Ugly Duckling 2

All comments and feedback are gratefully received as I'm hoping the feedback will encourage improvements in my work. This is a work of fiction from the deep dank recesses of my mind and any resemblance to real people is purely accidental.

This story depicts first time sex, if this not to your liking, please visit some of my other submissions, otherwise I hope you enjoy.

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Greg had to do a double take when he saw her. He was a regular at the community swimming pool and you could invariably set your clock by his appearances and the number of laps of the pool he would make. He had seen Lauren in the reception area and purposely waited by the edge of the pool to give her a friendly welcome but then she emerged from the changing area and his jaw nearly hit the pool floor.

Around the office Lauren would definitely be classed as an ugly duckling. She dressed like her mother in large flowery dresses that concealed as much of her body as she could manage. She wore her hair long so that as she walked around with her head bowed, she could peak through her fringe and hide against the world and the glasses that she wore resembled the bottom of beer bottles they were so think.

Now though was a very different vision. Her hair was bound back in a ponytail to reveal a rather pretty face, her glasses had understandably been left behind, meaning she was effectively squinting to see where she was going. What really drew Greg's attention was the body inside her one piece swimsuit. The slim waist tapered down to a rather pert butt and shapely legs but he found it hard to look away from her chest -- simply magnificent - at least a 44DD he estimated. He had no idea that she was hiding such a delicious sight below her office clothing.

In his defence, Greg did his best to focus on his usual regime but he kept glancing in Lauren's direction and when it looked like she was getting out of the pool he did the same at the opposite side and made it look like an accident when he bumped into her "Oh sorry, hey it's Lauren isn't. Hi, I didn't realise you used this pool too, how are you?"

The look she made as she squinted to see who had addressed her almost made Greg chuckle, instantly the stereotypical cartoon mole coming into the light sprang into his mind. She had stepped back and in time came to the realisation of who it was "Oh hello Greg, I didn't realise it was you for a moment. I'm good thank you. A friend recommended this place and I'm glad she did, it's very good."

Greg answered "Pleased to hear it, this is my usual place. I wouldn't mind a catch up with you sometime next week if you can free me some time. I have a job opening that might be just up your street if you are interested. Drop an invite in my calendar as I think you'd be perfect for the role." With that he went off to the changing rooms leaving the young woman stunned.

He was the last person she expected to see here and a job offer certainly seemed too good to be true. She must have stood there with her mouth agape for a good few minutes before rousing herself to make her way back to the changing rooms. She didn't see Greg as she left the facility but logged on when she got home and looked for an unallocated spot in his calendar. The meeting had a more profound impact on Greg who had trouble getting the mental image of her impressive chest off his mind -- it really was quite extraordinary.

When the appointed time arrived in his calendar Greg was looking forward to the meeting. A timid knock on his door was answered with a loud "Come in." As Lauren stepped into his sanctuary he gestured to the seat in front of his desk and smiled broadly as he said "Thanks for coming to see me. Please take a seat." He was a little disappointed with her dress that was back to her mum's frumpy floral dress, thankfully he had that vision of her in the swimsuit to spur him on. "I have a new role that I need to recruit for. It is admin but as you know the business, the structure and people here and how we operate you were the first person that sprang to mind."

Lauren was taken aback initially. She tried not to stand out while going about her business but she had obviously done enough to come to Greg's attention. He went on to explain what the role required and her ego was suitably inflated when he announced that she would be working closely with him on key campaigns. "I do have to address the elephant in the room though. The people we will be meeting will be paying big money for the company's services and they have certain expectations." He fidgeted in his seat slightly as he paused but then blurted out "We'll need to alter certain aspects of your appearance if you are okay with that. The company will fund them initially and I'd like to think that the significant increase in your pay packet will be sufficient for you to carry on the good work on your own."

Lauren looked puzzled and asked, "How much extra is the pay and how much will I have to spend?"

