Whores and Pimps
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Ma/Ma, Consensual, NonConsensual, Reluctant, Rape, Coercion, Blackmail, Drunk/Drugged, BiSexual, Heterosexual, TransGender, CrossDressing, Incest, Brother, Sister, BDSM, DomSub, MaleDom, Spanking, Rough, Humiliation, Sadistic, Gang Bang, Group Sex, Oral Sex, Anal Sex, Masturbation, Petting, Sex Toys, Water Sports, Exhibitionism, Voyeurism, BBW, Foot Fetish, Leg Fetish, Prostitution,
Desc: Erotica Sex Story: Chapter 1 - Malcolm is the closet transvestite Michele who is yearning to come out of the closet and play. He organises the firm's fancy dress Xmas party using the theme "Whores & Pimps". The difference is that the men come as whores and the women as pimps. Michele gets blackmailed, seduced, raped and gang-banged as the night progresses. Then she goes home to tell her sister all about it only to find her sister has a penchant for trannys.
Malcolm was a middle manager with a small business in a large city. Malcolm led a pretty boring life; he was 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 became 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 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 looked up at Eddie 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 whether 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. Malcolm had wrestled with the decision as to what the theme for this year's party should be. Malcolm being Malcolm, everyone expected something boring like 'spacemen and aliens' or some other safe subject matter, but they were all surprised and delighted when in late November Malcolm posted the theme for this year's party on noticeboard. It was 'Whores and Pimps'.
Of course Malcolm had his own secret agenda; for years now he had wanted to go out in public dressed as a woman. Not like last year, dressed in a costume, but dressed in real women's clothing, fully made up and feminised. This was his big chance, and of course the more effort he made to be feminine the more he could justify it; after all, as the party's organiser it was expected that he would endeavour to dress up as realistic as possible in keeping with the spirit of the theme. The only concern he had was when he received an email from an anonymous address that simply said; 'I might have guessed', Malcolm was sure that Eddie had sent him the email but after a few days he pretty much forgotten about it.
Malcolm agonised for weeks as to how he could get away with dressing up as realistically as possible and to have a valid excuse as to why he looked so good dressed as a woman. Last year the men who had dressed as 'damsels' had looked pretty ordinary; sure they had hired great costumes, crinoline ball gowns, tiaras, ladies slippers and so forth; but most of them had five o'clock shadow and their makeup was garish and clown-like, their wigs were cheap facsimiles of real hair.
Then he had a brainwave; he would get his sister to dress him and make him up! He could answer any questions as to why he looked so good dressed as a woman truthfully; "My sister dressed me and made me up," and if anyone asked her, she would verify his claim. She would be his unwilling alibi.
Malcolm hit the chat rooms in the days leading up to the big party and all his online friends encouraged him and offered advice; everything from "Don't do it!" to "Go for it honey; stay out all night and pick up a nice man!" Malcolm was a little perturbed about that last remark because sometimes, when he home alone dressed as a woman, he fantasised about what it would be like to be with a man whilst he was feminised. He also hit lots of Transvestite web sites like TVChix, KTM, Crossdress World and so forth looking at pictures of Transvestites he admired to find the right 'look' for the party. He wanted to look slutty but not trashy; a sort of up market streetwalker. He found a lot of girls in the UK and Europe had mastered the look he wanted; that dark haired beauty Lyn in the UK had the look; so did Janet Petteflet in Holland, Wendy Stockings in Scotland, and Cherry in Melbourne Australia.
Malcolm finally made up his mind as to how he wanted to look for the party; and then he had a dilemma that he hadn't thought of before; one of his online girlfriends had asked him what fem name he was going to use. When he was online he just used the handle 'loves-to-dress' and because he had only ever dressed alone he and had never talked to anyone in the real world about his transvestism, there had never been a reason to have a fem name. It would be easy to think up some trashy name to use at the party; everyone wore nametags at the party and they were usually the same absurd double entendres you heard on bad British comedies. Names such as: 'Sir Shagsalot, ' 'Baron Ivor Bigun' and 'Princess Swallows' had been some of the more ridiculous names used by partygoers last year. He wanted a name that he could use at the party, and that he could keep forever as his own secret name for when he crossdressed. He thought about it for a few days and finally decided on a name.
He wanted a feminie first name close to his male first name, but not so close that it was obvious; and his crossdressing had originally started out as a fetish for panties and hosiery; so the name came to him in an inspiration. He played with the name Melanie for a while but decided that it was too close to his real male name. He settled on Michele; Michele with one L, because it was a little bit different. Malcolm decided his fem name would be Michele Nylons.
By the time the day of the party arrived, Malcolm had made all of the many arrangements required of him as the organiser. The venue was the small function room of one of the cheaper city hotels, the catering, drinks and entertainment were part of the venue's package; the firm paid for the party but they didn't lend themselves to extravagance; after all the party was really just an excuse to dress up stupidly, get drunk and let off steam. Also the firm's thirty or so employees preferred the venue to be at one of the cheaper hotels because, as most of them and their partners got drunk at the party, they usually rented hotel rooms at the venue.
