Hello, darlings. Recently, we received a very peculiar email from one of our most loyal students. She said she wouldn’t need to join Locktober this year because her Mistress had been keeping her in chastity full-time for a year now, and she no longer felt even the slightest urge to masturbate like a man. We chatted for a while, and I found her story quite fascinating. I asked her to describe a day or a week of her life as a full-time sissy maid to maybe apply her experience to our free Training. Luckily, she’s a very articulate girl, and what I received in return exceeded all of my expectations. With her permission, I decided to share her reply with my students. I think it will be quite an inspiration to you. Take notes, girls.
This is Part 3 of her reply. Read Part 1 here. Read Part 2 here.
“As I bent down to pick up the pink lace thong, as I put it on, the sensation of the plug filling my asshole, it twitching and pressuring against my prostate, made my clitty so excited, I was amazed the inverted chastity cage didn’t pop out. And the worst part was that I still had to endure the remaining 4-5 hours of October 31st and whatever it was that Mistress had planned for the evening until I would finally be allowed to cum. I suddenly thought of how much cum I would be able to generate and whether Mistress would make me eat all of it. ‘Fuck, as long as I get an orgasm, I don’t care if it’s Bukkake really,’ I thought. ‘Well, actually, I do, but I wonder what my limits are now. What Mistress’s conditions am I willing to submit to? What will I do in my uncontrollable longing for a release? 1 month in chastity has given her so much power over me… And these lashes and eyebrows, this mani and pedi, this makeup and hair, this unconditionally hot, sexy outfit I’m about to wear – it all has a higher purpose, hasn’t it? It’s all part of a plan. But a plan for what?’ Having no idea what Mistress had in store for me and knowing the ingenuity of her unyielding desire to push me further and further, I was scared as hell. But at the same time, no less excited. Which made this never-ending loop of hornyness truly unbearable.
Thankfully, I had a small break from these lewd thoughts as I now had to concentrate on creating a believable cleavage.
‘B cup, Mistress?’ I asked while reviewing the challenge that was laid out for me on her bed. Usually, it was C-cup breast forms, so I was a bit surprised.
‘Oh, yeah, B cup for this outfit,’ Mistress said in her black lingerie, long, beautiful legs encased in black stockings, as she was taking out her dress for the night from the hanger. ‘It’s a strapless bra, plus it’s push-up, so I wasn’t sure it’d be able to hold the C-cup forms. But it’s a C-cup bra nonetheless, so you gotta work with chest lift-ups. You sure you don’t need help?’
‘Let me try, Mistress. Maybe I’ll ask for your assistance.’
‘Alright. But, please, hurry, we are running a bit late.’
After my blunder with the butt plug, I knew better than to ask “What for?”, so I took the lift-up stickers and two little foam paddings that were hiding beneath them and proceeded to the first step of cleavage creation. I was always soft in the chest. In fact, I think I had a mild case of gynecomastia when I was a teenager, so there was plenty of flesh for me and Mistress to work with. For some reason, she enjoyed it so much when I pretended to play with my “breasts” during sex, or rather during our playtime with sex toys, since my clitty hadn’t entered her pussy for 8 months by then. As for outfits, for dresses and tops with decolletage, she always made sure I created the most believable ample cleavage. ‘Your chest was made for crossdressing,’ she used to say, and after rigorous training and numerous attempts, I became pretty adept at creating the illusion of having at least C-cup breasts. This time, however, it was a strapless bra, so extra effort was required.
I pushed the flesh on my left breast inward, attached the small sticky padding to the lower side of the breast, and glued the lift-up sticker to the padding. I did the same for my right breast and then connected the stickers in the middle with hooks. It instantly created a rather low cleavage, resembling a natural C-cup one but without the actual breasts. I then took the breast forms, which also had sticky bases, attached the forms to the lift-up stickers, carefully adjusting the angle at which they would be hanging, and went ahead to put on the adhesive strapless bra. It was a wonderful nude bra, a true design miracle that would be completely invisible under a backless dress, yet it would keep the breasts right where they should be. The bra had pretty high cups on the sides, but in the middle, they were practically nonexistent, connected only by a small, barely visible hook. When I adjusted the bra carefully so that neither the breast form edges nor the stickers were visible under the cups and so that the stickers and the bra hooks were perfectly aligned, I stood to review my work in the vanity mirror. Damn, that was good. The foams and the stickers added enough volume for the C-cup bra to be completely filled, while the cleavage was perfectly natural. With my dress on, it would be impossible to tell that these C-cup breasts weren’t mine.
