The next day, as instructed, Tony came directly to Joe's office in the morning. Joe had the repaired uniform shorts ready for him. He ordered Tony to strip down and try them on.
The kid was a little taken aback by the casual way Joe was taking control. He didn't much like being told to strip, like he was some kind of a dress-up doll.
On the other hand - it was a good job, and Joe was the boss. Obediently, if a little sullenly, the kid stripped down to his jock.
"Hang up those clothes, kid - this isn't a pig sty."
Still stewing a little at being treated like a child, the kid grudgingly obeyed - unwittingly doing a real cock-tease number - showing off his big bouncy buttcheeks as he moved around, flashing his deep ass-crack at his boss each time he bent over to pick up an item.
It took him a while to get everything neat enough to satisfy Joe, though. His first couple of attempts were so pathetic that Joe just picked up the clothes and threw them back on the floor. He had to start all over. Finally, he seemed to have gotten it right. But just to be sure, Joe had him get down on all fours for one final check of the floor to be sure he wasn't leaving any mess behind.
Success! Joe helped him to his feet and handed him the shorts. "Good boy! Now try these on. Let's see if they work."
Tony finally managed to squirm into the snug-fitting shorts, squeezing his big asscheeks into them with obvious difficulty.
He tried, unsuccessfully, to protest as Joe "tested" the rear zipper. Nevertheless, he was relieved to find that it worked well. Joe explained that it had been replaced by an industrial strength zipper, and that he shouldn't have any trouble with it in future. He had Tony pull it up and down a few times to make sure he knew how. Finally, he let the kid finish dressing and fastened the key belt around his waist.
"This time, if those guys try anything, you just let me know, OK? There's no need for anybody but you amd me ever to have their hands inside those shorts.
Understand?"
The kid nodded, blushing a little. What did he mean by "you and me"? He must have meant when he puts the key belt on. That was sort of "inside" the shorts - inside the beltloops, anyway.
The next day, Joe announced that he was giving the kid a raise.
Tony couldn't believe his luck. A raise in the first week - and such a big one! He was even better than he thought.
Immediately afterward, Joe added one new requirement - since Tony was only going to be wearing a jockstrap under his uniform shorts and since the shorts were expensive, he would from now on be required to douche every morning before putting the shorts on. It was Joe's responsibility toward the company to make sure that at the start of every day the kid's ass was perfectly clean inside and out.
The kid was shocked - no way! Never! Douche? He was a man!
But after a few seconds, he remembered the raise. Well . . . That kind of money would be pretty hard to give up - maybe it wasn't all that bad an idea.
Joe explained that he realized it might be embarrassing for Tony to douche in front of all the other guys in the employee's locker room (Tony hadn't even considered that yet - he turned pale at the thought). For that reason, Joe had had a douche installed in his own private bathroom, here in his office. Tony could douche there every morning before getting dressed.
Minutes later, a very naked (and nervous) Tony was lowering his smooth teenage ass over Joe's private douche.
Joe guided him. "That's it. That's it. Just get your asshole right over the spout. There you go. Now lower it down. Lower. Lower. No, it's gotta be all the way inside you - otherwise the water'll squirt all over."
Slowly, the kid impaled himself on the fat rubber spout that Joe had had made specially for this douche - it was, in fact, a replica, correct as to size, of Joe's own cockhead. The kid groaned as he felt his asshole slowly spread open over the rounded top of the nozzle. The teenager was pink with embarrassment at being watched like this. "Hold it right there. That's far enough for the first time." Joe turned on the warm water.
Tony groaned again as he felt the water jetting up into his ass, swirling inside him.
After alternately spreading, douching, and draining his asshole several times, the kid was allowed to dry himself. Joe had him do a few deep squats, just to make sure all the water had been squeezed out. He wouldn't want anything dribbling down his thighs, now would he?
Over the next several days, Tony slowly got used to the ritual. Every morning, he arrived at Joe's office, stripped naked, carefully hanging everything where he'd been taught, walked into the bathroom and squatted down over the douche.
Joe always positioned the kid and controlled the water flow - Tony wasn't allowed to do any of this on his own.
That weekend, Joe quietly had the nozzle replaced by a slightly longer one (made of firm but flexible rubber) that he'd had made at the same time as the first.
