tagGay MalePony Boy Ch. 05

Pony Boy Ch. 05

byChestersBoi©

This is the fourth chapter of 'Pony Boy' and, if you haven't read the rest, then please do so first. Quite a bit of the story refers back to events in the earlier parts and it won't make much sense if you read them out of order.

And, of course, there are the usual disclaimers; anyone involved in sexual acts is over eighteen and we're all fictional.

Enjoy


**********

It was noon on Saturday before I finally woke up and, when I went to the kitchen area of my bedsit to fill the kettle and make myself some coffee, I couldn't help but notice my bright scarlet fingernails. Top of my 'to do' list had to be going out and getting some nail varnish remover. Getting caught with painted nails would lead to all sorts of questions, none of which I was ready to answer. I nipped down to the local discount chemists and, blushing somewhat as I paid, went and bought some, along with baby wipes and a few other bits and pieces.

As I scrubbed at my nails I thought things over. I had a lot to think about. This whole thing was escalating out of control. Right at the beginning I had just thought that I'd run a few races. OK, so I'd be naked but, I thought, that would be it. No sex apart from, as Mr. H had once said, a little groping.

And now? And now I'm up on the stage being caned and sodomised for the entertainment of some sort of East End gangster.

Mr. Bothwick's coming home party had been simultaneously frightening, exhilarating, exciting, painful, sordid, erotic, and, above all, an intense experience. There can be few things more degrading than being on your knees in some filthy toilet stall giving a complete stranger a blow job and yet... and yet... just thinking about holding their hardening cocks in my hands, taking them in my mouth, feeling them respond, hearing them gasp with pleasure as they came, sent little tingles through me. It was almost as if I wanted to see how far down this walk on the wild side could take me.

There was the same sort of ambivalence when I thought about how the way in which Mr. Bothwick had used me. I had been nothing to him, a mere party favour that Mr. Mason had laid on for his amusement. But, more than that, Mr. Bothwick had sought to humiliate me further by making me watch myself in the mirror. He had wanted to rape my dignity as well as my arse. But this had backfired. I had wanted to watch, I had wanted to savour the humiliation. By humiliating me, especially when dressed as Belinda Bombshell, he was playing to my deepest, darkest fantasies.

And if ever there was a tangled web of emotions then it was my relationship with Belinda Bombshell. Was she my inner whore? She certainly wasn't me, except, of course, she was. Right from the start, when I had been sat on Arthur's knee, I had discovered the simpering coquette that lived inside me. Last night, putting on the clothes, the wig, the makeup, had transformed not just my looks but my whole persona. Acting as Belinda Bombshell I would do, and be, things I wouldn't dream of doing otherwise. Importantly, although it was Belinda Bombshell who was doing these things, it was Ben who was getting the kicks from it.

And finally, as I worked away at the bits of varnish that seemed to get stuck in the cracks, I thought about my relationship with Jed. It had been Mr Jarman's idea of a sick joke to make us perform together, to play to our well known rivalry. Now it seemed that we were stuck with each other. The thing was, now that I was getting to know him, he wasn't that bad a guy. He had had every opportunity to make me suffer and yet, when push came to shove, he had been almost gentle with me. Being fucked by Mr. Bothwick had turned me on because of the thrills, the danger, the edginess. Being fucked by Jed had turned me on because he felt good inside me. I wondered what it would be like to have him fuck me when we weren't surrounded by onlookers, if it were for us, not for an audience.

When my nails were finally clean I took my clothes down to the launderette. Both skirts, several pairs of panties and my blouse all needed washing. I mixed in a few tee shirts and my towel to make it look a little more normal. As for my shoes, they were all but ruined where the toes had been scratched from all the kneeling. If, as Mr. Mason had intimated, we were to do this again, then a new pair would be needed. I'd have to ask Mr H about that when I went to get paid on Monday.

On Sunday I had a footie match and this meant that there was a Rubicon I had to cross. There was no way I could wear my footie kit without it being completely obvious that my arms and legs were shaven and, when we showered together afterwards, my mates would see that the rest of me was bare. However, there was no way round it. Mr. Mason was not going to let me stop shaving so the choice was give up footie or brave it out. I really didn't want to give up footie, especially as all the gym work I was doing had made me fitter and faster.

"Hello Ben, what happened? Get a bit carried away with the razor?"

