I was around seventeen the first time my sister and her friends decided to play a prank on me. I was minding my own business when all of a sudden my sister Jessica barged into my room, along with her best friends Karly and Regina.
"Hey sissy boy," Regina squealed in her sassy voice. I sat on my bed reading as Jessica stormed over to me, slapping the book out of my hands. I looked up at her, a puzzled expression on my face. "What is it?" I asked.
She peered down at me, a look of glee in her eyes. "My friends are bored and we thought of a great idea!" She smiled mischievously. "We're going to see if we can make you look like a girl."
"What!" I snapped. "No way!"
Regina stepped forward placing her hand firmly on my shoulder, "yes way! You're going to love it!"
Jessica grabbed my other shoulder and the two of them pulled me up off the bed, dragging me out of my room and into her bedroom. Karly joined in, pushing me forward from behind. I wasn't a big guy and with them all being several years older, I was easily overpowered by the three of them all pulling and pushing me at the same time.
"This is stupid, let me go!" I shouted. "I'll tell mom, I will!" I whined pathetically.
They all laughed, pushing me down onto Jessica's bed. "I'll tell mom!" They squealed in a high whiney tone, mocking me and laughing more.
Regina towered over me in her open-toed four-inch high heeled. Of all of my sister's friends, I had always found her the most intimidating because of her gorgeous looks and over-confident personality. She had long dark hair, big round hazel eyes, a slim but buxom figure, long silky legs and full-bosomed breasts.
"Strip!" she said, standing impatiently, her hands on her hips, tapping her fingers against her waist.
I slowly pulled my jumper up over my head, staring up at her like a little lost puppy, hoping she would let this stop. The three of them stared down at me, frustrated by how long I was taking to remove my clothes.
"Come on, hurry up sissy!" Regina yelled.
I stripped off quicker, removing the rest of my clothes, all except for my undies. I was terrified of going naked in front of them. I knew they had all seen naked men before, I had heard them through the wall, talking about their experiences during my sister's sleepovers.
Jessica had now started ruffling through her dresser drawers looking for clothing items for me, while Karly sat crossed legged, a silly grin on her face. "Come on," she said smiling at me, "take them off, girls don't wear boys' pants."
My hands seemed pressed, involuntarily over my penis, holding my underwear up. Regina snapped, leaning in and grabbing my undies, yanking them down off my legs. "Oh my god!" she screamed, pointing down between my legs as I quickly tried to cover myself. "It looks so cute!" She screamed, smiling at Karly.
"Oh, it does, doesn't it," agreed Karly, the two of them giggled together.
Jessica tossed Regina a lacey black pair of Brazilian panties, "I not going near that thing," she said, "quick, make him tuck it away." Regina forced the panties into my hands, motioning me to stand up, lifting my feet one by one and helping me slide them up over my legs.
"Now tuck that cute little thing back between your legs," she said, smiling as she pulled the panties up over my bum, the elastic wrapping tightly around my waist and pressing hard against my pelvis. Jessica tossed a matching black lace bra over to Karly who stood up and wandered over, holding the bra outstretched between her hands.
"Hands forward," she said softly, sliding the straps over my arms. I felt distracted by her low cut floral dress that revealed her gorgeous round bosoms and tantalizing cleavage. The sweet smell of her perfume making me feel lightheaded as she leaned forward and fastened the bra behind my back.
"Look what I found," Jessica squawked, holding up a garter belt and fishnet stockings. The girls clapped in glee as they grabbed the lingerie. Karly quickly wrapped the garter around my waist, clipping it behind my back as Regina rolled up the stockings in her hands, ordering me to sit down and lift my legs up.
Karly and Regina both began rolling the stockings up over my legs, pulling at the suspender straps and clipping them in place to hold up the fishnets. I began to feel dizzy from the sweet aroma of their perfume and hairspray, beginning to enter a daze as the room became fuzzy.
Jessica grabbed my arm and pulled me off the bed, guiding me towards the stool by her vanity mirror. Karla and Regina both grabbed some items from her dresser, applying different lotions and powders to my face. As I sat staring into the mirror, the room began to sway. I felt somehow entranced by the beauty of what I was wearing, feeling myself slowly being transformed.