Rather proud of my work, I said,
‘Mistress, I’m done. What do you think?’
When I turned around, she was posing in a full-length mirror, ironing out the folds of her dress with her hands moving gracefully along her majestic curves. It was a beautiful black satin ankle-length camisole dress with a side split and tiny spaghetti straps, tight-fitted at the waist and cross-strapped at the back. A black leather jacket, which I assumed would top the look, was lying on her bed now, next to my dress.
‘Wow, Mistress, the dress is gorgeous, and it complements your figure so well… I suppose it will be black Bratz platforms for you then?’
‘Yes, I was thinking of going in white sneakers, actually, but the stockings kind of demand heels. Besides, I don’t want you to be taller than me, haha. And thank you, Emily,’ seeing how good the dress looked on her lifted her mood again, which, after me arguing about the plug, was quite a relief. ‘Let me see those breasts.’
She approached me and examined my work, making me slightly turn left and right, cupping the breasts with her hands, and pushing them up and inward a bit.
‘Well, Emily, that’s flawless. Good girl. Put on your sandals, and let’s try on the waist cincher.’
‘Of course, Mistress. Thank you, Mistress.’
Smiling at Mistress’s praise but rather terrified of the cincher crushing my waist, I sat down to put on my trendy heels for the night. When I changed my 5-inch pink marabou platforms to 4.5-inch sandals with clear straps, I stood up and walked a bit to see if they fit – and they did perfectly.
‘Feels OK? Good. Now this will be a hard one to close,’ Mistress said while lifting the cincher from the bed. ‘Your dress is 25 inches at the waist, but it’s a bit stretchy, so maybe 26 will be enough.’
As I already mentioned, my usual maid corsets were around 26.5 inches back then, so the challenge lying ahead of us was indeed tough. Manageable but still tough. Especially, because the nude cincher was not the usual lace-up one. It was more like an underbust training cincher girls would wear at the gym, which closed at the front with four rows of hooks and a zipper. It still had 15 metal bones, and they would create a perfect hourglass illusion if my rib cage and my inner organs would be flexible enough to squeeze into it.
‘Alright, hands up, breathe in, and… try not to pass out,’ Mistress said as she wrapped the cincher around my waist and proceeded to close the hooks. She was aiming for the tightest of the four rows, so she had to apply some remarkable strength. But apparently, it wasn’t enough. After the first 3 out of 12 hooks were closed, she already hit an uncloseable one. A minute or two of huffing and puffing later, she said,
‘Alright, that’s not gonna work. You need to watch that figure, Emily! Or maybe we need a full-time corset regime…’
‘I’m sorry, Mistress. I will do my best to bring those inches down. What are we going to do with the dress?’
‘Hm, there’s one thing that might still work. Come,’ She took me by the hand, and we went down to our basement gym. ‘Hang on this horizontal bar for me, please.’
I did as I was told, and, miraculously, hooks started to close. Mistress still had to try her hardest, and my hands started to hurt from hanging after a while. We even had to take a break because of that, but in the end, the hooks were closed and the zipper was pulled up.
‘Damn,’ Mistress said while breathing heavily. ‘That was harder than I thought. Phew… How are you feeling?’
‘I can barely breathe, and I feel my ribs are gonna crack, but it’s ok, I’ll manage, Mistress,’ I replied with my hand going up and down below my breasts, as if my touch would somehow resurrect my crushed lungs.
‘Good girl. But I can say it was totally worth it. Jesus, look at that waist…’ she pointed at the wall mirror in our gym, rather astonished. And it was something to be stunned by.
Not only was my waist in that crushing cincher smaller than hers and by quite a margin, but it gave me curves to die for. My ass, plumped by regular lower body gym sessions, looked huge, with heels bringing it up and the cincher pushing the excess flesh down to my hips and buttocks, accentuating the now very feminine proportions. Up top, my breast somehow looked even bigger, and the cleavage now fell even lower. I posed and turned a couple of times, bringing my hands to my now 26-inch waist, which quite possibly could have been even smaller; we didn’t measure it. I was amazed. And incredibly aroused. Then I felt Mistress’s hands gliding from the top of the cincher along the curved metal bones down to my butt.
