Fuckbuddy Demoted to Sissy-Maid Pt. 06

Note from the author: I know it's been a while. I have a good idea of what depraved direction I want to take our Sissy towards, and I'm not giving up on the story. It's just been harder lately to find myself in the correct mood to want to write smutt, and have the motivation to do so. I would promiss that the next installments will come out faster, but I know that's not a promiss I can guarantee I will keep. So instead I will just promiss that the next installments will come.

CH13: Embracing the femme within

As you would expect, and as Marion banked on, the less she let me out of my cage, the more devoted I was to her. I set up a special ring tone for her, and made sure her messages and phone calls always went through, even if my phone was on Do Not Disturb. The thought of being unavailable when she beckoned me no longer ever crossed my mind. Any summon might be the one that earned me my release, but more importantly, I knew failing to show up would definitely delay it as a punishment. Marion took full advantage of this, treating me as a magic domestic fairy that could be summoned through a strict text.

"Pick up my amazon delivery from the locker. It's a dress I want to wear at a party tomorrow, so run it in a cold cycle as well, and make sure it's hanging nicely so it doesn't get wrinkled."

"The girls are coming over for a drink after work. They'll be there at 7:30PM, make sure you spot-clean the apartment before that. We'll probably move to someplace with music around 10 or 11, I'll let you know so you can take care of the mess while we're out. I'll definitely need a foot rub, and maybe a face to ride on afterwards, so wait for me there. If you're bored work on your posture and your Sissy voice. Oh, and pick up some Prosecco and some snacks on the way there, I'm all out."

I loved how harsh she was, how entitled she acted. I felt completely owned, and that thought never failed to make my Clitty strain in its cage. She loved pushing the limits like this, never getting tired of seeing how desperate I was. Would I complain that she was monopolizing my entire evening, or about how inconvenient it was to clock out of work early just to go pick up her mess, or about how degrading it was to be told to make myself scarce while she had some fun, and then come back to clean up after her and her friends while they continued partying? Of course not, I was her caged servant, I knew my place. Would I complain that she expected me to kiss, lick and rub her sweaty feet after a night out dancing in high heels? Of course not, I loved and worshipped every single part of her body now. Would I complain when she rode my face to orgasm while telling me how many guys danced with her, how many had felt bold enough to let their hands roam, and how horny it made her? Of course not, she had come home to her obedient maid for release after all, and, honestly, I just enjoyed the rarer and rarer sexual contact with my Mistress. Would I ask to be paid back for the Prosecco? Of course not. I wasn't into findom, but there's a line between buying a few small things like that, and forking out 50% of more of your paycheck. And the line was that I wasn't willing to risk an orgasm for beer money.

My releases were less and less frequent, and Marion was also making eating her out a rarer and rarer privilege (expertly flipping the script by the way, turning it from something I did for her, to a reward for me). At the same time, she was having me over to spot-clean or run a random errand so often that her apartment was now constantly clean, which cut on my chore-time. This gave us plenty of free time when we met each other, which Marion decided to use to squash every last bit of masculine presence from my Sissy body. Ever since she locked me in chastity, I was already conditioned to no longer consider myself a man while in her service (Can you call yourself a man when you no longer control your own manhood?). I responded to feminine pronouns (or Slut, Slave, Maid, Sissy, Bitch...), I tried to act as a stereotypical submissive woman. But Marion wanted to take it further.

She made official the rule that I was to wear panties all the time, even when not serving her. She was quite happy to learn that I had basically already self-imposed that rule. She then methodically approached every aspect of my Sissy persona that she felt wasn't up to her standards.

She started with my make-up. She bought me all the necessary supplies (and had me pay her back of course), then took the time to explain to me how she wanted it done (a bit slutty, but not comically so), then having me practice over and over. Once I got decent at it, she ordered me to practice it twice a day until I got it perfect. I would put a face on once in the morning before work (which I would of course remove immediately), and then once when beginning my service to her (at this point she was having me run some errands every day). Sooner that I thought, I found myself skillfully blending my foundation with my skin, combining lip-liner, lipstick and lip-gloss into an alluring smile. I was giving myself smokey eyes and my naturally long lashes (turns out a lot of guys have pretty long lashes that would make most girls envious) were highlighted with a touch of mascara. The eyeliner was the trickiest to get right, but, once I figured it out, it became one of my favorite details. A touch of bronzer, highlighter and blush to make my cheekbones more womanly and I was done. I had a sultry look that, combined with my subservient attitude, would've made plenty of straight guys go crazy. I tried to ignore how gay that sounded, focusing on Marion's instructions. She wanted me to look sexy, a bit slutty. She wanted me to pass as a woman, and as a good looking one at that. "I would fuck me" wasn't something to be ashamed of anymore, it was my objective. And I had to say, Mission fucking Accomplished.

