Pony Boy Ch. 07

I nipped into the en-suite and, as I suspected, there was the complementary dressing gown hanging behind the door. As quick as I could I stripped off everything except my panties and put on the dressing gown. I slipped a couple of condoms and the lube into the pocket of the dressing gown and, after a quick check in the mirror, sashayed back into the room and, rather than returning to my chair, I picked up my orange juice and went and stood in front of him.

"There, that's better, a lot more comfortable. Would you like me to...."

"You're.... you're wearing nail varnish... on your toenails...."

"Do you like it?"

"God, that's sexy! Please, let me see. Please... please put your foot here." He opened his thighs and patted the edge of the armchair between them.

I put my foot up on the chair and moved it forward so that the tips of my toes were just tickling the bulge in his trousers. He immediately slid down the chair so that I was actively pressing against him.

"Do you mind if I...?" he asked as he reached down for my foot.

I just smiled as he took my foot in his hand and moved it so it was pushing against the length of his prick. He was breathing heavily and I wondered if he was about to come. He pushed harder, rubbing my foot against him but this just meant that I almost lost my balance. I stepped back and took a long hard look at him.

My job was to give the customer what they wanted. So far this had almost entirely consisted of bending over and spreading my arse cheeks. By using my foot to wank himself off "Mr Smith" implied that he wanted something else entirely. Wanting me to effectively stand on his prick suggested that, for once, it would be me who was handing out the abuse. But I couldn't just assume. He was still the one who was paying, it was his wishes that had to be fulfilled at the end of the day. It was time to try a little experiment. I undid the dressing gown and stood with my hands on my hips, holding it open.

"Do you want my foot back on your prick?"

"Yes, yes please."

"Then I think you're a little overdressed," I said making my voice as harsh as possible. "And what are you doing in that chair. You should be on your knees on the floor, shouldn't you?"

"Yes, sir, sorry sir," he replied slipping off the char and onto the floor where he started to feverishly tear at his clothes.

There was no doubt now. Even if he hadn't called me 'sir' the way he was grovelling on the floor in front of me said all I needed to know.

"Hurry up, I haven't got all night, and look at the mess you're making. You're pathetic, truly pathetic, do you know that."

He lost a couple of buttons off his shirt in his hurry and, as he pushed his trousers down, the bulge in his briefs made it more than apparent that I had read this right. It wasn't long before he was naked and on his knees, his rigid prick standing out in front of him. As I kicked away his clothes to the corners of the room I ordered him to kneel up straight and put his hands behind his head. Then, fetching a chair to use as a prop, I stood in front of him and reached out to prod at his prick with my toes. I remembered being bullied by a gym teacher at school and decided to take a few leaves from his book.

"Someone's a little overexcited, aren't they?"

"Yes, yes Sir."

"You're a dirty little pervert. What are you?"

"A dirty little.... a dirty little pervert sir."

"And what should I do with you? Would you like me to tread on you?"

"Yes, yes please."

"Oh, I think you can ask nicer than that. Try again"

"Please, please sir, would you be kind enough to tread on this dirty little pervert. Treat him like the doormat he is. Please, sir."

"And why should I do that?"

"Please, please, I beg you!"

His prick was, if anything, harder than ever. I seemed to have stumbled on some inner need of his, a desire long suppressed. I put my foot against his shoulder and pushed him backwards, not too hard but enough to make him fall. I pushed him with my foot until he was lying on his back and then put my foot over his face. Eagerly she started to lick.

"Did I tell you you could lick my foot."

"No, Sir. Sorry sir."

"Now I've got your slobber all over it. How disgusting! I need to wipe it off on my doormat. Are you my doormat?"

"Yes, sir, please use me as your doormat."

I wiped my foot back and forth across his chest getting ever nearer to his prick which hadn't softened in the slightest. I ended up, however, moving the chair, pushing his legs apart with my foot and standing between them so that, in this position, I could lay my foot along the length of his prick.

"Oh, god!" he groaned as I pushed rhythmically against it. "Oh, god, oh god, oh, please, harder, please, harder...."

Harder? I was all but standing on him, grinding the sole of my foot against his prick. And there was no doubt that this was working; he was pushing back at me, rubbing his prick against my foot as much as I was rubbing it against him.