Greg smiled his warmest smile and replied "I've checked with payroll and your pay will rise by 50% if that is acceptable. As for the 'regeneration fund' as I'm terming it, we'll pay for three or four suits for you as well as a selection of blouses and skirts for around the office but I think a suit is appropriate when we have meetings with the customers. That brings me to the glasses, I'm afraid they'll need to go. We'll pay for a year's supply of contact lenses to get you started; would you try wearing those for me?"

Lauren still resembled that rabbit in the headlights but could muster a nod as she slowly replied, "I will give them a try if you insist and I can't thank you enough for the job, the pay increase and the clothing allowance."

Greg waved his hand dismissively "Nah, think nothing of it. I think you'd knock this role out of the park, after all I've seen how you work and having asked around the office, it seems my fellow managers have the same opinion as me." If truth be told most that Greg had asked had trouble working out who she was, those that knew her referred to her as the ugly duckling but importantly her managers manager had confirmed how industrious she was with the minimal of fuss. "I think we can extend to a new haircut as well. I have a friend who will provide a suitable, professional look."

"I can't thank you enough. I hadn't realised I'd made such an impact but I'll make sure your faith in me is suitably rewarded" came her gushed reply.

'To hell with that' Greg thought as he pictured her once again in the swimsuit 'I could really shape her into something special given enough time but I can only do that if she is working directly for me.' Again, another dismissive wave as he countered with "I'll arrange a suitable transfer point with your line manager and the Friday before I'll take you out myself as there is a certain look that I want projected. Once you get up to speed with the role you can shape yourself as you see fit."

That Friday afternoon came along and Greg whisked Lauren out to a nearby store where she picked out some suits, some blouses to go with them and a couple of pairs of shoes that she would have to practice walking in as she didn't have that much experience with heals, normally favouring flats. A nearby optician tested her eyes and after a raised eyebrow placed an order for new lenses to arrive early the following week and the final act was to whisk Lauren off to his friend who managed to conjure up an appropriately professional style. With all the receipts parcelled up for later expense claims Greg took Lauren for a drink once the various bags had been dispatched to her home. "You really are so very nice to do all this for me" Lauren stated.

Greg smiled back and replied "I'd like to think I am a good judge of character and see a determination in you that I rarely see. After all, to my knowledge, we've never given someone a clothing allowance but I think it is worth it. You've evidence this in the thorough way that you had all your existing tasks sorted well before today and Monday sees you enter a whole new realm. It might look a bit like Alice in Wonderland but rest assured I'm not the type to plunge you straight in at the deep end -- did you like that reference to our meeting at the pool?" He chuckled at his own joke even if it took a few heartbeats for Lauren to catch on to the reference. He continued "I'll be gradually introducing you to various aspects of the job but any questions you have at any point just come and see me. I want you to grow and when you are ready, spread your wings."

More than a few of his fellow managers had to do a double take as they came across Lauren the following week, especially after she adapted from her glasses to contact lenses. It took some time but she was determined to succeed with them as Greg had come up with the idea and she quite liked the newfound attention she was receiving. True to his word Greg was increasingly introducing her to various aspects of the role. Initially he had included her in internal planning meetings. That evolved into face to face meetings with the clients and then eventually she was asked to present certain aspects of the project that Greg had versed her in.

Greg was pleased with Laurens evolution. She certainly looked the part in her suits cut to flatter her figure without it portraying her as a slut. She always listened to every word of advice he gave her and implemented the suggestions as quickly as she was able and over time found it easier to question Greg, sometimes questioning some of the things he said -- although she couldn't shake the feeling that he had perhaps put them in his script deliberately to see if she spotted the glaring omissions. Her confidence was good to see but Greg couldn't help feeling there was more talent as yet untapped.

This came to a head a few months after Lauren started and it required that they both attend a trade exhibition. More by luck than judgement the hotel they were staying in had a pool and Greg had purposely mentioned that he was bringing his trunks and that Lauren might want to follow suit as he had read some good reviews about the hotel's facilities. They arrived at their hotel the evening before the first day and were sat sharing a meal at the hotel's restaurant. Although their working relationship had progressed well, both thought it was quite nice to open up to the other on a personal level. They would later adjourn to the bar but both had an early night in preparation for the next day.