The previous weekend Malcolm had called his sister on Friday evening and explained to her about the party and his need to dress up as a whore for the theme; he then went on to clarify why he needed to look as realistic as possible because he was the host and organiser it was expected oh him, and begged her for her help. He went on to say that he had some ideas as to how he wanted to look and that he had even got hold of some pictures off the internet to help him decide how he should look. As he had no idea how to dress like a woman she would have to help him. She eagerly agreed and was pleased that the normally quiet, reserved Malcolm was coming out of his shell for this event. She told him to bring along the pictures on Saturday morning and they would go shopping for everything they needed so that Malcolm would look as whore-like as possible; it would be fun!
When Saturday arrived Malcolm met his sister Angie in the city outside of a large department store. He had already figured out that he needed to behave naive when it came to world of women's clothing and makeup; but he was determined to ensure he got exactly the look he wanted; he would have to be cunning that's all.
"Hi Angie," he said, and kissed her cheek when she arrived outside of Myer; one of the better stores in town.
"Hi Malcolm," she responded.
"Let's get you feminised then, you hussy," she laughed, and Malcolm blushed; 'If only she knew the truth, ' he thought.
"Come on; lingerie first," she said enthusiastically and took his hand and led him into the store.
They made their way to the lingerie section of the store and started looking around.
"When you say you have to look as realistic as possible does that mean underwear too?" she asked.
"We can get away with some cheap foundation garments if you like; we can squeeze you into a cheap bra and you can just wear your own underwear under women's clothing if you like?" she added.
Malcolm was horrified at the prospect.
"No; definitely not!" he enthused, "If we are going to make me look like a hooker, then lets go all the way; I want to win best dressed and who knows how good some of the other guys will look; it can be quite competitive you know and it might come down to who is wearing the best knickers!" he laughed, hoping he hadn't gone to far and given his real motive away.
"Alright then; lets turn you into a complete slut," Angie giggled, "This is going to be fun!"
"My boring, unadventurous, brother is really getting into the swing of things. It's about time!" she added.
Angie led Malcolm to the brassiere section of the lingerie department and he pleaded ignorance as she expounded the various virtues of the different types of brassieres. They eventually settled on red satin full cup, size 14C.
"Red is definitely a whore's colour," she chuckled "and your panties should match; they usually have a matching panty for the better quality brassiere you know?"
"Do they really?" Malcolm responded feigning ignorance of such things.
"Here they are!" she quipped, delighted at having found the matching item on the rack of panties below the bras.
"Now I reckon any whore would love these," she laughed, "here; what do you think?" she asked holding a pair of red satin bikini panties up for him to see.
"How the fuck would I know Angie? And do you have to hold the fucking things up for everyone to see they're for me?" he pretended to be angry.
"Oh don't be silly Malcolm; if anyone asks we just tell them the truth. Besides you will have to try on some of the clothes anyway, at the moment I'm just guessing your sizes," she responded.
"You mean women have different sizes to men?" he quizzed. Malcolm knew exactly what size he was in women's clothes and shoes but he couldn't let on.
"Of course; at the moment I'm guessing your about a 14; a larger size for a woman even though you take a medium size in men's clothing."
"Ok," Malcolm tried to sound befuddled but she had nailed his size in one guess.
"Now if you want to look like a real whore then we had better get you some stockings; we can get stay-ups or we can get the type that require garters or a suspender belt; what do you think?"
"Definitely suspender belt!" Malcolm responded a little to eagerly.
Angie looked quizzically at her brother and he reddened.
"Angie; I'm a man so I have seen plenty of pictures of scantily clad women in my time and the sexy ones always wear suspenders and stockings," he responded.
"Suspenders and stockings it is then," she laughed.
"Oh I just love this one; and it matches the panties and bra," she said, reaching for, and then holding up a red lace garter belt with six long red suspender straps hanging from it.
They wondered over to the hosiery section and began to browse. Angie rummaged around and eventually held out a package to Malcolm. 'Sheer Fully-Fashioned Seamed Stockings by Kaiser" the label said. A little clear window in the package displayed that the stocking were black.
"Perfect," Angie said. "Whores always wear black stockings."
"Mmmm," she mused, "Show me your legs."
"What?" Malcolm responded caught unaware by the request.
"Show me your legs stupid," she repeated and reached down and pulled up one leg of Malcolm's pants up to his knee.
"Just as I thought; hairy! That will never do! Even though these stockings are black your hairy legs will show through; we'll have to get you some pantyhose to wear under them," she went on; dismissing Malcolm and rummaging again amongst the many packages of hosiery on the shelves.
"Just the thing!" She sounded delighted and flung another package at Malcolm.
This time the label said 'Kolotex Sheer To The Waist High Sheen Pantyhose.' 'Colour — Taupe'.
"Jeeze, I didn't realise it was so hard being a woman?" Malcolm laughed; again pretending ignorance but secretly pleased at all of the selections Angie had made so far.
"Ok buster; now comes the hard part; skirt and blouse." Angie went on and led Malcolm further into the store.
