“That’s the last time!” I said to myself, kicking off the high heel stilettos, unclipping the stockings, and stripping off my luxury lace french basque. I rushed into the bathroom to clean up, staring at myself in the mirror.
‘Look at you! You pathetic sissy,’ I murmured to myself.
After removing my makeup and showering off, I hurriedly stuffed all my female clothing into a black trash bag and dumped it by the back door. I was going to purge, and this would be the last time. I said to myself reassuringly.
The next day, I woke up, put on my shirt and trousers, and headed into the office. I was wearing boxer briefs under my clothing and it felt good to be dressed like a man again like somehow I’d regained some masculinity. I walked into the office with a new sense of confidence as I headed for the lobby.
The elevator was empty as I stepped in, pressing the button for my floor. Just as the doors were about to close, a well-manicured hand slipped through, stopping the motion and making the doors retract.
‘Oh no!’
It was Amber, the office slut and most scantily dressed girl in the building. My inner sissy was infatuated with her. I’d spent many hours jealously watching her from across the office, studying her gestures and mannerisms, envying her outfits.
Her heels clicked loudly on the marble floor as she stepped inside the elevator.
“Hiya, babe,” she curtsied.
I smiled at her bashfully, mesmerized by her gorgeous outfit.
‘Why?’ I thought, ‘Why did she have to be working today!’
As the elevator doors closed shut, she reached into her handbag, pulled out a stick of gloss, then seductively began applying it slowly around her luscious lips.
Every movement was purposeful. She was a creature of elegance, delicate and dainty, full of feminine grace and sex appeal.
My inner sissy yearned to imitate her. To mimic her promiscuous nature, to replicate her look, to dress as sexy and slutty as she did. I could feel my heart begin to race as I stared down at her glamorous strappy high heels, imagining the feeling of wearing them.
The sound of the doors opening snapped my attention, bringing me back down to earth as I watched Amber strut out of the elevator and across the floor. Grabbing the attention of the whole office. I followed meekly behind, sitting down at my desk, continuing to watch as she greeted her colleagues flirtatiously.
For the rest of the day, I fought the urge to look at her. Desperately struggling not to notice the way her skirt stretched tightly against her pantyhose as she gently wiggled in her seat. The way her long curly hair draped lusciously over her luxurious silk blouse, and the faint outline of her voluptuous bustier barely visible through the silk material.
‘For fucks sake, stop it!’ I thought, turning to look away once more.
By the end of the day, my head was spinning. Unable to focus on anything else. When I finally returned home, all I could think about was dressing up. Racing to collect the bag of clothes that lurked by the back door.
‘Just one last time!’ I promised myself.
In a frenzy, I rummaged through the contents in search of the perfect combo, something that resembled Amber’s sexy outfit. Enjoying the sensation as I slid on the bustier, clipping the stockings in place, then tucking myself back as I slipped on some satin panties, sending shivers down my spine.
‘God, I loved this!’ I thought, slowly lifting the skirt up over my ass and zipping it tight.
After slipping on a silk blouse and some high heels, I rushed to don a wig, applying a thick coat of lip gloss, mimicking Amber’s mannerisms. Within minutes the urge took over and I began masturbating to my reflection in the full-length mirror.
My moans filled the room as I unloaded my juices, sending orgasmic streams of come all over the mirror. Teetering in my heels as the last few drops splashed against it and began slowly running down the glass, creating a sticky blur over my reflection.
‘You fucking sissy!’ I heard a voice inside my head repeating loudly.
“That’s it,” I proclaimed, “no more!”
Stripping off, then stuffing the items back inside the bag.
After a quick shower, I slung on a t-shirt and a pair of jogging bottoms then picked up the bag and tossed it into a trash can in the back alley.
For the next week, I felt a sense of normality again.
Amber had been away on business calls and hadn’t been in the office for days. The other girls at work all dressed very conservatively, which helped me to focus on my work and not fantasize about their clothing. I felt like I’d beaten the addiction and no longer had the urge to dress.
That was until the fateful Friday.
Amber had returned from a business trip and looked, even more, sluttier than usual. She wore a pair of 8″ suede pump heels coupled with an inappropriately short tight black skirt. I could see the faint line of her nylons where the top of her pantyhose ended, protruding from the hem.
Her v-neck blouse tucked into her skirt, showing off her curves and exposing her deep cleavage and large breasts. Her hair was pinned back and she appeared to be wearing some fake glasses, completing the ‘office slut’ look that she was clearly going for.
My eyes widened, sending a pulse of erotic energy to my groin, making my heart skip and my mouth began to water.
“She looks so fucking sexy!” The voice inside my head screamed. “You know you want to be just like her, don’t you sissy!”
I could almost hear myself begging in agreement. My heart pounded inside my chest as I studied her style, her posture, her pure and sexual femininity.
My breath became still as I watched silently, motionless. Frozen in a trance, my mind wildly planning out the next sissy session and what types of clothing I would wear.
‘No!’ I thought, ‘I don’t do that anymore.’
The internal struggle continued, forging a battle between my inner sissy and my stubborn self, desperately trying to cling on to whatever sense of masculinity I still had left. It seemed futile to resist the urge, despite my sincere and often determined attempts.
The voice grew louder, “come on sissy, you know you want to dress up and act slutty… just like Amber!”
It was true and I knew it. I did want that, more than anything.
As the day drew to a close, I finished my work, grabbed my jacket, and headed for the elevator. I was alone as it descended into the lobby. My mind raced the whole way down, fantasizing about all the sexy clothing and lingerie I wished to wear.
