Explore the Inner Woman In You

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Get girl advice, but watch out!
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Tomsparty
Tomsparty
645 Followers

I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My dizzy ambition was to ask her to the end of year college dance. My fiends all laughed but I felt I had as much chance as them even though I was rather slight and effeminate looking. To my surprise one lunchtime in the refectory at college, Bob, her older brother came up to me. He was a few years above me doing new media and photography with my older brother. I didn't really know him but to my surprise he asked me if I fancied my sister. I blushed and he knew the answer before I could reply.

'Good on you,' he said, 'perhaps I can help you.'

Why I wasn't sure but I nevertheless I was delighted and didn't stop to consider why.

'Come round to our house, Saturday and I'll give you a few pointers. I can read her like a book and know how I can help.' He could see the concern in my eye. 'Don't worry Sharon is out for the day.'

I couldn't believe my luck and call it naivety but I didn't see anything wrong or sinister about his offer.

However once inside his empty house I began to feel rather awkward. He offered me a beer and looked at me rather strangely.

'Sharon's a funny girl - she likes to meet guys that are kind and understanding,' he told me. 'She's not the kind that likes insensitive thugs. You have to think how a woman thinks to understand her.' He laughs. 'She's a strange one - but get to that point and she'll eat out of your hand.'

I feel my mouth drop in awe. 'But how do I do that?' I asked.'

He smiled confidently and gestured that I sit down. I choose a comfy chair by the window. 'You'll thank me,' he chuckled, 'but what I'm going to suggest might sound rather unorthodox.'

'What is it?' I asked eagerly.

'Ok,' he said, 'but you must promise not to tell anyone else ...' he paused then added. 'It's all a bit embarrassing.' I nod frantically desperate to know his sensitive secret.

'To think like a woman,' he said slowly, 'you have to be one and without surgery the only way you can do that is too dress as one.'

'What!' I cry. 'Dress as a woman? You can't be serious.'

'Oh yes,' he said. 'I'm afraid so. I couldn't believe the advice either but the older brother of the girl I fancied a few years ago said the very same thing. And like you I didn't believe him either.' He laughs and smiles reassuringly. 'I genuinely thought he was mucking me about but... after some persuasion I did what he suggested.'

'What!' I interrupted. 'Wore a skirt?'

Bob blushed. 'More than a skirt,' he said, 'I told you this was a humiliating confession. I wore the whole outfit. Lingerie, shoes and a dress.' He gazed at me dreamily and I felt a shudder cascade down my back.

'And it worked?' I said. 'Really worked?'

Bob took a deep breath. 'Did it work? Absolutely. Absurd I know but the clothes he lent me changed my view on her and women generally and I really connected with her. After that I had to fight to keep her back.'

'Wow!' I say totally believing him. 'But I haven't a sympathetic sister or anyone who could help me.'

'Well,' Bob said pouring me another beer. 'You're in luck - I can help you. While you're here why don't you borrow something from Sharons wardrobe. She's out and won't be back until early evening.'

I wasn't sure but the more I thought about it I couldn't resist this opportunity.

'It's now or never,' Bob said. 'I'm not going to suggest this again.'

'What?' I say. 'Borrow and take away?' Thinking this isn't too bad as I wasn't so sure about Bob seeing me dressed as a girl.

'Bob laughed. 'No I couldn't do that. Sharon would notice if anything is missing. I was thinking more about you changing here.'

'Oh!' I said.

Why I agreed to this I will never know but after yet another beer I found myself rather inebriated and obediently following him upstairs. We crossed the landing past his bedroom and into Sharons. It was amazing. As I walked inside I could sense her presence. I could smell her sweet perfume, almost hear her laugh and see her sweet smile. Her room was just as I had imagined – very feminine – decorated in light pinks with a flowery bedspread, pop posters on the wall and loads of bottles of perfume, jewellery and make-up on every conceivable shelf. It was breathtaking and I wondered how jealous all my mates would be if they could see me in Sharons bedroom. I crossed her room and looked dreamily at her bed and soft toy collection.

To my surprise Bob pulled a box off her wardrobe. 'Girls,' he said, 'as you no doubt know... love lingerie. All the frilly and lacy stuff drives them wild and our Sharon is no exception.' He holds the box like a precious casket containing priceless jewels and taps its lid with his fingers. 'This in here is her favourite and I suggest you wear it first.' He lifted the lid majestically and withdrew a beautiful boned corset in a black beaded metallic looking lace.

