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Sissification, Sissy Stories
Turned Into Full-Time Sissy Maid: Locktober Feminization Story, Final Part
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 the final part of her reply.
Read Part 1 | Read Part 2 | Read Part 3
“I still vividly remember the peculiar design of that bathroom. The interior was somewhat between rococo and coquette style, in a mixture of pastel pink and gold colours, which made me drift away for a second: like what if I were a tough old-school businessman staying for a night at this hotel (yes, at that moment I was literally the exact opposite of that man but still), wouldn’t this type of bathroom scare me off, isn’t it easier to make bathrooms in a more gender-neutral style to accommodate all tastes, why would they choose such a feminine design, more fitting to how my Mistress would decorate my bathroom, and why…
‘Emily?’
A knock on the bathroom door brought me back to the reality. Turns out, I was standing there for quite a while, in that coincidentally awfully feminine bathroom with lipgloss in my hand, water running from the tap for some reason. I guess it was easier for my mind to feverishly wander off literally in any direction away from the stress of my situation than facing it. And rightfully so. Here I was, in a hotel, touching up my makeup at Mistress’s instruction and adjusting the low back of my halter neck dress that was rather determined to slip down, revealing my painfully tight waist cincher. All in preparation to give a blowjob to a guy, waiting for me in the next room. A guy I’m about to meet for the first time. A real fucking guy. And a real fucking blowjob.
‘Yes, Mistress, I’m coming, one second,’ I replied with terror still inhabiting all the corners of my soul. Well, obviously this exact situation was something a 23-year-old James, for example, would fantasize about in his wildest wettest dreams. But if by a swing of a magic wand James, that blissfully unaware boy, would turn into a beautiful woman, applying lipgloss and imagining the stains it would leave on a cock he’s about to blow – wouldn’t the reality be too much to take? Well, it certainly was too much for me.
But then, a rapid thought came across my mind. I didn’t get into this situation in an instant, did I? That boy had had a long walk in high heels to get to this point. And was I really the same James who envisioned these lewd fantasies all these years ago? Was I really James at all? Or the whole year of basically living as a full-time sissy maid, being unconditionally feminized by Mistress and, no less significantly, being forced to wear an inverted chastity cage for a month – has all of it shaped me into someone new? Someone who regardless of the radical nature of his sissifcation was not only enjoying it but… was feeling more and more comfortable seeing this exact reflection in the mirror every day?
I closed the lipgloss and reached to put it away in my clutch. The lipgloss slipped across the side of the clutch and fell to the floor. As I bent down from the waist in a graceful ladylike manner instilled in me with numerous hours of practice, my eyes caught the beam of light sliding along my smooth shiny gorgeous legs covered in bronze shimmer. That moment encapsulated so much of pure femininity that when I rose back up and glanced one last time in the mirror, without any contemplation whatsoever, I saw Emily daintily touching up the gloss on her upper lip with a french tip manicured finger. It was such a small gesture but it being so feminine and completely unconscious made me not only see Emily but actually feel like her. And unlike James, Emily wouldn’t mind giving a blowjob, would she? This thought made my clitty twitch, reminding me of the sweet precious orgasms I was promised and, weirdly enough, all this calmed me a bit.
But all the traces of this frail tranquility vanished as soon as entered the room and saw Isaac sitting at the table, talking to Mistress. He was handsome, clearly very fit and athletic, with short dark hair and a slightly brownish beard that was neatly trimmed. He had a rather classy but stylish vibe with his dark green khaki polo shirt tucked into high-waisted beige pants, his Dr Martens dark brogs shining. What a weird choice of clothing for a blowjob from a sissy in a hotel, I thought. But at least he looked kind of nice…
When he heard my heels clicking he instantly turned to me and for a tiny moment a hint of surprise appeared on his confident but rather charming face.
‘Emily, darling, that took you long enough!’ Mistress said when she saw me. She then turned to Isaac, ‘Sorry, dear, us girls have to make sure we always look perfect, don’t we?’ she turned back to me.
‘Erm… Yes, Mis…’ I paused for a second, not too comfortable addressing my Mistress in front of another man.
‘Mistress. It’s OK, you can say it. Isaac doesn’t mind.’
‘Erm… Yes, of course, Mistress.’ I replied too ashamed to look into Isaac’s face to learn his reaction.
‘Oh, right, how rude of me. Isaac, meet my precious sweet Emily.’
He rose from the chair walked up to me, took my daintily stretched-out hand, kissed it and said,
‘Hi, Emily. Pleasure to finally meet you.’
‘Hi, Isaac. Erm… likewise.’
‘Jeez, how formal. It’s like you’re about to ask her for a ball or something haha,’ Mistress said.
Both Isaac and I blushed. Isaac, however, was pretty swift to regain his confidence.
‘Well, she looks very beautiful, stunning in fact, so you never know…’
‘Oh, how nice of you,’ Mistress replied with a smile. ‘What you say, Emily? Up for a date?’