"Didn't you say you had some pictures?" Angie asked.
"Well I got these off the net," Malcolm said. "Apparently the women in the photos are really men; Transvestites I think they are called. They look realistic to me though."
"Malcolm; you are the dark horse; I never dreamed you would know about such things!" Angie looked shocked as Malcolm handed her the pictures.
"Well I never did know anything about this until I had to organise this fucking theme party!" Malcolm pretended to be angry again.
"I just entered a few keywords into my browser and these are some of the pictures that it came up with. And I'll tell you what; some of the other pictures were actually pornographic. Do you know there are some sickos out there that actually LIKE dressing as women?" he went on.
"Malcolm you have led a sheltered life haven't you," Angie answered but she was now too busy looking at skirts to carry the conversation on any further.
Angie looked at the pictures and looked at some skirts on a rack. She poked around for a while selecting items and then putting them back. Finally,
"Yes; this is it!" she squealed.
Angie held out a black leather miniskirt looking extremely pleased with herself.
"It's just like this one the girl; well man; well whatever; is wearing in this picture," she said; pointing to a picture of Janet Petteflet which Malcolm had downloaded from KTMGirls.com.
"Now for the awkward bit; you will have to try it on."
Malcolm paled; he hadn't though of that. He knew that he was usually a size 14 in a skirt but also knew that sizes varied; he had a couple of 12s and even a 16 at home.
"It's no good frowning and looking sorry for yourself. If you are going to spend all this money to dress up for one stupid party we at least better make sure the clothes are going to fit you." Angie scolded.
As it turned out it wasn't that difficult. Angie being Angie just went up to the floor supervisor and told her the truth; that Malcolm had to dress up in drag for a party. The supervisor, an attractive woman in her fifties, was only too delighted to help. She led them to a single fitting room that had a full-length door that was separate to the rest of the female fitting rooms.
"We keep this room for special clients and the handicapped; it's separate to the rest of the fitting rooms and very discreet. Just find me when you have made your selections and I'll see to you personally," the floor supervisor smiled.
"Right; now a blouse!" Angie went on and charged on through the women's clothing department to where there were what looked like thousands of blouses.
Malcolm was so glad that he had thought of using his sister as a ruse; she seemed so enthusiastic and was actually having fun selecting clothes for him. This was going a lot easier than he thought it would; he didn't have to explain what he wanted at all; Angie was taking the lead and selecting just what he would have chosen to wear himself.
"Finally!" Angie exclaimed holding up her prize after what seemed like eternity as she waded through a sea of blouses and tops.
It was a sheer nylon leopard-skin patterned, longsleeved blouse and it was perfect to go with the black leather miniskirt.
"Right lets get you sorted brother of mine; go and wait by the fitting room." Angie dictated and stormed off back towards the skirts.
A few minutes later Angie returned with the floor supervisor; her arms loaded with clothing.
"I've got the skirt and blouse in size fourteen and sixteen," she said "Try them on in there and make sure they fit properly; can you do that?"
"I know," she went on, "take this in with you and try to make sure you look as good as the girl in the photo," she said, handing him the picture of Janet Petteflet.
Malcolm went into the booth knowing that the size 14 skirt would be perfect; and it was. The size 14 blouse was too short in the sleeves and tight in the shoulders; the size 16 would have to do even though he would have preferred it to be tighter around the waist. Malcolm came out of the fitting room and handed his selections to Angie and the others to the floor supervisor. Angie wasted no time and dragged him over towards the footwear department.
"The fucking blouses button up the wrong way," Malcolm whined; again pretending ignorance in the matter of female attire.
"No they don't; men's shirts button up the wrong fucking way, you lummox," she quipped, and continued to drag him along by his sleeve.
When they got to the ladies footwear section it was blessedly easy. Angie went straight to a pair of black, patent leather, high-heeled sandals. Malcolm made a stupid gaffe as Angie looked at a size chart,
"Size ten," Malcolm said, not thinking of the consequences.
Angie spun around and looked him quizzically. Malcolm blushed a deep red and stammered,
"I read somewhere that women's sizes are two sizes smaller than men's. You know it's one of those bits of useless information you pick up," he offered as an explanation.
Angie continued to stare at him questioningly for a minute and then turned back to the rack of shoes and selected a pair of size tens.
"Here; try these," she said handing him the high heels.
"There's no one around, just try them on ok," she warned before Malcolm could offer a protest.
Malcolm sat on a stool and removed his loafers and socks and tried them on; a perfect fit.
"Lovely! I'll show you how to walk in them tomorrow Malcolm; you will find it difficult but no self respecting whore would wear anything except high heels," she laughed, regaining her previous joviality.
"Accessories and makeup next!" Angie charged ahead again.
"Accessories? Makeup?" Malcolm quizzed.
"Oh just go to the in-store coffee shop Malcolm and I'll meet you there later," she tried to feign anger but laughed.
