by Penny Birch
‘That’s part of the plan, and I hope to have at least £5,000 for myself.’
To my surprise he wagged a fat finger at me.
‘Don’t let your emotions get involved, Pippa. After all, from what I hear you’re not particularly keen on men anyway.’
‘I’m a lesbian,’ I told him.
‘But you would be prepared to consider performing a sex act with a man in order to let me win this bet?’
I winced.
‘Yes, if I have to, but nothing . . . nothing too extreme.’
‘A pity,’ he said thoughtfully, now very much the lawyer, ‘because as I see it our ideal strategy would be for me to lay a series of relatively low-value bets on all the outsiders, ten pounds, let us say, and as I suppose you know, the odds vary according to what you actually do.’
It was my turn to blush.
‘I do know, but . . . but I’m still a virgin, and I’m not prepared to go that far.’
‘I assume the same applies to sodomy?’
Now I was really blushing as I shook my head in a definite no.
‘A pity,’ he repeated, this time not quite so lawyerly. ‘I take it you’ll accept fellatio?’
I nodded, ignoring the sudden sick feeling in my throat as I thought of how I would feel with a penis down it.
‘Which is three-quarter odds,’ he mused. ‘If we aim to win £10,000, we would therefore need to place a bet of, let me see . . . at least £134 at odds of 100–1. Hmm . . . I suspect Mark would be suspicious if I was to place a £150 bet on a 100–1 outsider, especially just after taking you for lunch. He’s not stupid. On the other hand, we’d only need £30 at 500–1 . . .’
‘Oh God, not Mr Prufrock.’
‘Emotions, Pippa. Do you want your £5,000 or not? I could just about get away with £30 each on the three male outsiders, especially if I put a larger bet on Steve, who’s the favourite now, and claimed I was hedging.’
‘Yes, but, Mr Prufrock . . .’
‘Just close your eyes and think of England.’
‘But he’s awful, like some sort of creepy gnome. Anyway, would Mark believe I’d do that?’
‘He wouldn’t have much choice, so long as there’s proof, but that’s a problem. Mark’s assuming one of the younger lawyers will succeed and it will be obvious from your attitude to him that he’s done the deed. Even there’s the problem of proving how far you went, and we’re supposed to get a picture of you performing on our mobiles.’
‘Bastards!’
‘They do it all the time, Den and Andy in particular.’
‘The dirty . . .’
‘Never mind that, Pippa, let’s concentrate on how to do this. You’re right, Mark might well be suspicious, unless he thinks you’re into older men . . .’
He went quiet, frowning in thought. I sipped my coffee, also thinking, and curiously detached, as if it wasn’t me who was going to have to take a big, dirty penis in my mouth and suck it until the spunk came out, but some other girl. That made it easier to accept that Clive’s reasoning made sense, and when he spoke again he had slotted the final pieces into place.
‘It can be done,’ he said. ‘Mark just needs to think that you had some good reason to fellate old Prufrock. It can’t be blackmail, because the rules exclude coercion of any form, but it could be money. Mark would believe that.’
‘That I’d take money for sex from Mr Prufrock!?’
‘I’m afraid that a lot of men believe all women are prostitutes at heart, although I do not, I hasten to add.’
I made a face. If Morris Rathwell was anything to go by, it was true. I even wondered if what we were planning counted, but I wasn’t actually being paid for sex, not as such.
‘In fact,’ Clive went on, ‘if Mark learns that you’ve fellated Mr Prufrock, he will automatically assume that money has changed hands, but that doesn’t affect the bet. It’s only because you look so innocent that he hasn’t set the odds to allow for something like that happening anyway. Then there’s the question of proof. The best way would be to ensure you get caught at it.’
‘Caught at it? Who by?’
‘It might raise Mark’s suspicions if it was myself, but it would be easy for me to text you when one of the others is likely to have to visit the archives. You’d have to leave the door unlocked, of course, and hope Prufrock doesn’t hear whoever it is coming. Hmm . . . tricky, but by no means impossible. We might not succeed immediately, but it would actually be more convincing if you were to be doing it regularly.’
‘Regularly?’ I echoed in horror.
