The Helldesk Ch. 03

As Carlo headed back our way with our drinks, I settled back in my seat, fascinated to see how things would develop.

As Carlo arrived and placed first the Negroni on her coaster and then my P.O.F on mine, Emma leaned forward, sticking her chest out slightly. She raised the straw to her lips and her brows knit together, as if in concentration. As the dark liquid was sucked up the straw and past those full, pursed lips, her eyebrows shot upwards in surprise, and she simpered, "Ohhhh... bitter! But dark... and kinda like licorice..." As she released the straw, she tilted the glass slightly, and a couple of drops of condensation dripped from the base, right onto her out-thrust and perfectly positioned chest. She inhaled sharply, and raised one hand to cover her lips in mock surprise before lowering it again to carefully wipe the droplets away. Several times. In fact her hand was still massaging her breast in a way that was so gratuitously obvious that I could have pulled my phone out by now and taken a snapshot if I had so desired. She looked up at Carlo and smiled sweetly, "Very tasty Sir, thank you!"

"My thoughts exactly, Signorina!" Carlo's pause before he wrenched his eyes back up to her face was palpable, and he grinned before turning to me. "And what about food Sir? Have you had a chance to look at the menu yet?"

Wow! I had to hand it to the broad, she got full marks for artistic impression. She had more than fulfilled the terms of my demands, but she still had to do it twice more before he walked away. I turned back to Carlo, shook my head, and asked him what they had in the way of specials tonight.

"Ahhh, just a couple of them tonight Sir." As he pulled a small pad from his back pocket, the little tart leaned forward expectantly until she was resting her boobs on her forearms which lay crossed on the edge of the table.

I had no intention of going down without a fight, and dropped my hand into her lap, my fingers coming straight into contact with her now noticeably wet lips. So... she was enjoying this more than I had thought! I started to rub my fingers up and down the sides of her outer lips, squeezing and massaging, and generally being as much of a tease as possible. I mixed running my fingers down the outsides of her quim, squeezing the lips together as I went, with tight fast circles over her clit, and then one finger trailing slowly down the wetness of her inner channel, pausing to press gently against the tightly clenched opening of her cunt. She shifted slightly, spreading her legs a little further apart, and I moved my fingers back up to focus slowly on the hard little point at the top of her lips. Three fingers rubbing in fast tight little circles, pressed up hard against her clit would make it a little more challenging for her.

The way she was breathing had Carlo well and truly distracted. He was currently flipping pages of the pad automatically, his eyes nowhere near the paper. Emma clenched her thighs together, squeezing down on my fingers, making access a little more difficult. As he finally looked back at the pad, I forced her legs apart and slid all three fingers down, spreading her folds wide. I could feel that she was really getting turned on now. As I glanced back up from where I was able to see one firmly toned thigh and the edge of my fingers, she reached up and scratched the side of her breast, causing the flesh to wobble in an extremely distracting manner. Carlo's eyes flicked from the pad to her boobs, his self-control no stronger this time as he inhaled, ready to recite the specials.

I had no intention of letting her get away with anything this evening, so I wasn't going to count the way she had rested her breasts on her arms as one of the three touches,. However, the side-boob scratch was beyond reproach. It had gone on for about four or five seconds, and he still hadn't stopped looking at her breasts yet.

"So... tonight... our specials are..." he said, and his eyes finally strayed back to the pad in his hand. "Gnocchi Caprese, with a very understated but flavorful sauce; our ever popular Ravioli di Zucca, which is butternut squash ravioli in a sage butter and parmesan sauce; and finally we have Veal Picatta which is sauteed in lemon, butter, capers, and artichokes and is finished with a white wine sauce."

As my fingers continued to churn her butter, the slut continued to smile sweetly at Carlo, who in turn was still facing the table, watching her intently. There was no way she could sit back with my fingers working her quim, and from the clenching and unclenching of her stomach and inner muscles where I could feel them under my wrist, I could tell she was getting close to erupting like a volcano.

