Fuckbuddy Demoted to Sissy-Maid

Introduction: Just your 'usual' Friday evening.

I knocked sharply on the door three times at exactly 5:00PM and waited patiently. I had made the mistake of knocking an extra time after a 5 minutes wait once, thinking she might not have heard me, and the resulting spanking had made sure I remembered that her time was more valuable than mine. Eventually she let me in, handing me a ball-gag. I remembered her explaining "As a sissy the only words I want to hear from you are 'Yes Miss' and 'Thank you Miss'. As a man I don't want to hear a noise. Put this on until you're dressed appropriately.".

Relieved that I was now protected behind closed doors, I immediately put in the ball-gag and followed her to the living room, admiring her beautiful legs, accentuated by the high heels she was wearing, and sneaking a glance at the ass I knew I would be worshipping tonight. She sat on the couch while I kneeled in the center of the room, thankful for the thick carpet, and started removing my 'manly' clothes. I was already wearing as much as possible under my street clothes: I was wearing a matching set of bra and panties, pink and frilly as my mistress preferred. Finally, as all sissies should, I was wearing thigh high stockings. The one I had chosen today were white with pink ribbons on top, help up by a white garter belt, completing my slutty look.

Once I was in my underwear, she snapped her fingers, and I presented my dick to her. I was safely locked away in a pink chastity cage, held in place with an additional strap. She quickly inspected the cage before reaching for the ball-gag and ordering: "Greet me properly, Lucy.". Using my sissy name meant I was now allowed (and expected) to answer "Yes Mistress", before falling to my knees and kissing the tip of each of her heels. Her left foot was decorated with a silver ankle bracelet, with a small key dangling from it, making my face flush. It had been 3 weeks since my last release, and she had been suggesting that tonight, if I behaved, I would be allowed to cum.

I completed the greeting by turning around, presenting my ass to her. Despite everything else my Mistress made me do, this was always the part that left me the most embarrassed. Waiting on my knees, head low, ass high, as she dropped some lube on my asshole (my 'pussy' as she likes to call it) and inserted a butt plug with a shinny jewel on the end. We had explored anal play together, but I never found any pleasure from it. Still, my mistress liked keeping me plugged. Thankfully, she used the smallest plug I had bought for most of our sessions, so it slid in effortlessly. The cold and feeling sensation inside my ass was emasculating, even more so than the lingerie I was wearing.

She slapped my ass once, and said "Get dressed, you have a lot to do today.", handing me the outfit she had chosen for the day. My top was a simple black piece with some white lace, designed to look like a French maid outfit. The skirt however was a much more complex piece. It was a tight leatherette 'hoble skirt', with a long slit in the back. I was quite familiar with this piece, as it was one of her favorites. After putting on the top and the skirt, I completed the outfit with a pair of black platform high heels. I stood in front of her for her final inspection, and she kneeled behind me.

The slit of the dress, necessary to walk properly in the tight hobble skirt, was equipped with grommets and laces like a corset, allowing the slit to be closed more or less. When fully closed, the skirt offered almost no wiggle room, making walking almost impossible. I stood obediently as I felt her work the laces, allowing her to slowly restrict my freedom.

When she was satisfied, she explained :

"Tonight after the bar my friends are going clubbing, so I'll be back a bit later than usual, which will give you more time for chores. In the meantime, I expect your help to get ready, I want to look amazing.".

Chapter 1: My downfall from fuckbuddy to Sissy Maid

This was the arrangement we had found worked best for us. Marion and I had been friends with benefits for a little while, before I opened up about my submissive desires. She had matched that interest and we had started exploring with some light bondage at first. Our relationship would change forever when I revealed that humiliation turned me on and that I fantasized about being 'forced' to cross-dress while being bossed around. She asked if I owner any woman clothes, and I revealed that I owned a French maid outfit, and some bra and panties, but had only dressed up alone. Her eyes lit up at the idea of having a sissy-maid. She was not the most tidy person I knew, and she was going to take full advantage of the situation.

"I could definitely use a maid around here..." she had said, before reaching for the handcuffs. She had sat on my face, telling me how "I could start cleaning her pussy". After a night that left both of us spent, and my tongue and jaw sore, she made me promise to bring my French maid outfit the next week. On the way home I received a message saying "Tonight was the best we had together! I can't wait to see you in a dress, I'm so excited!". Ironically, that night would mark the beginning of me rapidly losing the privilege of fucking her.

