Pony Boy Ch. 09

The story so far...

Ben, desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amount of groping' he has found that this led, inexorably, to a life as a prostitute. Moreover, Andy Mason, his pimp, along with Archie, Mr Mason's enforcer, has made it quite clear that, as long as there is money to be made from renting him out, quitting is not an option.

One of the many indignities Ben has been forced into is performing in a sex show where, cross dressed as naughty schoolgirl "Belinda Bombshell", he is caned and sodomised for the entertainment of the punters. The show, and Belinda in particular, is such a hit that Mr Mason has seen yet another money making opportunity and he is keen that Ben should perform as Belinda as much as possible. But, more than just the stage show, he is now looking to make even more money by renting Ben out as a transvestite escort.

But, for all Ben is finding this demeaning and degrading, he is also discovering sides to his sexuality that had previously lain hidden. He may loathe Belinda and all she stands for but that doesn't stop him getting a certain frisson of pleasure whenever he puts on her panties.

And, all the while, there's the complicating factor of his growing relationship with taciturn and secretive Jed, at first his arch rival but, latterly, his lover.

And now there's a new kid in town. Jack, racing as Little Angel, who has been recruited as a ponyboy and is being drawn in further using exactly the same tricks that they used on Ben. And while Ben is sympathetic, Archie has warned him not to do anything that would hinder Little Angel's 'training'.

Now read on...

As ever, after the post-race parties, I had just enough time to get home and get changed before heading off down to the gym. I was completely exhausted from the pony races and the party but it wasn't just the threats from Mr Mason and Archie that made sure I attended. Now that I had real competition in the racing I was anxious to keep up my fitness levels. Crazy as it seems, despite all the other stuff that went down, I was still keen to be top pony, still keen to show this newcomer that he couldn't have it all his own way.

I was busy on the treadmill when Mr Mason arrived. He came over and leant on the handlebars so he was standing next to me. As ever he looked me up and down, an owner inspecting his goods. I reached for the off switch but he brushed my hand away.

"Good morning, Belinda. I've had a Mr Simmons on the phone singing your praises. A most satisfied customer. He tells me he definitely wants to book you next time he's in town."

"I'm glad to hear it," I replied rather breathlessly.

"Good, because judging by the hits we're getting on the website, he's not going to be the only one. This has all the hallmarks of really good little earner. Funny how many of the punters want a girlfriend who has that little bit extra." He reached down and cuddled my balls through my shorts. "Talking of which, how do you think young Jack would look in panties? Maybe we could sell the two of you as a sister act. Belinda and Jackie Bombshell. How about that for an idea?"

"I'm not sure he's ready for that yet."

"Sure, but with a little bit of persuasion... After all, it didn't take much to turn you around. One moment you're a shy little virgin and the next you're the randiest little slut on my books. I dare say you'd turn tricks for free if I didn't give you paying customers. In the meanwhile young Jackie boy has certainly spiced up the pony races; given you some real competition rather than the broken down crocks you're used to racing against. I think I'm going to have to recruit more college students, help them pay off their student loans. What do you think?"

I just pounded away on the treadmill. I knew better than to rise to Mr Mason's bating.

"But I'm not just here to chew the fat. I've got a nice little Belinda date for you tonight. Car pick-up at seven thirty; I think you ought to wear that blue Chinese number. And then, tomorrow, I've got you and Jed doing the naughty schoolgirl routine for Billy Jenkins's birthday party. Car pick-up at seven. I'd like to see you trying out the new gymslip for that one. I'm still waiting on confirmation for a booking on Sunday but it's looking hopeful so don't make any plans."

"Mr Mason..."

"Yes, sonny?"

"About Easter."

"What about Easter?"

"My parents... they're expecting me home Easter Sunday."

"Well, they can just bloody well expect then, can't they. I'm not paying you good money to be swanning off whenever you feel like it. You go where I say and when I say it. Do I make myself quite clear?"

"Yes, Mr Mason."

Jed had warned me but it was still dispiriting to hear Mr Mason say it. If ever there was confirmation that I was now his property it was this.

That rather put a damper on things and, even after sleeping for most of the day, I still felt listless and dispirited. However, as I showered and shaved ready to go out as Belinda, I knew I had to pin on a happy face. The customer expected me to be upbeat and willing and I knew that if even the slightest hint of a complaint got back to Mr Mason then he would take it out on me.

