The Naughty Assistant: A Novel of Erotic Punishment – ebook



The Naughty Assistant by Imelda Stark

Alyssa wants ever so much to please those she serves.  And indeed, her blonde beauty and warm, helpful attitude has always charmed all who know her. As does her intelligence and formidable competence in her role as a high-end executive assistant. But ever since girlhood she has been possessed of an inner imp of rebellion that causes her to almost routinely sabotage meeting the expectations of those in charge of her.

As a child, this phenomenon resulted in frequent trips over her parents’ and teachers’ laps where her skirt would be raised and panties lowered for long painful conversations with her squirming buttocks.  Once grown, she has gravitated towards bosses who continue this tradition, though imbuing it with an erotic component that our heroine finds quite compelling.

Her punishments take different forms with her first boss Laetitia, a gorgeous widow who delights in punishing miscreant derrieres, and her ultimate boss Abraham.  On Abraham’s Hawaiian compound Alyssa joins a bevy of beautiful submissive women all of whom share her addiction to painful pleasures.  A copious variety of scenes ensue in which the naked bodies of the denizens are subjected to ingenious torments and erotic delights in equal measure.

The Naughty Assistant includes lots of spanking, anal play, breast and pussy punishment, femdom, maledom, with lots of femsub, and a little malesub. Fans of Imelda Stark will find another arousing tale to kindle their spanking fantasies.

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Excerpt from ‘The Naughty Assistant’



The handsome Master had shed his Speedo and was comfortably nude, his cock already fully erect again after watching the unveiling of Alyssa’s perfect ass and her promising orgasm. He was not as annealed to getting his subs off as Laetitia, but was also not averse to their pleasure, especially if it augmented his own. Thus, Abraham’s preference when sodomizing one of the women whom he enjoyed topping was to get her off while fucking her always well-spanked ass. He found that the delicious spasms of the pelvic floor of a responsive female were just the additional aliquot of pleasurable stimulation to enable him to climax most satisfactorily. Which he seemed to need to do at least half a dozen times a day.

A libido this powerful was unlikely to be slaked by a single partner. As a result, Abraham discretely prospected via his BDSM connections (such as Laetitia) for beautiful women who could serve multiple roles in his high-profile life. His House Manager Althea was one example, a bisexual switch who was quite equally happy to give or receive painful pleasures to males or females. Likewise, his cook and gardener were quite lovely women who were exclusively submissive and happy to receive daily spankings and fuckings from either their employer or his imperious house manager. The pilot of the Gulfstream was an exception, a male who sympathetically locked the cockpit door and kept his own counsel regarding his very generous employer’s rather outré tastes in in-flight entertainment, especially abetted by the gorgeous Malaysian cabin attendant. As with all of his female entourage, she did multiple duty as an excellent mid-air cook, impeccable server, and willing participant in the naughty erotic activities their employer enjoyed.  Her name was Anidanita, and she took genuine pleasure in taking part as an assistant in Abraham’s depredations of his female companions. She found even more joy in offering up her own perfect tidy rear end and small, sweet firm breasts to serve as the main course, as it were. All of these women lived in the servants quarters on the compound, where Alyssa would be assigned a room as well. Their employer liked his female entourage at hand 24/7, whether he needed them for professional or personal duties. And he paid so ludicrously generously and provided them with such a lavish lifestyle that the turnover rate was far less than one employee per year.

But at this moment, our Alyssa had not yet realized she was to be joining a submissive sisterhood under the auspices of the overwhelmingly handsome naked man about to spank her obscenely extended and delicately parted buttocks. She just knew that she was exactly where she wanted to be on the entire planet at that moment. That was with her most vulnerable parts offered freely up for the enjoyment of dominants whom she found breathtakingly attractive. This was her sweet spot, with what she hoped was going to be just the right touch of fiery spice to enhance her ultimate physical and psychological pleasure. Our heroine only hoped that the lovely black house manager’s hold on her hips would help her to hold position for whatever Abraham had in mind for her, so she would be pleasing to him.

