by Penny Birch
Mr Prufrock merely chuckled and continued to enjoy my bum. It was hardly the first time I’d been touched up, and I wasn’t even bare, but he was a man, and not just any man, but a dirty, lewd, old pervert, who was clearly enjoying my embarrassment and shame as much as the feel of my flesh. There was something awful about his touch too, something horribly intrusive, which made my stomach churn and my knees feel weak, but still I kept my hands on my head and my thoughts to myself.
I thought he was going to strip me, to lift my skirt and pull down my knickers and have a good grope of my bare flesh, probably pull my cheeks apart to inspect my anus and check pussy to see if I was a virgin, which I knew would be more than I could stand. Fortunately he contented himself with fondling me through my clothes, and finally stopped.
‘So it is true,’ he said. ‘Well I never.’
‘What do you mean?’ I asked.
‘Never you mind what I mean,’ he said, ‘just you get those little knickers off, and your skirt. I think I’ll have you work bare bottom today. In fact, I think I’ll have you work bare bottom every day. Just let me lock the door.’
I hesitated, wondering if I could negotiate, perhaps agreeing to go bare if he promised not to touch me too intimately, or whether I’d only succeed in revealing my darkest fears and encourage him to take advantage. He locked the door, twisting a huge iron key in a lock that looked as if it had been in place since the building was first put up.
‘Come along, let’s have you bare,’ he said as he turned again, his tone of voice suggesting he was talking to a not very intelligent child, or a dog.
Again I wondered if I should try to bargain, but decided against it. Struggling not to make faces, I reached up beneath my office skirt, took hold of my knickers and levered them down. He watched, his little piggy eyes bright with pleasure, as I removed my panties and hung them on a peg by the door, alongside his musty old overcoat. Now I was bare under my skirt, and as my fingers went to the zip they were trembling so badly I fumbled it twice before catching hold. I pushed it down and felt my skirt grow loose around my waist, bringing me a sharp sense of exposure, and worse as a little bit of my hip came on show; so bad I realised my courage was about to fail me and hurriedly pulled it down and off before it did.
‘Very pretty,’ Mr Prufrock remarked.
I hung my skirt up with my panties, trying not to show too much as I moved, and failing. The tails of my jacket and blouse almost covered my bum, leaving just the turn of my cheeks showing beneath, but I was quite bare at the front, pussy peeping out naked between my thighs, and I couldn’t resist shielding myself with my hands as I turned back to him.
‘Oh no you don’t,’ he chided, wagging one fat finger at me, ‘there’s no need to be shy, not in front of me. Yours won’t be the first bare fanny I’ve seen, you know.’
Very hesitantly, I took my hand away, to show him the tight pink V between my thighs. AJ likes me to shave, and I was bare, which made him raise his eyebrows and smack his lips, a gesture at once so dirty and so expectant I quickly covered myself again. This time he chuckled, and spoke with immense satisfaction.
‘Oh I do like them shy,’ he said, ‘dirty but shy, the best possible combination. Are you a virgin, dear Philippa?’
‘Yes,’ I admitted.
‘Not for long, I’ll be bound,’ he replied, chuckling again, and I just had to speak out.
‘Mr Prufrock, I . . . I don’t mind . . . don’t mind providing what you call little courtesies, but I’m afraid I’m not going to allow you to go that far.’
‘Oh you needn’t worry about that, my dear,’ he laughed. ‘Not that I would turn down a chance to pop that delightful little cherry, but I fear I have been unable to manage an erection for some years, rather over a decade in fact, and I dare not resort to medical assistance for fear of the condition of my heart. My doctor advises against it, you see, and . . .’
He went on for some time, describing his medical symptoms as I stood there with my hands shielding my pussy, feeling increasingly foolish. In the end I took my hand away, because it just seemed silly to be guarding my modesty when he’d already seen so much. As I exposed myself he stopped talking about his ailments, which was well worth giving him a flash anyway.
