Chapter 1: The ugly duckling grows up

Caution: This Sex Story contains strong sexual content, including Mult, Reluctant, Slut Wife, Wimp Husband, Gang Bang, Group Sex, Orgy, Pregnancy, .

Desc: Sex Story: Chapter 1: The ugly duckling grows up - Plain plump booky teenager emerges in her 20s as a sexy woman, marries young and discovers her sexuality, leading to increasingly slutty behaviour and at least two illegitimate pregnancies

Dawn W was a real ugly duckling. At the age of 12, she was taller than most in her class, and the heaviest by far. She was already wearing C-cups, and the kindest thing anyone said was that she was chubby. In addition, she wore glasses and had recently been fitted with braces on her protruding teeth. Her hair was greasy and unmanageable.

Over the next few years her height stabilized, but those tits just kept growing!. By 15, she was up to DD-cups. She lacked any social confidence, and wore baggy shapeless clothes in order to hide her body. Still, she was conscious of rude comments from boys in her class about bigger udders than a dairy cow, and of mooing sounds made behind her.

She avoided social contact, buried herself in studies and became involved in church work as a Sunday School teacher. She did play (field) hockey for the school, as goalkeeper, but even that led to audible comments about how unfair it was that she left no room for the ball to get past her.

After high school she obtained a generous scholarship to study computer science at her local University of Cape Town in South Africa where she had grown up. She dreamt of meeting a boy who would sweep her off her feet, but her lack of social graces made this unlikely. The braces had by now gone, but little else had changed. She still wore baggy tops and jeans or trousers to hide her body.

Academically, she did well, and was in demand to join project teams in a quite male dominated class. It was clear that the boys on the team did not even think of her as a girl, and quite openly swapped stories of sexual conquests as if she was just one of the lads. But back in her own room, she would relive the stories, stroking her breasts and nipples while she imagined herself being ravished by one of her male colleagues. Her fingers would find her clit and pussy, as she wondered what a hard male organ would feel like penetrating her body.

One boy who was a frequent focus of her fantasies was one Enrico F in her class. He unashamedly exploited her willing help on various assignments, but otherwise hardly recognized her existence. He was of Italian extraction and lived up to the associated Romeo reputation. Stories circulating amongst the other students suggested that he bedded half the women on campus, and Dawn lay at night fingering herself, wishing she was one of them.

Dawn graduated top of her class, and was immediately snapped up by a progressive software development company in Cape Town. Within a year, she was a project leader, earning more than she had ever dreamed possible, but it made no immediate difference to her social life.

It was at about that time, though, that Dawn was taken in hand by Hilary, a rather flamboyant, red-haired and outgoing woman in her late thirties who worked in the administrative department. Hilary was famed for wearing outrageously revealing outfits, and was rumoured to have had affairs with all the bosses. She was twice-divorced and had three sons, generally accepted to have been sired by three different fathers. But somehow, she took a motherly interest in Dawn whom she perceived to be a sad and unhappy girl.

At Hilary's urging, Dawn consulted an ophthalmic surgeon, and a subsequent operation removed the need for glasses. Hilary's hairdresser gave Dawn a new close-cropped hairstyle which suited her much better. Joint shopping sprees which Dawn could now easily afford filled her wardrobe with tighter tops, displaying rather than hiding her femininity, and even showing a little cleavage and upper swells (to Dawn's initial embarrassment).

Dawn joined the local gym. She would never be slim, but her waist trimmed down, making her bosom more spectacular, and her naturally strong legs firmed up into very shapely form. Hilary encouraged her to wear shorter skirts (not quite miniskirts at this time) to exploit this new shape. Even her tits, although no smaller, seemed to get firmer, needing less bra support, and allowing her to buy a few more frilly lacy creations.

Slowly she became aware of men staring at her bosom and legs, not to scoff any more but in open admiration. However, she still lacked confidence to socialize to any great extent, in spite of Hilary's encouragement.

