OMG!

Story Info
More like demolishing her cherry.
8k words
4.29
17.4k
9
0
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

Tears prickled in Karyn's eyes, as she stared, confounded, at Isla and Devon. Standing hand in hand, they'd just dropped a bomb on Karyn's ordered world. Her suddenly ex-fiancé and her supposed best friend had just informed her that they, Isla and Devon, had 'accidentally' fallen in love. What was really odd, Karyn thought, was that it had almost immediately dawned on her that her tears were tears of shock, not tears of sadness. Go figure.

Karyn and Isla, had been best friends--BFFs--since primary school. In high school, Isla had joined Karyn in taking a vow of pre-marital chastity: 'virgins till we wed.' Then, soon after taking those chastity vows, Isla had gotten herself a steady boyfriend, and, in relatively short order, had lost her virginity, or, perhaps more precisely, surrendered up her virginity. Having found the love of her life, she had succumbed, rather quickly, to the boyfriend's incessant, insistent whining, coaxing, and cajoling.

If not initially impressed, the young couple had discovered during their second or third go that they really quite liked sexual intercourse. Isla had told Karyn about it--in turns delighted and nonchalant, as if it was no big deal. Still, she'd been excited to share details with her BFF. "And when you have an orgasm, it's real, real nice; even better," she'd whispered, "than when I get there--by myself--with my fingers--at night." As she had spoken, Isla's hands had crept, one to her breast, one to her crotch, her gaze getting dreamy, staring off for a quiet moment before she'd gathered herself once more. "You know what I mean?" It was more of a statement than a question.

Well, Karyn knew how to masturbate to climax. Isla's description hadn't sounded all that special. Indeed, Karyn remembered thinking, she'd hoped, when she finally experienced it, that it would be much more remarkable that that. The sex that Isla hinted at was always very vanilla--very conservative. Eventually--as with most first, serious relationships--her boyfriend, Brad, had broken up with her. When he left her "for that slut, Penny!" Isla was devastated. To add insult to injury, he had told her that she was just too boring.

Isla had wept for days on Karyn's shoulder. Brad had deserted her, exposing her injured self-esteem, and leaving her to the vultures. Without his love, or her honour, as it were, she was both vulnerable and available. And while Karyn had never brought it up with Isla, she had thought to herself, "So, you broke your vow of chastity--how's that working out for ya?" But Karyn certainly wasn't one to judge. And surely crying over lost virginity was as pointless as crying over spilt milk.

So, here they were, some months later; and the admission of Isla's betrayal came as a shock. Isla had tried to explain herself in an apparent bid to be understood, perhaps forgiven; and once started, her confession flooded out.

"Honestly, I didn't set out to steal your fiancé;" "I didn't mean to ruin your plans;" "I didn't want to hurt you;" "I never intended to take Devon from you. It just happened." Isla was, in fact, overly apologetic.

"Isn't it funny," Karyn thought, in an odd, objective observation as her best bud prattled on, "While she talks about making love, not once, so far, has she mentioned the word sex--not once has she come out and actually admitted to doing the dirty deed--to fucking my fiancé--my ex-fiancé."

Notwithstanding, it occurred to Karyn that Isla's explanation was fast becoming a case of TMI. Still, Isla continued, claiming she felt badly that she had abandoned Karyn--in her stand for virginity.

For Karyn, things started to become a little clearer. A while ago, Isla had been offering gentle encouragement, to convince Karyn to relent, and try sex. Originally, ostensibly, it was so her dear friend would be able to hang onto Devon--soothe his doubts. But later, Karyn figured, it was more to do with Isla wishing to assuage her own guilty conscience--all to no avail.

Although Karyn and Devon had mutually agreed to remain virgins until they wed, Devon had begun to confide in Isla that he was not sure he wanted to wait. Karyn looked up at Devon, while Isla continued, and muttered, "But, you never shared your doubts with me." He couldn't meet her gaze, as she whispered, "I wonder why." Over the background noise of Isla baring her soul, Karyn recalled how she and Devon had, at one point, done some erotic manipulation--she handling his cock and he, her tits. But they'd agreed--mutually, she'd thought--that it was all just a little too tempting.

Soon after that, it would seem, Isla became a friendly shoulder for Devon to unload upon. And, from Isla's rambling account, it wasn't long before Devon and Isla had 'accidentally'--completely unintentionally, you understand--ended up in bed having relations--ie. fucking.

