The darkness was all she knew. Molly was a quiet girl, damaged at a young age by her unhinged and irresponsible parents. Her father was absent and her mother was an addict, and she spent most of her time in those formative years alone, nurtured neither by family nor friends. She had none — even though she was exceptionally bright and pretty and charismatic when she felt like it, Molly was withdrawn and sullen and defeated. The world was her prison, a palace of pain and self-hate and enervating loneliness. Every other day there would be a new man in the house, staying anywhere from an hour to a couple weeks before her mother was onto the next one. Molly’s mother provided her shelter and comfort when she could, but she was too far gone most of the time to even communicate beyond basic questions like have you eaten, how was school. Well, school sucked most of the time, until Molly turned 18 and began her senior year of high school. Puberty was kind to Molly — she was endowed with enormous and firm breasts, a Hollywood actress’ iconic face, dimples and freckles and cheeks that begged to be pinched and squeezed, and a truly remarkable ass, a monument of want and the topic of much conversation for the boys (and many girls) of the school ever since it emerged out of thin air. Molly was aware and deeply uncomfortable with her body and all the attention it entailed. She didn’t date or go to any of the school dances for her first three years because the thought never even crossed her mind. She was useless, a sack of garbage incapable of bonding or communication, chained to her wretched life at home watching over her poor mother as she tumbled from boyfriend to boyfriend.
Molly knew how many people had crushes on her, but what did that even mean? How can you have a crush on someone you’ve never even spoken to? She didn’t trust them, because whatever feelings they had were based entirely upon her physical appearance, and she didn’t like that at all. She wasn’t going to be a slut like her mother. Blonde-haired and bushy tailed going into twelfth grade, she expected more of the same for her final year of high school. Pay attention, do the work, get straight A’s, go home, and pray for a full scholarship to come in October. She was desperate to go as far away as possible for college, and she had no expectations for her senior year other than getting that full ride. She was fascinated by history and English, and she tentatively decided to pursue a Philosophy degree. One of the perks of being a senior was being able to take all electives, and because Molly had dutifully completed her math and science requirements last year, she was taking two English classes, two history classes, and an introductory philosophy course. Taught by Mr. Benson, it was considered the hardest course offered at the school by a long shot, with a carefully curated class of no more than six people personally selected by the professor. Demand was always high, and Mr. Benson’s approval meant a lot amongst the students. Kids who got into his philosophy class were respected and well-regarded, even if their performance was less than stellar. But that was rare: Mr. Benson picked kids who really wanted it and could really do it. Molly was thrilled when she got her first semester schedule in the mail, and she smiled for the first time all summer. For once, she couldn’t wait for days to come.
The first day at school was predictably boring and draining: Molly barely socialized, ate lunch alone (when she did eat), and rarely spoke up in class. Still, the student body regarded her with an awe and want usually reserved for exotic animals. But there was no way around it: to every boy at Carrion, Molly was a regular fixture in their mental spank banks. At the same time, she was the unattainable treasure, the golden goose, of every single lesbian at the school. Even steady couples like Sarah and Aubrey talked about how obsessed they were and what they would do with her if they ever had the chance. That’s the thing: because Molly never talked to anyone, she became a symbol in the minds of her peers, an abstract projection that differed greatly from person to person: the jocks openly gushed in the locker room about her ass and her no doubt intensely kinky sexuality; freshmen who didn’t know any better looked up to her and saw her walking around campus and imagined her as the Queen Bee of the seniors; smatterings of Nice Guys and artsy types fantasized about dating her, even marrying her. The considerable lesbian and female bisexual population at Carrion thought harder and longer about Molly than anyone else, because they were convinced that her anti-social and standoffish personality was the product of repressed sexuality, and that her troubled upbringing cloaked her in shame and self-loathing. Of course they said all it would take is the right girl and the right time.