‘You’re so sexy, Emily. I want you so much now,’ I felt her mint breath near my ear as she whispered in her sexy dominant voice. She then slapped my ass, and as it wiggled like a proper woman’s butt, my plug once again reminded me of its presence.
‘Oh, Mistress…’
‘Not yet, though,’ she suddenly said in a strict voice and pushed back. ‘I have a lot of stuff planned, and we still need to see how that dress looks.’
Several minutes later, Mistress was adjusting the low back of my halterneck dress so that it would cover the cincher.
‘Damn, Emily, we should have gone to a solarium. Tan lines from a bra would have looked so sexy in this outfit. Why haven’t I thought of it earlier? Well, next time.’
‘Thank god, you haven’t,’ I pondered while admiring my reflection in the mirror. I couldn’t help but feel frightened of how far this whole feminization and sissification had gone. And how far it could still possibly go. Here I was, a 28-year-old man who would never in a million years be recognised as a man, standing in beautiful high-heeled sandals as if walking in heels was second nature to me, gorgeous bronze shimmered legs positioned in a dainty manner, a side drape caressing my smooth left ankle, a halterneck tight-fitting pink mini-dress encasing my tiny waist and feminine curves, a perfect cleavage of C-cup breasts displayed in the open, deliberately suggestive and eye-catching, dainty hands with French tips manicure, beautified with very feminine rings and dangling bracelets, now touching huge rhinestone tassel drop earrings and checking if they were aligned properly, blonde curled strands from a Barbie updo brushing against my cheeks, wet glossed pink lips opened in a sexy way and huge eyes, staring from below the lavish sparkling pink and silver smokey makeup, enhanced by contacts, eyelash extensions and perfectly trimmed laminated eyebrows. For the first time ever, I thought that I could actually pass as a woman. Shoulders were a tad too broad, and there were still some excessive muscles in the arms and the neck (excessive for a woman, of course; for a man, it was as if there were no muscles at all); hips could have been a bit more naturally curvy and a bit softer; and facial features in some tiny details wouldn’t mind a FFS treatment (God, I hoped Mistress weren’t aware of these things I noticed), but for the most part, I looked like a beautiful, sexy young woman. And all that with an inverted chastity cage pushing my clitty far inside the cavity and a remote control butt plug forcing me to mindlessly crave a release.
A sudden buzz in my asshole brought me back to reality.
‘Gorgeous, aren’t we, love?’ Mistress walked up beside me, holding the plug’s remote control.
‘Oh, Mistress, please…’
‘Hush. Let’s take selfies!’
For the next 15 minutes or so, Mistress and I posed for cute, sexy photos in the mirror. She even made me take a couple of selfies myself, alone, to further instil my blossoming femininity at that moment.
‘God, we are so hot! And, giirl, you are a natural model,’ she said while briefly reviewing the photos on her phone. ‘Alright, let’s grab our purses and call a cab.’
‘A cab, Mistress?’
‘Yes, sweetheart, we are going to a hotel. I’ll be drinking, and I’m not trusting you to drive in heels. Not yet, anyway.’
So it was going out in full fem, after all. Granted, a hotel lobby was much less of a public place than a mall, but I still felt uneasy. At least my gorgeous look for the night would help with confidence.
‘You forgot your lipgloss, Emily,’ she said as I approached her with a silver clutch.
‘Oh, right, I’m sorry, Mistress,’ I said and added the lipgloss to the perfume bottle, a compact mirror, a pack of condoms, and a phone that were already placed in the clutch.
I was wrapping the waist belt around my trench coat in the hallway downstairs when Mistress came down in her black leather jacket, wearing Bratz platforms, holding a chastity key in one hand and a large purse, presumably filled with toys, in the other. As she reached to put the key in her purse in a slow, teasing manner, she paused for a second.
‘Actually…,’ she said, looking at me. ‘I wonder if…’
She walked up to me and… Nope, not what you think. In fact, something much worse. She took the key and placed it in my cleavage.
‘Hahaha, it works! Well, why wouldn’t it with such breasts? You now possess the feminine hiding spot, Emily!’