As Greg had predicted, it had been hard on the feet although she was thankful that he had suggested reverting back to her trusty flat heels. They made plans to meet up in the restaurant later on but Greg wanted to try out the pool before then and had just settled in a steady stroke when he saw Lauren walking to the pool in her blue swimsuit. He swam to that end of the pool and stopped to greet her "I take it you similarly wanted to take the strain off your feet?"

This time when he addressed her, she had her contact lenses in place and wasn't squinting around to see who had addressed her; being able to see detail clearly Lauren caught the fleeting glances Greg cast at her chest and then her legs before raising his gaze to her face. The glances sent a shiver up her spine but her lack of experience of physical contact unnerved her slightly as she didn't appreciate why she was feeling this way. Greg beckoned her into the pool and Lauren felt suitably more relaxed once she was emersed in the water with just her head above the water line. They stood in the water chatting about nothing in particular both enjoying letting the water take the weight off their feet.

Greg made a joke about seeing Lauren in a different light with her in a swimsuit which led to her splashing him; naturally he had to return the favour and so ensued a fair bit of splashing and giggling from both; they were the only two in the pool at this time and so weren't disturbing anyone else. The splashing led to some playful tickling and then the inevitable happened as she tried to get away from him, Greg made a grab and as she twisted his right hand came to rest on her nearest boob. The size of the fleshy orb dwarfed his palm and Greg sounded a deep involuntary groan; perhaps more importantly he never moved it and neither did Lauren move away. All she could do was look down at his hand and then up into his face. His expression was one of pure reverence and she found she actually liked it. The looks she had generated recently in the office had become addictive and this seemed the next evolution.

Lauren had had one boyfriend in college who was very respectful and had touched her breast on one occasion but he had been so scared she never saw him again. Here was a man far more worldly wise than herself who showed a fascination for her chest; something she never understood as she viewed her chest more of an inconvenience. She saw other woman flaunt their cleavages with plunging necklines but she never quite understood men's fascination with them. They frequently got in the way and, depending on what she was doing, would frequently give her back ache.

Greg stood there holding the fullness and staring at his hand as though he were unable to look away. He eventually looked into her face and felt compelled to bumble "I . . . errrr . . . I mean, errrr . . . I'm sorry I shouldn't, errr . . ." At no time did he move his hand.

Eventually Lauren broke the ice. This man had been so nice and encouraging to her, he had been a steady guiding hand since she had joined his team and he had ensured the company had splashed out a fair amount to get her groomed for her new role; she figured she owed him a great deal and so said "It's okay really. It feels very nice."

A broad smile spread across his face as he questioned "Really?" Lauren smiled back and simply nodded, if this is what he wanted then she wanted it too. He shook his head briefly as he added "I have never come across such magnificence ever before. The size, the shape, the sheer malleability is quite unique."

His hand had started to flex and grip gently at the flesh and Lauren felt her nipples pop out in response. This was yet another unusual sensation and the giddiness made her feel slightly lightheaded; more importantly she liked it. His gaze shifted down to his hand to stare transfixed at his fingers working and fondling the soft flesh. Just like that, his index finger brushed against her inflamed nipple making Lauren's knees buckle and causing her to groan deeply while she closed her eyes succumbing to the occasion. She had never felt anything quite like the electric shocks coursing through her extremities. Although she knew of college friends that pleasured themselves, based on her one and only previous experience she never indulged herself and had no idea such pleasure could be had. Greg saw her sag slightly and used both his hands to hold her upright as he announced, "Sorry I didn't mean to hurt you".

Lauren felt safe in his arms as she leant her head against his chest and mumbled "No, please don't apologise. I had no idea such feelings existed." Greg stayed quiet as he sensed she had more to say and she drew a deep breath before stuttering "I've never . . . you know, done . . . THAT before."

Greg was a little puzzled, not quite comprehending what she meant. "You mean this" as he brushed his fingertips across her nearest nipple.

