~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE
These stories are the artistic expression of the authors who wrote them. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this post, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
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.
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 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 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.
I was back in my room after an exhausting day of training. The prostate stimulating butt plug had been removed. I longed for the sensations it had provided me, and I had asked Madam Christina to leave it in. She had only smiled and said, “So easy, so easy; but no I will not leave it in. You will have to earn the pleasure you have learned that your ass can provide.”
Before we had finished for the day, I had been required to again put on the penis extender and service Dolly. Madam Christina had me practice my aim until I no longer fumbled entry. And I had been given a preliminary ass worship lesson. I had performed to the best of my ability, but had not been allowed another orgasm.
Now, back in my room, I was still very aroused and I wanted to masturbate. If it weren’t for the arousal monitor around my cock I would have piled up a mound of panties from the dresser drawer and humped them like a dog. But, fearing repercussions, I knew that restraint was in my best interest.
Madam Christina had supervised my showering, had reinstalled my arousal monitor, and then she had escorted me bare-naked from the shower, back to my room.
Before she left, she had teased me unmercifully and I knew this was why my cock ached to be stroked and I wanted to spurt. “Select some panties, Tom. I don’t want to have to see your little equipment. It does nothing for me,” Madam Christina had commanded as she sat on the edge of the bed seductively crossing her legs.
I had gone to the bureau and selected a modest peach-coloured hipster and slipped them on.
“Now find the matching bra, Tom, and select some sleep forms that you can wear to bed.”
Soon I was dressed in a matching bra and panty set and kneeling in front of Madam Christina. My erect cock was outlined by the tight nylon and Madam Christina made note of this by rubbing the front of my panties up and down with the toe of her boot.
I had trembled with excitement as she told me, “You did a good job today, sissy. I will be providing a report to Kelli. I think she will be pleased. Just think how you now will be able to fuck her with a full eight inches, no more worry about premature ejaculation and no more selfish fucking. Fucking will now be for her pleasure. What do you think, Tom?”
I had stumbled to answer, “I want to please her, Madam Christina, and I-I-I…” I had been too embarrassed to continue.
“What is it, sissy boy? There should be no secrets, especially given what I have witnessed you do,” Madam Christina had responded.
“I-I had an incredible orgasm today. It was far more intense than anything I’ve ever experienced,” I had managed to say.
“Yes, I know that you did, sweetie. I planned it that way. We all did,” and she had smiled and reached out and patted my head. “When we first heard Kelli’s story about you, we knew what you needed in order to get your masturbation under control. I want you to understand one thing, Tom, and you have a choice to make.”
“Yes, Madam Christine, what is it?” I had answered.
“Here’s the thing. You can either continue your nasty masturbation habit. Of course that will cost you your marriage to Kelli. Or you can promise to never again masturbate outside of the supervision and permission of a woman. If you choose the latter, there will be many more orgasms for you, like the one you experienced yesterday. But Kelli will choose when and where, or whether she chooses to delegate that authority to another woman.”
“But I’ve jerked off for so many years, I am afraid that I can’t stop,” I had weakly argued.
“Yes, you can, Tom. Kelli will help you. You will have to decide whether you want pleasure like you experienced earlier today or whether you just want a quick wank into a pair of panties.” She had paused for effect. “You will have to go to Kelli and tell her that you are fighting an urge to jerk off. She will know what to do. We have taught her.”
“I want to make that promise. I do, and I will.”
“Okay, then, I am going to go summon Ms. Panington and have her come up here. And we will get Kelli on FaceTime. While you are waiting, Tom, I suggest that you carefully consider what it is that you will be saying to your wife.”
So that is the situation that you find me in now. I am trying to compose myself. I am trying to resist the urge to masturbate. I am trying to think. What do I want to say to Kelli? What have I learned so far at the Institute? What is it that Kelli wants from me? Can I make a promise to never again sneak a wank?
