Betty saw through my lies yesterday, completely picked apart my story like some sort of sexual Sherlock Holmes. If I had gone back today claiming my dry spell continued, she would have known. So I tried a feint.
I left Lilly untouched that morning, having only time to explore her home before the coffee shop opened. That turned to my advantage. I was already clocked in when Betty unlocked the door, beelined for me as I was stocking the apples and bananas by the register.
“James! You’re looking oddly cheerful.” Her hair was different today. Her dreadlocks were undone, and her hair was a ratty mess. She had bleached it, and she looked burnt out and trashy. Betty was at her best when she looked trashy. She hadn’t yet put on her apron. Or a shirt. Just showed up in a sports bra that seemed too small for her.
“Well, I’m feeling good.” I gave her a big grin. I had spent the last half hour coming up with a believable story.
“Oh?” She leaned in close, clicking her tongue against her teeth. “So, are you ready to tell me about the lucky lady?”
“Fine, but it’s not what you think.” I coyly shrugged. “I met a girl online.”
Her grin spread. “I knew it! Where did you take her for your date? Or, dare I ask, was it more of a fuck appointment? Her house? Yours? Some sleazy motel with the vibrating bed?!”
“I hooked up. But…” I held up a finger and dramatically held the pause while I enjoyed the smell of weed and booze wafting off Betty. “I didn’t, you know, actually get laid.”
She tilted her head and considered. “Really? Because you seem awfully cheerful for someone who’s been so unfucked that I think your virginity grew back.”
“Yeah, yeah. OK. So this is why I didn’t want to talk about it. It’s embarrassing. I met a girl on a website. She’s not even in this country. We’ve just been having some really, really hot cybersex. Kinky shit, too.” I puffed out my chest proudly.
Betty’s shoulders sank. “Oh.”
I had been to the website where Lilly was finding her stories. It was on the bottom of the pages she printed off for her homemade book collection. People were posting dozens of stories there a day. And they chatted obsessively about sex. So, of course, a lot of people use the site to hook up. Both physically and digitally. I decided to use what I had been reading about to throw her off.
She stared in silence and watched me, trying to bore into my skull to find the truth while tapping her tongue piercing against her teeth. Click, click, click.
“I know, that’s not… like… It’s not a three-way with Dirk after sleeping with his sister, exciting, but it’s big for me. We’ve been doing some roleplay. Dom/sub stuff.”
“Is that so? And I’m to believe you’re… dominant?” Click. Click. Click. “What kind of roleplay? Tell me exactly what you did last night?”
“Well, it’s cliché but…” My mind drifted to Lilly’s closet.
Honestly, I was overwhelmed by the sheer volume of kink in one place. It was like she had her own personal sex shop. Strange devices, ropes, handcuffs… stuff like that. And the clothes! So many kinky clothes.
They excited me the most. Like she had raided the sluttiest Halloween store in the world. I had briefly looked at them, all pretty much the same size. All unopened. Anything I could think of. Nurses, nuns, and of course…
“Schoolgirl. Schoolgirl teacher.” I’m a simple man. The plaid skirt and white button-up had caught my eye the second I opened the door.
Click. Click. Click. She suddenly leaned in, grabbing me by my collar. Yanking hard, she pulled me to her face. In the heat of the moment, I thought she was going to kiss me. I even puckered my lips. “What the fuck are you doing? Open your mouth.”
“Oh, um… sorry.” Not exactly sure what was going on, I did as she commanded. She leaned in and sniffed my breath. Then my chest. She reached down and grabbed my hands and started sniffing those, too. I swear I felt her tongue lick my index finger. “Betty, what are you doing?”
She squinted and peered at me. “Good story. Covers most everything. Except for one small detail. I know I smelled cunt on you yesterday.”
Fuck, Lilly’s sex was strong. And Betty was like a depraved bloodhound. If I had fucked Lilly before I came in, she would have smelled her all over me. “You imagined it.”
“Hmm. Did I? Because I know the smell of pussy. I adore it. And even though every girl is different, there’s a distinctive something about slit slobber that drives me up the wall. Just like it did yesterday when I smelled it all over you.” She suddenly dropped to her knees and pressed her face into my crotch. Not just sniffing the area. Rubbing her face against my thigh, her nose bouncing off the head of my cock, and inhaling deeply. The warmth of her breath made me hard instantly.