Yeah, what’s the opposite of calmness? Multiply it by a thousand and you would still not quite get what I was feeling in that moment. All that mental prep in the bathroom seemingly waisted…
‘Oh, come on, sweetie, don’t get all worked up, not yet at least haha, I’m just kidding. Come have a drink with us.’
Isaac moved a third chair, conveniently next to his, and I had no choice but to sit down side by side with him. We drank a little bit more wine. Mistress was trying to steer a casual conversation about something I can’t even recall, Isaac was polite and rather lively, or at least he was trying to appear so. As for me, I was just sitting there, legs crossed, straight posture, head held high, as I was taught to, and yet very quiet and lost deep in the anxiety of this whole moment. However, as time went by, and as the wine was kicking in again, Isaac seemed more and more pleasant, with no comments or even looks with any hint of judgment drawn towards the outrageous fact that it was a conversation held between Mistress, her sissy and a guy being there solely for the purpose of getting a blowjob from that very sissy. In fact, it felt as normal as it could be, just 2 ladies, just a guy, just sipping wine. Much later, I learned that not only Isaac’s cousin was a drag queen but he also previously had had a brief relationship with a trans woman. Not sure, if he was a chaser or just a very open-minded person, but him being so tactful and OK with this whole situation Mistress had arranged, was certainly helping me relax a bit. Some nice background music coming from Mistress’s phone also contributed to the pleasant atmosphere.
Then Mistress said,
‘Can I just say, I can’t stop admiring how gorgeous Emily looks tonight, doesn’t she?’
‘Oh, yes, absolutely,’ Isaac picked up. ‘This colour looks so good on you and I love the, what’s it called, drape? Haha, sorry, not too good at this stuff.’
I smiled. Alright, now I understood Mistress’s genius choice of my dress for the night.
‘Well, anyway, yes. Emily, you look very, very sexy,’ he said and some weird seductive tones appeared in his voice which made me feel rather unsettled. And then his masculine hand landed on my thigh and started to gently caress it.
‘Emily, darling, such a nice handsome man complimented you. Not too ladylike of you to not say anything in return,’ Mistress said playfully, pushing me out of my disturbed silence.
‘Oh, yes, sorry. I’m just, you know, not very used to receiving such compliments,’ I replied, still pretty sheepishly.
‘Really? I thought you received them daily,’ Isaac said with his hand still caressing my thigh. That was a bit cringe, to be honest. Are men really that awkward when horny? Poor girls. But a quick glance at Mistress and her slight twitch of an eyebrow made it clear to me that it was a one-way route I couldn’t escape.
‘Oh, Isaac, you’re so sweet. Thank you.’ Not knowing what more to say, I slowly swang my ankle and touched his leg in a manner that I considered to be feminine and sexy. And turned out it was.
‘You know, I’m really glad Beth arranged this,’ Isaac continued in a deeper quieter voice, taking note of my ankle rubbing against his.
After some moments of silence, Mistress intervened,
‘Oh, I’m sure Emily thinks the same. Such a shy girl.’
I’ve read the pushy notes in Mistress’s words. She wasn’t quite pleased with me yet.
‘The feeling’s mutual,’ I muttered in a voice as horny and sweet as I could master. And actually, as hard as it was to admit there was some part of me that wasn’t quite sure it was a lie.
‘A music to my ears,’ Isaac said as he leaned forward, took my chin, brought it up and passionately kissed me on the lips.
Holy fuck, that was unexpected. For some reason, the blowjob in my mind wasn’t as bad as actually kissing a guy, acting horny for him and making it seem like a usual date. But that kiss made my clitty twitch more intensely than I could’ve imagined.
‘Work with your hand, dear’ I heard a gentle whisper that sounded more like an order coming from Mistress. And so as we continued kissing I started to rub my hand against Isaac’s inner thigh slowly moving towards his crotch. There I felt it. A hard dick, trying to break away from the pants’ restraints. With no choice in the matter, I started to gently caress it with my manicured hand, my other hand reaching towards his head, first touching his hair and then wrapping around his neck.
When I felt his hand, moving down my waist towards my ass, I heard the music change. Beyonce’s ‘Dance For You’ started quietly playing in the background. I broke away from the kiss, turned to Mistress and saw her barely noticeable nod with a devilishly hot smile across her beautiful face. That was my queue.
You see, back in July of that year, when my blowjob and anal training were introduced, apart from the expected gag reflex and deepthroat training, felatio techniques, anal stretching and moving, sounding and acting like a woman during sex, Mistress went on to also school me in the feminine ways of foreplay. That included sexy movements, preferred positions and, sometimes, lap dancing. And Beyonce’s music video for ‘Dance For You’ was supposed to serve as my inspiration in that aspect of training. Mistress made me watch it numerous times, study and repeat Beyonce’s moves in every detail, and then perform her dance in front of Mistress. After that, before every blowjob or pegging session, I was supposed to perform some sort of ultra-feminine seductive foreplay. Frankly, despite being rather flexible and generally good at dancing, I wasn’t 100% proficient in that department yet. However, Mistress turning that song on certainly meant I was expected to give Isaac at least some sort of feminine divine treatment.