Her eyes dropped back to the menu which lay partially obscured by bother her folded arms and the breasts she had so artfully laid on top of them. She removed one arm to slide the menu further up the table, and 'unconsciously' cupped the other breast with the back of her forearm as if studying something on the page in front of her. In a voice that was clipped, and laced with iron control she said, "Ummm, the... Chicken Scarpariello....?"

"Yes, Signorina?" Carlo smiled sweetly back at her. He was obviously playing dumb, and I wondered whether he could see the constant movement of the muscles in my forearm as I continued to make life as difficult for the wench as possible. I was definitely starting to feel the burn though, so I moved back to sliding all five fingers first down and then back up her lips, the middle finger sandwiched in her inner wetness, the outer four between her outer lips and toned thighs.

A slight shiver betrayed the effect my change in tactics was having, but the reduction in the level of assault on her lady parts meant that when she spoke again, her voice was very slightly less strained, "Ummm, does that have peppers in it?"

Carlo grinned wolfishly and glanced at me when he said, "Yes, Signorina Emma, cherry peppers, I believe it says as much on the menu."

I couldn't help myself as my mouth quirked up into a smirk and I winked at him. He smiled a little more broadly and we both turned back to the poor unfortunate beetroot who was blushing furiously next to me. "Oh, silly me, I must have been looking at the wrong line," she said in a small voice.

"Of course, Signorina, there is a lot going on here this evening, so it's quite normal to be... distracted."

Ohhh, Carlo! How I loved him so. He was the perfect addition to the evening, and was playing his part to perfection. I was pretty sure that Emma knew that he knew what I was doing to her pussy, but I doubted she had any idea as to just how complicit he was in her humiliation. I was enjoying the whole exchange massively, and had no intention of interrupting things quite yet.

"So did the Signorina make a decision, or is she still too distracted?" he inquired solicitously after she continued to look at the menu and I continued to massage her lips. I slid once again down the length of her well lubricated cleft, and paused over the tightly clenched hole at the bottom. Her legs pressed together a little more tightly, and one hand came back as if to clasp her belly, but actually came to rest on the top of my wrist. As her fingers clamped down, I pushed the tip of my finger past her resistance and slid into her velvety wet darkness.

A small gasp slipped past her lips which she tried her best to disguise as a question, "ohhhhummm, howww about the Chicken Parmigiano, is it good?" She was floundering now, and Carlo tightened the noose of her embarrassment a little further.

"Oh but of course, Signora, everything here is good, we wouldn't serve it otherwise."

Ouch! That lack of attention had just got her demoted from an attractive young Signorina to a dusty old Signora. I slowly extracted the tip of my finger from her hole, and immediately pressed it back up against the tight barrier that had just squeezed it out.

Her recovery was smoother than her faux pas as she asked, "What I should have said was, is it better than the other dishes, relatively speaking? I've heard nothing but good things about your restaurant, so I have, errrm, high expectations."

Carlo raised an eyebrow. "Well, I'm very glad to hear that we've been so well spoken of Signorina, I just hope we can meet your very lofty expectations."

Oh snap! The implied snob factor that he'd thrown her way, was hardly mitigated by her promotion back to Signorina status. I continued to tease her unmercifully as I slowly pressed into her pussy, and then let the tightness squeeze me back out again. Her fingers tightened around my wrist, and I wondered what would happen if I made her come at the table... in front of Carlo. I wasn't sure she would be able to stay quiet enough to keep her climax between the three of us though, so I slackened off my pace, pushing my finger all the way in, up to the second joint, and left it there.

Instead Carlo turned to me and asked, "And you Sir, what will you have?"

"Oh, I'll have the youuuu...." I was just a heartbeat away from saying 'the usual', which would totally have given the game away and spoilt all the hard work I done so far. "Errrm, the ravioli di Zucca... was it?"

"Ahhh, yes, our most popular dish. I know Sir is going to enjoy it immensely!"

Fucker! Carlo totally knew what I had been about to say, and was probably enjoying my slip almost as much as he was enjoying Emma's discomfort.

Before he could stick the knife in any further, she said, "Oh, I'll have the same then please!" and dropped her eyes back to the table.

"Very good. Sir... Signorina". And with that he gathered our menus and strode away to put our order into the system.

