s there is a dirth of stories being posted I sat down and started this - I have ideas as to where it might go - if you want more please post and tell me if you are enjoying it. I write for an audience, if there is no one there I'll save myself the trouble!
Oh what a tangled web
Part 1
Simon was well and truly caught in web he had woven for himself. He had been incredibly stupid and had ordered some clothing from ebay using the joint credit card. He hadn’t intended to use that card, of course, but he was so dazzled by the beauty of the dress with all its frills and petticoats that he just had to have it – and the auction was ending in 5 minutes! Of course he bid the highest - £125 wasn’t cheap, but it was worth it and when he picked it up from the post office box he’d set up for all his “secret” purchases, he couldn’t wait to try it on.
That was about 3 months ago just before Simon’s world was turned upside down.
Simon and his wife, Jenny lived in a little village in the South of England. They ran a fairly successful mail order business from their comfortable home. They had been married for about 5 years. Jenny, who was in her early thirties, was one of those tall assertive women who know what they want, and usually get it. She had previously worked in Finance in the City and had received a very generous redundancy package when the Corporation was downsizing. Simon was 5 years her junior, he had a boyish look and easily passed for someone in their early 20s. They had met when Simon was working, as a waiter whilst he attempted to raise funds for his acting career –well he aspired to have an acting career – the truth was he was having difficulties in even obtaining auditions. Anyway there he was serving drinks to Jenny and her friends in a bar in central London when he felt someone pinch his bottom. He ignored it at first until Jenny did it again, only this time harder and announced, to the mirth of her friends, “they may be small girls, but he’s got buns of steel”. Simon could only blush as Jenny stated into his eyes and smirked. Strangely, embarrassed though he was, he was exited too and found himself somewhat aroused. He’d avoided that table for the rest of the evening, too embarrassed to approach. But as the evening drew to a close Jenny approached him at the bar and proffered an apology for embarrassing him. Simon had stammered a reply along the lines of it was nothing and that he enjoyed a bit of horseplay. He could feel Jenny eyeing up, in fact it felt like she was beginning to flirt with him causing him to blush again. Jenny just loved making Simon blush and it was on impulse she reached into her purse and handed Simon her card.
“That’s my number – call me Sunday afternoon - understand?”
Simon looked at the card and read the name, and looked at Jenny, somewhat surprised at her assertiveness. He mumbled an “Ok”
Jenny smiled at him and replied, “If you don’t call me I’ll come back here, pull your pants and pinch your bottom again – and that’s a promise!”
With that she turned and let the bar without looking back. If she had looked back she would have seen Simon flushed but mesmerised as his eyes followed Jenny as she strode out of the bar.
That was how they met. A whirlwind romance followed. They married, they moved out of London to the village, Jenny purchased the mail order business and Simon realised he wasn’t going to make it on the stage.
Simon had a secret though – a love of assertive woman was only part of it. Simon had, for as long as he could remember, enjoyed dressing up as a little girl. He loved stories he found on the internet of men and boys forced to don such childish clothes and being humiliated and laughed at. He had, over the years acc-umulated a stash of suitable clothes – frilly panties, lacy tights, a couple of dresses and petticoats. He had been free to indulge himself before his marriage to Jenny. Indeed he had told himself that when he married he would put such fantasies behind him and dispose of his stash, but he found it impossible to do And whilst he might go several weeks without dressing up if Jenny ever went out for the day – or went to visit her mother in the north, Simon would succ-umb to his urges.
And so, until the fateful day, Simon led a bit of a double life deceiving Jenny as to his true nature. That’s how Jenny described it when she told her mother about Simon’s shameful interest. And it is not quite accurate that Jenny was deceived up to that fateful day. To be honest there was a period of about 10 days when Jenny unearthed the truth about Simon, but Simon was in blissful ignorance that Jenny knew.
It all happened because of the credit card. When she got the statement she didn’t recognise the transaction. A couple of call to the Card Company and Pay Pal led her to the “Sissy Heaven” web page. There was no mistaking what they sold. She found the phone number and called quoting the credit card number and asking when the item had been delivered. She was able to discover not only the exact “little girl” dress but also Simon’s secret post office box. Was Jenny shocked? A little, but she thought to herself that this wasn’t totally unexpected when she came to think about it – there had been tell tale signs now and then and that, if she played her cards right, she might find the whole thing worked to her advantage.