She felt the dom’s hand rest lightly on the small of her back, directly between Althea’s firmer grip on the inward flare of her hips toward her slender waist. This all felt somehow reassuring to Alyssa, as though her soon-to-be assaulted nether cheeks were safely contained in order to accept their fate. And then that doom was commenced, as the large room resounded with the crack of her first spank. This was delivered with shocking force by the full swing of Abraham’s powerful right arm connecting to the center of her left buttock. That appendage had not known such contact in many months, and its owner yelped at the sudden pain that she knew so well by history but had forgotten in recent experience. The spanking proceeded briskly, as the dom cheerfully whaled away on the dancing, clenching moons that rapidly darkened in color from their original ivory towards a nice medium cerise. He and his house manager commented conversationally about how charmingly his targets wiggled as they struggled to accommodate their plight, and how bravely their weeping owner bore her well-deserved punishment. This continued until Althea had counted out a hundred spanks to each buttock, at which point her Master declared himself quite satisfied with Alyssa’s first spanking in her new job.

His own arousal had peaked rather powerfully during his favorite erotic aperitif, and Althea reached into a drawer beneath the coffee table next to them to withdraw a tube of lubricant. The clearly excited black house manager looked expectantly at her Master and inquired: ‘May I prepare you to enjoy the rest of her bottom, Sir?’ Abraham nodded, and sighed in pleasure as a generous dab of KY was worked into his phallus, whose veins gleamed in the morning sunlight through the wide apertures in the walls of the great room. Then his able aide guided his cock against Alyssa’s bottom hole, as she remarked: ‘My goodness, Master, look at how wet and swollen her little blonde flower has become while she was getting spanked! I think we have a genuine submissive on our hands, here, a biddable little pain slut just as Mistress Laetitia promised us.’

Our heroine moaned both in excitement and mortification as her most intimate responses were described (and manipulated) so matter-of-factly by the dominant duo participating so cheerfully in her ravishment. And these feelings only deepened as Abraham replied as he began to press his enormous cock home in her too-long-unfucked back passage: ‘I’ll be wanting you to get her off as I usually prefer while I’m sodomizing her, Mrs. D. Let me plow her sweet little rear furrow for a while just to get a feel for it, and then you can start playing with that luscious little golden cunt. We’ll see if she fancies having that perfect ass fucked as much as she seemed to enjoy having it spanked!’

Then the dom held tight to the perfectly gorgeous, inflamed buttocks he had just so enjoyed belaboring with his hard right palm.  He drove his cock slowly but inexorably between them as their owner let forth a rising shout of pure pleasure. And in fact, as his cool thighs settled against the burning moons when she was impaled to the hilt, her cries immediately morphed into those of orgasm. Abraham was stunned by this development, having never experienced a submissive so deeply entrained that she climaxed from anal penetration alone. He had heard of, and fantasized about, such women. But in his own experience clitoral and/or G spot stimulation was always required to get his partners off the way he preferred in order to stimulate his own orgasm in their back passages. He was thrilled at this turn of events, and even more convinced that he had a true find on his hand in lovely Alyssa.

Her new employer then proceeded to give our heroine the ass-fucking of her life, driving in and out of her for over half an hour with his enormous cock as she stopped counting orgasms after half a dozen. At last, Althea provided him addition stimulation by caressing his balls in one hand as she finger fucked his prostate with the other.  Abraham finally roared his pleasure as he discharged great gouts of semen into Alyssa’s welcoming back passage. He collapsed over her naked form, their sweaty bodies clinging together from the waist down. Her bunched dress absorbed the perspiration from his chest while their racing breaths and heart rates gradually calmed. The serene house manager stroked both of their naked bottoms, murmuring: ‘Such a pretty pair you make…’

At last, the naked entrepreneur stood up and withdrew his cock from its delicious encasement. Alyssa moaned in mild protest against the removal of the organ that had so deliciously filled her for the past delirious infinity of submissive transport. He then announced: ‘Enough dallying, ladies, we have two more much more severe spankings to deliver before our naughty new employee’s admission interview draws to its close. Though I want to reassure her that so far her performance has left me with little doubt as to her suitability for the job. Mrs. D., I have some thoughts about how things should go from here, if you would allow me to pre-empt your right to punish her in your own independently chosen manner for her lustful glance at your lovely backside as you were leaving to fetch our tea?’