No longer did I feel masculine or in control. I closed my eyes as they continued to touch my face with tiny brushes, rubbing them over my cheeks, applying soft moistures onto my eyes and around my lips. Several minutes passed by as I enjoyed the therapeutic experience of being pampered by all the soft and feminine hands.
I felt a velvety soft sensation as they slipped a wig over my head, gently brushing the hair as Karly whispered in my ear. "Open your eyes." As I slowly opened them, I saw a reflection that startled me, a similar but much softer version of myself just stared back in the mirror.
They giggled and laughed amongst themselves as I sat staring into the mirror, my mouth a gaze.
"He looks so girly," Karly exclaimed.
"Oh my god, he does, doesn't he!" Jessica laughed.
"You mean SHE don't you!" Regina said, bursting into a fit of giggles. "Let's get her dressed."
Karly and Regina pulled me up off the stool, spinning me round and making me feel woozy as Jessica fumbled through some dresses in her wardrobe, showing the girls several choices.
"Oh, that one, that one!" yelled Karly, pointing out a provocative pink and black cutout mini dress. "She'll look so slutty in that!"
Jessica handed the dress to Karly who helped me step into it as Regina held onto me. The two of them stretched the tight Lycra material over my hips and around my chest, fastening the halterneck behind me.
"Heels!" Regina shrieked.
Jessica rummaged around under the bed, looking for a strappy pair of 4-inch pump heels, placing them in front of me as the girls helped me slip my toes into them, supporting me as they fastened the straps around my ankles.
"Come on then, show us how you look," Jessica said, ushering me over to her standing mirror.
I stumbled clumsily over the mirror, feeling myself wobble in the heels, the dress clinging to my legs and squeaking as I walked. All I could hear was Regina and Karly giggling behind me as I tip toed over to the mirror.
'What the fuck?' I thought, seeing what they had done to me. I was no longer a man. In fact, I didn't think I could ever be a man again, they had completely emasculated me! My eyes blinked as flashes of light flickered over the mirror, the sound of the camera's clicking.
"What are you doing?" I asked. "Please! Stop!" I begged, finally coming back to my senses. I already felt weak and pathetic, dressed up like a girl, the last thing I needed was photographic evidence.
"Smile sissy!" Regina screamed, all three of them holding up their phones, snapping picture after picture as I wobbled around, desperately trying to flee the room, unable to move quick enough in my high heels.
I stumbled and almost fell as I raced out of the room, running tearfully back into my bedroom and locking the door behind me. I collapsed on my bed, hiding my head under the pillow, still able to hear their laughter echo through the wall.
That was the first time my sister and her friends played a prank on me.
A few weeks later, my sister had some friends over for a little party in her room. Karly and Regina were back, but there were a couple of other girls who I didn't know. I was trying to read a book in my room, but I kept getting distracted by loud laughter coming from my sister's room next door.
The noise persisted for a while until all of a sudden it went really quiet. I got up and tried to listen through the wall but all I could hear was whispering and again it went silent. Then suddenly my door slammed open as all five girls burst into my room making me jump.
"What you doing sissy?" Asked Regina.
"Nothing!" I replied, in a panic.
"We're bored." Regina whined, so we thought we could play dress up again, what do you think?"
"No way!" I replied, frantically trying to stand my ground this time.
"Oh come on, sissy, Jade and Larissa weren't here last time and they want to see it for themselves, don't you, girls?" They two girls smiled and nodded, looking me up and down.
"No, get out of my room, I'm not playing your games anymore," I shouted.
Regina stepped forward, the obvious 'Alpha' of this pack of girls. She reached into her bra, pulled out her phone and leaned in closely, showing me her screen before speaking in a low voice. "You wouldn't want more people to see this, would you?"
My face turned white with fear as she slid her thumb across the phone, flicking through all the pictures of me dressed as a girl. I bowed my head, then mumbled under my breath, "fine, whatever."
They startled me with screaming and clapping as Regina pulled me along and back into my sister's room. As we entered the room I noticed a collection of clothing all laid out on the bed. Jade and Larissa began stripping my clothes off while Jessica and Karly sorted through the items on the bed.
Regina stood nearby, holding her phone up in front of us as the girls hurried around me excitedly getting everything together. I looked up at Regina, a look of pity on my face.