Jenny’s next step was to call an old acquaintance from her Finance days who was an expert in IT. Sending Simon off for the day on a fools errand, the IT specialist caught a train to the village, inspected Simon’s computer and very quickly gave Jenny a print out of the websites Simon was visiting together with the password for his various memberships.
When the expert left Jenny spent a good 3 hours surfing a multitude of Sissy themed sites learning more and more about Simon’s dark and dirty little “secret”.
“Knowledge is power” as the saying goes. Now that Jenny knew, she intended to put it to good use. As she drummed her immaculately manicured red nails on the table a plan began to take shape in her head.
The next weekend was fast approaching. On Simon’s return Jenny greeted him warmly and informed him that her mother had called whilst he was out and that sadly she was going to have to visit her as she had taken ill.
“I know you don’t really care for Mummy” Jenny said in a very understanding way “so why don’t you stay here on your own? You’ll have much more fun than coming with me”.
It was true that Simon didn’t really get on with his mother-in-law, Elizabeth. It was from Elizabeth that Jenny had got the assertive nature. And Elizabeth had not really approved of Simon. She had hoped that Jenny would meet and marry a successful “City” type and giver her grandchildren. Instead Jenny had married a failed actor who, after 5 years of marriage had failed to father a child. And Jenny wasn’t getting any younger!
Simon of course was inwardly delighted at the thought of the weekend to himself and the chance to play “dress up” but, calling on his acting background he responded “oh no – I couldn’t possibly let you travel all that way on your own!”
Fortunately for Simon, Jenny was insistent. And so it was, on Saturday morning he stood on the driveway to their cottage and waved farewell to Jenny as she drove off for the weekend.
How long did Simon wait before retrieving his stash of clothing and dressing himself in all his frills? Perhaps half an hour at most. He was mindful that Jenny might have forgotten something and return for it. After half an hour, when she hadn’t return he felt himself safe. How wrong he was! For Jenny wasn’t visiting her mother – her mother was visiting Jenny! And whilst Simon was dressed in his best frillies sitting at his computer logging into various sissy sites Jenny was waiting at the station for her mother to arrive. And when Elizabeth did arrive a porter carrying two rather large suitcases accompanied her. After tipping the porter Jenny kissed her mother and remarked, “I see you brought them – did they all arrive?”
“Yes” replied Elizabeth “and whilst they cost a pretty packet I must say they are quite beautiful – I can’t wait to see them on, we’ll have to have a proper fashion show”.
Jenny and her mother had spent the last week on the internet sourcing and selecting a complete wardrobe of little girl sissy clothes.
“I must say I am looking forward to this,” announced Elizabeth
Jenny laughed “well lets just go and get something to east and let our little “girl” enjoy herself until we surprise her”.
Was Simon surprised a couple of hours later when Jenny quietly let herself and Elizabeth into the cottage? Surprised, yes – mortified too. It wasn’t a just a case of being caught with a hand in the cookie jar – it was, as Jenny would later tell her friends, more like a case of being caught with your hand in your frilly panties! a line that never failed to cause a roar of laughter to the listeners.
Simon’s initial reaction was to try and bluff his way out – he claimed that he was practicing for an amateur dramatic society that he was going to audition for. He thought he might have got away with it because Elizabeth and Jenny were in fits of laughter – it never occurred to him to ask what they were doing back at the cottage. When Jenny was able to speak she exploded Simon’s hopes that he got away with it.
“What’s the part Simon? A sissy? That’s a part you can play very well, isn’t it? It’s a part you have been practising for quite some time I think and hiding it from me.”
Jenny turned to her mother “What do you think Mummy? Do you think that if Simon wants to play the sissy he should be allowed too? “
Elizabeth knew her part “Oh I think if Simon wants to dress up and play a sissy girly then he should have his wish come true.
Simon could only stare at his wife and mother-in-law whilst they smiled in amusement at his predicament. With his heart thumping and his knees turning to jelly Jenny picked up her phone and began to film Simon in all his discomfort. It was at that moment that Simon, gripped with fear and embarrassment, wet himself. As a wet patch formed in his panties and began to flow down his legs Elizabeth folded her arms and stared at Simon in a “no nonsense” way loudly tut tutting in a disapproving manner.
Jenny announced “looks like my little girl needs to go back into nappies – but first I think she needs her a good hot red bottom for telling lies to her Mummy, don’t you think.
Elizabeth’s response of “that is so true” sealed Simon’s fate.
And that is how it all started.