As I sat at my dressing table, applying my make-up, I thought over what he had said about how I would turn tricks for free if he didn't supply me with customers. While this was a gross exaggeration there was just enough truth in there to make it hurt. Whilst I had learnt to loath Belinda and all she stood for that didn't stop the fact that I did, genuinely, get a thrill from cross dressing. I now wore panties all the time and felt happier for doing so. But I wanted to do it for me, and, hopefully, someday for that someone special I dreamed of having in my life, and not for the sleazeballs who hired my services.

And, on a wider note, there was no doubt now that I was both gay and a 'bottom'; I thrilled to being taken by a big strong man. At the start I had, genuinely, been turned on by my 'walk on the wild side' and found a perverse kick from being fucked by my customers. However, as abuse followed abuse, I had quickly found that there is a profound difference between a rape fantasy and actually being raped. And just because my prick was hard it didn't mean my soul wasn't being despoiled.

By now the face in the mirror was all but done. I plucked one or two stray hairs from my eyebrows making them thin and feminine. I'd baulked from this at first but now that my contact with college was minimal there was no need to hide anymore. I slipped on the wig and there she was, staring back at me, Belinda, the slut. Still, the make-up was a wall to hide behind. It wasn't me in the mirror, it was Belinda and I hoped that, dressed like this. no one would see past her to find Ben, or even Belle.

I put on the Chinese dress and shoes to match. Then I packed my bits and pieces in my clutch bag and put it, along with the baby-doll, in my shoulder bag. I was ready.

Again it was a hotel gig and, again, I was supposed to meet the punter in the bar. I was dropped right outside the front door and, out of interest, after I had gone two or three steps, I turned back towards the car and saw the driver busy working away at his mobile. It looked like my guess about him texting the punter was correct. This, hopefully, meant that I wouldn't be alone for long. Although my confidence was rapidly growing it wasn't too hard to guess what I was and that alone marked me out as trouble.

"Excuse me, miss. Are you a resident here?"

"Not exactly. I've got an appointment to meet one of your residents, a Mr Higgins, in the bar. Perhaps you can show me the way."

"Not so fast, darling." The doorman, quietly but insistently, led me to a quiet corner of the lobby. "This is a respectable hotel and we don't need your sort, even if you have got an 'appointment'. Now, are you going to fuck off quietly or do I have to throw you out?"

I thought fast. This was all about to go horribly wrong. I could only begin to imagine the trouble I would be in if I failed to make the appointment. There was one thing I could try. I opened up my shoulder bag and, within that, my clutch bag.

"Maybe this would help?" I said as I fished out a couple of twenties.

"Make it sixty."

Thanking my lucky stars that I had taken plenty of taxi money I fished out yet another twenty. The doorman disappeared the notes and I was through. As I crossed the lobby I saw the receptionist look up and glance at the doorman. Knowing what to look for I saw the exchange of glances and I guessed that the receptionist was in for her cut.

Fortunately the barman didn't seem to object to my presence. Maybe the doorman's take was cut three ways. Anyway it wasn't long before I was sat at the bar nursing a white wine and soda and feeling incredibly conspicuous. The doorman, the receptionist and probably the barman knew exactly what I was and I felt as if I should have a credit card reader dangling from my wrist.

After a couple of minutes a middle aged man entered the bar, took one look around, and headed straight for me.

"Excuse me, miss. Can I buy you a drink?"

"Mr Higgins?"

"Higgins, no, sorry love. Percival, Jim Percival. Still, never mind, why don't I keep you company until this Mr Higgins arrives."

"I really don't think that's a good idea..."

"Come on, darling, don't be shy. I'll show you a far better time than this Higgins guy would. I wouldn't have left you sitting at the bar, for a start." His hand reached around my waist.

"Please, leave me alone!"

"Don't be like that. Come on, now, be a good girl..."

"Excuse me miss, there's a gentleman here asking for Belinda. Is that you?" the barman cut in.

I nodded.

"The young man down at the end."

I looked down the bar and there, at the far end, was a guy of my age or maybe a year or two older looking rather gormless.

