Sissy, Hypnotized – Transgender – Crossdressers

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Sissy, Hypnotized

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny frame only accentuated by some slight curves in my ass and legs that I had worked on for the last couple of months.

It had started with porn, as I imagine it always does. First came the vanilla stuff, 18-year-old blonde pornstars being fucked silly by studs with gigantic rods. Then one day when browsing, I’d seen a pornstar squirming desperately as she was railed against a wall. I noticed that she had a little something ‘extra’, and the twist that this gorgeous babe had a cock made me cum twice as hard as I normally did. After that, my tastes changed to exclusively trans and crossdressing porn, and then I had discovered sissy hypnosis. It hit my mind like an erotic bombshell.

I hadn’t had a girlfriend by that point, and my school days had been full of mediocrity and perfectionist parenting. I’d been ignored by the female sex my entire life, and suddenly my head was bombarded by the devastatingly powerful experience that is sissy hypno. Lights, flashing images, quick cuts from one beautiful girl to the next, jacking up arousal through novelty and abusing the lowered defences that come from being turned on to get into my brain. I was hooked. It seemed like in no time at all, ‘fuck the girl’ turned into ‘get fucked like a girl’, and ‘get a girlfriend’ turned into ‘be a girl’.

And so, six months ago in April when I finally moved out from my parents on my own, I was faced with the lethal combination that is complete freedom to do as I please, and watching sissy hypno every day. It had moved on from just the quick cuts – I listened to sissy hypno before bed and as I slept, and it was the first thing I wanted to do when I woke up. I was addicted.

Many of the hypnos implanted triggers – one hypno in particular above the rest. It was called ‘Bambi Sleep’. It was wickedly subversive and powerful, and I’d zoned out for hours and even days listening to it. The triggers it implanted in me were many and they were deep. Luckily, none the phrases came up too often in waking life – although once my friend had mentioned the Disney film ‘Bambi’, and I’d felt compelled to excuse myself and masturbate as soon as possible.

My new found freedom culminated in several horny online shopping sprees – first the chastity cage, then panties, lingerie, bodystockings, fishnets, bras, chokers. I spent a fair chunk of my student loan. To compensate, my eating habits adjusted to two meals of pasta or noodles per day. When I was horny – which was now all the time – I just wasn’t hungry. I had never been the biggest guy around, but after a couple of months I was skinny as a rail.

The chastity cage had sealed the deal. Wearing it completely changed both my mindset and my behavior. It extended what had previously been shameful jerking in front of a computer to the rest of my waking life. There is something subversively powerful about the way it prevents erections and normal masturbation, and yet never allows you to forget that you are wearing it. It’s the ultimate act of masochism – making yourself be horny but never allowing yourself release. It made me feel so submissive, and so girly! I began shaving, wearing panties all the time, painting my toenails. My collection of clothes began to be augmented with dresses, skirts and blouses. I began to fantasise about going out dressed up. I spent hours watching makeup tutorials, and trying to do squats in my room to build up my butt wearing leggings. Of course, I had no keyholder, so nothing prevented me from taking it off at the end of everyday and pathetically jerking my semi-erect penis. But still, I was so ready to pop that I always came before I was fully hard, and as a result, I hadn’t had a full erection since March.

But a new idea – of going out dressed as a girl – had begun to take hold in my brain. I’d been out wearing my cage before, but only ever dressed as a boy (except for the panties). I’d been handed a flyer in the city center the week previously about a dress-up club night on Halloween, and it had planted the seed in my brain. What better time to try my first time out than on Halloween? Hell, if I wasn’t crossdressing I would be in the minority surely – loads of guys dressed up as girls for Halloween right?

I still told myself I was straight – this was all just fun because of the sissy porn right? After I came, the standard waves of guilt overcame me, and I came close to throwing it all away sometimes. I had had dreams of losing my virginity finally at University, and I knew that all of this stuff was not helping. I told myself that this Halloween would be the culmination of everything, this was the farthest I would ever take it. I wasn’t gay, I told myself, so I wasn’t going to do all the cock sucking and fucking like in all the hypno videos. Yeah they made me cum hard and fast, but I wouldn’t do that in real life right? I just liked dressing up as a girl and getting off – that didn’t make me gay.