“B-b-betty…” She had teased me relentlessly for years. But she always made a point of never touching me intimately. This was a first. My eyes fixated on the aquatic design of the tattoos on her back. A large, colourful octopus surrounded by underwater plants. For years, I had longed to see her naked, see how the tapestry of dyed skin and drawings looked on her without clothes blocking my view.
“Yup, this is one sad unfucked penis. Sorry, James. Had to be sure.” She looked up at me. “I’ll let you go for now. But I’ve got my eye on you, ya filthy liar.” And with that, she let her tongue hang from her mouth. And with her green eyes staring upward, she pressed it into my jeans. Slowly running her tongue up, the black stud clinked along the teeth of my zipper as I felt my knees getting weak.
And once she reached the top, Betty opened her mouth and breathed hot air onto my hard cock. Finally, tapping her tongue stud against the button of my jeans, which happened to be right where the head of my cock had swelled.
Click. Click. Click.
Giggling, she hopped back to her feet. She reached down into her purse and pulled out a tiny shirt that barely covered more than her bra. “What are you standing around for? We have work to do.”
——————————————
The remainder of the shift was torture. Betty hardly said a thing to me for the rest of the day. Just glances and winks. And the constant clicking.
All day.
Click. Click. Click. Grabbing my attention. Turning me on, making me swell. I constantly had to adjust myself, much to her delight.
Sometimes she would just bring out her lipstick and apply a fresh, heavy layer of glistening black. Smacking her lips at me, her captive audience. She let me have no quarter for relief. As soon as the rush died down, I tried to jerk off in the bathroom. I barely unzipped my pants when she knocked on the door. “What are you doing in there, Sir? Please limit your bathroom activities to the expulsion of shit and piss only.”
And if Betty wasn’t bad enough, I also had the thought stuck in my head about the treasures of Lilly’s closet. And that schoolgirl outfit.
It had always been a fantasy of mine, even back when I went to a Catholic school. I had fantasized about the pretty girls in my class and taking them behind the bleachers or sneaking off to an empty classroom and fucking them in their uniforms. Of course, I was a virgin till college, so you can imagine how that went.
But even though my cock ached, at least I knew exactly what I wanted when I got home. And with the next day off, I’ll have plenty of time to play with Lilly.
“Hey, James,” Betty called to me as I gathered up the trash, ready to take it out and head home and escape this sexual bating game she was playing.
“Yeah?” I looked up, and she had her shirt and bra pulled up. Betty had such great tits. Perky, looked like a solid handful each. And those silver nipple bars had been tantalizing my mind for years, wondering what it would be like to roll her teats around in my mouth.
“Tomorrow, house party at my place. Dirk’s band is playing. Be there, maybe we’ll see about finding you a nice flesh and blood pussy to fuck.” I would have been grateful for the invite had I not been planning on fucking Lilly rotten.
“I can’t. I, um…” She bounced on her toes, silencing me with a tantalizing jiggle.
She crept forward. I realized I was backing up when I ran into the wall. Betty carefully pushed her chest forward, till I could feel her erect nipples drag against my shirt.
Click. Click. Click. Her finger tip reached down, and she pushed my pants against the tip of my cock. It was only then I realized I had been leaking cum so much there was a visible dark stain where she touched me.
“Yeah, you’ll be there,” she said factually.
Guess I’ll be there.
——————————————
‘Article 4: You are not to use any of my possessions unless it is in service of the conditions of Article 5.’
I wasn’t exactly sure how this was going to work. I prepared myself a lot like I did the first night. I dressed up. Not because I had any expectations of something more intimate or for Lilly’s sake. But because I was feeling playful. If I was going to dress her up, I wanted to match.
Being a barista living paycheck to paycheck, I didn’t have many nice clothes. But I looked at myself in the mirror and considered the oddly fitted brown suit I only used for job interviews. I struggled with the tie; despite the internet tutorials, it took me nearly an hour to get it right. My shaking hands didn’t help. I needed to get off.
I could have knocked one out as soon as I got home, relieved the pressure Betty had been building up all day. But at this point, I wanted to keep it all for Lilly.
I adjusted the tie and took one last look in the mirror. I looked like a sleazy, run-down teacher.
Perfect. Now to go meet my pupil.
