Dana & Holly Ch. 03

Story Info
Dana and Holly play a game of principal and bad student
6.7k words
4.38
40.2k
13

Part 3 of the 5 part series

Updated 10/26/2022
Created 02/03/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"This is where the spankings go"

I'm damn near drooling on my toast as I look at the picture and read the words. I'm on the road right now, in my hotel room, eating breakfast. On my phone is an email I just got from Holly. Whenever she can't accompany me on the road, we send each other naughty pictures once or twice a day. This morning's photo is a pic of Holly's ass; she's wearing red satin panties with a big white heart on the butt, and her asscheeks are bright red from a fresh spanking. Emblazoned across the photo are the words "This is where the spankings go."

"Damn right, that's where the spankings go," I think to myself. "Thank God, I'm going home today." The trips without Holly always suck – no sex, and... well, just no Holly, in general. Buuuuut... I'm flying home today. My plane leaves in a couple hours, and when I get home, I'm gonna take that little minx over my knee and give her a prize paddling. Contemplating whether or not to rub a quick one out, I realize that my hand is already inside my robe, tugging and twisting my nip. "No!" I tell myself, "not yet. I'm gonna wait until I get home, and when I finally cum, it's gonna be all over Holly's hot mouth. Hell, I'm gonna squirt in a bucket and watch her drink it all down."

Repressing my need for an instant O, I set the phone down and finish my breakfast. It's a mediocre breakfast, but it fits the bill. Getting up to finish getting ready, I send Holly a response: You better be wearing those panties when I get home. "I hope this flight goes quickly," I think to myself. I'm already imaging what else Holly might be wearing, and just what I might do.

Within a few minutes, I'm packed, ready, and loading up the rental. I check out of the hotel, get to the airport, drop the car off, and catch a shuttle to the terminal. Check-in goes fairly smooth, and soon I am in my seat and waiting for takeoff.

Four hours later, I'm walking off the plane and into the terminal. A quick scan of the waiting area, and I find my baby, Holly. She quickly walks toward me, and we hug, kiss, and say hello. God, she looks stellar! She's wearing a baby blue cashmere sweater, a silver mini-skirt, and stiletto heels. Every guy in the room is tripping over himself, especially when they see this wet dream of a girl come up and kiss her lesbian lover.

After getting my bags at baggage claim, we head out to the parking lot. Once inside the car, we kiss again, but this time, a lot more passionately. Our tongues are dancing a tango. Holly squeezes my boob hard. My hand slides up her skirt. Her pussy is on fire! "Did you wear those panties?" I ask her.

"Yes, Dean Campbell."

That's her plan, I think with a grin. Bad college student goes to see the dean. I like it. "Home, Holly," I instruct her. "We've got some catching up to do."

The drive home seems to last forever, even though Holly is racing to get there. It's just the anticipation, I know. The whole ride there, I'm running my hand up and down her thigh, but I take care to leave her pussy be; I don't want her to have a wreck. Holly went straight for my cunt, though. I'm in the passenger seat; it doesn't matter if I have an orgasm. Still, though, I push her hand away. "Not yet, Babe. I'm saving it." With a nod, she puts her hand back on the wheel and steps on the gas.

The miles finally pass, we pull in the driveway, and Holly parks in the garage. Getting out of the car, I tell Holly that I want her to take a shower with me, as plane flights always make me feel a little grubby.

Inside the house, we head for the bedroom. I drop my bags, we both drop our clothes, and head for the bathroom. Once the water is warm enough, we both climb in. Holly washes me in a hurry – her touch is welcome, but we both just want to get out and get it on. Once we're done bathing, we climb out of the shower and dry ourselves off, staring at each other all the while.

As soon as I'm done drying myself, I pull Holly close and shove my tongue in her mouth. Our hands are all over each other. We're both in such a hurry. I lay the towels on the floor and tell Holly to lie down. With her prone on her back, I get down and move to straddle her face. "This is what I've been saving it for. I want my first cum to be on your mouth."

"All right," Holly says eagerly, grabbing hold of my hips and pulling me down onto her waiting mouth. Her tongue lashes my dripping pussy with a vengeance; I can barely last half a minute. I grunt and grind and grab her hair, smushing my quim down onto her face, trying to force-feed her my gushing juice. Desperate to taste all of me, she sucks it all down.

Once my orgasm subsides, I finally breathe and collapse to one side. Holly climbs up on one elbow and looks at me with a sloppy face. "Nice to see you, too," she says. We laugh, hug, and just look at each other for a long minute. Helping me up, Holly says, "Now then, Dean Campbell, it's time for detention. I'll meet you in the office in 10 minutes." With that, I go to my room to get dressed, and she to hers.

