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Sex Lessons in Chastity Hall

"Learning the forbidden joys of female sexuality"

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Senior year at Pine Creek Academy. An unfamiliar local number flashes on my cell-phone screen.

”Hi, Mary. It’s Wendy!”

Someone has the wrong number. But the voice is pleasantly feminine with a familiar intonation.

"Yes. This is Mary,” I tease.

"My, what a deep voice you have," Wendy says, quoting Little Red Riding Hood.

"All the better to please you with, My Dear,” I reply, paraphrasing Red’s fairytale antagonist.

"And how exactly would you do that, Mister Big Bad Wolf?” she giggles.

I’m evasive, but she insists I tell her what I mean, so I say the first thing that comes to mind.

"By showing you things you've never seen before."

"Oh, really! How do you know what I've seen, and what I haven't?"

"By the tone of your voice, My Dear," I tell her, winging it.

Actually, there is something about her intonation that makes me think of someone I met who attended Elm City College, a small evangelical school that caters to home-schooled students.

Like the more infamous Oral Roberts and Bob Jones Universities, students at Elm City risk expulsion for smoking a cigarette, drinking a glass of wine, or heaven forbid, "immodesty or inappropriate physical contact" with someone of either sex.

In other words, the polar opposite of Pine Creek Academy.

"You've endured a lifetime of intrusive supervision and over protection. Now you yearn to break out. To explore the forbidden mysteries of your own sexuality. But you don’t know where to start,” I tell her in my most authoritative voice.

“Are you psychic or something?”

"I get asked that a lot," I laugh.

We chat about random stuff. She is, indeed, at Elm City majoring in Music.

"There are rules against everything from smoking or drinking to watching porn or having sex. Any kind of sex. Get caught and you will be publicly humiliated and then expelled. At least the tuition’s a bargain and there's a Chick fil A in the student center.”

"Just my kind of place."

“Doubt that," she laughs. "I've heard all about Pine Creek Academy. I bet you even live in that dorm, what do you guys call it? Chastity Hall?"

"Actually, I do," I confess. Chastity Hall is the nickname for our Honors Residence Hall.

"Is it true? Girls and guys on the same floor. No visitation rules."

“Yup, just like the real world,” I say. “But only Juniors and Seniors over sixteen with an Honors GPA are eligible.”

Wendy is intensely, almost salaciously, interested in life at Chastity Hall.

We talk late into the night. The conversation is sometimes indirect, but we touch on solo and mutual masturbation, voyeurism, exhibitionism, and even oral sex.

Every time we broach a new topic, I assure Wendy that I’d be delighted to demonstrate. She dances around my offers. Never accepting them, but never rejecting them either.

Toward the end, I confess to having had an erection for hours. With a very sweet giggle, she confides the conversation had been very "exciting" for her as well. Before we said goodbyes, she promises to call again.

I drop my phone in my pocket and nearly knock over my desk in the rush to find a tube of lube.

About 8 PM on Friday my phone chimes.

"Hi," Wendy whispers. "Is this the Big Bad Wolf?"

"Yes," I whisper back.

"Did you really mean what you said about ‘showing me things I've never seen’?”

"Absolutely!”

"Can I come over?"

"Anytime," I tell her, redirecting a pile of dirty laundry from my bed to the closet floor. “But right now is good.”

"In about an hour?"

"Just knock twice, and say it's Little Red Riding Hood." When we disconnect, my heart is pounding the way it does when I take off downfield on the first pass-play of a football game.

An hour later, there’s a hesitant knock at the door.

"Mister Wolf?" a nervous voice asks.

On an impulse, I swing the door open and I sweep the girl standing outside into my arms, kissing her passionately. It's not Little Red Riding Hood.

It is Wendy.

She resists for an instant, then returns my kiss with pent-up passion. When I open my eyes, I see two girls gawking in astonishment.

Breaking off, I lower Wendy back to floor.

"Geeze," they whisper, “That’s hot!"

"Um… Jason," Wendy stammers, a deep blush rising in her cheeks. "These are my friends Mary and Liz."

It would be a stretch to call them beautiful. Attractive? Yes.

In a plain vanilla sort of way.

Mary is a redhead, Wendy and Liz are brunettes. They all wear clothes that reveal next to nothing about their figures. Nor do they seem acquainted with eye liner, mascara, foundation, luminizers or even lipstick.

But their eyes sparkle at me from behind bashful smiles.

I usher them in, thankful that as a Resident Advisor, I have a small suite with a separate bedroom.

"The real Mary, I presume," I say approaching the redhead, lifting her into my arms, and planting a kiss on her cheek. She squirms, giggles, then grabs the back of my head and presses her lips against mine in an awkward, but affectionate kiss that she seems reluctant to end. With our lips locked, I can’t help but wonder if what I know from experience about natural blondes goes for redheads as well.

