tagTranssexuals & CrossdressersLittle Red Riding hood

Little Red Riding hood


I met Conrad in a pub around the corner from work in the city. We exchanged a few glances and smiles then just hit it off. We never planed to meet but he was always there when I popped in for a drink with the lads after work. He was an artist. I got to meet his friends and it wasn't long before he had my number and invited me to one of his art exhibitions. I was somewhat in awe. I admired his work, his style, his lifestyle and his friends. I hadn't a gay bone in my body but there was something about this guy I found suave. If I was a girl, I mused, Conrad is the type of guy I'd date. We became good mates and spent some considerable time together. Yet I didn't really know him. I didn't know his background, his family or anything about his life before moving to London. I had no idea of his sexual orientation or what a wicked guy he really was and therefore wasn't at all afraid of him.

The company in which I worked wasn't holding a Christmas party this year due to poor trading performance. I was therefore insanely jealous of all the Christmas activity being planned.

'I wonder if you would do me the honour of coming to my Christmas bash.' Conrad asked.

'I'd love to!' I gush.

Predictably Conrad proposed something a little unusual. A themed fancy dress, held at his favourite club. The theme, fairy-tale characters causes a stir amongst his friends. They all immediately discussed who they were going as. Hansel and Gretel, A match seller, Rapunzel, Thumbelina, a frog.

I unlike the others had no idea what to go as. The excitement shattered when Conrad announced there was to be no duplicates. He didn't want fifty gingerbread men or fifty witches so he devised a plan to ensure he got his way. His close friend and very attractive pa, Kate typed up every fairy-tale character she knew and printed them on tiny strips of coloured paper. Blue for boys and pink for girls. Folded she placed them in two hats. We then all draw a character and to retain some surprise were not to tell anyone who we picked. Kate gleefully handed me a tiny folded piece of blue paper.

'I have no idea, what this is,' she says.

'Who are you?' I ask forgetting the Conrad party rule.

'Can't say,' she said with a smile as I opened my slip of paper with trepidation.

There neatly typed in black and white

Were the words "Little Red Riding Hood?"

I groan noisily thinking there must be a mistake.

Kate laughed. 'I don't think anyone is happy with their choice but you never are, are you?'

I agree but begin to regret accepting the party invite. The thought of wearing a skirt and showing my legs didn't appeal. I contemplate an excuse but Kate seems to read my mind. 'Conrad's absolutely delighted that you're coming,' she chimes. 'Look, if you have any difficulty in getting a costume I recommend this company.' She scribbled the web address of a fancy-dress store on the back of my hand.

I delay making a costume decision in the vain hope that Conrad may change his mind and hold a conventional party - no such luck.

With no alternative and little time I visited the site that Kate suggested. Sure enough they had a 'Little Miss Riding Hood' costume. It was obviously designed for a young sexy girl with a short dainty dress and a bright red hooded cloak. The attention to detail was incredible as I was able to order a long curly blonde wig, tights and a wicker basket for added authenticity.

It was as simple as buying my groceries on-line and without any of the expected embarrassment. A few days later the large box turned up at my flat. I thought it wise to have a dress rehearsal in case it didn't fit or they had sent the wrong one.

Everything looked perfect and to my surprise they had supplied even more than ordered. My box contained the dress and the fabled little riding hood of red velvet but also make-up, shoes, wig matching red silk panties and a bra with matching stockings and suspenders.

It probably wasn't necessary to wear everything but now that I had made the decision to go I was determined to look the part and impress Conrad. I made up my mind that if I looked really ridiculous I wouldn't go.

I drew my curtains and laid everything carefully on my bed. While I gazed down at all the feminine things I took the monumental decision to really go for it. The picture on the box showed a pretty young girl with soft skin, dramatic make-up with ruby red kiss-me lips. Her pert boobs positively overflowed from her costume and she held a pose that looked more prostitute than innocent young girl. That day something strange happened. Conrad and his themed party had awoken a passion deep within me that was as scary as the suave wolf also in the picture. Staring at the colour images I felt myself absorbed into the print as if looking at myself. I wanted to be her, to dress like her, to kiss like her, to fuck like her. Becoming increasingly aroused I took a hot bath and shaved myself all over. An hour later I step back into the bedroom with skin as soft and smooth and a cock like iron.

