School's Out

"Mr Watley, would you put just the tip in my ass?"

If you had told me 24 hours ago that a gorgeous nubile 18-yr-old would ask me to put my cock (just the tip) in her ass on the last day of school, I would have been floored. But here I am, presented with Ashleigh's succulent backside, and after a good twenty minutes of sucking on her full tits and eating out her sweet pussy and her tasty ass, she wants me to try fucking it.

Please don't think I am a pervy teacher. Far from it. A bit about me. I love history, and I love teaching. I was never interested in teaching upper grades, though. As the youngest sibling in my family, I had a lot of nieces and nephews who were younger than me, but not by much since their parents are my much older siblings. When it came time to choose a major in college, I knew right away I wanted to teach history, and teach kids.

After grad school, I started out teaching social studies for the lower grades at the private school where I am now, and did so for about a dozen years. I am good at it and love it. This past year, however, I was asked to cover senior year history because they were short on qualified teachers. It's been a huge adjustment, for sure. The teen attitude, for one. And what are they feeding the kids now?! Everyone – guys and girls, alike – look 22 years old. But a lot of good change as well. For example, being able to teach actual history instead of learning about the President. Again.

Luckily the students here are pretty good kids for the most part, even if they can be sullen or sassy, as teens are. Also, I know almost all of them since many started here as kindergartners. As such, I can recognize that many of the female students would be considered attractive or "hot," but I don't see them that way at all. To me, they are like my nieces. Sometimes they flirt with me, like they would with an uncle. I just laugh them off, and they would giggle "Oh, Mr Watley, you're no fun!" and turn around to torture some poor horny 18-year-old kid.

That is, until this year. Right after Christmas, we got a new student in the senior class, a transfer from another school in the area. Her name is Ashleigh, and she is like something out of a 70s girlie magazine. Her breasts are full and high (I shouldn't even be guessing, but I would guess an ample D cup but look bigger due to her small rib cage), and she has a classic hourglass figure – small waist, slim but rounded hips with a curvy butt. She is fair with a light spray of freckles, hazel eyes with long dark lashes, and long wavy raven hair that she keeps tied back or tied up. She is every man's dream, ages 18 to 88. Thank Christ I knew she had turned 18 in January, or else I would feel like a dirty old man pondering her charms. I mean, I do feel like a dirty old man, but at least it's not illegal.

I mean, I'm not that old. I just turned 38 but may look older due to my salt-and-pepper hair, which I keep quite short. I do keep fit thanks to all the running and indoor climbing I do. I think my physique is pleasing to the ladies, not least of which, my girthy 8-inch cock.

Ashleigh is so blindingly foxy that I can barely lay eyes on her. She's a B+ student, so her performance in class doesn't ask too much of me. She doesn't require accolades nor does she need propping up. She is reasonably friendly but otherwise keeps to herself and doesn't flirt with the boys as much as the other senior girls do. She hardly ever raises her hand so I don't call on her often. Anyway, there's no shortage of students who raise their hand, this being a prep school and the students very motivated, so it's not like I need to randomly call students out.

But sometimes when the students are doing independent work at their desks, I can't help but steal glances at Ashleigh – the soft pout of her lips, the long lashes, the leg line I can detect under her regulation navy skirt. I imagine softly kissing those pouty lips and slipping my tongue in her mouth. Or nuzzling her round breasts and sucking on her nipples. Or lifting her skirt and pressing my face into her girly panties. Or maybe turning her around and over my desk, peeling her panties down, and running my tongue up her ass crack, tasting her teenage musk...

Oh yes, dear reader, I am an avid lover of anally rimming the ladies. I mean, I love sucking pussy and all types of penetration as well, but the highlight for me is licking out the ass of a woman. Not every woman likes anal penetration, but in my experience, every woman loves to get her ass eaten out, even if she thinks she won't, at first.

There is nothing like parting a pretty woman's ass cheeks for the first time and discovering the texture of her anus and breathing in her specific scent. I love washing my tongue all around back there, spearing it inside her anal ring, lapping from her perineum to her pussy and clit, all of it. Blame it on my high school girlfriend who got me to do it on a dare.