"I lost a drunken bet with this girl I met down at Club Sanuuk and, after that, well, once you try it you never go back."

"Bollocks, you're just gay."

"Bollocks to you too. Seriously, it was a bit strange at first but Wendy, that's the girl I met, she went wild for it. Shame she was such an airhead. I like a bit of conversation after the sex."

"Ooh, listen to Casanova! Still, if you score goals as fast as you score birds you can be as bald as a coot for all I care."

And, effectively, that was it. I did get one or two strange stares but, once we were out on the pitch, the extra pace I'd picked up from the training held me in good stead and I was tearing through the opposition defence. After that no one gave a damn. In the showers afterwards there was a certain amount of joshing but it was clear that, although I was thought a bit odd, I had got away with it.

Monday lunchtime found me, once again, climbing the stairs to Mr H's office. Tracy sent me through to the inner sanctum where, once again, Mr. Mason and Jed were also in attendance. Naturally sorting out our wages was the first order of business. Apparently we were to be paid two hundred each plus, of course, our three quarter share of the tips.

"Before you count out the money...," I said as Mr H took the notes out of the cash box. I was really nervous about what I was about to say and it would have been easiest if I stayed quiet but I had worried about this all weekend and was determined to see it through. "Look, it's about the tips. I think they should be shared fifty, fifty."

"Really? That's very generous of you," Mr. Mason looked amazed.

"It's just that.... Look, when it's a race meeting we're all equal and it's every pony for themselves, right? I've got no problem with that and I'm not suggesting we share tips from race meetings."

"I should fuckin' well hope so," Jed interjected.

"But when we're doing these shows, and I assume there will be more of them," I looked at Mr. Mason who nodded, "then it's not the same at all. We're not competing against each other, we're working together. The tips we get, it's for the show and we're both part of the show." Still they seemed unconvinced. "Look, it's like when I worked in a pub," I continued. "All the tips went into a jar and, at the end of the night we split them evenly."

"What about you, Jed, how do you feel about this."

"Well, I'm not going to turn it down, am I? But race nights, that's different."

"Race nights are different," I agreed.

"Well, if that's the way you want it," Mr H said, "then there's a grand total of five hundred and eighty in tips, minus my twenty five percent is four thirty five, split two ways is two hundred and seventeen pounds and fifty pennies. I'm not mucking around with change. You get two fifteen each and you two can fight over the fiver. Now, can we get on?"

Jed and I pocketed the money and he was gracious enough to let me have the spare fiver.

"As young Ben suggested," Mr. Mason said once we had settled down again, "I have had one or two enquiries about your little show. It looks like the two of you are going to be pretty busy, what with one thing and another. For the first few we ought to be able to get away with the naughty schoolgirl routine but you can't carry on with that forever. If we don't change the show it will get stale. I've got a number of ideas."

All the ideas were fundamentally the same. I, or rather Belinda Bombshell, would be dressed up as the naughty nurse, maid, waitress, secretary or whatever and Jed would be the doctor, butler, diner or boss to match. I would do something naughty; he would punish me and then fuck me.

"How about threesomes?" Mr. H suggested. "We could use Carl. Get that black kid and white kid thing."

"Could do. One either side as the cane him, sort of thing, and then one fucks him as he blows the other. That'll work. We could probably charge more too. Yeah, nice one Harold."

I stood there somewhat aghast. Jed had prophesied this but I hadn't really believed him, or, rather, I hadn't appreciated the import of what he had said.

"Do Jed and I get any say in this?" I asked.

"Have you got any better ideas?"

"Not really, it's just that...."

"In which case your job is to shut up and get on with it. We've got a nice little earner here so don't you go getting all stroppy on me. Now, your next booking is next Saturday so you've got a week to get your act together. Do I hear any objections?"

"No, Mr. Mason," Jed replied immediately. I was less certain.

"Ben?"

"No, Mr. Mason," I replied reluctantly. I had a whole bundle of objections but Mr. Mason wasn't in the least bit interested in hearing about them. "One thing though...."

"What now?"

"My shoes. They..."

"What about your shoes?"

"They got ruined with all the kneeling I had to do."

"Then you had better buy some new ones. That costume you're wearing came out of my pocket but I'm not going to stump up every time you get careless. If you can't look after it properly then it's up to you to replace anything you ruin."

