I wrote this for the New Year (2016) but got bogged down, I showed a friend who said I should post it anyway as she enjoyed it, so here it is.
I will probably continue it later on, but for now I hope you enjoy the story so far.
It was New Year's Eve and Harold was bored, he was bored out of his skull in fact! He was not the brightest of minds at work and he fancied, Diana, the blonde secretary in the office, but she didn't respond to any of his tentative advances.
So as the firm was closed for the Christmas period, he decided to go shopping to see if he could find something to pass the time over the rest of the New Year break. Somehow he ended up at a run down shopping Mall at the butt end of town. Looking around he found very few shops that were still in business, never mind open, but there at the end of the west wing a gleam of coloured lights caught his attention.
Walking down the wing he found himself outside a store with displays of lingerie and bondage gear! Not something that normally drew his attention, but today things seemed to plotting to draw him into the store, a combination of boredom and unfulfilled lust for Diana perhaps? Or was there a bit of leftover Christmas Magic involved too?
Entering the shop he was surprised just how big and bright the store was, considering the location in a run down part of town. He ducked into the racks of sexy clothing just in case anyone he knew was around and just in time too! He was amazed to see the object of his dreams, Diana, walking though the store carrying a number of items to the tills, not just underwear, but bondage toys for female fun! Wow, he had misjudged Diana's preferences.
She seemed to be known to the shop keeper who was dressed in a tattered bath robe, unusual to see a shop keeper wearing such an item Harold thought. He greeted her as a long time customer and had soon totted up her purchases and wrapped them up for her and after she had paid, he gave her a quick kiss on her cheek and sent her on her way.
No sooner had Diana left the store, the shop keeper turned and looked over to Harold and greeted him as if an old friend. "Hello Harold! What can I interest you in today?" he asked.
"Wha... Sorry how do you know my name? I don't think we've ever met?" Harold stuttered.
"Well, as you don't believe in magic let's just say I'm the Wizard and I read your mind when you came in here."
"The Wizard??" Harold said hesitantly. "What Wizard?"
"Why, the Spells 'R' Us Wizard of course! You don't think you came in here by accident do you? Especially not in time to see Diana buying her Bondage toys?"
Harold flushed bright red!
"So, do you want to play believe or not believe? Or shall we move on to how I can help you get Diana interested in you?"
"What, how could you help me do that? WHY would you help me for that matter?"
"Well, part of my job is knowing just what my customers really want and how best to make them happy. That way, they'll keep coming back to buy stuff from me, thus keeping me in business. So, are you interested? It won't cost you too much just a little bit of work on your part and by tonight Diana won't be able to keep her eyes and hands off you, nor want to let you go back to being uninteresting to her. Promise!" The Wizard said as he winked knowingly with a sparkle in his eye. No really, there was an actually sparkle in his left eye as he winked!
Well, Harold didn't stand a chance and before he knew it, he was back home with a large bag filled with sexy clothing and bondage gear along with very specific instructions of what to wear, in which order and how to put stuff on, after all, this was the first time he had even considered wearing ladies' clothing, never mind bondage. Why was he considering wearing bra and panties, never mind skirts and blouses? If you'd been there and asked him, other than being totally embarrassed, he wouldn't be able to answer you.
Back home, he drew the curtains and stripped off, a quick shave and shower later he was drying himself off. Looking at the all the items and the instructions laid out on the bed he opened the packet of black satin panties and put them on, adjusting himself so they were a comfortable fit, then the black 60 Denier tights went on, one leg at a time, pulling them carefully into place around his waist, before opening and pulling the black firm control satin shiny Flexxes, a size too small for his waist, though it didn't seem to matter once they were on and pulled (very) snugly into place.
The black sexy "Gemm" bra was next though Harold had to put it on by having the clasps to his front so he could see them and work out which set was the best fit for him. Pulling them around his body so that the cups were now in front of him, he pulled the bra up to his moobs and pulled the straps onto his shoulders, then slipped in the 40D breasts forms into place in the cups and they fitted perfectly. They were a bit cold and stiff at first but they warmed up very quickly and soon moved and felt just as Harold thought real breasts would act and feel. They were however quite a bit heavier than Harold had expected.
"Wow, how do women cope with a couple of bags of sugar weighing them down in the front?" He thought.
He moved around the room, cupping his breast forms in his hands, getting used to the extra weight. Next he opened the packages with the blouse and skirt and with a little confusion over fastening the blouses' buttons, with them being on the wrong side after all, he stepped into the short tight skirt which, as he walked past the bedroom mirror, he couldn't help but notice how much the skirt accented his bum so it looked like a women's butt, sticking out nice and curved.
The final items where a long blonde wig and a pair of patent purple heeled shoes and his outfit was complete. Walking in the heels with the unexpected weights pulling him off balance he struggled at first but after a few minutes he started to get used to the feel, even if it was helped a little by a bit of magic though he didn't know that.
Grabbing his outdoor coat he placed the extra items as he had been instructed into the coat pockets and locking up after himself, he set off walking in his heels, to Diana's apartment as he knew she had moved a couple of years back to a new block of flats not that far from his own.
It was dark and no one was around, he soon made it to Diana's door, not without more than a couple of twists of his ankle in the heels, he was still very new at it after all. So first item out of his pockets were a pair of leather cuffs which he fastened around his ankles, squatting down rather than bending over with his now shapely bum up in the air exposing his panties, a short length of chain was next, along with two padlocks and he quickly fastened these to his ankle cuffs.
Standing up he took a panel gag out of his pocket and quickly fastened it over his mouth, feeding the penis gag into his mouth and strapping it tight around his head. A small board on a length of string was hung around his neck so that Diana would be able to see it once she opened the door. Finally a pair of hand cuffs came out of his other pocket and he fastened the cuffs to one wrist, then he rang Diana's door bell and quickly placed his hands behind his back and fastened the second cuff to his other wrist.
He waited outside her door for what seemed like half an hour but in reality was more than 5 minutes as Diana got herself presentable to answer the door as she had been busy playing with her own toys.
Furious at having her play time disturbed she opened the door only to find a woman with long blonde hair wearing a gag and cuffs standing there.
"What do we have here?" she murmured. Her eyes roved up and down the woman's shapely body for as Harold had made his way to Diana's, the Wizard's magic had been working on trimming down Harold's body into that of a sexy female with curves in all the right places.
She reached a slender hand out and held the sign dangling past Harold's 40D chest and read it out loud for Harold's benefit as it were.
"Dear Diana, here is that present I promised you when you came to my shop this afternoon. I told you it would be delivered tonight didn't I, and I always keep my promises. The Wiz."
"Oh thank you grandfather!" Diana said softly to the air, then "Well, come on in, there's no need to stand out here all night giving that pervert across the road any free views. We're going to be far too busy the rest of the night Helena!"