Pony Boy Ch. 08

"That's not what Mr Mason says. Eight o'clock and no fuck ups."

And with that the phone went dead.

I rushed home and, with the kebab now lying heavy on my stomach, started getting ready as Belinda. A quick shower and shave made a start and then I put on a pair of black lacy panties to get me in the mood.

As for the make up, it wasn't exactly second nature but I was getting more adept and it didn't take too long before I was slipping on the wig and staring Belinda in the face. She would do, she would have to do. Then it was time for the clothes I started with stockings and a suspender belt to hold them up before wriggling into the LBD. I then stepped into my open toed sandals with the four inch heel and looked at myself in the mirror.

Would I pass muster? All I could see were the glaring imperfections. However good the make-up there was no getting away from the fact that I was, so obviously, a boy in a dress. Going out with Tracy to the pub across the road was one thing. I had no idea where this assignation would take me. I walked back and forth. I was getting used to heels and could walk quite smoothly in them. If only I had tits. Still, it was too late now to do anything about it. I would have to do the best with what I had.

I didn't have a jacket so I didn't have any useful pockets but, for the first time in my life, I had a handbag. It wasn't particularly big but condoms, lube, my makeup repair kit and a bit of spare change for the taxi home all fitted in just fine. Then I remembered what Tracy had said about the baby doll. I fetched it out along with the shoulder bag I had bought to keep it in. It looked a bit awkward but no more than the rest of the imperfections and I could live with it. I glanced at the clock. The car would be here in any minute but I was ready to go.

The driver took me into the West End and dropped me outside a rather posh hotel.

"You're to meet in the bar. Punter's name is Simmons."

"But..."

"Don't ask me, sunshine. I'm just the driver. You now know as much as I do. Go on, hop it. I've got other jobs waiting."

OK, this was the real test. Could I pass myself off as Belinda? One thing was for certain; I didn't have many other options and certainly none that let me avoid Archie's wrath. Trying my best to remain gracious I got out of the car and, feeling that the whole world was looking straight at me, made my way to the front door of the hotel. The doorman gave me a long cool look and I wasn't sure I could make it past him so, rather that try for discretion, I went for the up-front approach.

"Excuse me," I said, making my voice as feminine as possible. "I'm supposed to meet one of the guests here, a Mr Simmons, in the bar. Could you possibly point me in the right direction."

There was a pause while he decided whether to let me in or throw me out. I think the fact that I had given a name for the person I was meeting was the decider because he nodded his head and replied, "certainly, miss. Through the lobby and that door on the left."

Feeling as if his, and the receptionist's, eyes were following me every tottering step of the way I headed towards the bar. There I found the usual bored barman polishing glasses and keeping half an eye on the match on the telly. I looked around. The room was otherwise empty. I went up to the bar, dumped my shoulder bag on the floor and perched on a bar stool.

"Can I help you, miss?"

"A white wine and soda, if you'd be so kind."

"Are you a resident here."

"No, I'm meeting a friend."

"In which case..."

"Ah, Belinda! I've just received your text saying you'd arrived. I do hope you haven't been waiting long."

I looked to my side to see what had to be Mr Simmons bustling in. He guessed him to be around fifty, running to fat and more than a trifle bald and very much the business man. I hadn't sent any texts so my guess was that the driver texted him as soon as I had been dropped off and he must have come down immediately. Whichever, I was glad to be rescued from the suspicious mind of the barman whom, I'm sure, had sussed me for exactly what I was - in every sense of the word. He came up and we kissed cheeks.

"Good evening, sir. I was just getting this young lady a white wine and soda. What can I get for you?"

"Oh, a whiskey please. Is that Glenmorangie I see behind the bar."

"It is indeed."

While the barman poured our drinks Mr Simmons stood beside me and then, having put the drinks on his room tab, he suggested we find a quiet corner. He found a secluded alcove where he sat at one end of a sofa and I sat at the other. I tried to look demure and fluttered my eyelashes at him.

"So, Belinda, it's a pleasure to meet you."

"The pleasure's all mine, Mr Simmons."

"Please, you don't have to be so formal. You must call me Ray."

"Of course, Ray. Now tell me a bit about yourself. Are you a visitor here in London?"