‘That’s my girl,’ he said. ‘It’s silly to hide yourself from a gentleman of my age and condition, isn’t it? Now, I believe you were sent down here to do some work, so if you wouldn’t mind going through this stack here and rearranging the files so that they’re in order of archive date instead of alphabetical, that would be most kind. You’ll stay bare, of course.’
I hadn’t imagined for an instant that I’d be allowed to cover up, and it was just the sort of dirty trick I’d have expected him to play on me, but that didn’t stop my resentment and sense of shame building as I went about my task. The work seemed pointless, at least as far as filing was concerned. From the point of view of making me show off, it was anything but pointless. I constantly had to stretch up and bend over, displaying my bum and pussy from all angles, while he sat in his chair and enjoyed the view.
At first I tried to show as little as possible, but it just made the work harder and more tedious than it already was. Gradually I gave in, at first keeping my body sideways on as much as possible, but soon abandoning that in favour of squatting down instead of bending so that I didn’t show too much behind, only to give in because it made my knees hurt. The last of my resistance came at the thought of him being the first man to see my bumhole, but I was forced to get into so many awkward positions I soon couldn’t be sure that he hadn’t. At last I gave in, too humiliated to care any more as I bent to pick up a pile of files and let my cheeks spread behind, showing off the little pink knot to his dirty, leering gaze. After that, I didn’t even bother to keep my legs closed. The damage was done, he’d seen it all, and if he wanted to examine my bumhole and the folds of my pussy lips in minute detail then that just made him a dirty old bastard.
I was hot and sweaty too, with stiff nipples and a creamy pussy despite myself. He’d made me humiliate myself in front of him and I was aroused, there was no point in denying it. I felt bewildered, even that I’d betrayed myself, but before too long I had to accept that I was ready for cock. Nor was it just for the bet. I wanted to be dirty, or better still, I wanted him to make me be dirty. That way I’d have fun and could win the bet too, while I could at least pretend to myself that I’d been cajoled into it, but he seemed content to watch.
He was sitting sprawled in his chair, his thighs open to show the bulge in his trousers, and if he wasn’t stiff then he was certainly big. As I worked he’d been touching himself occasionally, but that was all, and not enough, although goodness knows what the Blockhouse boys would have thought if they’d caught me working with my bum and pussy on show and Mr Prufrock watching me. I had to do something, so I told myself I’d sit on his knee and take him in my hand, which surely counted even if he couldn’t get an erection?
For maybe ten minutes more I continued to work, stretching and bending and squatting to expose myself to him, now deliberately in order to make my feelings stronger still. I even bent to retie a stack of files with my bottom full towards him, holding my pose and knowing full well he’d have a clear view of pussy pouting out between my thighs and the wrinkled pink knot of my bumhole above. Just knowing he could see that had me breathless, and finally allowed me to speak the words that would make me a complete and utter slut.
I stretched up to put the files on the shelf, making my tails lift to show my bare bum one last time, then turned to face him. There were plenty more shelves to do, but we both knew the work was pointless, and created only to provide plenty of opportunity for me to make a display of myself.
‘Er . . . Mr Prufrock,’ I said, ‘if you want a little favour, I don’t mind. Perhaps you’d like me to sit on your lap, and . . . hold you for a bit . . . hold your penis?’
I heard the words, but it was hard to believe they were coming from my own mouth. Even Mr Pruf
rock looked doubtful, but that didn’t stop him nodding and putting his hands to his fly. I watched, every second bringing me closer to making a tart of myself, as his zip peeled down, his trousers came wide, and he pulled open the hole in his underpants to flop out a fat, dark-skinned cock and a heavily wrinkled set of balls. Now ready for me, he spread his thighs a little further to leave the whole obscene mass dangling down between, and patted his leg.
‘Come along then, my dear.’
I realised I’d been holding back, but forced myself to step forward, to settle my bare bottom on his knee, and as his hand found the curve of my meat, to take his cock in mine. Now I’d done it, really done it. There I was, quite the little tart, sat bare bottom on a dirty old man’s lap, tugging his cock as he fondled me, and not minding in the least. Far from it. It felt lovely, to have my bottom bare and his hand kneading my flesh, to feel the heavy bulk of his penis in my grip, and to wonder if I could get him erect after all, to make him spunk up all over my hand.
