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.
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 escort ankara 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.
This training station contained a twin size mattress. The plastic fuck-toy, Dolly, was perched provocatively with legs spread and knees up. Realistic-looking breasts projected at least six inches. The doll’s pussy had a faint patch of neatly groomed hair, and the labia glistened with some kind of lubricant.
“Dolly is ready for you, sissy,” and Madam Christina pointed to her love nest. “Kiss it, Tom, and ask Dolly for permission to service her.”
Feeling foolish kissing a plastic pussy, but wanting to get on with the training and fearing Madam Christina’s disapproval, I complied. “May I service your pussy with my cock, Dolly?” I ventured, nervously.
“Wait a second, Pantyboy, it’s not really ‘your’ cock, now is it? Listen carefully to what I want you to say, and this is what you will say to Kelli when you have the opportunity to service her,” she paused for effect.
“Now repeat after me, ‘I know that my cock is inadequate to properly satisfy you. And I know that it is not worthy to experience your pussy. May I be allowed the privilege of servicing you with my penis extension?’ Say it, Tom!”
Humiliated, I lay between the legs of this plastic representation of a woman with my lips just inches from the plastic pussy I was about to fuck with the humiliating penis extension. With halting speech I repeated just what Madam Christina had taught me, “Dolly, I know that my cock…”
“Very good, Tom. You are a quick study,” she laughed. Now before you enter Dolly with your fake cock, Tom, I will explain what you will see on the monitor,” and she flicked it on. The 40-inch monitor was mounted on the wall just above where Dolly’s plastic head lay on a pillow. “First, on this side of the screen, you will see this graph and this black line will indicate your stimulation of the arousal sensors in Dolly’s vaginal canal and clitoris.” I looked at the numbers ranging from one to ten on the side of the graph.
“Your goal is to maintain a high level of arousal, and eventually to give Dolly an orgasm. These lights will flash when you achieve that, Tom, and Dolly will squeal like, well, you’ll see.”
I focused on the graph and just as I was thinking that this was all very clinical and not very sexy Madam Christina hit some keys on a keyboard and the monitor screen was split, and I was dumbfounded to see, in freeze-frame, a glisteningly wet pussy that, unmistakably, was Kelli’s.
“Yes, Tom, it is Kelli. She allowed us to video-tape her masturbating while she was here. She agreed that it would motivate escort mersin you. You will be allowed to view her pussy as you fuck Dolly. If you succeed in making Dolly cum then you will be rewarded with video of Kelli’s face in orgasmic ecstasy.” I was spellbound with the image.
“Since she told us that you never succeeded in giving her such pleasure with your cock, I’m sure you’ve never seen her experience such pleasure. She told us that your face was always buried between her legs whenever she really got off.”
Madam Christina seemed to find this exceedingly funny, and laughed so hard she had to stop to catch her breathe. “She told all of us here that she has only orgasmed with your face buried deep between her legs or when your tongue has been in her ass.”
She reached into a bag she’d brought with her and produced a pair of the ‘mommy panties.’ “I know that you like these, Tom, and Kelli wore them for two days and nights without showering. I am going to keep them in the ziplock, but once you have Dolly consistently at 7.5 on the graph, I’ll put them over your head. Would you like that, Tom?”
“Yes, Madam Christina, very much,” I said.
“Okay, let’s take it from the top. Kiss Dolly’s pussy and ask for permission to service her with your penis extension. Then you may mount her.”
I did as I was told, then tentatively lay on top of Dolly. I couldn’t feel my cock, but I could sense that it was erect. I fumbled to insert my artificial cock into the artificial pussy, and I missed the target entirely with the first couple efforts. Madam Christina hooted with laughter, then sharply spanked my ass, “Not used to having eight inches, huh sissy? We’re going to have to practice your aim. Women don’t like a man fumbling like a virgin.”
Finally I found the opening and I began to push in. The plastic pussy offered moderate resistance, but soon I could feel that I had succeeded in plunging the entire length into Dolly’s pussy. The monitor lit up, and I could see that the entry had spiked the arousal monitor to 60. Then the freeze-frame of Kelli’s pussy began streaming and I could see her well-manicured fingers plying her pussy lips with abandon.
I was so aroused at this image that I feared that I would ejaculate, even without any sensation of stimulation to my cock.
“Oh, Madam Christina, seeing Kelli’s pussy is…oh…I’m, I’m, I’m worried that I might cum.”
Suddenly I felt a sharp pain on my buttocks, then heard the swish of Madam’s cat’o’nine tails. “Do not cum without permission, sissy, or I will have Ms Panington call Nurse Pyre to bring you back to the nursery. You must learn control and learn to at least fuck like a man,” Madam Christina shouted in my ear.
That quickly settled the pressure in my loins and I returned from the edge, but remained mesmerized watching the video of Kelli playing with herself, knowing that she had often done so in order to achieve satisfaction after I had lost my load early in our lovemaking.