Brrrriinnnggg! School's out!! I am shaken out of my reverie, and frankly I am thankful this marks the end of my trial year teaching older students. Take me back to my innocent primary school students, please! I take small comfort in knowing that I can only nurture these fantasies about Ashleigh because I never knew her as a girl. She arrived already a young woman.

It's the last day at school, hence a half day. Spirits are high, everyone ready to step into summer break. After the staff farewell lunch, I'm in my classroom tidying up and breaking a few things down to help next year's teacher with setup. There is nothing worse than coming back from summer break in late August and being faced with the detritus of the previous year. Talk about harshing your mellow!

I did mention to the senior students that a helping hand is welcome, but I'm not expecting hyper teenagers to come back to the classroom on the last day of high school. This is a pretty exclusive private school so many of these kids are about to jet off somewhere fancy or exotic. For me, it's just a short gig at a youth camp which helps to fund my 3-week rock-climbing trip I take every summer up North.

+ + +

"Hi, Mr Watley! You said you needed help?"

I turned around in surprise. Seriously, I invited the seniors almost as a joke since I was so sure no one would take me up on it. I drank in the sight of a statuesque teenage girl in front of me, in shorts and a tank top. Apparently, Ashleigh had changed into play clothes for the upper-classmen picnic. There was nothing at all improper about her outfit, but it also did nothing to conceal her playmate figure. Denim shorts that skimmed her hips and ass just so, a tank top that wasn't too skimpy but tight across her chest, and her feet encased in no-lace Converse slip-ons that conveyed a schoolgirl innocence yet accentuated her slim ankles and leg line at the same time. The man in me thinks she dresses this way for effect, but technically you can't find any fault with her attire.

"Oh, hi, Ashleigh. Uh, I didn't think any of you would come back. You get points for showing up!"

"Well, the classroom is a mess, I figured you need help. My parents are away, and my aunt is coming to get me and running late so I thought I'd come by and lend a hand. I mean, I wanted to help, anyway."

"Cool, thanks. I am grateful for the help. If you want, you can take down those posters on the Roman Empire."

She looks around, grabs a stool, places it by the wall where the all the Ancient Rome stuff was, and proceeds to pull them off the wall. Out of the corner of my eye – GenX perv that I am – I see her reaching up onto the balls of her feet, her calves flexing, her tank top lifting up to just reveal her midriff, her firm tits rising as she lifts her arms. Christ almighty, what a Venus. I have to look away and turn to work on another part of the room, tamping down my semi erection with my palm.

What a beautiful young woman. I would love to spend an afternoon luxuriating in her young, plush beauty – her soft lips, her full breasts, her warm flat belly, her pussy which I imagine would taste like syrup, and if I'm lucky, lifting her legs to munch on her ass hole. Oh, how I would love to make love to her ass with my mouth. I'm positive I could spend the better part of a day just exploring her soft corners and crevices with my tongue and fingertips.

"Where should I put this?" she asks, gesturing to a pile of display.

I'm shaken out of my daydream momentarily. "In the garbage, I think. Normally I would try to repurpose, but a different teacher will have this class next year."

"Really? You've been such a great teacher." She hesitated and added, "Although I felt like maybe you didn't think much of me as a student."

"What?? You were a fine student." (Really, really fine) "Why do you think that?"

"Well, you never called on me, for one thing." At that moment, it dawned on me that my seeming lack of attention to her in the classroom was misconstrued. Honestly, I found it too much of a turn-on and almost painful to look at her. But the effect was she thought I didn't have a strong regard for her as a student.

"No, it wasn't that..."

"What was it, then?" she asked, looking at me with those clear hazel eyes, her full lips slightly parted in inquiry. Good God. How can I tell her, 'because every time I lay eyes on you, I want to unbutton your shirt and lick your tits, or stuff my fingers inside your panties to check if your sweet cunt is dewy, or lift your skirt, spin you around and plunge my pervy tongue into your puckered teenage ass hole.'

"Er, I think maybe because you were new at the school and I didn't want you to feel singled out? I know most of the other students pretty well since many of them have been here since kindergarten or grade 1. Anyway, I didn't want you to feel picked on." I feel so lame and fake telling her this.

"Well, seriously, I wouldn't have minded being called on more often, Mr Watley." She flashed me a bashful smile, and is it my imagination or did I detect a faint whiff of teasing on her part. "I felt like maybe I made you uncomfortable, you know, being one of the older girls in the class and all."