I felt an attraction to the dress so strong I don't think I could have refused to wear it even if i wanted too. My heart racing and hands trembling I slipped the padded bra on first, clipping it round my tummy, twisting it around my torso and slipping my hands through the shoulder straps. I performed the operation as if I'd done it many times before. It fitted. This is child's play I mused. Next, I stepped into the short red satin dress with its white built in Basque and sumptuous red bows. When I drew the whisper light fabric up my legs my cock began to quiver. I tried to ignore its throb but I couldn't hide how turned on I had become. Again it fitted. I wrapped the black corset round my waist and pulled in the red laces. It wasn't easy but I held my breath and pulled some more, transforming my waist into a classic hourglass. With sparkling eyes I glanced down at my womanly shape having never appreciated my narrow waist and long legs before. I tied the frilly apron round my waist and draped the short hooded cape over my shoulders and fastened it round the neck.

I felt like a princess but didn't want to peek at my reflection until I was done. So with no further-ado I sat on the bed and leg by leg rolled the white sheer stockings up my legs. The moment freshly shaved soft skin touched Lycra I melt like butter left in the sun. My heart began to pound and my cock throb and swell as if on Viagra. I could hardly contain myself as I hold my skirt aloft and wrapped the suspender belt round my waist and clipped the straps onto my stockings. The soft tug of the dainty ribbon caused my cock to dribble and I dropped too my knees and grasped it hungrily. Like many, I regularly toss myself off during the sparse girlfriend moments such as these but this time it was different. It was different for two reasons; one I just had to wrap my hot fingers round my tool and I began to prematurely eject all over the carpet. And furthermore as I did so I filled my head with a series of incredible visions. Not bare naked ladies from some soft porn magazine as per normal but of a man with a huge cock making love to a beautiful women in a striking red dress with a hooded red velvet cloak and quite clearly that girl was me. Rather than be repulsed I loved the dream and the visions stayed with me as I pumped myself dry imagining coming with a thick cock inside me.

Mildly mystified I cleaned myself up expecting to be off put by my reaction but instead I wanted more. Keen to improve my transformation I stepped into the net petticoat and drew it up my legs the stiff netting tickling my smooth legs as I positioned it carefully under my filmy skirt. It cast a magical effect upon me and caused my skirt to stick horizontally outward magnifying my hourglass figure. Amazed I shook my hips and watched the whole dress shimmy and sparkle in the light. I stepped into the super-sexy patent misty-red Mary Jane shoes, with pointy toes and adjustable straps. They too were a perfect fit and I struggle to balance forgetting I wasn't wearing any underwear. I giggle foolishly and pick the skimpy panties off my bed. I pause before stepping into them. Was I going too far? Did Conrad or Katie really expect this - Whatever - I didn't care. My outfit suited me so well I decided not to wear anything else. Everyone will know who I am I thought they will all call me 'Little Red Riding Hood.'

Then it happens for the second time. The soft silky caress of the panties are just too much and I ejaculate yet again but this time I soil my new fresh panties. I moan and squirm as my excitement soaks into the satin and lace. But unlike before as the damage is done I don't bother to clean myself up but drop the stunning wig over my head. It's heavy but the beautiful shoulder length curls with red ribbons and tiny pigtails frame my face like a picture. Immediately as the soft curls soften and transform my face I feel like sexy vamp, Marilyn Monroe not coy Miss Red Riding Hood.

You real girls know why but trussed up in my tiny dress, bra and panties with sexy stockings and my 'fuck-me' high heels I was compelled to dance so I did. I grabbed my ipod and pranced about the room dancing the best I could. As I spiralled across the room, my heels clicking on the wooden floor I danced like I'd never danced Before. It was then I first caught a glimpse of my reflection in my mirror. I was truly beautiful. I had to stop and stare to fully take in my transformation. I was beautiful. This was a classy outfit guaranteed to provide some festive frolics. I just couldn't take my eyes off myself as I practice routines as if a support dancer for the Spice Girls comeback tour. As I spin blissfully around the room I notice that the slightest movement sent my dress swaying skywards and saw for the first time why they supply matching red panties. I laugh aloud flicking my hips to best effect and conclude if really a girl I would be a dirty tart happy to flaunt my assets and drop my knickers to any big cocked man. In a kinky world of my own I must have shimmied for a good twenty minutes before I collapsed on the sofa exhausted. But still I maintained my decency and crossed my legs careful not to show any more panties despite my sluttish intentions.