It turned out that Ray was the manager of a carpeting firm from Bradford. I hung onto his every word and learnt far more than I needed to about the world of carpeting in Bradford and his favourite hobby, bowls.

Somewhere along the line we finished our drinks and he asked the barman to order him a taxi. And then we stood up and, with his arm around my waist, he led me out into the street.

This was far from the first time I had stepped out as a woman but, on each previous occasion, it had been as 'naughty schoolgirl' Belinda. This incarnation was something far grander and, as such, I was being treated with far more respect. This was Ray and Belinda, dressed to the nines, heading out for a night on the town. This actually helped reinforce the illusion and, as he opened the taxi door for me and helped me in, I felt one hundred percent a woman.

The restaurant was posh and discreet and all the tables were in quiet alcoves. I have no idea whether the Maitre d' sussed me or not but if he did he didn't show it and I was already beyond caring.

We sat side by side at the table and Ray had hardly ordered the celebratory bottle of champagne before I felt his hand on my knee. He even kept it there when the waiter came to take our orders. I had already eaten so I wasn't hungry but it fitted my feminine image to settle for a light salad while he went for the rump steak.

"Do you know, I've got a daughter just like you," he said as we came to the coffee and brandies. His hand returned to my knee and started to wander north.

"Really?" I smiled inside at the depth of his fantasy.

"Pretty little thing but can be quite a handful sometimes. Gets into all sorts of scrapes. When she's been naughty I have to be quite firm with her. I'm an old fashioned man and I believe in old fashioned remedies. She thinks she's all grown up but when she's been naughty there's nothing like an old fashioned over the knee spanking to put her back on the straight and narrow. What about you? Have you been a naughty girl?"

OK, so now we knew where the evening was heading. I had no idea whether this daughter of his was real or just another part of the fantasy but, right there, right then, my job was to take her place. I quickly made up some nonsense about a boyfriend who I had flirted with and who I had led on. All the while he demanded details and, all the while, his hand probed farther and farther up my thigh. I could sense his pleasure when he got to the top of my stocking and found my suspenders. I lowered my eyes and tried to look alluring.

"You have been a naughty girl, haven't you?"

"I'm sorry, daddy."

"Sorry is not good enough this time, is it?"

"Please, daddy, please punish me and make it better."

"Waiter, cheque please."

With almost indecent haste we were back at his hotel and going straight up to his room.

"Excuse me a moment. I'll just..." I inclined my head towards the en-suite.

"Don't be long."

I wasn't. It didn't take more than a moment to slip out of my clothes and hang them on the back of the door. Then I fetched out the baby-doll and put it on. I quickly checked my make-up in the mirror and, with everything looking fine, I took a condom from my bag and, discreetly palming it, returned to his suite.

Tracy had been spot about the baby-doll. Ray nearly came on the spot.

"Please, daddy, I've been a naughty girl. I need to be punished to make me behave better."

That, for him, was just the icing on the cake. He stood up and, grabbing me by the ear dragged me over to the bed. In moments I was across his knee, the back of my baby-doll was around my shoulders and my panties were around my knees.

He laid into me with some force. Oh, sure, it wasn't as painful as the caning I got from Jed but it wasn't love taps either. I squealed and squirmed, partially because that was what he wanted but partially because it did bloody well hurt. However, he gripped my wrist with his free hand and held it in the small of my back and, squirm as much as I wanted, I wasn't going anywhere.

And all the while I was pleading, begging, 'daddy' to punish me for being a naughty girl and to make me better.

When, finally, he had had enough he let go of my wrist and I slumped to the floor to kneel beside him.

"Are you better now? Will you behave in future?"

"Yes, daddy, I'll be a good little girl, honest I will."

"And are you grateful to daddy for making you better."

"Yes, daddy, thank you daddy."

"Then say thank you properly."

I didn't need to be told what came next. I reached for his fly, pulled down the zip and hauled out his prick. With the ease that comes from much practice I put the condom on and took him into my mouth.

And that was all he needed. I had hardly started when he gave an enormous groan and filled the condom. He grabbed my hair, or rather my wig, and pulled me down onto him so hard I was worried my wig would come off and then, after half a dozen thrusts, he collapsed back, exhausted and replete.