Then, half way through her third year with the company (just after her 25th birthday), her life changed when Gavin T appeared on the scene. He was a technician involved in replacing their network systems, and was some five years older than Dawn. He was rather shorter than her and really skinny, even wimpish looking, but flirted incessantly with her. He was a tit-man to the core, and leered openly at her bosom, while talking to her, especially when a bit of swell was revealed. Although slightly embarrassed by this attention, Dawn was also flattered, and was ripe for the picking.

When Gavin asked her out on a date, she turned to Hilary for advice, and ended up with a shorter skirt and lower neckline than she had ever worn before. Nervously, she invited Gavin in for coffee when they returned. She had never been alone with a man under such conditions. Within minutes, Gavin had his hands on her tits. She wanted to resist but it felt sooooooooo good. It did not take much longer for Gavin to have her top and bra off, and he gazed at those luscious orbs for the first time.

"Ohhhhh, they're gorgeous" he whispered breathlessly, as her buried his face in the soft valley.

Again she felt that she should resist, but then his lips found her coral pink tips and he nursed on them with a grown of pleasure. Dawn felt she'd died and gone to heaven... she had never experienced such divine feelings.

He dry humped his crotch against her exposed thigh, and she thrilled at the feel of his rock-hard erection. But on this occasion, she resisted him at last when his hands found her crotch, and the evening ended with her still a virgo intacta. But that night she relived the feelings of Gavin's hands and lips all over her breasts, and the pressure of his cock against her leg.

The second date was three days later, and her virginity was gone forever. In spite of the initial pain, it felt so good that she just knew she would want to fuck again and again and again. She was willing to give herself to Gavin wherever and whenever he wanted. Much to her surprise she found it quite a turn-on to be naked in his presence, as his obvious lust overpowered even her residual negative feelings about her body.

Two weeks later, he took her away for a long-weekend. They were at a quiet family cottage on a deserted stretch of coast. Gavin kept her naked for the whole time. At first she was a little shy and embarrassed, but gradually his obvious admiration of her curves made her feel increasingly comfortable, and she even started enticing him by spreading her legs or pushing her tits out at him. He introduced her to the joys of cunnilingus, loving the feel and aroma of her lush pussy lips. She couldn't believe how this could turn him on, but she exhilarated in the sensations. Then he taught her to suck cock and she understood. They screwed incessantly, night and day, missionary style, doggy style, with her on top. Dawn was now totally addicted to sex.

Back home, Gavin encouraged her to wear ever more revealing outfits, and she obliged, partly to please him but also because she gained an ever-increasing thrill in exposing herself. It was hard to believe that just a few weeks earlier she had been a rather prim and socially shy virgin. Although at the office she remained relatively conservative, when she accompanied Gavin to bars and parties her outfits became rapidly risqué. Skirts shortened to mid thigh. Matronly bras were replaced by flimsy garments that did no more than provide under-support, and were worn under short strappy tops.

Six months after their first date, Gavin asked Dawn to marry him, telling her that he'd love to see her pregnant with his child.

"It'll make me even fatter", she wailed, but in truth she was thrilled. She had often felt that her broad hips and enormous tits were meant to produce and to feed babies... lots of them.

Three months later they were married, and Dawn threw her pills away. But six months, then twelve months passed, and her periods returned as regular as clockwork every month.

Her gynaecologist could find no real problem, and suggested that Gavin should have a sperm test. But then Gavin told her his great secret. Three years before they had met, he had had a fling with a 15 year old schoolgirl, and had gotten her pregnant after just one burst condom. Her parents had threatened to lay criminal charges, and had only withdrawn the threat when he agreed to pay for her abortion and recuperation, and never to see her again. It had taken his life savings, and he was still cut up over the lost child.

So there could be no problem with his fertility! Dawn was devastated! Gavin comforted her, assuring her that she was still a very sexy woman, and that all his friends lusted after her. Perhaps she was designed to be a "sports model"

It was just as she was becoming reconciled to her barren state that Dawn's experience with exhibitionism took a quantum step forward at one of Gavin's poker games.