Digging through my clothes for anything that looks sexy, I throw on a black skirt, crotchless panties, black stilettos with a silver heel, and a blouse with an extra button undone, so that my braless tits are visible. Some quick lipstick and blush, and I head for the office.

The office isn't a real office. I don't need one. It's just a room we set up for us to play in, so it's loaded with sexual devices. Darling Nikki would be jealous.

Entering the office, I shut the door, check myself in the mirror, and take a seat at the desk, waiting for Holly to come in. A minute later, I hear her knock. "Come in," I say. The door cracks open, and Holly sticks her head in. "You wanted to see me, Miss Campbell?" she asks sheepishly.

"Yes, Holly. Come in."

She enters the room, shuts the door, and sits in a chair across from me. I can see she's wearing a school girl outfit, but she sits too quickly for me to see the whole package. Sitting in the chair, she's got her heels backed up on the chair legs, knees together, and her hands tugging on the hem of her skirt, pretending to be nervous.

"You're in my office again, Holly. More trouble."

"Yes, ma'am."

"Since you were last here, two weeks ago, you were caught last Thursday kissing another girl behind the bleachers, with your hand inside her shirt. On Sunday night, a room check after curfew found you asleep in another girl's bed."

"Yes, ma'am."

"You pulled down another girl's underwear in the hall, causing her to drop her books. Two of your teachers claim that you repeatedly sit on the front row and raise your skirt, so that your upskirt view is plainly exposed."

"No, ma'am! That's not true! I..."

"Hush, Holly. This isn't the first time."

She backs down, and looks at the floor.

"And then in a locker check today..." I pause for effect, and it works; her head snaps back up. I open a drawer and look down at its contents. "We find this in yours."

I pull a large red strap-on dildo out of the drawer and slam it down on the desk; the dildo is about the right size for me, but with Holly's tiny pussy, she's going to feel it a bit. Holly slumps in her chair; she's defeated. "Stand up," I tell her. "Push the chair back against the wall, and stand in front of the desk." She does as instructed; with the chair out of the way, I have plenty of room to play with my prize. I get up and walk around the desk to check her out. She's wearing a red plaid skirt, a white blouse with the tails tied around her waist, white knee-high socks, and saddle shoes. My pussy is getting really moist.

I walk in a slow circle around her. I grab a tuft of her hair and smell it. Standing in front of her, I dip my head and sniff at the base of her neck and shoulder. Holly stands rapt. "Spread your legs," I instruct her. She complies, spreading them a little more than shoulder-width. Leaning back against my desk, I ask her rhetorically, "How many times is it, Holly? Six times, just this semester?"

"Yes, ma'am. I think so."

"You're a bad girl, Holly." She doesn't respond. "You know this is a private college... for wayward girls. Your parents didn't just send you here for an education; they want you to get your act together, and they don't care how it happens. So long as they get results, I can discipline you however I please. Isn't that right, Holly?"

"Yes, ma'am."

"And how do I please, Holly?"

"Sex, ma'am. Here in your office. Lots and lots of sex."

I stand up and walk slowly around her. "What kind of sex, Holly?"

"Dirty sex."

Standing behind her, with both hands on her tits, I whisper in her ear, "Are you a dirty girl, Holly?" I lick the back of her ear.

"Yes, ma'am. I'm a naughty girl."

"And are you feeling naughty today?"

"Yes, ma'am. Very naughty. You look really hot today! I watch you a lot."

"Hmmph. I want you to do something, Holly. Go sit in my chair."

"Ma'am?"

"Go sit in my chair, and pull it up to the desk, just like it was yours."

Holly sits in my chair, pulls up to the desk, and looks to me for instruction.

"I keep hearing about you flashing your teachers. I want to know what your upskirt looks like." Grabbing a pocket flashlight from the top of my desk, I get down on my hands and knees. All desks have a cutout in the back for your legs to fit under, but my desk is also cut out in the front; it's great for when I want somebody to crawl underneath and lick my pussy while I work.

I turn on the flashlight and crawl under the desk towards Holly's knees. She's got her legs spread as far as the desk will allow. Gawd, this is delicious!! One of her hands is toying with the hem of her skirt. "Hike your skirt up, Holly, just like in class." She slides her skirt up a couple inches. "Stop toying with me, Holly! Do it like you do for Miss Anders." She slides her skirt up a couple inches more, exposing all that creamy young thigh. Her cookie is plainly in view. Oh, wow, this is too much. Holding the flashlight up, I crawl forward towards my prize in her panties. Every inch forward, the excitement builds. I feel just like that guy in The Breakfast Club.

As I get close, I see that she's wearing those red satin panties, like I instructed. Getting closer, I can see her pussy lips mashed against the fabric. It's beautiful. Still moving forward, I press my face against her pussy and breathe in her smell. It's intoxicating. She's very wet; I can see a wet spot on the front of her panties. I kiss her thigh. She flinches. I lick her other thigh. She shudders. I plant a big kiss right on her pussy, and give it a lick. Her hand is on the back of my head, and I can hear her breathe deeply.

