Dream Date

byTomsparty©

Who would have thought it; I was reduced to finding a partner on the Internet? I had read about these dating web sites and though dubious I found one, completed my details and waited. A few days went by and I heard nothing. I waited a few weeks and still I heard nothing. I turned to an old girlfriend for advice. I'd known Julia since school and though close our relationship was plutonic and I loved her like a sister. She was quick to help and offered to come round and have a look at my profile.

A few days later, beer in hand, she was sitting next to me on my sofa, laptop on her knee. She wasn't impressed. She felt my profile was all-wrong, it didn't paint a true picture of my personality and my photo didn't do me justice. All in all she wasn't surprised I'd had no one enquiring about me.

First we had a long conversation about my ideal woman. I told her in nauseous detail; tall, slim, hourglass figure, long blonde straight hair, blue eyes and a warm smile. She was disappointed that I hadn't mentioned her character.

'You know,' I said, 'someone like you but feminine.' Not surprisingly this agitated her, as Julia was short, over weight, with black curly hair and dark brown eyes with a mannish appearance.

'You don't deserve someone like me, you're shallow, fickle and too fucking picky for your own good.' she screamed. You're despicable.'

I shrugged my shoulders. She was probably right but I couldn't help it.

I trusted her implicitly and let her have free reign. I gave her my password and she merrily changed my profile while I popped out and got some more beer from the local off-licence.

On my return she proudly showed me what she had done. I wasn't very pleased and needed another beer. I no longer sounded like a man. She made me sound effeminate, weak and submissive. She had changed my profile name from 'Leaping Tiger' to 'Pretty Petal,' said I enjoyed dancing, playing the flute and digital photography. I was a follower of fashion and I loved long walks in the country, the theatre, cooking and entertaining. Only the digital photography bit was true. I sounded like a complete wet sissy.

'Today's woman wants a sensitive guy who can look after themselves, be caring and loving, not some athletic hunk who plays golf all weekend and drinks down the pub.'

'But I don't play the flute or go to the theatre.' I moaned.

She laughed, 'That's a creative license, how many hopefuls give a true profile, besides you enjoy cooking and entertaining. Don't be so whiny, trust me on this, what do you stand to lose?'

'Ok ' I say, 'but fashion, I had never considered myself a follower.'

She looked at my jeans and T-shirt then the goofy picture of me on my web profile.'

She nodded in agreement, 'Show me your wardrobe and perhaps we can find something more appropriate.'

Minutes later she was rummaging through my closest and chest-of-draws as if she was my mother. I could tell by her sighs that she wasn't impressed. I left her to it and poured us another drink. At least I was having fun and by now I was feeling quite intoxicated. On my return she had found an old pair of trousers and a colourful shirt. I didn't recognise them at first then realised they weren't mine but cast-offs from an old girlfriend. I laughed. 'That's a women's blouse, I think and a pair of ladies trousers,' I said. 'I'm not wearing them.'

Julia smiled and her fingers where already tugging at my belt as if my words had fallen on deaf ears.

'You really have to trust me. A future girlfriend wants to see you in something colourful and bright and all your wardrobe consists of is blue jeans and black and grey tops. Dull, dull, dull. Now don't be such a baby. It's only a photograph I'm going to take, they won't be able to see detail.'

I grin sheepishly and reluctantly let her pull my jeans down and T-shirt off like a mother undressing a child.

Dressed in just my underpants her hands were soon all over my smooth willowy legs like a rash.

'My goodness', she gasps, 'your legs are amazing you keep them well hidden. They're so long and smooth. Do you shave and moisturise? You shouldn't be covering them up.'

Flattered I smirk but ignore her remarks.

The slacks where as you can imagine incredibly tight on my bum showing every curve but straight legged and flowing almost like old fashioned flares. My baggy underpants caused the trousers to bunch and crease rather unsightly.

'I'm not sure if these will give off the right message. They're quite obviously for women.' I say, 'they have no front fly, no pockets and a side zip. Men's trousers just aren't designed that way.'

Julia was disappointed too. 'You'll have to take those awful underpants off,' she said. 'They're making your bum look deformed.'

My eyes widened and I felt myself blush. 'Don't be daft,' I said.