Gavin and a group of his workmates had a weekly poker school, and about once a month they met at the home of Dawn and Gavin. Gavin encouraged her to wear her most sexy outfits when she acted as hostess. They both got quite turned on by her being a sex object to his mates, such a different role to that of IT project manager and a diversion from thoughts of her inability to conceive. Their sex after his friends had left was awesome.

The talk amongst his mates was often rich in sexual innuendo, but Dawn became used to this and giggled at the comments, especially as she tended to have more to drink than she was used to. Then after one of these sessions, Gavin's boss Andy turned to him as he was leaving, saying: "So Gavin... When are you going to convince Dawn to allow you to play the golden chip?"

Dawn had no idea what this meant, but Gavin went red and muttered: "I... I... I haven't... haven't..."

Andy chuckled, clapped him on the shoulder and with a slight menace in his voice: "I think it's about time. Do it next time we're here".

"What's all that about?" Dawn wanted to know as soon as their guests has left.

"You'll get mad with me if I tell you", Gavin gulped.

"Try me!"

"What happens at a lot of our games is that the host gets a free pile of chips to play with. But he also gets the 'golden chip'. He can play that at any time, but usually only when he's getting low on regular chips. The golden chip covers all and every bet on that hand. If he wins, he gets the pot and his golden chip back. But if he loses, then his wife or girlfriend must strip off a major item of clothing before he gets another allowance of chips and the golden chip back. In fact, it is expected that she wear a dress, not a skirt or pants with a top, so that she is immediately down to bra and panties. Of course", Gavin tried to explain, "that's not very different to wearing a bikini."

"What if he goes bust again?" Dawn wanted to know.

Gavin gulped more loudly: "Th... The... Then... well, you know..."

Dawn, who was quite tipsy by now, giggled at his discomfiture. "So you want your wife to parade around in the nude for your mates?"

Dawn hardly admitted it to herself, but she was quite turned on by the thought of stripping in front of Gavin's friends. So, somehow, by the time of the next game at their house, both had accepted that they would play the 'golden chip' game.

Dawn bought her most daring outfit ever for the evening, a very short black cocktail dress with spaghetti straps, and with a low cut square front that showed lot of cleavage. She had to buy a strapless bra with good under-support, and the one she found left the upper swells of her breasts naked, with even the edges of her aureolae sticking out. She wore lacy black bikini panties, and completed her outfit high platform-heeled sandals.

Gavin's mates fawned over her, and found every excuse to help her with snacks and drinks so that they could 'accidentally' touch her. Andy was particularly forward, and boldly cupped her breasts from behind when he caught her on her own in the kitchen. To Dawn's surprise, she found herself getting aroused and at what point needed to go change her panties as they were so damp. The innuendoes became ever more bold, and she even joined in.

For some time, however, it did seem that Dawn might not need to strip. Gavin was doing well, and his pile of chips grew steadily. Then followed three hands in succession, in each of which he had a good hand, betted rashly, and lost. Then when he realized how much he had lost, he changed to playing cautiously and his pile of chips bled away. Just after 11pm, he played his golden chip... and lost, to cheers from his mates and their chants of "Take it off, take it off!"

Suddenly, Dawn was nervous, but knew that there was no backing out. She wanted to go to the bathroom, but the guys would have none of that. She had to strip there. With trembling fingers, she undid the catch, pulled down the zip, and stepped out of her dress to whistles and catcalls from the men, as they took in her barely concealed DD-cup tits, and the dark bush that was so evident between her legs, peeking out from the legs and above the top of her flimsy panties.

For two more hours, she served the men in this state of near-nudity and found herself close to orgasmic in arousal, especially as hands wondered across her legs and tits, some tweaking her nipples into hard points and others slipping fingers into her juicy slit.

As soon as the guests had left, Gavin ripped her panties off, threw her on the couch and fucked her right there. They both came almost immediately. They fucked the night away. Over the next week, they replayed the events by having Dawn remain naked all evening, fantasizing about guests looking at her, feeling her up or even fucking her as Terry watched.

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