Those superficial changes were pretty easy to incorporate, as well as pretty fun to master. Looking at myself in the mirror in a face full of make up never failed to remind me that I wasn't a man anymore. Seeing my make up ruined after a long make out session with my Mistress' feet made it clear that I wasn't a woman either. I was a Sissy, an inferior being, and I should count myself lucky to be allowed to serve someone as beautiful as Marion. But to properly pass as a woman, Marion wanted my Sissy personality to go deeper. So she made me pick a name, which felt like a surprisingly serious commitment. Everything I did so far was still just a sex game, although it had admittedly gotten out of control. Somehow, picking a Sissy name felt like I was making this side of me real real. But like every other step I took towards the abyss, the thrill of my own demise had my Clitty throb. So I settled on Lucy. It felt nice and simple, adequate for a submissive maid. Marion smiled when I chose my name, and lost no time making sure Lucy grew into a real person:

"I'm excited to play with you Lucy, but we need to work on your figure. You're going to go on a diet, you need to lose at least 15 pounds, maybe even 20. I want you tracking your calories from now on, so you can work on getting a thinner waist. Also, I want you on a more lady-like workout. I know you've been working on squats, and on the Stair Master at the gym, keep doing those but also start following some female fitness youtubers and doing their routines. Pick your favorite and let me know so I can approve it. And get started on YogaWithAdrienne's basic courses, guys like a flexible girl!"

Being called Lucy out loud, and asked to make all those lifestyle changes had me blushing like a tomato, but I nodded in agreement. I wasn't fat by any means, but I could lose some weight, especially if wanted to look dainty. I loved how invested Marion seemed to be into making me the perfect Sissy maid, at her beck and call, submissive, demure and feminine. It made sense of course, she was living a chore-free life, which no-one in her tax bracket could ever dream off. Still, the attention was nice, and she was 'forcing' me to live my darkest fantasies. Finding time for those workouts would be tough, but I had my orders, so I would figure it out.

Finally, a much more subtle set of changes that Marion started to tackle, were my mannerisms. Marion made me work on a feminine voice, punishing me whenever I spoke in too low a tone, whether it be because I forgot during conversation, or because I was begging for release, or moaning from pleasure, or crying from pain. She wanted my Sissy voice to be a reflex, to be second nature, so that even as she spanked my ass silly, I wouldn't break character. No matter how I dressed, or how feminine I consciously behaved, a thousand mannerisms gave me away unconsciously, which Marion pointed out, then squished one by one. She fixed the way I leaned (that one was easy, "Maids shouldn't lean on things, you should stand at attention, or kneel waiting for orders."). She fixed the way I walked (in heels, in flats, and barefoot), particularly how I carried my shoulders. She fixed the way I sat (no more manspreading), I should sit with my both knees touching, for modesty, unless I was told otherwise for 'access'. Hands on my knees, and either both feet together on one side, or spread on each side. I questioned the 'modesty' argument, as with my slutty maid dresses it often meant that I was sitting with my bare butt on the chair or couch as they were too short to fold under me, especially with a petticoat, and I was at risk of flashing anyone who bothered to look. But Marion loved it though, so the rule stayed:

"I love it, it looks like you're a shy innocent girl who doesn't realize anyone can see her panties. It's not like you're going to wear those dresses in public, so keep up the act. Being eye-candy is part of your job anyways."

I blushed, and ignored her mention of going public, and focused on playing the part. She fixed the way I knelt and the way I stood on all fours. She even fixed the way I sat to pee, making sure I was in character at all times. Deleting old mannerisms was often harder than implementing new ones, so she had me focus on those. She taught me how to curtsy when I left the room or when she gave me an order. She taught me how to kneel beside her when she relaxed on the couch. She taught me to keep my eyes down when in the presence of my betters (understand, everyone else). She taught me how to be a submissive woman, and importantly how to not act like a man, as I had long given up that privilege.