While she had enjoyed the bondage play we indulged in, my coming out as a sissy seemed to make her discover a whole new side of herself, which she embraced fully. When I came back next week she was visibly excited. She kissed me at the door and brought me to the living room. There she sat me on the couch, and immediately asked me to show her the dress. It took all my will-power to not back out, reminding myself that I wanted this. I then took out the dress from the duffle bag I had brought along.

She almost ripped it out of my hands, and held it up at arms length to admire it. It was a basic maid outfit I had bought online, yet she exclaimed "Oh my god it's so cute... That's really girly, I wouldn't even wear something so... PINK!", making me blush. She sensed my nervousness and added "I'm sure you'll look delicious in it!". She then asked me to show her the rest of the duffle bag, and with a deep breath I handed her the lacy panties, bra, and garter belt, all in white, and the fishnet stocking I had bought. She took them off my hands and commented "A matching set... Someone is looking to get fucked!".

Finally, I pulled out a pair of high heels. While the rest of my outfit was pretty simple, very much 'Sissy's first outfit', I had paid specific care to selecting the heels, the most important part of the outfit in my opinion (but that might be my foot fetish speaking). They were 5.5inch stiletto heels, with a 1 inch platform. Black and strappy, they were definitely designed to look sexy more than classy. Fuck-me pumps as Amy Winehouse would say.

She carefully examined them before asking :

- "Can you walk in those? They look hot as fuck, but I can't imagine how sore I'd be if I wore those to a bar or a club?".

- "I'm not really good at it, I've only worn them alone, and I usually wasn't walking around..." I replied, pointing to my dick.

She laughed and said "Well, you're gonna have plenty of time to learn... Can you dress up for me? I've been waiting for this all week!". She sensed my hesitation, and grabbed my hand, bringing it to her panties, where a wet spot had been forming. She made me rub her panties, as I watched the wet patch grow, and she insisted "Pretty please?", batting her eyelashes at me.

Something about her genuine excitement convinced me to take the leap, so I asked:

"Can I at least change in private?"

"Sure," she agreed, "but get naked here, you won't need those clothes tonight."

It was a small request really, nothing she hadn't seen before, but it made my blood surge to my dick. She was slipping into the role of a domme quite naturally, making sure she regained control of the narrative. I blushed and silently undressed and moved to the kitchen, trying to hide my semi.

There, I took some time to calm my nerves and build back my confidence. This was a woman who I trusted. We had fooled around plenty of times, and I have enjoyed the kinky exploration we shared. Sure, this was pushing things at least 3 levels of kinky further, but when else would I get to live my fantasies? I made the resolution to go all in on this and embrace the moment, as embarrassing as it was. Truth be told, the humiliation I was feeling was kinda the whole point.

I got changed, starting with the fishnet stockings and garter belt, then pulling on the panties above it (the proper order of doing things if you don't want your panties to be trapped by the garter belt!). Next, I put on the bra, and the dress. Finally I slipped into the heels, realizing that she had a point regarding the height of the heels. It hadn't been an issue until now, as when playing alone I would barely take a few steps, striking a few sexy poses in front of the mirror before inevitably playing with myself, but I didn't know how long I could wear them.

I hesitated to put on the wig I had kept hidden in the duffel bag, but eventually decided to put it on. First of all, if I wanted to be all in, I needed to be all in, but what really convinced me was that the more passable I looked, the less 'ridiculous' I would feel. Looking like a woman was emasculating, but much less humiliating that being obviously a man in woman's clothes. I checked myself out using the oven as a mirror: with the blonde wig on I was quite passable. I had a rather small frame, a barely visible Adam's apple, and a gentle face. One more deep breath and I was stepping out into the living room, where Marion was waiting for me, on the edge of her seat.

As soon as I came into view she stood up with big, excited, screams.

"OH MY GOD! You have a WIG?! You look so good! I can't wait to undress you and have my way with you! Take some steps so I can see? Turn around, show me that ass and those legs in those heels!"

