Playing Maid

by Jackie Rabbit

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© Copyright 2020 - Jackie Rabbit - Used by permission

Storycodes: F/f; MF/m; maid; bond; tease; crop; oral; cuckold; cd; costume; chastity; cons; reluct; X

Continues from

Part 3: Second Thoughts

"…That would be fine, just as long as you're one of them, and of course that you both are properly presented in the matching uniforms of my choosing beforehand. Both my guests and I expect to see some leg, and I must say you have some nice ones too. I'll send you some pictures of what I have in mind, I'm sure you can find something on line someplace."

"Yes ma'am. Are you going to release me now?"

"No, not hardly! …You're not cramping up yet, are you?" Sheila then asked sweetly.

"No ma'am… Had we finished our game yet then? I don't think I recall where we left off." This treatment at Sheila's hand had me flustered, it was all so new to me, and as a result I found myself bouncing from one subject to another as if looking for something that would verbally satisfy me.

"You were foolishly teasing me with that rather talented mouth of yours, and I was just getting ready to really lay into you, 'beat you raw' I think I said… So, to continue our little truth game, tell me a little more about your husband; truthfully, how does he feel about all this? He didn't just decide to offer you up one day out of the blue, did he? I find it so hard to believe that the idea just popped into his innocent little head, all by itself, knowing what 'my' Jimmy does to perfectly good women, especially knowing of his interest in you beforehand… For that matter, I kind of assumed he was an alpha himself, but then again, I wasn't exactly shopping for a replacement man at that point either, was I? Here's a little news flash by the way, Jimmy is not the kind of man who's inclined to share either, in case you haven't realized this yet."

"You don't believe me, do you?" I asked. I could hear it in her voice, along with her barbed reference to my less than masculine husband. But to be fair, if I were in her place, I wouldn't believe it either.

"Let's just say that I'm a student of human nature, and I think there's some puzzle pieces missing here…"

"And you, after all this, then volunteering to be my maid, knowing what I would be feeling, or at least you should be knowing how I might feel about all this? And your 'gracious' little invite, back into my own bedroom one last time, where my perfect little life all started to unravel? Was this to rub my face in it, as I initially suspected when I accepted, or did you truly not know the details of what had happened between Jimmy and I?"

"No. I didn't know any of this, and I would never do something like that even if I did!" I told her with total sincerity. What did she think, that I was suddenly some kind of monster? We had been neighbors and casual friends, how could I do what she suggested, to her, or even anybody else for that matter? This at the same time implied that she thought that I thought myself superior to her, where the truth of the matter was quite different, an obvious disconnect between us in regards to this. If this were the case, dominant Sheila would have the natural desire to put me in my proverbial place, teach me a lesson of sorts…

"…So you say! And I'll admit that your words seemed so sincere to me earlier. But, and this is a big but, if you didn't, then why offer to be my maid at all? It just doesn't make any sense" Sheila added, the edge in her voice reminding me that I was still at her mercy here, even though I had brought her off as she wished, rubbing MY nose in it. She had even kissed me sweetly, surely that part wasn't faked. But, she was rambling now, and not all that in-control of herself in her rather curious post orgasmic low, this a stark contrast to the "in-charge" and confident woman who had so easily captured and stripped me not one half hour earlier.

For myself, after the passion had run its course, I became relaxed and contemplative, but sometimes thinking too much as I wound myself down. Sheila had taken this to a whole new level though, she was thinking way, way too much, and there was no wind down at all. She was agitated and still stressed, but I thought I knew how to help with that…

…I felt for her, surely this wasn't her fault, nor fair to her either, and I knew I must do something for her very sanity, as well as my own conscience and perhaps even self preservation. It wasn't my fault either, strictly speaking, but I also knew, that of the two of us, one was about to pay a price, and the other about to collect that payment. I owed this to her at the very least, for the magnificent, although unintentional gift of her former husband, the hands down best lover I had ever bed, not to mention him rapidly growing into my soul mate…

"I think I liked the 'confident bitch' version of Sheila better," I confided.