All the excitement had taken its toll. I was tired and I soon feel asleep in my sexy Little Red Riding Hood outfit. That night, while slumbering, I had an amazing dream. I was born a glamourous girl and lived and worked in the most sumptuous dresses and sexy lingerie. I was a popular girl preferring to lie on my back or perch on my knees. I was a guys dream. I loved having my cute breasts caressed and sucked, my nipples played with and my skin stroked. I gave the best head ever. My bright red rosebud lips framed a hot sexy mouth and my tongue knew how to wash slavishly the dirtiest of cocks. I loved sex anywhere, anyhow I tried anything out.

I woke at eight o'clock not by my bedside alarm, but by the early morning traffic roaring past my lounge window. I jump up startled somehow knowing I was late. I stumble ungainly in my sexy high heels, almost laddering a precious stocking. I must have looked a picture. I would have laughed but late for work I was in a mad panic. I tore off my costume and hurriedly dressed grateful for not wearing make-up. I then did a daring thing. I couldn't part with all my feminine attire so I left my dirty panties on under my trousers. I had to wash them anyway but their constant silken caress on my crutch was a naughty reminder of my sexy outfit that waited for me at home.

That day I worked in a dream. The silk panties sending sparks of joy through me with every slight movement. I worked while walking as if on air. My outfit had ignited a strange desire in me that I wanted to explore. Every girl I met, I eyed differently. I studied what they had on and wondered what it was like to wear and then I wondered what panties they wore and how their boyfriends tore them off and fucked them. More alarmingly I imagined I was a girl and wanted to be fucked.

On the day of the party I asked the local beauty saloon if they could help. They booked me an appointment and at the end of the day I found myself telling a gorgeous tall blonde in a fresh white coat all about Conrad's strange themed fancy-dress party. I explained that I was to be Little Red Riding Hood and after a brief snigger I was stripped, waxed and moisturised. She plucked my eyebrows, stuck painted false nails on my fingers, waxed my legs and chest, trimmed my pupes (yes I know!) and made up my face into a radiant girl with the artful use of make-up.

An hour later I skipped back to my flat with a tiny bag of make-up and a pink lipsticked smile so wide you'd think my face would split. The other passengers on the bus gave me odd glances but I didn't care as tonight I was going to be a pretty girl and nobody was going to spoil it for me.

With only a few hours to spare I went straight home and excitedly slipped back into my dress and cloak careful not to smudge my new make-up.

At last I was ready. My heart pound like a bass drum and my manicured hands shook nervously as if going on a first date. My cock starts to swell and I was in danger of showing too much. So like the other night I let my panties fall crumbled to my ankles and sat on the edge of the sofa. I gazed dreamily at my cute reflection, my cock only just firm. I couldn't take any chances. Having wanked every day since becoming Little Red Riding Hood, sometimes morn, noon and night I felt sore as I gently pulled myself off careful not to mark my pretty new clothes.

It didn't take long and drained of masculine love juice I felt ready.

Just before I left and knowing Conrad's eye for detail I put a piece of cherry cake and a bottle of wine in my wicker basket for my sick grandmother just to adhere to the fairy-tale.

The party was in North London a short tube journey and a ten minute walk from my flat. I could have caught a cab but my make-up stopped traffic and my long slender legs turned heads. It wasn't everyday I dressed as a girl, looked this good and felt so confident. Proud of my transformation I wanted everyone to see. Besides it wasn't so hard, being so close too Christmas the streets were full of party revellers, many of whom were in fancy-dress too or with flashing Santa hats so I skipped merrily down the road almost unnoticed.

The party was heaving when I arrived and just as Kate had planned the floor was completely full of different fairy-tale characters. I felt nervous as i stepped inside. The walls where adorned with holly, ivy and tinsel, the ceiling was covered with Christmas decorations. There was a fuchsia shimmer curtain behind the decks, and a huge rotating / flashing disco ball just above the DJ. I could just make out a large Christmas tree far away on a stage covered in coloured bulbuls. Podium girls dressed as Miss Santa in tantalising short red dresses, black fishnets and fur topped black boots entertained the crowd.

'And you my gorgeous must be Little Red Ridding Hood?'