The truth was Molly knew herself pretty well. Better than most, in fact. She knew from an early age that she was bisexual, with a 60/40 split favoring boys, and she knew that her desires were unconventional, as they say. Part of Molly’s lack of engagement was a fear that she would be rejected by potential suitors and dates for being fucked up and disgusting. She enjoyed tying herself up long before she had any concept of what that meant and why it felt good. She was reluctant to admit it, even to herself, but she also learned a lot from her promiscuous mother. They lived in a tiny single story house, and neither of them had any privacy. But Molly’s mother just didn’t care — living in that house was a crash course in human sexuality. Molly heard and often saw everything, and she learned early on what turned her on and what didn’t. She was fascinated by anal sex, everything about it was just intoxicating to her: the stigma, the nastiness, the pain, the degradation and submission of the act. Anal sex was devotional, and Molly had a vast chasm of emptiness inside of her that begged to be fulfilled and sated by submissive, deeply kinky sex. She never went to any of the dances because she knew she was too much of a freak and she didn’t trust herself to lose it on the dance floor. Everyone would already be paying attention to her, what would she do if she actually got into it and took someone’s cock out and sucked it? It may sound absurd, and certainly irrational, but these were very real fears that kept Molly isolated from everyone around her. Until that fall…
Leaves were falling and the air was cold and crisp as Molly walked through the quad on that first day of class, her conservative uniform doing absolutely nothing to deter the stares of everyone she passed: her body and face were objectively stellar, a “10” as they would say in the locker room, and her cautious and cool persona only intensified a desire to get to know her, to understand her, to have her — from just about everyone she encountered. Peter and Bobby, two of her classmates, moaned loudly as she passed them, at this point not giving a damn if she heard them or not. High school was almost over — you had to say your piece at some point. “What I would do to her, oh my god, you have no idea, no idea…” Bobby shook his head, revisiting a scenario he’d dreamt up where Molly was on his bed with her hands tied behind her back, her mouth gagged, and her eager ass in the air, his own personal plaything. “I think I can imagine,” Peter replied, remembering all the times Bobby had recounted this exact fantasy to him for over a year. “You’ve told me this a million times. I get it. Honestly, it’s a bit run of the mill, if you ask me.” Peter had carried Molly in his mental spank bank for years now, and he would never admit most of the things she’s done in his head: namely, that she was a secret lover of bathroom play. Peter had launched many a load to the thought of Molly receiving his waste with enthusiasm, either on her chest, her breasts, or her mouth. Of course she always lapped it up and smiled in their dreams. “She’s gotta be a dyke. No other way to explain it. Makes no sense at all that she hasn’t had a boyfriend or even hooked up with somebody yet.” Bobby bounced out of his reverie, still massaging the mounds of Molly’s ass in his mind. “I don’t think she’s even been kissed, Pete.” Peter shook his head. “Damn shame. Damn shame.”
Molly knew enough by now to look straight ahead while walking across campus and never slow down, because somebody always wanted something from her. The fact that she gave so little made her even more appealing and attractive to everyone, and by now, even the straight girls were trying to get her attention in the halls. “Hi Molly!! Welcome back!” called Katie from across Senior Hall, but Molly had already turned a corner and descended the stairs, getting closer and closer to her philosophy class. Katie turned to her friends and frowned. “Why does she hate me?” Emma and Remy shrugged their shoulders. “She doesn’t hate you. She hates everyone,” replied Remy. “I’m pretty sure she could have friends if she wanted to, but she doesn’t. No one knows why.” Katie whined and wouldn’t stop complaining. “But I try so hard to be nice! Why won’t she listen?” Emma and Remy knew, but even Katie was in denial about her bisexuality. They had been enduring Katie’s disguised pining for Molly for years now, and after several drunken nights at parties with sloppy makeouts with other girls, they suspected she might even be gay, but too ashamed or too afraid to come out. They loved her, so they took her confusion in stride.
Just as Molly was walking into her philosophy class, Veronica walked by. They made eye contact and nothing more, but Veronica was convinced from that moment on that Molly was hers to take. Veronica was openly gay and had been for a while: president of the Gay-Straight Alliance, active organizer, and one of the horniest people at Carrion. Veronica went through girls like kleenex, but still, like everyone else, it was Molly’s unattainable beauty and mystery that drove her totally mad. She was so sure that if she could get Molly into her bedroom on a Friday night, she would have her spread eagle and gagged, begging for her first oral sex. She thought often about a threesome with Molly and Catherine, her longtime fuck buddy and sexual soulmate. Veronica and Catherine had spent hours lying in bed after vigorous sex pining and wishing for Molly’s presence, exchanging fantasies and desires for the girl all night. Her aura was intoxicating, indeed.