I tried to settle into a rhythmic thrust and withdrawal, but soon Madam Christina was criticizing my technique and I could see that the numbers on the graph had fallen below 4.
“You are fucking like a machine. No woman wants that. Vary your speed; vary the length of your thrusts. That’s it. Sometimes leave it deep inside her, picture the fake cock touching the tip of her cervix, grind into her clitoris, watch the monitor, when you see what makes the numbers jump, do more of that.”
I tried to focus, more deliberately fucking than I had ever done before. I thought about what would stimulate Dolly’s arousal sensors, knowing that they had been designed after Kelli’s own anatomy. I was rewarded with the numbers going up, now consistently over 6, sometimes reaching 7.5.
“Good sissy, good sissy,” Madam Christina was now saying softly. I almost lost my load for a second time when I felt her pull Kelli’s soiled panties over my head and position the gusset just over my now. Soon I was delirious with Kelli’s scent and enjoying the sensation of thrusting.
Madam Christina instructed me to sometimes hold the fake cock in izle place deep in the pussy and to simply wiggle my ass. Doing so seemed to keep Dolly’s arousal solidly in the upper range.
“Okay, she’s ready. Now fuck her hard. Keep fucking deep thrusts until she cums. Yes, yes, you almost have it. Keep it going. Fuck, sissy, fuck!”
All at once the graph spiked to 10, Dolly let out a guttural squeal, and the video of Kelli switched to her face contorted in orgasmic pleasure. I felt a tremendous sense of accomplishment.
“Good for you, sissy Tom. The first orgasm you have ever provided through fucking. Okay, you may withdraw.”
As I pulled out the extender sheath, the screen went black. I was covered in sweat. Kelli’s panties remained over my head with the gusset carefully taped over my nose. My nostrils continued to be intoxicated with her scent.
“You may stand up, Tom. But first thank Dolly for the privilege of servicing her and kiss her pussy like a good sissy,” Madam Christina said in a comforting tone. “Isn’t it wonderful to know that you can do it, Tom? A little more practice, though, I want you to be able to get Dolly off without my coaching you.”
I kissed Dolly’s plastic pussy and foolishly thanked the plastic doll, then I turned to Madam Christina, “Thanks so much for teaching me. It will be wonderful to be able to fuck Kelli to an orgasm.” And I meant it.
My panties remained in place with the front pulled down just below my sack and my ass covered in silky pink. My breast forms had been dislodged slightly and I reached to adjust them in my bra. I looked in the full-length mirror and saw how my garter belt framed my penis extension and made it appear even larger and even more out-of-place. My stockings and heels completed the outfit and I teetered a bit as I stood.
“Get your bearings, Tom. We’re going next door to tell Ms. Panington of your accomplishment.”
I gingerly followed Madam Christina through the door to Ms. Panington’s adjoining office. “Ms. Panington, Tom was able to give Dolly an orgasm on his first try…took a bit of coaching, but he did it.” Madam Christina said proudly.
“Well, isn’t that something. That is the first time you have made a pussy cum by fucking, isn’t it Tom?” Ms. Panington picked up the phone, “Ms. Sweeney, would you get ahold of Ms. Jenson and Nurse Pyre and ask them to come into my office. When they arrive I want you to come in with them. Thanks.”
“Let’s take the fake dick off of him, Madam Christina. I don’t want him to get too attached to it,” she laughed.
I stood at attention in front of both women as Madam Christine instructed me on removal of the device. Then she quickly put the arousal meter back on my now flaccid penis. Kelli’s panties remained over my head.
“Would you like Kelli’s panties on or off, sissy?” Ms. Panington asked.
Without hesitation I told her that I wanted them left on my head. I knew that I looked foolish, dressed in women’s lingerie, large breast forms pushing out my bra cups, and with a pair of nylon and lace panties taped with the gusset over my nose. But, I did not want to give up the scent of Kelli.
Soon the other three women arrived. “Tom, as a reward you may masturbate for us. You won’t be cumming, so I will stop you when you seem to be on the edge. Let’s see how long you can make it last.”
So, I began to stroke my small penis in front of these five powerful women. I endured their taunts about my inadequacy and Madam Christina gave an occasional sweep of her whip over my pantied ass.
“Next we will be training on the cunninglus machine, Tom. You do love to eat pussy, don’t you sissy?”
“Ooooh, yes, Madam Christina, I love to eat pussy. Aaargh. I’m going to …”
The alarm sounded on the arousal meter. Nurse Pyre rushed forward with a glass of ice water and doused my crotch. Madam Christina roughly grabbed my hand away. They all watched as my twitching penis began to shrivel under their supervision.
“Okay, Tom. Enough. Back to your training. We will be tucking your wee-wee tightly between your legs and secure it with a tight panty girdle to keep you out of trouble while you first practice pussy worship, and then hopefully graduate to ass worship. Let’s go.” And with that Madam Christina grabbed my now flaccid penis and led me back to the training room.