I loved becoming Lucy, and each rule I had to follow made it easier to immerse myself in my submissive alter ego. As much as I tried to keep both identities separated, Marion's changes leaked a little into my real life. For starters, I was terrified of inadvertently using my feminine voice at work. But more importantly, the enforced submissiveness and obedience I was subjected to every day (as well as wearing lacy panties and a pink cage under my work attire) affected my confidence in the office. I used to be a voice of authority in my team, working almost as a tech lead in an unofficial capacity, and primed to replace my manager in a somewhat near future, as he was himself being groomed to replace his own soon-to-retire manager. Now though, I found myself less able to lead, and that left a void that my colleague Anthony was quick to fill. To be fair to Anthony, he was quite competent. We were probably equally skilled technically, he just happened to be a bit rough, and people skills matter. I also just happened to be there first, so he was always in my shadow. Until now. When I failed to step up to the plate and split the work among the team at our last meeting he took charge, and the team silently agreed. More and more I was finding myself working on tickets that required a lot of technical work, but lacked visibility, while Anthony made himself look irreplaceable to management by taking the higher visibility tickets, and acting as the de-facto team leader.

This loss of standing was one of the first times I actually considered rebelling against my Sissy side, against Marion. But the thought of NOT being at Marion's beck and call, and going back to my vanilla life was much scarier than maybe missing out on a promotion. I was enjoying being a Sissy too much to give it up. And quite frankly, I wasn't sure if I deserved to lead the team when my nature seemed to be more apt at following orders. So I pushed thoughts of that promotion aside. For all I knew it would be another year or two until our N+2 retired and the promotion became a reality, anything could happen by then. As much as I hated to admit it, a small part of me was actually glad of this unofficial demotion. I wasn't sure if I would be able to lead the team like I used to anymore. And being out of the spotlight made it easier for me to focus on serving my Mistress adequately. So maybe in the end it was all for the better, even if it meant dealing with Anthony's attitude. I thought we had always been cordial, but I guess he had built-up some resentment at seeing me always be management's first pick, despite him being just as capable. He had hidden it well as it wouldn't have helped his case, and since I was always winning I had no reason to assume there was any animosity between us. But now that he was in the top spot, he was making damn sure I stayed in my place. To everyone else he was just as professional as ever, but from his snide comments and his micro-managing of my work, it was clear that he held a grudge. and finally had the opportunity to settle the score.

I focused on my 'femininization exercises', as my Mistress liked to call them, and on being the best maid she could ask for, hoping to earn an ever-elusive release, and in the back of my mind I held on to the hope of fucking Marion again. Maybe if I kissed her feet well enough after she came back from her weekly run she would see how devoted I am, you know?

I guess I did a good enough job, because one day Marion came back with a box and a large shopping bag. She handed the box to me, and I opened it to find myself staring at a pair of silicone tits. I wasn't sure what they were, until Marion explained:

"These are Silicone breast shapes you can glue on your chest. These should give you about a C-cup. You use this body-safe glue to hold them in place, and, like every other woman, a bra. You can't wear something with too much cleavage or it will give the game away, but with the proper tops these should give your figure what it's missing up top. As long as you keep up with your diet and exercise routine, you should look delicious soon."

Following her implicit command, I started stripping so she could try putting the breast forms on me. I kept my chest hairless, per Marion's orders, so she had me lie down on the floor while she lathered the forms, and my chest, with the glue. She carefully placed each form, and told me to hold them and not move while she went to shower, to let the glue bond. for good measure she blindfolded me with her stockings, making sure the ball of the foot somehow covered my nose, and gagged me with her panties. I stayed still, lying on her living room floor for 15-20 minutes. When she came back, she excitedly ordered me to stand up and brought me to a mirror.

I looked hot. Seeing boobs stretching out my bralette was incredible, and the silhouette they gave me was undeniably feminine. Marion fondled me from behind, and I melted in her arms like she had done in mine so many times, ages ago, when I still called myself a man. Although I couldn't feel anything, seeing her grope my BOOBS had me instantly straining in my cage. Marion smirked at my discomfort, gave my ass a squeeze for good measure, and pulled out a measuring tape. She started measuring my chest size, just below the boobs, and at nipple level.

"You'll need to upgrade your bralette to an actual bra to support these puppies. No online shopping, I want you to go to an actual lingerie store. Buy a few pairs. Spend some money, don't get cheap crap. And go for slutty. You don't have to volunteer the info, but no lying. If they ask, you tell them it's for you, that you like to cross-dress."