It felt like she had just gotten the best Christmas present of her life, and her excitement helped me relax. She was clearly enjoying this, and I was literally living my fantasies. I did as I was told, and took some small steps towards her, trying not to fall in these heels which were definitely to tall for my own good. Once I was a few steps away from her, I turned around to show her my ass, and in a cheeky moment decided to lift my skirt, flashing my panty-clad ass to her, which she approved of loudly.

She asked me to come closer and started walking around me, devouring every inch of me with her eyes. I tried turning around with her to keep facing her, but he told me to "Stand still." with natural authority and I immediately complied, slowly falling into my submissive persona. She looked at my legs and said "Damn girl, you have to shave though, you can't be wearing fishnet stockings with hairy legs!".

She immediately covered her mouth with both hands, as if she was afraid her comment might have broken her new toy. She said "I'm sorry, that came out harsher than I meant. It's just you look pretty decent but that was such a fashion faux-pas. And am I supposed to refer to you as Girl? Dude? Brotato?".

Her breaking character was oddly reassuring, and I let out the remaining anxiety I felt with a genuine laugh, which seemed to reassure her. She asked me again how I wanted her to refer me, explaining that while she found the whole thing really hot she didn't know what was in it for me.

Eyes glued on the floor, I decided to explain to her:

"You can call me whatever you want, you're in charge. The humiliation is a turn on for me. The more feminine, the sluttier, you 'make me', the more emasculated I feel, the better. So 'Girl' is just fine. The idea of being bossed around while feminized is a huge turn on as well."

"So... The more womanly you look the better? And you like when I tell you what to do?" she asked, looking for confirmation?

She was right, but admitting it out loud made me blush two shades deeper.

"Then you definitely need to shave before next time, no self-respecting girl would wear anything but pants with those hairy legs. Especially not fishnet stockings that are gonna attract attention like that... Oh! I have an idea!"

She rushed to her purse, and came back with a lipstick tube. "Pucker up" she ordered, and I made a kissy face. She applied some lipstick and said "There, bright red! Nice and slutty.". She pulled me to a mirror, and told me to give her a duckface "What do you think?" I was amazed by the effect the lipstick was having. The bright color was attracting my gaze to my lips, and away from the more masculine parts of my face, making me drastically more passable. "I like it," I said, "A lot!".

She dragged me back to the couch, and started making out with me. Eventually she grabbed my dick and broke the kiss. As she pulled away, she smirked and said "Wow, with the smeared lipstick you do look like a slut!" which made my dick twitch. She noticed and started stroking my dick "You like being called a slut?" to which I could only reply with a quiet "Yes.". That seemed to give her an idea, because she started slowly stroking my dick while asking me questions. As I fell deeper and deeper into sub space, I forced myself to be truly honest during this interrogation, as I knew that it would us to better sex. What I didn't realize was how much power she would get out knowing my kinkiest secrets.

- "Are you afraid of being shaved under your 'normal' clothes."

- "Yes."

- "Does it excite you?"

- "Also yes."

- "Why aren't you playing with my pussy. Or at least my tits. Usually by now you'd be all over me."

- I blushed heavily, but replied honestly "You haven't given me permission."

- "Oh, permission, Sounds fun! Kiss my nipples please!"

I gladly accepted, kissing and licking one nipple after the other. After a few minutes of that, she stopped me and continued her questioning:

- "What happens if you touch me without permission?"

- "I guess you would punish me."

- "Punish you how? Spank you?" she asked almost laughing, but I took her question seriously.

- "Classic stuff like spankings always works, although I'm not really into pain. But it's up to you really, whatever you think is appropriate, and would humiliate me or bring me back in line."

- "I have a few ex-boyfriends who could probably have used some punishment for being douches." she said, trying to break the tension.

So far we had always been equal partners in the bedroom. Even when she tied me up, we were still both on a pretty equal footing despite being tied. But I could see the gears turning in her head as she was slowly coming to grips with the fact that, this time, she was completely in charge. And loving it.

- "So... You're not allowed to touch me without permission?" I nodded. "And you liked being bossed around." I nodded again. "So can I punish you if you DON'T do what I say?" I nodded one last time, and a bright smile lit up her face.

- "I'm gonna looove that! You're gonna be eating a lot of pussy!"

I quipped back, "Have I ever NOT licked your pussy?"

- "No, but you've been pretty good at getting a blowjob in return, or at cutting it short to fuck me silly."

