Pony Boy Ch. 05

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Be my guest."

I felt the straps around my penis being undone and firm fingers gripped my erection.

"He certainly seems quite eager." The fingers were now pumping me and my prick felt as if it would explode.

"Oh, I think you'll find he's very eager," Mr. Mason replied.

"I can hardly wait. Now, you said I could try taking him for a ride."

"Certainly. Pete, would you get College Boy ready for Mr. Hastings?"

This was a turn up for the books; the first time I had heard of a punter being allowed to drive a pony. Mr Hastings must have real clout. I felt the sulky behind me give a jerk, one more cumbersome than when Pete got on, and then I felt the straps holding my prick being refastened and my hobble being removed. Almost immediately I felt a massive tug on the reins which made my head jerk back and the bit dig into the side of my mouth. Although the bit acted as a sort of gag it couldn't suppress the cry of half surprise, half pain that this forced out of me.

"Easy, Mr. Hastings," Pete called out. "Softly, softly, that's the way with ponies. Now, let me walk him round for you."

Pete took hold of the reins just by the end of my bit and, still blindfolded by the blinkers, he led me forward. Seeing as how this Mr Hastings had such clout it was up to me to put on the best show I could. I made sure I stood up straight and made myself look as good as possible. All around I could hear the hustle and bustle of the centre circle and the excitement of a race in progress. However, I could feel from the way that Mr. Hastings was pulling on the reins that this was not enough for him. He really wanted to have me run and, in the end, that was what happened.

I guess Mr. Mason must have organised it because they waited until the current race was over and then Pete led me to the entry to the course proper and opened up my blinkers.

"One lap, not too fast and, for heaven's sake, don't tip him over," he whispered in my ear. He let go of my bridle and, with a flick of the reins, Mr. Hastings urged me out onto the course. He was a lot heavier and clumsier than Pete so I jogged rather than ran around the course but, even so, judging by the way he was jiggling the reined, Mr. Hastings was loving every second. I just wished that he wouldn't pull quite so hard; at least he didn't have a whip. I was also glad it was just the one lap before I could return to the centre circle where Mr. Hastings dismounted and Pete parked me up again.

After that Mr. Hastings disappeared with Mr. Mason and, for all that he had stroked my prick and I had run him around the course, I still hadn't set eyes on him. Indeed, apart from the fact that he was heavy, a little clumsy with the reins and seemed to enjoy being pulled around the course I knew next to nothing about him.

However, I didn't have too much time to wonder. With Mr Hastings out of the way I was called upon for three of the ad hoc races and, on each occasion, they were handicapped. I managed to win two of them but came second in the middle one, much to Mr H's delight.

Eventually the racing was all over and, as the punters drifted off, we ponies were sent to the showers to get ready for the party. I could feel the tension within me rising. I was evidently going to have to entertain Mr. Hastings and, as yet, I knew nothing of his likes and dislikes. Although I should have been getting used to this I was increasingly apprehensive; Perhaps I was apprehensive because I was getting used to it. Still, there was absolutely nothing I could do to get out of it and it was in my best interests to make myself as agreeable as possible. It was time, once again, to become the randy little tart.

While we were showering Jed came up to me and was all 'when are you going to suck my dick, then?' but, when he got close, he grabbed me round the neck and started wrestling me. I was wondering what had got into him when, under cover of this, he whispered urgently 'You've got Mr. Hastings, right? Use lube, lots of lube' just before the minibus driver told him to stop mucking about and leave me alone. I wondered what he was on about but it didn't bode well and I certainly wasn't going to ignore him. I made the excuse of wanting the bogs and, on the way, I grabbed a bottle of the lube they used for fitting the tails and made sure plenty of it was inside me.

With all this going on I was shivering as I got into the minibus to take us to the party. Of course, this could have been because, wearing only the shortest of silken shorts, it was a little chilly but I would be lying if I said that that was the only reason.

