"Welcome home, sir." The man dispassionately eyed Tony's bare bottom. "Lost your clothes again? It looks as if we'd better lay in a good supply for you, as careless as you are with them." He turned toward the door on the far side of the room. "Joey! Your master's home again."
Tony's valet, the 16-year-old Joey, came running into the room. As soon as he saw the expression on Wilson's face, he stopped running and assumed a proper valet's air. He was dressed in a perfect copy of Wilson's valet uniform, and gestured for Tony to follow him as he moved toward the stairs that led to Tony's room.
Tony was only too happy to follow him. He only wished that Wilson hadn't slowed the kid down - he wanted to get away from the cynical eyes of Wilson as quickly as possible. In fact, he wanted to get away from all eyes for a while - or at least get dressed.
For what seemed an eternity, he slowly made his way up the stairs behind the suddenly-dignified Joey. And all the time, Wilson stood in the hall, staring impassively at Tony's bare ass as it alternately flexed and spread each time Tony took another step. Tony felt a little uneasy as he looked back down - he was sure that the man was staring straight at his asshole. He reached back with one hand and tried futilely to cover his asscrack. All he succeeded in doing was to further focus attention on it. Wilson caught his eye and almost smiled.
He was greatly relieved when they reached the top of the stairs and turned toward his room. Once there, Joey turned to him and informed him that he was going to have to take measurements. Tony was obviously in need of more clothing, and the DM had agreed to have some made.
Since Tony was dressed in nothing but a T-shirt, sneakers and socks, it would be easy enough to get accurate measurements. But Tony hadn't counted on the effect of having a squeamish 16-year-old's hand wandering around his chest, his waist, his hips, this thighs. By the time Joey got the tape around his hips, in particular, Tony was half-hard, what with the younger boy's hands trying to get the tape to lie flat across his ass-cheeks, then bring the ends together right over his cock and balls. His cock was too arched out for an accurate measure, so Joey had to press it firmly against Tony's big balls. Well, that just made it worse. Finally, Tony had to hold his rock-hard cock out of the way while Joey measured under and around it.
After about 10 minutes of being outrageously felt up by the naive 16-year-old, he managed to get Joey out of the room, so he could relax. He decided to get dressed immediately, and as completely as his wardrobe would allow. After taking a shower, he ended up in bib overalls, with a T-shirt and briefs under them (no more easy access to his ass with one of those jock-straps). Of course, being Tony, those briefs were the sexiest Calvin Kleins on the market. Still - nobody was going to see them, right?
As paranoid as he was, he fastened every single button on both sides of the overalls. In his singles-bar days, it was his habit to leave them gaping open on the sides from his armpits halfway down his hips, exposing his firm young flesh to the hungry mobs (he never wore a T-shirt on his trolling nights, and his briefs were so brief you barely noticed the thin strap arching across his bare hips). On his good nights, he used to be able to walk up to the bar and within 5 minutes have a chick on each side of him, buying him drinks and exploring his body under the overalls. He could still remember that glorious feeling - one hand inside the front of his briefs, playing with his hard cock and balls - another hand in the back, squeezing those full ass-cheeks of his and tickling his asshole with her fingertips.
Just thinking about it had gotten him all squirmy, though. He started looking at himself in the mirror, trying to picture what the chicks saw on those hot nights. Despite himself, he was disappointed. Yeah, he swore he'd stay fully dressed from now on. But . . . on the other hand, that dowdy little frump in the mirror wasn't the real Tony. All covered up and sexless.
If he had to turn into that, it just wasn't worth it.
He unbuttoned the sides of the overalls. That was more like it. There was at least a little skin between the T-shirt and the bikini briefs. But the more he looked, the less he was satisfied even with that. Even when he leaned forward and the overalls gaped open, there wasn't much to see. No chick was gonna get all squishy after getting a peek at a guy's underwear. She's gotta see some skin, some tits, a big bulgy basket, a hot, sexy ass.
In a flash, his pants were around his ankles, and he was wiggling out of the T-shirt. Oh, yeah! That was more like it. That hot stud in the mirror was everything Tony knew he could be. Now, with nothing getting in the way of the big basket in the front of the briefs, and with the rear of the briefs disappearing between those twin melons of his, he was the personification of the wet dreams he inspired in the bitches he teased.
He pulled up the overalls again. This time, they looked just about right. He walked around in front of the mirror. The little teasy hints of bare ass and jiggly basket were the hottest things he'd seen since . . . well, since the last time he'd really taken a look in the mirror.