Molly entered CN-103 and quickly scanned the room: she was early, and no one had showed up yet. Except Mr. Benson. He was sitting at his desk writing, and when Molly walked into the room their eyes met and neither of them said anything for a while. It would’ve been uncomfortable if anyone else had been there. Truth was, Mr. Benson thought often about Molly, too. Carrion was an extremely progressive school, and relationships between teachers and students over 18 weren’t only discouraged but subtly encouraged, as the administration thought it might foster better understanding between age groups and, over time, would erode the stigma of the old and the young engaging with each other intimately. Thing was, Molly knew this, too. And Bertrand Russell wasn’t the only reason she wanted to get into this class so badly. She showed up twenty minutes early because she wanted this moment, needed it, just to see if she had any shot at all with the biggest crush of her life. Molly and Mr. Benson stood fixed in place staring at each other for over a minute — an unblinking, steadfast exchange of mutual interest that both picked up on and were intoxicated by. Molly’s strawberry vanilla cheeks turned bright red as that minute went on, and Mr. Benson’s trousers struggled to contain his rapidly growing erection. All the nasty thoughts had already run through his head, but now, all he could see was him and Molly kissing passionately on a bed of roses, her breasts and butt liberated along with her sexuality. Molly imagined almost the exact same thing, nearly identical — except in her head, she was stroking his rock hard cock. If only they knew.
A shuffle in the hall broke their trance, and Mr. Benson gestured to the desks before him. “Please, have a seat!” Molly blushed even more now, and look down at the floor as she found a seat off to the side and tried not to think about what just happened. How mortifying. He probably thinks I’m a freak. I already fucked this up.
“Pretty interesting carpet, right?” Molly snapped her head back up, her eyes wide as she sat directly in front of Mr. Benson, still beet-red and paralyzed with embarrassment. There were eighteen minutes left until class. “You can relax now. This class isn’t as hard as everyone says it is.” Molly just nodded in silence slowly, terrified of doing or saying the wrong thing in front of her crush. Mr. Benson smiled wider, and looked side to side. They were alone now. “I’m just putting this out there, feel free, you know, to ignore me or be grossed out, but if you ever feel like hanging out, I’d love to go out with you sometime.” Molly’s eyes were wide as can be, and she started shaking, overwhelmed by the frank proposition that had just landed in her lap. Was that it? Had she already won without even trying? Hearing the clock tick closer to class, she nodded enthusiastically and looked her teacher straight in the eye and let her lips reply oh so quietly, “i would love that. sounds great.” Mr. Benson was beaming. “Great! How about tonight?” Molly nodded vigorously, her whole body a mess of nerves and loose muscles she no longer had control over. Mr. Benson leaned in. “Meet me here after school?” Molly nodded, but this time said “yes” too, and it was the sweetest and most vulnerable and honest “yes” she had ever uttered her whole life, a three letter culmination of everything she had wished for and convinced herself would never come true. “Wonderful. I guess that’s only in a couple hours.” Molly looked at the clock — five minutes until class. Other kids would start coming in soon. She was breathing heavily and Mr. Benson tried to assuage her. “We can go get something to eat or just go to my place if you’d rather skip dinner. I know you might be nervous about this.” Molly was sweating bullets and her panties were all the way soaked through, her honey dripping down onto the plastic seat in a fine, viscous pool. “I’d love to go to your place and…hang out.” Mr. Benson said he was thrilled and couldn’t be happier that she’d said yes. Kids came in. The spell was broken. For now…
Those two hours went by like a lifetime, and both Molly and Mr. Benson were totally preoccupied with their evening plans. After Molly got out of her last class, she went to her locker and milled about for a while, waiting for students by Mr. Benson’s classroom to disperse so they could meet without notice. She glided through the quad as if on air, her heart lifting her feet off the ground. Her vagina would’ve left a trail if not for her densely knit plaid skirt. Carrion’s formal uniforms were inspired by Catholic schools and all the sexual connotations they contain. Despite the school’s rigorously progressive policies, their required uniform was seen as out of date and obsolete, when in fact it was the most radical rule in their books. Forcing students to cover up made them use their imaginations, and the same went for teachers. Molly entered the English building and made her way through the maze of departing kids and their overstuffed backpacks, drawing less attention than usual, at least in her mind. For all she knew everyone around her was imagining her begging for a vigorous face fucking — these intrusive thoughts plagued her every day, but not now. Not at this moment. She got closer and closer to CN-303 and the kids indeed started thinning out. By the time she reached Mr. Benson’s door, no one was in sight. She was safe. She turned the handle and went inside.
