Part 28
Bill was thrilled to be with Tracy, and Tracy was thrilled to be with her Bill. But there was a lot unsaid. Still, they were glad to be together.
She had bought a few things for the apartment and was excited about showing him around.
“You are going to love what I got for you in the playroom,” leading him in. There, the room had been outfitted as a mini dungeon, with a stirruped bondage chair, a spanking horse, a metal cage and a couple of other things the purposes of which were not immediately apparent to him. It looked more than mildly ominous.
“All thith ith for me?”
“Yes darling. You’re going to love it!”
He swallows hard, not knowing quite what to say and not wanting to hurt her feelings.
“Wow! That’th awethome!”
“And here’s your bedroom–for when you’re not sleeping with me.”
One of the guest bedrooms had been redone in all pink and white with satin and ruffles everywhere. It smelled unmistakably girlie. She showed him his new clothes—absolutely over the top! Bras, panties, corsets and other shapewear, stockings, and nightwear. His cock was straining in its confines.
“And (showing him the closet), these are your uniforms. I had them custom made just for you. And everything else that you’ll need—pinafores, headpieces, shoes—aren’t they perfect!?”
A dozen dresses in various cuts and colors hung neatly in the closet. He ran his hand over a couple of the dresses, examining them.
“Maid’th dretheth?”
“Of course maid’s dresses. But we can talk about that tomorrow. C’mon, let’s get ready for bed. I’ve already picked out a nightie for you, and I’ll help you take off your makeup. I cannot wait to get my hands on you!”
Bill was all for that!
Soon they were under the sheets making out passionately.
“Trathy, you feel tho good! And I really need thith! I heven”t cum in three weekth. If you want to take off thith chathtity then we can make love. Are you ready?”
She answers almost distractedly, still kissing him all over.
“Oh, I cannot do that.”
“You cannot? Why’th that?”
She keeps kissing him.
“Because Elijah has the keys. He’s keeping them for a while.”
“Who’th Elijah?”
“He’s a domme friend of mine. He’ll be helping me with your training. You’ve met him. He was the one who put the chastity cage on you at the studio.”
Bill shivers involuntarily—horrified . The “Master” has the keys to his chastity!
She continues with the kissing.
“But why doeth he have the keyth?”
“He said something about needing to hold on to them until you’re far enough along in your training, or something like that.”
“Then how are we going to have thex ?”
“Well, you’re not, at least not for a while. According to the conventional wisdom it’s very clear that Mistresses should never allow themselves to be penetrated by their sissies. But I’ll make an exception for you. At least when the time is right.”
“No thex for me?”
“That’s correct. I assumed that you’d have expected that. If not, you’ll get over it.”
“But what about you?”
“Silly! That’s what your tongue ball is for!”
Part 29
Tracy was insatiable. It was early morning before they drifted off to sleep.
What Bill hadn’t noticed about his bedroom was that there was no interior knob on the hallway door. It locked from the outside. Nor had he taken the time to examine the bed. Tracy had purchased it from Metalbound just for him. It had been designed to enable the occupant to be held captive indefinitely and had other bespoke “features” Tracy had personally chosen.
And the Maid’s Quarters at Tracy’s studio? It had once been fitted up by Tracy as a prison cell for some of her more perverted patrons. The conversion to a Maid’s Quarters was simple—really no more than putting a bed pad, sheets, a thin blanket and a pillow over the top of the padded bondage bench, and adding a metal desk, bolted to the wall, that could double as a vanity or makeup table. It was still very much a functional jail cell, with its one small window even having thick metal bars, and the stout metal closet doors having high-security locks. Bill maybe could have been able to connect the dots from the prison-surplus metal sink—toilet combination, but it went unnoticed.
Morning came, and Tracy shooed Bill out of her bed to make coffee. He returned with two steaming cups.
“Bill, honey, Candi-Floss is going to come over in a little to help you with your makeup and get you dressed. So we are going to have to go over some rules. There will be more rules as we progress, but we will start with the basics.”
“You remember how to address your Mistress?
“Mithtreth. Yes Mithtreth .”
“Good girl.”
Bill winces at the “good girl.” She continues—
“Now the same rule applies to talking to Elijah or Candi-Floss. Except he is ‘Master’ or ‘Sir,’ and she is always ‘Miss.’ And you must never speak unless spoken to. Is that clear?”
“Mithtreth yes Mithtreth.”
“You do know to curtsy whenever you are entering or leaving a room, and whenever you address a superior?
“Mithtreth. Yes, Mithtreth,”
“Very good. Now about your duties as a maid … .
Bill interrupts—
“Excuthe me Trathy, but you never said anything about being your maid. I don’t know … ..”