I was sitting on the bed lost in these thoughts when I heard Madam Christina and Ms. Pannington at the door. I immediately got on my knees and faced the door. My cock, with an occasional soft stroke over my panties, had remained engorged.
As the women walked in and stood before me, I kept my eyes to the floor in deference to their authority and beauty.
“Does he have a hard-on?” Ms. Panington asked, “I can’t really tell,” and she playfully pulled open the front of my panties and made a display of looking inside, then snapped the waistband back. “Oh yes, I had forgotten for a moment how small he was,” and both women laughed.
“I told Ms. Panington what a good job you’ve been doing, Tom, and she agrees that it would be a good time to call Kelli,” Madam Christina said. “Let’s hear what you plan to tell her, Tom.”
“Well, I, uh, I, uh…” I hesitated, then continued, “I want to tell her that I have accepted that I am a sissy, that I want her to use me for her own pleasure, and that I am prepared to do anything and everything she asks.”
“Very good, Tom. I think that she would like that,” Ms. Panington responded, “And about your nasty masturbation habit?”
“I want to tell her about the orgasm I experienced today. I want to ask her if she will allow me to have such, well, girly-ish orgasms, if she will use the prostate massaging butt plug on me. And, um, I, I umm, I want to ask her if she will allow me to continue to wear sissy clothing.”
“So, you’ve decided then, Tom. No more unsupervised masturbation. From now on, Kelli owns your cock, and she owns your sissy ass?” Madam Christina asked.
“Yes. That is what I’ve decided, and that is what I want.”
“Okay. I will get her on FaceTime then. Remain on your knees. I believe she will like that,” Ms. Panington said.
“Hello, Kelli, so nice to see you. I have our trainer, Madam Christina here with me, and Tom as well. Here he is. He is asking to talk to you,” and she turned the phone towards me so that Kelli could see me, in my peach bra, breast forms, and matching panties, kneeling with an obvious erection outlined through the thin nylon on the front of my panties.
“Hi Tom, don’t you look cute.” Kelli said, “Do you have a stiffie, Tom? It’s hard to tell,” and all three women laughed. “Why don’t you show me how excited you are to talk to me?”
I pulled my panties down below my balls and exposed my twitching cock.
“It’s so cute, Tommy. All it is missing is a pretty pink bow. What do you think, ladies?” Kelli was playing this for all it was worth.
Madam Christina stepped in one of the dresser drawers and returned with a pink silk ribbon and tied a large bow around my penis as they giggled with satisfaction.
“Tom has been very compliant, Kelli. He has been practicing fucking with the 8-inch penis extension, and he’s done a wonderful job practicing pussy and ass worship. We think you’ll be quite pleased,” Ms Panington told her as the phone remained focused on my now pink-ribboned dick.
“Oh my. I am so happy to hear that. I so look forward to Tom’s having a more manly size. Maybe I’ll have to retire my Hitachi,” Kelli joked.
“He has something he wants to tell you about the orgasm we allowed him to have today, Kelli,” Ms. Panington continued. “Go ahead, Tom.”
Ms. Panington tipped the phone so that it focused away from my cock and instead on my face. “Kelli, I love you so much,” I started, “And I understand why you sent me here. I have been selfish. I was more interested in getting off sexually than in pleasing you. That wasn’t fair, and I apologize for my inadequacy as a lover.”
“Well, thank you, Tom, so nice of you to say that. Yes, you have been inadequate. I will accept your apology, but things must be different going forward, Tom. Do you understand that?” Kelli was now speaking quite sternly.
“Yes, Ma’am. I do. I want to serve you Kelli. I want to be the best lover you could ever imagine.”
Ms. Panington interrupted, “Tell her about the orgasm you were given today, Tom.”
“Oh, yes. Sorry. I, uh, well, they, um, put a vibrating butt plug in my ass,” I could feel my face turning red.
“Yes, Tom, go on. I know about that. I picked up one of those devices when I was there, complete with a remote control,” Kelli said, encouragingly.