"I believe my date has arrived," I told Jim Percival rather pointedly.

"What would you want with a jerk like that?"

"Mr Percival, please stop pestering me."

"Is this gentleman bothering you?" the barman asked.

Mr Percival's face turned hard but he could see he was beaten. "Fuck you bitch. I hope you get AIDSs and die," he snarled but at least he left.

I smiled and waved my fingers at the guy at the end of the bar and he came on over.

"Are you Belinda?"

"I am, and you must be Mr Higgins."

"Rodney, please."

"I can't say how delighted I am to meet you."

"Was that guy giving you a hard time?"

"Let's not talk about him. Let's talk about you. Why don't you get yourself a drink and we'll find somewhere to talk."

"Actually I'm not the one you've come to meet; I'm just the messenger come down to fetch you. The guys are all waiting upstairs."

"The guys?" My heart sank as I had visions of some sort of gang-bang.

"Come on, you'll love them."

I followed Rodney to the lift which whisked us up to one of the higher floors. Meanwhile he turned to me and started to explain.

"Look, today is Julian's twenty fifth birthday and, as he's a bit shy with the girls, we thought we'd get him a surprise; something a bit... different."

"And I'm it?"

"And you're it. Look, I've booked the two of you a table at Leonardo's so Harry, Tarquin and I will get you started and then we'll fade away and leave you to show him a good time. I sorted it out with your head office for the full overnight package so you don't have to rush anything."

"If I'm a surprise...," I wasn't sure exactly how to put this. "Do you know exactly what I am?"

"Yeah, sure, I'm the one who made the booking."

"And when Julian finds out. I mean, he'll have to eventually..."

"That's the surprise."

This had disaster written all over it but, as ever, I couldn't back out. I followed Rodney down the corridor to a suite of rooms where his friends were waiting. They were all sat in armchairs in the main body of the suite and, through an open door, I could see the bedroom beyond. There were a couple of empty champagne bottles on the coffee table which suggested that they were already a little tipsy. Like Rodney they were all hooray Henries which put my hackles up but I wasn't being paid for social commentary. I was, as Rodney had put it, the surprise birthday present.

"Hey, chaps. This is Belinda."

"Hi guys," I chirped. "And which one of you is the birthday boy?"

"The gormless one down at the end. Go on, Jules, say hello to the lady."

"Hello, Belinda."

"Let me give you a great big birthday kiss."

I went over to where he was sat and kissed him full on the lips.

"Wow! You're a bit of a smasher!"

"Thank you. You're not so bad yourself. Oh, there's nowhere to sit. Can I squeeze in next to you?"

I'm not sure how much it was because Jules was a little drunk or because he was not the sharpest knife in the box but he seemed to be falling for it hook, line and sinker. Rodney poured me a glass of champagne and for a few minutes we just chatted. I flirted with Jules, putting my hand on his knee and sliding it north and, judging by his reaction, he was loving it. Then Rodney announced the second part of Jules' present.

"The thing is, Jules, we've booked you and this young lady in at Leonardo's. Dinner is at eight thirty so you'll need to get your skates on."

"Wow, fellows, you are the tops. And you, Belinda, would you do me the honour of accompanying me to dinner."

"I'd be delighted."

Jules missed it but I could see the mischievous delight in the eyes of his friends as they set him up. Tarquin organised a cab for us and the three of them went downstairs with us to see us off.

Jules was an absolute gentleman. He held doors for me, he took my arm, he treated me like a princess. After all the abuse this was wonderful and I found myself responding. I saw the eyes of the Maitre d' at Leonardo's give a bit of a flicker when he saw me but I guessed that money talks and he wasn't going to say anything while I was on Jules' arm.

The meal was superb, and not just the food. While he was never going to be troubling Mensa, Jules was charming, witty and had superb manners. More and more I found myself warming to him and, more and more, I was dreading the reveal, the moment when he found out exactly what was underneath my dress. As such I spun the meal out as long as possible and it was quite late before we were sat together in a taxi heading back to his hotel.

"Belinda?"

"Yes, Jules?"

"You're a smashing girl, really you are. I'd... I'd... I'd love it if you would come up to my room for a little drink... if you'd like... you don't have to."