"It's just that I'm not sure where to go," I added hastily. I had hoped that he might pay for them but, instead, he seemed to be getting more and more impatient with me. "I mean, I can't just walk into Shoemarket and ask to see their latest range."

"Tracy knows the place," Mr. H answered for Mr. Mason. "Check with her before you leave."

"And while we're on the subject of who pays for what," Mr. Mason started again. "I also paid for Tracy and Maureen to sort out your makeup. That's not going to happen again. If you're not clever enough to do your own then it's going to be up to you to make your own arrangements."

"But I don't know how...."

"Then you've got a week to learn, haven't you. Now, there's a race meeting on Thursday, and I've got some outdoor racing for you on Friday, and then there's the show on Saturday. You two have got a busy week ahead. I suggest you go and get on with it."

And, with that, we were dismissed. One in the front office I went to Tracy's desk, and asked her about the name of the specialist shoe shop.

"Try this place. Give them a ring first and tell them I sent you. While I've got you, did Mr. Mason talk to you about makeup? If you want me and my mum to do it then we want a ton a head and we need to know in plenty of time."

"I want to see what I can do for myself," I said. Two hundred quid! That came to what I was paid for the show and the thought of handing it all over to Tracy and her mum didn't appeal.

"If you say so but you had better do a decent job of it."

"Are you two discussing makeup?" Mr. Mason had appeared at the door and saw me chatting to Tracy.

"Ben seems to think he doesn't need me," Tracy replied.

"Really? I'm not paying for clowns here, I want a proper show and, if he's a fuck up, then I'm holding you responsible."

"Why me?" Tracy started but then she sighed. "OK, it's always me. Ben, you don't go solo without my say so. Drop by the office Thursday and I'll see how you're getting on. Five o'clock, say."

"Make sure he's ready. Don't let me down on this. Now, have you got last month's accounts?"

"Here they are, Mr. Mason," she said, handing him a file, "and don't worry about Ben. I'll make sure he's ready."

Mr. Mason disappeared back into the inner sanctum.

"If you think I'm putting my neck on the line for you then you've got another think coming. I'll see you here on Thursday, Ben, and, unless you can convince me that you're good enough, then, like it or not, you're hiring mum and me to do it for you. Be here at five o'clock and don't be late."

And, with that, Jed and I left.

"OK, OK, don't get all 'told you so'," I joked to Jed as we made our way through the traffic to Hackney.

"And you still think you can walk away when you want to? You belong to Mr. Mason now and he won't let go as long as he can earn money out of you."

"I've got the Easter holidays coming up soon. My family will be expecting me back home."

"They can expect all they want. I can't see Mr. Mason letting you go."

"But he'll have to. It's only for three weeks or so."

"Have to? I don't think so. If I were you I'd start thinking up some excuses. Pound to a penny you don't get to go."

I dropped Jed off and drove back home, my head spinning with what I had been told. With each revelation I was finding just how naive I had been. Just a few races, just until I had got enough to go to Malaysia, and no sex, well, apart from a little groping. I should have known it would never stop at that. I still wasn't completely convinced. Next time I saw Mr. Mason I would ask him about Easter, see if I could get the time off. After all, he had seemed quite reasonable, hadn't he?

But in the meanwhile I had my work cut out. Apart from all my college stuff I had to buy myself some new shoes and I had to learn how to put on make up. The thought of having to shell out two hundred quid to Tracy and her mum every time we went on stage was not an appealing one. Once you factored in the shoes I could end up losing money, not earning it. Maybe my suggestion that we share the tips had been a trifle generous. After all, Jed didn't have the expenses I had. Not that I'd go back on that anyway. Jed had made it clear that I'd made a friend with that gesture and it was looking like I would need all the friends I could get.

As soon as I got home I fired up my laptop, went on to YouTube and searched for "How To Apply Makeup" and, when I saw the number of hits, I narrowed it down to "How To Apply Makeup For Crossdressers". For maybe an hour I watched and studied and all the time I was building a shopping list. I looked at the time, the shops were still open; there was still time to go to the chemists and buy the stuff for real.

When I got there the range was far, far more than I had expected and I stood bewildered in front of the display. I must have looked lost because, after a while, one of the assistants came over.

"Can I help?"

"I'm just trying to...." Trying to what? What on earth was I going to say?

"What sort of skin type does she have?"

"Err.... Pretty much the same as me."

She gave me a long, long look.

"This is for you, isn't it?"

