Ms. Wittmore Pt. 02: Training Cally

Cally stands straight as she has been directed, her legs slightly apart, her ass tucked in and her breasts pushed out. It's not a position she would exactly call comfortable to stand in for long periods of time, due to the ridiculously high kneels she is standing in, but compared to some of the positions she has found herself in over the last three weeks its one of the easier ones.

She feels the blindfold that is covering her eyes being adjusted and the warm breath of Ms Wittmore against her skin. She twists her fingers together, locking them behind her back in order to arch her back that little bit more, in aid to perfect the stand.

"Very nice Cally," says Ms Wittmore as she walks slowly around the young woman stood before her.

She had been right to pick this one above the others, she was proving to be very delightful to work with, she must remember to reward Seb on this delicious find. What a waste this girl had been in that seedy backstreet club, no wonder the creepy Gus Angles had fought to hold on to her. But, as always what Ms Wittmore wants, Ms Wittmore gets and after a little gentle persuasion Gus had reluctantly agreed to let the sweet Cally go.

Now as Ms Wittmore admired Cally, stood naked, blindfolded in one of her favoured display poses, she couldn't help but run a perfectly manicured finger nail over her exposed nipple and delight in the way it hardened to her touch. Cally was finally getting the idea behind this pose, unlike the restrained ones they used in training, this was solely down to Cally to hold and control, no matter what came her way. Ms. Wittmore sighed to herself, it was such a temptation to keep her all for herself but if nothing else she was a smart business woman and she knew the potential stood in front of her.

At the feel of Ms. Wittmore's finger nail on her exposed nipple, mixed with her heightened senses caused by the blindfold covering her eyes, Cally fights the moan threatening to escape her lips. As Ms. Wittmore's finger nail continues to tease her nipple she feels herself becoming wet, the way she circles and drags her nail continuously sets all of Cally's senses on fire. She has always had sensitive nipples and breast play is a huge turn on for her, so it was taking all her energy for her not to move and break her pose to grab Ms. Wittmore's head to pull her tighter. When Ms. Wittmore takes her hard tip between her finger and thumb and lightly rolls it between them she couldn't help but bite her lower lip, as her body begins to tingle all over.

Cally couldn't help but react to even the lightest touch from this woman. The feelings that stirred inside her not only confused her but intrigued her, she had never been attracted to another woman and she wasn't even sure if attraction was the right word, but the more Ms. Wittmore touched her, the more she yearned to feel her touch. No matter how difficult the things asked of her seemed, she knew just one touch from this woman would have her yearning more and more and ready to anything simply to please her.

"Oh Cally, Cally, What have I said about biting that lip?" asks Ms. Wittmore. "As sexy as you look my dear, its not the reaction I want to see," she continues as she takes Cally's nipple between her finger and thumb and pinches hard, making Cally struggle not to squirm.

"Remember what I told you, suck in the pain, feel it wash over your body, embrace it fully!" She demands, squeezing, pinching and twisting Cally's now fully erect nipple. Knowing that behind the blindfold Cally's eyes are shut tight as she fights all the sensations shooting through her body right now, only makes Ms. Wittmore smile more. Releasing Cally's nipple, she steps away "OK lets begin..."

Behind her blindfold Cally hears Ms. Wittmore walk away across the room and the door opening. She arches her back just a little more, steadies herself and waits... And waits.

A seemingly long five minutes later the door reopens and Cally can hear heavy footsteps heading her way. As the person approaches she hears them let out a satisfactory sigh and then a finger is tucked under her chin, lifting her head higher. She feels a sudden wet contact on her neck as they lick along the large pulsing vein and then kiss her neck. A low moan confirms Cally's thoughts, in front of her is a man, no doubt one of Ms. Wittmore's more valued clients, given the privilege to aid Ms. Wittmore in her training. The mystery man continues to kiss and lick Cally's neck, slowly moving up to her jaw line and then across to her lips, where he stops for a millisecond before kissing her roughly. She can feel his lips pressed hard against hers and then the tip of his tongue as he forces it into her mouth, kissing her deeply.

