tagTranssexuals & CrossdressersPersonal Assistance

Personal Assistance

bysexy_jessie©

Rolling over, feeling a little groggy, Helena Stewart quickly realised that there was something not quite right. The hard mattress was not the soft sumptuous bed of her own apartment, the bare white walls not the passionate pink of her decor. Helena realised she wasn't in her own bed, wasn't even in her own apartment. She was wearing a small black leather bra top that barely held in the whole of her DD cup breasts and a tiny tight black leather mini-skirt with her long smooth legs in kinky thigh high PVC boots. Her black lace panties were a little torn and her ass felt sore. Turning her head, Helena could see, stretched out beside her on the bed, a tall, dark haired guy with a little rugged stubble, he was naked except for a pair of blue boxer shorts so Helena could see his hairy body. He wasn't exactly the type she normally went for and Helena, remembering very little of the night before, realised she must have been pretty drunk to have even gone home with him and she always made a point of never spending the night, that was the first thing that turned no stings attached one night stand sex into the beginnings of a relationship. Her head was throbbing with the feeling of a hangover as she looked across at the digital clock beside the bed to see it was already gone 9 o'clock, it was Monday morning and she was going to be very late for work.

Helena slid the guy's arm from where it rested across her chest and slipped out of the bed without waking him, she'd leave the house and call a cab home on her cellphone. Her fitted black leather jacket hung over a chair in the corner of the room, she slipped it on and tottered out of the room on the six inch heels of her thigh high boots. Shutting the front door behind her, Helena smiled at managing to escape without having to talk to the guy again. The smile was wiped from her face when she realised she had left her handbag in the house, it had her phone, her keys and her purse with all her money in it. Helena realised that there was no way she could get home without going back into the house and that would mean talking to last night's conquest. Oh well, it couldn't be helped.

She rung the door bell and a few seconds later he appeared at the door, wrapped in an unflattering robe. He smiled at her in a way that made Helena cringe, she had been right to try and get out:

"Trying to leave already," he winked at her, "At least stay for breakfast."

"I'm late for work, just give me my handbag and I'll get out of your way."

"Let me give you a lift to work," he offered, the guy was clearly desperate, she must have been extra good last night, but she thought it would be cheaper and less embarrassing than getting a cab.

"I can't go to work dressed like this," she told him, "Take me home."

She saw him smile at the thought that he would be able to see where she lived and she made a mental note to get him to drop her off at the corner of the street. In the car he tried to make conversation but Helena deliberately ignored him apart from giving him directions to the street where her apartment was. Getting him to drop her off at the corner she got out of the car and, feeling generous now she had got away from him, turned back and smiled:

"Last night was really great. . .er. . ."

"Paul," he told her.

"Yeah, Paul, last night was great, we should do it again sometime, I'll give you a call."

Waiting to see him pull away, Helena hurried to her apartment building and up the stairs to her sumptuous luxury apartment, it was now 9:30 and she was getting later and later for work but she had to shower and change, she couldn't, as she had told Paul, go to work dressed like this. Helena walked into her large bathroom and looked at her reflection in the bathroom mirror, her lipstick and make-up was all smudged and the blonde wisps of her out of place. Carefully she removed the wig, for her real her was short and dark, and stripped out of her tight leather outfit. Turning on the warm running water of the shower she stepped under it and washed away the remaining elements of last night, the smudged make-up running from her face. The water running down between her huge breasts and down her smooth chest towards the six inch cock that hung between her smooth thighs. The soapy water of the shower washed away the glue that held her breasts in place and she removed them from her flat chest and stepped from the shower. The reflection in the mirror was now of somebody completely different, with the clothes, wig, make-up and breasts removed sexy Helena was transformed back into her daytime self, respectable Henry who dried himself off, put on a suit and hurried out of the apartment to his car to drive into work.