And so, this had all resulted in the plan tonight. I was going to go out as a girl. I shivered at the very idea, wondering if I should back out, but I was fairly invested at that point. I’d already painted my nails red and shaped my eyebrows. I’d been wearing my cage for three days now – there was no need of my dick tonight! It was funny, I had reflected to myself, eight months ago I was obsessed with losing my virginity. And now I was breaking my own record for chastity before a night out! As I had walked to the shower, the padlock had tinkled slightly against the cage body, causing a wave of pleasure rush through me.

Now smooth and hairless, I tore my eyes away from the cage, and walked slowly over to my bed, the padlock clicking as I moved. My clothes were all laid out, ready and waiting. First I slipped on my favorite pair of panties, the most pink and girly I had been able to find – I guess the sissy hypno had got to me a little, I conceded. Hipster cut, with black lace trim, I pulled them up my frictionless legs and over my constrained bulge. They pulled into my ass nicely. Next I put on on my sheer black pantyhose, the fabric gliding up my smooth legs. I rolled up one leg and then the other, before pulling them over my pink panties.

I snapped on a pink bra to match, put in some breast forms, and then considered the main outfit. As it was Halloween, I had figured I couldn’t just ‘go out like a woman’, so I had picked 1950’s housewife as my costume. I slipped the polka dot halter neck red-and-black mini dress off of the hanger and stepped into it. I tugged it over my bra and pulled it over my head. The dress fit perfectly, pulling in at my waist before billowing out in a perfect circle around my stocking-clad legs.

Next, I moved over to the bathroom mirror. Everything was laid out in front of me: first went the foundation, then the powder. I stuck on some false eyelashes, before moving on to my mouth. I applied a coat of deep, ruby red lipstick to match the dress. Finally, I slipped on a hairnet and an perfectly coiffed blonde wig.

I turned around, stepped into my beautiful 3″ heels, and walked over to the floor-length mirror in the corner of my small one-room apartment. The image of 50’s perfection stared back at me – a cute, wicked red mouth, innocent blue eyes, ditsy blonde hair and a perfect dress. My constrained penis. well, clit I guess (clit at this point seemed more appropriate than penis) twitched in my cage. I was a smoking 10/10, my billowing dress revealing a hint of my lower thigh but hiding my straining secret. I was a blonde bombshell who wouldn’t look out of place as a pinup girl. I was sexy, desirable, looking soft and fuckable. I was ready to go out!

The bar was loud, dark and crowded. I nervously tottered in, and I swore that everyone was looking at me. “Look at that sissy go,” I imagined they were saying to one another, “what a slut!”. I felt my cage with every step, and hoped like crazy no one could see it. What was I doing!

Of course, it’s doubtful anyone was actually paying me that much attention, I said to myself. The club was full of weird and wonderful costumes worn by all persons of indeterminate gender, and there was always another fancy dress look to ogle. I saw Tinkerbell, a couple of zombies, a pilot, three cat girls and a whole host of costumes besides. And I look better than all of them, girls and boys, I thought to myself, savoring a small thrill of pride.

I knew I looked stunning, and I was surprised at the warm glow of happiness I felt every time I noticed someone checking me out. Three times on the short walk to the bar I noticed a person giving me the once over. I’d practiced with the heels over the last week, but I still felt a little unsteady. I self-consciously stuck out my ass a little, and tried to balance with my hips, which meant that I swayed from side to side as I walked like a model on a catwalk.

I finally made it to the bar, gratefully grabbing the edge to steady myself, between a girl dressed up as a slutty cat and a generic caveman.

“Can I buy you a drink?,” I heard a voice over the blaring music.

I turned, and looked up at the questioner. Even wearing my heels he towered over me – a tall man in a double-breasted pilot’s uniform. I was small at 5’5 without them, and this guy must have been at least 6’3. He smiled, and doffed his Captain’s hat.

“You’re very convincing. The only giveaway was your walk, you need more practice. Otherwise, you’re a very good girl. Let me treat you like one – can I buy you a drink?”

I smiled back demurely, and dipped my head in a nod, blushing under my foundation. His smile broadened, and he stepped up closer, his hand lightly touching my back. When he called me a ‘good girl’, I shivered, and I felt a movement in my cage. That was a hypno trigger! Dammit!

“Perfect – don’t talk. Let’s keep the illusion going for everyone else. It can be our. little secret.”