“Well, it was absolutely mind-blowing. The best I’ve ever had. I want to be allowed more of those. It would be such a privilege for you to give me such pleasure, Kelli, and I want to do my best to give you mind-blowing orgasms as well.”
“You seem to think this is some sort of negotiation, Tom; that if you learn to get me off that I will get you off in return. That won’t at all be the deal, Tom. Here’s how it will be: Your job will be to serve me, to worship me, to obey me. If you please me, I will keep you and allow you to wear the frilly feminine things you so crave as the sissy you are.”
“Yes, Ma’am. I just…”
“Don’t interrupt me, sissy boy. I wasn’t finished. About your desire to be allowed orgasms of any kind, the way it will be Tom is that orgasms will be doled out as rewards, Tom. I think that you find that I will be quite fair, but not over-indulgent. What kind of orgasm, how, when, how often, that will all be up to me as you have clearly demonstrated that you have no self-control. Now you may speak, Tom.”
“Thank you, Kelli. That is what I want. I love you so much and I want to make you happy. I have admitted that I am a sissy. I love wearing these feminine things. I admit that I have no control over my penis and that it is best that you take firm control. I will dedicate myself to serving you to make up for the years that you went without,” and tears began streaming down my face.
They were tears of joy. They were tears of relief. Most of all they were tears of submission. My body began to shake with deep sobbing, and I hid my face in my hands.
“Take your hands away from your face, Tom,” Kelli finally began, “Do you promise to submit to my authority?”
“Yes, Kelli, yes I do.”
“Do you promise to never masturbate again, and that I will choose when and if you may have an orgasm?”
“Yes, Kelli, yes I do.”
“And do you agree that, as a symbol of your submission you will only dress in female clothing in my presence?”
“Oh yes, Kelli, yes, yes, yes!”
“Well then from now on I will only address you by your feminine name, and I ask that the staff at the Institute do the same. And your name shall be…Nancy.”
I was at first stunned by this development, but in no position to protest.
“Say it for me, sissy. Tell me your name,” Kelli said, now seductively.
“My name is Nancy. I am Nancy and I wish to serve you and please you. Thank you, Kelli.”
“No Nancy, you may no longer address me as Kelli. The ladies at the Institute have told me that would be far too informal for our new relationship, Nancy. From now on for you it will be Mistress Kelli.”
“Yes Mistress, thank you Mistress.”
“Good night, Nancy.”
“Good night, Mistress Kelli.”
With that Ms. Panington disconnected the call, set the phone down and she and Madam Christina began to applaud. “Very good, Nancy. Very good. Now off to bed with you. Tomorrow will be a big day.”
As the lights were shut off and the door to the bedroom was closed, I had little option but to go to bed. I lay awake for the longest time. My mind flipped through the events of the day and my entire stay at the Institute. I thought of the times that I had disappointed Kelli as her lover; how I had been unable to bring her to an orgasm, or had spurted within seconds of entering her. I thought of how I had taken to masturbating just to get myself off, and how my sexual fantasies had turned more and more to exactly what I was experiencing now; being feminised and dominated by women.
I felt happy and excited, and my mind began to turn to what my new life would be like when I returned home. I wondered if I perhaps would not have to continue to look for a job, whether I could satisfy Mistress Kelli by taking care of her and all of the household responsibilities. I shuddered with excitement as I pictured taking care of the house dressed as a sissy maid or maybe as a 1950’s housewife.
My hand drifted down to my cock and I indulged a few strokes. I wanted to jerk off so much. It was difficult to pull my hand away. For a moment I humped the mattress. But I knew that Ms. Panington would check the printout of my arousal during this alone time. I was making progress and maybe close to being allowed to return home. I didn’t want to take any steps backwards, and I certainly didn’t want to return to the nursery. So I tried to distract myself until sleep enveloped me.