Henry got to the offices of his computing firm just after 10:30, he was an hour and a half late and he practically ran from the car park up to his office on the third floor of the three storeys that the company owned. He knew being that late would have got him into some serious trouble were it not for one thing, it was his computing firm and he couldn't get into trouble with anyone senior to him because he was the boss. Henry Stewart had formed Stewart Computing back in the 1980s and the company had gone from strength to strength making Henry a rich man. Two years earlier he had split up with his wife of fifteen years and moved to his apartment in San Diego closer to the offices of his company. Ever since, he had been living the strange double life as Henry Stewart, respected and respectable computing executive during the day but as soon as he got home transforming himself into sex kitten Helena going out for nights on the town hoping for some no strings attached sex. For two years Henry had lived this life quite happily and he had no reason to think that there would be anything that would change it now.

Hurrying into his large office, he was stopped outside by his new PA, Jemma Stevens. Jemma was in her mid-twenties and had recently graduated college with a major in business management, on the advice of his friend Naomi, Henry had agreed to hire Jemma temporarily as his PA to get some experience of the management world. She could have been quite pretty if it weren't for her thick glasses and how her blonde hair was cut in clumsy fringe, she dressed conservatively and was normally quiet and kept to herself around the office. Jemma had only been there for a month but Henry knew that she was far more capable than the job required and, although she wasn't the most social of people, she, did her job very efficiently and Henry found himself increasingly trusting her with more and more important things. This morning, Jemma had masses of things to go through with him, but mostly he could see she had already come up with ideas and solutions for most of them and so he found himself able to sit there and plan for Helena's next weekend out.

***

Friday night and Helena was out in a club again, looking to pick up another hunky stud. Tonight she wore a tiny black halter-neck dress that she really had to squeeze herself into and that had her false DD cup breasts almost spilling out in a way that she knew really attracted the guys. The tiny skirt of her black dress clung to her pert ass which it barely covered and exposed the whole length of her sexy smooth legs which she accentuated with the heels on her black ankle boots. Her normal way of going about things involved ordering a cocktail from the bar and slowly sipping it in an enticing sensual way while she thrust her breasts out and simply waited for guys to approach her, it usually didn't take too long.

Across the flashing strobe lights of the dance floor, Helena thought she saw somebody she knew. Her back was slightly turned away from Helena and she was dressed unlike the way that Helena was used to, but Helena was sure she recognised her, or to be more precise Henry's, PA Jemma. The big glasses and bad haircut were recognisable but the tight revealing clothes nothing like Jemma's office wear. However, Helena didn't linger overly long on Jemma because her eye was instantly drawn away to the guy she was talking to. Unlike Paul of the night before, this guy was hot, he was absolutely the type of guy that Helena tended to go for and she desperately hoped he would come over and approach her but was worried that Jemma might recognise her if she came over and that could cause serious repercussions in Henry's life. The guy was tall and totally toned and muscular with tight pants and a T-shirt that showed off his very impressive chest muscles. He had a perfect white grin that was on show quite a lot as he seemed to enjoy whatever Jemma was saying. Helena felt a pang of jealousy, she should fire that bitch, she thought before remembering that she never wanted to let her two lives cross, which was why she didn't want Jemma to look over and recognise her.

She looked down at her drink to avoid Jemma's gaze as she looked over to Helena's side of the room. When she looked up again, Jemma was gone and the muscular guy was coming her way. She took a moment to compose herself, suddenly a bag of nerves where usually she was so confident with guys and took the lead. Maybe it was the association with Jemma that had made her nervous, maybe it was the fear that she had been recognised. Helena turned her gaze from the approaching guy and saw someone else coming towards her, someone else she recognised. It was Paul from the weekend before, how had he known she was going to be here? Or was it just a coincidence? He smiled at her as he came over.

"Hi," he said, "Fancy meeting you here,"

Helena was totally slumped, this had never happened to her before, she had no way of getting rid of the guy. Quick sex and then she would leave, that was the way it always worked. She felt someone at her elbow and heard a deep masculine voice say:

"I'm sorry, what do you want with my girlfriend?"

Helena turned to see the hunky guy from across the room standing beside her, looking threateningly at Paul who looked scared for a moment and then left. Helena turned gratefully to the new guy and smiled at him, he flashed, back his brilliant white smile.