——————————————
I walked into the house and removed my shoes. Lilly gave me her normal greeting, and by that I mean she looked up briefly from what she was reading before burying her face back into the book. I wandered over to read the cover. “Naughty Step-Mummy”. I made a mental note of it. Sounded good. I wanted to know what turned her on, read what she reads.
I found her fascinating, and craved more insight into Lilly Redwood. I had searched for her online and found no social media presence at all. I tried to figure out which of the users on the story website was her. I had no way of really narrowing it down. But this was research for another time. I was here to play. I walked past her and toward the walk-in closet in her bedroom. I flipped on the light and took a moment to appreciate the majesty of it. By a rough estimate, there were more than a hundred outfits. From a full-on Victorian dress with a corset to adult baby costumes complete with diaper.
And the toys! I didn’t even know what a lot of them did! They were all sorts of shapes and sizes with different buttons and latches. I quickly took out my phone, snapping pictures of some of the stranger ones to look up later.
I walked by the schoolgirl outfit and froze. I realized there wasn’t just one, there were three. A cheap sex shop costume, an actual Japanese sailor uniform, and a long pleated skirt and top that actually resembled something closer to what girls wore in my school. Decisions, decisions.
I closed my eyes while emptying my mind, and let my hand hover. Fate guided my fingers to a garment.
Slutty and cheap it is.
——————————————
‘Article 5: You may use my body in any way, at any time you like. I shall obey any command and follow any order to the best of my ability.’
Time to put that to the test.
I presented her the outfit from her closet. She looked up and studied it. Finally, I had done something that warranted her putting the book down on the side table.
“I want you to wear this for me.” Without a word Lilly set down her book. She stood up and began to strip. She peeled off her sweats and, folding them neatly, placed them next to her story.
And somewhere in the back of my mind, I could hear the ‘Click, Click, Click’ of Betty’s tongue stud. I kept staring at Lilly’s mouth. Betty’s lips were always covered in thick lipstick, wet and tacky. Lilly’s were dry, slightly cracked, and bare. And her large breasts swung as she bent over and pulled down her sweat-stained bulk-bin panties.
She reached for the outfit, which I happily relinquished. She bit into the side of the plastic with her teeth and tore it open. It even smelled cheap with the chemical scent of clothes that were more plastic than anything else. Sitting on the chair, she put on the knee-high socks first. Her legs spread wide while she slid them up her legs, and I caught a whiff along with a glimmer of wet pink in the dark wild bush. I could feel my cock painfully swell in my pants.
The skirt was ridiculously small. The red and gray tartan might have reached the top of a skinny girl’s thighs, but Lilly’s round, dimpled ass poured out the bottom of the hem. The top was practically sheer, and I realized the buttons were just for show. She would never be able to close them around her large tits, something she remedied by tying the shirt into a crop top that hugged her tits.
She looked… frankly quite silly. It was clear that Lilly was no schoolgirl. Her slight tummy hung over the waistband. Besides seeing her nipples through the shirt, I could also see the hairs sprouting from her armpits. Her thighs were like white rice with black sesame seeds, with the way her leg hairs sporadically poked out. It was a far cry from the porn model that wore it on the package. And she stood, staring at me. Waiting for what I would do next.
I reached for her, my hand sliding into her hair and quickly getting tangled. I started to pull her down and told her, “Now, you’re going to be the dick-sucking schoolgirl. And I’m going to be your teacher.”
And suddenly, she resisted me pulling her to her knees. Her shoulders were slumped, like she always seemed to stand, and she held firm. “What kind,” she said in her low, raspy whisper.
Annoyed by her delay, I heard Betty’s ‘Click, Click, Click’ in the back of my head.
“What?” I realized this was the first time I had heard her speak since she showed up at my house to give me the contract.
“Schoolgirl. What kind?” She didn’t look at me, just stared blankly into my chest.
“Um, what do you mean?” And as anxious as I was to get my blowjob, the sudden question threw me for a curious loop.
Her eyes began to move, her pupils bouncing side to side. It was like she was quickly reading over something that wasn’t there. She spoke with all the passion of a person reading a government form out loud. “Archetypes. Lots of schoolgirls. Cheerleader. Girl next door. Outcast. Bully. Nerd.”