As Nancy was trying to get to sleep, Ms. Panington, Madam Christina, and Ms. Jensen were in Ms. Panington’s office and had Kelli back on the phone on a video conference call. “Perfect, Kelli. Just Perfect,” Ms. Panington was telling her.
“Thank you so much. Do you think he takes me seriously?” Kelli asked.
“Without a doubt, Kelli. He will be like putty in your hands. Not only does he love you very much, and not only is he deathly afraid of losing you; but Kelli, he likes you being firm with him. He likes submitting to women. He likes being allowed to wear feminine things. Rarely do we see men who are so innately submissive. It is a fantasy for some, but for your husband, this seems to be who he is,” Ms. Panington explained.
“And you should have seen his face as he had his first prostate orgasm. And he’s been begging for another one,” Madam Christina added.
“What we find is that wives often have to experiment with how frequently to allow their submissive to have an orgasm,” Ms. Jensen chimed in, “There seems to be a magic number between overindulgence and too infrequent to maintain motivation. We find that it is best to keep him on the edge.”
“And one thing that will make it easier about your little Nancy is that he has such a strong fetish for women’s panties—he seems to desire all feminine things, mind you—but panties are really his thing. We think that he’d do just about anything to be allowed a panty-sniffing session or to be allowed to wear the ‘Mommy panties.’ That was a brilliant idea for us to get all those panties made up that replicate those pairs of his mother’s that he first wore and masturbated in as a boy,” Ms. Panington said.
All four women were silent for a moment, and then Kelli began, “I’m thinking about coming out there to give him a test run. I actually just looked at flights and looks like I could get a reward ticket and be there by tomorrow afternoon. What do you think?”
“It’s your husband, Kelli, and your money. If you test him out and he’s ready to take home, we can easily fill his spot with someone from the waiting list. Remember how long you had to wait?” Ms. Panington answered, “Sure. We’d love to have you. We will prepare the Mistress Suite for you, and we will have Nancy primed, prim, and feminised for you when you get here. We’ll keep it a surprise. We will want you to walk in on him when he is in a most humiliating state. Just send your itinerary and I will have Ms. Jensen pick you up at the airport.”
“Great. See you ladies sometime tomorrow, then.”
“Oh, Kelli, before you go, just one question, are you sure about the makeup and hair? I know that you want him to be a sissified male at home, but consider how humiliating it would be for him for you to surprise him when he is fully made up and dressed as a complete hussy?” Ms. Panington asked.
“Mmmm. Let me sleep on that. I will send you an email in the morning. I’m going to get some outfits together, then get some sleep. Goodnight.”
“Wake up, Nancy. Rise and shine. Time to get up, sissy.”
I hadn’t heard the key turn in the door lock, and I hadn’t heard Ms. Jensen enter my room. I sat bolt upright, then remembered that I was wearing only the peach bra and panty set and I grabbed the sheet to cover myself.
“Don’t be so silly, Nancy. I’ve seen plenty more of you than that,” she laughed. Did you enjoy yesterday, Nancy?” Then without giving me a chance to answer she continued, “I think it is so cute that your Mistress has named you Nancy. It is such an old-school feminine name. It suits you just fine.”
“Thank you, Ms. Jensen,” I ventured, still trying to orient myself after the sudden wakeup, and more than a little embarrassed that I was sporting one of those morning erections which she would surely notice.
“Get going, sleepyhead. Up and off with your bra and panties. Ms. Panington wants you showered, shaved and ready for the day ASAP.”
I got out of bed, and then turned away from Ms. Jensen to pull off my panties, hoping that she wouldn’t notice my erection.
“I see it, Nancy. You don’t have to hide yourself on my account. Your little weenie is so cute. It still has the pink bow on it. I heard about that,” she teased. “I guess you’ll have to take that off as well. It will just get ruined in the shower.”
I followed her down the hallway to the bathroom where she opened the door to the glass surround shower stall. She spun me around so that I was facing her and she quickly removed the arousal monitor from my penis. “Here’s a razor and some shaving cream. Ms. Panington wants it all off, as close a shave as you can get, Nancy. Madam Christina said that you’d gotten a bit stubbly ‘down there,’ and we want it smooth. I’ll be right here if you have any trouble.”