Not only was I going to have to suck Mr Prufrock’s cock, but several times, and I’d be seen doing it too.
‘I’m not sure I can do this,’ I said.
Clive spread his hands and shrugged.
‘Whether to act or not is your choice,’ he said, ‘but that’s my best advice. I don’t suppose you’d care for another brandy?’
‘Yes I would, if that’s OK, thanks.’
He ordered the brandy, which was warm and strong. My fingers were shaking just at the thought of what I was taking on, and while part of me was screaming that it was an outrageous impossibility, I still had that odd sense of detachment. If I was going to do it, I needed that, because Clive was right that I had to get over my emotions. Ever since I first decided to study law I’d realised that in order to succeed I’d need to learn to be completely objective, and this surely was the perfect test of that ability? To judge by the way I felt, I seemed to be on course for an F.
‘I always get As,’ I said, not meaning to speak out loud.
‘I beg your pardon?’ Clive asked.
‘Sorry, I was talking to myself,’ I replied, ‘and trying to decide if I want to do this.’
‘You must weigh the benefits against the costs,’ he replied. ‘On the one hand, you have £5,000, on the other, one or more perhaps unpleasant but hopefully brief experiences. You must decide which way the scales tip, and act accordingly.’
‘I have to think about it.’
‘My advice, for what’s it’s worth, would be that the benefits vastly outweigh the costs.’
‘You’re a man, you would think that. Would you do it?’
‘Fellate Mr Prufrock for £5,000? No.’
‘Well then.’
‘But if I was a woman, and on trainee wages, I would.’
‘Do you think I’d be prostituting myself?’
‘No, not by the legal definition of prostitution.’
‘But Mark and the others will think I am, won’t they?’
‘There is that, but I feel I should point out that to them much of your appeal lies in your innocence. If they think you have already been corrupted they are less likely to pester you, and of course the bet would be closed. In fact, may I make a suggestion?’
‘Go ahead.’
‘Once you have moved on to university I could tell Mark the truth, or at least a close approximation of the truth. You would then no longer be the girl who fellated old Prufrock for money, but the girl who took Mark James for £10,000. The way in which you did it would merely add lustre to your reputation.’
‘The story would run for years, wouldn’t it? I want to go into law after uni.’
‘Then I suggest we follow the full plan. You might find some of the more stuffy chambers looking down their noses at you, but most firms would snap you up. Mark has quite a reputation, you know, and to have outwitted him so thoroughly . . .’
He left the sentence unfinished, and me feeling more confused than ever. Did it really work that way? Maybe it did. Presumably it did. If so I’d have a huge advantage, or would I just be dismissed as a dirty little tart? As Clive said, it all depended on people’s attitude, so I’d be a dirty tart to some and the Iron Lady to others. I only needed one.
‘I’ll do it,’ I said, and felt my stomach go tight at my own words.
‘Good for you,’ Clive answered, and raised his brandy glass.
I chinked mine against his and swallowed
the contents, which made my vision go fuzzy.
‘Another?’ Clive offered.
‘I think I need it,’ I told him.
He smiled, no longer shy, but confident and friendly. We spent a while over the next brandy, talking law and more personal things. I discovered that he’d been to a public school just a few miles from my own, and knew the River Pang and the Thames at Henley and above Reading. He even remembered the village where my grandmother lives, and the cantankerous old colonel who lived across the road in what is now my aunt’s house.
It was after four when we finally left Casa Azul, with the midday heat just beginning to fade and the giant gherkin reflecting rich yellow glitters from the sun. I didn’t feel at all steady, and when Clive laughed and offered his arm I took it. He slowed down, but we were walking towards the Minories and Montague, Montague, Todmorden and Montague. In the basement would be old Mr Prufrock, the dirty-minded, wrinkly old gnome whose penis I had to offer to take in my mouth.
I remembered how big it had looked, bulging beneath the crotch of his brown tweed trousers. His balls had looked pretty large too, and I wondered if he’d make me suck on them as well, a thought that made me gag a little. Maybe men always expected that? I didn’t know. Nor did I know much else, save what I’d picked up from friends, least of all how to make a man come quickly, which I could see might be very valuable knowledge in the days to come. It would be my first time.
