Dr. Bad Boy

by Ainsley Booth

  M: Speaking of Friday night…What will you wear to work that day?

  V: What would you like me to wear?

  M: A white blouse. Some kind of skirt.

  V: Like a sexy librarian?

  M: Something like that.

  V: Can’t wait.

  We exchange a few more texts back and forth, little words that should mean nothing. But I find myself not wanting to tell her to go to sleep. I want to keep talking to her all night. I want to call her and hear her voice, but if I do that…I don’t know.

  I don’t do it, anyway.

  And once the texts stop, and she’s said good night, I wish I had.

  Friday can’t get here fast enough.

  The end of the week finally arrives. I get home an hour before I’m expecting her, and I set out her outfit.

  The kilt that makes me rock hard every time I look at it.

  Purple Doc Martens, because I want her to be a bit mouthy with me. Bad-ass schoolgirl, not an innocent in Mary Janes, although if she likes this game, we can play it that way another time.

  And a pack of Hubba Bubba bubble gum.

  I’m dressed up, too. I wore jeans to work today, but when I got home and showered, I put on dress pants, and a buttoned down shirt, top button undone, and a loosened tie.

  She’s the mouthy schoolgirl.

  And I’m the principal that’s had enough.

  Downstairs I move some furniture around. The spanking bench might get used, so I pull that out from the wall, sliding the ottoman over. And I pull one of the wingback chairs closer to my toy cabinet.

  Then I turn off most of the lights, so when she comes downstairs, all she’ll see is me sitting in that chair.

  I hear the garage door open, then the quiet click of her letting herself in. A pause as she looks at what I’ve laid out.

  A chuckle as she figures out it’s not exactly naughty librarian night in the kink factory.

  I take my seat and wait.

  She’s been such a distraction in class. Teasing her teachers and upsetting the other students with her shocking stories of what she did on her vacation.

  We can’t have that kind of behaviour here at Donovan Academy. As the principal, it’s my job to lay down the law. Dole out punishment.

  Ensure that all our pupils—even mature students like Ms. Roberts—contain themselves.

  And if they can’t…

  Well, then there are consequences.

  I see the Docs first. Then her legs, her long, lean calves and curvy thighs, clad in black stockings. A flash of thigh above the curving silk, held up by the black ribbons of a garter belt, then the kilt.

  A flash of anger pulses through me.

  How dare she wear such short scrap of nothing when our dress code clearly demands all kilts touch the floor when kneeling.

  She’s knotted her blouse in the front, too, revealing a slice of pale skin at her mid-section.

  And her long chestnut hair, usually long and flowing free as she flits in and out of my office, tempting me, is now parted right down the middle and braided loosely, two plaits, one falling over each shoulder.

  Even her braids look fucking dirty.

  She’s perfect.

  Pleasure twists with the anger I’ve manufactured and I clear my throat. “That’s far enough, Ms. Roberts.”

  She stumbles to a stop.

  Then she pops her bubble gum.

  Fuck me. Beyond perfect.

  “You wanted to see me, Max?”

  “How many times do I have to tell you to call me Principal Donovan?”

  “I dunno. Does it really matter?” She shrugs and her tits jiggle.

  I don’t think she wore a bra to school today.

  I picture her beautiful lingerie left upstairs on the chair. Everything except that garter belt.

  “Discipline is at the core of our teaching philosophies, Ms. Roberts. Even though your circumstances for being here are…unusual…the normal rules must still apply.”

  She pops her jaw to one side, then the other, her eyes doing a lazy look around the darkened space. “But I’m different than the others, aren’t I…sir?”

  My sexy fucking kitten. Trying to figure out the bounds. I stand up and prowl toward her. I want to see that insolent pout up close. Bite that lower lip and push her to her knees in front of me, maybe. Put it to better use. “You’re different, all right. When I allowed you to attend Donovan Academy as a mature student, Violet, it was under a very express set of rules. Do you remember what they were?”

