On Demand

by Justine Elyot

  Mrs Ross loitered in the boutique across the road from Gregg and Saunders for longer than she had planned. For the eighth time, she peered into her handbag to make sure she had not dropped or lost the items that were burning a hole in the leather. Still there. She still could not quite believe she had actually crossed the threshold of Desirez, still less placed these two things on the counter and handed over money for them. She had avoided the cashier's eye quite successfully but he had insisted on asking, 'You're sure this is the size you want?' and she had been able to do no more than nod tightly.

  The thought of that anxious exchange was unaccountably erotic now, though; every time she remembered it, an additional peripheral detail slotted into place. How the raincoated man at the magazine stand had looked at her. The bizarre items hanging from the wall. The row of huge dildoes behind the glass counter. It was like a different world, and yet it must be normal to some people. Normal to Mr Gregg. Mr Gregg and Desirez stood on one side of a line dividing her self, while Colin and Waitrose inhabited the other. Talk about a split personality, she thought, disapproving of herself even as she was psyching herself up to cross the road.

  Nothing was going to stop her now that the wheels were in motion, least of all her own conscience. That ordeal in the sex shop would have to be redeemed.

  'Mrs Ross is here for her appointment, Mr Gregg.'

  'Ah, good. Show her in.'

  The receptionist replaced the receiver and smiled brightly at Mrs Ross, who was reminded of herself as a young trainee. Was Gregg knocking this one off as well? she wondered. None of her business if he was, of course, though she could not help but twinge at the idea.

  'You went to the shop?' were Gregg's first words to her once they were closeted in the office.

  'Yes. Somehow. I'm not sure how I got through it.'

  'Brave girl.' He smiled. 'Come and show me what you bought.'

  Mrs Ross fumbled in her handbag, placing the two purchases side by side on Gregg's desk.

  'Ah, yes, this is the right size to start off with,' he said, turning the little pink silicone plug around in his hands. 'And the lube . . . yes. That'll do nicely. I must say, Lynnie –' he looked up, grinning '– you have surprised me. I thought you'd take fright when the prospect was real. You're still on board?'

  Mrs Ross found the management-speak a little incongruous, but she nodded, transfixed at the sight of the plug, and the man who meant to put it in her, together.

  'OK. Then I must ask you to come over here, Miss Lynnie Speedwell, and lift up your skirt.'

  The use of her maiden name made Mrs Ross feel like his young employee again, banishing all doubts and thoughts of resistance. She shuffled shyly to his side of the desk and stood in front of him, performing a slow shimmy of the pencil skirt until it bunched around her waist, exposing stocking tops and a pair of high-cut tight-fitting briefs.

  'Good; just what I said you should wear,' said Gregg approvingly. 'Now I'd like you to put yourself over my lap, please, young lady.'

  'Over your lap?' Mrs Ross baulked slightly.

  'Yes, it's easier and more comfortable, the first time. Don't worry, I'm not going to spank you. Unless you'd like me to?'

  Mrs Ross giggled hysterically. 'Not right now,' she managed. She bent forward awkwardly, balancing herself with one palm on the floor while her stomach pressed into Mr Gregg's thighs and her legs hung down, not quite finding the ground.

  'Get as comfortable as you can,' advised Gregg, moving about in his chair to accommodate her until she was settled. 'A sofa is best for this kind of thing really. Never mind. Now then.'

  He peeled the skin-tight knickers down over her backside until it was fully exposed to his view, tugging them down as far as the stocking tops so he had an extra little peek at the lips of her pussy, which seemed temptingly sheeny.

  Mrs Ross felt a little awkward, dangling so, with the dry office air circulating around her naked bottom, but the first brush of palm on curvaceous cheek was so much more than she had been hoping for that she let out a little sigh.

  'Aren't you ever touched here?' Gregg wanted to know.

  'Hardly ever. It seems like some kind of forbidden zone for some reason. I have to make it clear though, that this is the only part of me you get to touch. No straying off the beaten track.'

  'Beaten? You really would like a spanking?'

  'No! You know what I mean!'

  Gregg chuckled and began gliding his palm across the surface of her posterior, brushing in broad circular motions, moving inward and inward until Mrs Ross was a compliant ragdoll oohing and aahing with satisfaction and getting perilously close to staining the dark trousers he was wearing.

  'Does that feel good?'

  'Oh, it does . . . better than I imagined . . . it feels so naughty somehow.'

  'Well, it's about to get naughtier . . . stay nice and relaxed now . . .'

  Mrs Ross stayed still as glass while Gregg gently opened the furrow and worked skilled fingers down the sheering sides, so slowly that she could not take fright, so effectively that she began to breathe again, properly, heavily, and then she knew she would have to move.