I turned back to Isaac, kissed him one more time, took him by the hand and gracefully walked him towards the bed. I passionately pushed him down on it, and then catwalked to the opposite side of the room to the beat of the song, hands gliding along my curves. There, with my ass turned towards him I did the bending move, with my one leg spread to the side and hands gliding up from the heel to the waist. Then I turned around dramatically, slowly and seductively got on my knees and started crawling towards him on all fours, swinging my hips as wide as I could.
When I reached him, I once again started to caress his crotch with my hands, reaching for the zipper.
‘Not so fast. Feel his body. Start with the shirt,’ Mistress, now sitting at the far end of the bed, instructed.
Following the orders, I moved my hands up his fit body. Then I untucked his shirt and slid my manicured hands below it to caress his abs. With his help I opened up his shirt, moved a bit forward and started to kiss his chest (hairless, thank god), moving down along his abs to his crotch. Then I kissed the hot and very bulgy crotch itself.
‘Good girl. Now take it out,’ Mistress commanded in a gentle whisper.
I unzipped his pants and slowly lowered his underpants until a giant dick proudly popped up. It was around 7-8 inches long and was way bigger than my clitty, especially in its current practically non-existent state. His cock was as if it was straight from porn, perfect in every way – and rather frightening in its size. Obviously, Mistress had made me train on dildos roughly the same length, if not bigger, and technically I was able to shove such monsters down my throat but still, seeing his tool made me rather nervous.
‘Good girl. Now, kiss, slowly, gently,’ Mistress continued with instructions.
I did as I was told, landing passionate kisses on the head and along the shaft. I’ll never forget that taste of precum on my lips as they wrapped around a real man’s cock for the first time in my life. A bit salty, yes, but it was somehow an altogether completely new flavour I had never experienced before, one I could only describe as ‘manhood’. I wasn’t a fan of it at all but for some reason, I felt my hornyness levels rising.
I didn’t need further instructions. Leaning the cock towards his body, I licked it from the base upwards along the shaft and then when reaching his head I finally took it all in my mouth – one of the first moves Mistress taught me. Sliding the cock up and down my soft pallette and along my cheeks, playing with my tongue, my hand making the spiral motions on his shaft I started sucking. With passion. With desire. With longing, that I never expected to feel at this moment.
A couple of moments later the dick slid down my throat as I, to my surprise, managed to reach right up to the ballsack with my lips without issues. And so the fellatio was in full swing. From time to time, Mistress would prompt me to play with his balls and suck them, or would instruct me to pause and play with my tongue around his head, or would remind me to keep moaning in pleasure, or would encourage Isaac to fuck my face. She was especially persistent in making me look upwards, showcasing my beautiful eyes. The whole lashes and brows treatment I had received earlier that day made total sense in those moments. One time when the dick was deep down my throat Mistress instructed me with a diabolical smile to leave the cock there for a bit and to flicker my tongue against his balls. That was a pro move which I wasn’t particularly successful at but me choking and pulling the cock out with mascara tears running down my cheeks apparently left Mistress satisfied nonetheless as I heard a soft laughter.
Finally, Isaac’s moans and groans became evidently more intense and the veins on his dick started to feel more present. He was nearing an orgasm which meant only one thing – I was about to taste a real man’s cum. I intensified my hands’ motions around his shaft, my tongue still rapidly playing with his head, assumed an appropriate position, also taught by Mistress, and tried to express my thirst for cum faking the excitement on my face.
‘Say, ‘I want your cum so bad, daddy’, say it like you mean it,’ Mistress commanded.
‘I want your cum so bad, daddy. Please, cum for me, daddy.’
‘Do you want to taste his cum, you slutty girl?’
‘Yes, daddy, please, I’m such a slutty girl and I want to taste your cum so much.’
‘Do you want him to fill your throat with it?’
‘Please fill my mouth and my throat with your cum, I want it so, so bad…’
And then he exploded. Warm salty slimy liquid splashed in my mouth, across my tongue, around my lips, and as it started dripping, Mistress, now standing beside me, said intensely,
‘Catch it all, Emily, not one drop wasted, come on, suck it dry.’ She kept saying that while I was wrapping my lips around his exploding head trying to catch the extra dripping cum with my hand.
As Isaac’s moans subsided, Mistress first instructed me to suck the cum off my hand, then leaned my head so that my mouth was facing upwards and ordered me to swipe the cum around my lips back into the mouth with my fingers. Once I did that she said,
‘Don’t you swallow. Open wide. Show it to me. Mm, a mouthful of tasty manly cum. You like it, don’t you sissy?’