He was sitting there with his feet on the desk and his hands behind his head, looking at her with the same love and lust they shared mere hours ago. She didn’t know where to go so she just went to the same seat she sat in before. “Are you excited?” Mr. Benson asked as he got up and moved toward the door. Molly’s eyes followed him, but still she struggled to come up with a reply. “…yeah…” As she was saying this, Mr. Benson locked the door and pulled the blind down, and with a remote, sent the blinds of the exterior windows trickling down, until they were truly alone. Mr. Benson sat back down at his desk and folded his hands. “First of all I want to make sure you know that you are safe right now. Nothing is going to happen to you. Nothing bad, I mean. I know it might be hard, but I need you to tell me if at any point you feel uncomfortable and want to leave and go home. I’m not trying to seduce you. This is acting on mutual affection and attraction, as far as I can tell. I want to make sure you feel the same way.” He stared, and Molly blinked and started stammering, trying to get another “yes” out. But Mr. Benson frowned and cut her off: “Molly, if you’re not ready for this, I—”
“I’m ready. I’m ready. Please believe me, I’m ready. And I want this. So bad. I really do. I’m just…this is my first time. Doing anything. With anyone.” Mr. Benson was taken aback by Molly’s emphatic reply. He knew this was her first time, and while that excited him to no end, he was ethical and really a good guy, someone you could trust, and wanted to make sure beyond a shadow of a doubt that Molly was comfortable and wanted this. He got up from behind his desk and walked over to her, trying and failing to obscure the outline of his growing cock. Molly’s eyes caught his groin and suddenly he was behind her, his hands were on her shoulders, and he was massaging her. Touch. She’d never even been touched before in an intimate way. She shuddered in place and started breathing heavily. “Let’s go to my place and just hang out, get to know each other. You can talk about anything with me, Molly. I’m just here to make you happy. That means we can go as fast or slow as you want.” As he said this, Mr. Benson moved his left hand downward toward her breast, his massage extending now. “You wanna get going?” Molly caught her breath and moaned “yes,” and off they went to the parking lot and in Mr. Benson’s Mercedes. No one saw them on the way, but at that moment, Molly wouldn’t have minded. She finally felt safe.
During that forty five minute car ride, Molly opened up to someone for the first time in her life. She told Mr. Benson everything — her missing dad, her promiscuous mom, her social anxiety, and her kinks and fantasies. Mr. Benson was with her every step of the way, waiting for her to finish and adding what he could when he could. “I’ve always been really interested in…in…in anal sex.” Mr. Benson turned to her. “Oh yeah?” Molly nodded, “yeah. Just everything about it is so appealing to me…the whole idea of submission and allowing yourself to be dominated and taken in a way where pleasure isn’t necessarily reciprocal — it can be really painful even if you prepare and go slowly — but that’s what I love…like I’m really turned on by the idea of giving myself away. And like, butt sex is the ultimate, like, impure thing…it’s just so…animal…” Mr. Benson put his hand on Molly’s bare knee and continued, “I’ve always been a big fan of anal play, Molly. For many of the same reasons that you just stated. I also think something significant happens with that exchange of power between Dom and sub. Hierarchy is present throughout all of human history, and until relatively recently, slavery was widely practiced around the world. In these kinds of role-play scenarios, we’re lighting up a part of our brains that isn’t engaged in our society: the abject domination and imposing of superiority on another human being. I think there’s a lot to be gained from role-play experiences like that. Master and slave. Have you ever thought about that?” Molly was over the moon, now comfortable and communicating normally with her suitor. “Oh my god, are you kidding me? So much. I’ve wanted to try something like that for so long. I’m glad you brought it up because I was afraid to ask.” “Don’t be. You can really ask me anything, bring anything up. There’s nothing that’s going to stop me from wanting you, Molly.” With that genuinely sweet comment, Molly let out an “aww,” blushed hard, and involuntarily moved her hand onto Mr. Benson’s thigh. They both smiled. Her hand remained on his thigh as she replied. “…I was wondering what you wanted me to call you. During our…if we’re doing a role-play thing. I want to, by the way. I’m just wondering…I…sort of