The shaving cream was called Satin Care Pashionista Fruit, and it was a lady’s razor that I had been given. And the body wash and shampoo both had a lovely smell of lavender. By the time I was done, the feminine scents had me feeling quite girly.
I toweled off and Ms. Jensen supervised the monitor being refitted, then she took a spray bottle from the counter and gave me a few spritzes of a flowery mist and she handed me a blue “Secret” ladies deodorant.
“Let’s go get you dressed, Nancy,” and Ms. Jensen led the way back to my room. When we got there, Ms. Panington was there and rummaging through the clothes rack.
“Good morning, Ms. Jensen. Good morning, Nancy. I see that you are showered and shaved,” and she gave my bottom a playful pat. “I thought I’d come down and supervise your dressing myself. By the way, I looked at the arousal printout from last night after we left you for the night. Looked like you had taken a few strokes, then stopped. Very commendable.”
“Thank you, Ms. Panington. Yes, I wanted to masturbate; but I meant what I told Kelli, er, Mistress Kelli. I intend to keep my promises to her,” I replied.
“Very good, Nancy. I have laid out your lingerie for today on the bed. I want you in pink lace. We’re going to be using the triple D forms again. It seemed to me that you so enjoy having large breasts, Nancy.” And I blushed with the knowledge that she was, once again, quite right about me.
What I did not know then, and only found out after Mistress Kelli had taken me home, was that Ms. Panington and her staff had spoken to my Mistress after I had been put to bed, and I knew nothing of the email that had arrived this morning in Ms. Panington’s inbox from my wife.
It had read: “Good morning, Ms. Panington. I will arrive on the 3:20 flight. If one of your team is able to pick me up, that’d be great. Otherwise I will take a cab. Please text my phone so that I know.”
“Oh, and about further feminizing Nancy for his presentation to me, I think I will go with that. I want him to be most humiliated when he first sees that I am there. If it turns out that he finds the full treatment of makeup and wig arousing, well then I believe that I will have another carrot to dangle in front of his sissy prick. Have some other ideas, too—will discuss upon arrival. Thank you. See you this afternoon. K.”
“Today I want you in a corset, Nancy. I have brought one with me that I think will suit you just fine. So hurry on with the bra and panty I set out for you, and then I’ll get you laced up,” Ms. Panington announced.
“Yes, Ma’am. Forms too?” I asked.
“Of course, silly. We both know you love having titties like a real girl.”
As I grabbed the panties and opened the waistband to put them on I realized that they were like no panties I had ever seen. There was a prominent round opening in the rear that, as I slid them on, left my butt cheeks entirely exposed. I imagined that this was to provide access for the magic butt plug and I started to get an erection at the thought.
I did as I was told, then stood in front of Ms. Panington as she wrapped a pink under-bust corset around me. She clasped the heavy hook and eye fasteners, and then turned me around so that she could begin my lacing. Being corseted had been a favorite masturbation fantasy of mine, but I had never experienced what I began to feel as Ms. Panington pulled each row of laces tight. It took my breath away. I began to feel unbelievably sexy and my cock was now engorged and pushing against the pink lace of my panties.
Then Ms. Panington positioned me in front of the full-length mirror. From the neck down I looked like a voluptuous woman. That is, other than the prominent bulge in my panties. My breasts were large and protruding. My waist had been pulled in at least 3 inches, leaving the illusion of full hips. “Now let’s get a dress on you, Nancy,” Ms. Panington instructed.
She went to the clothes rack and returned with a white satin dress. It had a pink lace bodice and pink lace accents at the hem and sleeves. The skirt flared out and was so short that I knew my ass would be exposed.