‘Urghurgh,’ some weak assertive sounds escaped my throat that was now blocked with Isaac’s seed.
‘Hahaha, I like that sound. Roll it with your tongue, savour the taste, doll. Longer. Again. You’re my little cum whore, aren’t you, Emily? Try to say it, ‘I’m your cum whore, Mistress’.’
‘Urghg urghg khurgh krgoher’ I tried to mutter, chocking with cum.
‘Hahahaha, good girl, Emily, good girl. Now swallow. Every last drop.’
I did as I was told and the weird sensation of cum flowing down my throat with its strange texture and unsettling flavour is still to this day one of the most vivid memories from that night – and my sissyhood as a whole.
‘Don’t you want to thank Isaac?’
‘Thank you so much for your cum, daddy’ I muttered.
And then he… disappeared. No, really, I was so ashamed and yet so unbearably aroused, conflicted and stressed that I don’t even remember how he dressed up, how we said our goodbyes. Total blackout. What I remember though is what happened next.
As soon as he left Mistress approached me and whispered,
‘I don’t think I’ve ever been so horny in my life.’
As I was about to say something along the lines of “You’ve no idea what hornyness means” she shushed me and suddenly kissed me on the lips with flaring passion, not minding that these lips were covered in Isaac’s cum just several minutes ago. We made out for a while. Then she pulled back and said,
‘I’m so proud of you sweetie! Of course, there’s still a lot to work on but that was really, really impressive.’
‘Thank you, Mistress.’
‘How are you feeling?’ She asked as we sat down on the bed, the remote control plug still reminding me of its presence.
‘Honestly? Exhausted. And… confused I guess. I… can’t quite express it with words now. I don’t know, it was a lot. I just… I just wanted to make you happy.’
‘Oh, my dear sweet Emily, my love, you did! Today I’m the happiest proudest Mistress in the world! Come here,’ and she gave me the warmest most sincere hug that felt like heaven.
‘But we’re not done yet.’
‘Oh, Mistress, please, I can’t handle it anymore…’
‘I know. Let’s get you out of this slutty dress and put you into something more comfortable.’
She then took out a white lace babydoll nightie, a white garter belt and white sheer stockings from her bag. No panties – which, hopefully, was a good sign for me. She helped me out of the dress, the cincher (the relief was unworldly) and the fake breasts, and when I finally put on the nightie and aligned the stockings with the garter clasps, I turned to see Mistress wearing only her classy black underwear as well.
She approached me in an effortlessly feminine seductive manner, raised her hand to my cheek and as she was caressing it, she said,
‘You know the rules, Emily. Mistress’s pleasure comes first.’
I should’ve expected that. More so, I held this rule in very high regard. And yet the thought of postponing my, to say the least, long-awaited orgasm didn’t particularly excite me. Still, I managed to gather my last bits of will and replied,
‘Of course, Mistress. Always.’
She gently led me to the bed where she lied down and I assumed my position between her thighs. She was so wet. Indeed, my blowjob performance must have made her no less aroused than I was. Luckily, I had much more first-hand experience pleasuring my Mistress orally than in blowjobs. So, with masterful tongue movement, perfect pace and enough passion it didn’t take long for her to burst into an exploding orgasm.
‘Wow… Haven’t had such an intense one in a while,’ she exhaled after calming herself a bit.
‘Hopefully, that doesn’t mean me giving blowjobs will become more frequent,’ I replied with a smile, miraculously still having energy left for humour.
‘Haha, well, we’ll see about that. Actually, let’s hear the songs you’ll sing after I give you the promised reward,’ she said mysteriously as she rose from the bed.
Oh. My. God. Finally. FINALLY! The time had come. The sweet, sweet release… By that point, it felt like my poor tiny clitty had drilled a hole inward in my cavity. But the suffering was about to be over. After all the teasing, all the denials, all the seemingly unendurable challenges of that fateful day I was about to be rewarded with one thing I craved the most – an orgasm.
‘Speaking of which…’ Mistress said picking up her phone. ‘It’s 00:05 now, dear. Congratulations, Locktober is officially over! I don’t how we did it but we did it! Of course, I heard of Mistresses who manage to deny their sissies an orgasm for more than several months,’ I gulped,’ but I’m not so cruel. Yet. Hahaha.’
‘Thank you, Mistress. Please, Mistress, I humbly think I deserved it…’
‘Oh, Emily, you did. In fact, I remember I promised you the best orgasm of your life. And I intend to keep my promise.’
‘Oh, thank you, thank you, thank you, Mistress.’
‘And we’ve also agreed on complete trust, haven’t we?’
‘Mistress… Whatever it is, if I don’t cum right now, sperm will burst out of my eyes or something.’
‘God, no, it won’t come to this. As long as you trust me.’
‘Okay…’
‘Alright, doggie style, chest on the bed, ass up,’ Mistress said while taking our favourite 10-inch vibrating heated dildo out from her bag.