"‘Confident bitch’? I think I like that" Sheila replied, the sanity returning to her voice once again.

"I've been through a lot though, so I think I've earned some latitude, most especially from you, my little man-stealing maid… Soooo, who's this 'other' maid?" Sheila asked with a smile. I wondered when this moment would occur, but at least the humor for this entire situation had once again returned to her. To look at this logically, Sheila ought to be feeling pretty good about herself; not for losing her husband, but for the easy way she had bested and dominated me. It was hardly any effort at all, on her part at least, she was a natural at this. And truth be told, it almost felt like she didn't need anybody, certainly not another man, unless it was on her terms.

…There was a power in such freedom, not that I was necessarily envious, but I could see others being so…

"Must I answer?" I asked playfully. Sheila was about to receive her own gift from me, to do as she pleased with.

"Pain, or pleasure?" Sheila queried in an exhausted sounding voice, as if an indifferent overworked waitress at a diner taking an order. She apparently didn't care one way or the other, or so her tone implied.

"I chose last time, I think it only fair that you choose this time… Sheila ma'am." I was quite literally offering myself up on a plate to her.

Her raised eyebrow look spoke volumes… "You're either hopelessly naïve, or exceedingly curious…"

"Let's find out which, together," I offered, thinking in my mind that she had left out "impossibly charitable," or even "horned up and kinky" as third and fourth options. I didn't actually know how kinky I really was, but both Jim's belt, and my latest experiences in this very bed led me to believe that this was something I should get to know better about myself. At the very least, being bound up and forced did something magical for me, whether at Jim's hand, or apparently now Sheila's as well.

Without clearly telling me which option she had selected to extract this information from me she simply asked, "who's the other maid?" while staring deeply into my eyes… To which I didn't answer, the rules to this new game seemingly obvious. When I had enough, all I had to do was to confess and tell her it would be my thinner and feminized husband, assuming of course that she then believed me, or didn't start her day already knowing this…

Sheila then walked around to the other side of the headboard, out of my sight, and at first did nothing. I felt the fear, but more so the anticipation building for me, her just being out of my sight having a profound and unnatural effect on me. She could do anything she might like to me, and I wouldn't even see it coming, the anticipation maddening. The infamous "pound of flesh" quote from Shakespeare then came to mind, but the "drop of blood" condition forbade in that tale hadn't been made in my case.

I both heard and felt something being retrieved from the "toybox" under the bed, then Sheila crawling up on the mattress with me, and then she was blowing on my exposed womanly parts as if gently blowing out birthday cake candles. It was erotic and gave me ticklish goosebumps, and at the same time made me aware of the moist condition I had allowed myself to get into down there. Sheila had to see this for what it was, my widely spread and pinned legs had my womanhood feeling open, exposed, and vulnerable, as if in open invitation to a potentially rough lover. She had to therefore know that my doing for her, did something for me too; we both skipped over the eight hundred pound gorilla in the room, the fact that Sheila and I also shared a lover.

I don't know that I was expecting Sheila to immediately return the favor I had done her - nor for that matter what exactly I was expecting - but what I would later find to be a brand new and unused stiff riding crop, with it's equally stiff and new leather tongue section being stingingly applied to the mound directly above my womanhood, wasn't one of them. I yelped and twitched away, or tried to, but my range of restricted motion didn't allow for much of this. Through it all the bed held me firm, this no toy, but a serious and heavy restraint device, a device that I was trapped both in and on until released by a woman with a crop that had no real reason to show me any mercy at all.

The second blow didn't come quickly, Sheila allowing the terror and expectation to build as she dragged the crop lightly across my helplessly naked flesh, seeing and learning from my twitching reactions to her torment. I then expected her to maybe ask her question again, or even a different one, trying to deduce some pattern here, so as to anticipate what was to come next from her unseen hand. She didn't say a word though, the outside of my right boob feeling the leather tongue's sharp slap next, my body jerking slightly left a heartbeat later in reflex to escape the onslaught. Sheila wasn't doing any real damage to my tender flesh, but she was in charge of the pace of things, and obviously of the severity of them as well.