I back out of the cubby hole and stand up. "That's lovely, Holly. Maybe I should substitute for one of your teachers one day." She blushes at the compliment. "Now, then, stand up and turn around." I command her. She complies. "Let's take a look at you," I say. Walking in front of her, I untie her shirt tails, unbutton the blouse, and slide it off her shoulders. Her luscious tits are hanging freely. Squeezing them like melons at the store, I'm amazed at their plumpness; they're so firm, big but not huge, and their shape is so perfectly round, just exactly the way you imagine good boobs should be. Tugging at the nipples, I compliment them, "These are beautiful, Holly. I could play with them for days."

"Thank you, Dean Campbell."

"How do they taste?" I ask, looking her in the eye as I dip my head. I take the fat, pink nipple in my mouth and suck on it lovingly. It's growing in my mouth. I rake my tongue across it. Moving to the other breast, I kiss it on the side, then run my tongue in a circle around the new nipple. It's so delicious. I bite down with my teeth, just hard enough to grip, and give it a long tug. Holly's breaths are deep and audible. Reaching in a drawer, I pull out some nipple suckers and clamp them on. She takes sharp breaths as the suction cups squeeze tightly. "There we go," I say. "Very nice." She gives me a smile.

Letting go of her breasts, I tell her to turn around and bend over the desk. I sit in the chair and pull up closely. Her ass and creamy thighs right in front of me, I flip up her skirt, so that her ass and panties are exposed. On the back of the panties is the big white heart, just like in the photo. Just above the heart, I spy something that wasn't visible in the photo: In small, white embroidered letters is the exact phrase she quoted me – "This is where the spankings go." I'm speechless for a second.

Collecting myself, I start smacking on the ass. "Well, you're just asking to be spanked, aren't you?"

"Yes, ma'am. I wore these just for you."

"Is that so?" I yank down her panties, so that her bare parts are exposed. "You know, Holly, as much as you're in here, I think you're doing it on purpose."

I spread her cheeks. Her asshole stretches, and her pussy lips part, exposing the pink insides. She stays quiet.

"What did I say?" I question her, smacking her ass.

"Yes, Dean Campbell, it's true. I like coming in here."

"And why is that, Holly?" I slide a finger between her lips, feeling the slipperiness.

"Because no one fucks me like you do."

I spread her cheeks and spit on her asshole. "What's that again?"

"No one fucks me like you do. You're so naughty, Miss Campbell!"

I stand up and lean over her, sticking my finger in her mouth so she can get it wet. "Thank you, Holly. You're a dirty girl, too. Very dirty." My finger all sloppy, I slide it in her ass, all the way to the knuckle. She takes a sharp breath. Sitting back down so I can look at her parts properly, I tell her, "Depending on how you take your punishment, I might have some other plans for you." I twist my finger, and slide it back and forth, watching how her O-ring stretches and tugs. "We'll talk later."

I pull my finger out, suck on a second one, and slide them both inside her tight little bunghole. With my other hand, I rub my thumb in a circle over her clit. She moans in appreciation. Her feet slide apart a couple inches. I work my thumb on her clit, first in a circle, then up and down. The little pearl is peeking out at me; I give it a couple flicks with my fingernail. "Ooo-ooo-ooh," she moans. Her pussy is getting wetter by the second. "I bet you'd like to cum, wouldn't you, Holly?" I ask.

"Yes, ma'am."

"We can't have that. You're being punished, remember?" Her hips are rocking a little.

"Yes, ma'am."

"It's not punishment if I don't make you work for it." Her knees give a little. Grabbing a vibrator, I tell her, "This is what we're going to do, Holly. I'm going to hold this vibrator against your clit, and then I'm going to count to ten. You're going to hold that cum, and when I get to ten, then you can cum. Understand?"

"Yes, ma'am."

I turn the vibrator on medium and press it against her clit. She jerks at the contact. I slowly start counting down.

10... 9... 8...

Her juices are running down her legs.

7... 6... a long pause 5...

She's moaning very loudly, and her hands are gripping the edge of the desk. "Pleeeeeeeaaaaasse," she utters.

4... 3... and then I take the vibrator away, ripping her near-orgasm away from her. She collapses on the desk.

"Not yet, Holly. I think you need to hold on that cum for a while longer. You just hold it inside, and I'll let you cum when I think you've earned it." I set the vibrator down and go back to focusing on her asshole.

"Yes, ma'am," she gasps. "Thank you, ma'am."

