Miss Elaine's Fantasy Fulfilled

by Roberto Alcazar

  Miss Elaine's

  Fantasy Fulfilled

  By

  ALCAZAR

  Copyright 2015

  Published by Alcazar at Smashwords

  Smashwords Edition, License Notes

  This ebook is licensed for your personal enjoyment only.

  This ebook may not be re-sold

  or given away to other people. If you would like to share this book with another person,

  please purchase an additional copy for each recipient.

  If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to yourfavorite ebook retailer and purchase your own copy.

  Thank you for respecting the hard work of this author.

  This is a work of fiction. Names, places, characters and incidents either are the product of the author’s imagination or are used fictitiously, and any resemblance to any actual person, living or dead, events, or locales is entirely coincidental.

  Any people depicted in stock imagery are models and such images are being used for illustrative purposes only.

  Revision date: 05/01/2015

  'You're late, Elaine!'

  'I am sorry, Mistress. I was delayed at work. And I had to dress and make up...'

  'Spare me the excuses, you stupid slut! You know I don't tolerate being kept waiting. You will be punished for this!'

  'But Mistress...' he started to protest but she cut him short.

  'Take off that blouse!'

  With quivering fingers he tried to take off the blouse but his long artificial nails slipped on the little buttons. Somehow he succeeded and he carefully hung the blouse over the back of a chair.

  'Take off that skirt as well!'

  He stepped out of his skirt and stood motionless, now only clad in a black, lacy 'open' bra that showed his nipples and a tight, padded girdle that rounded out his hips to create a more feminine figure. His legs were clad in black nylons held up by frilly garters. Red patent leather shoes with six inch heels were on his feet. And wide leather cuffs were locked just above his ankles connected by a short, chromium plated steel chain.

  'Sit down!'

  He tried to sit down sat down gracefully behind his laptop, in full view of the webcam.

  After a silence his Mistress spoke again. 'For being late tonight you will get punishment number two!'

  Groaning inwardly he closed his eyes for a moment.

  'Come on, go and do it!'

  'Yes Mistress.'

  He opened a desk drawer and took out a large butt-plug and a pair of weighted nipple clamps. The jaws of these wicked looking clamps were shielded with black protective plastic covers. Each one was about 3 inches long and contained a vibrator.

  'Take the covers off!'

  'But Mistress...'

  'Take them off, I said!'

  With some effort he took the plastic covers off. The sharp serrated jaws glittered malignantly in the subdued light of his bedroom.

  'Put them on!'

  Holding his breath he counted to three. With closed eyes he clasped the first clamp on his left nipple. The wicked steel teeth bit into the tender flesh and the sharp pain made him gasp. With clenched teeth he closed the second clamp on his right nipple. His fists gripped the armrests of his chair in a reflexive reaction to the burning pain radiating from his chest.

  'Switch them on!'

  His hands shook when he switched the vibrators on. The pain increased with every move he made and he closed his eyes for a moment.

  'Now the buttplug!'

  Obediently he applied some lube to the buttplug and then stood it on the chair in front of his webcam. He pulled his black lace slip down and slowly lowered his bottom onto the buttplug. With a groan he pushed it all the way in.

  'Now look at me and start jerking off!'

  His 17 inch screen showed his Mistress reclining on a couch in front of her webcam, spreading her nyloned legs wide apart. She moved her hips lasciviously while her long-nailed fingers played with her pussy and clit. 'Jerk off Elaine, jerk off... I want to see you cum...' she commanded in her low, husky voice.

  His Mistress' tantalizing masturbating image and her husky voice made his erection even harder. He started to ride the butt plug to feel it move deep inside him while the vibrating clamps sent waves of pain through his nipples and nearly drove him mad. Faster and faster his right hand went up and down his hard cock. As he wildly rode the butt plug the heavy nippleclamps danced up and down, their sharp teeth painfully tearing at his nipples. Gasping he closed his eyes and gave himself over to the painful sensations that shot through his body. Faster and faster he jerked until he suddenly uttered a low wailing moan as a jet of cum squirted from his cock.

  He fell gasping and sweating to the floor. A few moments later the voice from the laptop said 'Get up and let me see you take them off!'

  Slowly and painfully he rose onto his knees. He removed the buttplug and, lenching his teeth, took the clamps off. The returning blood shot through his tortured nipples, sending new flames of pain through his upper body.

  She said harshly 'This will teach you always to be on time!'

  'Yes Mistress, thank you for the lesson, Mistress.'

  'Be online at the same time tomorrow and ON Time Elaine! Do you understand?'

  'Yes Mistress!'

  The webcam image vanished abruptly.

  Too sore and exhausted to get out of his lingerie, he wrapped a red silk dressing gown tightly around his body. With a shaking hand he poured a stiff drink and let himself down in an easy chair. As he raised the glass to his lips, the chain between his ankle cuffs tinkled faintly. He looked at his nyloned legs and the high-heeled patent leather pumps with their ankle straps and suddenly he was aware of how totally enslaved he had become. A feeling of helplessness, bordering on despair came over him and as he took a big gulp of his drink, his thoughts drifted back to how it all had started, long ago...