Although, Isla still insisted, even then, that it was making love, not just having sex, she, nonetheless, basically admitted that she had really missed the sexual aspect of having a boyfriend since Brad had dumped her. In any case, when it happened, the two of them, Isla and Devon, most definitely liked it. And, once his cherry had been popped, they both figured there was no point in refraining.

He didn't, of course, tell Karyn he had given up his virginity. Instead, he started an affair with--started regularly making love to--Isla. "Making love," Isla explained--as if Karyn couldn't possibly know, as she hadn't, as yet, had any first-hand experience--"is so much more than just having sex." She went on to describe climaxing as "really nice, a real pleasant part of making love." The errant couple got together, as it turned out, once or twice a week--always on a bed, always in missionary position, and always in the dark. It sounded to Karyn, just a little bit dull--but who was she to say.

And while Isla was explaining all this, Devon just stood there--mute, eyes semi-glazed, holding Isla tight against his side. When she finally stopped--catching her breath, watching Karyn closely, as if waiting for some sort of response, Devon suddenly began to sputter and hem and haw. Karyn, somehow, just knew what was coming; just knew that he was trying to figure out how to diplomatically ask for his ring back. Even as unhappy as she felt--or as she felt she ought to feel--Karyn found his discomfort--his ineptitude--amusing. So, she came to his rescue, numbly removing her diamond and handing it back. Unexpectedly, a pang of longing and loss struck her as she watched him take it. She seemed to have had it such a short time.

Furthermore, it didn't even surprise her when Devon had the audacity--or the idiocy, depending on your point of view--to say, as he and Isla turned to go, "No hard feelings, eh?"

"Well," Karyn thought, pragmatically, "the wedding will need to be canceled--obviously. Not that there has been all that much actual planning done, so far. I mean, geez, we really haven't even set a date, yet."

In retrospect, Karyn was stunned, gobsmacked, even; but not as much as she thought she ought to be. Curious, that! As she watched them disappear out of sight, she realized that, in spite of it all, she expected her friendship with Isla would ultimately survive.

As she turned around and shut the door behind her, it also occurred to her that she had hung onto her virginity but lost Devon anyway. Now, as, in a way, the shoe was on the other foot, in fairness, she had to rhetorically ask herself, "How has that worked out for you, eh?"

The following Friday found Karyn at the local watering hole, happily surprising some of the old high school crew with her appearance, and being invited to join them. She had a marvelous time, drinking and dancing, and dancing some more--with strangers and acquaintances. She didn't drink too much, though. She didn't need to drown her sorrows. Also, she was cognizant of the wisdom of maintaining her awareness. She'd heard stories: spiked drinks, drunken coercion, etc., etc.; hadn't everyone? Notwithstanding, she danced with abandon--with pretty much anyone who asked, and, though not sure why she felt as she did, she enjoyed herself far more than she would ever have expected--far more, she believed, than she would have with Devon.

After that, she found herself at the bar with the girls, two or three nights a week, joining whomever happened to be there from the old gang. Always welcomed, she soon became just one of 'the girls'.

Karyn didn't realize, not consciously, anyway, that she radiated an erotic allure, a sort of sexual availability. However, she was aware that she felt a kind of hunger that she had never before felt; she also felt a lot of hard-ons during the dances. She knew she tolerated a lot more tight squeezes and grab-ass than she ever would have in the past. And, actually, she was surprised, if somewhat pleased, at the number of soft hits she'd had to fend off. It was kind of fun, really.

A few weeks into her new social routine--her new appreciation of local night-life as entertainment, Karyn accepted an invitation to an upcoming party--at Marcie's, an old classmate, recently reacquainted. Back in high school, the goody-goody girls, of which Karyn was one, considered Marcie to be a slut. Now, these years later, Karyn found her to be friendly and vivacious; someone she was coming to really like. Marcie had virtually insisted Karyn come to her shindig--"Bring an escort... or not!" Karyn was still just becoming familiar, once more, with most of the people who would be at the party, so she had driven herself, and arrived solo. And that was all right, as, although there were some couples, it seemed the majority of people there were currently single.

At some point, when the party was well underway, and Karyn found herself just standing to the side surveying the crowd while sipping her drink; a smile landed unbidden on her lips. Yes, getting hit on felt good, really good; and it did wonders for her ego.

While circulating, as a good host should, Marcie stopped next to Karyn. "Karyn, dear. So glad you could make it. What's got you grinning like the cat who ate the canary?"