"Oh, Jules, you're such a sweetie. Of course I will. I don't want this evening to ever stop."

We made our way upstairs and back to the room. The maids must have been because the empty champagne bottles were cleared away and the room was spotless. I found my shoulder bag which I had left there and did the old 'slip into something more comfortable' routine. I went through to the bedroom area and got myself ready, changing into my baby-doll and lubing up. Then I slipped under the covers and called out softly, "Jules, I'm ready for you."

As he came into the bedroom he had the most wonderful smile. He really thought this was the best thing ever. My heart was in my throat. As soon as he got in with me all pretence would be gone. I watched as he got undressed and then he slipped in beside me.

"You're very beautiful, do you know that?"

"You're very kind to say that."

"No really you are."

And then he kissed me, a kiss that went on and on and on. And, as we kissed, his hands started to wander. Surely he must know by now, surely... His hand traced a line up my thigh, all the way up my thigh, all the way until...

I felt his hand brush, almost as if accidentally, across my prick. I couldn't help but let out a little gasp.

"You like that?" This time there was no accident about it, this time he really was stroking my prick through the panties of my baby-doll.

"Oh, Jules!" I sighed and not just from the physical pleasure. He knew I had a prick and he didn't seem to mind. I felt as if a huge weight had slipped from my shoulders. Now I could relax, now I could give Jules the night he deserved.

Jules turned out to be as much of a gentleman between the sheets as he had been in the restaurant. He was kind, considerate and caring and, despite having had one or two glasses of champagne too many, he was also virile.

If anything he was too considerate. When the time came to slip inside me he was almost too gentle. I was far too used to being raped and even Jed was forceful. Jules, on the other hand, was all but apologetic, concerned that he might hurt me. I pushed back so as to encourage him but he still didn't quite get the message.

"Please, Jules, darling. Take me, take me hard. I'm not made of glass. Oh, yes, like that. Harder, please, harder, oh Jules... oh Jules..."

And then, when it was all over, we had a kiss and cuddle and he told me he'd known right from the start exactly what I was.

"After all," he commented. "I know I'm a bit of a fool but I'm not a complete idiot."

"And you didn't mind?"

"Why should I mind? I've had a great time. You're a smashing girl, Belinda and the best birthday present ever."

"And you're pretty special too. Now, why don't you roll over onto your back and I'll show you how special."

And it was quite late before we had worn each other out.

Come the morning and Jules was keen that I should go down to breakfast with him. The thought of appearing in the hotel restaurant as Belinda didn't appeal so I made my excuses and slipped into the en-suite to get dressed and ready to depart.

Jules was all over me when I emerged and it was quite hard for me to leave. When I finally persuaded him I had to go he pressed an envelope into my hand.

"I can't take this." Was I really turning down money? The problem was that Jules had been so nice, so kind, my protestation had slipped out without me thinking about it.

"Of course you can. Please. It's my way of saying thank you for the best night ever."

And he wouldn't take no for an answer. As I made my way down in the lift I remembered what Mr Mason had said about how I would pull tricks for free. Well, no, I wouldn't but if they were all like Jules... I sighed deeply and went out into the street to catch a taxi home.

If Friday night was a trick I would, almost, have done for free then Saturday night was a rude re-awakening to the ones I really wished I didn't have to do at all.

Billy Jenkins' birthday party was held in yet another of the seedy private clubs I was getting to know far too well. This time I was dropped off not in front of a posh hotel but in a reeking alleyway full of industrial waste bins. I picked my way through the spilt garbage to the back door where I was led through the kitchens to the 'dressing room'. The whole 'backstage' area was dim, filthy dirty and smelled of things I'd rather not know about. The dressing room itself had seen better days. A sofa with broken springs, a cracked mirror where half the bulbs were blown, the toilet with a missing seat. Hardly conducive to getting changed.

And then, as I put on the make-up and fitted the wig, there was the knowledge that I was turning into something I was growing to despise. Oh, at first, there had been the excitement of a bit of rough sex, of stepping outside the norm. There was a thrill to be had from breaking all the rules, from challenging the morality I had been brought up with. Now, with the illusions being stripped away, it was getting harder and harder to keep up the pretence. What I was about to do would be cheap and degrading, and there would be worse to follow.