  ...It had been that girl next door! He had been playing with her in the attic. She had dressed him in women's clothes and put him in a pair of high heeled shoes. Then, as a part of the play, she had tied him up. Helplessly tied to the bed, his head had swirled and he had felt a strange excitement that seemed to throb between his legs.

  ...After that first experience, women's undergarments had always held an irresistible attraction for him. He had felt his young cock grow hard whenever he saw his mother putting on her nylons. At that moment she somehow seemed to radiate femininity and sexuality. Watching her furtively he had fantasized about wearing black lingerie and lying in her arms while she softly stroked his hard young cock. His young hormones would soon be running wild and he had to slink off to the bathroom...

  ...Whenever he was home alone he had gone into his mother's bedroom. After dressing up in her lingerie and nylon stockings he had tottered around, trying to walk seductively in her stiletto heels. And when the silky feeling of nylon stockings sliding over his legs became too much, he would sit in front of her make-up mirror and slowly masturbate…

  ...It all came to an end after graduation when he had found a job out of town. He had moved into his own apartment and crossdressing was a thing of the past, he thought...

  ...Then, one day, his mother had called and asked him to help clear out the apartment of a female relative who had been killed in a car accident. It was a dreary business. Various family members had come and carried off all and sundry. Finally, late in the afternoon, the apartment was nearly empty. The only remaining items were several boxes of clothing and garments that nobody wanted. His mother had asked 'Be a dear and drop that lot off at the Salvation Army downtown. There's much they can use.'

  And with a grin she had a
dded 'unless you like to have some of it...' He had not liked the knowing look in her eyes and protested vigorously and had told her he would drop the boxes off immediately.

  ... Of course he had taken the boxes straight to his apartment. With a bouncing heart he had opened them and had been taken aback by the bewildering amount of nylons, girdles and corsets, skirts and dresses. One box was completely filled with sexy high heeled shoes and to his excitement he discovered they fitted him quite well.

  ...He soon became a weekend travestite. Every Saturday afternoon he would take a long and luxuriously scented bath. Then he would put on a girdle, bra, stockings and high heeled shoes. After applying his make-up he would slip into a dress or a skirt and blouse. To complete his transformation he would wear a wig, some jewellery and a pair of large, round-rimmed reading glasses.

  ...He started to read illustrated TS/TV stories. Or watch a tranny video, softly stroking his hard cock through the thin fabric of his skirt and lingerie He usually ended his weekend sessions browsing TS/TV internet sites, occasionally chatting on web cam with other trannies while calling himself 'Miss Elaine' and daintily sitting at his laptop, his nyloned legs close together.

  As with all exciting things, after a while the novelty wore off and he felt he needed an extra stimulus. But what could that be? Get a TV date? Oh, no! The idea of another man touching him, kissing him, holding his cock, made him shiver.

  It HAD to be a woman...

  Browsing the internet he stumbled upon a website called 'MILF dominated Trannies'; he excitedly browsed the site and watched the videos, his fantasy went wild. One video showed a helplessly bound crossdressed youth being dominated by a mature woman. Rubbing his nyloned legs together and pressing his girdle against his hard cock, he fantasized how it would feel to be dominated by an attractive, mature woman... How it would feel to be dressed in her clothes and to be made up and taken out shopping... How it would feel when she tied and gagged him? To be totally in her power and to be forced to kneel in front of her and lick her nylon clad legs. The fantasy started to grow on his mind until it finally started to dominate his thinking. He had to find a mature Mistress...

  "Mistress Monica speaking!" said a low, sexy voice.

  'Mistress, this is Miss Elaine. I had a look at your website and I was wondering...'

  'Yes?'

  'If you would have time for me...'

  'Before I say yes or no, I first want to have a look at you, do you understand?'

  'Yes Mistress.'

  ‘And that means you first have to present yourself on webcam.’

  'Yes Mistress!'

  'Have you read the conditions?'

  'Yes Mistress.

  ‘And you agree?’

  ‘Yes Mistress.’

  'Right; then I'll give you a five minute chance tonight at 10 pm. Make sure you’re properly dressed and made up! Otherwise you're not eligible!'

  'Yes Mistress!'

  'What's your name again?'

  Miss Elaine, Mistress!'

  'Be there at 10 sharp, Elaine!'

  'Yes Mistress, thank you Mistress!'

  At the end of that first webcam session Mistress Monica had grudgingly 'passed' him as one of her web-slaves. She had curtly told him to send money to an accommodation address before she would look at him online. A few days later, after receiving his three months’ payment in advance, she had sent him an e-mail summoning him online. There he first had been made to solemnly agree and to obey all of her whims and orders. And after he had agreed she had looked him over through his webcam.

  She had ordered changes in his makeup and dress and told him to wear long, artificial nails over the weekend. He had to dress according to her whims and to do as he was told. Sometimes she made him dress up as a whore and pose in various hooker stands. Or he had to dress up as a secretary and then to jerk off behind his desk while Mistress Monica watched him on webcam.

  And whatever she commanded, he had obeyed.