Malcolm did as he was told and Angie joined him about twenty minutes later. Sipping on a latte she showed him what she had acquired in his absence. There was a slim gold belt with a silver buckle, a gold clutch purse, a selection of makeup (to which he showed absolute ignorance for sake of appearances), and what seemed to be far too much jewellery for one night's dress-up. They finished their coffee and took their selections to the checkout where thankfully Angie presented the purchases to the cashier and all Malcolm had to do was hand over the cash.
Angie again led the way and this time they stopped in hairdressing salon. Angie explained that it was her favourite salon. And the best hairdresser in town worked there.
"I could take you to a fancy-dress store and rent something tacky or we could go to a novelty shop and get one of those awful novelty wigs but you did say you wanted to look as feminine as possible so I'm afraid you will have to fork out for something good. On the bright side; if the wig looks good on me too I might buy it off you after the party," she said.
Angie took charge of the situation and entered into a deep discussion with one of the hairdressers whilst Malcolm stood there with his hands full of shopping bags trying not to look embarrassed. Eventually he was led into a small room at the back of the hairdressers where he was seated and introduced to Stephan, Angie's hairdresser. Angie and Stephen then seemed to have the time of their lives trying different wigs on Malcolm. They finally both agreed on one, and Stephan held up a mirror so that Malcolm could see. It was brunette with some lighter highlights; the hair was straight but curved slightly at the neck and fell to just on his shoulders; the fringe just covered his eyebrows. It was lovely but of course Malcolm just said,
"Well if you think its ok we'll take it" and paid up. He made a fuss about the price, secretly pleased that the wig was perfect for the shape of his face.
Outside the hairdressers they parted ways; Malcolm was disappointed when Angie took all the purchases from him,
"It's not as if you need them until next Friday is it? And as you are coming around my place to for me to dress you properly and make you up I might as well take them home," she said cheerfully, kissing him on the cheek and walking off towards where her car was parked.
"Thanks for all the help," Malcolm responded and walked away excited. He could hardly wait for next Friday.
All week the office was abuzz with talk of the party; many of the staff discussed how they were going to dress. Some were just going to squeeze into their wives clothes; some had gone to costume-hire specialists. The girls were having a great time rummaging out old flared purple pants, platform shoes and other outrageous seventies pimp apparel. Malcolm kept quiet despite the friendly ribbing that he copped from some of the staff; they joked that boring old Malcolm wouldn't know a whore from a boar or that he would probably come looking more like a washer woman than a prostitute after last year's feeble effort. The only quip that disturbed him was an aside from Eddie,
"She'll look gorgeous I'll bet."
Malcolm didn't know if Eddie was joking or being sarcastic but he didn't care; he was too excited and looking forward to the party for reasons that none of his colleagues could imagine; Michele was making her debut!
Friday afternoon finally came and Malcolm drove around to his sister's place in eager anticipation. The firm had finished work early and he had a few drinks after work with some of the staff and they had said cheery farewells until later that evening. He arrived at Angie's place as instructed at five o'clock having showered and shaved as close as possible ensuring his face was smooth and without a trace of stubble. He had a gin and tonic to steady his nerves before leaving home and Angie greeted him at the door with another.
"To help you relax dear brother," she laughed and led him through the house into her bedroom.
Angie had unwrapped all of last week's purchases and they were laid out on her bed; Malcolm got excited just looking at them and gulped down his drink. Angie went to fix him another.
"I've been thinking Malcolm; how serious are you about looking as feminine as possible?" she called from the lounge.
"I really want to win the prize Angie; I want to really make up for last year," he shouted back.
Angie returned with a drink for both of them.
"Well there is only one thing for it then," she said and reached into a draw in her dresser and held out a pink plastic object that looked like some sort of alien ray gun.
"It's my Lady Shaver," she responded to his quizzical look, "were shaving your legs ok?"
Malcolm was now a little drunk and laughed out loud,
"Well if that's what it takes Angie; let's do it!"
After a brief argument in which Angie explained that she had seen her younger brother naked when she bathed him as a child. She also went on to explain that in her eyes seeing a man in his briefs was no different to seeing a man in his swimming costume so Malcolm stripped down to his briefs and sat on the chair in front of the dressing table. Angie ran the shaver up and down his legs until they were hairless; this was achieved with much howling and complaining from Malcolm who was reminded by Angie that women had to suffer far worse to look good for men; as he was about to find out. She shaved the hair off his feet and toes and examined her handy work.
"You'll still have to wear the pantyhose I'm afraid; your legs are lily white and some of those varicose veins look like roadmaps. It's a trick I used when I was younger when I couldn't be bothered shaving my legs before a date; just wear two pairs of nylons," Angie explained.
"You're the boss," Malcolm chuckled and took another sip of his drink.
"Ok; sit still, keep quiet and just do as I say and we'll have you looking like a girl in no time," Angie laughed and moved in front of him and went to work.
She had quite an assortment of cosmetics laid out on the dressing table along with various sized brushes, sponges and applicators. Malcolm forced himself to relax and let Angie go to work. He had made himself up hundreds of times before but now he was going to be made up by an expert so he payed attention to every detail so that he could pick up any pointers.