“Didn’t you just tell me that you understood the rules about addressing your superiors?”
“Yeth, I do but … .”
“Quiet! Stop this minute!”
Bill notices a flash of anger in Tracy’s eyes. She picks up a small book, opens it and makes a note.
“If I haven’t made this clear by now I will make it crystal clear again. I am doing this for you, on my terms, it’s what you asked for, and what you agreed to. There will be no back talk. And every act of disobedience, every failure to comply, every breach of etiquette, no matter how minor, will be subject to correction, both by me or Candi-Floss, and by Elijah. And each transgression will be noted in this book, your ‘punishment log,’ for Elijah to deal with appropriately during your trainings with him.And also, to be clear, you are to obey Candi-Floss and Elijah, as well as your other superiors, as you obey me.”
“Now, shall we continue?”
A sense of alarm washes over Bill. This was very much unexpected. He swallows hard.
“Mithtreth. Yeth , Mithtreth.”
“Vey good. Now where were we? Yes. Your duties and responsibilities as a maid.”
“I expect impeccable and appropriate dress at all times. Perfect hair and makeup. Uniform clean and ironed. Perfect nails. No runs in your stockings. Perfume. All these things. Any departure from what is expected will be noted in the punishment log. Candi-Floss, who will also have access to the log, will mentor you on these matters as well as with respect to the cleaning and tidying that will need to be taken care of here and at the studio. Is THAT understood?”
“Mithtreth. Yes Mithtreth.”
“ The only place where the rules will be relaxed, and even there not completely, will be in my bed chambers. Once you leave my rooms, you are a maid. My maid. And you will behave accordingly. Again, is THAT clear?”
“Mithtreth. Yes Mithtreth.”
“Good. For your sake I hope you do. When it comes to behavior correction, Elijah can be quite merciless”
“Now, while we are waiting for Candi-Floss, let’s practice your curtsies.”
Part 30
Candi-Floss eventually arrives and she takes Bill to his bedroom to prepare him for his first day as a maid. She explains that he will need to match his dresses to the time of day—pink or light yellow for mornings, light blue or gray for afternoons and black for evenings. Always with color-matched shoes and stockings, and always with a pinafore and headpiece. And all are to be kept clean and ironed.
Candi-Floss explains that Bill will be instructed by her on how to be a ladies maid—-how to serve Mistress Tracy in her bath and toilet—to bathe her, dress her, and tend to her hair and makeup. He will learn by performing these services for Candi-Floss, and won’t be allowed near Mistress Tracy for these purposes, until he has achieved an adequate proficiency. Poor achievement will be noted in the log. Until he achieves the necessary level of proficiency, she will be coming over several mornings of the week while Tracy is at work so that he can practice on her.
All laundry, Tracy’s, hers and, if he should require it, even Master’s, is to be done by him. Ironed, if necessary, and all delicates, bras, panties, and other items, are to be hand washed. And he will be graded on how well the laundry is done, folded and put away. Deficiencies will be noted in the log.
He will be responsible for the cleanliness of the apartment and the studio, including the wiping up of semen and other bodily fluids and sanitizing equipment after sessions. There is a washer and dryer at the studio, and studio laundry can be done there.
And eventually, he will be responsible for household shopping, but only after he has mastered the basics.
“But Cand-Floth, what will I wear thopping?”
She says nothing, but deliberately picks up the punishment log and makes a note.
Bill realizes he has misstepped.
“Care to say that again? And were you spoken to?”
“Mith. Thorry Mith. I wath not, Mith.”
“Better. Much better. And in answer to your question, many domestics can be found shopping at the market.”
It’s quite a lot to take in. After a while, Bill is starting to wither from the weight of what he has gotten himself into. He feels stressed, and his mind is saturated. Candi—Floss decides to save the rest for later.
“Now let’s get you dressed, I’m sure Mistress Tracy cannot wait to see her maid in uniform!”
Bill showers, and towels and dries his hair Candi-Floss teaches him how to use the blow dryer, a flat iron and hairspray to style it as it had been styled the day before.
She tells him that he should always check, and trim, if necessary, his eyebrows. Every morning. Bushy or unkempt eyebrows will always earn a notation in the log.
She allows him to try doing his own makeup. She is surprised at how well he does. “He’s done this before,” she thinks. With little touch up from her he’s done. She applies setting spray.
Candi-Floss decides to bait her mentee-
“I must say you are a natural sissy! It took me several years in my teens to be able to be able to do my makeup so well. No wonder Mistress Tracy chose you. She must have known how effeminate you were all along.”
He blushes furiously.