‘Maggie was right, you are a dirty one,’ he said, ‘and what a firm little bottom you have. You don’t mind me feeling, do you?’
I shook my head, unable to express myself, or to admit out loud that I was enjoying the rude, intimate way he was fondling my bum. He had one hand cupping a cheek, so that his little finger was just an inch or so from my bumhole, which had begun to twitch and squeeze as I wondered if he’d get ruder still and touch it. I pushed my bottom out a little more, telling myself I was just getting comfortable on his lap, but in reality to make pussy available for his fingers. He gave his dirty little chuckle, and suddenly I could feel that his cock had begun to grow firmer and fatter in my hand.
‘I think you’re getting stiff, Mr Prufrock,’ I told him, and began to wank faster.
He was, his cock definitely swelling, and a wet pink helmet had begun to peep up from his foreskin at every tug. His hand moved a little, wringing a gasp and a sob from my lips as his little finger found my bumhole. I wanted to say no, to tell him he’d gone too far, but my instinct was the opposite, to push out my bottom even more. He began to poke at my anus, making it open a little, and with my hole slippery with pussy juice the tip of his finger was soon in.
I was sobbing with shame even as I began to wriggle my bottom on his intruding finger, wanting more. He obliged, slipping his hand beneath me to cup my bottom, now with a longer, thicker finger touching my anus. I tugged harder, the way Clive had explained I should wank a cock after I’d brought him off in my face, and in return had the new finger slipped in up my bumhole. He began to wriggle it around in my ring, filling my head with filthy thoughts, of being sodomised on my knees, or sitting fully in his lap with his erection up my bum, even of taking his dirty penis in my mouth once I’d been well and truly buggered.
‘That’s my darling,’ he rasped as I began to squirm my bottom on his finger. ‘You like a little attention to your botty hole, don’t you?’
Again I could only nod in agreement, the shame burning in my head as I admitted the awful truth. He pushed deeper and I gasped, my anus squeezing on his finger as he began to explore my rectum. His cock was nearly hard, flopping just a little with each tug of my hand, and long, and thick, far thicker than my bumhole could accommodate, I was sure, but I still wanted to try.
‘Do whatever you like to me,’ I sobbed, ‘anything at all.’
‘Then I’ll show you a little trick,’ he said, ‘a little trick you’ll thank me for the rest of your life.’
As he spoke he had begun to extract his finger from my anus. I lifted my bum, expecting to be shifted onto his erection as my bottom hole closed with a soft, bubbling fart, but he simply slipped his hand between my thighs, cupping pussy and starting to rub her with the finger he’d just had up my bum. He was going to masturbate me, and maybe he thought I’d never come.
I was going to now, my muscles squeezing even as he found my clit, and in a moment I was tugging furiously on his cock, still wishing he’d try to fuck my bottom, or fuck my cunt. He had me completely, his fingers working in the wet, mushy flesh of my sex as I squirmed my bare bottom on his hand and wanked him as hard as I could. I’d have done anything, let him spank me and grope me and take down my panties whenever he liked, as often as he liked, let him up my bum and suck his penis clean, let him take my virginity and fill my willing little hole with spunk . . .
He gave his filthy little chuckle as I came under his fingers, but that was it. His cock still wasn’t fully hard, certainly not hard enough to get in up my tiny bumhole, while the moment my orgasm had died all my feelings of shame and resentment came flooding back. Not that I said anything, because it would have seemed ridiculous after the way I’d behaved, and I knew I’d be back the next day, and with my knickers off.
Six
I HAD A lot of trouble coming to terms with what I’d done, and especially my own reactions. So many times I’d allowed the thought of dirty, humiliating sex with men to creep into my fantasies, but I had never imagined the reality could break down my resistance so absolutely. Not that I was any more attracted to men than before, let alone the appalling Mr Prufrock. It wasn’t the men who turned me on, it was the humiliation.