"That was... that was... that was fantastic," he panted.

"Thank you, daddy."

"No, thank you, Belinda."

There was a bit of an awkward silence. I wasn't sure what he wanted. I just remained knelt at the side of the bed waiting.

"You're a lovely girl, Belinda, but I think it's time you went," he said finally.

"I'll just..."

"Of course."

I got up off the floor and made my way to the en-suite. My mascara was a total disaster but, thanks to the bits and pieces in my bag, I was able to patch it all up and look presentable. Even so it must have been a good fifteen minutes before I re-emerged all dressed up and presentable.

"Thank you, daddy. I've had a super time," I went up and kissed him on the lips.

"I'll, err, call you a taxi. If you go and wait in the lobby it shouldn't be more than a minute or so."

"Thank you. I'll be off then."

"And this is for you."

He handed me a sealed envelope which I dropped in my shoulder bag. He seemed rather keen to be shot of me so I gave him one more peck on the cheek and left.

Standing in the lobby of the hotel waiting for the taxi I felt every inch exactly what I was: a transsexual prostitute who had just serviced her client. Her client? I guessed that, as long as I was dressed as Belinda, I would think of myself as Belinda. The night receptionist kept a close eye on me. She knew exactly what I was and was as keen to get rid of me as I was to go. Fortunately it wasn't long before the taxi arrived and, thank heavens, the driver wasn't one of the chatty ones. I sat gingerly in the back, my battered buttocks sore against the seats, and checked out the envelope. A nice round ton. At least 'daddy' tipped.

On Thursday I had nothing planned until the race meeting at seven thirty. I suppose I should have gone to some lectures but term was all but over and I wasn't sure how long my university career would last. Instead I took my clothes to the laundrette and dry cleaners as appropriate and, while out, dropped in on Mr H's office to collect my wages.

Of course, when I got there, Mr H reminded me that a large part of the money would be used to pay off the clothing bill. Even though I had clocked up four hours with the Embassy gig and three with Mr Simmons I still owed Mr H over four hundred pounds so there was only around two fifty in my pocket. Mind you, with Mr Simmons' tip and the Texan's generosity I wasn't exactly short.

That evening, as the minibus did its rounds, there was a new face among the ponies. When he got on he got the same hazing that I had got and, because I noticeably didn't join in, he came and sat next to me. To my jaundiced eye he looked incredibly young but, as he chatted away nervously, he let slip that, like me, he was at university which put him at eighteen or nineteen minimum.

"I won't have to do anything sexual, will I? Mr H said there would just be a certain amount of groping."

"You'll be OK," I assured him. OK, so I was lying through my teeth but the poor kid was nervous enough without knowing exactly what he was in for. And how was I to know? Maybe he would only be subjected to a little groping.

As we went through the pre-show showers I could see that his nerves, if anything, were getting worse. Jed sidled up to me.

"Recognise yourself?"

"Was I really that bad."

"Yep."

"I should warn him."

"No you shouldn't. He'll learn. Same as we all did. Look at you now. Right little tart. Mind you, he looks fit and he's a non smoker. You might find you have some competition for a change. My guess is that Mr Mason, seeing how much he's making out of you, is now aiming to recruit some more college kids."

I looked across at the new pony. He did look rather sweet. He was young and clean and had the cutest little arse. I could be sure the punters would go for him. Jed was right, I had some competition, I was no longer the new kid in town.

Jed's forecast that he would be a real contender in the races was backed up when Mr H did the seeding. It was clear that he was looking to get a final between the new kid and myself. The fact that, as far as the punters were concerned, Jed and I were still deadly rivals, was also taken into account but it wasn't long before we were all sorted out and taken out to our respective sulkies.

Fortunately I still had Pete as my jockey and, before he fitted me with my bridle, I asked what he thought of the new pony.

"Little Angel, that's what Mr H is calling him. Yeah, he's fast and he's fit but he's new and we can use that against him. You and I can take him, easy as pie. Now, open wide." He buckled the bit across my mouth and that ended the conversation.

