Annie wants to go out.
She doesn’t tell me, of course. It’s the long shower in the evening. It’s the way she pulls her sleek black hair back into the same French twist. It’s the stylish makeup and the little black cocktail dress that comes almost to her knees. It’s the sheer, black silk stockings on her slender, perfect legs, and the Italian heels that scream ‘fuck me’, even though no one will ever do that again.
After dinner, Steve drives us to a classy hotel with a bar. I usually leave it up to him – he knows what we’re looking for, and he knows why we don’t want to become too well known at any of them. He’s always had a knack for finding new hunting grounds.
Annie parks herself at a table in a dark corner. I sit at the bar, nursing a martini. It’s a chilly Monday evening in March, and the business crowd wanders in to wind down and maybe find a little warm comfort for the one or two nights they’re in town.
Two women prattle at the far end. While the redhead yaks, the blonde with dark eyebrows tosses a glance my way. Then she does it again. That’s the signal. I’m a catch, and I know it. Firm jaw, dark skin, blue eyes, and silk suit, but it’s the silver highlights that draw them in like flies to honey. Annie would approve of her, but something about this one say she’s a local. That wouldn’t do at all.
A nicely dressed auburn haired woman sits halfway down the bar. The jewelry is knock-off, and she’s a little too available. Hooker. A high dollar one, too. Over the years, I’ve learned to spot them. Even though the trust fund would pay for a lifetime of thousand dollar pros, Annie gets difficult when she thinks that I’m paying for it.
A charm bracelet full of possibilities meander through: short, tall, slim, heavy, black, oriental, redheads, blondes. I get a first look from most of them. The clincher is the second look, the one that lasts a moment longer and says “Play your cards right, and I could be yours.” A half dozen make a conspicuous offer, but none seem quite right.
A woman with mousy brown hair steps up to the bar, two stools down. I can look past her and see that Annie noticed. The woman looks like a schoolteacher – attractive and well-dressed, not frumpy, but somehow slightly out of place with the rest of the clientele. She orders a daiquiri, strawberry. I was right – this is a martini and white wine crowd. She’s in over her head.
There’s the first glance, and a smile. I nod pleasantly. If she’s up for it, this might be fun. We still have a long way to go. She rifles through her handbag – strictly Sears – and pulls out a ten. Definitely not from around here.
I see it coming, the look that lingers, a broader smile, then her surreptitious glance downward, checking the lie of her breasts. This is the one.
Peering back over my shoulder at Annie, she is staring blankly toward the schoolteacher. When she finally notices that I’m looking at her, she immediately turns her head, but not so much that she can’t watch. She approves, too.
I catch the eye of the bartender when he brings her drink, and silently signal to put it on my tab. When she hands him the ten, he smiles and pushes it away, gesturing toward me. Her smile is brighter now. I move to the next stool over.
“Hello,” I shake her hand – no wedding ring. “My name is Mason, Mason Stamford. And you are…?”
“Carolyn, with a ‘y’,” she replies. “Carolyn Hunnicutt.”
Closer up, I see her makeup is understated, pale lipstick, and extra foundation that barely covers a line of freckles across her nose. I’ll bet she has more between her breasts.
“I haven’t seen you here before,” I tell her. The fact is, I’ve never been here myself.
“Yes, you’re right,” she says shaking her head. “I’m just in town for a seminar that ended late. All of the hotels uptown were full, so they stuck me way out here.”
“What sort of seminar?” I ask, leaning a little closer.
She doesn’t back away. Good.
“It’s ‘Approaches to Shakespeare’. I teach high school English, and they’re showing us how to modernize the master “
“Does Shakespeare need modernizing?” I ask. Her eyes are dark brown, and dilated. I can almost smell her arousal.
She chuckles, “Yeah, that’s what I said. My master’s thesis centered on Hamlet’s treachery, Rosencrantz and Guildenstern…”
” ‘ I hold ambition of so airy and light a quality that it is but a shadow’s shadow’ ” I recite.
Carolyn gasps and grins wide. “You quote Shakespeare?”
“I played Rosencrantz at Harvard,” I admit, feigning a shyness. That sets the hook. “Would you like another daiquiri?” She’s already gulped down the first. She’ll be toasted soon, and that should make her more pliable.
“Oh, I shouldn’t,” she says unconvincingly.
“You don’t have to drive anywhere, do you?”
“No, I guess not,” she acquiesces.
I motion to the bartender. The schoolteacher will need a lot more medication for what comes next.
“Where do you teach?” I ask.
“Not far. Gladesboro.”
