A Bookworm's First Time

All characters are 18+, and if things like lesbian sex, first-time, sexual name-calling, light choking, dom/sub, rough sex, age gaps, sadism and strapons aren't your cups of tea then this isn't the story for you.

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Clara had been watching the girl for over an hour, the teen's nose buried so far in a book that the rest of the world meant nothing. Observing the girl, still in her school uniform, reading Loving Her was titillating: if a female was questioning their sexual preferences there was hardly a better starting point, even if the reader herself didn't realize yet what she was doing. There were scenes in it that could make someone blush, and that was exactly what was happening to the girl who was so engrossed in its pages.

It wasn't until Clara slid into the booth with her that she finally picked her head up, her blonde pigtails and blue eyes positively cherubic. An awkward pause stretched between them, Clara waiting patiently to see if the girl would be as polite as suspected, and after a few moments her gamble was rewarded.

"Ummm, hello, ma'am. Can I, uh, can I help you?"

Clara leaned forward, her low-cut blouse giving the teen a front-row view of her ample cleavage. She held out a hand, the girl shaking it on instinct, and she finally introduced herself.

"Hello, miss. My name is Clara, and I was intrigued that you're reading a very interesting book. Not many women do, especially in public, so it's always lovely to find someone so adventurous."

Her last word was purred, a heat to Clara's tone that the girl didn't understand, but she liked it. In return the teen offered her name, introducing herself as Zoey, and over the next thirty minutes they chatted amicably. Throughout their conversation Clara made sure to be very handsy with the girl, her legs or fingers almost always in some sort of contact, and slowly but surely her plan was working. The older woman was masterful at picking out shy, young women to seduce, and with how cutely Zoey was blushing it wouldn't take much more effort to get the girl right where she wanted her.

The tension between them was growing, though Zoey was so inexperienced that she didn't know how to do more than blush and look away when the older woman said something risqué, and she was intrigued by the sophisticated photographer who was treating her like an adult instead of an eighteen-and-a-half-year-old. When Clara offered for them to go back to her apartment so she could show Zoey some of her photos the teen knew that she should have refused, that it wasn't the proper thing to do, but a piece of her knew deep down that Clara was going to try and seduce her -- and she wanted the gorgeous brunette to do just that.

"Oh, ummmm, sure! I can come over for a little bit, though I have to be home by eight to finish a report I have due tomorrow."

With a flirty wink Clara slid from the booth, offering her hand to the teen.

"No worries, I'll make sure you leave in time."

They had hardly gotten in from the hallway, the door clicking shut behind them, when Clara got right in Zoey's face. It was a make-or-break moment after their flirtatious session in the cafe, and Zoey would either run or allow Clara to take control. For the dominant woman there was no middle ground -- she regularly slept with a harem of submissives, all of them beautiful, young women who had been trained to suit her preferences in bed, and she was determined to add Zoey to her collection.

Before Zoey could back away Clara was kissing her, the older woman's lips pressing hotly to the shy teen's, and she felt the girl stiffen. For a heartbeat she thought Zoey might flee, every muscle poised to run, but then she let out a sweet little whimper. That was the moment Clara knew she had Zoey: the girl was hers, and she was going to push her seduction skills as far as they would go. She ran her tongue demandingly over the teen's lips, and just as she'd hoped Zoey parted them as she surrendered her mouth to the experienced lesbian.

Clara's arm encircled the girl's waist, pulling Zoey closer, and the teen was now flush against her. For several minutes they made out, and Clara delighted in how sweet and soft Zoey was. The teen's obvious lack of experience wasn't a hindrance at all, Clara happily guiding her through the basics of making out, and by the time they broke apart Zoey's plain, cotton panties were wet from the intense kissing.

"Clara, wow...!"

Zoey was awestruck, her first sexual encounter already beyond what she had fantasized it would feel like to make out with someone. She never imagined it would be a sexy, older woman that she would give her first kiss to, but somehow it felt right. Clara's arm was still wrapped around the girl, and with her free hand the older woman suggestively pushed the first button on Zoey's shirt through its slit.