Without hesitation, I did as I was told. She climbed on the bed with me, buzzed the plug and slapped my ass a couple of times before finally taking the plug out.
‘Oh, my, look at that hungry gaping pussy,’ she said as she inserted 3 fingers in my hole, and started massaging it. ‘So loose, so hungry for cock… Are you my horny slut, Emily?’
‘Yes, I am, Mistress.’
She kept massaging my asshole for a while, now using 4 fingers and as I was trembling and shivering with my locked clitty raging I wasn’t able to resist asking the question,
‘Are you going to unlock me, Mistress?’
‘No,’ she replied firmly.
‘No? But…’ Another sudden realisation hit me. Too many for one day, if I’m being honest. Sissygasm. She wants me to have a sissygasm. Should’ve guessed as well.
‘Tonight you’re going to cum like a girl. Like a sissy girl that you are, Emily.’
‘You think I’m ready?’ I responded instantly. ‘I mean, now? What if…’
‘Oh, I’m sure you are ready now more than ever. Shush. Too much talking, too few moans,’ and as she said that she inserted the warm vibrating dildo up my ass.
In and out, in and out, pace increasing, sensations elevating, moans getting louder and girlier, Mistress’s horny talk intensifying, my inner girl trembling and squirming, my clitty in flames and my pussy in rapture.
‘Emily? You here? I said repeat after me!’
‘Yes…’
‘I’m a submissive sissy.’
‘I’m… a… submissive… sissy.’
‘I’m a girly girl.’
‘I’m… a… girly… girl.’
‘I’m not a man.’
‘I’m… not… a… man.’
‘I never was and never will be.’
‘I… never… was… and… never… will be.’
‘Rub your clitty with your hand! Repeat: I’m a girly sissy girl.’
‘I’m… a… girly… sissy girl.’
‘I am my Mistress’s whore.’
‘I… am.. my… Mistress’s… whore.’
‘My name is Emily.’
‘My… name… is… Emily.’
‘Always and forever.’
‘Always… and…’
What followed next was… divine. No words can describe the eruption of sensations I experienced at that moment. As the cum burst out of my clitty, every single cell of my exhausted body flamed up and shivered, and I released the moan every female porn star would be proud of. It was fireworks and magic and thunderstorm and explosion and every other epithet you’ve ever heard. As Mistress promised, it was the best orgasm of my life.
I collapsed, totally drained in every way, still trembling with the debris of that sensation.
‘Wow, Emily, I don’t think it took you more than a minute or two.’
‘I… It was… I’m…’
‘Oh, yes, babes, welcome to the world of female orgasms. We’ve been waiting for you doll,’ Mistress took the dildo out, put it away and lied down beside me, gently caressing my hair.
‘I love you, Emily.’
That was it. I burst into tears. Amidst the sobbing and the overflowing emotions, I think I told her ‘I love you so much’ about a thousand times. I think I was also trying to chaotically convey my conflicting thoughts on the Emily vs James dilemma. I doubt I made much sense. But I didn’t need to. Both Mistress and I already knew everything we needed to know to move forward.
The next morning I woke up as Mistress was ordering breakfast over the hotel phone.
‘Oh, sorry, sweetie, I tried to be as quiet as possible… I just got too hungry, haha.’
‘No, it’s OK, Mistress. What time is it?’
‘11, you sleepyhead! It’s alright, girls need their beauty sleep. But you should see your face now, panda bear, hahaha. It’s the last time I allow you to sleep in make-up!’
‘Oh, haha I can imagine, yeah,’ I sat up in the bed, yawning. I was still wearing the nightie and the stockings from yesterday. When I put away the blanket I noticed that I was wearing the chastity cage, which brought back all the overwhelming events from yesterday that crashed upon me like a waterfall.
Mistress noticed me looking at the chastity, and seeing me deep in troubling thoughts, she declared theatrically,
‘I present you… the key! You’re free to unlock. Go have a shower, I’ve brought some of your skincare products.’
‘Thank you, Mistress.’
It took me a couple of minutes standing in the shower and staring at the key in my hand to finally unlock the cage. The clitty sheepishly emerged from its cavity. So tiny, so… vulnerable. I realised that I now touched it for the first time in more than a month. During Locktober, I imagined this moment at least a couple of times per day, but now as I was standing in the shower, free to jerk myself off to oblivion, and I was just staring at the French manicure on my fingers holding the cage instead. My clitty was flacid. I thought that it might have been broken after a month in an inverted chastity (which obviously, it wasn’t) but I didn’t really care. All the yesterday’s dialogues with Mistress, the beauty salon, the experience of getting pampered up, the taxi ride, the blowjob, the sissygasm, it all now was forming a very coherent logic behind my new identity and for the first time in months, I wasn’t terrified while thinking about. Of course, I was still far from any definitive conclusions and yet I couldn’t help but notice the unusual clarity with which I could perceive my journey so far. And the journey that was lying ahead of me.