"Oh, yes, please, a little more, just a little more, oh.... oh.... oohhhh!"

The spunk shot from him, great gobbets covering his chest. I moved back round to the side and used my foot to smear it all over him. From time to time I would move my foot to over his face and get him to lick it clean until, eventually, it was clear that he had had enough.

"That... that was fantastic. Thank you, thank you so much."

"Yeah, not so bad," I replied as I continued to wipe my foot on his pubic hairs. "But before we do anything else I think you need a shower."

"Will you... will you join me. Please, I'd like that."

"We'll have to see, won't we," I replied as I helped him to his feet. "Come along then." I led him into the en-suite and I ordered him into the shower. I stood back and watched as he adjusted the taps. Already he was getting hard again. The night was far from over.

And, ironically, although I was in control, although I was the one calling the shots, it was going to be quite a long night. I looked Paul over. He was as ordinary as they come and about as far as possible from the big, strong types that turned me on. Indeed, I was having to be his big strong man, a role that did not come naturally. Still, it was time to get back to work. I stepped out of my panties and joined him in the shower.

Immediately his hands were all over me. He seemed fascinated by my shaven body and he must have used half a bottle of shower gel as he used washing me down as an excuse to get a good feel. In particular, he kept coming back to my prick, soaping it and massaging it so that, under his ministrations, it was rock hard.

I returned the favour by reaching around and groping his arse. Almost inevitably, my finger ended up over his sphincter. He shuddered and moved in closer.

"Oh, you like that, don't you? You like me feeling up your arse."

"Yes, oh, yes," he replied breathlessly.

I took my hand away, poured out a big dollop of shower gel and, when I returned, smoothed the gel all over before pushing the tip of my forefinger into his arsehole.

"Oh, please," he gasped as I pushed my finger inside him. "Please, deeper, as deep as you can."

I pushed harder, managing to get my finger in as far as the second knuckle. He put his arm around me, pulling himself into me, frantically pumping my prick with his other hand.

"I need... I need.... Please, sir, I need you to fuck me," he panted in me ear.

I thought for a moment about turning him around, putting him against the wall and fucking him right there in the shower. No lube and no condom; that was not really a good idea. I pulled my hand out from his backside.

"On your knees!"

He looked a little surprised but he did as he was told.

"Now kiss my prick and ask me nicely."

He leant forward and covered my prick and balls with a flurry of kisses.

"Please, please sir, please will you fuck me," he asked between the kisses.

"How should I fuck you?"

"Please sir, up my arse. Please fuck me up the arse with your prick."

"Not here; in bed."

He pulled back and looked at me, his disappointment showing in his eyes. He too had thought about being fucked in the shower but was less practical about it. In bed seemed a trifle tame and I knew I was close to blowing it.

"Trust me, it will be better," I suggested.

"You're the expert," he replied, still with some reluctance.

"No, I'm the one who tells you how it's going to be."

"Yes, you are, aren't you," he sighed as, once again, he melted against me.

"The first thing to do is to rinse off and get dry. Now, come along."

I chivvied him out of the shower and, as quickly as we could, we dried ourselves and headed for the bedroom. On the way I grabbed the lube and a couple of condoms.

"What do you want me to....."

"Get on the bed! Now! Face down!"

I took a couple of the pillows and shoved them under him so that they lifted up and presented his backside. Without being told he opened his legs but I pushed them farther apart for good measure. Then I got up on the bed and, kneeling between his knees, squeezed out a good dollop of lube and, after slipping a condom over my finger, pushed it deep into his arse.

"You like this, don't you?" I asked as I pushed the lube in and opened him up,

"Yes, oh, yes please."

"But that's not all you want, is it?"

"No."

"So tell me."

"I want... I want you to fuck me."

"And why should I? Are you saying my finger isn't enough? Don't you like my finger up you?"

"Your finger's wonderful but...."

"But what?"

"Please, I need you to fuck me."

"I am fucking you."

"I need you to fuck me with your prick, please, with your prick." He was almost sobbing but, by now, I had his number. The more I piled it on the more he loved it.

