Although I continue to receive some demeaning and aggressive comments, most feedback has been positive. I appreciate all who enjoy this story, as we share similar fetishes. If you are not interested in FemDom, male feminization, and sexual humiliation, do not bother to read this series.
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I was standing with my petticoat and the skirt of the maid's uniform held up to my waist and my panties were down around my ankles. My cock was erect as I stood before Ms. Panington waiting for further instructions. I knew that she planned to put me in some sort of penis extender device, and I felt particularly embarrassed about my erection of less than four inches.
"Remain standing just as you are, Tom," Ms. Panington instructed, "I want you to meet your trainer." And she walked back to her office momentarily, returning with the Dominatrix in tow.
"I know the two of you have not been formerly introduced, although Madam Christina has witnessed some of your humiliation," she paused as Madam Christina walked over to me and put a black-gloved hand on my penis. "Tom, this is Madam Christina. Madam Christina, I believe you already know this is the compulsive masturbator and sissy that you will be training."
Madam Christina stroked me sensuously as she grinned mischievously, "Oh yes, I witnessed this one being changed by Nurse Pyre. I think we'll get along just fine." And with that she dropped her hand to my balls and gave them a sharp squeeze.
"I will leave the two of you to get acquainted then and to begin Tom's sexual service training," Ms. Panington concluded, then turned and left the room, closing the door to her office behind her.
Madam Christina left no time establishing her authority. "On your knees, jerk-off! Keep your skirt and petticoat up. I want to see that cute little appendage you have that brings you so much pleasure, but has gotten you in so much trouble."
She stood before me as I knelt. I felt myself trembling in her presence. I looked downward out of deference. She grabbed my hair, abruptly pulling up my face to look at her. "You may look, but you may not touch." I gazed up at her beauty. Blonde and buxom, she was wearing a black bustier, black choker, form-fitting black leather pencil skirt that stopped just short of her stiletto thigh high black boots. She was nothing short of stunning. "Do you find me attractive, sissy?" she asked.
"Yes, Ma'am, very much so. You are beautiful, Madam Christina," I responded with a faint, trembling voice.
"And your wife, Kelli, she is beautiful as well. I met her when she was here and I reviewed the training regimen with her. You know, Tom, you are lucky to have her. She has been so patient with you. She deserves better than you sneaking around and masturbating in her panties, don't you think?"
"Yes, Ma'am, she does deserve better and I am lucky that she is giving me this opportunity to become a better lover," I ventured as Madam Christina let go of my hair and I again bowed my head in deference.
"Now, Tom, I am going to teach you how to fuck Kelli like a woman deserves to be fucked. Poor woman, she has tolerated your inadequate efforts for years and she deserves better," she walked to a cabinet and returned with a flesh-colored phallus. "First we will get the penis sheath on you and then you can show me your stuff with old Dolly here," she laughed.
"Stand up," and she seated herself, "Over here in front of me. Turn around." She unlocked the padlock on the collar of my dress. "Off with the dress and your frilly petticoat, sissy. It will only get in the way." I fumbled to unzip and step out of the satin maid's dress and white petticoat as Madam Christina sensuously stroked the eight-inch penis extender. "Let's get this on you."
I did as instructed and she showed me the realistic-looking flesh-colored dildo with a sturdy silicone loop at the bottom. Sturdy nylon straps extended from each side of the loop. "This has been custom-fitted for your small penis, Tom. I think you will find that it is easier to put on when you are erect, like now," and she teasingly flicked my cock for emphasis.
"But it can be attached over a flaccid penis as well. I am going to put it on you just this first time." She took the arousal sensor off of my penis, then continued, "Pay attention as you will be expected to know how to do it yourself."
Madam Christina grabbed the base of my dick with one hand and, moving the silicone loop to one side, she slid the sheath over my penis. Then she took my balls and pulled them, one at a time, through the silicone loop so that the sheath was firmly in place. Then she took each strap and pulled them behind me and attached them to one another with Velcro.
It felt snug, but cold and my penis began to shrivel.
"Now look at yourself in the mirror, Tom. Did you ever think it was possible for a sissy like you to have an 8 inch cock?" Madam Christina taunted. "It won't matter to Kelli whether you are hard or soft, and it won't much matter to you either because you won't be able to feel any stimulation," she seemed to find this particularly amusing.
"Kelli won't have to worry about you prematurely ejaculating, and even though it will be you doing the fucking, Tom, she will have the sensation of being fucked with a real manly cock. Aren't you happy for your wife, Tom?"
"Yes, Madam Christina, she deserves it," I replied.
"Okay, let's get to work teaching you how to fuck a woman. This will be the first time that you have a cock that doesn't squirt as soon as it enters a pussy. Looks like Dolly is ready if you are, Tom," and she laughed wickedly.