“Nerd.” I was upset with myself for choosing so quickly. I wondered how long she would have kept listing.
“Why should I fuck my teacher?” It still seemed strange to hear the word ‘fuck’ from her mouth. Despite everything, there was a weird purity about Lilly. Something very sincere that the word ‘fuck’ seemed to contrast.
I shrugged. “Um, I don’t know.”
“Then why would I do it?” Fair question.
“Ok, fine. You need a better grade in my class.”
Immediately, she asked, “What grades do I normally get?”
The frustration grew, and with it, the incessant phantom, ‘Click, Click, Click’ seemed as real as my heartbeat.
“I… um…. does it matter?”
She blinked her black eyes, and for a brief moment, she looked up at my face. It was the first time she looked me in the eyes. “Yes.”
Alright then. “You are a straight ‘A’ student.”
“What grade am I getting in your class? And what kind of class is it?” Her pupils began bouncing again as she returned to her thousand-yard stare.
I fumbled over my words, trying to come up with quick answers and wondering how much more information she needed before she would just put my dick in her mouth. “Biology… no. English. I don’t know shit about biology. And you’re getting a ‘C’.”
Her eyes widened in almost anger. “Did I earn the ‘C’? Or was I set up?”
“Um… setup? Yeah. I’m blackmailing you.” She seemed offended by the grade, figured I’d better make it not her fault.
“How young?” That one threw me off.
“Wait, so can I name any age?” She didn’t answer. I thought about naming something disturbingly young, just to see if she would do it. But the idea made me suddenly feel disgusted with myself. But staring at her full breasts, I was able to put it from my mind and said, “Eighteen.”
Click. Click. Click. So fucking horny, the disgust yielded to the need quickly.
“Do I love my parents?” What the hell kind of question was that?
“Yes.” I was starting to get frustrated, wondering if there was an end to all this.
She nodded. I waited for more questions. Instead, she walked past me and went and sat at her desk. Curiously, I watched as she opened a drawer. She took out two hair ties and, using her turned-off monitor as a mirror, she made her hair into messy twin tails. Finally, she rooted around the drawer and found a pair of thick black glasses.
Before my very eyes, I witnessed a transformation.
It was strange; the body was Lilly’s. Hairy, thick, and wild. But she stood taller, her shoulders went back. And suddenly, she seemed younger and girlish. It was the way she moved, how she looked at me, even the way she breathed. Everything about her was different. She nervously looked up at me and asked, “Mr. Holler? C-can we talk?” I don’t know which was stranger: how her voice and inflection changed so dramatically that she sounded like a teenager, or to hear her call me by my last name.
She stared at me, waiting for my response. If I had just dressed her and told her to blow me, would she be doing this? Judging from the contract, most likely.
Instead, the wording of my request had started an entire scene. She was masterfully playing her part. The questions weren’t just a strange quirk; she was building a character around my answers. Just minutes ago, I thought she looked a bit funny as a grown woman in the trashy uniform. Suddenly, it all seemed to work. She was an awkward, vulnerable high school girl.
So the least I could do was be the pervert who takes advantage of her. “Lilly, come on in. How can I help you?”
“It’s just that… I really feel like you’re giving me unfair grades on my papers.” Her tone was higher-pitched with a slight nasal quality. Lilly acted bubbly, but nervous. Smart, but unsure. Already, this schoolgirl persona she had conjured had spoken more than Lilly had previously. “I’ve just worked so hard. Hours and hours on my last paper, Sir. And I see you giving other students much better grades for so much less.”
Click. Click. Click. I recalled the sensation of Betty’s jewelry running up the fly of my pants. And I found myself pissed how tightly Lilly pursed her lips.
“Unfair? Lilly, that’s quite the accusation.” I tried to roleplay with a girlfriend once, and it got uncomfortable as hell, and we abandoned it quickly. Lilly made it so easy to play along. I gave her a stern look, “Do you speak to your other teachers like this? I should knock you down another grade for this insolence alone!” She gasped in horror.
“NO! I mean… please no, Sir.” She fidgeted with the ties in her ponytails and rubbed the ball of her foot into the ground. Sure, the outfit was ridiculous. But the awkward way she carried herself, combined with the lack of grooming, made the nerd angle work all the more. “Please, I… I’ve never had a ‘B’ before. Let alone a ‘C’. Isn’t there some way for me to earn a better grade? I can’t disappoint my parents. I just can’t! Please, could I have an extra credit assignment? I’m begging you!”