'B... B... But that's a corset,' I stammer. Is this really necessary?'

Bobs face turned serious. 'Absolutely, Its important that you love what she loves, to feel what she feels and to look like her look.'

I wasn't so sure but Bob practically tore it out of the box, and he practically tore off my clothes, too, except for my pants. This all came as rather a shock but I felt reluctant to complain as after all he was helping me... Or so I thought. The first thing that surprised me was how unbelievably good he was at getting it on. I thought the padding he stuffed in the cups a bit unnecessary but he seemed possessed – I could tell its really not that easy – and then he started pulling the laces at the back tighter and tighter. More and more roughly. I saw him in a new light. I never thought he was so rough; obviously I was wrong.

'Please, stop!' I gasped, almost fainting, but he just sort of threw me across Sharons huge dressing table, so all her perfume bottles and stuff crashed to the floor, sending up wafts of floral fragrances.

Eventually he tied the last lace and panted with exhaustion. I could hardly breath and as I staggered to my feet Bob threw open Sharons wardrobe and began flicking through the huge assortment of dresses. I began to feel rather uncomfortable as I struggled to breath.

'What do you think?' He pants excitedly. 'Dress or skirt, Stockings or tights, sling backs or court shoes?'

I had no idea but my uncertainty seemed to please him.

'While I'm finding you something,' he said with huge excitement, 'open her top draw in that chest and choose yourself some panties.' I look at him in disbelief. He laughs 'trust me,' he said. 'It's all or nothing.'

Had the circumstances been different I would have loved delving my inquisitive hands into her pantie draw. It was like Pandora's box but dressed in her corset with Bob her brother I felt very out of place. Needless to say she had hundreds of pretty panties in an amazing assortment of colours and styles; jade coloured bikini briefs, black high-sided panties, cream thongs, red cami-knickers, chocolate satin mini briefs, white underwired bodies and peach G-Strings. I felt like a starving man with a menu and I drifted into a trance as I imagined her parading in front of me wearing them all. My dream was shattered as I heard Bob clear his throat and I turned crimson as I hurriedly choose a beautiful pair of tiny white silk panties adorned with a pretty bow just above the crutch and lashings of lace.

'Good choice,' Bob said as he watched me step gingerly into the silky cool fabric. They where incredibly tight and once I'd stretched them in place the delicate lace trim tickled my legs and my little cock was squashed into a feminine mound. I looked at him nervously as he produced a black and pink lace dress from her wardrobe. The bodice looked very small but the skirt was quite full and feminine. 'Perfect.' He cried. 'And while you're at her chest of draws try the second draw down and get yourself some black stockings to go with this.' He tore the dress off the hanger and threw it to me. 'Come on,' he cried 'Don't stop the momentum - lets see you fully dressed?' I apprehensively sat on her soft bed and rolled a pair of sheer stockings up my smooth legs. To my surprise they felt unbelievably gorgeous and I couldn't resist running my hands up and down my calves revelling in the sensual sensations. Nice I thought as I stood, straightened the seams and clipped the lacy tops delicately to the suspender straps of the corset. Something extraordinary then happened – my legs looked much longer, shiny and incredibly smooth in fact and as I rubbed them together I felt very delicate, pretty and feminine. Perhaps this is what he meant I mused as I stepped into the beautiful pink and black dress. It was as I thought, tight and even though lined with a silk slip I had to waggle my hips to get it up not realising the show I must have put on for Bob. As I slipped my slender arms into the sleeves I noticed him grin and as I did so I couldn't help but see with horror how Bobs trousers had begun to bulge at the crutch. He saw me look and I pretended not to notice. Bob grinned and walked towards me. 'You're quite a stunner,' he said gesturing for me to face away from him. He gently fastened my dress up at the back and as he did so he accidentally nudged his groin into the pit of my back and I felt his rock hard cock through the soft thin dress. I tried to pull away but he held me by the shoulders as he rubbed himself against the lace. I felt myself glow red but he was right I began to feel an inner change. I did feel feminine. Bob too saw the transition as he handed me a pair of black, incredibly high-heeled shoes. 'How are you feeling?' he asked. 'How's your inner woman? Can you sympathise with her yet?' I thought carefully as I stepped into each towering shoe. Then nodded nervously. He smiled and gestured me towards Sharons dressing table and patted the stool. I hobbled precariously across the room my hips swinging from side to side and my arms held slightly aloft. The dress made a delightful swishing sound and my nylon covered legs rasped and my heels clicked on her wooden flooring. Bob was right I did feel remarkably different. And rather than be repulsed with what I was wearing I began to enjoy every minute and looked forward to the next element of my feminine transition. I sat down, crossed my legs and adjusted my dress as if perfectly natural.

