# Gaining Confidence 1 - by Charissa (~BBW, Romance, ~MWG)



## Observer (Jul 11, 2006)

~BBW, Romance, ~MWG - an old friendship blossoms into something much more

*Gaining Confidence 1
By Charissa ​*
*Part One *

Jenny came in from work to change before meeting her best friend Luke in town. In her mailbox was a parcel addressed to her in the handwriting of her favorite aunt, a travel writer who often sent her presents from different places. It was squashy, and Jenny tore the wrapping off as she climbed the stairs. Inside were a pair of pink denim shorts and a cropped T-shirt with a number 1 on the front. 

Jenny's heart sank slightly, as she would have to write to thank Aunt Claire and these clothes weren't the sort of thing she would ever wear, she thought, changing from her loose blouse and long dark skirt to another long skirt and a baggy T-shirt. Far too tight, far too revealing. Even if she hadn't put on ten or twelve pounds over the last year, she'd never have considered them. 

Jenny was looking forward to seeing Luke more than she'd looked forward to anything for ages. He and Jenny had known each other since they were four or five, and though they were very different, had stayed close. They had never dated. Luke was outgoing and confident, and all through high school and college had always had troops of friends, and plenty of girlfriends, while Jenny was rather shy and self-conscious. People invited her to things because she was Luke's friend, but she knew that many of them thought she was a dull, frumpy little mouse, if they noticed her at all. 

If it weren't for Luke, she often thought, she would have had little in the way of a social life. Since Luke had decided, after their college graduation, to go on law school, Jenny had missed him considerably. She had landed a decent job with potential, working as an editor for a small publishing company, but sometimes felt she was not sufficiently confident to make a success of her career on her own. She worked very hard as a consequence, putting in long hours, and saved most of her pay - she didn't have time to spend it taking trips or going out - who would she go out with, anyway? 

As Jenny drew near to the café where she and Luke had arranged to meet, her sweet, angular face grew anxious; she hadn't seen Luke in so long, she almost couldn't believe that he would be there. She peered ahead to try to spot his familiar broad and stocky figure, and when she saw him had to hold herself back from breaking into a run; it was the first really warm day in June, and she was overheating slightly in her concealing clothes and didn't want to arrive all sticky. She pushed back her dark shoulder-length hair. 

“Hey, Jen! Good to see you!” Luke hugged her and then took a good look. “You look kind of tired; too many late nights partying?” 

“More like late nights at the office - the new job has some workload. It's so good to see you!” 

Luke called the waiter over and asked Jenny what she wanted. “Just a coffee I think. Don't want to overdo it - sitting at a desk all day, I don't get the exercise I used to in high school, and I already gained a few pounds.” 

Luke gave her a rueful grin. “I was hoping I could tempt you to some ice cream; it'd be more companionable 'cause I'm definitely having some…” 

Luke had a naturally chunky build, but had never let it bother him, and it hadn't put off the girls at high school and college; Jenny thought his blond hair and dark brown eyes were very striking. When he'd hugged her Jenny had noticed that since she last saw him he'd put on maybe another fifteen or twenty pounds himself, a soft curve of belly that stuck his loose shirt out slightly. But he's so tall and broad, she said to herself, he can take it. It certainly didn't detract from his charm. 

Jenny's coffee and Luke's ice cream arrived, and as he dug in she told him all about her new job and her worries for the future. It was such a relief, she felt, to talk to someone who knew her so well and was so accepting of her. She told him of the pressure she felt under to prove herself, and her need to take on extra work so as to show her colleagues that she was a valuable junior editor even if she was inexperienced and straight out of college. 

“It means I don't have much spare time,” she said. “I haven't been swimming or played tennis in weeks, and I guess it shows.” 

“I don't see any difference,” said Luke. “In fact you could stand to gain a few pounds, I've always thought you could use a few womanly curves! Anyway, nobody can tell what you look like under those clothes - aren't you hot, always so covered up? I remember you running round our backyard in just your panties - must've been a lot cooler!” 

“Yeah, Luke, but that was when we were six!” 

Luke was going to spend the evening with his parents, but arranged to meet up with Jenny again the next day. As Jenny walked home, she thought about what Luke had said. OK, maybe she wasn't actually overweight. She weighed about 125 pounds, which was twelve up on what she'd weighed a year ago, but hardly even plump. 

During high school and college, she had always been very skinny and never worried about her weight. She had worried about plenty of other things; her shyness and lack of confidence, her apparent invisibility as far as dating were concerned, but not her weight. Her figure was still slender, but rather boyish, with small breasts and hips not much wider than her waist; she did worry that she wouldn't have a waist at all if she gained any more. Most of the new pounds had settled around her stomach, which had become very slightly more rounded, but this was really perceptible only to Jenny. She could still only pinch about an inch or so of flab; it was her poor body-image which saw it as a major change. Luke hadn't noticed, after all. 

As she walked in the sunshine, she did feel hot. The dark skirt was way too warm for summer and sweat began to trickle down her legs and inside her T-shirt. She looked around at other women on the streets, and noticed that they were mostly wearing much briefer clothing than she was. Lots of teenagers were walking around in midriff-revealing tops like the one her aunt had sent. 

Jenny had thought you had to be a Britney Spears to get away with that, but the girls around her were not all perfectly toned by any means. Some extra flesh was the rule, not the exception. A blonde, bespectacled sixteen-year-old passed wearing tight jeans which created a tiny roll around her waist, while her friend, tall, dark-haired, creamy-skinned and probably a size sixteen or eighteen, wore low-rise shorts fitting round a much more substantial rounded belly, with a jewel sparkling in her navel. Her face was round, cherubic and serene. 

