retch at the same time, I couldn't seem to breathe, and then this wretched man began to ejaculate in my mouth. Then as a way of further humiliating me, he pulled his horrid thing out of my gaping mouth and finished delivering his vile spunk in my face. In an even worse mortification, Mistress was now angry with me.

"Boy how could you do that, just how is this gentleman going to please me if you suck the spirit right out of him. Look at this poor limp dick, can't you do anything right?"

The sting of her words far outweighed the degradation I had felt at the hands of this man and in a show of appeasement; I once again picked up his soft member and put it to my lips. As I tried what I could to help him regain his vigor, I realized how inexperienced I was in such things and so I tried to visualize in my mind what would please me. I looked to see Mistress go sit in her chair with a look that could only be called a snit, so I knew it was up to me to return his member to a turgescent state. I first skinned him back as I had witnessed Mistress and then impishly I kissed the very tip. I proceeded to lick underneath and along his shaft and I must say that with pride I felt the first twitch of desire returning to him. He began to grow firm in my mouth and yet still soft enough that I was easily able take him all. With another stroke of insightfulness, I began to caress his testes as I worked his member with my mouth and tongue. I was concentrating so much at what I was doing I didn't even notice he was now fully erect and it was not until I heard him moan that I realized I had successfully returned him to rigid and ready. I took him out of my mouth and with some pride I announced,

"Mistress your man is now ready for you."

I helped her off with her swimsuit and she laid down on the bed with open arms and legs for her lover. Her last instruction to me was to stay close and watch which I did with pleasure. He lay down on top of her and I saw her hold him to help guide him into her slit. He attacked savagely as he pistoned fast and hard inside her. He repeatedly bit her on the neck and upper breast and yet Mistress kept yelling for more as she wrapped her legs around his torso. She dug her nails deep in his back, even drawing blood from some of the scratches. To me it was horrifying to watch yet I couldn't turn away. It was easy to tell when he had spilled his seed deep inside her; it was as if the life had been drained from his body through his penis. He flopped off her and seemly in seconds he was fast asleep, snoring loudly.

I quietly assisted Mistress off the bed and into the bathroom for clean up. She first used the facilities and then it was my duty to clean up his slime mixed with her golden nectar. As she was so abused, I had to take great care for she was raw and sore and I didn't want to cause her anymore pain. I drew a bath and assisted her into it and she relaxed and let the discomfort soak away.

"Mistress may I ask why you would let such a brute defile you in that way?"

"Jeffery he is a man and I am a woman and from time to time I enjoy the pleasures only a real man can give me."

"But I could never act like that, to just take what I want from you or any woman..."

"Shush, you don't need to worry about that, I don't think of you as a man but as my sexual servant and I would never expect you to be able to act as he did."

When she was finished, we went back out to the sitting room and the man had left, without even a note. I helped Mistress dress, this always gives me so much pleasure, first because I am helping Mistress to look beautiful and with her sweet surrender to my touches and caresses as I put on her intimates and nylons it as if a balm to my soul. The total eroticism of being so close to madam that I can actually inhale her aroma both natural and whatever scent she chooses to wear. While I was working so diligently with her precious nylons, ever careful not to snag as I slid them up her well turned legs we began to converse almost like a couple.

"Mistress, do you think I will ever earn the privilege of you making a man out of me?"

I believe her mind was elsewhere and she failed to understand my quarry.

"Boy, whatever are you talking about? Oh you want to know if I will ever fuck you."

I believe Mistress used those crass words to shock me for a lady would never talk in the vernacular like that. She went on,

"I doubt that I would ever fuck you, your dick's just too small but if I think you have earned it I might have someone I know make a man out of you." At that, she started to laugh,

"No, I take that back you'll never be a man but let's just say I'll get her to take your cherry."

Wasn't that just like my Mistress, even when she's doing something for me she still manages to humiliate me at the same time.

Part 4: Jeffery learns the pleasures of ladies undergarments plus the discomfort of milking. The ship returns, Mistress meets mother and the three settle into a relationship.

At diner, we learned the ship would be docking the next day. It was so hard to believe that just a few short days ago, I was praying for the cruise to be over and now I am both surprised and disappointed to hear the end is near. I watched Mistress eat heartily but I could not for I was now full of apprehension. Would this be the end of Mistress and I, was I nothing more than a shipboard dalliance or worse merely someone to toy with then to cast aside once upon the land. Did Mistress not know I was hopelessly in awe of her beauty and stature? I wanted to know but I feared the answer so I said nothing. After dinning Mistress said she was going to the ballroom and that I was to return to our suite but not to wait up. As if I could sleep while worrying as to her safety.