'Try adding some colour to you face, Sharon' he said.

'Sorry,' I said, 'surprised that he had called me Sharon.

'Names are so important,' he said, 'I can hardly call you by your real name dressed as you are. Besides you're supposed to be Sharon so it's only fitting that I call you Sharon. Isn't it?'

I nod and stared dumbfounded at my reflection in the dressing table mirror. Even without make-up and my masculine haircut I looked incredibly like a girl. I gazed at my full lips, glowing complexion, bright eyes and smooth skin. I felt my cock stiffen in my panties and felt close to exploding in the silk as I applied some bright red lipstick, mascara and eye shadow. The next time I saw my reflection I was Sharon. Overjoyed with the result I looked on the dressing table for what else I could do. I found a dainty bracelet and necklace set and slipped it on one wrist and a dress watch on the other. I clipped some earrings on my ears as well as a large ring on my finger. The next most obvious thing was nail varnish and Bob just watched transfixed as I opened a tiny side draw and found a polish that matched my lipstick. I couldn't believe how easy it was to apply and as I painted the final coat on a little finger Bob wrapped the tiny matching necklace around my neck. 'Thanks,' I said. 'I feel really special now.'

'Good, good ,good,' he said, 'this is helping then?'

'I'm not sure.' I said, 'It's fun but it all seems rather extreme. Are you sure this is all necessary.'

He laughed and rubbed his hands together gleefully. 'I don't know what your worried about, you look amazing. A real beauty - you put my sister to shame.'

Suddenly I had to see the funny side of it. 'Ooh, you're so naughty,' I purred trying to get into the spirit. But then suddenly his laughter grew rather menacing. 'You haven't seen anything yet, believe me, Sharon' he said. His voice and laughter became louder. 'And now there is nothing to stop you truly believing that you're a young pretty lady!' he roared, and threw back his head in crazed triumph.

More concerning was how I enjoyed wearing her clothes. This worried me a lot and I calmed my fears by thinking it was because I could smell Sharon but I did wonder if it was the clothes themselves that where turning me on.

'I still fell rather odd,' I said.

'That's quite natural,' Bob said in a matter of fact way. 'You're a young man and your full of young mans excitement.' He smirks and rubs his own huge bulging cock. I look at him awkwardly. 'I'm not sure what you mean,' I said.

'Don't get me to draw a picture,' he laughed. 'You need to relieve yourself. Then with empty testosterone tanks you should be able to fully emphasis.'

'And you did this too?' I ask slightly horrified. He nodded. So that's how a few minutes later I found myself in their family bathroom on my stocking covered knees with Sharons lacy panties around my ankles, my skirts up round my waist and my little cock in my hand. Bob didn't have any girly magazines so he suggested I look through Sharons mail order catalogue. I did. I'd never looked through a girl's clothes catalogue before but dressed like one of the pretty models on the glossy pages it seemed quite acceptable.

I spent a few minutes looking at the day wear then the evening wear and progressed to the lingerie but strangely rather than thinking of Sharon in a lustful man way I began to dream of wearing the other items in the catalogue. As I scanned the pages my cock began to throb and I became really turned on. I began to forget where I was, who I was and what I was doing and began to moan. I was delightfully happy. I shut my eyes. I was in heaven as faster and faster I pumped and as the bathroom door creaked opened and I pumped frantically I shot my sticky load and sprayed the toilet wall with my creamy cum. Mortified I turned round, amazed that Bob had the nerve to enter the bathroom. It wasn't Bob. To my surprise there framed within the doorway was my Sharon dressed in high heels and an incredibly short mini dress. Behind her stood Bob with a huge grin on his face. Sharon looked horrified.

'What on earth is going on here? Why are you... in my clothes and Oh my god! What have you done? That's disgusting. Where's Mum and Dad?'

Bob tried to look eagerly horrified. 'I don't believe it,' he cried. 'The pervert came round to see you and asked to use the toilet. I've been downstairs playing CDs. I thought he was a long time.

Sharon gazed at me intently. 'That's my dress, those are my shoes, that's my jewellery, my make-up and I bet those are my stockings.'

Bob smirks. 'I bet he's wearing your favourite corset too,' He adds with an evil grin.