  She had ordered herself not to, but she began to gyrate a little, pushing her bottom up further and looking for relief for her very wet and very needy sex. Now that Gregg's fingers were circling the central opening with an inevitability she was finding highly erotic, she could finally understand the lots of women who liked it. She knew where they were coming from . . . and why they were coming. On a mental level it felt richly, wildly rude, but on a physical level it was also unexpectedly delicious; she had not realised that attention to her rear could connect up to her clitoris, as if a row of flashing lights lit up in sequence between the erogenous zones.

  'So what do you think?' murmured Gregg, his thumb having reached the apex of his intentions. 'You can still say no if you want.'

  'No, no. I mean, please. I mean, do it.'

  'OK. Hold tight and don't tense those muscles.'

  There was a pause, then Mrs Ross squeaked momentarily at the sensation of cold gel against her tightest hole, kicking her legs until Gregg put a steadying hand on one thigh. She could hear sounds from above, very faint liquidy sounds of things being squeezed from tubes. She could also hear tiny squishes from between her legs, every time she made a move. The suspense was almost too much.

  And then it wasn't! 'Ah!' she announced when the thumb returned, slipping around the lubricated circle then pushing, slowly but inexorably, against the barricades.

  'Don't tense,' advised Gregg, stopping momentarily as the ring of muscle closed around him. Mrs Ross made a herculean effort and unclenched, letting him through, giving him access, squirming and babbling a little, but making no other attempt to halt his excavations. It felt strange but not significantly painful, she thought, even when he twisted the thumb around, prodding and poking at her secret passage.

  'How's that, Lynnie?' he asked.

  'It's . . . good, I think. Doesn't really hurt.'

  'No, this shouldn't. You'll need to work on taking anything bigger though. All right. Now I'm going to insert the plug. Keep still and don't tense.'

  His thumb popped out, to be swiftly replaced by the slim length of silicone, feeling a little chill at first, but soon warming up. Its presence was certainly noticeable, but it did not stretch or sting or hurt. Gregg pushed and pulled it back and forth, until Mrs Ross had to bite her tongue to keep from begging him to fuck her. She wanted it badly, madly, cock, fingers, tongue, whatever.

  'See, it's good, isn't it?' crooned Gregg, steering the plug with relish, mindful of the juice flow he was precipitating. 'I was right, wasn't I? Aren't you sorry you didn't take the chance before?'

  'Oh yes, I am, very sorry,' gasped Mrs Ross. 'Oh God, oh God.'

  'Good. Right.' Mr Gregg stopped abruptly and pulled Mrs Ross's knickers back up. 'On your feet, Mrs Ross.'

  She almost howled with disappointment, but she did as she was told, feeling her bottom cheeks clamp togeth
er and her muscles tighten around her little invader. While she pulled the skirt down, Gregg issued further directives.

  'You will keep that in until you get home,' he told her. 'And on the way home, I want you to call in at the town library and look for all the information you can find on anal intercourse. Tomorrow morning, you will re-insert the plug yourself and come back here so I can replace it with a larger one. And so it will go on until you are ready. Yes?'

  'Yes,' whispered Mrs Ross.

  'Good. You've done very well today. I'm proud of you. I'll see you tomorrow then.'

  Mrs Ross dithered for a minute, staring at him pleadingly, then said, 'OK,' and scuttled out.

  All the way to the library, she imagined people could see what she was wearing, X-raying beneath her skirt and underwear. Did it affect her walk? It did a little, for she had to keep her muscles taut to stop it from slipping out. By the time she got to the library, she was burning up with the need for an orgasm; she grabbed the first sex-related book she could see, raced to a cubicle and sat down, grinding her bottom against the seat to fully feel the impact of the plug while her hand sped straight down the waistband of her skirt to her knickers. Head down on the open book, legs splayed and bum plugged, Mrs Ross brought herself to a muffled, tearstreaked climax in the Silent Reading area of the Central Library.

  Slowly, carefully, Gregg opened Mrs Ross's bottom further and wider, bending her over his desk each day to give her stretching arsehole his tender and thorough attentions, until the day came when he judged her to be sufficiently trained to receive the ultimate plugging.

  Not in the office, though, where the staff were beginning to raise eyebrows at the frequent appointments which left Gregg flushed and the air unaccountably perfumed.

  No, Gregg was taking Mrs Ross upmarket – to the best hotel in town.

  'The name's Barker,' he told me, peeling off notes from a wad into my complicit paw.

  'Very good, Mr Barker,' I said, entering him on the database.

  'When my wife –' he paused to wink '– turns up, show her straight to the room, please.' 'Mrs Barker? Will do.'

  'Thanks. Take a twenty for yourself, Sophie.' 'Thank you, Sir.'

  Mrs Ross – or was it Barker? Oh, she hated the subterfuge but she had come too far now – stepped out of the lift, tightening her sphincter subconsciously for her final moments as an anal virgin.