First Angie patiently painted his finger and toenails; two coats of glossy plum red. She told him not to smudge the nail polish before it hardened and went on to explain how women often tried to match their nail polish with their lipstick.
Angie applied a thick coat of foundation to his face and neck and then set it with a liberal dusting of matching face powder. She then went to work on his eyes. Next she brushed dark blue eyeshadow onto Malcolm's eyelids working from the inner corner of each eye to the centre above her pupils. She worked the powder upwards right up to his eyebrows and then she applied a coat of lighter blue out to the far corners of his eyes, lightening the makeup as she worked it up to his brows and blending the two shades where they merged.
"I'm no expert at hooker makeup," she said, "but I've seen enough movies to know that usually go for these garish colours.
"Whatever," Malcolm said pretending to feign interest whilst paying close attention.
Angie tut-tutted a little and reached for some pink eyeshadow and applied it liberally around the edges of the two coats of blue that she had already applied; blending the eyeshadow with a small brush and making final adjustments with her fingertip. Malcolm loved the effect and filed the snippet away for future use.
"Ok brother; keep very still now and just close your eyes half-closed for me; here comes the hard bit; the eyeliner." She said, concentrating on her task.
Angie applied jet-black eyeliner to his upper and lower eyelids as close to his lash-line as possible. She started in the very corner of her each eye and worked outwards applying three coats and touching up where necessary so that his eyes were framed by the black makeup.
"Open your eyes; lift your head up but look down at my tummy and keep still for me sweets ok; I'm going to do your mascara next. I hope you are taking mental notes so that you can touch up your makeup during the evening." Angie said.
"What do you mean; touch up my makeup?" he asked; knowing full well what she meant.
"We girls don't stay looking good all night without touching up our war-paint you know" she giggled, "that's why we spend so much time in the john; why do you think we call it the powder room! This makeup that I bought you yesterday, you can take with you tonight; you can give it to me after the party as you won't be needing it," she explained.
She applied plenty of thick black mascara to his upper and lower eyelashes; fiddling a little as she worked. She explained that as his eyelashes were very fine she had to apply lots of the product to get a good effect,
"I wish we had bought falsies," she muttered.
Malcolm laughed inside because he had three sets of false eyelashes at home.
"Ok nearly there," she sighed and took a sip of her drink.
Angie applied blusher to his cheeks, feathering it along his cheek-line and smoothing it up so that it almost merged with his eyeshadow. Then she dusted his whole face and neck with a coating of sheer-glow finishing powder, being careful not to smudge her mascara and eyeliner.
"Ok Malcolm I want you to play particular attention to how I do your lipstick; you will definitely have to touch up your lippy tonight," she lectured.
She opened a long slim box that contained two thin tubes and unscrewed the first tube to reveal an applicator coated with plum coloured liquid lipstick.
"This is the first coat and it is long lasting colour lip-gloss; be careful how you use it honey because it is really hard to get it off if you fuck it up ok?" she instructed, "so pay complete attention and when you touch it up tonight make sure you don't go outside of the lip-line that I put on you."
Malcolm had never used a two-coat lipstick before; he just used ordinary cheap lipstick at home and he paid very close attention as Angie coloured his lips with the first coat of colour and then took the other tube which she screwed at the bottom to reveal what looked more like the lippy he was used to, but it was slimmer and it was transparent not coloured. She waited a minute and then applied the clear top coat over the base colour coat.
"Perfect," she whispered more to herself than him, "now leave your lips parted for a second until it's dry ok?"
Angie took the brunette wig off the wig stand and brushed it out while Malcolm sat still and let his makeup set and lipstick dry. After a minute or two Angie put the wig on his head and fiddled with it until it was sitting perfect with the fringe straight. She brushed it here and there and then stood back to admire her work.
"You look stunning; take a look," she said, pointing to the mirror.
The transformation was astounding; from a plain, smooth-faced man he had become a heavily made-up middle-aged whore. Her brunette fringe framed her dark exotic eyes and her bangs caressed her rouged cheeks and highlighted her luscious red mouth. Malcolm now started to think of himself as Michele the whore; not as Malcolm, the boring manager of a small department in a small business. 'From now on, for the rest of tonight, I AM Michele!' she convinced herself.
"Ok let's get you dressed then," Angie said.
"You can have a quick drink and get into your pantyhose and knickers you hussy," she laughed, playfully kissing his cheek.
"I'll step out and freshen our drinks while you do that I think; I don't want to see your wiggly bits," she laughed, "put the pantyhose on first then the panties over them ok? You've seen one of your girlfriends put on pantyhose I take it? You don't need my advice," she joked; then added as she walked out the door, "don't ladder the fucking things!"
Michele sat on the edge of Angie's queen size bed and kicked off her men's briefs; they now seemed ugly and inappropriate for a lovely whore like her. She eased the pantyhose from the slim packet and slipped the hosiery over her pretty painted toes and slid the sheer nylon up her feet one foot at a time. She carefully eased the pantyhose up her legs keeping the nylon taught; smoothing out the wrinkles as she went. She stood up and pulled the waistband of the pantyhose up over her crotch and smoothed the nylon gusset around her midriff to just below her bellybutton. She slid the red satin bikini panties up her nyloned legs and pulled them snug around her buttocks and crotch. Michele felt the beginnings of an erection and nearly panicked; but then the though of her sister finding her aroused soon made it go away.
