Maid to Pay (F-dom, Sissy, Gambling Debt) Maid to Pay Damned, the pressure was building. I knew I had a problem with gambling, but I couldn't shake the disease. The more I fought it, the more I would wind up increasing my debts...so much so, that I was beginning to worry about some goon knocking on my door to explain orthopedic procedures, concerning my kneecaps, to me. Let me tell you more about myself. I am an average guy in his middle 30's with a beautiful wife, two wonderful children and a very successful job. I am not bad to look at, and have a normal sex life. In short, I had it all - but I also had a terrible disease. The disease was called gambling. I knew how stupid it was, building up large debts to very unsavory people. I had tried counselling, gamblers anonymous and all the other things that guys like me try, but to no avail. Fortunately, because of my income level, I had successfully hid my problem from my wife and my employer. However, that was becoming more and more difficult, and it was inevitable that someone was going to find out. I was becoming a nervous wreck! Then one morning, I received a phone call that was to cure my addiction completely. As I answered the phone, a gruff voice came on the line. "I want you to call 555-3421 immediately", the unidentified voice said, "You will make an appointment with Ms. Elaine to discuss ways for you to eliminate the debt that you owe my organization. Do it now, or we will find less subtle ways to eradicate what you owe us!".The caller then abruptly hung up. With my voice quavering, I did as I had been instructed. When a very sultry female voice answered, I identified myself and asked for Ms. Elaine. "Oh yes, Charles, I have been expecting your call" the voice on the other end of the line replied, "please be at my office at 3:30 this afternoon". Ms. Elaine then gave me the address and admonished me, "Charles, please do not be late. You are in very serious trouble, in fact life-threatening trouble, and I am your only hope in helping you extricate yourself from that trouble". Stammering, I assured Ms. Elaine that I would be there, and on time. The rest of the morning seemed to drag on, but I made it through, grabbed lunch, and left a little early to insure that I would not be late for my appointment. The address turned out to be a prestigious high-rise apartment building. I took the elevator to the penthouse apartment and knocked on the door. As the door opened a man, obviously the butler, ushered me in. He told to sit down and be comfortable , and Ms. Elaine would be right with me. As I sat there, a nervous wreck, I noticed magazines lying on the coffee table. They were very bizarre - all seemed to be centered on the same theme, that of female domination. As I looked at the magazines, Ms. Elaine walked into the living room. "Hello Charles, I see you have noticed my magazines. I hope you like them". I was astounded! She was absolutely stunning, with dark chestnut hair, deep brown eyes and dressed in a leather mini skirt, a red satin blouse and VERY high black patent leather heels. "Well, Charles, you seem to have a problem with a certain organization, and they have enlisted my assistance in liquidating the very large debt you have accrued. Do you wish my assistance, or would you prefer they take care of the situation in the 'old fashioned' manner which they are quite good at." My voice quivering, I started to talk. "Elaine, I would...." WHACK! My face stung, and I was shocked as she slapped my face. "DON"T YOU EVER PRESUME TO CALL ME ELAINE AGAIN", she screamed, "YOU ARE TO CALL ME MISTRESS ELAINE, AND WHAT I SAY, YOU WILL DO"! "Uh yes, Mistress Elaine", I stammered, "I shall do whatever you wish". Cowering under austere look, I felt like a little boy being reprimanded. Mistress Elaine then ordered me to lay face down on the coffee table. She slid my trousers and my briefs down and proceeded to cane my bottom until tears were streaming out of my eyes. "Mistress Elaine", I pleaded, "I will do anything you desire...ANYTHING... please don't let them hurt me"! "That's better, Charles", she cooed,"As you might be aware of by now, I am a professional dominatrix, and enjoy beating a submissive male's ass until it is nice and pink". "Mistress Elaine", I whimpered, "If your wish is for me to submit to your lash, I will be here whenever you order me to be here. I just want to pay off my debts and get rid of my gambling fever", I blurted out. "Silly boy", she exclaimed, "Do you honestly think you can work your debts off by submitting to my spanking! Men, more successful than you, pay me large sums of money, just for the privilege of kissing my heels and having me whip their asses red. What I need, is an assistant to add to the special needs a few of my more affluent clients have, and are willing to pay for". She continued, "I have a need for a french maid to help meet these special requirements, and you may be able to help me in filling this position!". "But Mistress Elaine", I exclaimed, "I don't know any women that would be suitable for this position"! "Oh Charles, you are so naive. YOU are ideal for the position, and I think you will