I bet you've never met someone as insecure and jealous as my girlfriend, Trudy. She believes if I'm too desirable, every girl will want me. I'm flattered but I give her grounds for concern. I'm an outrageous flirt and know I'm popular with the ladies. Being charming comes naturally and I can't help my boyish good looks. Trudy loves me so much she does her best to spoil my fun. She makes me wear daft fashionable clothes and even cuts my hair badly - yet girls still fancy me. I just can't help my a****l magnetism. It's a gift. Things are better, she's certainly more trusting so I believed her when she tells me about Guy and Darlene's dinner party. It's a themed fancy-dress, where the boys dress as girls and the girls as boys. I thought for a moment of Trudy in my blue pinstriped suit with a crisp white shirt and tie and felt my little cock stiffen. It could be fun I muse as I find seeing her in my clothes very sexually thrilling. Then I consider Guy. 'I can't imagine him in a dress,' I say.
'I know,' Trudy chuckles, 'it will be a right giggle.
'... And he agreed,' I ask bemused.
'Yes,' she laughs. 'That's the amazing thing. Didn't you know, given half the chance boys love to wear skirts.'
'Hmm,' I say unconvinced. 'I've never worn a skirt before.'
'That's even better,' she claps. 'A skirt virgin. I'm sure you'll find the whole experience humbling.'
I wasn't sure. 'I'll look a prat.'
She saw my reluctance.
'It will be hard for me too, Honey,' she coos, 'I wouldn't normally be seen dead without make-up.'
I picture Trudy again in my work suit. 'Do you really think you can make me look OK?' I ask coming round to the idea.
'Listen, David, I should know how to make you look like a convincing girl! After all, who better to turn you into a girl but a REAL girl, right?
I nod and on the same premise look forward to dressing her in my old suit. I secretly love the idea of masquerading as a girl. I don't keep many secrets from Trudy but cross-dressing is a favorite fantasy of mine. Hmm! The idea of being dressed in delicate lingerie and a beautiful dress with high heels regularly drove me wild and this party seemed the perfect opportunity to enact my dream. It's my suppressed feminine side that gives me empathy towards the ladies and increases my popularity.
On the night of the party I rush back from work to our flat. I'd had an awful day. My boss, Mark, gave me no peace so I was looking forward to a relaxing evening. Mark can be an arrogant bully at the best of times. He talks to me like dirt and bosses me around like a skivvy. Yet he pays well and I enjoy the job sufficiently to put up with his rudeness. My annual appraisal due in two weeks and with promotion prospects likely it was essential to be as accommodating as possible.
As I enter my flat I'm surprised to see a suited figure. I froze assuming the stranger a burglar. The bright sunlight made it impossible to tell anything about the person, other than the shape was female, standing with her hands on her hip, blowing a plume of smoke into the air. As she steps closer and became more visible a smile spread across my face.
'What do you think of my costume?' Trudy laughs. She looks amazing in my blue pinstripe suit, crisp white shirt and red silk tie. Hair tied so sternly back it looks cropped close to her scalp and with no make-up she looks incredibly sexy.
'Excited?' she asks dragging me to our bedroom. I try not to look overtly willing. 'Oh! Honey, come with me now on a journey to glorious femininity, where I'll beautify you and dress you in the most sensually girlish clothes.'
'Steady on, stop it,' I cry feeling a flush of embarrassment flow through me. 'Let's not get carried away. It's a fancy-dress, right?'
But she didn't stop.
'Oh! Honey, in a few minutes you'll pass as a ravenous girlie babe.'
I feel my eyes glaze over and a glimmer of regret flashes through me. It's one thing having kinky dreams but a whole new experience when faced with it.
'Hurry, darling, we have to be there in forty minutes and there's lots to do. You do want to go don't you?' She knew I did.
As she directs, I shower and shave my body silky smooth, pat myself dry with a towel and cover myself with her greasy moisturiser. Smelling like a tarts handbag she practically frog-marches me back into the bedroom to change. She immediately points to a door on which hung a pale-pink dress with capped sleeves in some light, gossamer fabrics. It looks incredibly expensive.
'Well, what do you think, David? Isn't it adorable?' She fingers through the pastel folds of the dress.
I nod awkwardly.
'I wasn't too sure of your size. I had to guess. It's a 12 but I might have been too optimistic. What do you think?' She smirks and a shiver of apprehension slithers through me.
I had no idea and nervously look away. My eyes rest on our bed. Ugh! I feel my jaw drop in horror at the assortment of pretty lingerie neatly laid out for me.
'I, I, I,' I stutter, 'I thought I only had to wear the dress! Not all that!'