I blushed again, intimately aware that he was insinuating the size of my pe- no. My clitty. He ordered three double shots of rum cream & whiskey, and a diet coke. He paid, and picked up the coke as the harassed barman poured the shots. He slid his hand from the small of my back to my opposite hip.

I was feeling slightly worried – were those shots for me? Or for both of us? I stared at the shots – the rum cream gave all three of them the appearance of a shot glass full of cum. The sissy hypno that I had been watching was tickling my subconsciousness, interacting with the horniness from the chastity cage. I hope those are all for me, I thought. No I don’t!

He turned his face toward my ear.”Now, like most crossdressers, I imagine you’re straight – don’t worry! I believe you,” he whispered in my ear. “But tonight, you’re just playing the girl – 1950’s housewife if I’m not mistaken. Is that right?”

I nodded again, feeling very hot as he pressed up from behind me, still acutely away of his left hand on my hip. He set his drink down and moved his right hand to my right hip.

“That’s okay,” he continued in my ear, “lots of crossdressers come out on Halloween, it’s the perfect time! But I think you’re a bit different. You’ve made the classic mistake you see- you’ve put so much effort in, and it’s a bit of a giveaway. That, and you look like Bambi in the headlights!”

I gave a small gasp and I felt my cage gave another little twitch when he mentioned Bambi. He must know! How much does he know, or guess – was it a coincidence? I need to get out of here! But as much as I felt I didn’t want this, another deeper part of me. did want it. Needed it. You can’t get yourself off, it said to me. So why not get someone else off? Why not talk to this guy? Suck him? Fuck him? It would make you feel *so* girly! Do it girl! You sissy!

I tried to shake off these thoughts, but I was so conflicted I felt frozen, and my welcome/unwelcome suitor continued.

“But I might be wrong! So let’s play a game shall we? True or false. If it’s true – take the shot! If it’s false, I’ll take it. Okay? We’ll avoid names for now, but I guess Bambi is as good a name as any – you still look wobbly! Is that okay?

I nodded, my head of swirl of conflicted thoughts, my ears pounding from the music, my clit straining in its cage. Why did he have to use that name, that word? He must know, surely! He pressed up behind me. I could smell his cologne.

“It’s a great costume, but there would be no need to wear panties, right? You’d only wear them if you wanted to feel girly, it adds nothing to the look. However. I guess you are wearing panties.”

I felt his hand move under my dress in one quick motion, feel the fabric of my underwear and retreat, quicker than blinking. I knew there was no way he could mistake the silky touch of my panties, and felt a tidal wave of embarrassment mixed with desire wash through me. He picked up the milky shot glass, and and brought it to my lips. The shot smelled strong and I gagged slightly. He tipped it back, and the milky substance washed around my mouth. It tasted surprisingly good – was that Fireball whiskey? I swallowed.

He laughed a deep, satisfied laugh. “Okay, one to nothing. I bet you enjoyed that shot though! Let me guess again. Even though you could have worn opaque tights, you’ve shaved your legs. I’m going to guess you’ve shaved everything else and. I might be out on a limb here. you have no hair below the eyebrows.”

He was still pressed up behind me, so he didn’t see me smile. Despite my embarrassment, I was glad that he could have no idea I had shaved a landing strip above my cage. But the pressure from his hands on my hips increased, he pushed into me and suddenly –

“Wait! Except your crotch. I’m guessing you have a . landing strip!”

I gave a small gasp. How could he know! I spun around and looked him in the face, shaking my head violently. He grinned broadly, and I could see triumph in his eyes. Around us, bodies danced and music played in the darkness. No one was paying us any attention. No one could hear us. He reached over my shoulder and picked up the second shot, offering it to me while staring me dead in the face.

“Don’t make me check, Bambi”, he murmured and winked wickedly. Face flushing with shame, clit pulsing in my cage under my dress, I defiantly took the shot and downed it. It made me splutter slightly. He took the glass from my unresisting fingers and switched it with the last shot on the bar. He moved his body close to mine, and I looked up into his eyes. My heart was pounding and my cage was exerting a painful yet pleasurable pressure on my clit as it tried and failed to get hard. My head was clouded with lust and I felt the buzz from the alcohol beginning.