"Oh, just thinking."

Checking out the view--the party from Karyn's point of view, Marcie waited for Karyn to continue; but when she remained silent, Marcie turned to face Karyn, and was intrigued by the dreamy twinkle in her guest's eyes. With just a slight sense of impatience, Marcie turned again, and beckoned to a fellow standing nearby. "Hey, Troy. Karyn here needs to get fucked. Can you help her out?"

Karyn went rigid. Her eyes flew open wide, and her jaw dropped. Shocked into temporary silence, she couldn't believe what she'd heard. In a deep, round voice, smoothed with amusement, the fellow guest replied, "Oh, I'm sure we can do something about that." He--Troy, apparently--then, took Karyn's elbow and guided her, peremptorily, towards the stairs.

Suddenly giggling giddily--almost hysterically--Karyn gasped over her shoulder as she was authoritatively ushered away, "Marcie!! Don't be so crude!" Still, she let herself be led, like a lamb to slaughter, up the stairs, and down the hallway to the end door.

"C'mon kid, keep up," the fellow said, with just the slightest hint of condescension, as he aimed her--somewhere between showed her and shoved her--into the empty bedroom. "We can have our bit of privacy here--not to mention," he chuckled, "a decent size bed."

Karyn knew what was about to happen. She couldn't believe that she was finally giving in, and giving her cherry to a hunk she'd just met and to whom she hadn't even been properly introduced. Head spinning, still giddy, she flopped onto her back on the bed, and waited, uncertain. Watching through her eyelashes, with a bit of a glazed look, she had to admit, he unquestionably was a drool-inducing hunk--big, dark, and macho; in his mid-30s, with almost unfashionably long, dirty blonde hair.

She stared with intention as he unzipped and fished himself out. She thought that he looked rather large--huge, in fact; but then again, she had very little basis of comparison. Still, what Karyn couldn't get over, was how much bigger he seemed than Devon. Indeed, Troy was exceedingly proud of his ten-and-a-half-inch cock--an actual 10.5", when measured erect--and thick as a beer can.

(Metric system or not, around here, cocks are always measured in inches. Especially erections.)

He had a predatory grin, as he pulled his member free of his fly-front and gave it a shake. Then, without warning, he reached in and tossed Karyn over onto her chest. Spreading his jeans open and letting them hang off his butt, he grabbed Karyn's hips and levered her up. Flipping her skirt over her buttocks, he pulled her back to the edge of the bed. "Stand," he commanded, dropping her feet onto the carpet. "Bend at the waist. Lean onto your forearms, on the bed."

With hardly another sound, save for a couple of heavy inhalations and hissed releases, he stepped between her legs, and yanked the crotch of her skimpy panties aside, audibly stressing the stitching. Before she could figure out exactly what was happening, Troy split her puffy lips, and entered her, punching into her virginal cunt. Karyn moaned loudly, though she refused to cry out or yelp. Athletics had long since torn her hymen, and, indeed, her anticipatory arousal had her fairly well lubricated; still, it hurt like hell! The first couple strokes, had him fully inserted. After the briefest pause, he began pound--in and out, with no hint of consideration, his hips slapping loudly against Karyn's butt-cheeks.

Initially, Karyn felt completely disconnected, as if she were viewing the whole event objectively; however, the pain and shock of the assault fairly quickly began to morph into something else--some novel kind of arousal--without any pain at all. As this Troy guy remorselessly probed her depths, Karyn felt only a curious fullness. But that changed, too. Suddenly, through Troy's soulless, mechanical pounding, Karyn could begin to appreciate some marvelous sensations--flooding into her awareness, and quickly inundating her consciousness--sensations she had never before experienced. She was, soon, more aroused than she could ever remember being. And she recognized the signs of a germinating climax; not to mention that the sensations were so incredibly more intense than anything she had ever known masturbating--the only orgasms she had ever experienced. She couldn't believe how turned-on she was. She felt like she might explode. The orgasms Karyn had had on her own, in the dark, after a date with Devon, were, she realized, pitiful and pallid in comparison to the building delight she was enjoying right then--and she hadn't even climaxed yet.

Then the guy--Travis or Troy or whatever his name was--slammed himself deep, deep into her, and held himself motionless, while his truncheon shuddered and jerked, and washed her grasping cunt with spurt upon spurt of liquid warmth, pushing her to the edge of the promise of a humungous climax--to the edge, but, given his insensitive pounding, not quite over. Once he'd stopped twitching, after the last couple of squirts, he simply pulled out--leaving Karyn teetering on the cusp of something wonderful, and hissing, "No, no! No, no, no...." She was so-o-o-o close; the prize had been right there, in plain sight.