'Nonsense,' she says leafing through the silky items like a junkie seeking a fix. 'You can't wear this beautiful dress without these panties and matching bra! Your own briefs would ruin the line of this dress and you have to fill out the bust with something, don't you?' I nod my head. I was no expert but she had a point.
'Promise you won't laugh?' I ask nervously as the towel round my waist drops to the floor and she passes me the panties.
'Did you laugh at my costume?' gushes Trudy. 'Don't worry you'll be amongst friends all wearing something similar.'
Reassured I step meekly into her silky panties admiring the beautiful lace detail and wonder if she wore my plain cotton boxers under my suit trousers. I pull the skimpy material up my clean-shaven legs, and when at my waist, I feel my manhood rub against the soft, sensual material. Their caress excites me, and I start to get erect! Fortunately Trudy doesn't notice, preoccupied wrapping the matching bra round my chest. She feeds my arms through the delicate straps and I shudder as with skilful ease she clasps the bra together and stuffs the soft cups with two doughy type bags. They feel terribly realistic, firm and heavy, swaying to and fro as I move. I gasp at my cleavage and I couldn't believe my eyes when she completes my breasts with a pair of false erect nibbles'
'These will raise a smile,' she says slipping them between the cups. I stand still in stunned silence as they protrude proudly and are clearly visible through the lace. My cock continues to swell as she rolls them between her thumb and forefinger.
I sigh and feel strangely different. Her extreme attention too detail excites me and I chuckle to myself looking like a porn star on heat.
'They look so authentic,' she gasps. She's right. Gazing down at myself a weird shudder cascades through my body as if injected with female hormones. Odd... but I felt embarrassed with their prominence as if they were part of me. The panties and bra had a strange property about them. As if magical, there very presence on me made me delightfully feminine. I shake my head in disbelief, scared of my feelings. More strange sensations were to come as following her directions I step into a silky slip and drop a camisole over my head. They both feel cool and slippery, gliding over my body with the slightest movement. She senses my delight and for the first time notices my growing pleasure. She giggles at the sight of her excited boyfriend in panties, and a bra.
'You promised not too laugh' I cry.
'I'm not', she lies, 'you look gorgeous, why should I? You look like dynamite. Your legs are so curvaceous and your waist so small. Though we definitely have to do something about this.' She taps my bulging cock disapprovingly.
'Hmmm!' I groan.
'Oh! Honey, Feels nice does it?
I nod sheepishly.
The dress was a terrible extravagance, but admit it's stunning. I'd never seen her wear anything so beautiful. It was obvious she was intent on me projecting a very feminine image. She wanted me to convey a look of sophisticated sensuality not a bloke in drag as I had originally thought.
'Hired,' Trudy says as I wonder where she had got it. 'I got carried away. Fancy-dress parties can be spoilt if the guests don't make an effort. Don't you agree?'
I meekly nod.
'I didn't want to be stingy. Although, I have to admit, I threw sensible out of the window when I saw this gem. Just be careful you don't get it dirty or damaged. The deposit alone was a fortune.'
My mind was a whirl. Such effort. Such detail. For what? A fancy-dress? It didn't add up. She unzips it and holds it open invitingly. In a daze I did as she directs and step into the short, floaty dress. Hmm! As the dress flutters against my legs my cock almost bursts the sensual fabric fanning the flames of passion within me. My senses are bombarded with different sensations. The dress smells fresh and clean like a pretty English garden in early spring. In a dream I pull it over my slender frame. The smell of fresh flowers envelops me; the soft, light fabric sends shivers darting throughout my body. It fits perfectly and as I slip my slim shaking arms into the sleeves my little cock stiffens yet again and I feel strangely different. The dress finishes well above the knee and is much shorter than my modesty would have liked. My large breasts stretch the material in a tarty manner. I frown smoothing the soft dress over my rump, and when I see the faint outline of my panties, my cock swells even further.
'That's what I call a result,' Trudy says zipping up my back. Locked in the dress I knew then that the experience was burning into my memory and would be one that I could conjure at a moment's notice. I console myself with the thought that Guy wore a similar girlish outfit and probably felt just as awkward.
'Now, long pink earrings, this dress, a colourful wrap and delicate heels are the perfect formula for party dressing this summer... and you're not walking round London with those white sticks you call legs either. I don't care what you think, you're wearing tights.'
