Crystal's StorySite storysite.org
by Annalise Barker
"Hi Richard! Long time, no speak little brother!" exclaimed Natasha as her younger brother answered the phone. "Hi Nat. What are you up to at the moment? Working hard, or getting used to your life of leisure?" he replied cheekily.
"Youre a sarcastic so-and-so sometimes. Yes I am still working, but I guess you are kind of half right. Ive gone down to part-time at work; dont want to get bored with my new role as lady of leisure too quickly! Work is still pretty fun, so I might as well stay for the moment and enjoy it while it lasts. Hows your work going? Still keeping the girls dangling, you stud, you!?"
"Yeh, right! Think youre getting me mixed up with someone else," he replied. "And anyway, isnt it you whos always had the boys at your beck and call?"
"Hey bro youve either got it or you havent," she teased playfully. "So when are you coming down to see me next? Havent seen you in a while. I think its time you paid me a visit so I can check up on you and make sure you arent getting up to mischief. What are you up to weekend after next?"
"Im free as far as I can think that far ahead. Ill come down on Friday night if thats okay . Make a weekend of it."
"Sounds good. Let me know the time and Ill meet you at Euston station."
"Cool. Ill call you in the week then."
The siblings said their goodbyes and hung up.
Natasha was the elder of the two by three years. She had just passed her 29th birthday and Richard was 25. Both had gone to university after finishing school, but whereas Richard had spent most of his time studying at Nottingham, Natasha had done a little more partying on the south coast at Brighton. After uni, Richard had secured himself a graduate placement with one of the top recruiters and had gone from strength to strength in his first four years reaching a respectable position in middle management. He had direct supervision over twenty employees now, with a rough split of 50/50 male and female employees. They were a mixed group of folks, some having been there for years, with others just behind him on the post-uni route from college. He had had his fair share of women in the past, but right now, work was his priority. There was a potential for another promotion in the pipeline, and he was devoting all his efforts towards securing a big contract that was in the offing. If he got it, then that would certainly have a good affect on his promotion chances. It was all due to be finished next week, one way or the other, so a break to see his sister in London would do him the power of good.
Natasha had enjoyed her time studying in Brighton. It was a fun town anyway, and she made the most of it. Brighton is a place that attracts people from all sorts of backgrounds, and Natasha had met a lot of them in her time there. Following graduation, she had gone travelling for a few years, circumnavigating the globe in that time. A year was spent working as a waitress in Sydney, but she had also been to India, Nepal, Vietnam, Thailand, Malaysia, New Zealand, Argentina, Chile, Brazil and Canada. Thailand had been fun. Whilst at uni, Natasha had trained up and got her qualification to teach scuba diving. She had made the most of that in Thailand, teaching diving in the Andaman Sea, and leading trips out to see the Whale Sharks.
She was also a keen observer of life, and her love for photography had brought her a wealth of pictures to bring back to show her family and friends. In addition to the scuba diving, Natasha had discovered other interests in Thailand. She knew before she had arrived there that one of the most famous, or infamous things in Thailand were the lady boys. They were a novelty when she had first arrived in Phuket, but working there for six months, she had come to meet several on a number of occasions, and had befriended one in particular, called Helena. She/he had chosen to travel from her village in the northern hills to Bangkok about four years previously, as her family were extremely poor and there was not enough work to support her there. After three months of living on the bread line, she had approached a clinic specialising in gender re-assignments. Two years later with all her disposable income spent on the cause, she was the vision of beauty that Natasha had met in a bar in Phuket. Her petite figure was no more than a size 8 back in the UK, and her feminine facial bone structure would have been the envy of any catwalk model. She had typical glossy black Oriental hair that cascaded down to her waist.
Helena had told Natasha about the pressures that had forced her to undergo the treatment and of the pain that some of this had caused. Nevertheless, she was happy; she had money, friends, and a decent home to live in. Natasha had grown very close to Helena over the months she was there, and after a few drinks one night, they had finally gone to bed together. It had been a purely female-on-female liaison, Helena having had the final operation some months earlier. It was a beautiful night of caressing, touching and sensuous pleasure. Using fingers, toes, lips and tongues, each had brought the other to climax time and time again throughout the balmy night, and had slept, exhausted, for most of the next day. The two girls remained close friends for the rest of their time together, but had kept their lovemaking to that one special night. Natasha was most definitely not a lesbian, but her curiosity had won her over, and had certainly changed her views forever about sex and sexuality.