She had a point, but what can I say, I like getting my dick sucked, and I liked fucking, sue me.

- "Actually, there was that one time when you came over for a quickie after clubbing."

- "Come on, it was a 3AM quickie and we were both sweaty."

- "Are you giving me lip, slut?" she asked in fake angry voice.

- "No, Miss, of course not, Miss." I replied in a stereotypically demure voice.

- "Well, suffice to say that won't be an acceptable excuse anymore and I won't return the favor as often anymore. Now why don't you put your mouth where your mouth is right now." she answered, back to a more serious voice. Then she added "And I like the 'Miss' thing, that might actually become a thing.".

I remember getting a bit worried back then at her mentioning less blowjobs in the future, but seeing that she said that while playing with dick, I didn't give it much thought. I added another cheeky "Yes Miss", and she pushed me off the couch. Not needing any extra hint, I fell to my knees and dove between her legs. It was true that I almost never refused to lick her pussy, but today I could tell the dynamic had shifted. This wasn't just some entree before we fucked each other, she was making herself comfortable as I dove in. I got the feeling I would be down there a while, which she confirmed: "Slow down, we've got plenty of time.".

I obeyed and started teasing her with my tongue, tracing large circles around her clit, only briefly darting my tongue over it to keep her on edge. I was pacing myself, taking some small breaks here and there, kissing above her thighs and the area above her pussy, before returning to the teasing. I started trying to fuck her with my tongue, going as deep as I could, which got some encouraging moans out of her. Eventually, during one of my 'breaks', she grabbed my head and forcefully shoved it back, so I increased the attention I was giving her clit. I created some suction around it with my lips, while quickly flicking my tongue all over it, careful not to apply too much pressure.

She reacted by holding my head harder and grinding her pussy in my face, which made my dick twitch down below. This is probably around the time I would usually stop and start fucking her instead: she was hot and ready to go, and so was I. But this time, I let her grind on my face, trying my best to keep giving her clit the attention it deserved. It took quite a while longer, at which point my jaw was starting to get sore, but eventually she screamed "Keep going, keep going I'm gonna cum.". That gave me a second wind, convincing me to push through the pain, and I was soon rewarded with a flood of juice invading my mouth. Dutifully, I lapped it all up, quite satisfied with my performance.

I kept licking slowly, staying away from the clit as I knew it would probably be over-sensitive by now, until she pushed me away. I awkwardly stayed on my knees, waiting for her to recover, hard as a rock. When she did, she let out a soft sigh, and asked "Can you bring me some water please?". I carefully rose to my feet, getting a chuckle out of her, then slowly went to the kitchen to bring her a glass of water, sitting down next to her as I handed it to her.

She thanked me, drinking it straight and started telling me how much she enjoyed it, absent mindedly playing with my dick. Soon enough, she had started slowly jerking me off again, asking me questions again.

"So I should punish you if you touch me without permission, anything else I should punish you for?"

Sticking to my 'honesty is the best policy' decision, I told her:

"For anything you want really. You can give me an order and punish me if I don't obey, or if you feel like I didn't do it well enough, or fast enough. You make the rules, and get to decide if I broke them."

She pondered that thought for a while and said "What if you don't enjoy the rules? What if I ask you something you're not comfortable with? "

"If you ask me to do something I'm not ok with, I'll let you know don't worry. I also want to have fun." We would evolve to a safe-word system later down the line, but basic communication was more than enough to begin with. "But honestly, I've had these fantasies for years and they've grown quite wild, I'm pretty sure I can handle whatever you throw my way. Besides, being 'forced' to do things I don't want to do, or that are demeaning, is a big part of the turn on. Am I really a sissy maid if I'm only doing things I enjoy?"

A playful flame lit up in her eyes, but she still had some restraints. "It still feels like I'm exploiting you.".

I pointed at my dick in her hands and said "Oh no, poor me, being all taken advantage off." Then in my horny mind I decided to open Pandora's box: "I'm serious, chances are that what you consider 'pushing too far' or 'taking advantage of me' is something I've fantasized over and would do without a second though. Let's see, what's the craziest thing you could think of asking me to do right now? Something you think would definitely be taking advantage. I'll tell you how close to my limit it is, no judgement, I promise."