She was so adorably desperate, which made me feel gleefully cruel. “No, Lilly. That wouldn’t be fair to the others in the class if I treated you differently.” I put my hand on her shoulder, and I could feel her tighten at my touch. “Unless… No. Never mind. Forget it. You’ll just need to take your ‘C’.”
She stepped forward and, tugging on my tie, pleaded, “Wait! Please! Tell me, I’ll do it! I’ll do anything! My family is poor, and if I don’t get all ‘A’s, I won’t get into the college my parents want! And if I can’t do that, then… then…” She choked on her words and pressed herself against me. “Please!”
I stared at her lips. Click. Click. Click.
I looked around, like someone could hear us, before sliding my hand down her waist and pulling Lilly close. “Little girl, can you keep a secret?” With my other hand, I let my fingertips caress the side of her breast.
With a gasp, she tried to pull away. “Mr. Holler! What are you doing?” I didn’t let go.
Instead, I held her tighter and cupped her tit in my hand, giving it a firm squeeze. “You want an ‘A’. I want to cum. We can make a trade. Girls here do it all the time, you know. That’s how the real world works. But first you have to tell me, can you keep a secret?”
Click. Click. Click.
Her hands were shaking. Her large, damp eyes stared into mine. Lilly was always looking away, never into my face, but she wasn’t herself right now. No, this schoolgirl wasn’t truly Lilly at all. This was the first time I really got to look into those dark eyes. They were absolutely breathtaking. Like obsidian.
Click. Click. Click.
This was a character she created just for this moment. Constructed from her library of erotica, using my parameters. Now I had this customized bookworm brought into existence for my pleasure alone. “And… you won’t tell anyone either. Right?” She reached up, pulling the knot that held her shirt closed. She blushed as her breasts spilled and her nipples dragged along the sheer.
“That’s right.” I lifted her breast, impressed with its weight in my hand. An awkward, squeaking moan pierced the air as I fondled her gently. “That’s real good. Lilly, have you ever gone down on someone?”
“Gone down?” I followed her eyes as they went down my body to my bulge. With a sudden understanding, she gasped and recoiled and covered her tits with her arm, shaking her head side to side. “N-no! Gosh, no! Mr. Holler! I… I … why would you… I’ve never even kissed a boy!”
I grabbed her by the wrist. I pulled her in by one of her pigtails. “Would it make you feel better if I kissed you first?” Lilly held her breath and nodded. I brought my face close. I could feel the wet warmth of her mouth on my chin. Her eyes closed, she leaned close and offered her trembling lips.
Click. Click. Click. The sound of jewelry against teeth rattled in my skull. The thought of Betty laughing as she teased me made my blood boil. Frustration. Cruelty.
I pulled Lilly’s hair hard and slapped her hard across the breast. Tears welled in her eyes, and her mouth gaped and squealed. My red handprint was so distinguishable against her white skin. “Teachers don’t kiss their little girls. It’s unprofessional. Now get on your knees, cock sucker.”
Her chest heaved as I pushed her down. Her eyes locked on my swollen cock as I opened my pants and pulled it out. I had never been this horny. The head of my dick had turned a dark purple like a vicious bruise. Cum dripped from my tip. Lilly began sucking in deep, gasping breaths, hyperventilating with wet tears falling down her cheeks. “Please… I… I…. don’t… know… what…”
She tried to choke out the words. And the more frightened she got as I brought the tip to her panting mouth, the more perfect she made this fantasy. My cowering little nerd, willing to do anything for a grade.
“M-mr. Holler…”
“Kiss it, all over.” She leaned in, staring at my cock like it was going to bite her. “You’ve only got your grades going for you. Can you live with a ‘C’? Are you alright with your parents knowing you’re a fucking failure?” Lilly shook her head, then adjusted her glasses. She leaned in and lightly pecked the head of my cock, a strand of cum sticking to her lip as she desperately looked upward. Begging me silently to tell her she was done. Instead, I pulled her face in closer.