“Put this on, Nancy. But first attach these white stockings to the garters on your corset. That’s it. I know you’ve attached stockings to garters before, Nancy, don’t try to pretend you haven’t. Good girl. Now these heels.” A pair of modest 2-inch white pumps completed the outfit. “Now I’ll get you some breakfast. Then we’ll be off to the beauty salon.”
“Beauty salon?” I thought to myself as I followed Ms. Panington and Ms. Jensen out of the room and down the hall towards the elevators. I felt very self-conscious about my short skirt as I knew that my bare ass was exposed, and I kept trying to pull down the hem of my dress.
“Stop that, sissy. Hands clasped in front of you. Why so modest about your ass today. Just yesterday you were begging Madam Christina to leave a plug in it,” Ms. Panington said as Ms. Jensen giggled.
Lucky for me, the elevator door opened to an empty car, and we rode in silence to the same floor the nursery had been on, but turned the opposite direction once the elevator door opened. Inside a door simply marked “Beauty,” there were three salon chairs. Two of them were occupied by who I believed to be two of the transvestites that I had seen a couple days earlier being led to a cooking class.
Both were beautiful, impeccably made up, appeared to be getting their hair done, and they greeted me in voices far too husky for their alluring feminine appearances. I mumbled a quick hello, now feeling even more embarrassed to be in the presence of such beautiful feminized men. Ms. Panington introduced me to Ms. Carlson who she announced would be “making me pretty.”
“He hasn’t had anything to eat yet today, so I’m going to order him up a smoothie. Hope you don’t mind his sipping from a straw while you’re working on him?” Ms. Panington asked.
“Oh no, that’s fine. I do the lips last anyway.” Ms. Carlson said, and then turned to me, “Show me your dress, Nancy. It’s gorgeous.”
As I did a slow pirouette, Ms. Carlson let out a low whistle, “Short skirt on this one, Ms. Panington, and those panties, I’m guessing that she’ll be getting the treatment sometime today then?”
“Hush, now. We don’t want to scare her, um, him,” Ms. Panington responded which of course was enough to scare the beejeebees out of me.
Ms. Carlson put a plush terry cloth towel over the remaining empty salon chair and directed me to sit down. Ms. Panington started for the door, and then turned to Ms. Carlson, “I want this one looking quite sluttish. It’s a special day.” Then I heard hushed giggling from the two transvestites. I figured that they knew what ‘the treatment’ was, and they must have thought that it was funny that I was going to receive it.
I sat back in the chair, and soon my smoothie arrived. I was famished, so I sipped on it as Ms. Carlson worked to make up my face. She talked me through it as she went. First she smoothed in some moisturizer, then concealer, then foundation, then setting powder, then eyeliner, brow pencil, mascara, lip liner, then lipstick. She kept me turned away from the mirror until she had topped it off with a shoulder length auburn wig.
Ms. Carlson turned me to look at her creation as she fussed with the wig. I was dumbfounded, speechless, and aroused all at the same time. I felt my cock stirring and growing as I looked at the image of my feminine self in the mirror. What did it mean that I was getting hard looking at my feminine image? Did I want to have sex with myself? I guess that’s what I’d been doing with all that masturbation; but, if I do say so myself, I looked HOT.
Next came some dangly silver ear rings, and a matching necklace. Then Ms. Carlson removed the smock she had used to cover my dress, had me stand up, and again turn in front of her. She gushed over how pretty I was, and let out a stifled giggle when my revealing panties were turned her way.
Soon Madam Christina entered the beauty salon. She first went to Ms. Carlson and whispered something in her ear. I felt embarrassed for her to see me like this, even though she had seen me in many compromising situations over the last few days. She made her way over to where I stood and softly stroked my bare behind with a gloved hand. “Very nice, Nancy, very pretty.”
Without another word she reached into my panties, took my cock firmly in her grip and led me out the door and back to the training room. “Don’t worry, Nancy. We can touch up your makeup. Ms. Carlson gave me a makeup case with the right shades. You don’t have to worry about making a mess while you practice ass and pussy worship today.”