"Oh, ummm, I don't think my shirt should come of..."

Zoey's protest was silenced with another kiss, the teen gasping as the next button was insistently undone. She could feel Clara's tits pressed up against hers, their chest sizes vastly different, and she briefly wondered if the older woman would even like her small, perky breasts. When their kiss broke apart Clara leveled a stern look at her, the dominant woman wanting to make her expectations clear.

"I can give you mind-blowing sex, sweetheart, but I only fuck good girls who are submissive to me. That means you don't question me -- my word is law, and you only use a special word to say no if you truly can't handle something."

Zoey's eyes had gone huge, her cheeks scarlet from hearing such direct, erotic talk. No one had ever spoken that way to her -- or even in front of her -- before, and she couldn't deny the way it caused her pussy tingle with excitement.

"If you agree to my terms then I'll fuck your wet little cunt until it's throughly satisfied, but only if you're sure this is what you want. It will be intense, and maybe a bit painful if you aren't used to it, but I promise you'll cum harder than you ever have before."

She stopped her words there, allowing Zoey several moments to soak up the information and make her decision. After a minute the girl raised her eyes, curiosity brimming in them.

"If I, if I give myself to you, like that, we can, ummmm, do that now?"

Clara merely nodded, the older woman biting back a triumphant smirk. She had Zoey in her thrall, and it was only a matter of seconds until the teen gave in. She was right, of course: a heartbeat later Zoey began unbuttoning her shirt, her choice clear, and it wasn't long before the teen was standing in Clara's entryway in nothing but her panties. She wasn't wearing a bra, a fact that made Clara's cunt gush, and next time she came over the girl wouldn't be wearing panties either.

Without a word Clara took Zoey's hand, leading her into the living room. She sat her down on a plain, hardwood chair, Zoey instinctively pressing her thighs together in subconscious modesty, and a moment later the older woman returned with a few items that she sat on the table behind Zoey -- including a blindfold and a collar. She slipped the silk band over the teen's eyes, not asking permission, then the collar fell into place with a soft, metallic click.

"Whenever you're here you'll put this collar on, since it's the symbol of your decision to submit to me, and if you truly need to say no to something then the safe word is 'pancake'. Any variant of 'stop', 'no', 'ouch' or 'please don't' will be ignored -- is that clear?"

Zoey immediately nodded, her face tilting up towards Clara.

"Yes, ma'am."

Damn, the girl was going to be perfect. Another soft, insistent kiss was pressed to Zoey's lips, the teen eager to let her new lover explore her. When they broke apart Clara's eyes were filled with hunger, and she ran her thumb tenderly over Zoey's bottom lip.

"You belong to me now. You're mine to do with and speak to as I see fit, and I can't wait to turn you into my perfect little fuckdoll."

The heated, dirty words did something to the girl, turning her on at a level that she didn't know was possible, and she blushed scarlet at the brazen speech. Clara stripped herself, then quickly attached the harness she had brought into the living room with her. It held a modest dildo, nothing too big or too wide since she suspected she was about to claim Zoey's virginity, and she couldn't wait to fuck the sexy, nubile teen with it. She wanted to hear Zoey scream, to moan like a whore, and these were the thoughts driving her on as she began to play with her newest toy.

At first her touches were light, the caresses starting at the girl's shoulders, but soon enough they turned more demanding as they inched their way closer and closer to the teen's breasts. Clara loved Zoey's little tits, the succulent, peachy globes a perfect handful that would still grow with time, and the moment her fingertips made contact with twin nipples the teen jerked back in surprise. Fortunately Clara's hands were warm, the erotic touch equal parts electric and enjoyable, and after her initial reaction she held still to let Clara continue her ministrations.

Despite how fast things were moving, the evening unfurling in a way that Zoey had never expected in her wildest fantasies, she felt an innate sense of belonging with Clara that she hadn't experienced anywhere else before. The older woman's hands were everywhere on Zoey, fingers exploring as they mapped the curves of the girl's body, and after a few more minutes she helped pull the blindfolded teen up onto her feet. Then Clara crouched down, and with a well-practiced tug she got rid of Zoey's panties, flinging them off to the side as soon as the girl had stepped out of them.