The bent blonde moaned at the declaration that more painful attentions to her most vulnerable erotic parts were in store. At the same time as her pussy gushed anew with its own rather more enthusiastic opinion about the desirability of such proceedings. The regal black woman who had recently held Alyssa’s ass in place to receive its first dose of such attentions replied.  ‘Why, dear Sir, I would be delighted to be guided by your thinking, since your ideas about such matters are always wickedly creative…’

Their Master smiled and then went on: ‘Excellent. I think we will begin with her using her hands and mouth to worship the very same part of you she violated with her slutty eyes, while I relax a bit and enjoy the view. Of course, my visual pleasure would be greatly enhanced if no clothing intervened. So let’s get both of you naked before we set our naughty applicant to work in the beginning of her atonement for her licentious ways.’ The young blonde was helped to her feet, and her summer dress and brassiere were quickly discarded to reveal her well-toned beauty in all its glory. Then the taller and older house manager likewise shucked her own sheer coffee colored dress to reveal that she had eschewed underwear. Alyssa had guessed this from the absence of panty lines in the clinging sheath Althea had worn since her arrival.

The body revealed by the black beauty’s removal of her single article of clothing was a visual delight to both Alyssa and Abraham. The house manager was nearly six feet tall, barely shorter than her employer, and had long clean limbs with a uniform cafe-au-lait coloration over her entire body. Her jet black very curly hair was worn clipped short, revealing the sculptural perfection of her head and long neck. Her underarms seemed naturally hairless, and her small barely B-cup breasts were so firm that a bra was unnecessary to hold them perkily in place against gravity’s pull. Their prominent black aureoles and nipples were fiercely erect above her flat and sculpted abdomen whose muscles defined just as perfect a six-pack as the blonde assistant’s rigorously toned belly. The one part of Althea that had any visible fat at all was her bottom, which was blatantly feminine though still quite firm and athletically muscled from her high school career as a sprinter. Her tightly curled black pubes were trimmed quite short, displaying labia that were nearly black on the outside and a shocking pink within, especially given their engorged and glistening state. She took an ironic pirouette before Alyssa’s eyes once naked, as if to say: ‘Get as good a look as you like now, since you are about to pay dearly for your lustful gaze, young woman.’

Abraham took over, as was his wont: ‘Aren’t the two of you as lovely a contrasting matched set as I could imagine! Mrs. D., let’s have you spread your legs wide and bend over to grasp the end of the couch so I can watch those lovely little titties I so enjoyed spanking this morning dangle. Since I do love the way they wobble when you are writhing in pleasure or pain. Then our naughty applicant can kneel behind you and worship that gorgeous ass of yours, perhaps the most spankable one I ever get to play with. It will still be quite swollen from how cruel I was to it last night, so she can begin by giving your buttocks a careful tongue bath while she gets you off with her fingers. Then I think she should give a nice long tongue fucking to the secret little rosette between them. The poor thing is probably still a bit sore from how much my cock enjoyed it both last night and this morning. That way she can feel how delightfully it tightens when she gets you off a second time. And then we will get her up to receive a far less gentle series of attentions to the very same parts of herself, lucky girl!’

Now Alyssa was far from a novice at paying loving oral and manual attention to the backside of a Mistress. After all, Laetitia had reveled in the irony of receiving such diametrically opposite stimulus to the parts of her that she so enjoyed tormenting on our heroine’s body. But as the fervently submissive blonde settled in to deliver what was requested, she was surprised at how swollen the buttock flesh of the tall black woman was. This was a new experience for her, and she wondered if her own backside was going to be as tender and inflamed as the house manager’s gorgeous robustly round nether cheeks. Apparently, their Master had few compunctions about the state in which his pleasures left the places he so enjoyed punishing. This was hardly surprising, given how he had behaved thus far. But of course it was totally arousing to the penitent assistant,

Because of how inflamed Althea’s poor buttocks were, Alyssa was extra careful to lave them with utmost gentleness with her broadened tongue. The happy domme moaned in pleasure at the sensation, and even more strongly when the blonde assistant’s fingers spread the house manager’s nether lips and, after gathering the liquid evidence of her arousal, used it to encircle her clitoris very languorously. Then the penitent applicant’s other hand followed the pathway it knew from years of pleasing a demanding Mistress to enter the black woman’s welcoming vagina and begin massaging its G spot.

Abraham watched with great interest, his indefatigable cock already quite erect again as he took in the ultimately sexy tableaux of the two gorgeous naked women making Sapphic love. He was even more pleased with Alyssa’s body with all of her clothing removed, as her perfectly formed C-cup breasts were eerily firm, a state he had only seen in women with surgical implants. The thought that he was to have carte blanche to enjoy them in his own special ways excited him greatly. Since self-restraint was far from his strong suit, he pulled the ottoman on which the gorgeous blonde had taken her first spanking and ass-fucking beside the two women. His hands reached out to fondle Alyssa’s tits, eliciting a muffled moan from her busy mouth which had by this time completely moistened Althea’s well-spanked ass. Which was now blessedly cooling as the saliva evaporated in the warm Hawaiian breeze.