just look too sexy and cute for words, by the time I am finished with you. Besides, those special clients I mentioned, will be willing to pay double the normal fee I charge them to have the maid assisting me." "From now on", she continued, "You are to plan on spending Tuesday, Wednesday and Thursday evenings here as my maid. You will simply have to tell your wife that you are travelling on business those three days, every week." She continued, "and, since this is Thursday, there is nor reason you shouldn't begin your new duties immediately!" Mistress Elaine then rang for the butler. As he entered the room, Mistress Elaine introduced me to him. "Robert, this is our new french-maid, Cissy". Robert looked at me with a big smile on his face. "Nice to meet you, Cissy, welcome to Mistress Elaine's team". I was totally humiliated, standing in front of Mistress Elaine, while this very masculine man referred to me as "Cissy". I stammered hello to Robert, my face burning in embarrassment. Mistress Elaine then put a collar around my neck, attached a leash to the collar and led me into her "studio". Robert accompanied us, all the while maintaining a leering grin on his face. Mistress Elaine's studio was equipped with all sorts of unusual devices, obviously constructed solely to restrain her clients in various positions. Mistress Elaine ordered me to the center of the studio. She ordered me to undress completely, while the butler continued observing my embarrassment. Mistress Elaine then cuffed my hands together. She then clipped the cuffs to a cable coming from the ceiling. Robert then drew the cable tight so that I was standing on my tip-toes, helpless and totally exposed. Mistress Elaine turned to the butler,"Robert, I have a client coming at 7:00 and another client at 10:00 tonight. They both have special requests and will pay double the normal rate. We have enough time to dress Cissy appropriately, but I will need your assistance." Robert shook his head in agreement. Mistress Elaine then took a bottle of depilatory and began to apply it to my entire body from the neck down. I was really embarrassed as she rubbed the lotion all over me..not missing a spot. As she smeared the lotion on my pubic area I started squirming in my restraints and cried out at the humiliation I was undergoing. WHACK! The sharp sting on my buttocks was like a hot iron, as Mistress Elaine applied her whip to me. Whack! Whack! "STOP YOUR SNIVELLING NOW, CISSY!", Mistress Elaine yelled at me, "This is just the beginning! You are going to be my resident party doll, and you will be as feminine as possible, yet everyone will still know that you are nothing more than a sissy boy, dedicated to pleasing me and my clients!". I stopped my squirming, knowing that I was helpless to prevent what was happening to me. Finally, she finished applying the depilatory lotion, and they both sat down waiting for lotion to do it's work. After fifteen minutes, Mistress Elaine had Robert uncuff me and led me into the bath where she told me to rinse myself completely. Robert then handed me a towel and I dried myself completely. I was led back into the studio and again cuffed in the same position. Mistress Elaine the place a heavily boned red satin corset around my torso and snugged up the laces. She then had Robert tighten the laces until the corset was fully closed. It felt like my body was in a vise! I could hardly breathe! "Oh look at Cissy's cute little figure", exclaimed Mistress Elaine, "She is going to look so cute in her little uniform!" Mistress Elaine then slid sheer black, seamed stockings up my hairless legs and attached them to the garters on the corset. She then slid a pair of very frilly lacy black panties on me and a black lace bra. Robert placed a pair of silicone filled pads in the cups of the bra, while Mistress Elaine forced a pair of black patent high heel shoes on my feet. The shoes were murder!...the heels had to be 6" high and I found myself in great difficult just standing in them. I realized that I was going to have to walk in mincing little steps just to keep my balance! Robert then removed handcuffs. As I stood there heavily corseted, in panties, bra, stockings and high heels, I felt totally humiliated, my face burning in shame. "Oh isn't Cissy cute, Robert!" exclaimed Mistress Elaine, "Won't our clients just love the added pleasures that she is going to provide"! Mistress Elaine ordered me to mince around the studio as she and Robert went into hysterics, laughing at my degradation. "Enough playing", I have clients coming and I want to finish dressing Cissy appropriately", she said. She then ordered me to sit down, while she deftly applied foundation, blush and the proceeded to outline my eyes with jet black eyeliner. Several shades of blue eyeshadow were applied and a heavy application of bright red lipstick. Mistress Elaine then coated my fingernails with a bright red polish that matched my lipstick. She completed the make-up session by clipping a pair of large dangly earrings on me. "Stand up Cissy, let's see how you look", said Mistress Elaine. I did as she ordered, knowing what a sissy I looked like. Mistress Elaine