Two other things helped, that I was doing it to win my bet, and that I could try to see what I’d done as a act of charity. Take away the sex, and I had provided a lot of pleasure for a lonely old man, which was just the sort of thing I was always told I should be doing in Guides, although it very definitely did not include showing them my bum, let alone wanking them off. For the bet, everything was going to plan. Clive had the money on, and it was just a matter of me getting caught, although we had agreed to wait awhile to avoid arousing suspicions.
So for the rest of the week I followed the same hideously embarrassing routine; down to the basement, off with my panties and skirt, a little show for Mr Prufrock, an hour of work done bottomless. The work was the worst of it, because he invariably chose things that meant I had to stretch up or bend down, so that I was repeatedly showing off my bum, and quite often my anus and both front and rear views of pussy. He lapped it all up, his bright piggy eyes drinking in every rude detail of my body and every embarrassing little display I was forced to make, while I had to suffer the gradual build-up of my arousal and the inevitable consequences.
Unfortunately there was a problem. He was always careful to lock the door as soon as I came in, and once he had turned the big iron key in the lock he would put it in his jacket pocket until I was once more decent. Never once did he vary the routine, until I began to think that we would have to find some other way of getting me caught.
We also talked occasionally, generally once I’d been brought off under his fingers. Because I could never make him come, he was always at his horniest, and wanted to know all about my sex life, which he imagined as a series of bedtime romps with my school friends and clumsy fumblings by inexperienced boys. I pretended to be shy, which only made him all the more eager.
On the Friday morning I got him to confirm something I’d suspected all along. Maggie had substituted me for herself, ending an agreement to come down into the basement twice a week and pose for him while he played with his cock. I was not best pleased, especially as she was supposed to keep my secret between the four spanking enthusiasts, and Mr Prufrock was not included. She’d also broken the rules about spanking in the office, which tempted me to take my revenge by reporting her to Mr Montague.
The opportunity came almost immediately. I’d come up from the cellar for lunch, and Mr Prufrock had made me leave my knickers with him, so I was bare under my skirt, and perhaps Maggie had been made to do the same thing, as she smiled and raised her eyebrows when she met me on the stairs. All she got in return was a scowl as I wondered if I dare express my feelings then and there, but it merely seemed to amuse her.
‘Mr Prufrock is very pleased with you,’ she said.
‘I bet he is,’ I told her. ‘I don’t think it’s very fair, Maggie . . .’
‘Sh,’ she urged, lif
ting a finger to her lips. ‘After all, it’s what you like.’
‘No it is not!’
‘I think we both know you rather better than that, Pippa, don’t we?’
‘No . . .’
‘He tells me you like to sit on his knee and play with his cock, that you even suggested it, and that you like him to call you his ‘‘little tart’’.’
I felt my face go scarlet, instantly betraying myself. She gave me a knowing, sadistic smile and went on.
‘Perhaps I should tell him you enjoy playing spanking games? I don’t think he’s into it, but I’m sure he would be happy to oblige you.’
‘That’s not fair, Maggie,’ I blustered, but stopped as her smile grew broader and more evil still. ‘Please don’t?’
We reached the second-floor landing, and she stopped.
‘Then perhaps I should take you back upstairs?’ she suggested. ‘I miss your pretty little behind, and I suspect you’re overdue a spanking.’
‘I don’t want to be spanked by you,’ I answered. ‘AJ says I mustn’t, and . . .’
‘Then perhaps she’d be interested to hear how you let me warm your bottom before your little encounter with Mr Mulligan?’ she said. ‘Or perhaps she’d even like to know what you did for Mr Mulligan, flashing your little tail for him and the mechanics.’
‘You bitch!’
‘You will not call me that, Pippa. Get up to your room, now, and wait for me there. I’m going to spank you so hard . . .’
She stopped at the sound of a cough and I saw her face go pale. I spun round, to find Mr Todmorden standing behind me in the open door of his office.
‘Come in here, both of you,’ he demanded.
We went, and I was fidgeting badly as he closed the door behind us, sure he was just going to whip me across his knee and spank me pink whether I liked it or not, but when he spoke his words were addressed to Maggie.