The teen's pretty, pink pussy was finally bared for Clara's viewing pleasure -- Zoey was undeniably aroused, cunt juice leaking down her thighs, and it was clear that she was ready to be fucked. Zoey's breath hitched when her panties were tossed aside, the dominating move increasing her arousal. As the older woman drank in the sight of the girl's innocence she leaned forward, Clara reverently planting a possessive kiss on Zoey's slit.

She ran her tongue along it, lapping at the teen's juices as she practically purred like a cat with a bowl of cream. That earned a breathy, needy whine from the girl, Zoey biting her lip to keep herself from moaning, and it was clearly a battle she was close to losing. Clara's eyes darkened possessively as she pulled her face back, her tongue darting out to lick lips that were now glazed with Zoey's sweetness.

"Open yourself up for me."

With trembling hands the command was obeyed after only a moment's hesitation, the teen never having felt so vulnerable and exposed before as she spread her cunt for a stranger. The cool air against the inner warmth of her cunt made her shiver, her skin feeling extra sensitive from her high state of arousal, and she desperately longed for Clara to use her mouth again. Zoey was indeed a virgin, no lover ever having known her so intimately before, and beneath a patch of blonde curls were the glistening folds of her untouched pussy.

For a moment Clara just stared, incredibly pleased with how things were progressing, and she deeply appreciated the delectable sight. The older woman's hands quickly followed the path of her gaze, her fingers lightly stroking upwards along the teen's thighs. The teasing continued for several minutes, Zoey growing more and more excited by the second, and soon the blindfolded girl was practically sobbing with her need for release. Then Clara unexpectedly grabbed Zoey's thighs, spreading them further apart as she growled up at her new toy.

"Say it, my sweet little slut: tell me how badly you need me to fuck your precious cunt."

There was no hesitation, Zoey ready to say and do anything if it meant finally getting Clara's hands or mouth where she longed for them the most.

"P-plea-ase, fuck me! I need it-t so bad..."

A sharp smack to her inner thigh -- that sensitive spot just below a girl's pussy -- made the teen jump, Zoey letting out a squeak as her body jolted.

"That's "please, Mistress", darling. Never forget to call me that."

Zoey nodded frantically, the girl quickly grasping that what Clara wanted was what she got, and she was there to give Clara whatever she wanted.

"Yes, Mistress!"

Clara hummed her approval, the older woman climbing to her feet. Her next move was to take over the chair Zoey had been in, Clara sitting down and pulling the teen towards her. She positioned the girl facing away from her, and she helped guide Zoey backwards a few steps until the teen was able to sit on the older woman's lap. There was something so dark and thrilling about allowing Clara to manipulate her body that way, an edge of danger to their encounter that Zoey couldn't ignore, and the innocent beauty was so glad that the sexy, experienced lesbian had chosen her.

Every move the submissive made was hesitant, her body language conveying just how unsure she was, yet like a good girl she didn't shy away when she felt the silicon nudging her lower back. At the same time Clara leaned forward, her lips finding their way to Zoey's neck as they grazed the tender skin. The older woman's tits were pressed against the teen's back, her nipples hardened with excitement, and she whispered hotly in the girl's ear.

"I'm going to show you what it means to truly submit, so lift your hips for your mistress like a good bitch."

Her silken, breathy whisper was accompanied by one hand wrapping around the faux shaft, Zoey following the order despite the wave of uncertainty clenching in her gut. Before she could overthink it the head of the strapon was pressing into her, the strapon penetrating her virgin pussy, and Zoey cried out as she was deflowered. Clara had purposefully done nothing to prepare the teen's inexperienced hole -- she wanted the girl to feel every painful inch as her walls stretched and burned with friction from accommodating the dildo, and knowing it would hurt Zoey a bit was part of what turned Clara on so much.

She loved inflicting pain on her partners, their screams and whimpers music to her ears. Her submissives were trained in the art of sexual masochism, the girls taught to love receiving pain from their mistress, and Zoey would be no exception by the time Clara was done with her.