"Holy fucksticks! What were you thinking... Errr.... Sir?!?" came the indignant gasp as I turned towards my date. "You almost made me come... at the table... in front of that guy!"

"And....?" I asked, not quite able to help it as one eyebrow raised itself lazily towards the maze of air conditioning ducts and other ceiling ornamentation that occupied the top half of the room. Are you going to try and tell me you weren't getting turned on?"

"That's not the point! He was right there!" Her embarrassment seemed to be an issue to her, something I vowed I would do my utmost to work on.

"Hmmm, well I don't think you need to worry about our host. I'm more concerned with whether you're having a good time. I was impressed by the way you managed to meet my requirements for touching yourself in front of him. You didn't seem to have any issues with the way you so gratuitously mopped up the water droplets for him, so why would you object to him knowing I was fingering your twat?"

Her nose screwed up, and she colored a little as her eyes dropped to the surface of the table. She was pretty cute when she got embarrassed. Maybe I shouldn't eradicate that quite yet. "Because... I errr.... might not have been able to keep quiet. Like, I said, I can't lose my job, and I wouldn't want to get arrested, so something subtle like the water droplets is one thing, but having an all out orgasm at the table, wearing nothing but a dress and a fucking butt plug? Where I might get arrested? That's a completely different matter."

I smiled as I asked, "Ohhh, yes, your little sapphire ring piece, how is that feeling?"

"Fuck you! Sir. It makes me twice as fucking turned on when I clench down as I get close to orgasm."

I smiled at seeing the feistier side of her character showing through. She might have caved to my blackmailing, but I seemed I hadn't broken her spirit. As I mentioned previously, I'm not a fan of doormats, apart from the literal ones that sit in front of your door. An unquestioning, unresisting, totally compliant doll can be bought online for far less money and effort than you would have to expend on its living, breathing counterpart. A little spark and spirit made things much more enlivening and also provided a better way of identifying punishable offences without it being a totally whimsical process on my part. That framework made it much easier for her to know when she was about to transgress, and hence when punishment might be forthcoming, especially if I was the one driving her into that decision.

"Mouthy little slut aren't you? Rather ungrateful given my efforts at hospitality and showing you a good time..." I grinned.

"Hospitality?! You said I was going to be paying for this dinner - how is that hospitality on your part?"

Her indignation had her turned slightly towards me, the impact of her lowered decolletage and noticeable nipples exacerbated by the way she was breathing. The twist in her torso meant that I had the perfect view right down between her legs to where my fingers had now slipped out of her hole due to the angle being all wrong. I reversed my fingers and flicked her clit like your average school bully would do to an unprotected ear.

Her gasp and the way she jumped as if I'd broken out the jumper cables I'd threatened her with earlier was such a gratifying reaction. I continued my attack, using it to punctuate my words, "Money... isn't... everything... little... slut... now... is... it?" I stroked my coiled and ready-to-be-released middle finger over her rock hard bud.

"Noooo! No Sir! huhhhh, fuck... that's fucking intense... Sir.... I think I preferred the earlier circles to that. They were torture in a good way, this is torture in a bad way."

I grinned as she continued to feed me useful tidbits as to what she liked, and what she didn't. I would have to file that away for later use.

"Well, we are here to make sure you have a good time, if I remember correctly?" I flicked her one final time for emphasis and she flinched again in a way that was starting to provoke a reaction. I pulled her hand over into my lap and pressed it up against my tumescent rod. She squeezed down, just a little too hard and I shifted uncomfortably in my seat. "Careful slut..."

Her pressure lessened and she started to stroke the length of my cock as it unfurled and swelled under her touch. I sipped at my drink and sank back against the banquette, looking out over the tables in front of us as her nimble fingers continued to bring me fully erect. The restaurant was now about half full, with only the booth next to us and two of the tables on the dais being occupied. None of those people were giving us a second glance, although the Bluehair who we'd scandalized earlier kept glancing our way every now and then.