That could be a problem. Still, it’s just far enough bahis firmaları away, and I wouldn’t expect to see her in this sort of bar. Quickly peeking at Annie, I notice she is staring toward Carolyn again. Apparently, we both agree on tonight’s catch.
“So what do you do, Mason?” the schoolteacher asks. “Besides Shakespeare?” She downs half her drink in one swallow.
“Oh, I dabble,” I answer honestly. “In my spare time I enjoy sailing and painting. Oh, yes, and my orchids. I have a small conservatory where I grow a few orchids.”
“Orchids” she repeats, dreamily. The rum is having its effect.
My face is closer now. I feel the soft, heated tufts of her accelerated breaths. Like iron to a magnet, she is drawn toward me.
With a voice nearly a whisper, I ask, “Is anyone waiting for a call from you?” It is an offer, a last chance for her to escape..
“No.” She accepts the offer, her lips gently curled into a knowing smile, her eyes coy.
Excellent. No boyfriend.
My finger hooks under her chin and lifts. Our lips touch, her eyes closed. I press harder; she responds, opening to me.
She is ready.
This is the hard part, where I lose most of them. When they actually see her, many excuse themselves. A few run away. Sometimes we go home empty-handed. I stroke the schoolteachers neck, run my fingers through her hair while I explain what is going to happen. Her eyes grow wide, as expected. I direct her attention to my sister in the corner, and prepare for the worst.
She looks, then turns back to me, wearing a smile. “Okay,” she says with an agreeable lilt.
It is I who is shocked. None of them ever smile. I’ve been slapped, kicked, cursed, had drinks thrown in my face, but never a smile.
Then she adds softly, “I understand.”
My jaw tightens. How can she possibly understand? How can she comprehend what it’s like to know that you’ll never have anything more than an endless stream of one-night stands with strange women? How can she possibly grasp the embarrassment, the rejection, the dull ache in one’s heart from a lifetime of no emotional response from the one you hold dearest?
Suppressing my moment of indignation, I leave a hundred for the barkeep and escort the schoolteacher through the lobby. It’s easier when I don’t remember their names. Annie dutifully falls in tow.
Steve, patiently waiting down the street, sees us at the door and immediately pulls the limo to the curb. The doorman opens for us, the schoolteacher on one side, Annie on the other.
The teacher looks at Annie, then up at me. “Have you done this before?”
I nod. None of the others ever asked. They mostly try to ignore her.
“She enjoys watching the motion, right?” she asks.
Annie gazes emptily toward the floor. I’m sure we’re in her peripheral vision.
“Yes, I think so. It’s so hard to know.” I admit.
“I’ve had two in my classes – a boy and a girl. I learned a lot.”
The schoolteacher reaches to my far cheek and turns my face, tilts her head upward, and we’re kissing again. This time, it’s for real. She’s animated, passionate. She unbuckles her seat belt, peels her jacket off, and throws her leg over my lap, straddling me. Tilting her pelvis forward, her crotch finds my erection, and she rubs herself against it vigorously, squirming and moaning.
“Mason,” she pleads, “I want your hands on my breasts. Now.”
I begin unbuttoning her blouse.
“No,” she demands. “I want it now. Rip it, I don’t care.”
Seizing the lapels, I jerk them apart. Buttons fly everywhere. On the other side, I see Annie’s head jerk. We have her attention.
“Yes!” she sighs. “My bra, too!”
Who is this woman?
With a snap, the center clasp gives way and matronly breasts burst from their binding. They are stout and pale, with dainty blue lines and pink teats. She lifts one to my mouth. Fueled by her sexual energy, I lean in and suck.
She rocks back and forth vigorously, stimulating herself against my stiff cock and muttering, “Fuck, Mason, your dick feels so good. I can’t wait to fuck you.”
I never knew schoolteachers could be this hot. If she keeps this up, I may climax before she does. I hope Steve’s getting a good show.
Annie sure is. From the corner of my eye I can tell that she’s is staring at the teacher, but there is a strangeness to her gaze – it is not hollow. Maybe it’s the angle of her brow, or the curve of her lips – did she lick them? They’re wet. If she had an emotional response, I would call it ‘yearning’. I’ll bet that she’s wet. No one has ever gotten her this bothered in the car.
Steve pulls up to the house and opens the door for Annie. The schoolteacher tumbles out next. Standing in our drive, her ragged shirt hanging open in the cool night air, she gapes up at our house.
“Holy shit!” she murmurs.
Annie briskly leads the way inside. I pull the schoolteacher stumbling along behind me. As I lead her through to my bedroom, she gawks at the splendor of the quaint little Stamford chateau.
“Mason, are you kaçak iddaa the governor, or something?” she asks, awed.