Of all Cally has learnt in the last few weeks, learning she is expected to let clients kiss her is the one she has struggled with most, worse than that she is the fact she is expected to react and kiss them back, with as much passion and enthusiasm as she would any lover. The kiss is sloppy and wet, his tongue is exploring her mouth greedily, Cally entangles her own tongue with his.

His hands are now moving up her sides, not softly but clumsily and somewhat roughly, in a hurry to reach their goal, her pert, full breasts that are pushed out on full display. As his hands gripped her breasts in one movement, squeezing hard and lifting, he breaks the kiss and moves his lips to her nipples. Licking and sucking at each in turn, tugging hard on her fully erect, sensitive globes. She knew Ms. Wittmore would be somewhere watching, she had to keep her composure as long as possible. What was it Ms. Wittmore drummed into her time and time again, "We are about quality here Cally, not quality, our clients what the real experience, the real deal."

As he continues his onslaught oh her breasts, moving from one to the other Cally reaches breaking point. Moving her arms up around his neck, Cally arches her back more, pushing her body fully against his and is rewarded with a deep moan as his hands start to explore her back and he sucks her nipple deeper. Pushing her hips forwards and beginning a slow grind with her mound against his pelvis, she is again rewarded by more moans as he also starts to move his hips. She can feel his cock twitch inside his pants and begin to harden and grow as they rub against each other, her own pussy is wet and wanting making her grind a little harder.

Cally knows she has broken from the display pose too early and needs now to make up for that mistake in order not to feel the full wrath of Ms. Wittmore later. She lifts her arms and starts move her body as if dancing to music, he breaks contact from her nipples as she turns in his arms and leans her back against him. His fast hardening cock pushing against her ass cheeks. Pushing back she grinds on his cock, bending over and wriggling her ass, before slowly rocking herself back and forth so her ass bumps against his cock softly. Straightening her back once more, she turns in to face him again, wrapping her arms once more around his neck she leans and kisses him with full on passion, continuing to move her body against his.

His hands are back on her breasts, squeezing, lift and pushing them together before gripping both nipples between his fingers and thumbs and twisting hard. Cally just manages to stifle a moan escaping her lips as he moves his mouth to her hard, needy nipples, once more licking and sucking each in turn. She feels his sharp teeth bite down on her nipple and a soft moan finally escapes her lips before she can prevent it.

"Hmm that's what I like to hear, a girl that enjoys our play!" he declares, just as a sharp slap is delivered against her left breast and his lips reconnect to the right. As he squeezes one breast hard Cally feels his teeth again, as he bites down on her nipple, sending a million shooting shocks of pain and pleasure through her body.

Sensing how her body is reacting he continues licking, sucking, biting and stretching out her nipples over and over, occasionally delivering another hard slapping smack until her breasts begin to mark and redden. Pulling back as if to admire his own work, Cally is left standing for what feels to her an age, as he slowly moves around her, taking her in. Suddenly she craving more physical contact, missing the attention of his lips and hands on her body, she can feel how wet she has become, more confusing feelings for her to get her head around, as her body starts to scream its needs to her.

She can sense him stood behind her, daringly she steps back, making out she is just steadying herself and lets her hands press against the growing bulge contained within his pants.

"You like what you feel?" he asks as he thrusts his hips forwards.

"Yes sir," she replies as shyly as she can, giving his bulge a soft squeeze, causing him to moan out again.

Cally feels his hands on her shoulders, turning her and pushing her to her knees.

"Undo my pants and show me how much you like it!" he demands.

Quickly Cally reaches up and fumbles with his belt. Now getting impatient he knocks her hands away and undoes his own pants. Shoving them down to his knees, he grabs the back of her head and forces her forwards.

"Open wide, its feeding time," he hisses as he pulls her against his hard cock.

Doing as she is directed, Cally feels the head of his cock against her lips and then the stretch as he pulls her on to it. She is surprised how big it feels, still only semi hard but already stretching her lips wide, as he forces his rod deeper. She starts to move her head back and forth, sliding up and down his hardening shaft, pulling him almost all the way out her mouth sucking on his head, before taking it little deeper each time. As he becomes more excited he tightens his grip on the back of her head, twisting her hair into his fist, pushing and pulling her head to speed her movements and force her to take him deeper. His deep moans let Cally know he is turned on almost as much as his now fully hard, huge cock does throbbing deep in her throat, as he starts to move his hips, fucking her mouth.