I came back to the hotel room, with towels wrapped around my chest and my hair. I approached Mistress.
‘Mistress, do you mind if I stay in chastity for a bit longer? No timeframe, just… well, for a while.’
I handed her the key. She seemed very surprised by my request. Still, she smiled and said,
‘Honestly, Emily, I didn’t think it would be so soon. But you’ve always been a brainy girl, haven’t you? Of course, dear.’
‘But, Mistress, I’d still want your permission to… you know… cum.’
‘Oh, sweetie, I think we’ve figured out the solution to this problem yesterday, haven’t we?’ she replied and as she went to put the key back in her bag she slapped my ass.
~~~~~~
Later that night I had 3 sissygasms in a row. 2 months later, with Mistress’s encouragement I hooked up with another guy. 3 months later we made these one-night stands a once-a-month occasion for me. A couple of guys down the road I managed to cum from a guy fucking me in my pussy. In June this year, I started HRT. I’m still wearing a chastity cage but I suppose it’s more of a habit now, I don’t think I will have any urge to masturbate even if I wasn’t locked up. Am I a trans woman? Well, I am certainly Emily, Mistress Elizabeth’s full-time sissy maid. And I certainly am happy. For now, that’s enough for me. My journey is far from being over, but as long as I’m true to myself I don’t worry about how far the feminization rabbit hole goes anymore. One high-heeled step at a time, right?
Thank you for your time, Head Mistress. Mistress Elizabeth sends her regards as well!
Forever yours,
Emily”
The End.
Quite fascinating, isn’t it? I’m now really curious though… How would you describe yourself? What stage of the sissification journey are you on right now? Tell me in the comments…
Premium Training
I’m currently at the point I think many sissies find themselves at, I need to start investing time into finding a mistress that I can enjoy the rest of my life with, one that will love the duality my sissy nature offers so I can shower my goddess with love and devotion until death do us part. 🥰
I know mine with mine I can sooo relate to Emily. Especially with my daddy. I am slowly becoming his little sissy maid. He is coming back down to visit me when he has his next weekend off. I really find myself just worshiping him. The more I am with the more aroused I become. Which just makes me even more submissive and femmie. As well as extremely emotional. Which I really love.
Hello Mistress,
Thank you for sharing Emily’s inspiring story. Reading I put myself in her shoes wishing it were my story. I’m encouraged to continue my journey of feminization, hopefully someday to please a mistress in similar fashion.
I have grown my hair to shoulder length.
I have grown my breasts naturally to a C cup. Maintaining smooth bikini tanned skin, and a trim physique. I wear bras, panties, garters, stockings etc… everyday and am continuously adding to my collection. My clit is so tiny and is incapable of erection. I can only sissygasm with a dildo in my sissy pussy. I trained my pussy to gape, and can take an 8″ diameter monster cock in my ass with ease.
I go to the nail salon for a mani/pedi every month or so. I were foundation and lipstick every day, and do full eye makeup on the weekend.
I long to venture into uncharted territory to go deeper down the rabbit hole of my sissification and often fantasize about BBC making me feel like a real woman.
I was so turned on by her getting kissed by Jason, and eating his cum. And the sissygasm was the most perfect conclusion to this whole adventure spanning weeks! I am truly grateful to have read this very very personal story for free! Thank you sissy academy!
I currently want to make my identity as Ananya more than my “male” identity. so That i Identify more as her, until I finally make the shift by sissygasm, permanent chastity and pleasing men all the time!
Thank you for this fantastic time and inspiration, Emily!
I didn’t like the whole fashion part much, not much into the details, but I covet every other part. to be a hot sexy woman forever!
Oh, Your name. Its an Indian origin name, I like it.
this afternoon a met with a pilot, while on layover, in his hotel. my wife had given me permission to see him. I went to his room in my regular clothes, but I had worn my sexy panties beneath my pants. I did my nails this morning while also cleaning my boy pussy. I felt so confident when I arrived at the hotel. I applied my red lip gloss and knocked on the door. I was so girly, smiling, giggling, touching his leg and arm as we sat on the bed. I wasted no time, as he went to the bathroom, I took off all my clothes, except for my beautiful black lace panties, I threw myself on the bed, feeling my smooth body, caressing my ciltty, my tits, waiting.
He saw me laying there, quickly undressed and held his cock. This gorgeous rock hard cock was being presented to my mouth as I purred, feeling the sleek head of his dick as I opened my lips. I was in sissy heaven.
I nuzzed his balls and licked his shaft as he quickly moved into a 69 position above me. I had his wonderful cock forced down my throat, it was so much easier than sucking my wife’s dildo.