know what I want to call you…” Mr. Benson looked over, “What’s that?” Molly bit her lip and replied softly, “Daddy…” and with that, her hand slid from thigh to groin as she gripped the outline of the first penis of her life. Mr. Benson started breathing heavily and replied, “Yeah. Of course. We can do that. You can call me Daddy. I can be your Daddy. I’m really glad you said that, actually. That really turns me on. Because you know what I’m getting out of this—“ Molly’s mouth was hanging open as her hand explored her item of worship and devotion. It was getting bigger and harder every second. “—what I like about that dynamic is that I’m teaching you. I’m your guardian and your protector and your educator. I want to make your first time as fantastic and comprehensive as possible, and the thought of you—“ he looked over, and Molly’s eyes were fixed on his, while her hand continued stroking the outline of his erection — “the thought of you calling me Daddy while I teach you how to be a good girl is just so amazing. So amazing.” Molly was mewling like a sex kitten, involuntarily imitating all the pornstars she watched and idolized through the years. She was actually starring in her own movie now. They got off the highway and quickly entered Mr. Benson’s neighborhood, wooded and full of huge houses. “I want to be your slave,” Molly mewled, fully transformed into the ravenous whore she always imagined she would become, “I want to submit and give away my free will to you. I want you to dominate and teach me everything I need to know. I just want to make you happy, Daddy.” With that final word, Mr. Benson’s cock was fully erect, but still cramped in his pants. He turned to her and put on a stern look. “Do you want me to collar you, Molly?” Molly nodded slowly, like in the movies, and tried to move her head down toward his crotch. But he stopped her, pushing her head and her hand away as they pulled into his driveway. She reveled in the pleasure of being manipulated like that.
They got out of the car and went into the house through the front door. Molly knew Mr. Benson lived alone, but she had no idea his house was this big. “Welcome,” he said, as he gestured for her to come on in and make herself at home. “Want a tour before we get started? I think you’ll like it.” Mr. Benson walked Molly around his huge four story house and showed her the basics — kitchen, living room, dining room, bathrooms, guest bedrooms, and on the top floor, the master bedroom. “Stand right there in the doorway, Molly. I want to show you something.” Molly nodded and Mr. Benson walked over toward a closet opposite the bed and opened it. She could barely believe her eyes, but the closet was overflowing with bondage gear: ropes, restraints, ties, gags, whips, chains, paddles, plugs, masks…she couldn’t believe her eyes. “Does any of this excite you, Molly?” The girl nodded silently yes, as her man went into the closet and pulled out a steel dog cage. He looked at her matter of factly. “What about this?” She nodded vigorously and couldn’t stop saying yes, yes yes yes to everything, and so it was down to the basement where he took her by the arm and gripped her like she belonged to him. It was really happening.
The basement was furnished and filled with even more equipment for kinky play: stirrups, tables, bigger cages, beds, sex toys ornamenting every shelf and countertop. Molly was practically hyperventilating when she felt her ass being grabbed with a firm grip, and on pure instinct, she turned to Mr. Benson, put her arms up against his chest, looked up at him and mewled, “Oh Daddy, oh Daddy, oh Daddy, please take me, please take me, I want it so—“ He put a finger to her lips, and guided her back upstairs to the master bedroom. He sat her on the edge of the bed while he went back into the closet. He came out with a black collar, and he approached Molly now like a dog, something you own, something you control. His demeanor and dialogue turned icy as he held the collar aloft and commanded her to “Get on your knees.” The girl did as Daddy said, never breaking eye contact as she sunk to her knees and assumed the position of a submissive for the first time in her life. Her hands instinctually formed a prayer gesture, as if in worship of her new owner. He looked down at her. “This collar is important. It signifies that you are my property, and your will is gone. When you are wearing this, you have no free will. No volition. No purchase of your own. You become completely subordinate to my desires and my commands, and disobedience will result in extremely harsh punishment. You don’t want to know what I will do to you if you disobey, so don’t. But this is your choice. Only you can put this collar on…but only I can take it off.”