That was it! He'd decided. He wasn't going to let these guys turn him into some kind of anti-sex frump. He was just gonna have to learn how to play smarter. Let 'em look, but try to stay away from all those hands and dicks. The money was good enough that he was willing to put up with a lot. But he had his limits. Hey, he was the best! He was in no mood to surrender.
He had to admit, though, that so far it seemed like he was a little outclassed. But he didn't give a damn what they thought - he was no idiot. It might take a while, he was going to learn to beat them at their own game. Every setback was just another lesson learned. Eventually, he'd come out a winner. How could anybody with a killer body like that not come out a winner? Impossible!
In this mood, he made it through the rest of the day. By the time dinner was announced, he felt like he was really in control again.
When he entered the dining room, he made a point of giving the DM a good look at the kind of skin he was showing. Practically bare tits and ass. Big bouncy basket barely restrained by the soft cotton bikini briefs. He sat in "his" chair opposite the DM, and let his overalls fall as they may - gaping open and giving Joey a full view every time the kid served him.
The DM was clearly enjoying all this. He maintained a pleasant conversation with Tony through the main course. While they waited for coffee, and aperitifs, the DM asked Joey whether he'd had a chance to finish any of the clothing he'd been working on for Tony.
When Joey said that a few things were ready, Tony was interested. He asked Joey when he'd get to see the new clothes. He was curious as to what Joey (or whoever decided these things around here) considered appropriate clothing for him. He hoped they'd be real high fashion. He never felt like he knew much about style and all. He knew what looked good, but somehow it never really looked expensive on him. Maybe even a little cheap. Although he'd never admit it, he admired the way the DM dressed, and wished he could exude that kind of confidence and power.
When the DM suggested that Joey go and get whatever he had ready, Tony was even a little excited. The drinks came while Joey was away, and Tony downed a brandy or two while they waited.
When Joey came back, he only had a couple of things over one arm. Tony was disappointed that that's all there was, but still hopeful. Joey apologized as he brought the garments over for the DM's inspection. All they'd finished were Tony's gym clothes. He held up the shorts. They looked about like gym shorts should, except that they seemed kind of flimsy from where Tony was sitting. Of course, he couldn't see very well at that distance.
"Try them on, Tony. Let's see if Joey's measurements were right. No point in having a whole lot of things made if the basic size is off." The DM waved Joey down toward the other end of the table.
Well, it was pretty obvious to Tony where this was leading. It was just an excuse to see him in some skimpy clothes. But so what? The guy had seen him bare naked, for Christ's sake. What difference would it make to let him see him in gym clothes.
When Joey handed him the clothes (gym shorts and top), Tony stood up to go change. The DM stopped him short. "Don't waste my time. Change here."
Tony protested, said he'd just be a second, but clearly the DM wasn't about to listen to reason. "Come on, Tony. You've already shown me everything you've got. What are you so uptight about?"
Tony had to admit he had a point. Downing another quick brandy, he finally gave in. He started to unfasten a shoulder-strap, but the DM stopped him. "Let Joey do it. That's his job."
He also had Tony move down to his end of the table so the DM could see the clothes better. Tony blushed a little as he felt Joey's soft fingers fiddling with the overall straps and then sliding them down his body. The overalls were very loose, so in seconds Tony was standing in front of the DM in nothing but his sneakers and skimpy briefs.
Tony began to realize what an embarrassing position he was in. He couldn't do anything but stand there, while the DM examined his body. Then he felt Joey's fingers sliding into the waistband of his briefs as he started working them down over Tony's jutty ass. Tony jumped and tried to stop him, but the DM soon quieted him down again. "The shorts have their own support built in.
You don't wear anything under them, unless you want to look some kind of idiot.
Tony was insecure enough about his fashion sense that that hit home. He didn't want to be naked in front of everybody, but he sure didn't want to look like an idiot, either. Blushing a little, he stood still while Joey slowly worked the briefs down to his ankles. He clasped his hands over his cock and balls, which seemed to amuse rather than annoy the DM.
Once the briefs were off, the DM told Joey to take off Tony's shoes, too. In future, he should always remove shoes before other clothing. Never leave your boss looking stupid.
Tony stood there, completely naked, feeling stupid, while the DM slowly looked him over. Joey was busily getting the shorts ready for Tony to try on. Several minutes later, Tony was finally allowed to step into the shorts.
Slowly Joey pulled them up his legs. They were a little snug over his hips.