By now it was early afternoon, and I was soon hard at work servicing the plastic pussy and the plastic ass. I had squealed with delight (like a girl) when Madam Christina had inserted the butt plug that pulsed, vibrated, and tickled my prostate in response to my efforts at oral service.
“You’re doing fine, Nancy, but I am going to hold your stimulation just below the level of an orgasm, at least for now. I want to save you for the treatment,” Madam Christina told me.
I succeeded in giving the plastic orifices multiple orgasms. Madam Christina taught me to stimulate the clitoris with my finger while I orally serviced the anus. And, she taught me to digitally stimulate the anus while I worshipped the pussy. I was pleased at my successes, but frankly I was ready to service the real thing. I was confident that I could please Mistress Kelli.
“Okay, Nancy, we’re going to take a break. You can sit back and relax and I’ll get you some water and a snack. Not much nourishment in eating plastic pussy,” Madam Christina teased. “And, I am taking out the butt plug. I know you love it, but that’s enough for now.” I bent over in a most humiliating manner as she slowly removed it.
After a few minutes Madam Christina presented me with the penis extender and told me to put it on, which I did. “Leave the panties on, she told me, “I want the fake cock protruding from your panties.” Then she led me to a section of the room that was curtained off from the rest. Behind the curtain was a padded bench about three feet off of the floor.
On the bench was a black leather head harness with a six inch dildo attached to it. Immediately I knew that this was a chin dildo. I had seen pictures of these, but had no experience with the device. Madam Christina wasted no time in pulling it over my head and securing it. My mouth was left exposed and Madam Christina told me that I was to gently suck and lick the clitoris while my chin cock fucked pussy. The dildo protruded comically from my chin, and she laughed as she stroked it.
“Up you go, sissy, up and on your knees” and Madam Christina patted the bench. I got up and knelt upright. “Bend,” she said, and as I bent at the waist she pulled Velcro straps from under the bench and secured both of my arms to the side of the bench. “Wiggle your head back and forth and thrust your chin dildo back and forth. I want to be sure that you have full movement,” she instructed.
Next she sat herself down in what could best be described as an ornate throne on wheels. She pushed a few buttons and the throne rose up and down and the seat changed positions. She wheeled herself close to my face, lifted her leather skirt, and taunted me with her black panties inches from my nose. “Perfect,” she said and she got up and busied herself behind me. I could look to the side and see my reflection in a mirror that took up the entire wall.
I looked ridiculous. My bare ass was in the air outlined by the cutout pink panties. My skirt fluttered above my ass. My penis extension protruded from my panties and it appeared that I had a huge hard-on. A dildo protruded from my chin. The hair from my wig now hung down partially hiding my face, but my face was unmistakably made up in a most feminine and, yes, sluttish style.
Soon Madam Christina came around in front of me. She had removed her leather skirt. She had replaced it with a dildo harness and she now sported a cock that made my extension seem small. I began to panic as she stood in front of me stroking this phallus just inches from my face.
“You will be getting the treatment this afternoon, Nancy. All of us ladies are in agreement that you’ve earned it. You are such a good sissy, so compliant, and you have shown that you can worship ass and pussy with the best of them. And, we have seen how much you have enjoyed stimulation in your ass.”
She paused. I could feel my body shuddering and my sphincter muscles tightening. “Soon our audience will arrive and I will have the pleasure of fucking your virgin ass. Would you like that, Nancy?” Madam Christina said.
I vigorously shook my head. “No, no, no,” I wanted to shout. But I said nothing. Part of me wanted to experience being taken in this way.
Then I was enclosed in total darkness as Madam Christina pulled a blindfold over my eyes and secured it behind my head. The minutes dragged on as I knew that I would soon enough be violated by that large strap-on and that this would be witnessed by the entire female staff of the Institute. Eventually I could hear the clicking of high heels on the tile floor; then female voices. I could identify Ms. Panington, Ms. Jensen, Ms. Sweeney, Ms. Carlson, and even Nurse Pyre. They chatted amongst themselves like this was an afternoon coffee break.