Back in the UK Natasha had managed to secure herself a position in an up-and-coming PR agency in the City. She had started as a secretary, but had quickly shown to her bosses that she was an extremely capable young woman and had risen through the hierarchy quickly. As a twenty-something PR Executive and being gorgeous, stylish and confident with it, she had the choice of any of the over-eager men pining after her in the after-work bars of the City. After several carefully selected dates, she had chosen Robert, a 33-year-old stockbroker from Berkshire. To start with, he had been one of the lads; a bit loud and a bit full of himself. By the end of their first date, Robert would have done anything for her; he was besotted, and she knew it. When she flicked her long-blonde hair over the shoulder of the jacket of her skirt suit, his tongue almost rolled right out of his head. Five months on and things had changed very much for the both of them.
An unsurprising ten minutes late, the train pulled alongside the platform at Euston Station. Richard walked up the ramp to the concourse and waved at his sister sitting on one of the benches. "Nice journey little brother?" Natasha enquired. "Less of the little please bossy boots!" Their conversations usually started like this, but soon calmed down after a few minutes.
Once back at Natashas flat, the tea was made and the two sat in the living room chatting. Richard was talking, " and the fine print to this contract is getting ridiculous. They keep harping on and on about some tiny points that will amount to all of five thousand pounds, out of a contract worth two million. If they continue like this then they will probably "
"Richard," Natasha interrupted. "I dont know whether you had any thoughts for plans this weekend, but I have been thinking that we do something a bit different."
"Such as what?" he asked, with a quizzical expression on his face. "Im intrigued."
"Well .you remember when we were at university and you were going to that party, and I helped you find something to wear "
Richard was gob-smacked. It had been a role swapping party during the Freshers Week and Natasha had come to visit for a couple of days. She had brought a selection of clothes from her rather extensive wardrobe, but had worn a very simple businessmans suit herself. When Richard had stripped down to his boxer shorts, Natasha had stood in front of him and shook her head. "If Ive come all this way to help you, then well do this properly. Drop em. Ill turn around; dont worry. And put these on. They are a bit fiddly, but if you put yourself into the front bit, pull it through and attach it at the back, it will give you a nice smooth, natural line." When she turned back to face him, Richard was wearing the panties she had given him, and the bulge that had been there before was securely tied back through his legs. "Lovely," she cooed. "Now I think well get you this bra in place. I know one or two people down in Brighton who know about these things, and they gave me these." Natasha held up two breast forms that were so realistic, they were almost indistinguishable from the real thing. Richards eyes were wide open staring at the breasts. Natasha moved forwards and began to stick the forms onto his chest. He was lucky that he did not have much body hair, so the glue stuck to his skin instantly. Straight away he could feel their weight pulling forward, and when Natasha slipped the lacy bra over his shoulders and attached the clips at the back, the switch of weight to the shoulder straps was a relief. It took a little getting used to, but the gentle pulling of the straps felt almost reassuring to him, standing in front of his older sister. By this time, Richard had gone quiet, and already Natasha sensed there was something else going on, although she was not sure what. "Eh Richard, put this garter belt on next and remember to slip the straps under your knickers. Dont ask why, but youll thank me for it later. Once youve done that, there is a pair of stockings on the side. Be very careful when you put them on; roll each one up first with your fingers and slide them up your legs. Take your time, and enjoy it," she teased. She wasnt sure whether he had heard everything she said, but he seemed to do what she had said. The next five minutes was spent fitting a corset round his waist. After some pulling a tugging, it was as tight as it was going to go and Richard had a beautiful hourglass figure. She had proceeded to take out each of the five cocktail dresses in turn and hand them up along the curtain rail for Richard to inspect. Natasha had thought that she would probably decide on the dress for him, but sensing his interest, she left him to choose. In the end, with very little persuasion, he had tried on each of the five dresses, just to make sure. He had finally gone for a black dress, about four inches above the knee. The body was quite low cut and strapless, now he had needed a different bra to match. It was made from black satin material and hugged his newfound female curves. The lower part of the dress was lined with a silky inner, but the outer was very flouncy with several layers of lacy netting to give volume. Natasha had been forced to give her brother lessons in how to sit with the dress on, so that he didnt ruin the lace, and he had seemed to quite enjoy the attention. She had done his make up with bright scarlet lipstick and lilac eye shadow with some delicate blusher to highlight his cheekbones. With a spray of her favourite perfume of the moment, Tommy Girl, the wig was the finishing touch. Richard had short hair anyway, so the shoulder length brunette bob fitted easily. Natasha told her brother that he looked like Lois Lane, and she thought she noticed him blushing slightly, but he quickly turned away before she could be sure. A friend of hers had lent her several pairs of shoes to lend to Richard, and they had opted for a patent black leather court shoes with a 1" heel, just to accentuate his lower legs.