I groan, mainly for effect, as I want to wear the tights. I felt a compelling need to complete my look. A girlish wave flickers through me as Trudy hands me a pair pale pink hold-ups. Even better I thought. Called 'Provocation' they were absolutely gorgeous, but according to the packet they cost twenty-five quid. Can you believe that? Just for a pair of stockings. I'd never held anything so sheer and my hands tremble as I held one open and slip a nervous toe into them. Oh! They felt wonderful as the nylon engulfs my foot. My cock twitches uncontrollably as I slide them up my legs. Never before had I felt something so nice. Their effect was amazing. I hadn't realised how long and well-proportioned my legs were and what a good figure I possess. I glow with pride and run my hands up and down my smooth legs. The hold-ups were an excellent choice as the dress clung on the hips and suspenders would have shown through horribly. Standing in her lingerie sheathed in the pink nylon stockings something strange happens. Up until then everything I wore seemed alien and odd but suddenly it all came together like finding the final piece of a jigsaw and collectively the dress, panties, bra, and hold-ups felt wonderful. I had dreamt of this many times but this was my first ever experience of the realities of wearing female clothes. Wearing such feminine cloths lit a beacon in my heart that burnt brightly and unleashed an emotion I would never again manage to put back in its box. The thought terrified me.
Trudy sensed a change in my attitude.
'How you feeling now, Honey?' she asks soothingly. 'Pretty huh? Don't you just love wearing a lovely bra that's filled with your very own boobies?' she giggles; jiggling my breast while her other hand felt my tightly encased balls. I struggle to answer, as my minds awash with pleasurable feelings.
'Hmm! OK,' I say slowly, desperately trying to under play my real emotions.
She wasn't fooled and smiles knowingly. Next like a magician with a rabbit she pulls from a box a beautiful blonde, shoulder length wig. She smiles and combs it with loving affection.
'It's so fashionable to have unkempt curls. There's something incredibly sexy about hair that is sun and sea tousled. Don't you agree?'
I nod, my heart beats wildly but as she pats the stool in front of her for me to sit down I began to feel we had over stepped the mark. Fantasy was blurring with reality. I had never made such an effort for a fancy-dress and I began to worry that I would look rather too convincing. No time to contemplate my fate as she pulls the wig tightly over my head. Like the dress it fits perfectly and she combs the wavy curls into place.
'All this,' I stutter. 'It's a bit extreme isn't it?'
'No, no, no,' she clucks proudly. 'You can never over dress for a party.' She sprays me liberally with hair spray. 'You'll wow everyone with this hair and heads will turn.'
I dwell on this thought then shake my head unconvinced. My new hair sparkles and shines alluringly. Next she paints my lips scarlet with a buttery lipstick and made-up my eyes with a velvety shadow.
'Oh! Trudy, do I have to wear lipstick and all this make-up, too? I whine, watching her erase any trace of masculinity from my face.
'What a silly question, of course you do,' she says, lengthening my eyelashes with her mascara.
'I, I, I can't imagine Guy or any of the others going to such lengths.' I stutter slipping on a pair of towering heels.
'Oh Honey! You'll be surprised what men do but you'll have to wait and see.' She sprays me with a perfume she calls flowers and finally blots my lips on a tissue. I totter in front of her floor-length mirror. I couldn't believe the reflection that shone back at me. I look amazing. The dress accentuated my slim waist; the stockings made my legs look incredibly long, the heels made my ankles look slender and my stuffed bra gave me an enviable hour-glass figure. I ran the palms of my hands smoothly down my sides and revel in the feel of my wide hips under the dress.
'Mmm' I moan. I found it hard to believe I was actually dressed as a convincing woman. I was living my dream. Every time my legs rub together my short skirt skims my knee and my heels tap lightly on the floor. Every new experience I approach with wonder and yes, enthusiasm. It was a naive innocence yet to be sullied by a single iota of ridicule and humiliation. With the time approaching for us to leave it was unlikely to last. My little cock, encased in pretty panties, twitches as if to remind me of its presence. I was extremely pleased - and sensually excited - with the end-result. I never dreamt I'd look so good. Trudy's delighted too.
'You look amazing,' Trudy gasps shaking her head in disbelief. 'Let me see your bust, dear,' Trudy asks, pulling me toward her. She examines my padded cups as if they were her own, kneading and fondling them, nodding her head. 'Oh, yes! These are just perfect! How do you like them?'
I look down at the squishy mounds protruding from my chest. I couldn't see my dainty feet. 'I detest them!' I lie, feeling them hanging from my chest like large melons.