  'I feel as if I ought to kiss you. I want to kiss you,' said Gregg, on opening the door.

  'No kissing,' said Mrs Ross tightly, taking in a symphony of muted creams and beiges from the full-length curtains to the carpet to the . . .

  'It's a nice bed, isn't it?' Now that they were here, Gregg felt a little awkward; this was not the sort of social scenario he often played out. What was the etiquette when you were meeting a happily married woman to give her her inaugural buggering?

  'It's enormous,' remarked Mrs Ross nervously.

  'So . . . do you want a drink or something first?' Gregg hovered by the minibar, squinting at a packet of dry roasted peanuts.

  'Oh, God, no. Let's do the deed and get out of here.' Mrs Ross laughed, a little too shrilly. Gregg saw that somebody needed to take control of the situation and decided that it might as well be him.

  'All right,' he said. 'I'll ignore the blow to my pride and self-esteem and cut to the chase. Take off your skirt.'

  Mrs Ross caught her breath, obscurely grateful to Gregg for seizing the initiative and taking it out of her hands. He made me do it.

  She walked to the foot of the bed, slowly unzipped and let her tweed pencil skirt crumple around her ankles.

  Gregg was heartened by the sight of her firm flesh framed by white suspender straps and sheer stockings. Mrs Ross had not bothered with knickers today, which was practical in one way, but it would deny him the pleasure of ripping them down.

  Ah well, there were other ways to work off frustration.

  'Very nice; get on the bed on all fours now. I suppose I can't persuade you to take off your blouse?'

  'I'd rather not,' said Mrs Ross, crawling on to the plump duvet and sinking her hands and knees into its soft embrace.

  'And as for foreplay?'

  'I . . . just do what you would do, as if foreplay was over,' gasped Mrs Ross, starting to wetten at the very thought of what was to come. 'I'll be fine.'

  'If you're sure.'

  She shuddered a little at the sounds of uncapping, unbuckling, unzipping that ensued, knowing that the next un- might well be her undoing. She bit her lip when the mattress tilted underneath Gregg's weight. He's behind you, she thought, wanting to giggle at the pantomime association of the phrase. She listened to the sound of lubricant being squelchily warmed between his palms, letting her mind run on in this vein. Oh no he isn't! The mattress sloped ominously lower; a breath of air from his movements wafted over her displayed bottom. Oh yes he is!

  And now a hand descended, grabbing a plump handful of bum before parting the cheeks, opening her to her fate. She felt the lubricant on the tips of his fingers as they massaged her well-trained bud, prodding and probing, precipitating a wanton need for him to go further, so that she welcomed the eventual blunt pressure of his erection in their place.

  Knock knock.

  It felt wider than any of the plugs, and the heat of it was unfamiliar after a week of cold smoothness lodged inside. Mrs Ross was suddenly sure it would never fit, bucking in a moment of panic until Gregg had to clamp an arm beneath her stomach, holding her in place.

  'It will be all right,' he reassured.

  'It seems so thick,' she whimpered.

  'It will hurt a little, but you knew that, Lynnie. You know what to do. Don't tense and it will soon pass.'

  He began to push. Mrs Ross tried very hard to keep from clamping him, but the ring of muscle had a treacherous will of its own. All the same, Gregg was patient, holding still until she had controlled it enough to let him continue. Infinitesimally, he glided onward while Mrs Ross's eyes stretched as wide as her rear orifice, astonished that he had even made it this far and disbelieving his clear intention to forge ahead regardless.

  'Oh! Oh no!' she cried, stabbing pain shooting through her stomach, but Gregg had come this far and there was no turning back.

  'Yes, it will pass,' he repeated through gritted teeth, her hips tightly gripped, his head full of the sight of his glistening shaft disappearing inexorably into the sunless depths of her backside. 'Take it all, Lynnie. God, I wish you could see it. I wish you could see your arse stuffed full of my cock.'

  'Aaargh!' she replied, but he was right; the worst of the pain was swiftly over, replaced by the most intense fullness and an inescapable, strangely sexy sense of helplessness. There was a man's cock in her bum, and nothing she could do about it.

  He crept up to the hilt and stayed there for long gloating moments, staring at his rooted tool and the stretched sheath in which it reclined.

  'How does it feel?' he asked.

  'So weird,' she said faintly. 'So full. Stuffed. Full.'

  'Good,' he said, and then he began to draw back. Mrs Ross felt as if her entire being and body were concentrated in the nerve endings along her back passage; just to make sure that this wasn't the case, she let her hand flit down between her legs to that other seat of sensation. Oh, it was ready for some stimulation, it seemed.

  As Gregg continued to plough his new furrow with diligence, Mrs Ross batted her clitoris between finger and thumb, falling into a new world of sensation, enjoying every element of it, moaning into the duvet with ever-increasing volume as her bottom was comprehensively commandeered.