"Ready sis;" Michele called through the door.
"Oh lovely," Angie joked as she came back into the bedroom with two more gin and tonics.
"Ok let's get a move on, I don't want you to be late for your own party," she said in determined tone.
"Stand up and just do as I say buster," she joked; but in a tone that bore no argument.
Angie took the red lace suspender belt and adjusted it so that it sat tightly around Michele's waist and so that the top of garment covered the waistband of the pantyhose. Next she knelt down and drew the diaphanous black nylon stockings up Michele's legs one at a time; the stockings sighed their nylon on nylon whisper as they glided over her pantyhosed legs. Angie carefully adjusted the back-seams so they lay straight and centred along the back of Michele's legs and then clipped the garters hanging from the suspender-belt to the reinforced stocking tops. As Angie smoothed the nylons along her legs Michele suppressed the shiver of excitement and felt a little uneasy about experiencing such emotions; especially with her sister's face so close to her sex organs. Michele swallowed and tried not to think too much into it.
Next Angie hooked the brassiere around Michele's chest and settled the cups into the right position; she walked over to a drawer and took out several pairs of old pantyhose which she stuffed into the cups of the bra to fill them. Then she had Michele step into the black leather mini which she pulled at and played with until it was adjusted nicely at the waist and the hem was nice and straight at mid thigh; she left it unzipped for now. Angie handed Michele the leopard-skin nylon blouse to put on while she went to the dresser and took a drink. She gave Michele a sip of her own drink and put the glass down on the table. Michele noticed that she had not left any lipstick on the rim of the glass as she often did when she was dressed at home. 'That two-coat lipstick really works, ' she thought pretending to struggle with the buttons because they were on the opposite side to men's shirts. Angie came over and finished buttoning the blouse and tucked it into Michele's skirt and zipped it up. She buckled the slim gold belt around Michele's waist and adjusted it so that it sat nicely.
"Nearly there; just jewellery and shoes to go" she sighed.
Angie opened the packet which contained the cheap costume jewellery that she had bought for her brother last week. She clipped silver mounted ruby drops to Michele's ears and hung a matching silver and ruby necklace around her neck and matching bracelets on both of her wrists. She put on four large silver rings, two on the fingers of each hand; the rings were set with emeralds and rubies.
Angie sat Michele back on the bed and slid her feet into the black leather high-heeled sandals; buckling the thin straps which came to just above Michele's ankles.
"Now for fuck sake be careful when you walk in these Malcolm," Angie said; " lean a little backward and make sure you come down on the balls of your feet first, not the heels, when you walk. It will take some practice but it's only for one night. You should know what we girls have to put with when we wear those fucking death traps anyway," she chided playfully.
Finally Angie fastened a silver anklet below Michele's left ankle; another fake ruby glittered as it hung from the thin silver chain fastened to the anklet.
"You're done honey; take a look in the mirror," Angie said and helped Michele to her feet. Michele stood up and walked over to the mirror and looked at herself.
She looked stunning; the best she had ever looked dressed as a woman. She had just the look she wanted; in her mind she decided the look was to be called 'London streetwalker' because she looked just like the English prostitutes she saw in the TV shows. Michele walked over to her sister and kissed her on the cheek and said,
"Thanks Angie; you are a doll. Oh! One more thing; pin this on for me will you?"
She handed Angie a large white name bar embossed with the firm's logo in one corner and a Christmas tree in the other; in gold pen script in the centre of the name bar was written: MICHELE NYLONS. Angie pinned the badge to Michele's left breast.
"Michele Nylons; cute name," Angie said.
"Ok Malcolm; err I mean Michele; lets do the last finishing touch."
Angie went to her dresser and took a small bottle of the cologne 'Poison' and sprayed a liberal amount of the perfume on Michele's neck and décolletage; then she reached down and playfully sprayed under Michele's skirt and on her thighs.
"Just in case you get lucky honey," Angie teased.
Michele blushed a deep red,
"Fuck off Angie!" Michele responded a little hurt.
"Don't be such a girl Malcolm; here take this," she said dropping the small bottle of 'Poison' into the small gold clutch purse that they had purchased last Friday and holding it out.
"The purse has got powder, eyeshadow, mascara, eyeliner, blush, and lippy in there sweety; so you can touch up your makeup as you need to. There's also a hairbrush; everything an old whore needs to ply her trade," she laughed.
Michele stepped forward and took the purse from her sister and bent to kiss her chastely on the lips to bid farewell. Angie shocked Michele by pulling her into a tight embrace and kissing her, closed mouth but forcefully, on the lips; then Angie astonished Michele completely by sliding her hand under Michele's skirt and gently stroking her manhood through her panties. Angie whispered into Michele's ear,
"I know about you, you know!"