  She shakes her head, her eyes wide. Of course she doesn’t. I’m making this shit up as I go.

  “Rule number one. You must at all times follow the dress code.”

  She swallows hard. “That’s a hard one for me to remember…Principal Donovan.”

  “I can see that,” I say dryly. “On your knees.”

  She lowers herself in front of me.

  “Does your hem touch the floor?”

  She shakes her head in answer to my brusque question. “No.”

  “What happened to the rest of your skirt, Ms. Roberts?”

  “I sold it for drug money.”

  I snort, unable to keep myself from laughing, and I can see she’s fighting back a smile, too. “You think that’s funny? You think I don’t know what to do with a smart mouth like yours?”

  She looks up at me, pure innocence on her face until she shrugs.

  I unbuckle my belt, taking my time. Watching the look on her face slide from innocent to hungry. “If you insist on dressing like a horny little slut, then we’re going to have to put you in the alternative curriculum program.”

  “I am a horny little slut,” she breathes, her eyes big and her cheeks pink. “But I really like my regular classes.”

  “We can’t have you distracting the others, Ms. Roberts.”

  “I’m sorry, Principal Donovan.”

  “You should be.” I sigh and unzip. “Maybe this will teach you a lesson.”

  “Your cock?” she asks, then gasps as I fist myself firmly, making the head even darker for her. “It’s so big.”

  “You’ve seen a cock before, then?”

  She flutters her eyelashes. “In pictures…”

  “And in person?”

  “I don’t think I should tell you.”

  “But that was rule number two, Violet. We have no secrets here. You’re not being a very good student right now.”

  “I want to be,” she whispers.

  “Then tell me,” I growl. “Have you held a man’s cock before?”

  She nods, her sass fleeing as she realizes I’m serious about punishing her like this, on her knees.

  “And have you taken anyone in your mouth before?”

  A nervous shake of her head. Lying slut. I tap my cock, heavy and hard, against her lips. “Then it’s time to teach you.”

  She opens her mouth and slides all the way down my length.

  Then she pulls back and shoots me a triumphant look before swallowing me whole again.

  “Tsk, tsk, tsk, Violet. You’ve not only lied to me about having taken someone in your mouth, you’ve deprived me of training that lovely throat of yours. Slap my thigh if you need to safeword.” Using her braids as handles, I take control and start pumping my hips. Slowly at first, getting a feel for what she can take, then I pick up speed, bottoming out deep her throat with each thrust.

  Fuck, she feels so good, and it’s not long before I’m ready to come. I’m tempted come straight into her throat, but right now I want a visual.

  Letting go of her braids, I pull out and grip my dick in my fist. “Open wide, tongue out. When I’m done, I want you to swallow every drop.”

  Spurt after spurt lands on her tongue. With the last shot, she makes a show of swallowing, then licks my cock clean without me saying a word. Fuck, she’s so damned perfect. I tuck myself back in and fasten my trousers, leaving my belt unbuckled.

  “Up,” I say as I grab her by one braid and start tugging her along
. “When did you learn to do that?”

  She gives me a coquettish look. “A man took me to his hotel room once and I didn’t know how to do what he wanted. Then he was too careful and said we’d work on training, and I needed him to be able to take what he wanted." She gives me a careless shrug, sticking to the roleplay even as she shares her secret. "So I practised.”

  This revelation pleases me more than I’m willing to let on.

  We stop next to the sofa where my favourite cane is lying on the middle seat, along with a leather strap and a wooden ruler. “Over the arm.” As soon as she’s in position, I flip that scrap of skirt up over her back, baring her gorgeous ass. “The man didn’t mean the royal we, did he?”

  “Um, maybe?”

  “Regardless, acting on your own initiative robbed me of pleasure. And now it’s time to pay up. Wrists crossed behind your back.”

  I glide my hand over her ass, then give each cheek a sharp slap. I love to see my hand print appear on her pale skin. I’d love to see the red welts of my cane in contrast to her ivory complexion, but I think it will be quite some time before she’ll be able to take a caning without any warm-up, so welts against pink, it will be.