Maybe I’ll find out tonight.

Mary has a little more heft than Wendy, but is still on the petite side. Liz is the full-figured member of the trio. She is only a few inches shorter than me, and when I wrap my arms around her waist and pull her close, she thrusts her breasts against my chest.

I don’t try to lift Liz into my arms, but I can’t help but fantasize how my cock would feel riding in the valley of her ample cleavage.

I'd expected Wendy to be alone, but when faced with a new challenge, I always try to rise to the occasion, so to speak.

I gather them around me, and sink onto one knee, like a quarterback in a football huddle. In the United States, evangelical roots may be deep. Devotion to football is even deeper.

The football playbook is the gospel by the prestige of U.S. colleges and universities rise or fall each Autumn weekend. The huddle is football’s most sacred ritual. The three women respond to being drawn into my huddle by looking down at me with a mixture of awe and nervous expectation.

"Stop me if I'm wrong," I begin, scanning their faces. “None of you have ever had a serious long-term relationship with a boy."

I look from Wendy to Mary and Liz. No one contradicts me.

“You’ve never seen or touched a real penis. Never watched one become erect or ejaculate.”

They are a little shocked, but again, no one says I’m wrong.

"So, tonight we’re opening a new playbook. Together we are about to change all of that," I announce, clapping my hands for emphasis. They glance shyly at each other, and from the unspoken looks they exchange, I again detect no disagreement.

"All right, then, let's get started.” I stand up and pull my shirt over my head and toss it on the sofa.

Their expressions are priceless. But I have the downfield momentum on my side and I’m not about to squander it.

I take Wendy's wrist and place her hand on my chest, then guide her fingers down my stomach, across my abs, and let them graze my belt buckle and the front of my jeans. While I’m not exactly Rambo, I’ve been in a serious weight training program for five years and my musculature is way more developed than your average doughboy-college student.

On a hunch, I put Wendy's hand back on my chest and let go. This time, she moves at her own speed, tracing my pecs, my stomach and even my abs with her fingertips.

She hesitates a moment at the top of my jeans, but continues past the belt buckle, and down the zipper, brushing her fingers across my cock and then down my pant legs, squeezing my thigh before letting go. When I let out an involuntary sigh, she smiles triumphantly.

I repeat the exercise with Mary, who not to be outdone, uses both hands, squeezing and exploring my chest and stomach. Upon reaching the front of my jeans, she spreads her hands across my abs and works her way down until her fingertips brush up against my stiffening cock. She grabs it firmly through the denim and squeezes rhythmically, studying my face with a wry smile.

Not until I groan from excitement does she release me.

Liz, the least inhibited, makes a perfunctory sweep down my chest, then reaches straight for my package. She fondles me with a firm, but not painful grip, and deliberately brushes her breasts against my chest. When she finally lets go, she makes a little fist pump before placing a wet kiss on my cheek.

There’s no turning back now. I unbuckle my belt, release the snap of jeans and pull down the zipper. All three girls watch as if in a trance as the jeans ride down my legs to the floor.

Underneath I’m wearing gray cotton briefs. I can feel my cock expanding under their gaze, fighting against the fabric until its size, shape and even the the little ridge around the head are plainly etched into the thin material.

Before anyone can move, I whisk Wendy in my arms and carry her through the bedroom door. Her eyes are wide with surprise.

In a hoarse whisper, I assure her, "If I do anything you don't want, just tell me to stop. I will. I promise." She makes a gulping motion, but nods her head in agreement.

Once inside, I kick the door close behind us, not completely shut, but enough to block the other girls' view. Setting Wendy back on her feet, I kneel beside her and lift the hem of her dress. I kiss the freshly revealed skin, swirling my tongue along the back of her calf and behind her knee. She gasps in surprise, but does not stop me.

An instant later, I pull the dress over her head. She raises her arms to help.

Holding Wendy’s dress in one hand, I pull off my briefs with the other, then step back through the doorway buck naked.

Mary and Liz are frozen like deer caught-in-the-headlights. I fold the dress before setting it on the sofa, well aware that the whole time my cock points straight out from my abdomen and bounces up and down with every gesture.

"You're welcome to join us in a few minutes. Just leave your clothes here," I tell them, patting the sofa for emphasis. "You can keep your panties on… if you want."

Wendy hasn't moved an inch, but she is about fifty shades redder with a blush that has fanned out across her chest and cheeks. I dim the lights and sit on the edge of the bed. With Wendy slightly above me, I place her hands on my shoulders and gaze into her pale gray eyes.

I see a hint of self-consciousness, but mostly Wendy gazes back with pure lust. Then she focuses on my erection, which is pointing at her tiny bra-covered tits.

"Can I touch it?"

"Of course. Can I take off your bra?"

"If you want.

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There really isn't much there."