"Oh god" Lauren groaned while gripping firmer to him. "Yes that. I don't do that . . . I'm . . . I'm . . . I'm a virgin."

Greg took a half step back and removed his hand as he gasped "Oh god I'm sorry. I had no idea, I'm really sorry. How can you ever forgive me." He was stunned that he had done this to someone who was obviously saving herself for some higher reason.

It was Lauren that finally sealed it. She once more moved to close the gap between them and brought his hand back up to her breast once more giving him the big doe eyes as she said "No you don't understand. I liked it -- I mean really liked it -- and I'd like you to do it some more. I need someone to show me these things. Would you do that for me?"

Greg really was on the horns of a dilemma. On one hand (no pun intended) he had the biggest breast he had ever touched nestled in his palm while on the other he amazed that someone so hot would still be a virgin at her age. He knew the first time he had seen her in the swimsuit that he lusted after her enough to purposely gone out of his way to encourage her to move departments and get her set for a drastic career change. Now however it was more than just an easy lay, it was taking her cherry; it was something serious that she would compare against all future occasions.

He had never deflowered a virgin before. His own first fumbling's had been with girls that had at least one previous lover before sleeping with him and he had learnt a lot over the years. Here was a very hot young woman that had previously been hiding under a whole host of disguises and at each turn she had revealed more of her beauty. He still felt it necessary to ask "Are you sure about this? It is perhaps the biggest step you will take as a woman other than perhaps marriage or giving birth. Once you've given up your cherry there is no going back."

Lauren was still staring doe eyed into his face as she replied "I appreciate that but you've done so much to elevate me, if anyone is to make me a woman, I'd like it to be you. I want to show you just how much I appreciate what you're doing for me and that seems the most precious gift I have to give you."

Greg's head was spinning, although it had to be said, not distracting enough to remove his hand from where it was nestled. "I don't know what to say. It really would be a privilege to do this for you, if it's your first time then there is an awful lot to show you as long as you are certain?" he questioned.

She made her way to the steps to climb out of the pool. Turning to look over his shoulder at him she added "I'm certain." Greg had never moved so quickly as he followed in her wake. "Where do you think we should do it?" she asked taking the final step.

"I suggest your room if that works for you. You have to know though that when your hymen breaks, there can be some discomfort. Are you sure you want this." Greg felt it his duty to ask. Lauren's answer was another look over her shoulder, a broad smile and a nod of her head. Greg really was having trouble processing that she would do this with him but she appeared ready and so after they had showered in the pool changing area's they caught the lift up to Lauren's room. As she stepped into the room ahead of him, Greg stepped up behind her and wrapped her in his arms to find her physically shaking. "I don't want you pressured at any point. Any doubts just say and we stop. Okay?" he asked

Another smile over her shoulder and nod of her head was followed by Lauren saying "Okay. I'm only nervous because I want a repeat of the sensations you were generating earlier. I think it's about time I stopped hiding and became a woman at long last."

After pulling her aside, Greg kissed the side of her neck and encouraged "Good girl. I promise to be as gentle as I can; you need your first time to be special."

On impulse Lauren turned around, wrapped her arms around his neck and stood on tiptoe to kiss him square on the lips. Greg found it a little stiff but he could tell that there was intent there and he was determined to encourage that and so he kissed her back with equal vigour. Sure enough, Lauren visibly relaxed in his arms as she continued to kiss him back -- she actually really enjoyed how open he was being with her. In an instant she knew that choosing him to make her a woman was the perfect decision.

He wanted her blouse out of the way but decided she might be self-conscious disrobing first and so he removed his shirt first and then started to unbutton her blouse. This was removed without any fuss and boy was he rewarded for his patience; the sight of her bountiful chest looked amazing; he would have to work on getting her into some better lingerie but one step at a time. He pulled her into another kiss before he removed his trousers, soon followed by her skirt. Another lingering kiss heralded him asking "Are you still okay? I'm not rushing you, am I?"