"It hurts! Please, stop...!"

The words were half sobbed, the last one punctuated by an attempt to wiggle off the fake cock, but Clara was having none of that. Her hands went to Zoey's hips, her fingers digging in as she pressed the teen downwards onto the toy, and she groaned in delight as she felt the head of the strapon bump against Zoey's hymen.

"Shhhhh, sweetheart. You're being such a good girl for me -- just a little further, and my cock will be all the way in you where it belongs."

She reached a hand up, gently gripping Zoey's chin and turning the teen's head to the side. She leaned forward, bringing their lips together, and with a brutal thrust of her hips she slammed the dildo home. Zoey screamed into the older woman's waiting mouth, the contrast of the soft kiss and painful penetration making her body burn, and her cry was captured by Clara as the mature lesbian began thrusting rhythmically into the poor girl's burning cunt.

With one hand holding Zoey's chin Clara took her other and brought it to the teen's breast, her deft fingers locating a nipple and rolling the nub playfully between her thumb and forefinger. For several minutes they remained exactly like that, a blindfolded Zoey subject to Clara's ravenous sexual appetite, and with each thrust the pain faded just a little. By the time Clara's hand traveled downwards from Zoey's tits to the girl's clit there was a spark -- something almost resembling pleasure -- dancing in Zoey's cunt. Every movement still sent pinching bites of pain through her battered lower half, but it was morphing into a sensation that she almost dared to call enjoyment.

Clara's thumb began to stroke Zoey's red, swollen clit, the poor, neglected nub just begging for attention. As she did she released the girl's chin, her freed hand gravitating to Zoey's other nipple, and the dual stimulation quickly began pushing the teen into her first orgasm. Zoey was writhing and panting, her back arching to press more of her breast against Clara's skilled fingers, and she couldn't help but moan like a whore as she let a gorgeous dominatrix take her virginity.

"That's it, darling! You're so perfect, so beautiful, and I'm the luckiest woman alive to have met you."

The words were true, Clara meaning every one of them, and she could tell that her new plaything was getting close to cumming. There would be plenty of time later for orgasm denial training and edging, but for the moment she wanted Zoey to experience enough enjoyment that the teen would want to return. She replaced her fingers with her palm, then began grinding it against the girl's clit in hard, fast circles.

"Cum for me, you desperate little slut! I want to feel your wrecked cunt clench all around my cock as you scream my name, and remember that I own this pussy."

With a quick shift upwards Clara's other hand was gently squeezing Zoey's neck; the slight bit of danger -- coupled with the incredibly hot ownership claim and clit stimulation -- sent the girl immediately over the edge. She came, bursts of light popping off behind her eyes, and her vaginal walls constricted delightfully as a shattering orgasm broke her. Though the teen would hardly remember it later Zoey did indeed scream Clara's name, the sound the most lewd noise of half pleasure and half pain that she had ever made in her young life.

Clara had stopped moving, the dominatrix wanting to watch her submissive come undone, and she adored the way Zoey was bucking and shaking. Soft, but wild, cries of pleasure were tearing from the girl's throat as the aftershocks of her climax jolted through her newly-deflowered body, and she was subconsciously humping against Clara's hand to keep friction on her clit. The sight made the older woman's cunt ache with arousal, and she lamented that it wasn't her big, double-ended dildo that she was wearing so she could get off too. That was her favorite toy to fuck her submissives with, and she couldn't wait to use it on Zoey.

When the teen finally stopped moving, the girl going limp as she leaned back against Clara, the experienced lesbian reeled her hips down to pull the strapon out of Zoey without them moving.

"Unnnng!"

Zoey's whimper was musical, and Clara knew she had found the perfect new lover. She ran her hands up and down Zoey's chest, lightly caressing the teen's cute, puffy little nipples, and peppered adoring kisses along her neck and shoulder. There was no question, however: Clara needed more.

"Stand up, sweetheart. You did so well, and I want to give you a reward now."