“But that’th not true! Take it back!”
She twists the knife—
“Yes it is. It’s completely true. Only you couldn’t see it.”
He hates this.
She picks up the log and makes a note. The slut tricked him. He realizes his misstep, yet holds his tongue. He’s starting to learn.
“I see that you do understand. Several marks in the book already—Master is going to have quite the time with you!”
Bill feels his helplessness.
“Now, today’s underwear—let’s see. But first, this!! (She holds up a yellow-jeweled anal plug.)
Bill groans. She efficiently buries the plug in his ass.
By now Candi-Floss’ panties are quite damp. and she is feeling a needy frustration. She decides, out of a sexually frustrated spite, that today’s underwear will not be pleasurable for Bill. What better way is there to inflict discomfort on a girl than heavy foundation garments? The very thought makes her even wetter.
She remembers seeing an open-bottom Rago all- in-one body shaper among Bill’s new underwear. Perfect. Extra firm control and very difficult to wear over a long day. Sweat inducing foam pads to fill out the bosom, bone stockings, white satin panties and a bone-colored nylon full slip. “He’ll sound deliciously swishy when he walks!”, she thinks. All of this amplifies her arousal and frustration.
Once his underclothes are on, she hands him a light yellow gingham dress , with white ruffled trim, from the rack. Then a matching headpiece, ruffled pinafore and locking bone-colored pumps. A spritz of perfume and he is ready for the great reveal. She attaches a leash to the ring on his collar and leads him out.
Bill quickly decides that he does not like wearing the body shaper. Not one bit. But the realization that he is trapped in it for the rest of the day causes his dick to try to swell even more within its confines. “What’s happening to me?”, he wonders.
“Now remember your curtsies!”
“Mith. Yeth Mith.”
Part 31
Tracy is thrilled and elated to see Bill in full working maid livery for the first time. He curtsies and looks at her expectantly hoping for a compliment, but receives none—only a rebuke—
“Maid—eyes down, at my waist or feet. You are not permitted eye contact with your Master or Mistress unless given permission. Candi-Floss, make a note.”
“Mistress. Yes Mistress.”
Candi-Floss opens the log and notes the transgression.
Tracy’s demeanor is wholly different from in her bedroom. She’s no longer the affectionate girlfriend or lover. Instead, she is the Mistress of the house,, all business and in absolute and strict control. And he is now nothing more than a maid.
“Very nice job, Candi-Floss, especially for the first day.”
“Mistress. Thank you Mistress.”
“Candi-Floss, I have al little work to do this morning. In the meantime, I want you to work with her on her voice and walk. I want her speaking softly and breathily, from the front of the mouth, not the chest. You know what I’ll be looking for in the walk. And I have a guest coming for lunch at 1:00. I want her to serve, and she will be graded. Uniform change will be at 2:00, after lunch. Later than usual for today only, as I have something special for her.”
“You are dismissed.”
Bill gets through the rest of the morning more or less unscathed, except for a couple of cuts of the cane administered by Candi-Floss in a fit of rage over his walking. All corrected now—the perfect walk—elbows tightly in, palms facing down, mincing steps and audibly swishy hips. An equal amount of progress had been made on the talk.
At close to 1:00 the doorbell rang. Bill met Tracy’s guest at the door with a polite greeting and curtsy, and escorted her back—receiving a “so pretty” by way of a compliment.
Linch went reasonably well, thanks in large part to Candi-Floss’s tutoring . Only three demerits were noted in the punishment log.
At 2:00, Candi-Floss asks if they may be excused as the “Maid” needs to change for the afternoon.
“Yes. But before she puts on her afternoon dress, bring her back here, dressed only in her underwear. My friend here needs to examine her.”
This, of course, horrifies Bill, and puzzles Candi-Floss. When they return, Tracy’s friend’s bag is open on the table. The friend speaks—
“Bring her to me, girl.”
Candi-Floss delivers the leashed Bill to the woman.
“Now turn down her top. I want to see her breasts.”
Candi-Floss does as told. Bill dares not move.
The friend proceeds to poke and prod around Bill’s breasts—still tender from the piercings . She dons a pair of surgical gloves, swabs the areas around his nipples with alcohol, and, after filling a syringe from a small vial, administers several injections around his nipples and areolas.
“There. All done. You may get her dressed.”
By the look on his face, Tracy can tell Bill is distressed.
“What is it Maid?”
“Mistreth. Ith that going to give me breatht Mithreth?”
“No Maid. Not Breasts.”