'But those underpants are truly awful you should be ashamed. You're a typical guy, have you no shame?' She then rubbed her chin thoughtfully, 'there is an alternative,. She grins sheepishly like a naughty schoolboy. She rolls her eyes. 'Have you got any panties from your old conquests?' she almost spat the words.

I was reluctant to admit, I had but she didn't wait for me to answer and soon found a minuscule pair of silk panties with lace trim in a top draw.

'l don't believe you,' she said laughingly, 'all these girlfriends leaving their clothes here at your stud pad. Where are these beauties now or are you telling me porkies and these pretty things are really yours?'

I stare at her aghast 'They're not mine, stupid,' and blush as she slid them up my legs. I wiggle my hips sending a unexpected yet delightful warm sensation sweep through me as the soft silk caressed my cock like a glove and the lace tickled my skin.

The slacks glided up my legs and hugged my bum like a long lost friend, this time with no unsightly creases. With their polyester mix they slid over the panties like slippery eels heightening the wild sensations that now careered throughout my body like a crashing car.

Though all was not right, rather alarmingly because of the tightness of the material they now stretched across my bum like the skin on a snare drum hugging every contour and I easily saw a visible panty line.

'For crying out loud,' I shouted. 'You can see I'm wearing girls panties.' I reach down to take them off but Julia smacks my hands away as if a child stealing sweets off a counter.

She smiled dismissively and I saw just a trace of satisfaction. 'Actually,' she said, 'I think you look rather hot and don't worry no one will notice.'

I pulled the long colourful top down over my bum in an attempt to hide the obvious but it just made matters worse. The shirt wasn't a shirt or even a blouse but a short silk jersey dress with full-length tie sleeves and a scooped neck. I shuddered, closed my eyes, screwed up my face into a snarl and stamped my feet like a child in a supermarket.

'This is crazy,' I gasp but Julia ignored my tantrum choosing to pull it about until it hung correctly making my shoulders look slight and my arms slender. I smelt the feminine perfume immediately and the soft, silky fabric tickled my skin sending shock waves like electric current through me. My cock began to throb excitedly, straining against the tight panties that where cocooned in the stretchy slacks and I began to feel strangely aroused. I resumed my usual calm and felt my cock dampen with precum.

Not wanting to make a spectacle of myself I closed the bedroom curtains as Julia returned to my wardrobe like a squirrel looking for stored nuts. She rooted right at the back and at one point I thought she might climb in.

'When did you last say you had a girlfriend,' she said finding another dress, a paisley mini skirt, a pencil skirt and a black wrap. 'These are gorgeous I'm surprised they didn't want them back. You've got a women's wardrobe squirreled away.' As if a pirate hunting for buried treasure she crossed the room and rummaged in my chest-of-draws and found tights, more panties, stockings and a bra.

I blushed. 'I really need to do a clear out,' I say.

Next Julia was on the bed beside me rummaging in her tiny make-up bag that she had pulled from her shoulder bag.

'Now I know you'll complain but just bear with me while I explain... Your eyes are the windows to your soul and your lips must be plump and kissable if you want to be sexy.' she laughs and gives me a cheeky grin. 'Your current picture makes you very lifeless and unattractive. I don't know what you where thinking of when you put on that shirt for the picture it makes you look ashen.' Don't worry I will only add a little powder here and there to give you some extra colour. All the actors on TV wear a smattering of make-up for the camera.'

So I sat there bemused and slightly sozzeled in girlish slacks and a mini dress on the pretence that she was making me more appealing as she plucked my eyebrows, dusted my eye lids with shadow, lengthened my eye lashes with mascara and painted my lips with a bright lipstick. It struck me as more than a little powder but frankly I enjoyed the attention and the alcohol had made me rather woozy and sleepy.

'I hope you know what you're doing,' I mutter in dismay as she brushed my hair as I felt myself transformed.

She nodded like a make-up artist on a film set but was concentrating so much she said nothing.

A minute later she's shooting me with her digital camera as if a gun and telling jokes to make me laugh but by now I was sufficiently drunk to laugh at anything. She made me stand, sit, bend and crouch and strike a variety of poses like a model in a clothes catalogue.

Finished she loaded the best pictures onto my web site but refused to show me until done. It's true I could have changed at that point back into my tatty jeans and T-shirt but I now rather enjoyed wearing the smart slacks and mini dress.