My two fingers still inside, I wiggle them around in her ass, sliding them in and out, then stretching them as wide as I can, which isn't much; her ass is really tight. "Your asshole is really tight, Holly. How long has it been since you've had anything in here?"

"A long time, Miss Campbell. You were the last."

I was shocked. "Noooo, it can't be. That was a month ago."

"Yes, ma'am. It's true. Someone did give me a really small buttplug, and I've used that a couple times, but really, I've been saving it for you."

"I'm flattered, Holly. I'll be sure to give your asshole proper attention today." I shove my face between her cheeks and slather my tongue all around, making all kinds of sloppy noises. I wrap my lips around her asshole and suck it into my mouth as hard as I can. It's so pretty and pink and tight. "How does Student Assistant sound? We can play a lot more. I'm sure sometimes I'll need help at home on the weekend. Would you like that?"

"Yes, Miss Campbell! That would be awesome!"

"Well, I haven't made up my mind yet," I say, in between slurps. "You need to impress me some more."

"Yes, ma'am. I'll be a dirty whore for you!"

"We'll see," I tell her, giving her ass a hard smack. "It's time to give you a spanking, since you seem to want it so badly."

"Thank you, ma'am," she replies, wiggling her butt in anticipation.

"But first, we need a butt plug. I need to loosen you up." Reaching into the desk, I pull out a penis-shaped butt plug, about 3 inches long, and not quite an inch and a half thick. After lubing it up, I hold it against her stinkhole and start pushing it in. I work it in slowly, pausing to let her asshole loosen around it, backing it out when I need to. After a couple minutes, the shaft finally slips in to the tapered end, and the disc-shaped base is flush against her cheeks.

"How's that, Holly? Does that feel good?"

"Yes, Miss Campbell. Very nice."

I pull her panties back up, so the heart is right over the sweet spot. "I have to loosen your ass up before I fuck it. Besides, I love to see that butt plug outlined through your panties. Now, take your skirt off and get up on the desk."

Holly drops her skirt to the floor, climbs up on the desk and gets on her hands and knees. "Turn that way," I tell her, so that she is stretched out lengthwise across the desk. From out of the file cabinet, I pull out a horse bit for her to wear. I put the bit in her mouth, and then fasten the straps around her neck. "It's okay, honey," I tell her, patting her on the cheek. "I'm not worried about you making noise. I just like the look of that bit in your mouth." Going back to the file cabinet, I tell her, "But it's true, I do kinda like it when you can't speak."

Reaching in the drawer again, I pull out a black leather paddle. I slap it against my palm as I walk back towards her. Holding the paddle up so she can see it, I point out the heart-shaped cutout in the leather. "See that, Holly? That heart cut in the leather? Just like your panties?" She nods. "Mmprhf." I rake my fingernails across her torso as I walk towards her eager ass. "That cutout leaves a heart-shaped mark on your ass when I smack it," I explain.

SMACK!

"Just like the heart on your panties."

Her eyes go wide. She bites down on the bit.

SMACK!

"You know, Holly, I really don't care for hard spankings."

SMACK!

"Mmmprrhf!"

"I prefer light spankings. A little pain can be fun. Heavy pain is not my bag."

SMACK!

Holly is drooling all over the desk. Her ass is bright red... with pale hearts.

"But you asked for a hard spanking, didn't you?"

SMACK!

"Didn't you, you little whore?" I ask firmly.

"Mmphrfh!"

SMACK!

"All right. That's enough," I say, setting down the paddle. I gently trace my fingernails across her butt cheeks and down her thighs; they're warm to the touch. I plant soft kisses on the heart-shape marks that will be there tomorrow. After walking around the desk, I undo the straps on her bit. "Time for you to pleasure me, Holly," I inform her. The bit is sloppy with drool. "Clean that up," I command her. "The desk, too." She licks and slurps all her saliva off of the bit, then sucks it up off the desk. "Now, get down here and undress me."

Holly quickly gets on the floor and walks to where I'm standing in the middle of the room. Standing behind me, she unzips my skirt and slides it down to the floor. She kisses my ass all over and sticks her face into my crack. "You're so beautiful, Miss Campbell!" Picking my skirt up off the floor, she looks to me for direction. "Put it there on that chair by the door," I tell her. She lays my skirt out flat on the seat of the chair, then hurries back to me. Standing in front of me, she first unbuttons the cuffs on my blouse, then undoes the buttons down the front. "I love these things," she says, as my bra-less boobs become visible. "They're gorgeous!" My tits aren't really big, only a B cup, but they're really firm and perky from all my exercise. With my shirt still draped over my shoulders, Holly lowers her head to my chest. She squeezes and sucks on my tits. She licks the tender underside. My eyes close and I take deep breaths. Holly stuffs as much of the boob into her mouth as she can get, her tongue flicking my nipple repeatedly, then she does the same with the other breast.

12