As daunting as that sounded, I didn't bother arguing. For starters that would most likely just get me into trouble without changing Marion's mind, but I figured I would just look like any guy buying lingerie for their partner, so a clerk was unlikely to ask questions. And even if they did, they'd probably seen it all anyways, who cares if a random store employee knew I was a sissy. Most importantly though, this all felt inconsequential compared to the fact that I had BOOBS now. BOOBS.

Marion had me practice walking around with my new found boobs for a little bit, but she seemed even more excited for my new upgrade than I was, so it wasn't long until she dragged to the bedroom and shoved my face between her legs. For a while it almost felt like the good all times, with us passionately hooking up. Of course, back then it wouldn't have been long before I interrupted this cunnilingus to bang Marion, or at least turned it into a 69, for a more pleasurable experience for myself. Now though, I knew my place. I dutifully pleasured my Mistress as I felt my chastity cage tighten, preventing me from getting hard. She was filled with lust, burying my face deep in her folds, barely giving me any breaks to breath, but I kept going. Eventually, my efforts were rewarded with a flow of juices, which I happily swallowed.

After a quick afterglow, during which I gently lapped at Marion's pussy, careful to avoid her clit which I knew would be too sensitive, she sat back up, and said the magic words.

"Your turn now Sissy, lie on your back."

I promptly obeyed, and she went to her dresser. I knew better than to ask questions that might put my long awaited release at risk, so I patiently waited.

"Now Lucy, with those beautiful boobs of yours, it's as close as you'll ever be to a beautiful girl! Sure, you'll always be inferior and bound to serve, nothing we can do about that, but there is one step left to make you into a Woman. Can you guess?"

And with that she turned around, holding two small dildo-looking objects, and a harness. I just wanted to be allowed to cum, but this didn't bode well. Slightly confused, I watched her insert both dildos into the harness, facing opposite directions. Then it all made sense when she stepped into the harness, turning on the vibrations on the smaller dildo, which sat quite a bit lower than the first one. She inserted it into her own pussy with a satisfied moan, tightened the harness around her hips, and looked at me hungrily.

"You have boobs, and now I have a dick! You're way too much of a Slut to be a virgin. I'm going to fuck you Lucy."

Even though the dildo between her legs was quite small, about the same length as the largest butt plug, but the width of the smallest one, a wave of panic washed over me. Was I really ready to give up my ass like this? Using butt plugs was fairly innocuous, but letting her peg me was... I might be wearing a dress, doing all her chores for her, serving her every whim, and pleasuring her on command while being locked in chastity, I had fucked her, and she hadn't. This was one of the last remaining shreds of my dignity. I wasn't sure I could give it away. She probably sensed my hesitation, and simply took off the necklace which held the key to my cage, and dangled it as she slowly approached me.

Her dick swung menacingly as she walked, but my eyes were fixed on the necklace, and the release it promised. She came to the edge of the bed and ordered me to sit up.

"Come on Slut, suck my dick. Make it nice and hard, nice and wet before I take your virginity."

This was easy, I had had plenty of practice with her much larger dildos, so I found myself falling into an almost comfortable pace. Still, the power dynamic was much more apparent now, as I sucked my Mistress dick. The way she was standing up while I sat on the edge of the bed. The way it wasn't just me sucking a dildo, she was also bucking her hips. I could see why she didn't give blowjobs. She was in such a power position as I sucked her off, no way would she enjoy switching roles. Eventually she just grabbed my head, and started gently fucking my mouth. I dropped my hands to my side, letting her take control, as it should be, and listened to what she was saying:

"Just like I expect you to worship my entire body, I own your entire body Sissy. If you want to be released Lucy, if you want me to make you cum, then you're not just going to let me fuck you like the little Slut you are, you're going to beg me to take your virginity."

She kept fucking my face for a while, playing the role of a selfish man very convincingly, and I let her. I was her to use as she pleased, we both knew that much. I thought about what she had said. I knew if she fucked me once, it would become a regular thing. The thought of getting railed by my Mistress was so incredibly demeaning and emasculating, I tried so hard to convince myself to say no, to stand up for myself. But it had been so long since I had been allowed out of the cage, and my dick was begging for release. Even right now, as Marion fucked my mouth with her dildo, my dick was trying its hardest to break free. I made up my mind, and when she let go off my head, I looked into her eyes, and didn't hesitate:

"Please Mistress, take me. Fuck my slutty ass. Take my virginity. I'm begging you."