I was later horrified with the pictures she loaded. They made me look very suspect. It wasn't obvious as to my sex. I could easily be a girl or a boy and even reading my profile didn't help despite it saying I was a male. I looked like a young, happy girl wearing make-up. I was furious and felt duped but it was late in the day and after losing count of the number of drinks I'd drunk, I was past caring and decided to avoid an argument. I didn't want to upset a friend so I thought I'd change it in the morning... Or so I thought.

Just before leaving something inexplicable happened to Julia. She looked at me oddly and I saw a strange sparkle in her eyes. At the time I wasn't sure if it was due to the alcohol we had consumed but there was no mistaking her mood changed. As she offered to help me undress I felt a little uneasy. I was quite capable of changing myself but she was most insistent and I was soon standing in front of her again her nimble fingers pulling my stretchy slacks down yet again. With nothing on my legs, the mini dress came into its own falling just below my groin transforming my appearance yet again. It was now unmistakably a woman's dress even a blind man wouldn't confuse it with a shirt and with my legs exposed I felt naked and humiliated.

'Oh my goodness,' she gasped walking around me, eyes on stalks, staring at my long slender legs poking from under the material. 'You look amazing.' She darts over to my wardrobe and pulls a pair of discarded heels from the bottom of my cupboard and before I know it I'm slipping them onto my feet without a care in the world as if in a hypnotic trance.

Fortunately I've only small feet and they fit incredibly well to the surprise of us both.

I stand upright and totter around the room, the dress feeling very much like a dress as the hem tickles my sensitive thighs like a thousand tiny hands.

'You look stunning,' Julia says again gesturing that I look at myself in the wall mirror.

I gazed at my refection hardly able to comprehend the beautiful image that reflected back at me. 'I do look very pretty,' I say.

'Indeed,' Julia was smiling. Her face was so calm it was beautiful. 'You would send many men's heart fluttering. You look very comfortable.'

She was right I felt terrific. I enjoyed the sensation and despite being unfamiliar with baring my legs I began to get hot and excited. This scared me somewhat and in a weird dream I bent to pick up the slacks, which were lying crumpled on the floor.

Julia squeals with delight. 'I can see your panties,' she sings merrily. 'Aren't you the pretty one?'

'Stop it,' I say but my voice wasn't near strong enough and lacked conviction. She could tell I enjoyed the openness of the dress and the air around my legs and above all I enjoyed feeling like a woman.

Confidently she rummaged back inside my draw like a child at a fair playing lucky dip in a barrel of sawdust. She squealed with delight as she found a prize - a pair of old girlfriends tights.'

'Whose where these?' she said brandishing them in the air and without waiting for a reply or even asking she pushed me backwards onto a chair.

I'm not really sure what came over me as I kicked off my shoes and Julia scrunched one leg of the tights in her hand. I was in a drunken trance as I offered her a toe and seizing the opportunity she slipped it over my foot like a net. I gasped as she slid it up my thigh then repeated the process on the other foot. Both feet cocooned I stood up to let her slide them further up my legs. There was no denying it they felt amazing and as my cock spasamed I feared that I might ejaculate. What would Julia think of me I mused so to avoid any further embarrassment I bit my bottom lip and slipped the heels back on. Remarkable I now felt dressed and less foolish when I wore just the dress over bare legs. True I felt like a young lady but I revelled in the warm sensations that where hurtling throughout my body. Julia fetches us both yet another drink and I sit back on the sofa carefully, drink in hand, and crossed legs so as not to flash my panties again. My tights rasp like a saw drawn through wood and I feel wonderful.

Julia sits beside me and we chat for a few minutes. Then to my surprise she shuffles closer so that she's almost facing me, takes my glass and places it on the floor. She then casually puts a hand on my knee. Now that in itself wasn't extraordinary as she was quite a touchy, feely person but this was different and her wandering hand was soon under my skirt sliding in-between my thighs. With her wearing the trousers and me in the dress I felt very defenceless and weak. But I couldn't control my pulsing cock and it strains against my flimsy panties until it breaks free. I shuffle in the sofa causing my dress to slide alluring over my tights and panties like a skater on ice. Julia simultaneously lunges forward and her mouth hovers over mine like a bee about to extract pollen from a flower as she pushes me backwards into the sofa and her hand slides further up my skirt until it brushes against my cock. She pings the gusset of my tights and kisses me passionately her tongue probing deeply but with the tables turned I panic and feel out of control. I struggle to get up but with a magical strength she pushes me backwards and almost paralysed with surprise I fear rape.

