Whores And Pimps Ch. 01
Keywords: Whores, Pimps, Ch., And, 01,
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Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years but never anything serious; he kept himself to himself and rarely socialised outside of a small circle of colleagues and close friends he had cultivated over the years. Malcolm was boring really; but he one closely guarded secret. Malcolm was a crossdresser.
Once or twice a week Malcolm liked to lock all the doors of his modest two-bedroom suburban home, close all of the blinds, take the phone off the hook, and dress like a woman. It had started as nothing really serious; as a child he had liked to play with his older sister's panties and nylons; he loved the feel of the garments against his skin and occasionally he would wear his sister's underwear for an hour or two and then carefully place it back in the laundry basket. His fetish continued into his teens and when he finally left home and got a place of his own be bought his own panties, stockings and pantyhose and would spend the odd evening dressed in the silky articles.
Malcolm enjoyed his fetish alone and never talked about it to anyone, not even to whoever his current girlfriend might be at the time. Every now and again he was successful in talking a girlfriend into wearing stockings or pantyhose during sex and he loved the sensation of fucking her as she wrapped her nylon encased legs around his body; but it was not the same as wearing them himself. After a few years he also added petticoats, slips, suspender belts and other lingerie to his collection. Then the internet explosion happened.
Like most men Malcolm went searching for pornography on the net and concentrated on searching for sites which contained lingerie and hosiery fetish. Then one day he typed "men in pantyhose" into his web-browser and as he explored the matches to his search he came across a few sites dedicated to crossdressing. He followed the links further and further into the cyber-world of crossdressing and he was fascinated by it. He saw so many pictures of guys dressed not only in lingerie but fully dressed as women; wearing women's clothes, shoes, wigs and makeup. He became hooked.
Eventually he summoned up enough courage to acquire some clothes, makeup, shoes and a couple of wigs. He would buy the items whilst he was away on business; never in his home town; he was terrified of being caught. And so Malcolm went on year after year, dressing up once or twice a week, home alone and surfing the net where he entered chatrooms to chat on line with other closet crossdressers about all sorts of TG issues. He soon discovered that the world of the Transgendered was often confusing and mostly secretive. A few of the girls he chatted with on line were Transsexuals and wanted to live their lives as women. Some Crossdressers dressed so well that they could pass as women but were not at all interested in becoming women; they just loved to dress as women and sometimes they got together. They called themselves Transvestites and some of them met up to share their experiences or just to be in each other's company; some of them belonged to an organisation called the Seahorse Club. Other Transvestites met up to have sex with each other or with men. He discovered that the men who liked to have sex with Transvestites were called Admirers and they trolled the chatrooms and websites looking to arrange meetings. But most of his online friends were like him; for reasons many and varied, all they wanted to do, or most often all they could do, was to dress up at home and enjoy what they could of their fetish, alone or in the cold world of cyberspace. A lot of them were married men who kept their crossdressing activities secret or 'in the closet' as the colloquial term was known.
Yes it was a very exciting but confusing world out there in TG land and up until now Malcolm was content with his lot; he never dreamed of going out dressed as a woman and even though he sometimes fantasised about meeting other Crossdressers or Admirers he was too scared to do so. Malcolm was just too terrified of being caught; he was horrified of what the consequences might be if his colleagues and friends; or even worse his if his family found out about his secret. A couple of times he had summoned up the courage to wear pantyhose and panties to work under his male attire and even though it had thrilled him he had one bad incident which had scared him from ever doing that ever again.