"I hope that wasn't too presumptuous of me," he said, "But he looked like he was bothering you,"

"It wasn't presumptuous at all," Helena tried to get her voice into control with its normal alluring purr, "I'm Helena," she held out her slender, manicured hand and he took it in his big, strong grasp.

"Matt," he said, "Would you like to dance, Helena?"

As well as being incredibly sexy, Matt was also a great dancer and he held Helena close to him, totally taking control, so her breasts pressed against his chest and their crotches ground together until Helena felt a stirring of arousal in hers. She took his head in her hands and pulled it down to hers, kissing him passionately on the lips.

Back at Matt's apartment, Helena wasted no time and, as soon as they were in the bedroom she dropped to her knees and stripped Matt's pants off him, freeing his cock which sprang free in her face. Ignoring all her many talents and abilities at cocksucking, Helena simply opened her mouth and took the whole length of his throbbing, erect member into it and began to rapidly and excitedly suck on it in a way that was making her feel totally aroused, far more so than she had in a long while. She could tell from Matt's groans and his throbbing cock that he was close to a climax and she let his cock slide from her mouth, letting a string of pre-cum trail between the two.

"I want you to fuck my ass now Matt," she said, beginning to retain the control she normally took with guys.

Going over to the bed she propped her ass up with pillows, pulling her cock up beneath her in the process in order to hide it. She pulled up the skirt of her little black dress just a bit, it was so short it barely covered her ass anyway, and pulled aside her black lingerie thong to allow access to her anus. Spreading her legs, she enticed Matt in and he didn't need a second invitation, thrusting his cock eagerly up her ass. Her experienced ass didn't have too much difficulty in taking in Matt's cock and soon he was thrusting hard in and out of her ass, levering himself on her bare shoulders. As Matt thrust towards Helena's prostate she felt a greater pleasure at this than she had in a long time, her own cock buried in cushions was rock solid and, as Matt continued to enthusiastically thrust in and out of her she groaned and screamed the house down until her cock, grinding into the pillows beneath her could take no more and she unloaded all her sticky creamy cum into her tiny thong. Her ass clenched around Matt's cock and this was all he needed to blow his considerable load up her ass. As was her habit, Helena excused herself to go clean up in Matt's bathroom and cleaned the cum from her ass and thong before leaving his house to go home. Despite the great quality of the sex he didn't want a relationship to start complicating matters.

***

Henry arrived at work on time the following Monday but Jemma was still there before him, dedicated as ever. Most of the rest of the office had still yet to arrive. Henry had forgotten until that moment seeing Jemma in the club on Friday and was about to bring it up before he suddenly realised what that might reveal about him and what that might make him explain. Jemma handed him a file of the week's business as she did every Monday and Henry went into his office to read it. Opening the file, out fell a series of glossy colour photos, that was unusual. Henry looked at them and realised that they were all pornographic pictures of couples having oral and anal sex. How had Jemma somehow got these mixed in with the week's business? He was about to go out of the office to get angry with Jemma when he studied the photos more closely. He could see now that the busty blonde sucking off the muscular hunk wasn't just any pornographic photo, it was him with Matt that Friday night. The photos went on to show him lying face down on the bed, legs spread with Matt thrusting into his ass and an _expression of pure ecstasy on his face. That wasn't all, there were pictures of him, or more precisely Helena, in his black leather bra top and skirt and PVC thigh high boots, on his hands and knees being fucked doggy style by Paul the week earlier. In these the outline of his erect cock in his leather skirt was clearly visible, he was drunk and being less careful, and he realised that because of this he would be obviously recognisable were the photos to get out. He didn't know how she had done it but he realised Jemma was blackmailing him. He called her into his office.

She came innocently into the office, dressed in her usual conservative office clothing, looking in no way like a woman involved in sexual blackmail. She smiled politely at him. He turned the photos towards her.

"What's this all about?" he asked.

She smiled farther, she had a nice smile, a little wicked perhaps in light of the situation, but attractive, "Your friend Naomi thought it was about time you decided to fully embrace your womanhood," so that was how she knew, "If you follow my instruction and do everything I say then nobody else in the company needs to see these pictures."