'Stop it,' I manage to cry pulling my mouth from her lips and with a burst of energy I pull myself free. I stand, trembling and brush down my dress unsure what to say.

She looked cross and rejected and I expected a scene and wondered if I should have succumb to her advances.

'I'm sorry,' she said, 'I don't know what came over me.'

I was surprised that she was so accepting but to be honest it wasn't as if I had been leading her on. What did she expect? I don't automatically bed every woman that comes into my house. Besides this was Julia not some tart I'd picked up in a club.

'That's ok,' I say. But I'm not sure if it was. My old friend Julia was hitting on me as if a guy and I felt very uneasy. She left quickly after that and alone in my tiny flat dressed in the mini dress I was left pondering how this wasn't going to affect our relationship.

Next day when I went into my online date profile I was amazed to find a full inbox with over twenty interested people all wanting to date me. I was made up... Until I read their messages. They where all weird. Most of them had assumed I was a crossdresser as feared and I enjoyed dressing as a woman. In a panic I quickly tried to change my profile but found my so-called friend, Julia had changed my password so I could read only.

Angrily I read my emails again. But since her efforts had generated more responses than ever I thought I'd give them a second chance. I read the emails with a bemused sense of interest. Some where bizarre others erotic making wild and rude suggestions. One wanted to see me dressed in lingerie on all fours with my flute up my arse. Another wanted to know if I'd dress as a policewoman and let them bind me with rope, blind-fold me and put a ball gag in my mouth as they urinated over me. Another openly wanted to take me for a meal, dancing and then back to theirs so they could fuck me. I was horrified. The whole experience was an eye opener. I felt so nieve and inexperienced. And what a mixed bag as though I was quite explicit with who I wanted to meet none of the women who supplied photographs where blonde or had blue eyes. Many where from men and others from women who looked like men none where what I considered feminine. Out of my full inbox only one sounded totally normal and though no photo was supplied she said she had blonde hair and blue eyes. Had I found my perfect partner?

Julia rang a few days later and never mentioned me wearing the dress or hitting on me, instead she asked me if I'd heard anything from the dating agency. I told her how I had sorted them into three piles; no way, maybe and yes definitely. Julia asked to come round to see my selection.

She didn't seem as surprised as I as she flicked through my inbox messages and though she agreed with my 'yes' selection she enthusiastically favoured the girl with no photograph above any of the others. Though despite her views I thought I was foolish to put all my eggs in one basket so I replied to all of my 'yes' selection

A few days later a couple replied out of courtesy but had obviously lost interest, some never bothered to even reply and some of them I hated the sound of but one girl intrigued me. She was called Lucy and surprise; surprise was the girl with no photo. And that's how we began our cyber relationship. We exchanged half a dozen emails and I learnt about her hobbies, the music she liked, the films she watched and the books she read. She sounded fantastic and unlike the others she ignored my feminine photographs until. I told her I was going shopping that weekend for clothes. My passing comment opened a sluice gate. She began asking me a series of really odd questions. She wanted to know if I liked tights or stockings and if I preferred dresses or skirts and when I told her I was only buying a shirt and tie for work she seemed bitterly disappointed.

'No new panties decorated with ribbons, bows and lace then,' came her reply.

I was mystified. And dismissed her comment as a joke but after coming back from the shops I received another email. 'What did you really buy?' she asked, 'Figure hugging lace panties or a skimpy thong?'

I ignored her questions but the next day she asked me about my profile photographs. She appeared fascinated with what I was wearing. Who made my top? What was it exactly and did my trousers have a fly zipper.

'Don't be coy,' she wrote. 'I'm not stupid I can tell you're wearing a mini dress over women's slacks.'

I froze to my keyboard and hurriedly typed a response.

'It's just a bright top and tight trousers,' I type back.

'Yeah right,' came the reply, 'and why are you wearing make-up?'

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byTomsparty© 6 comments/ 64959 views/ 2 favorites

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