…I felt a little like an experimental lab rat at a medical college, Sheila therefore going to school, and I merely the helpless subject she was to study and learn from that day. I was learning too though, although unlike the unfortunate rat, I could end this easily enough any time I wanted, and of course I was still breathing too. But, by implication this was something that Sheila had thought at one time that Jim was desirous of doing himself, and that made this a very important lesson for me.

Would I do this for Jim? That was a silly question to ask myself, I would do anything for Jim, including holding my tongue for as long as I possibly could while that other leather one worked over my tender flesh, end to end. I imagined that this was instead Jim doing this to me, perhaps to gain his own confession, or as simple punishment for evading his wishes in regards to contacting Sheila in the first place. Or, perhaps as a last option, to take me to a higher plane of sexual need, to that place where stinging pain morphed into delicious and sensuous foreplay. I loved it when he had been rough with me himself, but then again, he hadn't worked very hard for a repeat of that either.

My nipple, my thigh, my belly just above my belly button, and even the fleshy part of my butt all received similar attention, her pause, drag, and then swat someplace new method keeping me off balance, anticipation wise. She eventually came around to "my" side of the headboard to check on me, perhaps even with some newfound respect in her eyes as I hadn't yet begged for mercy from her, nor even seriously cried out. There was something else in her eyes too, excitement, of the shallow breaths sexual kind…

"Don't drop this," she commanded, placing the crop into my teeth, after telling me to open up, although this made any coherent conversation between us infinitely more difficult, should I suddenly want to confess to her who the other maid actually was. It was silly not to tell her, she would know soon enough anyway, but those were the terms we were playing for, as foolish as they now seem. The information was an obvious pretense, a reason to toy with me and perhaps test my limits, or perhaps even test her own while she collected her perceived debt from me for stealing her husband…

There was no next instrument of torture per se to be applied to my trapped bare flesh, but instead Sheila's fingertips, ran lightly from my flanks, and then my butt, and then toward my ankles, I twitching and twisting in hysterics and dropping the crop before she even got to the back of my knees. She continued on, my helpless flanks getting even more attention, I reduced to a struggling and perspiring incoherent mass in moments. In desperation I tried to tell her what she wanted to know - I maybe even succeeded - but I couldn't catch my breath to do so, clearly I was so hysterically overwhelmed… I had steeled myself instead for something painful, some new "torture," this seeming about as far away from that as possible, although really not.

She eventually let me breathe, but she had easily broken me, and she knew it. Her smiling form then appeared in my limited field of view; she picked up the crop I had dropped, her face showing genuine excitement and interest, sexual interest, I could see the difference now. Before it felt like I had been a little like a useful tool to her, something to be broken and then used to get off with, while obviously sending a message at the same time. But, now I was more of a desired useful tool that shared some complementary interests, one that could also take some rough treatment and not fall apart psychologically. This I think made me interesting to Sheila; it certainly made Sheila much more interesting to me!

"Didn't I tell you not to drop this?"

"Yes ma'am," I responded breathlessly.

"And how should we punish you for such flagrant disregard?"

"I should think in any way you see fit," I answered, in open ended fashion.

I would hardly call what happened next "punishment," but I will say it had me doing again for Sheila, and then again after that, dominating and then beating me - even just lightly with her crop for motivational purposes along the way - having a profound effect on her sex drive. It would have made for a nicer ending that afternoon if she had done for me at some point after I had finally sated her, but she hadn't, telling me such would only spoil my motivation to please her in the future, obviously implying that there would be a future next time. I think that this also could be twisted by me as not actually cheating on Jim, because I both had no choice, and I received nothing in return, sexually speaking at least.