Bill is noticeably relieved
“But something much better, Maid. Your areolas will enlarge, and your nipples will fatten and grow. And soon, a small knot of breast tissue will appear around the nipple—just like a girl starting puberty. That’s all. Breasts? No. At least not for now. I want your chest to be that of an effeminate male, not of a girl. But to those who see it it will have the promise of breasts to come. If I want to play with a pair of girl’s tits I have Pusscakes for that.”
“Now get dressed and finish cleaning up the kitchen and dishes. And there is laundry to do!”
“Mithtreth. Yeth, Mithtreth.”
Part 32
Bill had read enough about the maid thing to know, at this early stage, a lot of what would be expected of him. So, for the first few days he reluctantly went with it, enjoyed some of it even. But he was still learning. As would be expected, there had been many notations in the punishment log. Most by Candi-Floss, who seemed to take great delight in making sure his transgressions wouldn’t go unpunished. He wondered whether she did it out of jealousy, because she wanted to please their Mistress, or for some other reason. Regardless of her motivations, many departures from required behaviors had been noted over a relatively short period of of time.
On his third day as a maid, and just after he had changed into his evening uniform Tracy’s apartment doorbell rang. Bill swished his way to the door, high heels clicking. He opened the door only to find Elijah. Bill froze, paralyzed.
An awkward moment passed. Elijah broke the silence—
“Stupid Maid! Aren’t you supposed to politely greet your Mistress’s guests?”
Bill partially regained his composure and curtsied, his eyes focused down upon, and oddly drawn to, the dominant male’s crotch.
“Thir. Yeth Thir. Right thith way, Thir. I will let Mithtreth Trathy know you are here, Thir.”
Bill curtsies again.
“Now is that anyway to greet your Master? And I am your Master, am I not?”
“Thir. Yeth Thir. You are my Mathter, Thir.
“The act like it! Worship!”
Without even a pause, Bill, having been triggered, drops to his knees and starts kissing and licking Elijah’’s shoes. As the scent of the shoes and feet registers, Bill is triggered again, and his cock immediately swells and painfully pushes against its prison. This unnerves Bill, who cannot even come close to explaining these reactions to himself.
“That’s enough, Maid. ‘Kneel’.”
Bill obediently relaxes to a kneeling position, his eyes again focused on the area between Elijah’s legs. He notices that the bulge is now much larger. He can even see the outlines of an erection. Another trigger. Bill’s cock strains even more.
“Now say it again, and this time mean it! Say ‘You are my Master’.”
“Thir. You are my Mathter, Thir.”
Bill is impossibly aroused by this.
“Good girl. Now fetch your Mistress, Maid. And be quick. And get me a beer while you are at it. Oh, and Maid, today it isn’t ‘Sir’ or ‘Master,’ it is only ‘Master.’ Understood?”
“Mathter. Yeth Mathter.”
Bill escorts “Master” back to the living room, and noisily swishes off to find Mistress Tracy and a beer. Elijah is struck by the change in Bill. He’s even more effeminate than he could have imagined, and after only three days.
Tracy and Elijah end up sitting and talking in the living room. After Bill refills her glass with wine and hands another chilled beer to Elijah, he is dismissed to his room and told to close the door. The door immediately locks. Tracy and Elijah can now speak about him freely.
“Wow, Tracy, I gotta say. You and the slut have made a lot of progress. But has he always been such a swish?”
“Bill? No. Hell no. You would have never known. And hetero to the core.”
“Well, we know how that goes with these sissies. And no longer his choice anyway.”
“No longer his choice? How so?”
“The hypnosis tapes pretty much opened him up to a more ‘enlightened’ view of these things.”
“I see. You could have at least told me. But I guess there’s no .real harm.”
“The files also implanted various post-hypnotic triggers. I’ve written them down for you.” (Handing her a piece of paper.) “ I just tried a couple of them out and they worked perfectly. You may want to incorporate them into your training. You may even be able to associate them with the Gorean training if you take him down that path.”
“Thank you.”
“Would tomorrow work for another of our classes and his first punishment session?”
“I suppose. Though I really don’t want to watch the punishments.”
“I can do that here, while you’re at work. When you get home, you and I can tie him and the slut up and then do our class. Sound good?
“That’ll work. What time?”
“Can I see the log?”
Tracy hands him the book, and he looks through it.
“I think two or three hours should be enough.”
“That long?”
“Yes. There’s a lot written down.”
“Okay. I’ll be home at 6:00. Does 2:00 work for you?”
“Yes. And I’ll send you a few more hypnosis files. You’ll want to keep up with that aspect of his training.”
“More files? I guess. But only if you tell me exactly what they do.”
“I will summarize each. Promise. Now can we play with him a little more? Maybe try out some of those triggers?”
“Why not?”