‘Fuck!’ I thought, remembering the moment I had thrown it all away. The brassieres, stockings, heels, dresses, makeup, and wigs.
On the train ride home, I flicked through dozens of websites, searching for clothing and putting together a wish list of items. By the time I arrived home, I had several baskets all saved on my browser, totaling over 500 dollars.
“Come on, sissy. You can afford it!” The voice screamed, possessing my consciousness and taking control of my hand as I clicked to buy.
“Good girl!” she said, pleasingly.
‘Shit’, I mumbled under my breath, regrettably. ‘Why was I like this? What the fuck was wrong with me? Why couldn’t I just enjoy having normal sex and not feel the need to dress like a girl.’
For the remainder of the night, I lay slumped on the couch feeling sorry for myself, watching nostalgic movies while greedily spooning ice cream into my mouth. I hated myself for being so weird, so introverted. All I wanted was to be like everyone else and not this reclusive sissy that spent my days yearning for sexual kinks.
The sound of the doorbell woke me up. Still, on the couch, an empty tub of Häagen-Dazs perched on my chest. The buzzer sounded again, making me jump and rush over to answer the door. A large man stood waiting impatiently holding several parcels and some boxes.
“Sign here,” he said, thrusting a tablet towards me.
I’d almost forgotten how much I ordered, reaching over to take each package as he passed them to me. I placed them on the coffee table, then thanked him and locked the door tight behind him. This was going to take some time, I thought to myself gleefully.
After a quick shower and shave, I began opening the packages, slowly and joyfully picking out each item and admiring it before slipping them on briefly. There was such a large assortment of items, from seductive silky dresses, skirts, and blouses, to an array of naughty lingerie items such as stockings, garters, brassieres, and panties.
I was in sissy heaven!
Nothing made me happier than trying on a pair of silky pink panties, sliding on some sheer stockings, or slipping on a tight sexy dress and admiring my reflection in the mirror. After quickly trying on a few more items, I decided to dress completely en femme.
Complete with makeup and a long flowing brunette wig, I slipped on my new strappy pump high heels and stepped towards the mirror once more.
I could see the outline of my erection protruding through my skirt, my whole body tingling with excitement as slid my hands over the soft material.
“Doesn’t that feel better sissy?” The voice in my head whispered rhetorically.
‘Oh yes,’ I thought, practicing my movements as I danced and flirted with my reflection.
A sudden noise startled me as the doorbell buzzed once more. Confused and panicked I stood still, unable to think or move. Quietly, I tip-toed across the room and peered through the peek hole in the door. It was another delivery.
I considered ignoring it, but also didn’t want to miss it either. Cautiously opening the door and cowering to avoid eye contact.
The delivery man offered me the package, staring down at my long legs and grinning to himself. I couldn’t tell if he knew I was a crossdresser, or simply just liked what he saw. Snatching the parcel and closing the door quickly.
My heart was beating hard in my chest. Still shaking from the thrill of the experience, I opened the box to reveal my brand new realistic vibrating cock. The irony I thought. Little did he know what naughty plans I had in store. What kinky things I was about to do!
Overwhelmed with eroticism, I dropped to my knees, using the suction cup to attach it to the wall. Sucking and swallowing the dildo in a frenzy of lust. ‘I needed this,’ I told myself, gagging on every inch.
It didn’t take long before I found myself in the bedroom, my skirt pulled up past my waist, my panties around my ankles, the dildo penetrating me deeply as I masturbated vigorously.
“Fuck me!” I screamed, picturing myself as Amber getting fucked in the office. Imagining her facial expressions, her moans, and sounds as she arched back, taking every inch of cock like a good slut.
As I climaxed, I fell back onto the mattress, shooting streams of come over my chest and onto my face. My tongue instinctively slid out my mouth and licked up several drops that splattered onto my lips.
I could hear the voice in my head mocking and degrading me.
“You dirty little whore, look at you. You’re such a slutty come guzzling sissy. You couldn’t help yourself, could you? I bet you would have sucked off that delivery guy if he’d have come onto you, wouldn’t you!”
I lay there for a moment, accepting my truth. Maybe I was just a sissy crossdresser, I thought. Slowly, lifting myself off the bed and starting to undress. I felt the shame creeping in as I caught a glimpse of myself in the mirror.
‘Look at you. So pathetic!’
The thought of dressing up disgusted me and I could feel myself trying to pluck up the courage to end this charade once and for all. Once more I began bundling the clothes back inside a trash bag. I got as far as the back gate before turning around and dragging the bag back inside the house.
After cleaning up, I slumped onto the couch in a state of confused depression. An onslaught of questions hammered away inside my brain.
What’s wrong with you, why are you like this? Why can’t you stop dressing up?
Emotionally exhausted, I finally nodded off.
While I slept, I had the most vivid dream. Somehow, I had morphed into Amber and was now living her life. Everyone accepted me this way, and I could finally relish dressing sultry for every second of the day. Women envied me, men lusted after me. I was a feminine being full of seduction and sex appeal.
It was almost 1 am when I awoke, a wet patch around my crotch, my PJ’s stained with come. After a quick shower, I looked at myself in the mirror. Something felt different. I couldn’t tell what it was but my mind felt more clear, and for the first time in a long time the voice in my head was gone.
I was desperate to dress, sliding on a matching shiny thong and bra set, followed by a daring wet look mini dress that clung to my skin. As I slipped on some glossy heels and a long curly blonde wig, I stared back at myself in the mirror.
‘Yes,’ I thought, ‘let’s do this!’ then grabbed my keys and headed out the door to see where the night would take me.