Karyn felt cheated--incredibly disappointed, and dissatisfied. Suddenly empty, her hips unsupported, Karyn collapsed forward, onto the bed. Her fucker casually leaned over her, grabbed a Kleenex, and wiped off, before putting his softening pecker away. "That was great," he said, flippantly, then turned, leaving her sprawled on the bed. Exiting the room, he threw an insincere, "Thanks, kid," over his shoulder, closed the door on her, and was gone.

Karyn muttered, "What a boor!" Left at sixes and sevens, she felt a new level of frustration. She now realized, with a wry grin, what was meant by, "Wham-Bam-Thank-you, Ma'am!"

She took a while to get her bearings. Her whole body was tingling--quivering. Although she hadn't got there, her arousal had heralded something much more exciting than Isla's "really nice, pleasant" description of climaxing. And she wanted to find out more.

Before descending back to the main floor, Karyn adjusted her panties, pulling the sodden gusset from between her swollen lips and spreading the now stretched material loosely over her pussy. She dropped her skirt, and, straightening her hair, rejoined the party inconspicuously, if rather distractedly, from the stairway--the razor-edge of arousal slowly dissipating.

Straight away, she got another drink, then forced herself to mingle, chatting with a few of the people she knew--and a few she didn't. She thought she'd managed to cover her preoccupation fairly well--at least, she hoped.

After a bit, another fellow she didn't know, sidled up to her and began to chat her up, liberally sprinkling his conversation with innuendo. He introduced himself as Mark, and casually remarked that he had, earlier, seen her, with Troy, disappear up the stairs. Later, he'd seen Troy appear at the bottom of the flight, with a self-satisfied smirk on his lips. Then, a bit later-- only a short while ago--he had seen Karyn, herself, appear looking somewhat befuddled. After mercifully little inane small-talk, he cut to the chase. "If what I've heard about Troy is true," he grinned, conspiratorially, "I'd guess that was a 'well-fucked' look!"

"Well, fucked, anyway," Karyn muttered, barely audibly. "I don't know about 'well'."

"But, did you have fun?" he asked.

She was surprised to hear herself respond, "Not as much as I had hoped."

"Oh, sorry to hear that. You deserve better, I think. I could, maybe, rectify that. Wanna take a chance on me?"

Turning, Karyn eyed him appraisingly. He was short and stout--Mike or Mark or Mick or whomever--shaped like a fireplug, she decided; with close-cropped hair, twenty-something, like herself.

"I'll bet I could ring your chimes!"

"Not really boasting," Karyn decided. "Just informing."

Cautiously taking her hand, he held it against his boner, and said, "Maybe you can help me get rid of this!"

Karyn simply nodded, and allowed herself to be guided back up the stairs. Mark steered her into the second bedroom, as the first seemed to be occupied. He lowered her gently onto the single bed. "Better than the back seat of a car!" he chuckled, adding, "lol!" and began undressing--tearing his clothes off, almost frenetically.

As his member was revealed, Karyn was intrigued. His penis was short and thick, sort of like him. And it didn't, at first, appear to be that much bigger than Devon's--maybe six inches long--but as she watched, she could see it noticeably thickening and stiffening. Karyn unconsciously reached over to have a feel. As she grasped the beast--well, well, then there was no comparison. It felt as big around as a beer can. She was reluctant to let go. Mark stood, still for a moment, between her legs, as she stared at the growing hard-on in her hand--squeezing and stroking it, tentatively.

"You like, Sweetheart?" He raised her to her feet and tilted her face up, leaning in to kiss her. While Karyn found herself eagerly returning his kisses, she didn't let go of his erection.

Mark's kisses rapidly devolved into simply sucking face: "But at least it's foreplay." He tended to rush through the preliminaries, but that was okay as Karyn was still incredibly horny, having been left hanging by her first partner.

Mark fumbled with her buttons, prompting her to reluctantly let go of his twitching erection long enough to open her blouse and uncover her tits. His hands virtually flew to her boobs: cupping and squeezing and twisting and rubbing. It was more like mauling her boobs than playing with them. Quickly, though, his fingers zeroed in on her nipples: twiddling and pinching. Which just about drove Karyn crazy.