The party had been great. When the siblings first arrived, Natasha had heard one of her fellow be-suited females say to her brother that it was supposed to be a role swapping party. The girl had been a little embarrassed when Natasha had stepped in and explained, but she quickly complimented Richard on his outfit and make up, telling him that he was certainly the most convincing role swap she had seen at the party. They had danced the night away, and both had been asked to dance at least five times each, but all had been boys dressed as girls doing the asking. When Richard had been asked, he had kept quiet, but dropped his eyes and shook his head in a very feminine manner. Natasha had been amazed at the transformation she had completed, with the look to start with, but even more so with the total change in attitude from her younger brother. Without anything being said, her brother had sub-consciously started acting like the girl he was dressed as.
At the end of the evening she had helped him out of the dress and underwear and helped him clean off his make up. They had never mentioned that night again and Richard had thought his sister had forgotten about it.
The memories had come flooding back to Richard when she mentioned the party, and he was starting to perspire freely. "Yes, I remember," he said, trying to sound nonchalant. "What of it?"
"Well I thought it might be fun to do something like that again, but this time for the whole weekend. What do you think?" she asked.
Richard thought for a moment. "The whole weekend? It was a long time ago when we did this, and it was a college party. Is there a party that is going to go on for the whole weekend? That sounds like quite some party!"
Natasha continued. "Youre right in some way. There is a party tomorrow night, one where we can go with a role swap theme, but I thought it might be more challenging to have a whole weekend of fun, doing different things around the city. Robert is going to do it, and I think you are too Richard."
Her voice had subtly changed when she came out with her last line, and sounded quite stern. "What do you mean by that Natasha?" he asked rhetorically.
"Richard. I really dont think I need to answer that, do I? I do have a memory, and I can remember clearly our night at your college. Dont even try and deny you did not enjoy that night, and not just the beer and dancing. You loved every minute of that night, especially the preparation, and you looked positively depressed at the end of the night when you had to take my dress off. So dont go there! Look," she said more softly, "you know youll love it, so just go with the flow. Dont make me have to force you!!" Her voice had changed again, and Richard realised he had no choice but to go along with her plans.
"Can I ask one question?"
"Despite what you say, if I had the choice I would not be doing this, but I want to know how you got Robert to participate in this scheme of yours?"
"Thats a damn fine question, but if I tell you, you will have to promise not to tell him that I told you. Ive told him that Ive given you some story about a charity fund-raising thing hes doing."
"No problem. Go on."
Natasha spent the next fifteen minutes explaining how she had slowly taken control of Robert using her overpowering femininity as her tool. Richard had been barely able to comprehend the deviousness of his sister. She clearly had her boyfriend wrapped around her little finger from the start, and when she first asked him to start wearing one of her lacy thongs under his suit to work, he had paused for only a second. This had developed into wearing a different pair of panties each day. After only a few weeks, Natasha had instructed him he must buy some of his own. Shocked at first at the prospect of having to go into the lingerie shop on his own, he had succumbed to her pressure and gone to the shop one lunchtime. It had been a thoroughly humiliating experience for him. No matter how many times he had tried to explain to the young sales girl that they were for his girlfriend, she had just smiled and winked at him. "The lady doth protest too much," she had teased.
The day after this, Natasha got him wearing one of her nightdresses to bed. "Natasha, are you sure about this?"
"Robert. If you have to ask me that, then I think you should seriously think about the direction this relationship is going. What do you want out of it? If you want different things to me, then you know where the door is, and can I ask you to pull it closed after you. Otherwise, then I will just ask you do a few little things, and we can remain the hottest couple in the City of London! Which is it to be?"
Without saying another word, Robert had walked to the drawer, pulled it open and selected a baby blue silk slip. Still wearing his pink thong from his day at the office, he raised his arms above his head and let the soft material slowly drop, sliding gracefully over his arms, shoulders, across his chest, coming to rest, lightly caressing the tops of his thighs. He closed his eyes involuntarily and shuddered slightly. Natasha watched, and knew instantly that she had him trapped. From that moment onwards, there was no more defiance from Robert. She had started to make him wear tights to work under his suit, and she could tell straight away he loved the feel of nylons on his legs. He became quite the expert at putting the delicate garments on and would make his own choices of colours and denier. Often he would choose the sheerest tights in the drawer claiming that, "they are less suspicious to anyone at work as they dont make my suit trousers stick to them." Natasha knew that was rubbish; she was the only one who knew he was wearing the tights under the trousers and she could not tell the difference between the different types. Nevertheless, she never criticised him on this, and secretly loved his little foible.
It had stayed like this for a few weeks, just letting him get used to the feel of his female foundation wear. Then one day Natasha had phoned him at work. "Robert, just thought it might be nice to meet up for lunch today. Are you busy?" she asked.