Malcolm got on with everybody, especially everyone at work; he was friendly, cheerful, a good listener and worked hard. But there was one person there who just didn't like him. The guy's name was Eddie and he was the office jerk. If there was an office prank or someone was the butt of a practical joke, then you could pretty much guarantee that Eddie was behind it. He was annoying, but harmless enough and very productive; the bosses liked Eddie and turned a blind eye to his misgivings because he earned well for the company. In fact the only other manager whose department earned more than Eddie's was Malcolm's; maybe that's why Eddie was particularly vindictive to Malcolm with his petty practical jokes. Malcolm mostly ignored Eddie's jokes and snide comments but one day he let his guard down and paid a hefty price. One day Malcolm had gone to work one day wearing black sheer to the waist pantyhose and pink nylon panties under his business suit and was enjoying the thrill of being dressed that way secretly in public. On the rare occasions he went to work wearing pantyhose and panties he was very careful to make sure that his secret was safe; if he had to go to the toilet he would use the cubicles that had full length doors and when seated at his desk he checked every few minutes to ensure that his shirt remained tucked in, in the unlikely event that the waistband of his pantyhose or panties might show. This day he had to go pee and went to the men's room and locked himself in the end stall, contented that he could lower his trousers and do his business without being caught dressed in panties and hose. He hung his suit coat on the hook on the back of the cubicle door, lowered his pants and sat on the toilet seat with his panties and pantyhose bunched around his ankles. What he didn't know was that Eddie had followed Malcolm into the toilet to play a prank on him. Malcolm never found out what the prank was; all he ever knew was that it somehow involved Eddie standing on the toilet in the stall next to his and looking over into Malcolm's stall; maybe Eddie was going to throw a glass of water over him or something equally inane.
What did happen was that Malcolm heard snickering and looked up to see Eddies grinning face peering over the adjacent stall. Malcolm was horrified and just looked up slack jawed. Eddie just said,
"Nice underwear sweet-cheeks," and his face disappeared from view.
Malcolm spent the rest of the day, then the week, and then month in agony waiting for Eddie to torment him and ridicule him in front of his colleagues; he thought up ridiculous excuses as to why he might be dressed that way but the best he could come up with was that it was a bet; but with who? As it turned out Eddie never said anything to anyone else; he just occasionally sidled up to Malcolm and whispered,
"Are you wearing them today?" winked and walked away.
Eventually Malcolm decided that Eddie was too scared to bring up what had happened because he would have to explain his own actions; spying on a man doing his business in a toilet stall. Malcolm figured Eddie was content to just torment him occasionally with the question as to wether he was wearing female underwear to work. Malcolm never wore female underwear to work after that; he remained content to just play dress-up at home. Until one day..................
Every year on the anniversary of firm's founding, the bosses paid out for a big party; it had become a tradition. The party was fancy dress and it was held on the evening of the last working day before the Christmas break. Over the years it had become customary for the party to have a theme; and the theme had a twist. The twist was that whatever the theme was, the women dressed in the male or dominant role and the men dressed in the feminine or submissive role. One year it was 'cops and robbers'; where the women came along dressed as policemen or prison warders and the men arrived dressed as criminals or prisoners (lots of horizontal striped shirts and black masks that year; like the Beagle Boys in the Scrooge McDuck comics).
One year had been 'toffs and paupers'; lots of the women dressed in top hats and tails and the men dressed in the rags similar to the scallywags in Oliver Twist. There had been 'cowboys and Indians' (girl cowboys, boy Indians); 'heroes and villains' (girl heroes, boy villains); and last year, the best yet, had been 'knights and damsels' with the girls dressed as knights, valets and lords of the realm, and the men dressed as medieval princesses and ladies of the court. Everyone had a big laugh at that one, especially the men who had really got into the spirit of the thing with lots of them dressed up in drag in crinolines and ball gowns. It was a big laugh for everyone. Malcolm was tempted to dress up in his favourite lingerie, a ball gown, wig and makeup; but in the end had chickened out and came dressed as a court jester.
This year it was Malcolm's turn to choose the theme because he had been voted the worst dressed at last year's party. The judging panel had decided that his court jester's outfit was a copout on the theme and, as per tradition, the person voted worst dressed had to choose the theme for the following year. It was considered a task not to be taken lightly; the more outrageous the theme the more acclaim it received; and the person who chose an interesting and outrageous theme became the most popular man in the company; for at least a few months anyway.
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Keywords: Whores, Pimps, Ch., And, 01,