It was a peculiar feeling, and amazingly enjoyable. She was shaking and gasping as she peppered my shaft with sweet, innocent kisses. Occasionally looking up at me, only to shamefully look away when I looked into her dark eyes, made even larger by her smudged glasses. Her pigtails bounced as precum dripped down into her messy hair. I cradled her face. Her tongue extended, licking my taut sack as I shushed her pathetic whimpering.
Click. Click. Click. Enough tenderness.
I put a finger on her lower lip and tugged it down. She clenched her eyes tight and let her mouth hang open. Her hot, huffing breath caused me to squirt a strand of cum into her throat. I heard her gag. That’s really what made me lose control.
Jerking her by both pigtails, I thrust my cock deep enough to feel my balls bounce from her chin. Lilly pushed against my thighs, trying to pull back. Overpowered, she quickly submitted as her mouth wrapped around me. She kept her eyes shut as shut as I ravaged her mouth. The glorious sounds of her choking and gasping for air brought me such savage delight. I never knew I could enjoy being so brutal.
And somewhere in the violent face fucking, as drool, semen, and tears ran down her face, Betty’s clicking was finally silenced.
I just wish I could’ve made it last longer.
Unable to restrain myself and desperate to treat Lilly with all the disrespect Betty taught me, I pulled her head back. She whined and squirmed as I pumped wet, sticky ropes across her glasses and into her hair. I was stunned by the sheer volume of cum on her face. I always wanted to blow my load into a girl’s face, but never had the guts to even ask. Article 5. I could do anything I wanted to Lilly. That made me feel as wonderfully depraved and powerful as I ever could have imagined.
I spent more time painting Lilly with ejaculate than I did fucking her mouth. As my balls drained and each pulse gave less and less, I pressed the tip of my dick against her cheek and spread the mess playfully across her skin. The entire time, she shivered and quietly cried. “A good ‘B’ effort, Lilly.”
Her eyes suddenly shot open, and she shamefully stuttered out, “B-b-but you said if I…”
“That was a little girl’s blowjob, and it only deserved a ‘B’. So don’t you dare fucking argue. But don’t worry. Like any good teacher, I’ll tutor you. Come to my office this time every week. And I’ll make an ‘A+’ cocksucking woman of you by the end of the semester.” She buried her hands into her face and sobbed as I began zipping up my sated and softening cock. And suddenly I was hit with a wave of guilt. I watched her blubbering, my postnut clarity creating a wave of guilt and convincing me I had crossed a line. That I had really scared and hurt her. “Lilly, I…”
And then, like someone had turned a spigot that turned off the crying. Her shoulders slumped. Her body relaxed. And the dead, expressionless look she normally carried returned. The pathetic nerd was gone, and Lilly Redwood was back. In all her understated animalistic glory. And for the briefest moment, the corners of her mouth turned up into a quickly fleeting grin while my filth dripped down her body.
And again, it was like I wasn’t there. Like I hadn’t just blown the load onto her face that even now was congealing on her alabaster skin. She took off the sticky glasses and ran her hands down her face, knocking the sloppy mess down onto her body. Her breath had already steadied. If her eyes weren’t red, I could have never guessed she was weeping. And without any regard for the degrading act I had done to her, she reached for her sweater and put it back on, trapping the mess on her body.
She sat back in her reading chair, raising her knees and digging her heels into the edge of the chair. Then, reaching under the tartan skirt, slid her fingers into the dark bush between her legs. Her mouth slacked open, and the unfiltered beastial grunting and growling of Lilly Redwood’s orgasm filled the air.
What I had done turned her on. A lot. Enchanted, I sat on the floor. Watching her fingers dance with her cunt until her body tightened. I ran my hand along her socks and watched her toes spread wide the closer she got. Lilly howled like a hit dog when she came, then slumped down into the chair and sighed contentedly .
The air around her smelled of sweat, sourdough, and leather. It was an intoxicating combination of potent odors. Unable to help myself, I grabbed her by the knees. Pushing them far apart, I watched her freshly pleasured pink cunt pulsing with pleasure from the break in her thick fur crown. I leaned further in, inhaling her sex. I looked up, honestly unsurprised to find she had already picked up her book to continue her reading.
That was easily the hardest I had seen her climax. And the only time I had seen her smile.
Satisfied for now, I stood up and wordlessly left her with my cum drying in her hair. My mind tingled as I considered all the outfits in the closet. All the people I could make Lilly Redwood be…