Less than five minutes of mutual enjoyment transpired when Althea’s spectacular hips began gyrating wildly as her voice ululated in a rising rhythmic shriek: ‘Oh… My…  God… Yesssss!’ And she came quite enthusiastically for the better part of half a minute before sighing as her pleasurable spasms waned. Abraham gave Alyssa’s nipples an appreciative pinch and intoned: ‘Now get that talented mouth that took such nice care of my cock to work in Mrs. D.’s nether cleavage, naughty girl. And keep those fingers working in her saucy little pink cunt, since she comes again without even needing a respite. When she does, I want that tongue of yours buried as deep as possible where the sun don’t shine, if you take my meaning!’

This also was quite familiar territory for our heroine, whose last Mistress had very much fancied at least one orgasm a day with her loyal assistant’s tongue fucking her own nether orifice. Both seemed to glory in the symbolism of this ultimately submissive series of acts. The one in which the most intelligent, articulate orifice of a willing slave lavishes ultimate tenderness on the most fundamental, so to say, portal of the person who has visited punishment and fierce violation to the very same vicinity and passage of the supplicant. And now, with Althea, the additional fillip of a blonde, white girl worshipping the ass of a stately black woman old enough to be her mother added another piquant layer of complexity for all involved. The house manager sighed with pleasure as Alyssa’s warm tongue worked its way down her deep nether cleavage, whose depths were extra sensitive due to their usual protection by her large muscular buttocks.

At last the already devoted applicant hit pay dirt, so to say, first rimming and then tongue fucking Mrs. Davidson’s well-scrubbed back passage. All house members were required to receive a thorough enema each morning to render that part of themselves pleasantly accessible to Abraham at all times. Because of both inclination and selection bias, all of the entrepreneur’s submissive women were anally eroticized to start with. And then they all experienced daily reinforcement of such tendencies. Since their Master had his own need to feel the delightful orgasmic contractions of their pelvic floors around his invading organ in order to have the quality of climaxes he preferred. The result was that Althea was primed to climax hard and often as soon as Alyssa’s tongue entered her anus. At least three rollicking orgasms ensued before the dom pronounced himself satisfied and the naughty assistant’s promised spankings could proceed.

By this point, our heroine was in an erotic fever herself. The combination of worshipping Althea’s gorgeous feminine behind with having her breasts and pussy skillfully fondled and teased by Abraham’s knowing hands for the past half hour had brought her arousal to a fevered pitch. The dom stood up, his own cock evidencing his interest in the luscious blonde body he had been toying with as its owner serviced his beloved house manager. Since his interest in restraint did not extend to himself, he decided to take advantage of the sweet blonde cunt he had been teasingly fingering and went to his knees on the soft carpet as he growled: ‘You two hold still while I do a little fucking here…’

The handsome entrepreneur guided his phallus to Alyssa’s slit. He rubbed its head up and down to collect the copious secretions before driving inside as our heroine shouted with the pure pleasure of being fucked there after such a long tantalization. She instinctively dropped her own head down from Althea’s anus to the black woman’s steamy pussy, which was soon engulfed by the applicant’s skillful mouth. And then the three of them floated on a delicious cloud of erotic delight. The two women came loudly several times each before their randy employer spent his passion inside the perfectly tight and hot confines of his naughty new assistant’s vagina for the very first time.

After they had all calmed down a bit, he sighed and remarked: ‘Such a naughty, disobedient little potential assistant we seem to have here…if she wasn’t such a wonderful fuck, I’d probably fire her on the spot for not following orders!’ Alyssa felt panicked and gabbled: ‘I’m so sorry, Master, I didn’t mean not to obey…in fact, I honestly don’t know what I did wrong!’

Abraham sighed again, even more theatrically, falling into a game he played several times each day as he dolorously and always quite vociferously complained about his arduous task in disciplining such unruly employees. Then he went on: ‘And now we have to add not listening to failure to follow orders, and her poor buttocks look to be in for yet another pair of spankings! I wonder if she will ever again sit down at all, given how sore they are bound to be when I am through with them. And of course, she has involved Mrs. D. in her perfidy, since I ordered both of you to be still while I fucked Alyssa’s saucy little cunt. And you both seem to have managed to come rather raucously at least three times apiece while I was about my business!’


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