“No. If you’d like, I can introduce you.”
“Who the fuck are you?”
“I’m just a man,” I answer. “I have a special sister, and I’m lucky enough to have a little extra money and plenty of time to care for her.”
Annie has already taken her usual chair in the corner of my bedroom, where she can see everything. The teacher spins slowly, taking it all in. She stops to reverently caress the carvings on the Louis XIV four-poster.
“This is gorgeous,” she whispers.
“You are gorgeous,” I tell her. “The bed will look even more beautiful with you on it.”
She smiles at me, then glances past me at Annie, and suddenly remembers why she’s here. Keeping her eyes locked on mine, she sheds the torn blouse and bra, kicks off her pumps, unzips her skirt, and pushes her panty hose down. She is naked, and she is gorgeous. So many of the women I bring here are like models – too perfect, unblemished. The schoolteacher has character: a soccer-mom face, noticeable biceps – does she work out? – a lovely roundness to her belly, a wild, untamed bush between her legs, and curvaceous thighs. And I was right – a cute patch of freckles is sprayed between her breasts.
She comes to me with lust in her eyes and kisses me greedily, devouring my tongue, all the while maneuvering me to the side so that Annie can see it all. The teacher unbuckles my belt and drops my trousers while I remove my jacket, tie, and shirt, letting them fall to the floor. Sinking to her knees on the thick Persian carpet, she takes me in her mouth. I am surprised at how talented she is, and how much of me she can take. Her head bobs enthusiastically, and she grunts with a steady rhythm, giving Annie a good show. My sister’s is gripping the arms of her chair tightly, and I can see the rapid rise and fall of her chest.
Rolling my balls in her fingers, the schoolteacher has me boiling in short time. I try to warn her, but she is intent. With a roar that grows from deep in my chest, I explode against her tongue, and she drinks most of it, letting the last few spurts splash against her cheek and chin for effect.
She wipes most of the drips from her face, and licks them from her fingers, then she sucks me clean.
I lift her by the armpits, and kiss her lovingly. I’m tempted to ask if she was ever a professional.
“Thank you. That was…” I pause, searching for the right word. “…exceptional.” In fact, it is the best blowjob I’ve ever had.
“I was a senior in college before I let my virginity go,” she explains. “I had to be good to protect myself.”
I grin. “But now I’m incapacitated for a while. What ever shall we do?” I muse, rubbing my chin as though deep in thought.
“Hey buster,” she says, grabbing my arm and leading me to the bed. “This ain’t the matinee. I’m here for all three acts.”
She falls back on the thick mattresses, spread out. Her pussy is wide, wet, and pink. Slowly, I work my way up her legs to the lush, tasty prize at the junction. She is quite a performer. Her plentiful ass wiggles and squirms. Loud, unexpected expletives erupt from her pretty little schoolteacher mouth between grunts and squeaks and moans. She comes exuberantly, screaming and yelling profanities that would curl most teacher’s hair.
Immediately, she pulls me up on the bed and straddles me. With three quick thrusts, our pelvises come together. She begins riding me spiritedly, bouncing and careening on my erection. I push her over and mount her, thrusting ferally while I suckle and nibble at her pink teat. It becomes a battle for dominance. Each of us strains against the other, rolling over and over around the bed.
“Fuck you!” she shouts in mock anger when I force myself on top.
“Fuck you, bitch!” I answer back, ramming my cock into her.
We are lewd and savage. Like rutting animals, we wrestle and claw and bite, wild and barbaric. It is the most athletic and fun lovemaking that I can recall. I want to remember this woman. What was her name? Carolyn, with a ‘y’, she said.
I withdraw and roll her over, twisting her arm around her back. She screams rude epithets at me, but raises her ass, presenting herself, and grunts with heavy satisfaction when I lunge from behind.
“Fuck me!” she begs. “God damn you, Mason, fuck me!”
I slap her plump ass, and she yelps. I do it again, harder, and she cries, “Yes, you sonuvabitch!”
Rolling her back over, I jump off the bed and lift her, and she impales herself on me, her legs locked around my waist. I press her back against the heavy, carved bedpost, kissing her while we fuck. Reaching around her ass, I push a finger into her backside, and she instantly comes again, squealing with delight.
I’m tiring, and drop to my knees on the thick carpet, where we make love, slow and sensual, her bottom writhing and dancing on my thighs, my mouth sucking on her pale, veined breasts. Even as this siren pleasures me most sweetly, I notice her eyes darting toward kaçak bahis the chair in the corner, checking that our audience is still captivated. I glance to see Annie’s hands moving energetically under her little black dress. I’m glad she’s enjoying herself.