Pre-cum is seeping from his head and his breathing is getting heavier, he is slamming his hips against Cally's face, his balls swinging and slapping her chin over and over, she knows he is getting close. Suddenly he pulls free, Cally can only guess he has grabbed his own cock and is jerking off in front of her and this confirmed when she hears a loud grunt and the first stream of his hot cum hits her face. Automatically she opens her mouth and pokes her tongue out to be rewarded with the second stream landing on her tongue, which quickly she swallows, awaiting the next stream and the next. Feeling his hot seed slide down and coat her throat as he cums hard, pumping every last drop onto her waiting tongue and over her face.

His hands are under Cally's elbows as he lifts her up back on her feet, moving a finger to her cheek, wiping away some of his own cum from her face, he kisses her lips softly.

"I taste good on your lips," he says quietly, almost shyly.

"Maybe you should taste more then Sir," she replies, returning his kiss, slipping her tongue between his lips and feeling them part and open so her tongue meets his.

"I would like that..." he almost whispers as their tongues begin to twist together in a slow passionate French kiss.

Suddenly feeling a strange shift in the dynamics between them Cally pulls away from the kiss and with renewed braveness reaches up and removes her blindfold. Blinking so her eyes adjust to the light she sees before her a man in maybe his late forty's, a little over weight but by no means not attractive. He is stood dead still now looking into her eyes, neither of them seem sure of the next move but a deep instinct tells Cally this is today real lesson.

"Can I ask you a question?" Cally asks.

"Sure.." He replies, looking a little uncomfortable suddenly.

"Are you some sort of sissy boy?" She asks, emphasizing the word 'Sissy'.

"W...hatttt," he stammers in reply, looking down at his feet, his face flushing which Cally is unsure is with embarrassment or anger. Suddenly there is awkward feeling in the air, Cally knows she has some quick fixing to do.

"No I'm not a sissy boy," he all but spits out.

"Sorry Sir, I didn't mean to offend you, I apologise if I have over steped the mark," she quickly replies, sounding as humble as she can.

"No it is fine, Your question caught me by surprise is all, but Ms. Wittmore warned me you are still in training, so lets forget you said anything," he replied smiling.

"Although to answer your question fully, I have a certain fetish that Ms. Wittmore helps me with," he quietly explains.

"And this fetish is...?" she asks a little taken aback.

Without another word, he Pulls her to him and starts to lick her face, clearing away all the remaining cum, "I like to taste cum, mine and on occasion other peoples."

The sensation of his warm tongue sends pleasurable shocks through her body, all the way down to her pussy which is now tingling wildly and soaking wet. His words are spinning around in Cally's head, as she comes to realise she is as turned on by this turn of events as he is. Slowly she takes his hand in hers and guides it between her legs, just has she had a few short weeks ago with Ms. Wittmore, parting her legs.

"Would you like to eat your own cum from here?" She asks forcing his hand with her own against her pussy.

"Yes Cally, I would very much like that," he replies letting her lead his hand as she starts to move them together over her pussy. Pushing down she begins to grind over his hand while her own pushes his firmer and moves faster.

Looking down she can see his cock is once again hard and now she can finally see the true size, it has to at least nine inches and thick in girth too. He sees her looking down and smiles, thrusting his hips forwards, pulling his hand free from hers and grabs her by the waist.

"You know..." he whispers as he pulls her to him, "Ms. Wittmore said I would enjoy you and she was so right." He continues as he spins her around and bends her over at the waist, kicking her legs apart.

"You are everything she said and more, even with your loose tongue and I am sure smart mouth, you will be very popular in the weeks to come and I am deeply honoured to be the first to truly enjoy you," he exclaims as he shoves his huge hard cock deep in her soaking wet pussy.

Cally feels her whole pussy stretched beyond it limit as he thrusts deep, the immense pain is sharp and she screams out, any doubts on who was in control that may of entered her head were completely lost. She can't remember ever feeling this stretched opened, his cock feels huge and the initial pain of him forcing himself in her lasts longer than imaginable, not that he seems to care.