  The moment he finally had realized how enslaved he had become was the moment when she had told him to go and buy BDSM gear. And he later realized he just had gone and bought a collar and cuffs, chains and clamps. And he had done it all without comment...

  He had done so because he had become addicted to her; he could not envisage a weekend without her commands, without her domination...

  From then on, she slowly but surely had edged him towards the enjoyment of pain. She frequently told him to appear in front of his webcam as a collared and cuffed TV sex slave. She then would interrogate him and after finding even a minor infraction, he would be told to punish himself. And by doing so, she was slowly but surely turning him into a TS pain slave. A slave that longed for her domination and the pain filled orgasms she was giving him.

  Then, one Friday night, when he was again meekly kneeling in front of his webcam, there was an abrupt change.

  'I don't like that flat chest of yours, Elaine!' she had snarled.

  He had remained silent, as a well-trained slave should be.

  'I want you to look more feminine. You should have something in that blouse. And no rolled up stockings or pieces of foam plastic, it must look real!'

  He had often thought about fakes. But they were hideously expensive. What could he do? Lost in his thoughts he realized he'd missed what she said.

  'Excuse me Mistress, what did you say?'

  'I said I have a spare pair that you may use for a while until you can buy your own.'

  He was flabbergasted. She had never offered anything before.

  ‘Thank you Mistress. Yes that would be…’

  'And the next time I see you I want you to wear a chastity tube. You enjoy wanking too much. From now on the only time you can wank is when I permit it!'

  'But Mistress, I don't have one!'

  'Shut your mouth! I will send you one with the false boobs!' she snarled.

  He had hastily written down the accommodation address where he could pick the items up. It was not too far from his apartment.

  'Pick them up tomorrow and wait until I'm online. I will tell you what to do with them!'

  'Yes Mistress, thank you Mistress!'

  The accommodation address had turned out to be a seedy tobacconist whose shop window was plastered with advertisements for 'massage parlours' and 'Thai relaxation' and 'Escort services, female AND male'. An untidy looking old man had handed him a surprisingly heavy package. As soon as he was back in his apartment he untied and opened the package with quivering fingers. Two beautiful artificial breasts were lying neatly side by side, with a small bottle wrapped in plastic next to them. 'That must be a kind of glue' he thought. The other object was a curved steel tube with a lock. Attached to it were steel straps. They obviously had to be worn around the body and could be locked tight. A small, cellophane wrapped key was taped to the tube. And on top of it all was a post-it note saying 'Not to be handled without permission and supervision of Mrs Monica!'

  That Saturday evening he was on his knees in front of his webcam and Mistress Monica demanded 'Have you collected the items?'

  'Yes Mistress.'

  'Show them!'

  He grabbed the box and showed it, all contents still in their cellophane wrappings.

  'Good. Take off your clothes.'

  He stood naked in front of the webcam and listened to her instructions.

  'Now put that chastity tube over your dick before you get a hard on!'

  His penis shrank at the touch of the cold steel and it was easily inserted into the metal tube. A short steel belt went around his scrotum and a longer one around his waist. After he clicked the ends into the small Yale type lock she commanded:

  'See if you can pull it off!'

  He pulled hard, but the device was securely locked. Masturbation was impossible.

  'Good, keep it on while you put on the breasts.'

  Sitting in front of the make-up mirror and following her instructions he carefully glued the breast forms to his chest. When they were in place Mrs Monica
told him to get dressed in lingerie and come back.

  He hurriedly went to the bedroom where he had laid out a black lacy basque and stockings. After few minutes he was back and presented himself in front of his webcam. The basque was now nicely filled out by the breast forms and the shining tube in his crotch was covered by a black slip. He felt excited and aroused.

  'You look much better now!’ Mistress Monica purred. ‘Keep the tube and breasts on until tomorrow evening! That way you'll get used to them.'

  'Yes Mistress.'

  Sunday morning he turned over in is sleep and it felt as if sandbags were tugging at his chest. Only half awake, he reached upwards and touched a warm, yielding globe. Drowsily, he looked under the blanket and saw two firm silicone breasts jutting up. He touched one of the large nipples and a tingling sensation shot though his chest. The artificial nipple was connected to his own nipple by a tiny clamp and a kind of spring. As he played with the nipples, each and every touch of his finger was transmitted. The feeling aroused him and his cock started to swell. Then another, more painful sensation shot through his body. It was the chastity tube that encased his cock and made an erection painful.

  Sitting on the edge of the bed he thought about last night.

  As soon as Mrs Monica had gone offline he had stood in front of the hall mirror. He had hardly recognized the backlighted vision in the mirror. A nicely made up face, large breasts encased in black lace and shapely legs in black stockings. He absolutely looked more feminine than ever! Full of excitement he had walked around his apartment. With every step he took he could not help but being aware of the breasts. They were quite heavy and pulled at his skin. It was obvious he would have to wear a bra all the time.

  He closed his eyes and thought about that incredible, backlighted image he had seen last night in the full length mirror. Anxious to see how it would look in daylight he got up and dressed in lingerie again. After applying his make-up and wrapping a lacy, see-through gown around his body, he hurried in front of the mirror.