She forced her dick into my mouth again, aggressively pumping in and out of my obedient lips.

"More Slut."

"I can't be both a Slut and a Virgin, I'm a fraud. I need you to make things right. Please Mistress, fuck your Sissy. My ass is your Mistress. I need your dick up my Sissy-pussy Mistress. I'm begging you, please fuck me. Fuck your maid. Claim your slave"

She gave me a few surprisingly erotic slaps with her plastic cock, then unlocked my cage. She lubed up her dick, as she ordered me to lie down on my back:

"I want to look into your eyes when I claim you Sissy."

She gently removed my plug, added a generous amount of lube to my pussy, and started slowly stroking my half erect Clitty. As I got harder, she positioned her dick against my hole and, without a word, started pushing gently. Already stretched by the plug, I offered very little resistance to her small dildo, and soon enough she was 'balls deep' into me. Still, I couldn't help but let out a little grunt as she entered me for the first time. Even though the dildo Marion was using to fuck me was smaller than the large butt plug, I felt extremely vulnerable. I guess, once a butt plug is inserted it just... stays there. Whereas here, I knew she was about to pump in and out of me. I looked into her eyes, silently pleading for her to be gentle. She saw my plea, and responded by spitting straight into my half agape mouth.

Legs in the air, I let Marion fuck me, increasing her power over me with every thrust. I don't think she hit my G-spot, but the anal stimulation was definitely amplifying the pleasure of the slow handjob she was giving me as she fucked me. In the middle of this depravity, I remember noticing that it was somewhat tiring to keep my legs in the air, especially with my heels weighing them down, which prompted Marion to put them over her shoulders. Having spent almost a full week since my last release, where she had 'generously' allowed me to jerk off, it is no surprise that I soon found myself begging for the right to cum. With a devious smile, she increased the pace of both her thrusting and her stroking, and I exploded in a loud moan.

"Look at you Slut, cumming on your Mistress' dick. Be a good girl and cum for me. Cum as I fuck your ass. Goooood girl."

I shot ropes of cum all over my stomach, and Marion spat on my face one last time, for good measure. She stayed deep inside me for the afterglow of my orgasm before gently pulling out. We were both spent, so she lied down on the bed next to me. As she spooned me, I could feel the dildo in the crack of my ass, which only added to my humiliation. Before post-nut clarity could fully settle, Marion had locked my clitty back in its cage, and taken off the strap-on, not without first plugging my Sissy ass back. She ordered me to put the toys away, making sure I cleaned the stapon thouroughly, and forbade me from cleaning up the mess I had made on my own stomach.

"Go home with the traces of your own depravity on you Slut. You gave yourself belly shots Sissy, now you're gonna walk the Walk of Shame like every other common slut."

And the walk home was shameful. I could swear that everyone could tell I'd just gotten used like a cheap hole. It felt like everyone could smell the dried cum on my stomach. I was at least thankful that it wasn't running down my legs like I'd heard it did for Women, or if it had been a real dick in my... I pushed that thought away. I was straight. Which meant Lucy was lesbian I guess. No matter the depraved shit Marion got me to agree to, that wasn't going to change. Yes, my mistress had just fucked my pussy with a rather realistic looking (albeit small) dick, but it was just plastic, and it was a hot woman yielding the strapon.

As I made my way home, a little voice in my head reminded me that, knowing how Marion usually operated, this wouldn't be the last time she fucked my Sissy-hole. In fact, I was pretty sure it wouldn't be long before I was getting fucked more often than I was allowed to cum. Let alone being allowed to fuck. With that thought, however, came a glimmer of hope, as suddenly my brain connected the dots. When putting the strapon away in her bedroom (for later use no doubt), I saw a new box of condoms in her drawer. At that time my mind was still thinking of the fucking I had just gotten so I hadn't paid attention to it, and to be honest spotting a box of condoms at your booty-call's place isn't exactly eye-catching. But it had been a while now since she had bothered refilling on condoms. Marion must have been wanting to fuck again. It made perfect sense to be honest. As hot as it was for her to deny me sex, she was also denying herself in the process. Sure, dildos and my tongue were acceptable substitutes for a while, but she loved fucking enough that she must be craving the real thing by now. By now I was well trained enough that I would let her fuck my pussy as often as she wanted for the right to fuck hers back. I went to bed with my spirits high, knowing that she probably needed it as badly as I did.