Back in our room I busied myself with packing, first mine as it was the easiest and then with Mistress. The joy of touching her things without the worry of her discovering me was pure bliss. First, it was the elegant touch of a slip on my cheek and then as I lewdly put my face in a pair of her delicate panties I got an urge I couldn't resist. I quickly undressed down to my cage and then slipped the panties up my legs. It was the naughtiest of feelings, the closest to heaven I've ever been. I looked in the mirror and saw that with my cage in her panties I looked more as woman than a man. I put my head in her slip letting it caress my body as it slithered down. I thought about a bra but with Mistress' enormous breasts, my flat chest would look silly. The feel of all this silky material was almost too much to bear and I could feel my penis struggling for freedom from its cage.

I don't know where the ideal came from but I went to the credenza and took one of the unburned candles from a drawer. I went to the bed and crawled up on my hands and knees. I pulled Mistress's panties down to my knees and then began to insert the candle in my rectum but found that without moisture it was difficult. I remembered Mistress instructing me to moisten her lover's member with my mouth so I took the candle and began sucking and slobbering on it. It was only then that I noticed the candle was black and I began to fantasize about a strong Negro taking me for his pleasure. I retried the candle in my anus and with the saliva coating it slipped in rather easily.

With my eyes closed and my thoughts on my buck, I failed to notice Mistress had returned. When I heard movement, I opened my eyes to see her watching me with what looked like a smile on her face. I froze not knowing what to do, she said,

"Don't stop boy I want to watch, in fact I'll help."

She slapped my hand away and began to assault my bottom vigorously with my imaginary black lover. Oh god, it felt so good, where as I had tried to be gentle she was using me as her lover used her and it was then I understood what she talked about in the bath earlier. I began to feel strange as Mistress held my testicles in one hand while she kept up her battering of my rectum. Suddenly I felt wetness on my thigh, and when I looked down, I could see what looked like semen emitting from the end of my penis. It looked like semen but it didn't feel as if I was experiencing a climax. When the fluids stopped their seepage, I still felt that yearning that I'd had since Mistress stopped me from masturbating a few days before.

"Jeffery I should be angry with you for wearing my clothes but what the hell it was fun watching you try to fuck yourself with a candle and besides you look good in my panties. From now on every night when I go to bed, I'll take my panties off and then you can wear them. After you wear them, you will launder them for me."

I couldn't help it I began to cry,

"Mistress does this mean I can stay with you after we get back to shore?"

"Oh yes Jeffery, you're a keeper. You'll be around for quite a while till I tire of you."

I got down on my knees in front of her tears still streaming down my face as I hugged her around the thighs.

"OK now boy you had your fun now come do your clean up chore on me, I am a mess; I shouldn't do two guys at a time, when will I ever learn."

Mistress was a mess and just like me, she had something in her rectum, for it was full of gooey white jism as was her delicate inter folds. I went to work on what become a supreme joy, not the eating of her lovers vile spunk but the cleansing of my Goddess. As always, as I kept my face buried in her, she would stroke my hair and tell me stories of her lover's manhood and of their ability to bring pleasure to her. Although this made my heartache as I realized this was something I would never be able to do, in the end I would be glad because of the enjoyment she received from her ruttings.

The next day as we waited for our ship to come to port Mistress asked me where I resided. I told her I lived with mother and the location of her manner and was taken aback when she said she would like to meet her. I hadn't thought of this, just how mother and Mistress would get along. They were both strong willed persons and expected to get their way and if there were to be a clash of wills I could not predict who would come out on top and yet no matter what I knew I would suffer. Once ashore and in a cab loaded with both of our luggage Mistress informed me that I would be allowed to address her by her given name while in the presence of mother. She further instructed me not to abuse the privilege and only to use Veronica when prudent. I looked up to see the cab driver in his mirror and I could see he was sneering distastefully at me but at the time, I was more worried about how mother and Mistress could coexist. What I was soon to learn that much like powerful nations, people of strong but equal wills learn to negotiate a workable peace.

Upon entering the manor we went to mother's chair and my exact words were,

"Mother this is Veronica Marsh..."

Before I had the chance to introduce mother Mistress extended her hand and said,

"It is a pleasure to meet you Mrs. McDonald."