We did establish that my now more feminized husband would be taking on the other maid's role, and that he was the one Jim had likely intended to lend out to her for her party in the first place. I would be there too now, but how exactly we would get our maid into costume and deliver her was still up in the air, at least from my perspective.

…In all reality though I didn't really need a plan of my own for this, I only needed to follow Jim's…


I greeted Jim at the door with a gin and tonic in hand later that same afternoon, my former husband and new house servant working on a fine middle of the week meal as he, or is that she, had all the time in the world for such now that she was unemployed. Both "men" I think knew something was up with me, but the maid had the good sense to keep quiet, less she earned my later wrath when we were alone. Speaking of the maid, she was more withdrawn and broken-feeling to me these days, as if the reality of her new life of mundane servitude were slowly dawning on her. There was no paradigm for this unique situation between us three, but I did notice that the novelty of it had apparently worn off for her.

"I talked to Sheila today, she came by the house to pick up some things," I told Jim casually, leaving out that I had invited her in the first place, instead giving the impression that she had just stopped-by of her own accord.


"Yes, for the closing. She said we can have the bed by the way; I thanked her."

"Didn't I tell you not to talk to her?"

"You suggested it, but I don't think you specifically forbade it," I answered, as if I were suddenly a high priced city lawyer. My implied "story" of her happening-by perhaps was not entirely believed, based on his tone alone. I was then left to wonder still again at how often the two talked, and about what exactly, post marriage. I hadn't actually lied to Jim, although I was being deceptive, but this only seemed fair as he had been less than totally honest with me in return; if Sheila's version of me washing cars in my little green bikini was true. Perhaps it even was, but perhaps it wasn't the "big deal" that Sheila made it out to be, at least from Jim's point of view.

"She just gave you that bed? Do you have any idea how much that thing cost?"

"Not exactly, but it's a very nice king sized bed to be sure, and it's also specifically NOT the bed that I used to share with somebody else," I reminded him softly. "To be perfectly honest, I felt obligated to offer something just as valuable in return. I don't know exactly how the conversation came up, but Sheila's favorite aunt had been mentioned, and that you had agreed to pretend to still be together with Sheila for her elderly aunt's upcoming visit."

"I intended to tell you all of this, my love," Jim defended, the tables instantly turned between us.

"I have no doubt of this, but I will admit it was a surprise none-the-less. So, Sheila then tells me that you had offered her a maid too, to help out with her aunt's visit, and she somehow came to the conclusion that I was to be that maid. How could I possibly say no with the fresh gift of that expensive bed?"

"You know she can be quite manipulative."

"I let her. I even offered her a second maid, although I suspect this is the one she was originally intended to get."

"So you're playing maid too, in exchange for the bed?" Jim summed up, in just a few words, though his tone was one of disappointment.

"Something like that, at a bare minimum, and I suspect not just one time either… Listen sweetheart, I so want to get along with her, it'll make things so much easier for us going forward. You two still have a business interest together, and this is a complicated relationship as it is, and I would far rather have Sheila as an ally, than an adversary, most especially if we want her help with our real maid."

"Are you cross with me?" I then asked.

I first received a kiss on the lips where I tasted the gin and tonic I had just handed him. "I couldn't possibly get angry with you, and you're right obviously, it's just that Sheila can hold a grudge, she's not exactly a forgiving woman, deep down… And to be honest, I didn't want to… that is, I didn't want you to have to submit to her like this, she's liable to take advantage."

"Oh, I kind of expect that part, to be honest" I offered with a smile, the special tingle I felt in regards to my upcoming service to Sheila and her aunt for me alone. I just knew a part of me would get off on being put into this subservient position myself, I just didn't know for how long, nor if I could keep such a secret from Jim.

I let Jim's words roll around in my head over dinner, wondering not only what I may have really gotten myself into, but at what it would take to make Jim truly crossed with me, and therefore deserving of some of what Sheila had just given me herself. I still had that little lime green bikini, and I fantasized about gifting myself to him in it while bound to that kinky bed, perhaps with a strap or even that nasty little riding crop clenched in my teeth. Such would be an impossible offer for any man to walk away from, but who would place me into that bed to be gifted to him, and at what cost?