On wobbly legs the girl obeyed, her pussy pinching in protest of the movement, and she let Clara lower her to the floor. Two more items were grabbed from the table, and Zoey listened curiously Clara moved about. Then the older woman was kneeling in front of her, and she began speaking as she reached for Zoey's arms.

"Thank you for being so amazing, darling. I know that hurt, but you took it so good! You were perfect, and you looked so powerful and sexy as you came... I couldn't take my eyes off of you."

The praise made Zoey's heart flutter, the teen enchanted by Clara's description of her.

"Thank you, Mistress. It hurt, really badly, but then it started to feel good after a little bit."

Clara leaned forward, placing a quick, sweet kiss on the submissive's lips.

"That's exactly how I always want you to feel -- orgasms are always better and more intense when they stem from a mixture of pleasure and pain, the kind that can only come from being fucked like you just were."

It made sense to Zoey, and though it had been rough at first she already found herself wanting Clara to bring her to that same peak again. With a soft click a pair of handcuffs were fastened to her wrists, her arms now held in place behind her back, and before she could speak again a ball gag was being slid between the teen's lips.

"There, that's my good girl -- you look so beautiful, and I still can't believe that you're mine."

She gently pushed Zoey down, the submissive now on her back on the floor, and Clara spread the girl's legs so that she could position herself between them. Her hands began slowly roaming up Zoey's legs, fingers kneading idly into the supple flesh.

"Do you know why I gagged your mouth?"

All Zoey could do was shake her head, a muffled sound of denial coming from her occupied lips.

"I did this because, when you're in here, you belong to me. Your thoughts, opinions, voice... all of it is mine, and I'll listen only when I deem fit. I'll fuck you, very roughly, and the sounds you make -- good or bad -- don't matter. If I hurt you, and you want to beg me to stop, there's nothing you can do. You can't move, see or speak, and that's the beauty of your ultimate surrender to me."

Clara began to kiss her way from Zoey's belly up to her neck, her hands roaming as they teased the bound girl. Beneath her Zoey was wiggling her hips, the teen not even aware of what her body was doing, and the subconscious begging was a huge turn-on. When Clara reached Zoey's neck she sat up, then hooked the teen's legs up over her shoulders. She yanked Zoey downwards, partially lifting the girl's ass, and with one rough shove the strapon was once more filling the submissive's plundered pussy.

Zoey let out a half-sob half-scream, Clara moaning as she forced the silicon into the girl's tight cunt. This angle of penetration was deeper, the position much more intimate as the strpaon hits spots inside of her she didn't even know existed, and the dominatrix delighted in getting to see Zoey's expressions as she was fucked. For several minutes she hammered away at the girl's poor, aching cunt, every second of lewd, wet sounds heightening both women's arousal, and then Clara changed her style.

"Let's see if you can take more."

She pressed her weight forward, her body almost fully on top of Zoey's now, and she rocked herself forward with long, languid strokes. Zoey groaned, her pussy a painful mess, but she loved the new angle. Having Clara covering her, the older woman's full weight pinning her down, felt so good, and she loved the sense of security it gave her as each move made the base of the strapon bump against her clit. She was practically bent in half, her legs pushed way up as she was plowed, and Zoey knew right then that she wanted to keep being Clara's submissive.

The teen had never felt so wanted before, had never been the center of anyone's attention in such a way, and she was certain she'd return. It didn't take long for the girl to cum again, her back arching and her eyes fluttering behind her blindfold as she tried to cry out in pleasure around the ball gag. She was the perfect picture of debauched submission -- bound and helpless, fully at Clara's mercy, yet cumming from her cunt being relentlessly plundered by the commanding, experienced lesbian.

"Fuck, baby, you're so hot! Look at you, getting off from taking my strapon up that slutty little hole of yours... you're such a fine piece of ass, and I'm going to turn you into my perfect sex toy."

That wasexactly what Zoey wanted. Two hours ago she was an innocent, virgin schoolgirl, the eighteen-and-a-half-year-old never once imagining that she was going to have sex for the first time that night when she went to the cafe, and now she couldn't get enough of hearing Clara call her degrading names while thrusting into her aching, deflowered pussy as it clenched around the older woman's strapon. Clara reached out, grabbing one of Zoey's nipples and giving the nub a rough pinch, her gaze thoughtful as she tugged it experimentally.