  Using the ruler, I gently tap her ass all over. I want her ass as uniform in colour as I can get it for her warm up so when I lay down the cane stripes, there will be a definite contrast.

  When I’m satisfied with the colouring from the ruler, I’m almost ready to move on to the leather strap for a deeper pink.

  But first, I have a little surprise for my naughty student. Reaching into my right front pocket, I pull out a small zip-close freezer bag and hold it in front of Violet. “Know what this is?”

  “No, Sir.”

  From the puzzled look on her face, she’s telling me the truth. “It’s ginger root that I lovingly peeled and carved this afternoon just for you.”

  The size of it doesn’t even come close to the plugs I’ve been using to train her ass, but evil me is very much looking forward to her reaction.

  The purpose of the exercise is to torture her asshole, not my dick, so I pull out an exam glove from another pocket and snap it on before pulling the ginger plug from the small bag.

  “This is called figging, Violet. Have you heard of that?”

  She surprises me by nodding.

  “Where did a model student like you learn about such a filthy act?”

  She smirks. “We both know I'm not a model student.”

  “Good. Then I can assume you've also learned about safewords?”

  “Yes.”

  “Maybe not a model student, but apparently an advanced one. Tell me what yours are, Ms. Roberts.”

  “Red and yellow.”

  “And your colour right now?”

  “Green.”

  “Excellent.”

  Lube isn’t necessary, and in fact, is undesirable as it diminishes the effect of the ginger, which is slippery enough to insert without more discomfort than intended.

  Using my fingers and thumb of my left hand, I part her cheeks, then place position the plug at her exposed asshole and slide it quickly into place before she has a chance to react. “Whatever you do, Violet, do not let it go. Safeword if you need to.”

  As soon as I dispose of the glove, I pick up the strap. I begin a little on the gentle side because we’ve had a little time since I’d pinked her up with the ruler.

  “Is this supposed to burn, Principal Donovan?”

  “Absolutely, Violet.”

  “Not the answer I was looking for.”

  “What was that?” I ask as I squeeze her ass-cheeks together.

  “Thank you?”

  I resume my rhythm with the strap and it’s hard not to chuckle every time she clenches her ass from a smack and then loosens it right away from the increased intensity of the ginger.

  Once I think she’s the right shade of pink, I switch out the strap for the cane I’ve been itching to use for weeks.

  I pin her wrists to the small of her back with one hand, then lay the first stripe across her sit-spot. It’s my favourite area to place the harder strokes because I want them to remind her of me whenever she sits down.

  She squeals as her ass clenches, then quickly releases. “Colour?”

  “I’m green,” she says, but her voice is pitched higher.

  The next stroke is a little harder, and it lands just above the first. This time she lets loose an almost scream that makes me grin. He ass cheeks twitch and flex, and I wait until she settles again before laying the third and final stripe.

  It’s much harder across the fullest part of her rear and elicits a scream that makes my dick ache.

  “Next time I need to take the cane to you, Ms. Roberts, you’ll count each stroke. Understood?”

  “Yes, Principal Donovan.”

  “I doubt it, but you will.” I release her hands and toss my cane back onto the sofa cushion, then reach into my back pocket for a condom and undo my trousers.

  As soon as my dick is covered, I press it against Violet’s slick entrance and slam home. I position my hands on her hips so I can use my palms to squeeze her ass cheeks together in order to make the most of that ginger plug in her ass while I pound my cock into her pussy.

  Before long, I’m close, and tempting as it is to deny her orgasm, I’m not quite that mean. Not tonight. I let go of her ass and reach around her front and worry her clit. When I feel her start to clench around me, I cup her breast with my other hand and pinch her nipple as I take the last few thrusts to push me into oblivion with her.

  I don’t know how she does it, but every time we’re together, she takes what I give her and makes it even better.