"No..." My head is spinning a bit. Her teasing is just a little too much with all that I've been playing in my head. "No, that's not the case."

"Are you sure?" She comes a little closer and playfully touches me on my shirt placket with an index finger. I happened to look down (I've been working diligently not to look down) and see that her nipples are just slightly nudging through her tank top even though she has a bra on. Nothing overt, but how I ache to smooth my tongue over those nubbins. Suddenly, I realize this temptress can say anything and do anything at this point, and I am helpless under her power. I can feel myself salivating at the back of my mouth, the telltale hunger to cover her tasty bits with my spit.

"Yes, pretty sure. You're a good student. I'm sure you'll go far."

"How far?" She's now chest to chest with me – she's 5'7" to my 5'11" so a close match. She nods her head a bit towards one shoulder and gives me a sideways look. "Do you know why I transferred to this school?"

"No, I assumed your family moved here."

"Not exactly. I got in trouble at my last school for being too boy-crazy. I don't mean 'in trouble', just trouble, in general. Didn't you notice how I kept to myself, never flirted with the boys in class. I'm trying to finish the year without further incident." As a sort of punctuation to this revelation, she licks her lips and notches a thumb in the waistband of her shorts. It's surreal, but I feel like I'm in a real-life enactment of a scene from Lolita, except thankfully this Lolita is 18 and not 14, or however old Nabokov's anti-heroine was.

I'm stunned and just stand there. I literally have no words. Then suddenly she sweeps up her arms around my neck, stands on tip-toe, and plants a kiss on my lips. Her mouth is slightly open, but she keeps her tongue to herself. Small mercies. I reach up to disentangle her arms – we are still on school premises, after all – but she hangs on with the willfulness and strength of a teenager and presses her womanly hips onto my semi erection. Fucckkkk. She smells so good. All soap and water, a light hint of sweat from being outside at the class picnic, not to mention that undefinable sweet scent of a beautiful young woman just coming into her feminine power.

My head is spinning, I hesitate just a moment too long, and then it's too late and I find myself returning her open kiss, relieving a semester's worth of pent-up longing. I tentatively slip my tongue into her mouth and was surprised by her immediately sucking on my tongue. Oh, Christ. My hands are on her now, one on the side of her breast, and one reaching around and pressing her low back towards me.

We swap spit for a long while, her arms around my neck, her tits mashing into my chest, her hips cleaving to my thighs, her belly pressing on my cock. I have no plans to progress from here, yet I know I want to taste her everywhere. Especially between her legs and definitely where her ass cheeks meet. I wonder if a girl just graduating from high school would allow this. And what did she mean by boy-crazy? How crazy?

+ + +

I pull off her lips and turn her around so I can fondle her tits more freely and enjoy the feeling of her ass framing my cock. My God, I feel mentally undone. Ashleigh truly is every man's fantasy come true. She draws up her tank top to just above her bra. True to my earlier mental assessment, her tits do look to fill a D cup, but the flesh is almost spilling over the bra cups. Oh, my fucking God. I'm really an ass man, but right now I want to munch on those tits.

I reach up to undo the front clasp of her bra, and her wonderful breasts spring free. I fill each hand with a buoyant breast and rub my thumbs over the tiny pebbly nipples. My face is buried in her neck as she knocks her head back, lips parted, hips grinding into my crotch. The visual is every pin-up cliché you've ever wanked off to, except it's really happening to me at this moment in time.

I am aching to bring my lips and tongue to those nipples and gently turn her around. We're right next to my desk so I take hold of her hips and lift her onto the desk. I pause for a deep, wet kiss, our tongues swirling and discovering each other. Then I trail kisses behind her ear, down her neck and throat. She kicks off her Converses and wraps her legs around me. Just like a pin-up, she has beautiful feet with ruby-red toe nails. One day, I would like to have those toes in my mouth as I pound her ass.

My face is now at her chest, and I wrap my mouth around one of her perfect-10 breasts. I nip on it gently with my lips, teeth, and tongue, eliciting a soft moan from her. "Oh yes, Mr Watley, suck on my nipples, mmmm, your mouth feels good." I spend some time on that breast before reluctantly leaving it for its mate. Her breasts are beautiful: full, with a nice weight on the underside, and a slight inward curve on the top half culminating with the dark ruby nipple. She could be an artist's model. I spend at least five minutes going back and forth between these babies, leaving a faint trail of my saliva in my wake.