The first thing that Jemma desired him to do was to quit the day to day running of the company and to hand it over to her. Although Henry was a little doubtful about what other, more senior, members of the company might think to this, he knew that Jemma was well qualified and talented enough to take control of the running of Stewart Computing without any damage to his financial situation and, indeed, she may even be able to inject some new ideas into the business. Therefore, after only a brief consideration, Henry handed over the reins of Stewart Computing to Jemma, the new managing director. As Henry had thought, there was briefly some objections and difficulty from some of his staff but Jemma was able to establish her authority in dealing harshly with these and with her obvious competence at her new job.

His freedom from having to present himself every day as Henry Stewart enabled him to spend his days working towards Jemma's second demand, that he devote his time to a permanent transformation from Henry to Helena. He began to live as Helena all day and, at the same time, begun a course of hormone therapy and various operations in order to fully transform him physically and permanently into Helena. Once again, Henry was quite willing to acquiesce to this demand of his former PA, he knew that for the last two years living and loving as Helena had been the cause of all his pleasure and passion while his days as Henry had purely served the practical function of allowing him to continue to accumulate money which he spent on Helena's clothes and beauty products, on her nights out and, now, on her operations.

That wasn't all that Jemma desired of him, her final demand was for continued sexual favours for both herself and the guys she brought home. Jemma moved into Helena's luxury apartment and assumed total control over her love life. Not that Helena was complaining particularly, she enjoyed sex with all the guys that Jemma brought for her and pleasing Jemma herself became something that Helena began to enjoy increasingly much. Jemma and Helena lived like this for some months with Jemma now running the company while Helena spent her days shopping and having fun. Jemma never really bothered Helena with the details of the business any more, saying a woman like Helena didn't need to bother herself with such issues and, as the money continued to come in, Helena felt that she really didn't need to bother herself any more with such problems and felt herself pleased at the lifting of such a weight of concern from her shoulders. However, one day Jemma did decide to involve Helena in the business in something of an unusual request.

"I need a favour from you Helena," she said one day, which Helena thought a little strange as Jemma didn't ever ask anything of her, "There's a guy coming to town, David Stiller, a very rich businessman who is thinking about investing in the company," Helena was a little confused, Jemma never bothered her with issues concerning the business any more, "David is the kind of guy that gets a little lonely away from his wife on these long business trips, I need you to show him a good time, take him out for dinner, do what you do best."

"Why do you need me to do this?" Helena asked, "If David is after a woman then why not you? You are, after all, more of a woman than I am."

"I'm the manager he's dealing with, I can't also play the slutty woman who tries to seduce him. Besides, you know your feminine wiles and charms far exceed mine and he never has to know that you're not everything you seem."

So, set up by Jemma, Helena found herself that Friday dining in a very fancy restaurant with a potential investor, knowing that the future financial strength of the company could rest on his performance this evening. David Stiller was in his late thirties, a similar sort of age to Helena herself, and generally unremarkable looking, relatively, but not notably, short, medium build, with short gingery brown hair and some freckles that made him look younger than he was. He was dressed in a business like grey suit that showed him to be someone who probably tended to put business before his family. Helena herself was dressed in a black evening dress with a plunging neckline down to the cleavage of her new, genuine, breasts that she had recently acquired and was particularly proud of. She wore a diamond necklace that had cost her heavily recently and that instinctively drew the attention of anybody who looked at her towards the curve of her breasts. The black velvet dress was slit up the side of the skirt to give a glimpse of her long, sexy legs encased in black silk stockings and a brief flash of skin above her stocking tops. Her blonde wispy hair was tied up in an elaborate, expensive and glamorous style. Overall, Helena felt herself dressed in such a way that she couldn't fail to impress. Sure enough, over dinner, as she fluttered her long false eyelashes and listened attentively, she could see David's eyes constantly drawn to her cleavage and exposed leg and a little tremble come over him as she gently rubbed the inside of his leg with her foot and slowly stroked the stem of her wine glass, pouting her scarlet lips.

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bysexy_jessie© 11 comments/ 79562 views/ 12 favorites

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