When we got there I was taken straight to where Mr. Hastings was being feted by, among others, Mr. Mason. As I had guessed from when I had pulled him around the track he was a big man, well over six foot and built like a boxer. But it was the look in his eyes that got to me. They were cold, steely, unfeeling. He was having fun at the party but there was no joy there, none whatsoever. He was obviously some sort of celebrity and I suppose I should have been honoured to be the one chosen to entertain him. He had me sit down beside him and I was handed a glass of champagne.

"You look very sweet," he said to me.

"Why thank you," I replied.

"And yet Mr. Mason tells me that you're a horny little sex pot who will do anything for a bit of cock. Is that right?"

"I couldn't say, sir."

"Oh, I think you could. Mad for it, aren't you?"

"Yes, sir," I admitted, batting my eyelashes at him. It looked like he wanted me to play the whore so that was what I did.

"So, what do you like best?"

"I like big strong men like you."

"Do you, indeed. And what do you like big strong men to do to you?"

"Whatever you want, sir, whatever you want."

"Whatever I want, as long is it involves cock, eh?"

"Ooh, yes please sir." But I felt as if I were reading from a script. I just wanted to say and do whatever it took to keep the customer satisfied.

"You're right, Andy," Mr. Hastings said to Mr. Mason, "this one looks like butter wouldn't melt and talks all posh and everything but she's mad for it, just like you said."

"Wait till you see the video. Here, check this out."

Mr. Mason reached for a remote and a huge television that hung on the wall burst into life. He then pressed a few more buttons and I was a little shaken to see the stage at the club where Mr. Bothwick's party had been held. The music started and there, up on the screen, were Jed and I, doing our act. While Jed and I had done this again and again and again in rehearsal I had never actually seen how I looked. I always knew that Belinda Bombshell was a little tart but I had never realised just how much of one. I watched myself camp it up in silent horror.

Mind you, Mr. Hastings, and all the crew, were loving it. The more outrageous I became the more they whooped and cheered. I got lots of comments when I was bent over with Jed caning my backside and when we got to the bit where Jed was fucking me they couldn't get enough. I knew I had played Belinda Bombshell to the hilt, what I hadn't fully appreciated was exactly how much of a cheap whore she was.

And, when it was over, I may not have been in costume but I was still expected to be Belinda Bombshell, I was still expected to still be that cheap whore. After all, I had offered myself up to do anything Mr. Hastings wanted; wasn't that the action of a cheap whore? But there was no backing out now. I had been bought and sold, I had to play this one to the end.

"Oh, you do like cock, don't you? Can't get enough of it. I bet you can't wait to get one up you."

I just tried a bashful look but Mr. Hastings wasn't having any of it.

"I asked you a question, cunt, do you like cock or don't you?"

"Ooh, I love a big strong cock," I simpered.

"I bet you do. Do you see Gaz over there," he pointed to one of the guys. "Go over and ask him if he's got a big strong cock."

'Here we go,' I thought to myself as I slipped off the sofa and went to stand in front of Gaz who looked up at me.

"Please, Mr Gaz, sir, have you got a big strong cock?"

"And what's it to you if I have?"

"Because I love a bit of cock. There's nothing gets me going like a big strong stiff one." This, at least, got a round of laughter.

I could see that Gaz was a little uncertain and he kept glancing towards Mr. Hastings but, after a moment or two he undid his flies and pulled out his prick. It was still pretty flaccid.

"Ooh, that's a nice one You have got a big strong cock. Shall I see if I can make it a little stiffer for you." I knelt down in front of him and took his prick in my hands, gently stroking it, feeling it growing, feeling it come to life.

"That's nice, Mr Gaz. I bet you can please all the girls with a cock like that. Let's put his little coat on and then we can play properly." I reached behind me for the bowl of condoms on the coffee table and, with a movement that I was getting all too practiced at, opened up the packet, took out the condom and slipped it over him.

"Go on, Gaz, let's see you fuck the little tart," Mr. Hastings called over.

"Yes, please, Mr Gaz, please fuck me." This was obviously what Mr. Hastings was after; this was how I was to earn my money. I now understood why Jed had urged me to get lubed up.

"Here, this will help," Mr. Mason added.