Joey had to pull the rear up over his ass first, and then bring them up in the front.
Tony jumped and turned a quick pink when Joey casually reached into the front of his shorts and arranged Tony's frontal assets in the built-in pouch. It was over before he could object, but the memory of those soft, warm fingers on his cock and balls left him a little breathless. He was a little woozy from the brandy anyway.
By the time Joey got the top on him - a sort of short tank-top, much like he usually wore anyway - he felt a little better. The clothes felt good. They fit snugly, but were pretty comfortable. They felt like they were made of silk or something. Very sexy.
The DM chuckled as he had Tony slowly turn around and show him the outfit. He had him try bending and stretching in several directions. Finally, he ordered Joey to go bring a mirror so Tony could see what he looked like. A few minutes later, Tony, his head spinning just a little, looked up and turned around to take a look at himself in the full-length mirror.
It was like someone hit him over the head. He looked stark naked. All this time, the DM had been staring at his bare balls and ass. The material the gym outfit was made of was completely transparent. In the candle-lit dining room, he couldn't even tell that the guy in the mirror had anything on. His cock and balls, all snugly packaged in the see-through jock, looked like they were bouncing around in mid-air. From the rear, every inch of his deep crack was clearly visible.
He felt like he'd been made a fool of - again. All this time, he'd let himself be put into poses that showed off his big teen-age balls and his hot young ass to a man sitting two feet away.
"That would make quite a uniform for the office, wouldn't it, Tony? I know how much you like to show off that big ass of yours. It might be a nice idea for the guys at the office if you showed it off a little while you were working under their desks." He laughed at Tony's expression. "Don't worry. We don't want that much distraction on the job." His expression went sober again. "But maybe when you're working out in the company gym. . . ." He smiled. "Maybe this will be your outfit."
Slurring his words slightly, Tony swore he'd never work out if he had to dress like that. But the DM had no trouble at all changing his mind. But he did get one concession. He'd only have to wear it when he worked out in the executive gym. Board members and maintainence workers only. And he had the choice - he could either wear the outfit . . . or work out in the nude. Whichever made him more comfortable around all the older men that used that gym on a regular basis. Since he was so much younger than most of them, he'd probably be asked to help out a lot with spotting and stuff like that. Whatever. After all, they were his employers.
While Tony didn't entirely like the sound of all this, it seemed like it could have been worse. He sure wouldn't want to be naked in a gym with that bunch of clerks who were all over him in the plant. Well, he'd take it one day at a time. Maybe the DM was just playing with him.
Before they finished, though, the DM gave Joey a series of adjustments to be made on the shorts. The main one was to adjust the support part of the garment - right now it was built like a pair of briefs inside the shorts. Joey was told to eliminate the rear part of that piece - turn it into jock support only. "We don't need two layers of cloth between that ass and the outside world. One is more than enough." There were also some adjustments to the jock pouch that involved a lot of Joey's hands plunging into the crotch and moving things around. Tony was glad he was a little stoned, or he was sure he would have gotten really pissed off somewhere along the way.
As it was, the DM finally ordered Joey to take the shorts back. Tony was left is nothing but a transparent tank-top, his bare cock and balls still bouncing a little from the disrobing - only inches from where the DM was sitting, appraising his voluptuous young body with some amusement. "Nice top, too. I didn't notice it before. Turn around. Let's see the back."
Tony knew damn well the guy just wanted a closer look at his ass. He tried to refuse, but the man just laughed and repeated the order. Tony grudgingly complied. He heard a chuckle from behind him. "Very nice. Now take it off." Tony didn't bother resisting. He knew he was going to end up naked again, anyway. He pulled the tank-top over his head, while the DM watched the flexing and shifting of the teenager's smooth globes. "And again, very good. I think you should thank Joey for the good work he's done for you." He turned to Joey, "Take Tony, here, back to his room."
"Hey, where's my clothes?"
Joey blushed a little, and said, "I left them in your room when I went to get the new things. Sorry."
"Don't worry about it," the DM chimed in. "Just give him your pants."
In minutes, Tony was wearing a very tight pair of pants, and Joey was looking all pink and virginal in a pair of fairly skimpy white briefs. When he turned to lead the way, though, Tony's breath caught. The kid had the most surprisingly voluptuous ass he'd ever seen. Comparable only to his own. But Joey's was younger, softer, whiter. It jiggled as he moved, almost turning Tony on, it looked so sweet and fuckable. Tony resolutely put these thoughts away. He was into chicks only.