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.