  As soon as I slip out of her body, I quickly deal with the condom, then grab a tissue from my pocket and use it to remove the ginger.

  She starts shivering and I grab the blanket and wrap her in it, then settle her on the sofa. “Just give me a minute to dispose of a few things, kitten.”

  As soon as I’ve done a quick clean up, I sit on the couch and slide Violet into my lap. “You were amazing,” I tell her as I slide a piece of chocolate between her lips.

  “The cane was amazing. I could probably do without the ginger, but the cane was definitely amazing,” she murmurs around the chocolate.

  And if she wasn’t my dream woman before, she is now.

  25

  Violet

  I’m starting to measure everything against the countdown to Friday nights. Three weeks in and I’m breathless with excitement as I pull into his garage and park my car next to his.

  What does he have in store for me tonight?

  I take a final sip of my water and check myself in the rearview mirror.

  Goodbye, Regular Violet. I’ll see you on Sunday.

  Inside, the house is nearly as quiet as always. From downstairs, I hear music playing, though, which is different. It sounds like Florence + The Machine.

  Interesting.

  I look for tonight’s outfit, and at first, I only see a pair of shoes. Sexy, gorgeous shoes. Purple, of course, dark patent leather, with a four inch stiletto heel and a delicate ankle strap.

  And beside them, there’s a small package.

  I pick it up and look closely at the black label.

  Well, this will almost be the same as being naked. I flush all over as I pull off my t-shirt and yoga pants and take the fishnet body suit out of the package.

  At first I worry he bought the wrong size, but it stretches as I pull it up my legs and over my hips, then tug it up my torso.

  No, this isn’t the same as being naked.

  It’s better and worse at the same time. The open loops put my sex on display. But it’s also very flattering, highlighting curves and visually disrupting any critical assessment of my flaws.

  Not that Max has ever done that. Not even once. When he inspects me, it’s always with appreciation.

  I slide my feet into the heels and do up the ankle strap, then I make my way downstairs.

>   Max is standing at the bar, pouring himself a drink. He’s still in work clothes. Suit pants, a dress shirt. Shiny oxfords and a heavy leather belt. I hesitate for a second, then make my way to the ottoman and assume the position.

  Each clink of ice in the glass is like a pinprick against my skin. He shoots me a glance. His mouth is already wet, his eyes bright.

  Is he drunk?

  A tremor of something…fear? Danger? Danger, yes. Fear…not yet. But there’s the promise of that. The promise of…we’ve been playing by the rules. Well inside the bounds, these last few weeks.

  Maybe tonight I’ll call him Doctor. See if that makes his eyes burn.

  I lower my head and focus on holding my posture. Legs wide, spine straight.

  My mind clears. Thoughts fade. And Max approaches like a panther. He paces around me, ice clinking with each step. The angsty, driving music in the background fades, setting the scene still, but all I hear is his drink sloshing in his glass—which of course I can’t really hear, but I do all the same.

  He stops beside me and trails his fingers up my back, his fingertips tripping over the soft netting encasing my body. “Did you have a good day, kitten?”

  “I did, yes. Thank you.”

  “I didn’t.” He sighs and takes a sip. “I’m wound tight tonight. Remind me of your safewords, please.”

  “Red.”

  “And?”

  “Yellow.”

  He takes another sip, audible even over the music. “You may need them tonight. Do you understand?”

  “Yes, Max.”

  “Good.”

  He moves in front of me. His erection is visible through his dress pants, heavy and thick. He sets his drink down on that antique metal tray and slowly undoes his belt, sliding the leather across his hands before coiling it and setting it next to his drink.

  Then he loosens his cuffs and rolls up his sleeves. First one, then the other, pausing in between to take another swig.

  His glass is almost empty, and I don’t think it’s the first he’s had tonight.

  “You’re trembling, kitten.”

  I try to make myself stop, but I can’t. I open my mouth to explain, and nothing comes out. I think about safewording. Not red, but yellow maybe. I trust him, but no drinking and kinking is a rule, right?