The little tart's fingers were now running the length of my cock, pausing to rub gently on the underside of the glans where it pointed straight up my stomach, before gliding down it's full length to cup and gently massage my balls. Fuck! She was pretty good at this. The smouldering eye contact she was giving me as I turned away from the restaurant only served to amplify things. There was no way I was going to let her make me cum though, not like this, and not now. Not that I was quite in danger of that, yet.

"So how did you get to be so good at pleasing a man?" I asked as she continued to work me up and down.

She leaned in a little closer so that her breast was brushing against my arm, her lips a mere inch from my ear and proceeded to whisper her story in a breathy, cock-teasing way.

"Well... Sir... contrary to your very predictable assumptions, I've had plenty of experience as a submissive before this. Having grown up in a fairly strict and traditional household, I received the odd spanking with a hairbrush as a little girl, and it always left me trembling and shaky. Not out of fear, but for some other reason I wasn't able to identify at that age. When I started to have my first sexual fumblings with inexperienced boyfriends, they didn't really get me excited, and I couldn't help feeling that something was missing. So I didn't really date anyone through high school or college.

"Then, one night when I was in my early twenties, I went out with a pack of girlfriends and ended up coming home with a much older man, at least fifteen years my senior. He told me he was going to show me things I hadn't seen before, and that I probably wouldn't be the same again afterwards. He didn't force me at all, just told me that either I did what he asked or that he would leave. He agreed that it was a little unfair, but that those were the terms of what he was offering.

"The idea of not getting to find out what he could do was too tempting to resist, and when combined with the drinks I had enjoyed that night meant that when he told me I was to slowly strip in front of him, to put on a floor show for him, and to try and tempt him into going further with me, I was more excited and wetter than I could ever remember, and gladly obliged him.

"He seemed to enjoy the rather amateurish striptease and lapdance I gave him, and then told me that the next step was going to be having my hands tied behind my back, so that I was presented to him in a more pleasing manner. With that done, he proceeded to touch me and to tease my body, getting me worked up into a sexual frenzy that left me pleading for him to fuck me. He just grinned at that.

"Every step was a choice. He told me what the terms were and asked me if I wanted to continue. When he asked me if I'd ever been spanked before, I had a sudden flashback to the hairbrushes of my youth. Those recollections fired a heat in my belly that left me panting and caused me to look up into his eyes and beg him to spank me. He was happy to oblige.

He had large, strong hands and knew exactly what he was doing, and gave me an orgasm for the very first time at the hands of another person. After that, the feeling of his big, hard cock sliding into my tight virgin pussy was pretty fucking good too. I'd never let any of the younger boys go all the way before, so feeling his hard veiny meat as it parted my slippery, wet channel was sooooo wrong, and yet so very, very good at the same time. The guy was almost old enough to be my father, and that combined with the act of him spanking me had all kinds of warning lights and guilty thoughts flashing through my head."

I swallowed hard, my erection now throbbing painfully. Her very explicit and softly delivered description had totally sucked me in, especially the very graphic way she had painted the picture of her young, tight body being impaled by the thick, veiny cock of a much older man. Her fingers were gently teasing the head of my shaft again, and I realized I was really close to cumming. "Ummm, holy fuck that's hot. I had no idea you were so experienced," I muttered, a little lost for words.

"Well of course you didn't... Sir... you jumped to a very easy, but very erroneous conclusion." The softness of her breast pressing into my arm, and the way her breath tickled my ear were like dynamite to my libido. I could feel the pressure building, my balls pulled tight under my cock due to the hardness of my member. That pre-release sharpening of the senses, the increased heart rate and my elevated breathing all pointed to how effectively she was working me over.

I laid my hand over hers and stilled those expert fingers as I watched Carlo pick up two plates from the servery window and turn our way. Hooo boy! I was going to have to do something about this once we had eaten, as I was literally burning up with primal need. I straightened in my seat and leaned forward, causing Emma to do the same. She was careful not to pull the tablecloth over her lap though, and I rewarded her by gently dropping my fingers down between her legs and softly caressing her inner thigh. She widened her legs slightly in response, and I drew long, slow lines with the tips of my fingers as far down the top of her thigh as I could reach before circling around and coming slowly back up the inside until the blade of my hand brushed her lips and arrived back at the beginning again.