I glare at him, struggle to stand, brush the dress down and pulled my panties up. Sharon points at her lacy panties as I adjust them under the skirt. She was speechless.

'I can explain,' I said and looked past her to Bob who was biting his tongue to stop himself laughing. 'I know this looks strange,' I said, 'but there is a logical explanation.'

'I don't want to hear it.' She screams. 'You cannot possibly justify wearing my clothes and jerking yourself off.' She smacked her head with her hand. 'This is just unbelievable. I don't think I can stand it. Look I'm going to Lindas and I'll be back in 60 minutes. Just make sure you've cleaned up. Put everything away and are gone by the time I get back.' She then spun on her heels and stormed out glancing back at Bob... and I hold you partially responsible so get this sissy out of my house.'

Once the front door had slammed shut I glared at Bob. 'That's fucking great,' I scream skipping back into Sharons bedroom. 'Thanks for your support. You could have saved me from this humiliating death. I've got no chance with Sharon now. She thinks I'm a sissy who gets off by wanking in her ladies clothes.'

Bob laughs. 'Why should I? I always knew you where not good enough for my sister and I had to do something.' He laughed and put a comforting hand on my shoulder and stroked the thin material of my dress. And I think I've done that very successfully don't you think?'

I was furious. 'Give me back my clothes and get out,' I scream but he didn't budge instead he walked around me his hands wandering over my buttocks. 'Get off!' I shout. Then it happens he pushed me back over the dressing table his hands roughly clawing at my skirt.

'Stop pretending to be shocked, pretty Sharon. I know your sort you loved every minute. I could tell the moment I laced you into this tight corset. Look at you - the feel of the lingerie against your smooth skin and this beautiful dress tickling your long slender legs. You're in heaven and you wish you'd done this before. Just be truthful to yourself. Relax and enjoy.'

'I'm not relaxed, I'm not enjoying myself and you've humiliated me beyond believe.' I scream.

Now I think he knew this was a bit of a lie but I wasn't going to confess my true feelings and I had no idea what his intentions where but I needn't have worried as he soon made these very clear as he began to slide my dress up my legs and over my round arse cheeks.

'Show me those panties again, Sharon and lets see your sexy corset,' he gasps. 'I'm hot for it! You cant dress up all provocatively and not expect to give something in return.'

'No, no!' I shout, 'Stop it!' but his great weight and superior strength rendered me powerless as he had torn my panties once again down my legs. My eyes watered as he kicked my legs apart so I was laid spread eagled across the table. I then heard the unmistakable zip of his fly then felt his large cock pressed against my hole. I opened my mouth to cry but all I could utter was a squeal that sounded like an excited schoolgirl. Then as I tried to capture my breath I felt him slide his huge throbbing cock inside me. Inch by inch he slides into me stretching my hole to a size it had never stretched before.

'Are you a pretty virgin?' he shrieks as I gasp, moan and involuntarily push back into his throbbing cock. 'Never been kissed? I can't believe that but I do think you're a virgin. You're lovely and tight and your cherry has never been popped. I am your first aren't I?' He laughed lent backwards and grasped my fleshy buttocks and played with my suspender straps until finally slapping my backside with his hand. Slap, Slap, Slap. 'I want to hear how much you want me. Say it!' Slap, slap, slap. 'Say fuck me! Nice and loud,'

Strangely I couldn't resist. 'Fuck me, fuck me, fuck me,' I scream but then I add. 'I want to have you cum inside me.'

'Oh! Sharon, that's a good girl, you are a sissy whore but help me as I can't decide,' he cry's, 'whether you're more stupid and cullable or more of a sissy than I originally thought.'

But I couldn't reply as he began to rock back and forth with increasing rhythm his jeans slapping my bare bottom. Back and forth he thrust faster and faster until I felt him spasm and with one mighty thrust his cock twitched and I felt his hot cum shoot deep inside of me. I gasp and feel utterly exhausted as he pulls out of me with a resounding plop. He slaps me hard on the butt once again. 'Nice ride,' he shouts you are more of a sexy woman than I thought but now you'd better go before our Sharon comes back.'

'Let me go then,' I sob but something strange has happened. Though humiliated and ashamed I did enjoy his cock inside of me. Yet I wanted to scream at him, hit him and shout but I couldn't. I wanted him and needed him at least to untie me from Sharons corset. I looked at him confused. Was this what he meant with empathy. Had I found my inner woman?

Tomsparty
Tomsparty
645 Followers
12