Michele pushed her sister away and looking absolutely stunned; she gasped,
"What do you mean; you know!"
"Oh Malcolm; I mean Michele. I've suspected since we were kids. All the times I found my nylons and panties dishevelled and stained; who else could it have been? One day I even saw you putting a pair of my pantyhose in your pocket as you left the bathroom." Angie explained in a soothing voice.
"And last week you knew your ladies shoe size; you insisted on wearing a suspender belt; you had those pictures of Transvestites; and you pretended not know that blouses button on the opposite side to a shirt. You sat uncomplaining while I put on your makeup; but the real give away was the way you walk in those high heels honey. It took me fucking months to master high heels when I was a teenager; and you glide around my bedroom like you were born wearing the fucking things!" Angie finished.
"It's nothing to be ashamed of; your secret is safe with me. And you look positively gorgeous; if you weren't my brother I'd fuck your brains out; now get the fuck out here and go and enjoy yourself before I throw you on my bed and ravage you." Angie pushed Michele towards the bedroom door.
Michele was stunned but accepted what she had just heard and realised that she had been stupid to think that she could get away with using her sister to help her crossdress and still keep her secret. In hindsight Michele knew that she would slip up some how. Then a question lanced into her head; 'What did Angie mean about ravaging her? And what the fuck was that passionate kiss and quick fondle all about?'
"Angie; are you a lesbian or something?" Michele asked her sister as they walked to the front door.
"I'm an 'or something' ok; but that's a conversation for another day; now get the fuck out of my house and party til you drop bitch! Oh; and come around for coffee tomorrow afternoon and tell me all about it!" she laughed and pushed Michele out of the door and into the night air.
Michele walked over to her car, stunned at what had just happened; even though she had lost count of the number of gin and tonics she had drunk over the last few hours she now felt completely sober. She dropped in behind the wheel and her skirt rode up revealing her stocking tops; she smoothed down her skirt and slid her hands along her stockinged thighs and sighed with desire at the feel of her feminine attire.
Michele smiled to herself and drove off into the night trying to get her head around the last few minutes. Eventually she settled down enough to realise that she had been particularly stupid drinking so much alcohol with a three quarter of an hour drive ahead of her from the suburbs to the city; the police were ruthless when it came to alcohol breath testing during the festive season. She decided to use a little used back road that bypassed most of highway into town; it would put an extra twenty minutes or so onto her journey but she was better safe than sorry.
After she had driven a few kilometres down the dark road she realised that the effects of the drinks she had imbibed earlier had far from worn off; she had to really concentrate and to make matters worse she had never considered the difficulties of driving a car whilst wearing high heels.
Michele checked her mirrors and then reached down and attempted to unbuckle her right shoe so that she could better control the brake and accelerator. It was a huge mistake; as she struggled with the buckle on her high heel her car swerved violently to the right and she had to correct the vehicle quite quickly on the dark narrow road. As she gained control of the car and was congratulating herself for avoiding disaster she saw blue and red flashing lights in her rear vision mirror.
"Fuck!" she exclaimed, and pulled her car over into a darkened rest area at the side of the road.
She followed the small dirt track to series of marked parking bays behind a darkened toilet block and pulled into one of the spaces; she looked around and saw that the rest area was deserted except for her own car and the police cruiser that had now pulled up beside her. A fat policeman squeezed from behind the wheel of the police car, turned on a large black torch and sauntered over to her driver's side window; Michele wound down the window terrified. She didn't know wether to be more worried about being out dressed up in drag or being over the prescribed alcohol limit. The fat policeman shined his torch on her face, smiled and said,
"You were all over the road back there miss; have you been drinking?"
Michele summoned up all of her courage and answered,
"I had a couple of drinks an hour ago officer but I'm sure I'm under the limit; I swerved to avoid a small animal on the road," she lied.
The policeman looked at her for a nearly a full minute shining his torch inside the car and up and down her body and back to her face.
"Jesus Christ you're a fucking guy aren't you?" he asked incredulously.
"Yes officer; let me explain..." and Michele went on to explain that she was dressed in drag to attend a theme party at work.
After listening to her story for a few minutes the officer cut her short.
"Well that may be sir, ma'am; whatever. But I still think that you are under the influence of alcohol and I intend to issue you with a roadside breath test." He said and waddled back to the cruiser and returned with an alcometer.
He pushed it through the window in front of Michele's face and said,
"Put your lips on the tube and blow; words I'm sure you quite used to;" he added cruelly.
Michele did as she was told and heard the machine beep rapidly after a few seconds. She hung her head and contemplated what would happen next. She would be taken to the police station and have to suffer the indignity of waiting around for bail dressed up in drag. Undoubtedly the policemen at the station would ridicule and taunt her. Even worse; what if they put her in a holding cell? She had read about what happened to some young men in prison at the hands of jailhouse thugs; what chance would she have dressed as she was? Could she ask for protective custody? Her head was spinning.
The Policeman took the machine away from Michele's lips and looked at the reading and smirked.
"You're shit out of luck tonight sweety," the cop smiled evilly at Michele through the window.