I’m home now, recalling everything from my encounter. He actually fucked my pussy . I’m hooked on being a slut, of course with my wife’s encouragement
I would consider myself further along than Emily. Im starting HRT next month and have a BBL scheduled next year. I have been regularly waxed for 3 years..have dressed in public and have done a photo shoot. I still have plenty of ways to go and am super excited about the journey ahead..not to mention, I have enjoyed the taste and feel of cock on more than a few occasions!! Yum
I don’t need men with their lousy dicks, I’m a lesbian and I love to enjoy caressing a woman’s breasts and delicious pink pussy with my tongue, giving great pleasure to a woman.
I just loved reading every bit
of this very arousing sissy story.
I wish that this
entire sissy scenario happened to me, while I am dressed in beautiful
silky lingerie, alluring shiny satin feminine clothing, fully crossdressed and made up perfectly, while my demanding gorgeous
Mistress trains me to obey
her sissy instructions for me
to satisfy her and the many male dates
she schedules for me to gladly service.
Thank you for posting
this exciting sissy story to read.
May I please ask
for more similar stories to be posted
for me to enjoy and get me
in this same full time sissy mindset.
I am in transformation for the last four years now. Wearing female clothing started way before that . (When i was ten or eleven.) The next step , the biggest one , will be the eradication of the last traces of masculinity.
Reading stories like those above encourage me on my way to total emasculation.
I have had a sissy orgasm while riding my date it was so very strong and rewarding for the both of us. My problem is I have only been wearing sexy undies for him and have never been fully dressed I feel to uncomfortable with my height to go out dressed to his apartment, he doesn’t know my full fem side something that I need to work on.
Respected Mistress:
(curtsy)
This sissy sub still feels trembling knees after avidly finishing the story!
The vivid tale, be it real or fantasy, is the embodiment of all girl’s dreams, the perfectly portrayed ideal relationship, and the one that any sub would aim to achieve.
It also marks a precise path, Respected Superior Dame, and one that ellie, here at your feet, certainly hopes to be strong and brave enough to follow to it conclusion.
At your feet.
Respectfully
sissy ellie
I am at that stage where i am enjoying the journey i am going through cause this is all my widest dreams that are coming true so yaa . 😊
Completed module 6 in 7
Finished module 6, waiting for your permission mistress to continue module 7.😊
Oh my God , that was just an extraordinary, intoxicating, stimulating story , what a lucky sissy. Wish i had a Mistress who would do all that for me and i would spend the rest of my life trying to please my Mistress. i love cock and cum and would gladly participate in all of that , to please my Mistress
I’d say I’m like an advanced novice, I go and make a lot of progress and do a lot of things then pull out, usually because of the persecution we get from the ignorant people of our society just sucks the fun right out of the lifestyle and culture, so i go and be masc again, my priorities also change as well, like those that depend on me, depend on me successfully prospering in a mans world doing manly things for the sake of their well beings and so i put sissyhood to the side and be the man everybody needs me to be, but then, they toss me out as someone they dont need at all and so then im like i guess I’ll go be a girl again and then it becomes this whole unending cycle of being and not being, going all in to pulling all out.
Hi, for me I’m at a point of where I have numerous amounts of toys clothes and panties but every time I cum i feel
Very guilty. I haven’t got to the stage where I don’t feel guilty or ashamed. There’s been times where I purged and throw away all
My girly things but I end up buying them all back. I think this story is very encouraging and will help me accept my sissy girl side. Ps a sissygasm is the best orgasm ever. I think once you had a true sissygasm there is no going back.
Hello mistress I am currently on module 12 about halfway through it I am a complete Sissy I had just recently in the past couple weeks started HRT and I am also checking into getting my surgery done I a submissive trans girl and can’t wait to become the complete girl that I should have been I love this story and thank you so much for your guidance and for the Academy XOXOXO🥰.
man after all your stories have been read by me personally I must confess where I’m at in the feminization process after finding out about my love to be humiliated by the opposite sex I let a few women walk on me, two females made me eat there pussy after fucking another man and I liked it especially when they talked dirty & called me sissy bitch but one dominant older woman done me in by having me first accept her husband’s large cock to throat me good while she watched and supervised how to give it to me while watching and draining in commenting humiliating me to the point I have started to be feminized then the woman grabbed me by my hair punch me in the belly slap me very hard 3 or 4 times then push me down on my face and grabbed my waist and jerk my butt in the air before whispering in my ear while laying on top of me with a couple fingers up my ass how her husband was about to turn me out and bragged how much bigger his dick was than mine asking me if I was ready then making my head shake up and down with her hands as a yes just before I felt her husband Mount me and his massive cock go up me quickly as I grunted moaned and shook quivering and even jerking now and then because I was getting fucked so hard by that man my manhood escaped me and I felt myself helplessly overtaken and turning into a girl I told him I loved him a couple times then I felt him pump his nut up me then instantly I OD’d on the devastating humiliation level as he pulled out with a splatter of cum following then a slow drain seeping out of my butt as I laid and quivered for a long time with my legs still spread wide he had successfully turn me into a bitch right in front of his proud wife who gave me a dress I accepted to wear home in public and that’s where I’m at in the feminization Department thanks a lot and I’m ready for mistress to continue module 7 with my permission it’s a go
Oh My !!! OMG !!! YES !!! YES !!! OMG !!! I sooooooo LOVE…….LOVE !!!!! MORE !!! MORE !!!!! YES !!!! MORE…!!! I Sooooooo LOVE !!!!!! MORE !!! MORE !! MORE !!!!!! Ohh YES !! MORE !!!!!!! teddi
I’ve been in the phase of putting a throbbing cock in my mouth and thinking what am I doing. Do I even want this as I continued to give a blow job. I have not gotten use to the taste of cum but want to. I’ve yet to cum while getting my pussy fucked too but as I read there is a time and place for everything. I think I just need to find that one person that pushes me to that point. That’s why I am here to learn and get to that point one day. Love the story.
