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.