I pulled my finger out and removed the condom that covered it. Then I another condom and fitted it over my prick. Kneeling forward, I took my prick in my hand and lined it up with his bum hole. At first he seemed to be too tight and I wondered if I was ever going to break through but, after a while, I managed to push the tip inside and, although I was never going to admit this to the punter, I started to fuck a man for the first time.

He was tight, really tight, and, even with the lube, each push was only getting me a little further inside. Mind you, that just made it feel good and, judging by the noises he was making, he was loving it too. Inch by inch I forced my way into him and each push made him give a little squeak, that mixture of pain and pleasure that I knew so well.

And then I was all the way in, buried to the hilt. Gently, slowly, I withdrew and then plunged in again. With each stroke he seemed to be opening up and, although he was still very tight, it was getting easier. I took it slow and steady, letting him, and me, feel every inch as I withdrew right to the tip and then slid all the way back in again.

"This is what you wanted all along, isn't it.?"

"Yes, oh, yes."

I thought for a moment, thought about the fantasies he seemed to be into.

"Maybe, next time, I'll bring along some of my friends and they could watch me fuck your arse while they wait to take their turn in the gangbang. And if you struggle you'll just be held down, helpless until we've finished with you," I suggested

"Oh, god, would you really?" He stretched out his arms as if they were tied to the corners of the bed. My guess had been right.

"Can you hear them laughing at you, laughing at how pathetic you are, tied to the bed, with your bum wide open for whoever wants to fuck you? Well, can you?"

"Yes, yes, oh yes!"

"You're just their dirty little fuck hole, aren't you? What are you? Tell me."

"Their dirty little fuck hole. Oh, please, fuck me harder, please."

And, all the while, my slow steady strokes were building. I was thrusting away, pounding into him and I could feel myself starting to come. He wanted to be fucked harder, well that was fine by me. It wasn't what I was normally into, I would have preferred to have been the one on the bottom but, if I was going to fuck him I'd fuck him so hard, so hard, so...

My prick seemed to explode as the spunk shot from me. Once, twice, three times I pushed myself as deep as I could go until, spent and exhausted, I collapsed on top of him.

Slowly I got my breath back and, as I did so, my erection subsided and I slipped out. I rolled off him and collapsed on the bed.

"Thank you, thank you, thank you."

I turned my head and looked at him.

"That was fantastic. When you started on about being gangbanged... how did you know that's a fantasy of mine."

"Just a lucky guess," I replied. "Now, you just lie there a moment, I need to go to the loo."

"Will you be coming back?"

"Of course, why shouldn't I?"

"I just wondered.... How long have I got you for? I mean, Mr. Mason just said you'd be dropping by; he didn't say for how long."

"All night, if you want."

"Really!"

"Just wait there. I'll be back in a moment."

When I got back from the en-suite he had tidied the bed and got in under the covers. I slipped in next to him and all the rough stuff seemed to be over so we just cuddled for a while. He couldn't keep his hand off my prick and, in return, I fondled his. We weren't exactly wanking each other off but we were both hard.

"Were you serious about the gangbang?" he asked shyly. "Could you..."

"Could I what?"

"Call up some friends...."

"Well, it's a bit late in the day now."

"I don't mean that, I mean next time."

"Next time?"

"Yeah, next time, could you bring a couple of friends? I'd pay for it."

"You'd have to ask my boss about that. He's the one who makes the arrangements. But I don't see why not. It could be a lot of fun. I bet you've got lots of ideas. Why don't you tell me about them?"

It was as if all his Christmases had come at once. He told me of all his submissive fantasies, fantasies that he had kept buried for years and now had a very real chance of acting out. I encouraged him by telling him about big strong tough Jed and Carl and suggesting things that we might do together. Of course, he was getting off on all this and, after a while, I really was wanking him off. We'd got as far as having him tied up, wearing my panties and getting golden showers when, for the second time that night, the spunk shot from him.

I fetched a flannel from the en-suite and mopped him down. Then, for a while, we just chatted. He still didn't seem like the normal sort of customer and that intrigued me. In fact, his inexperience had shown throughout.

"Is this the first time you've done this?" I asked.

"Sorry, yes, does it show?"

"There's nothing to be sorry about. I've really enjoyed it and, if you want to invite me back... well, you know who to ask."