"My name is Spence, Miss. Spence, I refused to marry Jeffery's father. The man was a sex addict, just like his son here. Every time I couldn't find that boy, I knew he'd be up in his bath abusing himself. Filthy habit and I never found a way to cure him of it."

I said, "Mother would you please stop talking like that."

Both women at the same time said, "Hush boy," and then they turned and smiled at each other. I believe this made a bond between them,

"My dear Miss. Spence you are such a delight and so young to have a boy Jeffrey's age."

"Well, yes, the sins of the young and all that, I had him when I was still in school."

"If you're still interested I have found a way to prevent this boy from abusing himself."

"Oh yes I'd love to see that."

"Jeffery pull down your pants and show your mother your new device."

I couldn't believe my ears; I couldn't do that in front of mother.

"Don't dilly-dally do as the young lady tells you, would like me to take you over my knee?"

What do they call it, 'The horns of a dilemma,' I believe, what would be more humiliating, being spanked as a schoolboy in front of Mistress, or to expose my caged genitals to my mother? In the end, the choice was not mine to make as mother yanked open my trousers and pulled my pants down to my knees.

"What is this?"

Oh my god, I forgot I was wearing Mistress' unmentionables.

"That's nothing but a silly game that the boy likes to play with my panties."

"You allow him to get his filth all over your undergarments?"

"Only with the condition he launders them after, oh he also can only wear them after I have. All right Jeffry now pull down my panties and show your mom what you are wearing."

She went on to show off my cage to mother and both were handling my privates as if they were looking at a flower or maybe a piece of fruit still on the vine. She went on to show mother the key hanging around her neck.

"Are you concerned that without release his little nut sack will back up causing, what do they call it, blue ball?"

"The boy and I worked on that the other day, if you would like to see it, all we need is a long candle and of course something to catch his spillage."

Mistress went on to describe the procedure leaving out no detail. How could she possible think of violating my bum in front of mother?

"Miss. Marsh if you will accompany me to my bedroom I think I might just have the perfect implement for you. Jeffery you stay here until we return."

I can't tell you what I expected to see but when they came back, I was beyond shocked I was stunned. Mistress was naked and wearing a harness containing what appeared to be a large phallus shaped piece of black plastic.

"Jeffery isn't that sweet you mother has loaned us her personal dildoe to milk your prostrate. Assume the position."

This was not a request it was a command and I dared not disobey no matter how humiliating. With my face a bright crimson, I got on the floor on my hands and knees exposing my rectum to my mother. The only saving grace I received was at least I didn't have to put the devise in my mouth to lubricate because they used some mother had. Mother was a witness to the whole ordeal and once again, she and Mistress talked as if I were a pet or maybe livestock. Mother held my member in her hand to catch most of my discharge as it slowly seeped from me. She actually giggled as a schoolgirl when Mistress informed her I was then to ingest that which I had just expelled. She put her hand to my lips and I did as instructed.

I was next sent to my room so mother and Mistress could relax and have girl talk as mother called it. I felt as if I was being sent away as a schoolboy so the adults could talk in peace. At first, I sat on my bed pouting but in my room with all my books and things, I began to relax as I now was in my world. I took a copy of Keats from the shelf he is so comforting and I can read him knowing there will be no violent action but only soothing sonnets.

I must have drifted off to sleep for I woke to semi darkness and the sun almost set. I went to find the ladies but they were not in mother's sitting room. I heard a noise down the hall towards mother's bedroom and went to investigate. Her door although not shut was pushed closed. As a child, I was always instructed not to enter mother's bedroom if the door was shut and although it was not shut I had the distinct feeling I should not go in. However, my curiosity got the best of me and I had to take a peek. Inside were mother and Mistress, both naked, Mistress was still wearing the harness and was now fornicating with mother. Mistress's actions were so identical to the brute we had met on the ship I had to do double take. My own mother was wheezing and panting so hard it reminded me of a bitch in heat. Then finally, in the throes of orgasm, she begged Mistress to stop saying she couldn't take any more.

After that first day, the three of us settled quite comfortably into a relationship that would seem strange to the outside world. In public, it looked as if Veronica and I were lovers accompanied by my mother but in private it was my mother and my Mistress who were lovers and I merely a sexual servant to both. As the ladies hunger dictates Mistress will bring home various men to pleasure both her and mother and I am now required to clean both ladies. The oddity of it all is quite familiar to us now and although I'm still a virgin I'm as sexually satisfied as I could ever hope to be.