Carolyn with a ‘y’ pushes me backward and lies astride me, kisses me sweetly, combing her fingers through my hair while she begs me to fill her with my ‘spunk’, as she calls it. Hugging her tightly, I gladly deliver myself into her sweet, schoolteacher cunt.
We are cuddling and cooing on the floor when Annie gets up and leaves the room.
“Is she going to pleasure herself now?” Carolyn asks
“Yes,” I reply, surprised. “How did you know?”
“I learned a lot a few years back when I had those two in my Special Ed sessions. Since they won’t let most people touch them, masturbation is their only release. The girl did it in class, until we found another outlet.”
“I’ll bet that made the day interesting.”
“You could say it was ‘touch-and-go’ for a while,” she grins. “How long have you been doing this? Giving Annie her personal live porn shows?”
I grin back. I’d never thought about it that way. “About twenty years,” I tell her. “She won’t let a man touch her, not even me.”
“What about her caretaker?”
“She can be quite difficult at times…”
“I’m sure,” Carolyn says, settling her lips around my nipple and sucking gently.
I shudder with a rush of goosebumps. “…anyway, we haven’t found anyone who could take it more than a few months.”
“So, who tends to her?”
“Mostly me. Steve helps. He’s our valet and driver. George cooks for us and Willy maintains the grounds, but they have houses of their own, and usually don’t interact with Annie.”
“So Annie is surrounded by men…” she observes quietly, pondering to herself, although I’m sure the thought was intended for my benefit. “No other women in the house, I presume.”
The impact of her simple statement rolls over me like a boulder. I am embarrassed to admit, “Not since Mother passed away. Annie was only twelve.”
And then there was Father, I recall, and I feel the angry blood rising in my face again.
Carolyn scoots downward and takes my whole limp, slimy cock into her mouth. “People are so hung up on stiff dicks, but I like them when they’re happy and contented, like this.” She rolls it around with her tongue, slurping noisily.
The feelings are delicious. I can tell it’s growing.
My little schoolteacher notices too. “Well, he’s waking up for round two,” she says, and sucks on my balls. My erection is immediately rejuvenated.
“How about another drink before we get under the covers,” she says, wiggling her brows.
“I have a delightful ’92 Batard-Montrachet that’s perfect for the occasion,” I tell her, slipping on my robe. “I’ll be back in two shakes.”
“Don’t shake it too much,” she says. “This pussy isn’t going anywhere until she’s had at least two more hot injections.”
This woman is incredible.
I return shortly with the rare vintage and two glasses. She’s not in the bedroom. I begin searching – not in the bath, not wandering the halls…
I hurry to her room, and my fears are real. The door is open and the lights are low. Annie is playing with herself, moaning and rocking her hips, with Carolyn next to her bed, watching. I am fuming. Carolyn’s hand is hanging in mid-air, several inches above Annie’s crotch. God, no! If she touches Annie, we’ll be up all night trying to calm her down. Furious, I’m about to unload my wrath when I notice that Annie is staring at Carolyn’s hovering hand. The middle finger of Carolyn’s hand is jerking, vibrating rapidly, as though twiddling an invisible clitoris. I step back into the dark hall, and watch.
A lump rises in my throat when Annie reaches up, grasps Carolyn’s wrist, and pulls that wiggling finger into her dark, puffy cunt. A shrill “Oh!” accompanies the first contact, but she holds Carolyn firmly against herself.
My eyes become blurred with tears. She’s touching Annie.
Carolyn keeps up the rhythm, and Annie writhes and squirms, frantically clutching at her small breasts. Carolyn turns her face up, sees me at the door, and grins. I’m frozen, motionless, afraid to disturb the magic of this moment. My heart feels about to burst; it’s the first time she has wanted anyone to touch her since…since him.
I watch the motion of Carolyn’s frenzied fingers, pleasuring my sister. Annie’s face is contorted, her eyes squeezed shut, and she is rocking her head back and forth, grunting emphatically between ragged breaths each time she thrusts her cunt against Carolyn’s hand. In seconds, Annie tenses and arches her back, draws in a sharp breath, then again. She is suspended above the mattress, her mouth open in a perfect circle, and with a weak, thin wail, she slowly settles onto the bed, limp, relaxed. Her lanky limbs are twisted in odd shapes. Except for the heaving of her conical breasts, I might think she is lifeless.
Carolyn gently strokes her swollen labia, and her legs and tummy, then Annie turns on her side, curling up. Carolyn pulls the covers over her. My sister is sated, for the moment. Is it my imagination, or did I see a glimmer of a smile?