Reading this story made me actually eat all my pre-cum and then my own cum when it eventually flowed, and I wanted more. So powerfully erotic. Thank you, please keep them coming. I must go and get ready for the day, with all my feminine attire under my male clothes! 💋 💋
I have just started my training and am looking forward to the experience.
I do envy her having an understanding loving but firm mistress like her it’s heavenly. I do dress as a woman every day since I consider myself a trans woman I wear bra gartered stockings with a garter belt panties fake boobs of course and heels and I always thought that I was a lesbian but now thanks to your wonderful course I like to look at cocks and cannot wait for my first time giving a bj and being penetrated by a real cock I’m not quite there yet but it’s coming all that thanks to the academy thank you
Hello HMA
Thanks to the Academy for this great story.
Emily has listened to her inner voices and truly found who she really is.
Pleasing and loving her mistress, craving men and learning to worship cocks and cum,
to be pond like a girl and having sissygasms with her asspussy,
it’s a journey of dreams for the hot sexy femme Emily became. Her choice to be sissified et feminized is a boost for me.
Now into my second year of hormones with my male persona a distant memory this has been a beautiful read. Thank You Emily for sharing it with us.
I’ve gone much further than I ever imagined when I started the course even when I graduated actually, and it’s been 22 months since my last male outfit went into a recycling station on the trip back from the final visit to complete the family estate. I arrived in a costume and left dressed normally. I’m legally Natasha, taking hormones, loving my beautiful B/C cup breasts, smooth skin, hormone controlled mindset and, best of all the tiny remains of my male bits being completely irrelevant. I see them as an indication of how far I’ve developed.
To all at the Academy, my fellow students, and those who appreciate us I say a huge Thank You!!
Head Mistress Alyssa thank you for sending me a a Email but unfortunately Becca has blocked the mailbox so I cannot reply you now as you know I did apologise to everyone for my wrong doing and i went though a lot of stress when my mother passed away now not all understand how that effects a person it can lead to suicide in extreme cases so I have avoided type of thing happening to me but please Head Mistress Alyssa can unblocked the Email mailbox so I can respectfully reply you please.
Thank you
Leslie Sissy
Head Mistress Alyssa thank you for sending me a a Email but unfortunately Becca has blocked the mailbox so I cannot reply you now as you know I did apologise to everyone for my wrong doing and i went though a lot of stress when my mother passed away now not all understand how that effects a person it can lead to suicide in extreme cases so I have avoided type of thing happening to me but please Head Mistress Alyssa can unblocked the Email mailbox so I can respectfully reply you please.
Thank you
Leslie Sissy
Very well written; fast paced with the right mixture of reality and fantasy.
I have completed the first three parts, of the story but not the fourth. My last Mistress came somewhat close in having me submit women of her choosing, but not to men. I think my current Mistress will take me there when she is completely secure in her authority.
Its very scary. I am worried about my male persona. I hope i find a girlfriend soon and can put all this behind me…. I am not much of a beta man on the contrary actually and girls have proffessed theyre love to me and yet i am afraid of hurting a women, which makes me want to be the submissive, Sissy? Hopefully not. You guys are beyond! Im so confused after reading that…
I loved the story and kinda wished I could have played with my clitty while reading it, but I am coming up to 4 months locked in chastity now. I am very far along my sissy journey and still learning.
Over 6 years on hormones, beautiful natural C cup breasts from them and living and working as a full time trans woman. A completely female wardrobe and lifestyle, I am finally living my true sissy life. I am lucky to have a wonderful Mistress and I also work in an adult shop that has glory holes, so I get to suck lots of cock.
Lucky Emily. I still remember my first time with a man. I also swallowed his cum. We both were very excited.
I love this story ,i wnat to be order by Mistress
Hello Head Mistress Alyssa I just wanted the chance to wish you and Becca a Happy Christmas 2023.
Theres no hard feelings from me and I think you run a great internet site for all sissy’s.
Merry Christmas 🎄
Merry Christmas everybody