He turned on his heels and wobbled back to his cruiser; 'He's calling it in or whatever they do!' Michele thought to herself. She was on the verge of sobbing. She looked across at the police cruiser and by the light of the dome light she saw the fat cop leaning inside talking on the radio. Then the flashing lights on the top of the police car went out, closely followed by the head and tail lights. The cop slammed the door and the rest area became hauntingly dark and deathly silent. Michele could just make out the dimmed glow of the policeman's torch as he returned to her car; as he approached she saw he was shading the light with his other hand. He leaned on the roof of her car and it lurched under his added weight.
"Look honey, I've dealt with your type before ok; you don't do thirty years on the force without dealing with the occasional trannie now and then. You are in all sorts of problems here; the reading on my little machine there says you're at least twice the legal limit to be driving."
"Now, we can sort this out one of two ways; you can accompany me to the police station, and I'm sure the ramifications of that option have crossed your pretty little mind; and also you will lose your license and cop a hefty fine. Plus I'm betting someone who drives a car like this has a job where a DUI will not be particularly welcomed," the fat cop droned on.
"Or I can get in the passenger seat there and we can settle this quickly, painlessly; and to both our advantages if you know what I mean?" he finished.
Michele was now totally confused; was there a way out of this? Was he asking her for a bribe? Thank god! There was a way out of this! All she had to do was let the cop get in passenger seat and she would hand him some cash and he would be gone. Yes; it made sense! He wanted to sit in the car so no one passing by could see her handing him the money; that's why he turned off his flashers and headlights.
"Well sure officer; get in and let's settle," Michele sighed, relieved.
The fat cop had trouble squeezing into Michele's small BMW but he finally got settled and closed the door. The dome light went out and Michele heard a rasping sound that she couldn't quite figure out. 'Of course he's opening the zipper of his wallet to hide the money, ' she concluded.
"Turn on the dome light honey; I want to see you do it," the cop said.
That made sense to Michele; he wanted to make sure he was giving her the right money; when you take bribes you have make sure the person paying the bribe isn't ripping you off. Michele turned the dome light on and turned her head towards the cop and started to say,
"How much?" when she glanced down and saw the policeman's stubby fat penis sticking out the front of his uniform trousers.
"Well I won't be long honey; I haven't had any for ages," the cop chuckled and reached out and pulled her head into his lap.
Michele was horrified; it finally dawned on her what he had been talking about all this time; she had completely misunderstood his intentions. These thoughts sped through her mind just as her lips came into contact with the man's fat smelly cock. Michele sputtered and tried to move her head but the heavy cop held her down.
"Suck it good babe; come on," he moaned; and he pushed down harder and Michele had no choice but to take the appendage into her mouth.
Michele sputtered and blubbered trying to spit the fetid member out of her mouth. Her efforts to get away from the cop's penis in fact stimulated the glans of his organ as Michele's lips and tongue lashed at the stubby little cock trying to spit it out. The cop pushed down so hard on her head that it hurt, and at the same time he pushed upwards, lifting his fat arse out of the seat; Michele had to open her mouth or choke and as she did the whole of the diminutive fat member slid inside her mouth and started to convulse and throb.
Michele gasped as a torrent of semen filled her mouth and then she started to gag.
"Don't you spit it out bitch!" the cop warned, holding her head down in his lap.
"Yeah baby that's it; swallow it; oh fuck you're good! Suck it baby; suck it! I'm coming; oh yeah," another stream of obscenities issued forth from the policeman as he ejaculated into Michele's mouth.
Michele was helpless; held over the cop's small throbbing cock as it continued to flood her mouth with sperm. She had no choice; Michele swallowed. The policeman's secretions were not actually that foul; they tasted musty and creamy. She sucked and swallowed knowing she had no choice.
"Ok baby; daddy's finished now; just lick it clean and I'll be on my way," the cop chuckled.
Michele realised the worst was over; she licked the fetid member clean and swallowed the last of the cop's secretions. The cop lifted Michele's head out of his lap and leaned over and kissed her full on the mouth before she had time to react.
"Thanks hun," he whispered in Michele's ear; then zipped his fly and struggled out of the passenger door. He walked away towards his police car and waved over his shoulder without glancing back,
"Drive careful now sweetheart," he shouted and climbed into the police car and drove away.
Michele sat there stunned; she couldn't believe what had just happened; not only had that fat smelly, little dick cop raped her mouth; she was rock hard in her panties. What the fuck was going on?
Ma/Fa / Fa/Fa / Ma/Ma / Consensual / NonConsensual / Reluctant / Rape / Coercion / Blackmail / Drunk/Drugged / BiSexual / Heterosexual / TransGender / CrossDressing / Incest / Brother / Sister / BDSM / DomSub / MaleDom / Spanking / Rough / Humiliation / Sadistic / Gang Bang / Group Sex / Oral Sex / Anal Sex / Masturbation / Petting / Sex Toys / Water Sports / Exhibitionism / Voyeurism / BBW / Foot Fetish / Leg Fetish / Prostitution /