"You're not taking more pictures, are you?" I asked inquisitively.
"No, I'm not," she replied, "I'm filming you this time. Jessica and Karly will be taking some pictures though!" she said, a wicked smile creeping across her face.
Larissa, a beautiful black girl with incredibly voluptuous breasts was busy stripping off my clothes, while Jade, a small skinny brunette helped her. I felt completely helpless as they tore my clothes off revealing my scrawny naked body.
"Oh look! It is cute isn't it," said Larissa, pointing at my penis. Jade just looked down and smirked.
For the next twenty minutes or so, they dressed me up in lingerie and stockings, then sat me down by the vanity mirror and applied makeup to my face. After several more minutes, they stood me up and Jade helped me into my high heels. Larissa handed me a slutty maid costume, I guess she must have bought for a Halloween party or something and made me slide it on over my head, adjusting it around my waist.
Jessica, Karly and Jade sat down to admire their work, while Regina stood in the corner still filming. Larissa whipped out her phone and took some more pictures too of me, giggling to herself.
"Aren't you a good little sissy maid!" Regina exclaimed. "Are you going to fetch us some drinks now?"
I stared back, a stupid look glued to my face as I tried to fathom what was happening to me.
"Come sissy!" Regina snapped, clicking her fingers, "chop, chop."
For the rest of the evening, I acted as their maid, serving them drinks and fetching them food as they ordered me around, making me perform tasks and follow their instructions as they ridiculed me. I felt so emasculated, performing what they referred to as my 'sissy tasks' until finally they tired of the game, letting me go back to my room.
That night I discovered something about myself as I lay curled up on my bed still dressed up like a girl. I actually liked it! The feeling of stockings on my legs and lingerie covering my body, the tight dress that clung to my ass and wrapped tightly around me, the long curly hair that flowed down by my shoulders and the makeup that accentuated my feminine features, making me feel so girly and pretty.
I liked it and I wanted more! I stayed dressed like that all night, feeling the lace material rub against the sheer stockings as I rolled around in my bed. I dreamt of all the types of clothes that women wore, the different styles and garments for various occasions. I pictured Regina, Karly, Jade and Larissa, the sexy outfits they wore and tried to picture myself as one of them, just one of the girls.
I felt a weird sensation as I trembled under the duvet, a hot feeling that emanated from my crotch, expanding around my pelvis as a wet sticky patch seeped through the lace panties and into the dress. I moaned, wriggling in my dress, feeling a slow and subtle orgasm that tingled down through my whole body.
A few months had passed and I had not seen my sister's friends in a while. It was summer and she'd been going out partying, which was fine by me as I had spent the time home alone. Sneaking into her room to borrow her clothes, practicing my own makeup techniques and learning how to walk confidently in high heels.
It was just another day for me, playing dress up and strutting around the house in a corset, garter and stocking set I had found buried at the back of my sister's dresser drawers. These were my special moments, when I could completely lose myself in the fantasy, dreaming of being a real girl.
I had become so used to my routine that I simply didn't notice Regina and some random guy staring in through my sister's window as I pranced around her room, swaying my hips and dancing to some music.
My perfect moment came crashing down at the sound of knocking on the window as I turned in horror to see Regina, holding her camera phone up and smiling at the sight of what I was doing. My knees buckled and I dropped to the floor, hoping for the ground to open up and swallow me.
"We can still see you, sissy!" Regina screamed through the glass, "come and let us in!"
I slowly picked myself up off the floor and tip toed ashamedly down the hall, my face bright red with embarrassment as I opened the door to my unexpected visitors.
"All alone then, are we?" Regina said, glancing around and making eye contact with the guy who just stood smiling from ear to ear. "I told you," she said gleefully. "Doesn't she look better in person!"
He laughed and nodded as his eyes grew wild with lust, scanning me from head to toe.
"Jessica is obviously not around then is she?" Regina asked rhetorically. "Oh well, never mind," she smirked. "I have an idea," she said, looking over at the guy. "This is my friend Carter, he's never seen a sissy in real life before. Only on video." She winked, a cheeky smile on her face.