He slams her over and over, fucking her hard and fast, she was thankfully soaking wet and that made it easier to enter her, not that he really cared, all that mattered was to fuck her until he came, He was known to be a selfish lover, all his girlfriends said so, but here with one of Ms. Wittmore's girls and a trainee in particular none of that was important, she was here to pleasure him and so far Cally was very pleasurable.

Finally a deep pleasure began to take over Cally. Her pussy was stretched wide open and she could feel her juices running freely, she pushed back to meet his thrusts moaning loudly. Ms. Wittmore had taught her that most men like to hear a woman, to hear they are enjoying it, no matter how they are being fucked. The only difference was Cally was starting to enjoying it, more and more, she moaned loudly and thrusts back harder still.

As her orgasm builds she can feel his cock throbbing deep in her, with each thrust he grinds his hips hard against her ass, his balls slap against her thighs. His fingers are digging in her hips, forcing her back even harder as if he can sense her about to cum, he is grunting heavily with the effort of slamming her over and over, she can feel small beads of sweat that must be from his forehead start to drip on her back. Her knees feel weak, she leans forwards more and her almost loses her balance, but he has her hold tight, keeping her up, keeping her in position as he continues to fuck her harder and harder. Every part of her body seems to be on fire and when finally her orgasm hits her, a strong leg shaking full body orgasm that rips through her body from tip to toe, she can't help but scream out loudly.

Cally orgasms and her pussy grips his pulsing cock, milking him with a strength he has never felt before, he suddenly wants to fuck her more. Push her further over the edge but his own orgasm is building fast and the need to shoot his load in that tight pussy is overwhelming. As he starts to think of his hot creamy seed coating her walls and filling her it becomes impossible not to cum, he starts to buck his hips, grind deep and hard against her ass as he imagines her cum filled dripping pussy hovering over his needy tongue and mouth. With a final thrust he explodes inside her, pumping his seed deep, continuing to pump to make sure she receives every last drop possible.

His orgasm meets Cally's in strength, she feels his cock throb and tighten inside her and then the final thrust as his hot cum shoots inside her spasming pussy. With each thrust comes more of his seed, shooting deep and filling her full, she can feel another orgasm building strong and fast and can only hope he can sense it within her. But he doesn't or he doesn't want to as quickly he pulls out, leaving Cally wanting and with a strong emptiness feeling. He stands her up and walks to the nearby sofa, pushing her down onto it. Bending down he grabs her legs, spreading them wide and lifting them over his shoulders.

Cally watches as he just sits back on his knees staring almost transfixed between her legs.

"Oh fuck!" he declares as Cally gives a slight push and his cum starts to drip out of her still partially opened pussy. "Don't waste it," he all but begs, moving his head quickly between her legs.

"You better lick it all up fast," she says pushing once more, letting another dribble of his thick creaminess flow from herself. Without another word he starts to lick her pussy, scooping his own cum with his tongue and swallowing it down. Looking down in amazement Cally watches the way he laps at the creamy mess that is a mix of his and hers orgasm, he face is covered in juices and he is moaning loudly.

"Someone is hungry?" she teasingly asks, wiggling her hips and allowing more to flow free onto his waiting tongue.

He doesn't reply but his licking intensifies and he moves his lips to cover her entrance, sucking deeply, his tongue probes deep, between licking and sucking, making sure he reaches every last drop. Cally can feel her own wetness intensify and the build of another orgasm deep within her, a much needed orgasm. Somehow she knows it may never come if she doesn't force the issue, so she reaches up and pulls his head deeper, starting to grind her hips against his face. He is content with his own licking and tasting that he pays little attention at first as she starts to grind harder, then he grips her hips to steady her and pin her where he wants her, so she reaches down and starts to rub her clit. Between his licks and sucks and her firm rub on her clit it doesn't take long before she is bucking her hips and starting to cum, squirting into his waiting mouth.

Watching him drink her cum with the final traces of his own cum makes her orgasm intensify and she cums harder and longer than she can remember doing so before. They are both fully spent and as Cally slumps back into the sofa, he lifts himself up and all but collapses on top of her. Without even thinking about it, Cally wraps her arms around him and kisses him deeply and passionately and he responses fully, his body crushed against her.