Then I proceed further south, planting soft kisses on her belly. I glance up at her to make sure her wants me to continue. Her eyes are shut and she's tweaking one nipple with her hand so I'm guessing it's good to forge on. I reach for the top button of her denim shorts. They're 501 cut-offs so I go on to undo the remaining buttons, following each undone button with a kiss on her warm, smooth skin.

As the last button becomes undone, I catch a whiff of her pussy, encased in her girly white panties with a cherries pattern. It is absolutely intoxicating. The last time I was with an 18-year-old, I wasn't much older myself. There's a chair nearby, and I dragged it over with one hand and sit myself down.

I hooked my fingers with an underhand hold on her shorts waistband and motioned to pull them off. My girl reflexively lifted her hips so I can tug them off. As they're coming off, I can see a wet spot in her panty, right between her legs. I pressed my face onto her mound and inhaled deeply. Oh, my sweet Lord. Her scent is tantalizing. I'm dying to lick her pussy.

She is softly moaning now and completely reclined on the desk and playing with both nipples with both hands. Her tank top is still on bunched up at the tops of her amazing tits, the bra unclasped and dangling to the sides, off-setting the mounds beautifully. She mewls her excitement, and I still have my face on her pussy through her underwear. I nudge my nose on her clit, again still through the fabric, and she responds with a whimper and raises her hips halfway to meet my face.

With a fingertip, I pull one edge of the panty back to reveal the side lip of her pussy. By what little I can see, her pussy is glistening. I hook my fingers in the elastic of her panty and start to roll it downward. Her bush is neatly trimmed in front which I love. But much to my surprise and delight, as I pull off the panty more fully off her hips, I see the real estate surrounding her pussy and behind is completely smooth. My cock is now straining painfully against my pants.

"Is that what high school girls are going now, shaving their pussies?"

"Hmmmm, I feel cleaner this way, plus I love the feeling in the shower when I soap up my butt. I keep some hair in the front so my Mom doesn't know..." My cock is still safely in my boxers, but I can feel it secreting a drip of precum as she tells me this and I envision her soaping up her bum in the shower, enjoying the smoothness of her backside... maybe a finger slipping into her ass now and then. Oh, how I would love to help her in the shower, maybe give her a fresh shave, then play with her slick asshole with my fingers and tongue, maybe eventually my cockhead...

I finally have her panties down past her hips and, keeping my eyes on her pearling pussy the entire time, I remove her panty entirely past her ankles and feet and put it to the side. I place one of her legs over and around my shoulder, while bending the other leg to rest the foot on my shoulder with the knee pointing to the ceiling. This way, I can see her ass a little better as I'm munching on her pussy. I cannot convey to you, dear reader, how horny and excited I am.

+ + +

I start to lap at her smooth cunt lips with my eager tongue. She is exactly as delicious as I imagined she would be. Her pussy is sweet and fresh tasting. I broaden my tongue to work her clit, alternating with a circular motion or turning my head slightly and licking at her clit with a side to side motion, every now and then diving my tongue into her honeypot. She is every bit a wet dream come true.

It's a good thing no one is in the building because she is starting to moan more loudly. Then she begins to draw the knee that's closest to her towards her chest, thereby exposing her irresistible rosebud even more. Hard to know if it was by design or she was simply hugging her thigh to herself for comfort. Still licking her pussy, I can now gaze at her anus at the same time. I start to angle my head so that my nose is closer to her ass. She smells incredible. Clean, beautiful, aromatic.

I am positively dying to rim her, but I'm also leery of freaking her out and ruining the moment. Then my girl does me one better and reaches down to gently graze her pucker with a fingertip. Oh, dear God. That's the only cue I need to stray my tongue in that direction. Well, she did say she liked the feeling of soaping herself back there.

I begin to lick her with long, broad, wet strokes... from her clit, dipping into her pussy, scraping along her perineum, and ending with my tongue swirling in her tightest hole. She is writhing her hips like crazy and has reached down to finger her clit as well. I bathe her hot box with my tongue this way for a long while, changing the angle every now and then.