…I could have the new maid do it obviously, but I would be helpless before "her" like that, perhaps she would even want to take advantage of that herself, one last time, although while trapped in her chastity device it would have to be creatively done at best. Such would also remind her of what she once had herself, but now is exclusively Jim's, due to a history of her lies. I had to balance this against Jim really liking his kink, my discussions with Sheila confirming this in a roundabout way, without my having to painfully ask directly about the specific kinks her former husband liked to practice on her in their happy times. Jim apparently didn't like to be on the receiving end with Sheila as I had myself that very day, but to me he was the real deal alpha male, and to expect such seemed out of character and unreasonable.

Sheila had obviously changed during her time with Jim, or perhaps "grown" would be a better way to say it, just as I had changed myself. I wanted something different now too, and our maid, she would be getting something quite different yet again. She had foolishly opened my eyes to all this, with Jim, and this in turn shone a proverbial spotlight on her treachery. There was no coming back from that, as far as I was concerned, our maid on a true one-way downward trip, and if Sheila wanted to lay a little retribution on her while in Sheila's possession, so much the better. I was even okay with Jim's plan for that second key now, I had my reservations earlier, to be honest - although I didn't voice them - but not any longer.

The existence of that second key rolled around in my head some more, and I wondered if I could somehow bait a trap for our maid, with myself as the bait? "What if I were to put that little bikini on, and have the maid trap me on that bed while wearing it?" I wondered. Would this "opportunity" force her to use her second hidden key to unlock herself from the chastity device, then taking one last "poke" at me, perhaps while I couldn't see? I would know it was her obviously, but desperate "girls" can do desperate things, and I would likely hardly feel it anyway after months with Jim as my lover.

Such might even be disappointing both ways, because while I would likely hardly feel "her" unseen intrusion, she might not even be able to get hard enough to perform, after months locked in chastity. And, if she somehow did get hard enough, it couldn't possibly feel good to be flopping around inside a Jim-stretched me. It could even be a most cruel final insult to whatever remnants of a man might be left inside there, if any.

"How to do this though?" I wondered, but here again fate would intervene on my behalf…


"Ask me no questions, and I'll tell you no lies" Jim tells me softly one day out of the blue, holding a tiny key up for me to see, pinched tightly between his thumb and index finger, but only when we were alone.

"Where did you find it?" I ask reflexively, then instantly rebuked by Jim's stare.

"Does it matter?" he asks reasonably.

I concede the point with my silence, but there is obviously more to the story than this, but he didn't press my version of the Sheila event back then either, although he surely had his doubts. No matter where Jim found it, this is still proof positive that it exists, and that seems to me also proof positive that my feminized husband had once again lied to me. That was the final deal breaker for me, but by this time I also expected further lies from him to be exposed, so this wasn't quite as profound as it might seem.

Much has also happened since we were given the strange bed; we sleep on it now ourselves in the master bedroom, but don’t yet use it in the manner it was designed to be. That needs to change, but I can't exactly tell Jim to strap me down and have his way with me on it - this perhaps confirming that Sheila and I had already done such - although a part of me surely would like to. Once that key had been found we even passed down our former bed to my feminized husband, the mattress smelling of perpetual love making, but my own and Jim's now. The matching sheets as well have been stained time and again with bodily fluids, so much so that they're ruined, but the maid gets these now too as well.

I find the imagery sadistic, but also fitting, that second key allowing me to turn off any remaining residual empathy I may have at one time had for her. We've even set this bed up in an unused small bedroom next to the garage, it really no bigger than a large walk in closet, and in fact had been used as such to house her personal effects removed from public display in my home; we then converting the "guest" bedroom back into its primary role once again, once that second key was in hand. This one is for "wanted" guests, and the maid isn't one of those any longer. Her services are still wanted, if not necessarily "needed," but I can now have separation between the two in my mind. The maid's new sleeping location will also allow us some more privacy, as I suspect that she has heard us making passionate love a great many times through the thin wall separating both rooms, perhaps even getting something vicarious from this, something that almost any "normal'' married man would be aghast to hear.