With my hand still around Gaz's prick I turned to see what would help and, as I did so my heart sunk. Under Mr. Mason's instructions, two waitresses were bringing over a black leather pouffe. But it wasn't that which disturbed me, it was the straps that were attached at either side. I wasn't just to be bent over it, I was to be strapped down as well. The coffee table was moved to one side, the pouffe was placed in the middle of the group, I was positioned over it and the straps were tightened, holding my upper arms and thighs in place.

I felt Gaz kneel down on the floor behind me and, with a vicious tug, he ripped away the flimsy material of my shorts.

"Look at me," Mr. Hastings ordered and, although I had to crane my neck, as Gaz forced his way inside, that was what I did. Now I knew exactly what he was after. Just like Mr. Bothwick he wanted to see me degraded, he wanted to watch me suffer. I was the fly from which he had torn off the wings and now he wanted to see me squirm.

He certainly got his money's worth. It wasn't just that Gaz was far from gentle. I had reached the point where all delusion had been stripped away. I wasn't just playing the cheap whore, that was exactly what I was and my complete and utter degradation was now a performance for Mr. Hastings's amusement.

It didn't take long before Gaz had finished but that didn't mean that I was finished, far from. The others took their turn, either voluntarily or on Mr. Hastings's suggestion, a suggestion that was obviously taken as an order. It wasn't constant but the breaks between were never really long enough and it just went on and on and on. Fucking the tart was now just another amusement for them, along with the lines of coke and glasses of champagne. It didn't take long before I was pretty sore but that didn't stop them, why would it? Furthermore it seemed that, although he wanted to watch me suffer, my cries of pain were deemed distracting so I was fitted with a ball gag to keep me quiet.

And all the while Mr. Hastings just watched.

At last it was over, the party was breaking up and people were drifting off. Just as Mr. Jarman had done Mr Hastings told his lads to go on ahead and he would catch them up. He waited until we were alone before standing up and unbuttoned his fly. I assumed that he was going to fuck me as well but no, he stood over me, masturbating.

"Look up, tart, look up."

With his free hand he grabbed me by the hair and yanked my head back just in time for the great gobbets of semen that erupted from him to splash all over my face. Finally sated he let me go and my head dropped; I felt used, humiliated, crushed.

"Come on Sam, the car's waiting," Mr. Mason called out.

"On my way, Andy, on my way."

And, with that, he left.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
KatBalluKatBalluover 10 years ago
Please Write More

I really enjoy this story. Please continue the saga.

AnonymousAnonymousalmost 11 years ago
plz

next chapter.... plz sir...

AnonymousAnonymousalmost 11 years ago
Hurry the HELL up!

Sorry if that sounded a touch rude.

hehe

I'm just really enjoying your story. I'm anxious to find out whats next.

AnonymousAnonymousalmost 11 years ago
I Love Belinda!

I know that the crossdressing thing kind of came out of left field for most readers. Though it's not a major kink of mine, I am really enjoying it's role in this story. I think it was important for Ben to tell us all about his efforts in feminizing himself because it is clearly something that he finds exciting and erotic, separate from the act he is being forced to play as Mr Mason's gigolo.

I am also enjoying the frenemy/sexual tension situation between Ben and Jed and hope they go the distance. The bit in the previous chapter where Jed was lubing/fingering Ben before their show was definitely the hottest of the story so far!

chesthairslavechesthairslavealmost 11 years ago
Pony Boy Races 6 points, Belinda 3 points, Mr. Mason becoming a Dickhead 0 points

Overall I like the story series. I thought this chapter had way too much talk about Belinda dressing, makeup, and especially the payment of the items. Actually was bored a few times. The new circle pony race was exciting because everything was unknown to the reader about what was happening. Look forward to your next chapter. Will Jed's warning of being trapped become true?

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Steam Room Daddy A young straight guy is forced to obey him.in Gay Male
First Time with Neighbor Daddy 18-year-old boy is taken by older neighbor.in Gay Male
How I Became A Gay Cock Slut Young married man is seduced at a resort.in Gay Male
Straight Turnout Strait guy is turned out by an experienced man.in Gay Male
Boyfriend Gets It in the End She convinces boyfriend to try out his hung friend.in Gay Male
More Stories