‘Oh, alright, Mistress, yes, I see, of course,’ I mumbled, trying to withstand the humiliation of this moment.
‘I’m going to take it out once we reach the destination, don’t want you sneaking away in the bathroom or anything of that sort, but until we get there, let the key stay in your cleavage. Feels firm?’
‘Umm, yes, Mistress, the cleavage can hold it,’ I replied, looking down, feeling the cold metal between my breasts – and my clitty crying and breaking in its cavity, as if sensing that the release was so close now and yet still so unreachable. A key to my own chastity in my own cleavage… As I said, my Mistress’s ingenuity knows no limits.
‘Should’ve thought of it earlier. So fun!’ Mistress said smiling, evidently pleased with herself. ‘Alright, the cab has arrived. Remember our lessons, Emily, butt first, legs closed together next.’
A sudden realization that the cab driver would see me dressed as a woman hit me. To make matters worse, Mistress called Uber Business, where the driver opens the doors for you.
‘Good evening, ladies!’ A handsome, tall driver greeted us while opening the back door.
‘Hii!’ Mistress replied, stepping aside and letting me in first. As I was walking up to the car door, the driver gave me a hand to step down from the high sidewalk onto the road. Gracefully, I lifted up my dainty hand, placed it in his, and nodded to him, forcing a smile of gratitude on my face. Then, keeping my shiny legs together and adjusting the coat and the dress with one hand from beneath, I sat on the car couch, first facing the sidewalk. Only then, I lifted my heels and turned on my butt, still keeping the legs together. The door closed, and, placing the silver clutch on my lap, I finally settled, relieved that I didn’t mess it up. A moment later, the second door opened, and Mistress entered the car no less gracefully. She turned to me and nodded with a smile of approval.
‘Music?’ the driver asked as we took off.
‘Can we connect? Oh, OK! What you say, Emily? Your playlist? It’s a 30-minute ride, I think,’ Mistress suggested in a way that usually meant an order.
“My” playlist was the incredibly girly 10-hour playlist Mistress made me on Spotify at the start of my journey. She named it “Bublegum Bitch” after MARINA’s song. It had it all, from classics to 2000s pop, from 2010s R’n’B to late 2010s bedroom pop, from Whitney Houston and Beyonce to Ariana Grande and Lana Del Ray, all female artists, all suited for a teenage girl prancing around in her bedroom, using her Dyson as a microphone. Mistress then said that by the end of the year, she wanted to see 10 songs from this playlist in my “Spotify Wrapped” (annually, Spotify creates a personalized top 10 most-listened-to songs of the year). So, yeah, having lost count of what exact songs I listened to the most, I had to come back to this playlist all the time just to make sure Mistress’s demand would be fulfilled by the end of the year. And, jumping ahead, it would be. Obviously, Spotify considered me to be a girly girl, so the Wrapped would be styled in all pink that year, which would make it rather humiliating to share with friends…
Well, anyway, back on October 31st, we were driving through the traffic to Olivia Rodrigo’s Good 4 U. Suddenly, Mistress’s hand reached to my inner thigh and then my panties. Her fingers started to gently caress my cage, and seeing my surprised face as I was hornily gasping for air, she asked,
‘So, Emily, that boy you were telling me about… How was your date?’
THE WHAT? I looked at the driver. He was minding his business, but he would clearly hear everything we said. Need I tell you that I wasn’t quite comfortable discussing boys at the back of his cab, not to mention that I had no idea what Mistress was talking about?
‘Ermm, Mi… Hm, Beth, what date are we talking about?’
I felt Mistress’s long, manicured nails painfully squeeze my balls. I didn’t use my girl voice properly. Thank God, I said it quietly, almost whispering, so it didn’t quite catch the driver’s attention. By then, I hadn’t yet attended any voice feminization classes online, despite Mistress “advertising” them to me constantly. However, I still had to look up a couple of lessons and practice all the time as Mistress demanded I “was speaking like a lady” when I was tending to my sissy maid duties.