We went through the ritual of putting on my harness and, when it came to inserting the plug, it just slipped in fine. I did hear a squeak of pain from across the warehouse. I guessed that Little Angel was finding what is was like to have a butt plug inserted for the first time. Part of me was sympathetic. The other part, like Jed, had a 'he'll learn' attitude.

He certainly caused a stir among the punters. There were the usual crowd who hung around me pre race but, even blindfolded, I could tell that there were fewer than usual and their main topic of conversation seemed to be comparing me with Little Angel, a comparison I didn't always come out best on. I know it was a bit childish of me but I was getting fed up of hearing about him. Jed's petulance at my first race meeting was much more understandable now.

I got through the first two heats fine and, without too many problems, defeated Jed in the semi finals. All the while I could hear that Little Angel was winning his heats and becoming more and more the fancied. Indeed, when we came to the final, he was the punter's favourite to win. That rankled.

We were led out to the start line, our blinkers were opened and the starter dropped his flag. We were off.

Almost immediately he pulled ahead. Bloody hell he was fast! I had to put in everything I had just to stay in touch. It was an eight lap race and I was prepared to wait my time but, unlike the others, he showed no sign of weakening, no sign of slowing. By the time we got to the seventh lap I knew I would have to dig deep.

But it was Pete who won the race for me. As we came to the last turn but three he gave that little flick of the reins that told me to go for the inside. I couldn't see the gap but I trusted Pete and, sure enough, as we went into the turn, Little Angel was going too fast and swung wide.

Using every ounce of my strength I forced my way through on the inside and, just, managed to keep the sulky upright. Now it was a matter of holding him off for a lap and a half. The crowd were going wild. This was a really tight race between two favourites and both ponies were carrying a lot of money.

I could tell from the frantic flicking of the reins that Little Angel was gaining on me and Pete was trying to squeeze out every last drop of my strength and endurance. I guess that, in the end, the gym sessions paid off because, despite Little Angel's best efforts, I managed to cross the line a couple of feet in front of him.

There were cheers for me and even a few boos for Little Angel as, triumphant, I was led back to the centre circle. I could tell that Mr H was delighted; he always was when the favourite falls. But more than that. We had put up a real spectacle. Even those who had lost money on Little Angel agreed that it had been a thrilling race.

I was given quite a while to recover while the other ponies were run in the ad-hoc races but I knew I would be called upon again. What I hadn't bargained on, although maybe I should have, was what I heard over the Tannoy.

"Ladies and gentlemen. We are proud to announce a special race. A rematch of the final between College Boy and Little Angel. Mr Mason has put up a special prize of two hundred pounds for the winner and, if that were not incentive enough, the loser will give the winner a blow job right here, in front of the judges table. This race will start in ten minutes so make sure to place your bets right away."

This took me back to my first time. It was an exact repeat of what had happened between Jed and myself. I wondered just how much the outcome would be determined by our racing and how much would be down to other factors.

In the end it was subtle but it was definitely fixed. Once again Little Angel got ahead early, once again I struggled to keep up but managed to keep in touch and, once again, I went for the inside on the third corner from home.

But this time, although at first I was getting 'go for the inside' messages from Pete, just as I had committed myself, I felt a tug on my reins telling me to go for the outside. That was enough to put me off and I missed my chance. And then, as we came to the second to last corner, again I got mixed signals. Someone, my guess would be Mr Mason, had got to Pete and, without his guidance, I was lost. Oh, sure, I tried my hardest but part of sulky racing is team work between pony and jockey and without that the best I could do was to come in a respectable second.

Now I fully understood how Jed had felt. Not only had I lost the race but my humiliation would be completed as I was publicly forced to go down on this... this upstart. I tried to bottle up my anger but with mixed results.

We were led to the centre circle and lined up facing each other in front of the judges tables. Little Angel's prick was unbuckled from his harness and fitted with a condom. I noted that he didn't seem to be quite so shy now.

And then, in front of everyone, I got down on my knees, the bit was removed from my bridle and sucked him off.

Sure, when compared to being sodomised for the Belinda Bombshell show this humiliation might not seem like much but, as a way of reinforcing that I had been well and truly beaten, it could not have been surpassed. The crowd around us were cheering, or rather jeering, and many who had felt that I had been too high and mighty by being 'party only' were glad to see my downfall.