She's right about that. My overweight Uncle Harry, has bigger tits than Wendy. But what she has looks deliciously pert with puffy pink areola and stiff little nubs. I gently pinch her nipples as I feel her warm fingertips touch the shank of my cock. We gasp in unison.

"I can't believe I'm doing this," she whispers.

"You’re first time touching one?”

“Unless you count copping a feel of a marble statue," she says. "It's so… so soft and hard at the same time."

"All the better for making love, My Dear," I reply. Her blush deepens, but her bashful smile says she's loving it.

We remain like that, Wendy standing above me, one hand on my shoulder for balance, the other exploring my cock and balls.

At first her examination is almost clinical. Eventually she experiments with different techniques, watching my reaction. By lightly stroking the shaft, she discovers, my cock involuntarily twitches, which seems to fascinate her.

While Wendy explores, I place my hands on her hips to keep her steady. She's wearing baby-blue cotton panties with a little lace trim on the waist. I notice the damp spot forming low on the center panel.

"Are you getting wet?" I ask. She merely looks at me and nods, before returning her attention elsewhere.

I reach cautiously between her legs until my fingers find the point where her pussy lips first bud out from her perineum.

I squeeze through her panties as softly as I can and Wendy's whole body shudders in response, her eyes wide and full of surprise. I squeeze again. This time the tremor is less perceptible, but the faint smile on her lips says she likes what I’m doing.

I work my way along her pussy, until I’m rolling her clitoral hood between my forefinger and thumb. By now, she is writhing in my arms, her breathing is fast and shallow and punctuated by loud gasps. In a single motion, I roll her body onto the bed so her legs hang over the edge at the knees and the soft space between her legs is exposed.

Before Wendy can protest, my head is between her thighs and my tongue lapping ferociously at the now saturated gusset of her panties. I alternate between fluttering my tongue against her clit and sucking on the wet cotton, which makes a loud swizzling sound, almost like using a straw to get the last drops of a milkshake.

Soon, Wendy is writhing and moaning."Oh, my, God!" she repeats over and over as her climax builds. For an instant, there is silence as Wendy's legs clamp down on my head, her back arches, and her body goes rigid. The wailing moan that follows is powerful enough to rattle the window panes.

I wrap her in my arms. Wendy's eyes are closed and a contented smile is forming on her lips. Then she begins to giggle. Softly at first, but building with such abandon that I can’t help but laugh with her.

When our laughter finally exhausts itself, there is soft knock at the door and Mary peers inside. Wendy and I are lying side-by-side with her hand absent-mindedly toying with my cock.

"Umm," Mary asks shyly, "Do you think I could have have a turn now?"

Mary's pale skin glows in the dim light. She has a more womanly figure than Wendy.

Her waist is narrow, giving way to broad hips. She wears the same kind of plain white cotton panties as my first girlfriend, Gretchen. If I hadn't already been rock hard, the image of Mary's pussy lips pressing against the crotch panel of her white panties would have done it for me in a New York Minute.

Probably less.

I follow a smiliar game plan with Mary, starting with my fingers and finishing with my mouth and tongue. Mary is more passive, and far less vocal, but there is no doubt when she climaxes. Even through her panties, my mouth is flooded with warm girl-juice. As Mary recovers from her orgasm, I notice Wendy has been watching us intently.

When it dawns on the girls that I haven’t cum, they insist on taking turns attempting their first hand job. I worried that after so much stimulation, I would cum instantly. But their inexperience is painfully obvious and neither Wendy or Mary is able to get the right rhythm going. After a few long and futile minutes, I wiggle free of their grip.

I had, quite frankly, forgotten about Liz, until her face peeks through the door. Her figure is what might be called BBW. Big-boned with plenty of padding. But also curvaceous with tits the size of cantaloup melons.

There isn't enough space for all four of us to fit comfortably in the tiny bedroom, so I ask Wendy and Liz to wait in the study, and promise to fetch them for "the finale."

I guide Liz so that she stands in front of me. Having her bare breasts hanging inches from my lips is infinitely distracting. Liz immediately wraps her fingers around my cock, and its obvious she's either had some practice, or is perhaps just a natural talent. Her fingers fall into a very pleasant rhythm almost immediately. This, too, is a major distraction, but I manage to progress with the game plan to the point where I’m about suck her plump pussy lips through the gusset of her panties, when she completely surprises me, by pulling them down and tossing them on the floor.

Even more surprising is Liz's pubic mons which bare and baby smooth. A bit lower, the size of labia is in keeping with her other dimensions, and I have no trouble sucking each one into my mouth. If there is a problem, it is that Liz almost instantly loses her balance, sways left, then overcompensates to the right before tumbling directly on top of me.

All my years of pumping iron pay off as I’m able to catch her in mid-collapse and redirect the trajectory of her fall so she lands on the bed, with me touching down beside her. As she realizes we are both intact, she breaks into a rumble of deep, lusty laughter. I notice two small faces peeking in the door, then vanishing when they realize that Liz and I haven’t gone completely around the bend.