‘You slutty girl,’ she replied playfully. In the back mirror, I saw the driver slightly lift his eyebrows. ‘So many dates, you can’t keep up, I see! We were talking about James, I believe…’
‘Ah, James, haha, yes, that guy, he was nice…’ And so, in a more appropriate voice, I entered one of the most uncomfortable dialogues I had ever been a part of. I can’t quite recall what stuff I made up, but Mistress was sure to ask me about all of the details of my “date” with James: how he looked, what we talked about, where we had our walk after the restaurant, did he lend me his jacket as he walked me home, did I invite him, did I kiss him goodnight… The cub drive seemed to be endless, but my imagination wasn’t. Thankfully, just as I was nearing its limits, we arrived at the hotel.
As we were checking in, yet another ‘Good evening, ladies!’ from the usher and all the eyes we turned as we were swinging our asses in heels down the lobby only added to my angst. Which was actually mixed with very weird but quite pleasant shivers running down my spine. I couldn’t comprehend this feeling, but I had other stuff on my mind. For example, why did Mistress make me talk about boyfriends in the cab, and, most importantly, what were we doing at this 5-star hotel? We entered a luxurious room, and as I was taking my trench coat off, I instantly said,
‘Mistress, I’m sorry, but I felt really uncomfortable in the car…’
‘Did you? I think you got quite excited by the end of your story. “Gave him a French kiss, agreed to have another night out in a week…” Makes me wonder if you are ready for actual dates, babe.’
‘Erm… Well, I had to make up something! But couldn’t the driver tell I wasn’t a girl? After all, my voice…’
‘That’s what you’re worried about? Baby, please, your voice was fine, and no guy, even in broad daylight, would have taken you for anyone but a beautiful woman.’
‘Thank you, Mistress, but still…’
‘It spawns some thoughts, though, that in all that girl’s bathroom talk, the most worrying thing for you was how passable you were… Means we gotta amp up your feminization even more! Then, when you are the most feminine, the most passable woman ever, we could discuss boys whenever and wherever, haha!’
‘That’s not what… Alright, Mistress, as you say, Mistress,’ seeing her still in very good mood, I didn’t want to bring it down by talking back ahead of whatever she had planned for me, so I put a pin on that discussion.
Mistress ordered some wine, and 10 minutes later we were sitting at the table, two beautiful, elegant ladies dressed for the occasion, opening a bottle of Rosé. Only that one of these girls still had a huge butt plug up her ass and a tiny chastity cage on her clitty.
‘To your big night, Emily!’ Mistress raised her glass.
‘Thank you, Mistress… For everything…’ I returned the toast with my manicured hand, still wondering what that “big night” held for me.
‘You’re welcome, my love.’
We sipped the wine, and damn, was it good. After such a stressful day, which apparently was far from over, the warmth inside made me relax.
‘Speaking of… The key, please,’ Mistress demanded as she put the glass down and reached out her open hand towards me.
I took my chastity cage key out of my cleavage (even to this day – what a weird sentence) and handed it to her. As she was taking it away, I asked,
‘Mistress, why are we here? What have you planned?’
She took out her phone, briefly texted something to someone (which terrified me to the bone), then put the phone down and said, in a serious tone,
‘You’re right, Emily, let’s talk about it. Whatever happens tonight, I want you to know that I love you very much,’ fuck, that did the opposite of calming me down, ’and that I’ve been enjoying our journey this year no less than you were. I love you as James, and I love you as Emily. Remember our morning conversation? In terms of sex, I do love Emily more. And in terms of your… identity, well, I find Emily much more fun. I would have asked you about your thoughts on this matter, but I know you find it… confusing. Personally, I have a pretty solid theory on how you feel and why. More so, I’m willing to test it. I’m pretty sure I’m doing what’s best for you and for us. But I need your complete trust.’
She paused, allowing me to reply.
‘Mistress, I’m… I love you too, and it’s been incredible, I can’t believe how lucky I am, how wonderful you are, and… But I’m scared, Mistress,’ I said, and for some reason my voice trembled as I was on the verge of tears.
‘I know you are, sweetie,’ she instantly stood up, came up to me, took my hands, and sat on her heels, her beautiful hazel eyes looking up with care and love. ‘I know you are. But I think you are so brave! Actually, you are the bravest guy, or rather girl, haha, I’ve ever dated. Fuck those gym dudes, would they ever be brave enough and confident in their masculinity enough to go to a mani and pedi?’
‘No, I guess, no, haha,’ I replied with a smile.