Robert was about to tell her that he was indeed extremely busy, but he thought better of it. "That would be lovely darling. Where do you fancy?"
"There is a new place near my office that is supposed to be good. Its quite a big place, but I had better book, as it always seems packed when Ive passed. Meet me at One."
Robert had arrived there five minutes before One oclock and was waiting at the table when Natasha walked in. She was carrying a shoulder bag that he had never seen before, but didnt mention it as she arrived at the table and he got up to kiss her on the lips. "You smell good," he remarked. She looked up at him, smiled and replied, "Thank you sweetheart."
The meal came to an end and Natasha insisted she paid for it. "Come with me lover NOW!"
Robert got up straight away and followed her as she headed further into the restaurant and eventually to the womens bathroom. "What are you doing? I cant go in there."
Instead of forcing him, which she knew she could if she chose, she smiled again, winked mischievously and pulled him gently by the tie. He entered willingly and she led him straight to one of the cubicles, locking the door behind them. She was on him in a flash, undoing his tie, unbuttoning his shirt and taking off his trousers, whilst all the time caressing his body, gently rubbing his panty-clad manhood with the tips of her fingers. She knelt down in front of him, kissing the area around his nylon-clad inner thighs, moving back up to his now-throbbing cock. Suddenly, in a flash, she scooped up his clothes off the floor, unlocked the door and rushed outside, leaving him standing there in his pretty, feminine lingerie. In loud, hushed tones, he blurted out, "Natasha, what are you playing at? You cant leave me here. Ill get arrested or something."
She could tell he was really scared, alone in the small cubicle and sought to reassure him. "Robbie, Im not going to leave you, but you must do what I say. Ive brought a few bits and pieces with me for you to wear. Before I arrived, I phoned your office and told them you were a bit poorly. They arent expecting you back in the office today, so I thought we could take a nice walk back through Hyde Park and enjoy the sunshine. Now dont argue; you arent really in a position to argue, so pay attention." She began to pass one item after the next under the closed door until her shoulder bag was empty. "Are you ready to come out? Oh, sorry. I didnt mean that the way it sounded, but I guess it fits!" she giggled to herself.
The door unlocked from the inside, and out stepped a 5 10" fellow blonde, with his new shoulder-length wig, dressed in a short, red pleated kilt that came to about halfway down his nylon covered thighs. He wore a see-through cream silk blouse under which Natasha could clearly see the cream-coloured lacy bra she had provided to hold up the breast forms. With shoes to match, Robert was almost passable. "You look pretty good, girlfriend!" she admired. "Lets get some make up on you and no one will notice."
"No, this is enough now please," he protested in vain.
"Are you sure?" she asked. "If you go out like that, youre sure to be rumbled, but if thats what you want "
After a moment, he relented. "Okay yes, get on with it. Please make it as convincing as possible." He was sounding almost pleading by this point, and Natasha loved him all the more for it. She set to work. First some foundation cream, to hide his male skin tone imperfections, not too dark, but just enough to give him a lovely smooth feminine face. After a touch of blusher to make his cheekbones more prominent, she had him close his eyes while she applied some light purple eye shadow. With some of her favourite mascara on his lashes, his eyes could have graced the cover of a magazine. "Open your mouth; not too much, just a little open, " Natasha instructed him. As he complied, she started to weave her magic with the luscious red lipstick she had purchased specially from the Clinique counter at Selfridges. "Only the best for my special girl, "she murmured to herself as she put the finishing touches to his lips.
The rest of the afternoon had been spent taking a leisurely stroll through the park arm in arm; to everyone else watching, just two girlfriends out for a walk, catching up on all the gossip. Apart from the slip she had forced him to put on for the first time, Robert had not really shown outwardly that he enjoyed any of the clothing she had been forcing him to wear. Walking in the park, she had sensed a small change. He had been very tense to start with, but by the time they reached home, they had been laughing and joking as if it was the most natural thing in the world. "So how was that? Not so bad?" she asked. He mumbled some non-committal answer, which she did not hear, but guessed the meaning.
"What was the best part?" she quizzed him further. "The feeling of freedom wearing your wrap-round kilt? Feeling the gentle breeze blowing around your legs in your tights? How did you like the feeling of wearing your first bra? What about wearing lipstick for the first time?"
He mumbled something again, but she knew he hadnt even picked up on the first bra bit in her last question. She smiled to herself, knowing she had changed things forever between them.
"So thats it little brother. That is why Robert will be joining us for in my plan for this weekend. I have one or two surprises in store for everyone, so perhaps you should go and get settled into the spare bedroom. Go on! Off you go and start thinking of a name for yourself. Remember youre a girl this weekend. Three beautiful girls together!"
To be continued
© 2002 by Annalise Barker. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.