I puckered my lips and fluttered my long eyelids and showed the burly doorman my ticket as I swaggered cautiously inside. Immediately I saw a witch, a mermaid, a frog, a prince and even a princess. They were all bopping away in an array of Christmas headgear shouting along to the music. No question - I was in the right place. In a weird way, I felt as if the characters were real, living people. it was as if, for this night, the fairy-tale characters had come magically to life. Like me they too had become who they dressed as.

Some handsome guy wearing a woodcutters outfit carrying a plastic axe immediately approached and bought me a cocktail. A little spark of excitement shot through me. I thanked him for the drink as he chatted me up with a few cheesey lines. I giggled girlishly and tossed my hair flirtatiously. I mumble something about the night and he hung on my every word. Flattered? Yes, available? No. I wanted to play the field but it was a promising start. And why wasn't I looking at the beautiful women? The place had plenty of them. I just wasn't interested. Dressed as I was they where competition not prospects.

The electro music was loud and funky, the lights dim and everyone was either drinking or dancing passionately. Everyone looked half pissed, many where drenched in sweat and there was much canoodling and naked flesh. The atmosphere was electric. I just couldn't resist swaying to the music as I hung round the edge of the club admiring the good looking crowd. I look for Conrad or any of his friends but I soon found myself joining in with the strangers, swinging my hips like a true club dancer, prancing round my wicker basket and tossing my hair sexily just like the other night. at home I was a bitch on heat and I danced for sex my mind awash with the thought of cock. Until a few minutes ago, I'd been tempted to bolt from the club. but now, amazingly enough, my nervousness had gone.

I felt hot but the cool air-conditioned air wafting up my light skirts kept my cock neatly tucked away as I danced - but unlike the other night today I had an audience, a hundred pairs of eyes scanned me like a Xerox. Despite the competition of dazzling princesses and dramatic queens I was attracting loads of looks and received countless compliments. I became so immersed in my character I completely forgot who I really was and why shouldn't i? I looked incredible and felt the night was mine.Girls admired my dress and shoes whilst boys thought I moved with rhythm and my body was hot, blissfully unaware of my true identity. Did I tell them? Shit no. I revelled in the limelight, lapping up the compliments like a thirsty hound. If they wanted to get inside my knickers I wasn't going to stop them. It's not everyday a lion pinches your bottom, a frog catches a grope or Thumbalina flashes a seductive wink and holds hands to dance with pure sexual energy. We attract an eager crowd as Thumbalina and we dance, wrapping our limbs together and swinging our hips to the beat. Soon Conrad's attention is drawn to the commotion.

He's dressed as the big bad wolf in an incredible hairy wolfs costume with large paws, long swishy tail and snarling fang mask.

'You look amazing,' he gushes in a big voice as I spin before him my hands high in the air, shaking my big boobs.

'You too,' I say admiring his ears and muzzle.

'Yeah cool isn't? I used to be a wolf but I'm all right now...howl.'

We both laugh and he gives me an affectionate hug.

'What have you got in your basket?' he asks

'Cake and wine,' I say pleased that he had asked and hoped he too was impressed with my attention to detail.

'Yesterday was baking-day - its for my poor sick grandmother to have something good, to make her stronger.' I add remembering the tale.

He beams obviously impressed.

'Have you seen her tonight?'

'Who?' I shout struggling to make myself heard over the music.

'Your Grandmother,' he grins.

'No' I reply, 'not yet, I've not been here long.'

Conrad laughs. 'She is here somewhere. It's Kate don't you know.'

I look confused.

'Yes, our Kate's dressed as your sweet old Grandmother and looks incredible as you'd expect. By some quirky fate you, Kate and I are all from the same fairy-tale.' Again he grins and for added wolf realism he paws the air and bares his sharp fangs. 'You need to find her to give her your cake and wine...' he pauses as if waiting for me to catch up. 'To make her feel better.'

I smirk.

'Isn't that how the story goes?

I hadn't forgotten.

'Where do you think your grandmother is, little Red Riding Hood? He asked looking through the throbbing crowd.

I wasn't sure. 'Somewhere on the dance floor I guess,' I say really getting into my role. 'Centre of attention I bet, near the Christmas tree.'

Report Story

byTomsparty© 3 comments/ 77331 views/ 24 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: