Libby's Liberation Ch. 01

Story Info
A stuffy conservative's liberation, via Literotica.
5.2k words
4.29
44.6k
13

Part 1 of the 5 part series

Updated 06/08/2023
Created 06/01/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Such a funny thing, how very wrong one's perceptions can be.

Case in point: our very good friend, Elizabeth Stanton. She's a funny girl, our Libby: very stiff-upper-lip, born-with-silver- spoon-in-gob, haughty and snooty and how-to-do. She's the very definition of a rich snob: delightfully misanthropic, wickedly xenophobic and extraordinarily blinkered to the workings of the world in general. She is very nearly a caricature of the upper class -- yet somehow, she still manages to be fairly likable.

Despite her long list of shortfalls, she's not all bad. She is kind and loyal without fail to her friends, most notably to my wife (through whom I came to know our Libby), and there's something about the way she states her profoundly right-wing old-school beliefs that amuses rather than offends. Her being in possession of a fairly pretty face and long flowing blonde hair, along with a nice-and-tidy gym-honed body, shapely rump and generous bust probably helps in this department.

Not that I have ever held any seriously lecherous desires towards our Libby. I love my wife, you see, and I'll be forever loyal to her. And while Libby's behaviour is amusing in short doses, I've found myself over the years feeling sorry for her many and varied man-friends; it seems to take only a few weeks with Libby before they develop that pained, hounded, 'why-God-why' expression that marks a man as Libby's Current Beau.

So it came to pass one day -- ten years into my marriage and thus ten years after having first met our Libby -- that Libby came to stay with us, following the dissolution of yet another relationship with a live-in boyfriend. His tolerance of her whimsical (and not always faithful) ways had finally run dry, and to my secret amusement and admiration he had run her out of his house, depositing her furnishings and belongings in the front yard in a less-than-gentle fashion.

As often is the case in this situation, our Libby came to my missus for solace and comfort; and as has increasingly become the case since I made my millions and foolishly purchased a six-bedroom mansion half-way up a picturesque mountainside, the missus declared that of course Libby could stay with us while she sorted herself out. My missus's generosity knows no bounds. Especially when it comes to her generosity with my house, my belongings and my money. I still love her, though.

On one particular sunny summer's day during Libby's stay, with the missus gone to work and the kids gone to school, I had assumed my traditional work-day pose: parked in a sun-lounge by the pool, with a large pitcher of Long Island Iced Tea to help me brace for another hard day's work, and a laptop standing by should I feel the need to actually achieve anything. Life's hard for some of us, don't you know.

Hardly had I poured my first tall glass when Libby graced the scene, clad scantily and alluringly in a skimpy bikini and a sheer wrap-around sarong, which was hitched in a petite knot just above her shapely hips. "Well hello, Tom," she greeted, pulling her oversized sunglasses down to peer more obviously at my refreshments. "We're starting on the booze early for a Monday morning, aren't we?"

"Not at all, Libby my dear," declared I. "I find a few good 'Long Teas' are essential to brace against a busy week."

"Can I assume the spare glass is for me?" she asked.

"Either you or the poolboy," I grinned. "First in, best refreshed."

And so the drinks were poured, my laptop was ignored, and as we drank Libby and I talked about various banal trivialities, most of them involving herself. She is awfully good at talking about herself, our Libby. For shits and giggles I steered the conversation onto the topic of her latest break-up, trying to ascertain what level of blame -- if any -- she was willing to apportion herself.

"Oh Tom -- I just don't understand men," she said sadly. "I mean, Glen and I --" Glen being her most recent boyfriend "-- Glen and I were going so well! And then he just turns around and throws me out of his house! I just don't understand," she said again, punctuating her profundity with another sip of long tea.

"Could it have had anything to do," I ventured, "with your 'dalliances' with his best mate?"

"Oh Tom: really," she scolded, disapprovingly. "Now I know you and Kelly --" Kelly being my wife "-- you and Kelly store great stock in loyalty and faithfulness and all of that. And I think that's great," she added, in a terribly condescending tone that I just had to grin at -- as though she was declaring a toddler's few smears of blue paint on a crinkled canvas an artistic triumph. "That's really great," she reiterated. "But for some of us, a little bit of hanky-panky isn't really that bad. And it's not like I blew up when he kept going back to his ex-girlfriend for a bit of 'reminiscing'," she added.

"Oh no," said I, by way of agreement. "No no, you didn't blow up at him at all -- but me and Kelly heard all about it. And bloody ad-nauseum, too."

Libby's jaw dropped in mock outrage. "Tom!" she scolded, throwing a slice of lemon at me. "You know, you get quite the wicked tongue when you've been drinking."

"As opposed to you," I returned, "whose tongue turns positively saintly after a few brews."

"I don't hear too many complaints about my tongue, thank you," she said, with an immodest grin. "In fact -- have I ever told you about the time Glen said I should have my mouth insured?"

"Actually, yes you have," said I -- Glen's declaration referred to Libby's apparently priceless skill and ability at the fine art of fellacio. "You are simply too modest for words, Libby," I added.

Libby grinned, but it was a short-lived grin as she returned to her moody broodings. Her eyes fell to her own chest -- as they so often do; our Libby has forever been clearly and obviously infatuated with herself and her body, taking any and every opportunity to make eyes at her own reflection, or peer down her own cleavage, or occasionally even run a finger up and down her inner thigh when she (wrongly) thinks no-one is looking. Lord knows how she gets anything done when she's alone with herself; if God truly does kill a kitten every time one masturbates, then Libby must have a million dead cats on her conscience.

"It's because of my boobs," she suddenly said, which threw me somewhat from my thoughts of mass felinicide.

"How's that?" I said, spluttering from a little bit of inhaled long tea.

"Glen's ex had the biggest boobs," she explained. "He probably let her get away with anything, with tits like those. But poor old Libby, with these little puppies..." she said, grabbing her bikinied bosom and giving them a sad little jiggle "...there's no leeway for me."

Well, I thought. What was there to say to that? Libby's tits were by no means little or puppy-like; she was quite generously equipped with nicely round and fulsome C-bordering-on-D cup-fillers, and crammed as they were into her C-sized bikini top they were most pleasing on the eye. But even as she started saying "...maybe it's time to start saving up for the surgery... how much do fake tits cost these days?" I found myself wondering: how best to console Libby, and assure her of the perfect adequacy of her breasts, without crossing the line?

"Come on now, Libby," I scolded. "Let's have no more of that talk. Speaking as a guy, and as your friend -- and the husband of your best friend," I added, to dispel any possible dodginess ahead of time, "I can assure you that your tits are really, really nice."

Libby's face broke into a smile of relief. "Really?" she asked, heartened.

"Yes, Libby," I promised her, in as reassuring and brotherly and platonic a fashion as possible. "They really are a top pair. Don't you even think about putting them under the knife -- surgery would ruin them, they're already perfect as they are. Okay?"

"Okay," she nodded, visibly gladdened by my reassurances. She took a big sip of her long tea, as though she were steeling herself, and she put it to me: "Would you like to see them?" she asked, hopefully.

"See what?" I asked, frowning slightly.

"My tits," said Libby, brightly. "I'll show them to you if you'd like..."

My shoulders fell. 'Yes. Yes! YES PLEASE!' was the response issuing from my pelvis; 'No, no, I can't,' was my more rational, cranial response.

I sighed as I looked at her. I knew Libby wasn't being lecherous in the strictest sense, or intentionally disloyal against Kelly my wife in offering to flash me; she was just looking for affirmation, for a reinforcement of the support and encouragement I had already given. But I knew I couldn't let her do that. To agree, to say 'aw, okay, go on, show em to me' would be lecherous on my part, very lecherous -- I'm not that great a guy that I could let a girl show me her breasts only to help her feel better about herself. And if such a guy exists, I'd advise him to check himself for a pulse.

So I thought quickly, and came up with a way out of this moral quagmire that would leave the both of us relatively clean. "Now Libby," I said, gently. "You don't really want to show them to me, do you?"

"Well..." she said, reaching hesitatingly for the clasp on her back, making her breasts stand out and say 'hello!' in a fashion I tried desperately to ignore. "Kind of..."

"No you don't," I told her, kindly. "You just want to show them to 'somebody', don't you? You just want somebody, anybody to have a look at your tits and go 'phwoar!'. Don't you?"

Libby's face fell, and so did her arms, letting her breasts -- and myself -- relax. "I'm sorry..." she murmured.

"No no!" I quickly told her, before the tears came. "It's okay, Libs! It's fine, I understand. I get that way too, sometimes," I assured her. "Lots of people do. You just have a bit of an exhibitionist streak in you, that's all. You know what I mean?"

She looked at me, thinking on what I said. "Aw," she began. "I'm not sure about 'exhibitionist'... I mean, I'm not a deviant or anything," she added, lending a specially vindictive emphasis to 'deviant': making it sound as though these naughty exhibitionistic deviants were the scourge of the earth, hiding behind every rock and tree, prepared to leap out upon unsuspecting villagers and do wicked things to them.

"No, of course you're not a 'deviant'," I grinned. "But we all have a bit of that compulsive streak in us, you know? In all of us there's a little part of us that wants to show off our assets, to whip out our tits or our cock and ask a passer-by 'excuse me? Um... what do you think? Are these alright?' You know?"

Libby nodded along. "Yeah, I guess..." she allowed. "But what can I do? I'm sorry I asked you, Tom, I shouldn't have done that... you're my best friend's husband, I'm so sorry..."

"Water under the bridge," I assured her, as I reached for my laptop with its wireless modem. "But there's still hope, Libby. Let me show you this." She hopped up and came to sit with me, and I loaded up literotica.com and showed her the Amateur Photography forum, explaining to her how it worked and showing her a few threads to give her the general idea.

"Wow," she said, eyeing off some of the good-looking ladies I had loaded up for her.

"Yeah," I grinned. "So basically: if you're looking for a bit of affirmation, a bit of praise from random people all over the world, all you've got to do is take a few pictures of yourself, post them in your own thread, and let the good people lay their opinion."

"Do you think they'll like me?" she asked.

"Again: speaking only as a guy and as your friend," I began, "with your body: you'll be right up there with the hottest chicks. They're gunna love ya!" I promised her. "And all the guys and gals on literotica are very nice and really supportive: I promise there won't be a single negative thing said about you."

"Okay," she nodded, a smile morphing into a grin as she warmed to the concept. "Okay! I'll do it! Do you have a camera?"

"Right here," said I, reaching into my laptop bag.

"Alright," she beamed, and she reached back again for the clasp on her bikini -- my eyes widened.

"Whoa whoa whoa!" I cried, stopping her only just in time: the straps were undone and the top was half-way gone, the cups clinging precariously to Libby's breasts and only barely maintaining the mystery. "If you'll just give me half a second," I added, as she stared at me, wide-eyed and frozen, "I'll show you how to use the auto-timer."

She let this sink in, and then she laughed a little with embarrassment. "Sorry," she said, and I turned away graciously (if a little reluctantly) to allow her to reposition her top. "But still," she added, "I'm going to need your help to load it all up for me, and start all these 'threads' and stuff for me -- I'm not really very good at that sort of thing. And besides," she added again, and as I turned back to look at her with her top safely resecured, I saw she was grinning, "do you really expect me to believe you'll never look at my photos?"

I blinked -- she had me there. Loyal to Kelly as I might try to be, I knew there was no way in hell I could stop myself from checking out Libby's photos. I simply was not that strong a person. "Okay, you've got me there," I allowed, with a goofy grin. "But still: I'm sure you'll agree it would be better if you take the photos yourself. I'll look at your pics -- only to help you load them up, of course -- but it's best if I don't see your bare bits in person. You know?"

She was still grinning at me. "Fair enough," she agreed. "So: what do I do?"

I explained the auto-timer function to her, and gave her a few photography tips from what I had seen in the site's amateur photos: "Focus on your body, not your face -- we'll crop and trim the photos so they don't show your face, it's not a good idea to give people a chance to identify you. Get a few pics with your bikini on, maybe a couple pics as you're taking it off, and as many pics from as many angles as you like with your goodies out -- the camera's got lots of memory, and we'll only post the best shots," I assured her, as she nodded along. "And you only have to show as much or as little as you like -- there's no rule saying you have to show your pink bits or anything."

"Oh, that's good," she nodded, with relief. "I'd probably like to keep that to myself. At least for now..." she added, with an alluring grin.

I pulled a face. "I'll probably let you trim and crop those pics yourself," I told her, more for my own sake than hers. "Anyways: here's the camera. Run along to your room and go nuts."

"Does Kelly know about this site, Tom?" Libby asked, suddenly and out of the blue.

I paused, and looked at Libby as she beheld me: camera in hand, bikini and sheer wrap set to come off, body pert and lovely and soon to be forever immortalised on the interweb. "Frankly: no, she doesn't," I sighed. "See, I like to post the odd erotic story up on Literotica, but when I told Kelly about it she thought I was a weirdo, so I told her I'd stop."

"But... you didn't stop, did you?" Libby asked, with a grin at my naughtiness.

"No..." I allowed. "I slowed down, though. So obviously, I'd prefer if we didn't really mention any of this to Kelly."

"Gee, Tom," said Libby, in a surprisingly beguiling fashion. "We're sort of dabbling in a bit of a moral 'grey area' here: me showing you pictures of my naked body, you posting them on the net for me... Are you sure you want to do this?" she asked me, fixing me with a gloriously wicked smile that, I must confess, provoked a stirring in my shorts.

I returned her look with a raised eyebrow. "Are you sure I should be asking that of myself?" I rejoined. "Otherwise you'll have to load your own pictures..."

"Okay, okay," Libby allowed, heading off with the camera.

"Or if you can't figure it all out," I called after her, "you'll have to hire a hot-air balloon and drop pictures of your titties all over the town..."

"Okay, okay!" Libby cried, shooting a grin at me as she left.

Thus commenced perhaps the longest half-hour of my life, as I awaited Libby's return with more than a little anticipation. Yes, okay: strictly speaking, it wasn't entirely kosher, helping Libby out with her exhibitionism and checking out pictures of her in the buff. But, I reasoned, it was better than the alternative -- namely, letting her parade around naked in front of me; that way was fraught with temptation, and all righteous intentions and loyalty to my wife aside, I am only human -- who knew where such close-range hanky panky might have led? And I felt I was due some kudos for exercising massive restraint in not taking the pictures for her -- it was more than just a little tempting, let me tell you.

So I whiled away the time by checking out a few of my favourite Literotica-girls -- well, seeing I was already on the site, may as well, eh? -- and then I took a bit of a dip in the pool to cool down my ardour before Libby's return; a giant bulge in the shorts was not how I wanted to welcome her back. As I was towelling off, Libby came back: bikini and sarong back in place, clutching the camera preciously. "How'd you go?" I enquired.

"Pretty good," she reckoned, looking happy. "It's a lot of fun, actually! I wish I'd thought of this sooner -- of course there'd be a site like this on the internet," she declared.

"Alrighty -- shall we load them up and see how they look?"

"Let's do it," she affirmed, without a moment's hesitation.

So we sat side-by-side on my lounge as I plugged the camera into my laptop. "Righto, Libs: talk me through," I invited. "Tell me what you want to post and what you don't."

"Well, the first ones are of me with my bikini still on," Libby explained, as we looked them through. "But I couldn't keep my face out of the shots -- can you fix that?"

"Easily," I declared, cropping and trimming a few so that only her comely body remained. "How's that?"

"That's great, Tom! Now these ones," she continued, as we flicked onwards through the series, "are your suggestion: gradually taking my top off."

"Ah," I said approvingly, lingering on each pic: the first one was what I saw earlier, her reaching back to grab the clasps, her shoulders arcing back and her breasts standing out, round and proud and fulsome. The next pic: the clasp was undone, the straps were coming forward, but the shoulder straps remained in place and so did the cups.

I slowed down in moving through the pictures, taking time to linger and dwell on each one: the next, she had reached up for one shoulder strap and had pulled it down slightly, revealing a tantalising piece of her bare upper chest and shoulder; the next, the other shoulder strap was coming down, her other hand holding the cups to her breasts, though one cup was coming away slightly, revealing the creamy softness of the curve of her breast...

"You like so far?" she asked.

"Oh yeah..." I assured her. I tried to think only like a guy, just any random guy, looking at any random girl: I wasn't looking at pictures of my wife's best friend getting undressed, I was only looking at some random chick. As I trimmed and cropped her face out of each pic, I noted the look on her face: so far her eyes were cast downwards, surprisingly humble and demure, but with the next pic -- as she let the cups fall slightly, exposing more of those wondrous breasts but not yet the whole thing -- her eyes were suddenly raised, looking to the camera: enquiring, beguiling, asking 'you like what you see, don't you?'

"Wow," I said.

"They're good?" she asked, looking to me.

"They're great..." I breathed, no longer able to feign a detached interest. "Libs: you've done a slow strip-tease! I love when they do that! And I didn't even suggest it -- you did it all yourself!"

"You really do like it, don't you?" she grinned. "And you haven't even seen the whole thing yet!"

12