Molly’s life flashed before her eyes, as she stood on the precipice of giving herself away for three days on blind faith. She knew she was pretty kinky, but what if he was kinkier? She didn’t know. But she didn’t care. She deserved any punishment that she got because deep down she knew she was an abomination, a disgrace and a mistake, someone who never deserved to live, let alone end up here, in this heaven. She started crying, and Mr. Benson asked if anything was wrong. She shook her head. “no…no, not at all…i’m just so happy, Daddy.” She was sobbing now, unable to compose herself. “i’m so, so, so happy, Daddy. i’m just so happy. i’m so happy i’m…” Mr. Benson smiled and pet her sandy blonde hair. She looked up at him and wrapped herself around his leg. They were both still clothed. “I want to give myself to you, Daddy.” Mr. Benson looked at her sternly. “So you want to put this collar on? You understand what it means?” She nodded emphatically, “yes, yes, yes, a million times yes, i want to be your pet, your slave, your little girl, your personal plaything, your toy, your student, i want to be whatever you want me to be, Daddy.” He smiled. “Good. I’m glad. Stand up.”
Molly did as instructed, and she gasped as his hands moved up under her shirt and sweater and pushed them over her shoulders and past her head. She stood before him in only a bra and skirt, and he quickly slid that down her legs, leaving her in her soaking wet panties and bra. She stood at attention, awaiting direction or action. Mr. Benson took a step back, looked her over, and moved closer again. “I’m going to take off your bra now, Molly.” She gasped, and replied quietly “yes, Daddy,” as her man unlocked her bra and her breasts fell out in free air, as gloriously shaped and built as Mr. Benson imagined. “You are so beautiful, Molly. Do you know that?” Molly stood in place for a second, and then replied softly, “no, Daddy.” “No? Really? I know this is your first time, but—“ She looked up at him boldly. “no, Daddy…I don’t know that. I don’t think I’m beautiful…I’m gross…I’m disgusting…I’m such a freak for even being here or wanting this so bad, but I do…I don’t think I’m beautiful…I think I’m scum…” She started crying. His face sank, and he motioned to wipe her tears away. “it’s not your fault, Daddy! but I don’t think I’m beautiful, and I don’t love myself at all. I’m a horrible person. but I want to learn to love myself…will you help me?” Mr. Benson nodded and smiled. “Of course, Molly. Can I call you baby? Babygirl? …Daddy’s little girl?” Molly’s eyes widened. “ohmygod I want to be that Daddy, please. please let me earn it. let me show you what a good girl I can be.” She moved her hand up his thigh, but he swatted it away, holding the collar up to her face instead. “Then take to your knees, baby. Make your decision now.” Molly was still crying as she lowered herself in ceremony to her knees and looked her Daddy in the eye. “Please, Daddy. Let me put the collar on. I want to be collared and owned by you, Daddy.” She took it gracefully from his hand and held it up against her face. “I want you to use me like a pet. I want you to abuse me and punish me even when I do as I’m told.” She wrapped the collar around her neck, and started tightening it. Before the last notch, she looked up at Mr. Benson and mewled, “teach me, Daddy.” She fastened the collar, and let her hands rest on her thighs. Mr. Benson smiled, walked back to the closet, and returned with a leash. “Good girl. You’re such a good girl.” He clicked the leash in place and let it hang slack for a moment as they both savored the gaze of one another, that same hypnotic feeling of love and lust that they first felt just hours ago at Carrion.
Source: reddit.com/r/eroticliterature/comments/4y67w1/mollys_mysteries_losing_her_virginity_at_18_to