But more was to come. In addition to insuring that I appear as one of the prettiest girls at the party, Trudy insists I act out the role. She orders me to parade up and down the room swinging my hips. I did as she asks, feeling very foolish, but after a few minutes I got used to the heels, the dress and the heavy bra
'David, Honey, you're a natural girl!' Trudy says. 'The only thing that looks a little out of place is this bulge,' she points to my hard-on. 'Something's got to be done about that! Still we don't want you looking too good do we?' She threw me a knowing smile. 'I don't want to be jealous.' I laugh but fail to comprehend her intention. She gestures me towards her and we sit together on the bed motionless for a few moments. She softly caresses my cheek and I shiver, terrified of my own sexually charged emotions. Slowly she turns her face to me and drew her lips to mine. We kiss shyly at first. I felt only utter exhilaration and feminine pleasure experiencing a girlish role. She was the f***eful kisser, leading the way with her probing tongue. Trudy gently stretches me back on the bed and began to run her hand across the shiny fabric of my dress. All the time telling me how beautiful I look. She presses her lips to mine and strokes her tongue inside my mouth. I respond by sucking delightedly on the moist appendage and draw it deeper into my throat. We clutch at each other, savouring the moment. Inadvertently I raise and spread my legs, the action opening wider the front of my dress. Trudy's hand went immediately to my legs and began to caress them, slowly at first, her fingers sliding across the smoothness of my hairless legs and then massaging my thighs. I sigh, I gasp, and I feel delightfully feminine.
'Oh, God, David, you're so, so ... Sexy.'
'Make love to me, Trudy, make love to me like never before.' As if answering my prayers, her fingers edge to the waistband of my panties and pull them slowly down my legs. I shudder aware that I was assuming the submissive feminine role but Trudy didn't seem to mind. I let out a little moan, lift my body to accommodate her movement and my white undies slither across my expensive silk stockings and land crumpled at my ankles. Trudy's hands continue probing and soon settled at the top of my hold-ups. She ran her right tantalizingly over the lacy tops and softly caresses my groin. I couldn't bare it. She's driving me crazy introducing me to totally new sensations that burst and fizzed inside me. Then her long fingers grasp my slowly stiffening cock and hold it firmly. She smiles while squeezing and kneading my cock knowing that I was about to explode.
'Who's a bad girl,' she scolds then thrusts her tongue deep into my throat again and we press our bodies against each other in a passionate embrace. Suddenly she pulls herself away from me.
'We haven't long, honey, we'll be late.' she sighs. 'There's plenty of time later.' From now, I want YOU to be my girlfriend! And that's not how they behave.' She squeals as her hands went back up inside my dress and stroke my shaft slowly.
Disappointed I pull my panties back on and smooth down my dress as I'd seen Trudy do many a time.
I try to look down at my groin as I was convinced my cock must show but I couldn't see clearly because of my new chest, I could see that my breasts were larger then Trudy's, and my dresses thinness did little to hide my erect nipples protruding from my bra!
'Bar that little tell tale bulge, you look just like a girl,' Trudy squeaks excitedly.
'Have you lost your mind?' I say frantically, 'I can't possibly pretend to be a girl! This is a fancy-dress party. We're seeing friends. I'm in drag. I'm not trying to be a girl.'
I look down at the dress on my body, and feel helpless. No mistaking I was dressed completely as a young lady, and now I also had to pretend to be one.
'Oh David, hush now,' she says emphatically. 'You now look and act like a girl so perfectly, that no one will know who you really are if you're careful.'
'But Trudy, I don't WANT to be a lady. This is a fancy-dress. Don't read into this more than what it is. It's just a bit of harmless fun, right?'
She laughs and a hint of a smile plays across her lips.
'Its OK for a laugh But It's not right that I'm wearing this dress seriously.'
...And panties' adds Trudy, '...and hold-ups ...and a cute little bra? She fondles the lace on my dress.
'...YES! All of those!" I cry, standing up quickly. 'I'm a MAN! Not a WOMAN! And I don't want to pretend to be one girl!'
Trudy looks disappointed. 'But David, honey, what are you afraid of? She took my hand and pulls me back down to the couch.
'Are you afraid that you may start to enjoy being a pretty lady? Worried that all the ladies won't like you as a girl?'
She was close to the truth but I couldn't say that. 'No,' I scoff 'don't be stupid' her hand was now on my bare knee.
She laughs and insists that I behave like a young lady, teaching me things like smoothing my skirts under me when I sit, walking, curtseying, and she even made me speak in a high, girlish tone. Needless to say after a while I get accustomed to balancing in the heels and wearing the dress and with minutes to spare she suggests we both wear our large raincoats so no one could see what we're wearing underneath. Good idea I thought while I put HER knee-length coat on she disappears into the bedroom. She's gone for ages.
'What's keeping you,' I cry impatiently.
'Coming, Honey' she calls and when she did reappear she wore my raincoat fastened to the neck. It was almost impossible to see what she was wearing but I felt reassured when I saw my pinstriped trousers and black brogues on her feet. Of course there was no mistaking my legs wrapped in hold-ups adorned with a angle chain and squeezed into 4" heels. As we left the flat she picks up a small holdall which I assume had our change of clothes.
I tip-tap my way down the stairs knowing that I look very sexy. The thought kept my body racing at fever pitch. I was still sexually excited from our antics on the bed and just hoped that my cock would soon settle down. Relieved I wore her coat.