Our lovemaking is still wonderful, but there is more to a relationship than hooking up, elements of trust and communication come into play, and of course mutual affection. I don't know that I necessarily NEED the greater kink that the bed has to offer, but I am curious about it, and it's obvious effect on me. "Does Jim need this to stay interested though?" I then ask myself logically, the dreaded feeling that this thing we have together is just too good to last seeping into my mind during my own quiet times of reflection. I want to offer myself up to him more fully, but I don't want to chase him away with this offer either.

It's so complicated a feeling that I'm paralyzed into inaction on the subject, and THAT I eventually realize, is an action unto itself. We have bigger issues though, Sheila's aunt, specifically all three of us temporarily moving in with Sheila for a week or so, for the purposes of deceiving Sheila's aunt into thinking Jim and Sheila are still together, but just living in a new home now. That date is fast approaching, and I feel the pressure of it. Jim and Sheila, for the purposes of this visit, will also have not one, but two maids, it left just a little vague as to both of them - really us -being in their collective full time employment, or just being temps brought in for the party in Sheila's aunt's honor. I have no idea what Sheila's new home even looks like, but I know that one "maid" in our own humble home can easily keep it clean, and even have time to play chef as well.

My own maid has been on a Jim-controlled weight loss program since he had taken control of her, with daily weigh-ins on an electronic scale that reports directly to a smartphone, and a fitness tracker app designed to get her thinned down into maid's uniform shape before the big event. I have even purchased the matching uniforms we're to wear, and the accessories, in my feminized husband's case that amounts to two padded A cup bra and panty sets, with matching stockings and sensible shoes too. I don't necessarily need the stockings myself, but other than that we'll look alike in our matching and short uniform dresses. We're therefore on schedule for this charade, except for the fact that our maid is still wearing "guy" clothes that hang rather badly on him with his weight loss, and his body is still somewhat hairy like a man's. The solution to that last item is an easy one though…


"Please read this" Jim tells me, after handing me a three by five file card, "and let me know what you think?"

"Congratulations, if you're reading this, I can only assume you have found our balloons and discovered the grand prize key. Visiting Maids has offered free maid service to the finder of this note, and the key attached within, simply respond to:

cuckoldballoon with the key number and a short note to claim your prize."

"What is 'cuckoldballoon?'" I ask.

"It's an email account that I took specifically for this, the more common names with 'maid' in them were already taken, but I think this one gets the message across better anyway as to what was actually won. I have a bunch of Mylar balloons in the SUV, they even say 'Congratulations' on them already. I just have to put the card into a zip lock bag so it doesn't get wet, and have the maid tie the key to the string by her own hand… and release them in the backyard later tonight."

…When Jim first proposed disposing of the second key in this manner I found it sadistically revolting, the balloons would carry it to who knows where, across town, or even across the country? I imagined for a moment if it instead got caught in the nosey neighbors large trees, wouldn't that be a hoot? I don't know how much forethought Jim actually put into this, but logically the altitude the balloons reached along with the prevailing winds up there would dictate the direction at least. I also knew that Mylar balloons didn't deflate like rubber ones did, so there was at least a good chance that they would be aloft for quite some time, eventually littering some distant mountainside, or perhaps even the ocean if they floated that far.

It was especially cruel that our maid would be doing this to herself though, but if she chose not to she could always use her mysterious safeword with Jim, although I got the feeling that wasn't going to happen pretty much no matter what, if it hadn't happened already. The power of attorney made this just a little more serious and permanent though, with that signed document Jim could pretty much legally do anything he might like with the maid's finances, or even her taxes. In this case, her freedom from debt wasn't free at all, it actually came at a pretty steep personal price, the irony amusing to me. Our maid had pretty much sold herself into a life of feminized slavery for a relatively small amount of money, and some inexplicable kink too, but she might not actually know this just yet.