‘But you are! And among other beautiful things, I love this about you. You just need a little push from time to time, and that’s why I need you to trust me again. I’ve been taking you further and further this whole year. You’ve been reluctant at times, to say the least, but have I ever let you down? Have I ever stepped further than you would have secretly wanted me to?’
‘Well, that mall trip was very stressful…’
‘And since then, have I made you go out in public as a woman again? Excluding tonight. And don’t you feel more confident and relaxed tonight?’
‘I guess so, and yes, I do… Thank you, Elizabeth. Thank you, Mistress.’ And as I said that, I guess something changed in my eyes or in my facial expression. Mistress saw what she wanted to see even before I said it out loud. Such an empath.
‘So,’ she rose up high, came back to her phone, and asked without looking at me, as she already knew the answer, ’I have your complete trust tonight?’
‘Yes, Mistress.’
‘Good girl. Now,’ she put her phone away again and sat down, bringing the usual comforting dominance back to her poise, ‘tonight I’m going to give a choice. Remember Isaac? A guy I hooked up with a couple of months ago?’
‘Yes…’ I looked at her phone, and a sudden realization hit me. ‘Elizabeth!’
‘Hush. I thought we agreed on complete trust. And what on Earth was that ‘Elizabeth’? You think I softened up? It’s Mistress, now, always, and forever.’
Still in terror, I nodded, but before I could open my mouth to carry on with my distress, Mistress continued,
‘OK, so he’s about to knock on this door any minute. I told him about you, and he seemed very excited. I guess you could say he’s bisexual. Or gay. Which would have been sad if we didn’t agree with you on one-night stands only. Well, either way, here are your two options. Either you sit here and watch him fuck me senseless all night. But I won’t let you out of your cage. Maybe I’ll allow you to cum with the vibrator. I know it’s against the rules, but, well, it’s me who makes the rules for you, sweetie. The second option is that I will give you the best orgasm of your life—not even one, I suppose, but… you will have to give Isaac a blowjob.’
To say that I was stunned was to say nothing. No release? After all the teasing tonight? After such an exhausting month? It’s so cruel! Cruel to the point of being unlike her. But a blowjob? To a fucking guy? Yes, Mistress made me practice on dildos, but to A REAL FUCKING GUY? More so, to a guy who knows about me? What does he know, by the way? And what does ‘the best orgasm of my life’ mean?
‘So, what will it be?’ Mistress interrupted my spiraling thoughts, which I obviously kept to myself. But how the fuck was I supposed to choose? To be honest, the idea of watching Mistress have sex with another guy didn’t particularly excite me. Giving a blowjob, on the other hand… No, I didn’t want to do it! But for some reason, this idea made my clitty twitch.
‘Clock’s ticking. Should I give you a little buzz to speed things up?’ Mistress said holding the butt plug remote control. And then there was a knock on the door.
‘Emily!’ Mistress asked. She seemed annoyed and excited at the same time.
‘Yes, Mistress, yes, I think…’ that knock made me shiver. I was literally shaking at this point. It was as if this choice would determine my whole sissy life. Or maybe my life as a whole. My life as Emily?.. Hm, what would Emily prefer? ‘I think… Only the blowjob, right, Mistess?’
‘What, you want more, my sweet sissy whore? Haha. But no, hun, only blowjob. After that, he’s gone.’
‘OK… It will be the blowjob, Mistress.’
With flames lighting up in her eyes, Mistress approached me, still holding the plug control, kissed me on the lips, and gently whispered, ‘Good girl.’
She then turned the plug on, threw it on the bed, and said while walking to the door, ‘Go touch up your makeup while I greet him.’
Unable to say anything with the plug buzzing in my asshole, making my orgasm cravings unbearable, I rushed to turn it off. By the time I stood up with a hysterical urge to run to Mistress and beg her on my knees to not do any of this horrible stuff, I already heard the deep voice greeting her. It was too late to change anything. Not that I could, obviously… Ah, fuck it.
I went into the bathroom, turned the water tap on, and looked at my reflection. It was so beautiful. And so scared. Which actually made me even prettier. Such a powerful, gorgeous look, such a scared little soul… What a fucking day. And the most challenging part of it had just begun.”
End of Part 3. Read Part 4, the Final Part, here.