"Can't… take so much… stimulation down there…" Liz stammers.

"So I noticed," I say, letting my hands wander over her breasts and stomach. I give her a long time to relax. Eventually, her breathing and composure return to normal and I send my fingers lower until I am, at last, able to stroke her pussy lips and ever so slowly glide one finger inside while lightly rubbing her clit with my thumb.

It's not long until Liz explodes with in an orgasm, and explode is exactly what I mean. A gush of warm liquid erupts onto my fingers and bed, accompanied by the powerful aroma of sexual arousal.

I've always been keenly influenced by certain olfactory signals, and the fragrance of Liz's orgasm has an instant effect. A shiver runs down my spine, butterflies flutter in my gut, and my cock twitches uncontrollably.

"Girls," I shout. "Wendy… Mary… Now!"

An instant later, their faces appear at the door and they step carefully inside. I am kneeling over Liz, who looks up at me through the hazy afterglow of her orgasm.

I lower my cock in the deep cavern between Liz's prodigious tits. To her credit, Liz picks up on my intention and cups her breasts until I'm almost completely engulfed by her soft, warm skin.

After no more than a dozen long, slow titty-fucking strokes, I’m hovering on the edge of orgasm.

“So close,” I moan, going into overdrive. My abs and butt tense and my hips start thrusting on their own accord. My balls are slapping the underside of her tits as I reach a final, furious frenzy.

Liz arches her back, forcing her breasts ever more tightly together. I watch through half-closed eyes as she smiles at me mischievously the leans forward and licks the head of my pulsing cock.

The erotic after-image of Liz's open mouth and tongue reaching out for my cock, takes me over the brink.

"Cumming,” I cry, pulling myself from between her breasts, and rising up so I'm pointing at the bull's eye of her nipple.

I am neither exceptionally endowed, nor a prodigious cummer. But after hours of teasing and stimulation, I erupt with uncommon fury, groaning deep in my throat as perhaps half-a-dozen pulses splatter on Liz's voluminous tits. My climax is rewarded with the enthusiastic squeals from Wendy and Mary, and a look of utter astonishment from Liz.

Wendy and Mary throw on their dresses and scamper down the hall and return with warm, wet towels.

Surprisingly, as soon as Liz is clean and I’m coherent, they shuck off their clothes again. We adjourn to my little study with its couch and stuffed chair, and sit around discussing what's just happened. I try to offer little gems of wisdom about hand jobs and sucking cock, but the conversation has a way of always working back to the same question. How exactly does a guy jerk off?

Finally, I put one of the damp towels across Wendy's knees, and stand up to and provide them with a detailed commentary and demonstration of male masturbation. With the three of them watching in fascination, it doesn't take long.

"Can I see your pussy?" I ask Mary as my orgasm nears.

She smiles knowingly, probably because she realizes why I'm asking, and does a sweet little strip tease, slowly revealing the V of her pubic mons one millimeter at a time.

Just as the brilliant ginger hue of her public hair comes into view, I arch my back and close my eyes.

There are only few spurts this time, not especially thick or forceful, but enough to provoke giggles of delight.

Not long after that, Wendy reminds everyone of the consequences of missing their Midnight curfew.

They dress quickly, but leave reluctantly, with many long kisses and lingering touches.

“Just one question, Jason,” Wendy says at the door. “Didn't Little Red Riding Hood get eaten by the Big Bad Wolf?”

“Well,” Liz interrupts before I can say anything. “Weren’t we all?”

* * * * *

“Sex Lessons in Chastity Hall” is part or a series of related stories about sexual awakenings and adventures. Previously stories in this “Smallville” series are:

Grinding with Gretchen (1)
“Feel me,” she whispered, guiding my fingers between her legs
A football scholarship takes me to a private academy where I meet Gretchen, the achingly beautiful Senior girl who shows me the pleasures of mutual masturbation.

Tracy’s Mom (3)
It wasn't Tracy, but Tracy's Mom who watched me intently from the darkness
My first time. I fall hopelessly in lust with a sexually alluring woman twice my age.

Tommy’s Naughty Mommy (5)
A cub and a cougar. But who’s seducing who?
I woke up to find Tom’s Mom sitting by my bed, gazing at my cock with hungry eyes

Still to come:

Gina Is a Gymnast (2)
"Ever see a naked gymnast?" she whispered, unfolding a three-sided mirror
I’d known Gina almost all my life, but had never really taken notice until the night she helped mend my broken heart.

Lita Can't Cum (6)
“Standup and take off all your clothes,” I told her. “I want to watch”
She’s seventeen. You're almost forty. There’s no way it can happen. There’s no way to resist.

Published 
Written by Jason_NYC
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