Firsts are important to me, especially sexual firsts. My first spanking had been a wonderful experience I would remember with pleasure for the rest of my life, over Penny’s knee in an old pill-box beside the Thames with my school skirt lifted and my knickers well down. The first time I’d had pussy licked was equally intense, and when I’d first returned the favour. I could even remember the first time I’d put something inside myself, the mouthpiece of my recorder, and how I’d been so excited I’d done the same with my bumhole just hours later, holding my cheeks apart in the bathroom mirror as I squeezed a blob of toothpaste onto the tiny pink hole to help a finger go in, only to discover that toothpaste stings. Now there was another first on the horizon, the first time I sucked a man’s cock, my first blow-job, a disgusting, crude expression that always made me shiver, and it looked like it would be for Mr Prufrock.
I couldn’t bear it, not the first time. Yet I was headed for Montague, Montague, Todmorden and Montague, where Mr Prufrock lurked in the cellar. I was drunk, and feeling vulnerable, horny too, although I didn’t want to admit it to myself. Once I got there, down I’d go, in more ways than one, quite possibly, down the steep old stairs and down on Mr Prufrock, taking his fat, wrinkly cock in my mouth, sucking until it began to swell, doing whatever dirty things he told me to until he was ready, and then taking his load. For the rest of my life I’d know that had been my first.
‘I don’t really want to go back to the office,’ I said.
‘It might be an idea to sober up a little, certainly,’ he agreed. ‘We could stop for another coffee? Or I only live down by St Katharine Dock, if you’d prefer to sleep it off?’
I nodded and took him by the hand, signalling a cab with the other. The journey took just minutes, which seemed to pass in a dream. His flat was in a squat, brick block, overlooking the water and a cluster of yachts and motor launches. One of them was his, and he wanted to point it out to me, but I wasn’t interested. I knew that if I hesitated I’d lose my nerve.
‘I don’t want to see your yacht,’ I told him. ‘I want to suck your cock.’
He looked at me in astonishment, but I cuddled him, hugging him with one arm as I burrowed for his fly.
‘Er . . . um . . . Pippa, I think you’re drunk,’ he spluttered.
‘I know I’m drunk,’ I told him, ‘so you’d better get your cock out and pop it in my mouth while you have the chance.’
‘But, Pippa, I think you might regret what you’re doing, so . . . oh God!’
I’d pulled his fly down and my hand was inside his trousers, squeezing at the fat, soft bulge in his underpants. He made an odd little whimpering sound in his throat as I kneaded him, the same way I’d have kneaded a girl’s pussy with my hand down her knickers, because it was all I knew. Not that he was going to stop me, his eyes closed in guilty bliss, one podgy hand now on my back, and moving lower.
He gave a sob as his fingers closed on my bottom, and I let him fondle me for a moment before pushing him gently back to the huge, cream-coloured sofa. I always licked AJ on my knees, and I got down into the same position for Clive, with him sprawled on the sofa, his legs wide apart. He was mine, completely, staring in delight and in awe as I finished unfastening his trousers to expose white underpants beneath, lumpy with the mass of his genitals.
‘You’re going to have to teach me how to do this,’ I told him. ‘It’s my first time, with a man.’
‘Oh God,’ he repeated. ‘I think I’ve died and gone to Heaven.’
‘I’m not sure they do this in Heaven,’ I said, and slipped my hand into the opening of his Y-fronts.
He felt warm and soft, silky too, really rather a nice feeling. I began to explore him, stroking his balls and taking hold of his cock, which had begun to swell, making a long bulge beneath the white cotton. He was watching, enraptured, but silent.
‘You’re supposed to be teaching me how to do this,’ I reminded him.
‘You . . . you’re doing very well,’ he assured me. ‘Don’t feel you need to rush. Just pull up and down . . . yes, like that, and feel my balls, if you like.’
The bulge in his pants was growing rapidly now, his cock extending to one side as I began to stroke his balls once more. They felt strange, shifting under my fingers as if they had a life of their own, and it was amazing how big his cock was getting.
‘You’d better take me out,’ he sighed.