Anyway, Jim corrected the card to include that the account was in fact a gmail, and later that night after her chores were done he told our maid to strip out of everything except her panties and meet us in the backyard. Jim's tone left little wiggle room on his wishes, but our maid's stoic compliance had me briefly second guessing this sadistic ordeal - my guilt getting the better of me for a few moments - right up until Jim handed that little key to her and told her what she must do with it, her shocked expression almost comical. The key's very existence, for me, was anything but comical though; it infuriated me. But, if not for that one little piece of brass I may well have tried to find a way to walk some of this insanity back just a little, gifting her to a stranger, even for a single day, potentially very dark. The period of any "won" ownership was left just a little vague in Jim's note, intentionally, so that we didn't actually gift her indefinitely to a real monster. In reality, we didn't even have to answer the email, if it even ever came.

Speaking of dark, it was dark and relatively private in the backyard with the lights off, but this was also just a little more public of an exposure for her while wearing only panties than we had pushed her into in the past. That would change obviously, but she didn't necessarily know this yet either. The neighbors could still be watching though, certainly the presence of the large bunch of balloons that Jim was holding might draw their attention, they were in fact designed to. One wonders what they thought about the entire affair, surely they had noticed that Jim had moved in with us, and surely they had also noticed that my true husband had lost a lot of weight in the past few months, and was home all the time now too. Did they think he was sick, and not wanting to ask about the details out of respect, or did they realize that I had traded up, man wise?

I saw the hesitation in her shaking hands as she tied the little key to the thin ribbon secured collectively to the bunch of floating balloons, Jim's handwritten note card in a zip lock bag and tied above it, Jim taunting her with a final question. Or, perhaps he was instead soothing my own conscience one final time on this ordeal, seeing my own brief second thoughts.

"Is there anything you'd like to say, any phrase at all, before I have you let these go?"

The two stared at each other for a long few seconds as I watched, wondering if she even knew what the little hand written card even said. She had no job, no home of her own, nor even access to any money of her own either. She wouldn't even have that little key any longer - once she let those balloons go - so no access to her useless man bits either. Jim and I were both properly dressed for the cool night air, where she was standing barefoot on the dewy grass while wearing only a pair of emasculating panties, covering an emasculating glass chastity device, oh how far she'd fallen in just a few months. We could stand here all night while waiting for an answer, where she was cold, and getting colder, but I don't know if that was the only reason for her trembling hands…

She had slimmed down drastically on Jim's weight loss program, she was never fat as a man, not really, but not masculinity fit either. That and the panties now made her look… feminine, except for her male styled glasses, nearsighted since a teen and needing them ever since. Her more masculine glasses spoiled the look, in my opinion, as did her hair, but it was long enough now to do something creative with it, perhaps a bob of some kind, with bangs, still feminine, but not overly so.

"…No sir."

"Then hold the string yourself, and let them go at the count of three… One… two… three…"

We all three watched the balloons float up into the dark sky, but most certainly each with different thoughts about such to be sure. When they were gone from sight we watched for a few more seconds, the slight night breeze taking them to the Southeast, up through the neighbors backyard. We three then had a "what now" kind of moment, Jim once again taking command though.

"Go in the house and take every bit of your guy clothing, shoes too, and put them into as many black garbage bags as it takes to hold them. Then I want you to put them out at the curb, tonight, as tomorrow is garbage pickup day."

Our maid just stood there dumbfounded, as if Jim had just cracked a joke, or perhaps had told her to spit wooden nickels.

Jim just stared her down, but she didn't yet move, frozen in place like a statue.

"One!" Jim hastily unbuckling his leather belt from his pants.

"Two!" Jim was working the belt from the loops, I was frozen to inaction, not believing what I was watching. The time for any effective resistance from our maid long past, as any logical person could obviously see…


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