"I'm not sure I do know who to ask. I mean Mr. Mason made all the arrangements. He said he knew some people who could... well... anyway, here you are. Do you have a card or something?"

I realised with a start that he didn't know that I worked for Mr. Mason so I glossed over that connection. I gave Mr. H's office as the contact number. A little more questioning revealed that he had met Mr. Mason at a civic reception. How they had been introduced by a mutual acquaintance and had hit it off immediately.

"Civic reception? Does that mean you work for the council."

"That's right. I'm on the planning committee. It was a sort of meet and greet for all the players in the big new reconstruction project. I gather he's one of the building contractors. One of the councillors introduced me to him and we got on like a house on fire. He's quite a man of the world, far more than I've ever been and he's got all sorts of contacts. He told this wonderful story about a schoolgirl drag act and all the amazing things she'd do. I told him I like to have a look sometime and the next thing I knew he was insisting that, if I hadn't tried... well... as I said, here you are. I'm really glad you are here." He gave me a little kiss. "You've been super."

"So have you," I replied.

And then, by mutual consent, it was time to sleep. However, it took me a while to drift off and I mused on how this was the second person in town planning to find Mr. Mason or his friends very generous. Given that Mr. Mason had supplied the hotel room as well as my services I wouldn't put it past him to find that there were hidden cameras that had captured our little games. It looked very much like Mr. Harper was going to find my services costlier than he had thought.

Tuesday morning found me climbing the stairs to Mr. H's office. Tracy was waiting for me with a big smile on her face.

"Hi there. All ready for some girly clothes shopping? I hope you've brought plenty of money."

"I didn't bring that much."

"Never mind. We can charge it to the company and take it back out of your wages. How did you get on with Mr Harper last night?"

We went down to my car and, as I drove her across town to the clothes shop, I told her all about Mr. Harper and what he had had me do to him. 'The quieter they are the kinkier they are,' was her response.

When we got to the shop it was actually a warehouse. It was clear that most of their trade was mail order as they didn't have much presence on the street. We went in and Tracy was greeted as an old friend. Tracy explained briefly what we were after and we were taken through to the showroom in the back.

Talk about an Aladdin's cave! The main problem with being a guy who likes to wear women's clothes is that they are, inevitably, designed to be worn by women. As I have no intention of changing my body to fit the clothes what I needed was 'women's' clothes that had been subtly redesigned to be worn by men.

As soon as I walked into the showroom I saw a very obviously male manikin wearing the most darling gymslip in royal blue. It wasn't as outrageously slutty as the Belinda costume but that, to my eyes, just made it sexier. There were, of course, other costumes, the French maid, the cheerleader, and there was the Belinda outfit but it wasn't any of those that really caught my eye. There was an evening wear collection and, right in the middle, one of those Chinese dresses in a beautiful turquoise with gold trimmings. I just had to try it on.

As with the shoe shop, the staff had seen it all before and were completely unshockable. They already had my measurements as Tracy had emailed them through so they fetched out a dress in my size and, quick as a flash, my jeans and tee shirt were off and the dress was on.

It felt perfect. The saleswoman described it as a Cheongsam dress but I still thought of it as simply Chinese. The hem was maybe three or four inches above the knee and although the skirt was tight it was slit up the side which meant it was still possible to walk while wearing it. Tracy then insisted I had to accessorise with a little blue clutch bag and matching open toed sandals with a three inch heel. I strutted around feeling like a million dollars.

However, that was far from the end of things. According to Tracy I just had to have an 'lbd' which turned out to be a little black dress. We tried quite a few before we found the right one; a nice slim cut which disguised my male shape and made the best off my legs. Again there had to be bag and shoes to match.

I had just taken off the lbd when Tracy handed me something very gauzy and flimsy and, above all, pink.

"What's this?"

"A baby doll."

"A what!"

"Try it on."

Slightly reluctantly I did so. I looked in the mirror and tried a little swirl. There was no denying that, in a rather slutty, Belinda Bombshell way, it was very sexy. It was frilly and lacy and fastened in the front with the cutest satin bow. Moreover, as with everything else they sold, while it was indubitably feminine it was designed to be worn by a man. Mostly, when you see guys in sexy lingerie, they just look stupid. This one, like the dresses, managed to avoid that.