I nodded and tugged the hole in his Y-fronts open, to pull out his cock, a plump, pink tower of meat, almost as heavily veined as Trilby’s dildo. A thick collar of wrinkled skin surrounded the top, with the tip of a moist, bright pink helmet just beginning to poke out. I could smell him too, a scent very different from pussy, which made my nose wrinkle but which seemed to be helping send little shivers down my belly to my sex.
‘Take my balls out too, please,’ he instructed, his confidence rising to my obvious enthusiasm.
I complied, scooping his balls sack out of his underpants to leave it lying fat and heavy on a bed of plain white cotton with his cock rearing above, now maybe halfway to being hard. It looked rather nice, and very rude, hideously ugly, but still desirable. I took him in my hand and began to pull up and down as I had before, stroking and tickling his balls at the same time.
‘A little harder,’ he sighed, ‘and roll my foreskin back, please. Yes, like that, only with your finger and thumb in a ring. Yes, perfect . . . oh God . . .’
‘Do men like that?’ I asked.
All he seemed to be able to manage was a nod, and his mouth was slack with pleasure, so presumably they did. It looked rather comical to me, with the big pink hat of his cock head popping in and out of his foreskin as I rolled it up and down, but he was soon too big to keep it in. He was hard too, his cock shaft now curving up from his belly with the big veins standing out blue on his pale skin.
‘Are you fully erect?’ I asked him, and he gave a weak nod.
‘Then I suppose I’d better suck you off,’ I said doubtfully.
‘Yes, please,’ he answered. ‘If you want to.’
‘I do,’ I assured him. ‘I really do, just not yet.’
I continued to masturbate him, wondering if I’d ever seen anything at once so repellent and so attractive as his erect cock and heavy balls. Girls are pretty all over, not men, and I was supposed to put the hideous thing in my mouth, and suck. I was going to do it, too, just as soon as I’d plucked up enough courage. My mouth came open and I was telling myself I’d put him in on the count of ten, then twenty, then thirty, all the while tugging at his now straining shaft.
‘Yo
u’d better do it, Pippa,’ he gasped, ‘or I’m going to come in your hand.’
‘Hang on,’ I told him, ‘not yet.’
‘Stop it then.’
He took over from me as I let go, opening his eyes to stare down. I smiled back, nervous and embarrassed, but excited too, and rather enjoying myself. He spoke.
‘Would you . . . would you mind taking your top off? A lot of men like a girl to do it topless, or at least with her breasts bare.’
I wasn’t doing that for old Prufrock, but now I didn’t mind. Nodding my agreement, I quickly shrugged off my jacket and undid my tie, with Clive staring all the while, as if he couldn’t bear to miss a single instant of my little show. I did my blouse buttons slowly, teasing him just the way I’d teased the girls when AJ had me perform a striptease at Whispers. His eyes stayed glued to me, and he was nursing his erection as he watched.
‘Is this good?’ I asked.
He nodded dumbly. I eased my blouse off down my arms, wondering how best to show my breasts. AJ likes to make me strip quickly, or to pull my clothes off herself. Penny likes to flip my bra up before she spanks me, and I tried the same, taking hold of the undersides of my cups and tugging them up. Clive gave a soft moan and began to wank faster.
‘Good?’ I asked, although the answer was pretty obvious.
‘Perfect,’ he sighed. ‘I love to see a girl play peek-a-boo with her tits, and yours are no nice, small and perfect . . . and your little rosy nipples, so stiff . . . and . . . oh God, suck my cock, Pippa . . . suck it, I’m going to come.’
‘Hold on!’ I urged.
I moved quickly forward, determined to do it, and this time my urgency got the better of me. His hand came away and mine had replaced it, holding his big, silky shaft as I opened my mouth, to take him in, sucking a man’s penis for the first time in my life. He groaned, and I thought he’d come, but there was nothing extra in my mouth. If anything, he seemed to have got himself under better control, and I drew back, once more tugging gently at his shaft.
‘Come on, Clive, teach me,’ I urged.
‘Like you were,’ he sighed. ‘Come on, Pippa, finish me . . . be my little cock sucker.’