I just stood there trembling nervously in my high heels, my hands covering the tiny bulge in my thong. Carter seemed overly curious to see what I was hiding underneath, his eyes glowing eagerly with anticipation, drooling at the sight of my stocking-clad legs.
"Aren't you going to invite us inside, sissy?" Regina asked, leaning forward and stepping inside the doorway as I nodded, moving further inside to allow them to enter, locking the door behind them. As we entered the sitting room, Regina sat down in an armchair and crossed her legs. Carter stood ominously by the door, staring at my ass as I walked past him.
"Can I go and put something else on, please?" I asked Regina, desperate to cover myself up.
"I don't think you're going to need clothes," she said, "not for what we have planned."
Carter began taking his shirt off, unbuckling his trousers and kicking his shoes off across the floor.
"What do you mean?" I asked anxiously.
"Well, you want to be a real sissy, don't you? I mean, why else would you be dressed like that!" she said, pointing amusingly at the lingerie and stockings, smiling to herself. "Sissies like you wear bras and panties. Sissies like you are made to please real men."
I turned my head to look at Carter who had stripped down to his underwear, his semi-erect cock protruding through his boxer shorts, a wild frenzied look in his eyes.
Regina slid her hand between her legs and started rubbing her crotch gently with her fingers, wrapping her hair around her fingertips and nibbling at the strands between her teeth. Carter slowly moved closer, grabbing hold of my hips and pulling me off balance as he thrust himself forward from behind.
"I want to see it," he said.
"What do you want to see?" I asked, the sound of my voice quivering.
"I want to see your cute little cock!" he said, pulling my thong down between my thighs and peering over my shoulders to see.
I tried to cover it up quickly, noticing Regina's eyes lighting up.
Carter's cock stiffened under his boxer shorts, pressing up against my bare ass and poking into me. I could feel how excited he was, how hard he had become because of me and felt a little tingle of my own.
"She likes it, don't you, sissy," Regina said, shooting a glance down at my tiny stiff cock.
Carter pulled my thong down further between my legs and pushed me forward, making me trip and fall face forward onto the sofa. My body bent over the arm of the couch, bending my ass upwards in the air as he quickly ripped his underwear off and positioned himself behind me.
"Wait! I'm not sure about this!" I tried to call out, the inaudible sound muffled by the sofa cushions pressing against my face.
Carter bent down, frantically running his wet tongue around my pink hole, burying his tongue into me and passionately licking me, covering me in saliva.
My whole body relaxed as I let out a loud but muffled moan. For the next few minutes, I laid, face down, moaning with pleasure as Carter ran his tongue around and inside my gaping hole. I had never experienced sexual bliss like it in my life. The world around me melted away as I lay there, legs spread, enjoying his oral pleasure.
In the background, I could hear some occasional whimpering moans coming from the other side of the room as Regina began to enjoy herself watching. Carter had stopped briefly and I could hear him shuffling behind me. As I slowly lifted my head, turning to see what he was doing, I felt something hard enter me.
My eyes widened and my jaw dropped as I gasped for air, letting out a feeble whimper. I knew exactly what was happening now. Carter's hard cock was inside my ass!
"Oh fuck, fuck!" I groaned, feeling him slowly slide inside me, my ass tightening around the head of his cock as he pushed deeper inside me. Whatever reservations I may have had about letting a guy fuck me was gone. It was too late to think about that now.
Carter moaned loudly behind me, pulling me closer as he rammed his hips against my cheeks, stretching my ass open with his stiff cock. I stuffed my head back down into the cushions, whimpering as he began fucking me faster, feeling a strange but good sensation as he slid back and forth into my ass.
His fingers clung to the sides of my corset and I could feel my heels swinging in the air, slapping together as my body bounced off the couch.
"YES! Oh, fuck yes!" Carter groaned, loudly emptying his balls and filling my ass with his hot come.
He swiftly lifted himself off the couch leaving me lying slumped and exhausted on the couch.
"Did you get it?" he asked, looking over at Regina who was holding her phone up with her spare hand.
"Oh yes, I caught the whole thing!" She smiled nastily.
Without another word, Regina adjusted herself whilst Carter finished dressing, then got up as they both headed for the door. Just as they were leaving, she stopped turned and said one last thing.
"Well, that was fun wasn't it, sissy? Next time will be even better!"