Jenny wondered at the girl's daring to show off so much flesh; didn't boys poke fun at her in those shorts, which clung to her big buttocks and heavy thighs, and showed off dimpled knees and chunky calves? Jenny wouldn't have felt comfortable in those clothes even at her thinnest, she thought. But this girl looked very much at ease, rounded, full and ripe, and her blonde friend looked almost scrawny beside her. 

It wasn't just teenagers either. A woman, maybe in her thirties, walked by wearing a shirt knotted up under her full breasts, revealing a soft, rather flabby abdomen. Faded stretchmarks were visible, presumably from a past pregnancy. Yet the general effect was not unattractive; more of a sexy, experienced woman than one who had “let herself go.” 

Further down the street, Jenny passed a pregnant woman in her late twenties, who was wearing a short skirt which passed under her prominent bump and a bikini top, nothing more. Her husband was holding her hand and gazing adoringly. Her belly was amazing; dome-shaped, extending nearly a foot before her, it looked rock-hard and shiny with suntan oil. Its tan proved that the expectant mother bared it on a regular basis. 

Jenny was compelled and tried not to stare as she passed, but the woman just smiled back at her confidently, evidently revelling in her new-found bulk, which she stroked gently from time to time. With her red hair and bluegreen eyes, she looked like a magnificent Celtic mother-goddess. 

Jenny realised that though the pregnant lady was a special case, the other women did not have hangups about putting a little flesh on display. 

“Who do I wear these clothes for?” she asked herself. “I've always dressed modestly - I wouldn't want to look slutty - but then these women don't look slutty at all, they look great. Even Mom wears short skirts now and again - I haven't had one shorter than calf-length since when? Middle school?” 

Pausing while the lights changed, on impulse she tried to tie her T-shirt up under her own small breasts, but it just fell back again. At that point she caught sight of a truly arresting woman. 

With her dark hair and eyes and olive skin, she had an exotic charm, and her face was beautiful despite its padded cheeks and opulent double chin, Jenny thought. She was wearing a loose scarlet skirt, whose gauzy Indian material flowed over fleshy legs, and whose drawstring was cinched gently under the largest belly Jenny had ever seen on display. 

This belly had ceased its journey outwards for the time being, and its swags of fat had begun to droop downward towards her knees; if there was a jewel in this navel, it had long since vanished in the distended cavern the navel had become. The stretchmarks on it had paled and widened. Visible beneath her short red strappy top was another hefty roll of flesh, big enough to merit the name “spare tyre” for real. It was at least eight inches broad and pushed the lady's soft, wide, dimply arms away to the side, aided by her love handles, of which she had quite a collection. 

Her hips, wider still than her two belly rolls, swayed beneath the skirt as she walked, slowly and ponderously, but not without grace. Underneath the halter-top, her ample breasts bounced in the same rhythm (as did her broad and pillowy backside). Her beringed hands and sandalled feet were as plump and dimpled as a baby's. Her abundant charms made the “Celtic goddess” look pale and thin. 

Jenny realised that she had been standing at the crossing through at least two changes of the lights. 

Wow. 

“Well, if a woman who has to weigh 300 pounds - or more - can let it all hang out,” thought Jenny, “what am I doing hiding in baggy, hot clothing? She must weigh more than twice what I do. Maybe I will try on those shorts from Aunt Claire when I get home.” 

When she saw the shorts, however, Jenny wondered whether she'd be able to get into them - she was still overestimating her own size. She wore a 10 normally, though she would have fitted into an 8 easily. The size tag on the shorts - 38 - was no help, as it was European and Jenny didn't know what its American equivalent was (usually an 8). 

She looked at the reverse and saw it said “Taille 60cm” - 24-inch waist. She thought that was about what she was - maybe a little smaller, or bigger. Remembering the girl in tight jeans, however, she unzipped her skirt, stepped out of her slip and drew the shorts up her legs. They were certainly more fitted than she would have chosen herself, not to mention shorter and lower-cut in the waist, but she had no difficulty fastening the zipper; they were even a little loose. While she was at it she put the cropped T-shirt on too, and took a look in the mirror. 

She saw a girl - not a woman - who looked much younger and more carefree than the covered-up self she usually saw, with about five inches of creamy midriff visible beneath her T-shirt. The shorts came up just under her navel, and though they didn't create rolls like the blonde girl's jeans, it was just noticeable that her stomach was convex rather than flat below the waist. 

Her breasts, usually lost under loose blouses and baggy T-shirts, could now be seen in outline, small and perky. Her arms and legs were smooth and slender - and the arms were more tanned than the legs. Jenny wasn't sure about the general effect - she looked younger and more sexy than usual, but still wasn't convinced that she wanted to. She changed back into her usual clothes, and went to make a salad for dinner. 

Nevertheless, when she got up the next morning - a Saturday - she decided to put on the shorts and T-shirt to go and meet Luke in the park. They were suitably casual, she told herself, and would be cool, and Luke was surely the safest person to try out a new look on - he wouldn't jeer at her (in fact, being a man he might not even notice). She trusted him implicitly, and besides, he had seen her in her panties even if it was 17 years ago! She rubbed on some sunblock and ran out of the door.

(Click here for next installment)


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## zonker (Jul 12, 2006)

Oh man, this is one of the best stories ever. Charissa, you just make me swoon with your descriptions... It's great to see this old favorite again.


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## Heidi (Nov 29, 2006)

Has there ever been a follow up to this story? Is there an intention to write one?


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## Observer (Nov 29, 2006)

Yes, as noted in the story there are actually eight more installments - with everythiung else going on I had frankly forgotten about this one. I'll see what I can do later tonight or tomorrow.


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## Heidi (Nov 30, 2006)

Looking forward to it!


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