then took out her camera. "A few pictures of you, before I place your wig on, posing, dressed as a sissy boy, will give me even more insurance that you will do as I say. "Click Click" - the sound of the camera brought tears of shame to my eyes. "Now, kneel down Cissy, I want a few more pictures of you ... with Robert in the photos as well". "No", I screamed, "Please not that"! Robert grabbed my arms and forced me to my knees. "Now, Cissy, is that anyway to treat poor Robert who has been so helpful in turning you into the sissy boy you really are?", said Mistress Elaine, "I think you should show your gratitude to him. Suck his cock now"! I was helpless! Robert unzipped his fly and I was shocked at the size of his penis. It had to be 10" long and very thick. With absolutely no foreplay, he thrust his cock past my lips into my mouth. Placing his hands behind my head, he forced himself deeply into me, fucking my mouth as if it were a hot vagina. I tried not to gag, and then I heard the sound of the camera again! "Oh no, she is taking pictures of me again", I thought, "She can blackmail me to do anything she wants me to do". Robert increased the tempo of his pumping. I could feel the head of his cock starting to throb, then Robert suddenly pulled his cock out of my mouth. Mistress Elaine quickly grabbed it and started pumping his cock, aiming it at my mouth. "Open wide, Cissy!", she said in a husky voice, "You are about to receive a nice hot load of cum, your first of many!" Robert suddenly moaned in ecstacy as she continued to pump his cock and then..the shock of hot sperm shooting on my face, t my lips, into my mouth and on my tounge. Mistress Elaine continued to aim his cock so not a drop was wasted, then thrust it back into my mouth, so it acted as a plug! Mistress Elaine started stroking my throat, as Robert continued to fill my mouth with his cum. "Swallow Cissy", she said in a taunting voice, "You are going to have get use to having men use your mouth as a sperm depository". Robert kept his cock in my mouth while Mistress Elaine continued stroking, until I swallowed every drop of his cum. "Oooooo, very good, Cissy", squealed Mistress Elaine, "I am sure that will you become a superb cocksucker and my clients will be delighted to pay extra for your services"! Mistress Elaine then ordered me to sit at the make up table again. She freshened my lipstick, then placed a long, chestnut brown wig on my had, teasing it and adjusting it until she was satisfied. Finally, she slipped two frothy taffeta petticoats over my legs and up to my waist. Then came the uniform. It was black satin, trimmed around the sleeves and the bodice in white lace. The skirt was very short and it stood out almost straight from the petticoats underneath. A white lacy apron and little hat added the finishing touches. As I looked in the mirror, I was amazed! The addition of the wig, coupled with the french maid uniform, made me look very sexy indeed! Mistress Elaine grabbed my hand and led me to the living room. "Cissy, I have two clients tonight. The first, Mr. Lane, will be here in about 20 minutes.Mr. Lane has a craving to be dominated and humiliated. You will assist me in his humiliation. He will be restrained, and as he becomes aroused from the taste of my paddle, you - my little sissy boy - will caress him, and tease him by rubbing your satin clad body against him." " When he becomes really hard, you will kneel before him and start sucking and licking his cock, as I continue spanking him." "Just before he cums, I shall remove your wig so he will experience increased humiliation receiving a blow-job from a sissy boy in petticoats." "For his ultimate humiliation, I shall hook you to his crotch harness to he will not be able to pull his cock out of your sissy mouth, while I spank him to a second orgasm!" Mistress Elaine continued, "My second client , Gary Davis,is exactly the opposite. He is quite dominant and has the fantasy of humiliating and degrading his tyrannical boss.I will play the role of his secretary, and you, my dear Cissy, will play the role of his boss!" "As part of the scenario, I have blackmailed his boss into doing anything I want him to do. When Gary walks in, you will be dressed in a frilly pink taffeta party dress, little pink bows in your hair, and frilly pink panties but with high heels and nylons - so you are a hooker's parody of a little girl! Gary intends to have me restrain you so he can fuck your lipsticked mouth and jerk off on your face while I take photos for him to show the girls at the office". You will be our total sissy toy to play with,to be used and humiliated as we see fit. Since he is the last client of the evening, and tips me quite will, you may find yourself spending a great deal of time tonight, with your lips wrapped around his cock!! As I sat there, waiting for Mistress Elaine's first client of the evening, I felt trapped. I knew that I had to do exactly what Mistress Elaine ordered me to do, and that most of those things were going to be extremely humiliating. I was now her sissy boy, her french-maid, her submissive little girl, and, worst of all, her sissy cocksucker.