Suddenly the room became silent. I heard one more pair of high heels click their way towards me. Then I could hear some fussing with the electric throne. I felt a cool gob of what must have been lube on my anus. Soon I felt what I believed to be a finger inserted and there was modest applause from the spectators. Then I felt the head of the dildo at my opening and I heard Madam Christina telling me to relax and to remember how good the butt plug felt. “Soon you will have an orgasm, Nancy, a most sissy orgasm.”
Then I heard the motor on the throne whirring and someone was directing my head. I realized that it was Ms. Panington when I heard her say, “Inhale deeply, sissy Nancy, and service your Mistress.”
“No, it couldn’t be,” I thought, “My Mistress? Mistress Kelli?” I began to thrust the chin dildo and soon my nose was drenched with the unmistakable intoxicating scent of my wife. I thrust wildly and when my mouth felt a wet pussy I sucked in as much fragrant pussy juice as I could. I knew the taste. It was Kelli. My wife. My Mistress. I was in a frenzy, intoxicated with the taste and scent of her, wanting to please her and show her what I had learned.
I felt the thrusting in my ass start slowly, then build. I was in a mood-altered state. Endorphins were firing on all cylinders. Sensations flooded my ass, my prostate was being assaulted, my head was filled with the scent that, for days, I had only been able to sniff from the gusset of panties. And my mouth was filled with the taste of her.
I moaned. I thrust. I wiggled my chin. Then I heard it. I heard Kelli, my Mistress, I heard her cry out with an ecstasy I had never before heard. I heard her gasping, then screaming, “Fuck me, sissy, fuck me with your mouth. Fuck me like you never have before.”
I fucked her with the chin dildo, thrusting violently back and forth, licking and sucking her clit with each forward thrust. The harder I fucked and sucked, the more she moaned and screamed as her hips shuddered with multiple orgasms and her thighs squeezed my head so tightly that it was as though I was part of her.
“Oh Nancy, ooohhhh my sissy hubby! I have waited so long for this. My small-dicked husband finally pleases me,” she shouted.
As Kelli gushed her enthusiastic pleasure, pressure was building in my ass. I could feel myself bucking against Madam Christina’s strap-on. My cock was hard in the confines of the penis extender. I could feel my body tightening and I knew that the first wave of the wonderful prostate orgasm was about to overwhelm me.
“Take his blindfold off. I want him to look at me as he cums with your strap-on in his ass,” Kelli shouted. I felt hands fumbling with the blindfold and soon hands grabbed my chin and held my head up so that I was looking directly at Kelli.
A wave of humiliation flooded me as my wife gazed down at my face contorted in orgasmic ecstasy as I was being fucked in the ass by another woman. “Fuck him. Fuck him,” she shouted.
My body shuddered and I let out an involuntary long moan as I could feel ejaculate leak from my cock. I buried my face back in Kelli’s pussy and she patted my head as the room erupted in applause.
“I am ready to take him home. Thank you all so much. You have forever changed our lives,” I heard my Mistress tell the staff of the Institute. “Please take the chin dildo off of him so I can see his feminized face.”
I held my head up and looked into her eyes for the longest time. She looked back at me warmly. Finally she said, “I’m afraid that he likes looking like a woman a little too much. I think it will be far more humiliating for him to be kept dressed in women’s things, but without the privilege of makeup or a wig.” I knew that she was right. I had found the makeup quite a thrill. Perhaps she would make me up again someday if I pleased her.
“Thank your Mistress for allowing you to service her, Nancy. Remember what you were taught,” Ms. Panington said with just a hint of scolding.
“Thank you, Mistress Kelli, for allowing me to serve you. And thank you for allowing me an orgasm. And thank you for sending me to the Institute,” I said, and I meant it.
“You’re welcome, honey. I can’t wait to get you home.”