“And finally, sissy,” he said, his face and lips inches from my own as he pulled me close, “I bet you are a virgin wearing a chastity cage, who secretly hoped she would find a stud she could suck off. Is that right, Bambi?”

I felt like I was paralyzed and I just stood there in my dress and heels, my cage straining, my painted lips moving, no sound coming out of my beautiful mouth. He smiled lazily as he brought the final shot up and tipped it down my throat. I couldn’t help but swallow. He snaked his free hand behind and grabbed my ass beneath my dress, through my panties.

He maintained eye-contact and his lazy smile as he slowly brought his hand round to the front, and held my cage lightly, his hand still over my panties.

“Here’s what’s going to happen, Bambi. You can be a good girl and leave this place with me, to go back to yours. You will give me the keys to this cage, so I can help you stay a good girl, and you will get a nice reward. Just nod your head for yes, or shake your head for no. The choice is yours, sissy girl.”

I hesitated. My cage felt ready to burst in my panties. I felt so sexy in my outfit, and so submissive in my cage.

The cab ride was like nothing I had ever experienced. My date had spent several minutes of hushed conversation with the driver, with frequent glances from both back at me. It was cold in the night air – as well as the chill on my sheathed legs and bare arms, I could feel the eyes of club goers, taxi drivers and bouncers roving over me. I tried to avoid eye contact – several of these people had seen my entry not ten minutes ago, and here I was getting into a cab with a man. The look in the eyes of the boys said “what a lucky guy,” which the look in the eyes of the girls said “what a slut”. My clitty stirred in its cage, and a gust of wind threatened to expose my secret. I tried to tug my dress down, looking like Marilyn Monroe, as several onlookers whistled and cat-called.

I saw a significant cash exchanged, and then I was beckoned over. I slid into the cab, my dress riding up for a moment, before I closed my legs and smoothed it down demurely. He climbed in from the other side, and the door closed, shutting out the wind and the jeers. The taxi started moving, and he looked at me.

“I don’t want you to lose interest, sissy girl, so I brought a gift for you. Don’t mind the cab driver.”

Before I had a chance to react, he had slid over to my side of the cab, kissed me softly on the lips, one hand went up the inside of my thigh and-

I suddenly felt a wonderful sensation, pleasure my little clitty hadn’t had since I’d locked it up a couple of days ago. It felt as if beautiful pulses of light were throbbing through my cage, making me squirm with delight. I moaned, my eyes closed.

“I couldn’t have my little girl Bambi losing interest on the way,” he whispered in my ear, “so I brought along a little sissy toy for you. Do you like it?”

“Yes,” I breathed. I was lost in the sensation. My clitty felt fantastic inside her little cage and writhed with pleasure in the backseat. To be so denied and so teased simultaneously was such a delicious sensation, and his whispered words were connecting to heart of all my darkest fantasies.

“You’re such a good sissy girl, locking up your clitty. Making sure no one could confuse it for what it is. You looked so beautiful and feminine and you gave yourself a clitty to match. All you want to do is give pleasure, is that right Bambi? You just want to be a girl?”

“Yes,” I moaned again, my legs tight around the vibrator and his arms, locking it into place on my clitty. I could feel myself leaking into my panties, but I didn’t care. I didn’t care about anything he was saying. Inside, I could feel my girl-loving, straight self retreating deep inside. He was still whispering:

“But you are a slut aren’t you? Dressing up like this and cruising for cock? Like a whore? A dirty sissy whore? My sexy sissy slut Bambi, who loves to suck cock and dress up like a whore. You’re going to stay a virgin forever, never having sex with a woman, only giving yourself as a woman to men. Bambi, sleep with me. “

My straight self was shouting inside, but it all seemed to be coming from far away, across a deep vast lake of arousal. I want to have sex, it shouted, I want to see boobs! I want to fuck girls! But this desperate shout went unheeded. The triggers he had wittingly or unwittingly release had removed control from me, and Bambi was now in charge. I was lost to the deep sensations of desire and lust radiating out from my vibrating cage. The endless sissy hypno I had watched had created a sissy alter ego that was in firm control, in blissful paradise dreaming about being a beautiful submissive sissy, giving herself and serving.

“Do you want to cum Bambi? Do you want to cum for me?”

I nodded vigorously, anticipating release, squeezing my legs tight –

by Slipperylock © 11 comments / 32873 views / 48 favorites

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