I guess my blushes were answer enough.

"Don't worry, I'm cool with it. I think you'd look great in make up. What sort of look are you after?"

"A... a bit tarty. How did you guess?"

"You're the guy who was in here buying all that hair removal stuff the other week. And then, come Saturday, you're back buying nail varnish remover. And now you're all in a tizz in front of the makeup counter. You don't have to be Sherlock Holmes to work that one out."

"No, I guess not. So, Kaylee," I said, reading her name from her badge, "what do you suggest?"

Kaylee was really nice and ever so helpful. I still ended up spending a fortune but at least it all went together and she gave me the basics of how to put it on.

"So, what's your name," she asked as she helped me choose mascara.

"Ben."

"No, silly, not that name, what's her name?"

"Oh, I see what you mean. She's Belinda."

"And does Belinda have someone special in her life or is this all just for you."

"Belinda... Belinda has a boyfriend," I lied. Did I, or even Belinda, have a boyfriend? Not in the slightest, but Kaylee seemed to be coming on to me and that felt like the easiest way to get out of it. The last thing I needed was to get her involved.

"All the best ones are gay," she laughed. "Now, that's about all you need for now. Come on, I'll run this lot through the till and, if you find you've forgotten anything, then come straight back and ask for me. I'm here most days. OK?"

That night I had my first three attempts at putting on the makeup. I used quite a bit of it, not to mention the amount of makeup remover I used as I took it off again afterwards. I was also fast finding out why dressing rooms have those big mirrors surrounded by lights. The single ceiling light in my room was nowhere near bright enough for this sort of thing and I ended up having to give it a rest for the night. I gave my face one more thorough wash and headed for the bar. After that lot I needed a couple of pints.

On Tuesday, as soon as my lectures were over, I set out to find the shoe shop that Tracy had recommended. When I got there it looked like any other shoe shop and there were plenty of 'normal' customers browsing the stock. However, as soon as I mentioned that I was the one who had phoned, the one recommended by Tracy, they took me through to the back room where I could try on shoes to my heart's content without having to worry about privacy.

What's more I could discuss my exact needs without embarrassment. The saleswoman had seen it all before and quite understood the problems such as scuffed toes from kneeling. Her main suggestion was to slip them off before I got down on my knees but, apart from that, she showed me a number of styles, mostly open toed, that would be more resistant to scratching.

"But I'm supposed to be a schoolgirl," I protested.

"Honey, if the shoes are sexy enough, no one's going to give a damn. After all, how many schoolgirls wear heels in the first place?"

Once again, I had found myself a helpful assistant. What's more, she was able to find me the perfect fit which made walking so much easier. I ended up with two pairs, both in black leather, both open toed, both with four inch heels and both gorgeous. At four inches the heels were a compromise between sexiness and practicality. After all, I had to dance in them and then parade around afterwards. The bill came to the thick end of two hundred quid and I am lucky I have small enough feet to fit into women's sizes or it would have been more. Even so, it was worth it. I just hoped I could keep the shoes looking presentable for more than one show otherwise this would be a major drain on my income.

On my way home I picked up a makeup mirror, one with lights. It was a good job I was earning so much. I seemed to be doing nothing but shopping.

When I got back to my room I had another go with the makeup. The mirror was a great help and I was getting better, still not perfect but much better. But once I had the make up on I didn't want to stop there. I had two new pairs of shoes that I was just itching to try on and I had to become Belinda before I could really see how they went with the rest of the outfit. I put on the wig and that really helped with the transformation; I was far less Ben dressed as a girl than Belinda with rather sloppy makeup.

Then I stripped off down to my panties and went over to my wardrobe. The Belinda Bombshell costume was hung there, washed, ironed and ready. I put on the skirt and blouse and, finally, stepped into one of the new pairs of shoes. I stood in front of the mirror, looking at myself with a critical eye. Now it was complete it was even better than I had thought. I might even pass muster come Saturday night, just, but there was plenty of room for improvement and I would do well to practice some more. Furthermore, it was quite clear that the pale lavender panties I happened to be wearing that day didn't go with the tartan mini-skirt and, if I was to wear open toed shoes then I would also have to wear nail varnish on my toes. Indeed, if I were to go the whole hog, then the bare midriff look could also be enhanced with a belly button piercing.

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byChestersBoi© 6 comments/ 10484 views/ 1 favorites

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