"Hummmm, we're going to have to get you some clamps -- your nipples are so puffy, which means they'll feel them more."

Zoey didn't know what nipple clamps were, though the name gave her a vague idea, and she couldn't help the way her back arched to offer her tits to her mistress. By that point Clara figured Zoey had cum enough for their first night together, her own pussy begging desperately for release, and with a wet squelch she pulled out of the teen's soaked cunt as she released the girl's nipple.

"Don't move."

The command was obeyed as the dominatrix stood, the strapon quickly falling to the floor as she unhooked it. A moment later she was kneeling over Zoey's chest, deft fingers removing the gag. The girl had done well, her legs shaking but held accordingly, and it was incredibly hot seeing her pussy remaining spread so obediently. Once the mouthpiece was off Clara scooted forward, lifting her hips and dropping her pussy until she felt Zoey's nose bump against it.

"Here you go, baby. You did so good that you've earned a reward, and you'll quickly learn that there's nothing better for you than eating your mistress out."

Zoey had no idea what she was doing, her inexperience glaringly obvious, but it didn't take her long to figure out that just about any contact with her tongue was enough to elicit sexy sounds of approval from Clara. The older woman was so aroused that even amateur lapping felt good, and when Zoey's tongue accidentally swiped over her clit she practically came.

"Yessssssss, right there! Do that again!"

The girl did as she was bid, flicking her tongue playfully over the bundle of nerves, and she figured she must have done something right when it made Clara moan, the dominatrix grabbing Zoey's hair and pulling the teen's face as close as it could get. She ground her hips down, riding the girl's face with wild abandon, and a moment later she screamed as she came. Though she knew she wasn't good yet Zoey felt a beam of pride, a smile curling her lips even as her mistress' cunt juice smeared across her cheeks.

She had made Clara cum, had brought the older woman pleasure, and that made her happy. When Clara's orgasm subsided, her cunt still pressed to Zoey's face, she slowly stood up while helping the exhausted girl to her feet. Clara took her hand, leading the teen to the kitchen where she fussed over her submissive like a mother hen. She cleaned up Zoey's face and pussy, making sure she was nice and clean, then she had them sit down on the couch together as she snuggled the girl in her arms.

"I want you to walk me through your experience. What did you like, what didn't you like, and what would you want to try in the future?"

They talked for almost an hour, Clara answering questions and explaining more of her dom/sub process. She listened to Zoey's feedback, making sure to take mental notes on how she could introduce the teen to new experiences. It was starting to get late, Zoey needing to get home before her parents started to worry about her, and Clara -- still naked -- walked her to the door. Zoey couldn't keep her eyes off of her mistress, and if she could have stayed longer she absolutely would have. When they reached the door Clara stopped them, wrapping Zoey in her arms and pulling the submissive in for a quick, hot kiss before letting her go.

"So, will I see you after school tomorrow?"

There was no hesitation as the girl nodded, though her smile quickly shifted into surprise at the dominatrix's next words.

"Good! I should have one of my other girls here, and the two of you can have a fun, sexy play date together."

It was said so casually, as though it were perfectly normal for Clara to imply that she had multiple submissives who fucked each other at her behest, and after a second of processing Zoey realized that it likely was the norm for the older woman. She was gorgeous, wealthy and had as much charisma as ten average women, so why not? For a moment a flash of jealousy zipped through Zoey, but she had always been a reasonable person -- she had just met Clara, wasn't in any kind of romantic relationship with her and their entire existence together was based solely on sex.

Could she really do more things with another stranger, though?

"Yes, Mistress."

Clearly Zoey had made up her mind, and though it would be a lot for her to continue processing while she was alone in her room that night she already knew she wanted to come back. She could still taste the sweetness of Clara's pussy on her tongue, and there was no coming back from such an intense, trust-filled first sexual experience. She would know on that door tomorrow as surely as the sun would rise, and she would do whatever Clara commanded.