The following Monday, the kid thought something seemed a little different, but he wasn't sure, and in the end decided not to say anything. This time, though, as Joe lowered him all the way down onto it, he felt his ass being stretched again, and he groaned as loud as he had the first time. By the time the douche started, he had fully two inches of thick rubber cock-replica up his tight virgin ass.
By the end of the session, though, he was already almost used to it and figured it probably only felt bigger because his asshole had tightened up again over the weekend.
Over the next several weeks, the douche nozzle slowly grew. By the time it reached 10 inches, Tony was almost sure that it was longer than it had been that first time. But he couldn't be sure. The change had been so gradual that he could never swear to it. He had no trouble taking the whole thing, anyway,ever since Joe had taught him how to grease up his ass before starting. The grease was water soluble - it washed out before the douche was done - so he didn't have to worry about getting it on the shorts.
It was getting so he secretly enjoyed the sensation, too - plunging his ass up and down on the big nozzle felt great - the way it rubbed on his asslips - the way it pressed against his prostate when it was deep inside him. While getting himself positioned, he sometimes managed to get in a few bounces on it before Joe turned on the water.
He became very indignant, though, when Joe suggested once that he might like to try a dildo at home sometime. What did he think he was, anyway, a queer? No way! The only reason he put up with the douche at all was because he wanted to keep his shorts clean. Christ! The nerve of the guy!
He did, however, consent to one change - a hand-held nozzle. In fact, it was the same nozzle as before, but connected to the douche by a long hose. This allowed the kid to be in a more comfortable position when Joe slid it up his ass.
Joe had him try several positions over the next few days, so he could pick the one that worked best for him - on his hands and knees, on his elbows and knees, on his back with his legs in the air, standing bent over grabbing his ankles. They all worked pretty well, actually, but he found he liked it best on his back - that way he could actually watch the nozzle going in and out. There was something about watching Joe down there between his legs that made it even more of a turn-on.
Joe had an examination table with stirrups installed, just to make it more comfortable for the kid to keep his legs in the air. He also had a drain built into the floor, to take care of all the running water.
From then on, the kid came in, stripped naked, and lay down on the table. With Joe's help, he positioned his legs in the stirrups, which were spread wide for maximum access to his asshole. Then Joe had him slide down the table until his asscheeks were bulging a little off the edge, ass spread wide for easier penetration.
Joe slowly and thoroughly greased the kid's asshole, pressing the grease as deep inside as he could reach with his fingers, corkscrewing them in and out until the kid's hole was as slippery as he could get it.
Then he slowly slid the oversized nozzle up the kid's ass. By this time, Tony just moaned in pleasure at the sensation. Joe pressed it deep, pulled it all the way out to the lips, then deep again. After several minutes of this, the kid was getting obviously excited - his cock was hard as a rock, bouncing and jerking with each thrust of the nozzle into his asshole. Precum dripped over his belly as Joe fucked him deeper and deeper with the rubber cock.
One day, at the deepest point of penetration, the kid began coming - squirting wildly all over himself. The first time he let it go so far, he was pretty embarrassed. But Joe just hosed him down and wiped him off with a towel.
It became part of the ritual. Each day Joe would pump him until he was writhing in the stirrups. Then he turned on the water and the kid came in buckets.
It wasn't long before Joe managed to actually fuck the kid. When Joe first slid his cock between the smooth round cheeks, the kid hardly noticed at first. Once he realized what was happening, though, he tried to fight back. But all his ass-flexing and squirming just drove Joe's cock even deeper into his ass. And after a few deep thrusts, he wasn't fighting very hard any more.
Within a few days, he was getting fucked every day as a matter of course - just before the douche. Joe got it all on film - every inch of hot flesh on the kid's body was revealed to the cameras in every subservient position he could devise. His pretty ass was recorded as it arched up, begging to be fucked, the kid's face clearly visible in the shot.
And then, a few weeks later, the kid suddenly found himself transferred to a branch office some distance away. Joe himself invited the kid to his office to introduce him to his new boss, who was the district manager. Joe made it clear that the kid's future with the company would depend on how satisfied the district manager was with his performance.
The kid was then told to remove his uniform (which was company property and belonged to the central office) in preparation for taking a ride with the district manager out to the branch office. He'd be issued his new uniform out there.
After some argument, which was firmly dealt with by Joe, he began undressing - beginning with his shirt, then his shoes and socks. Finally, he unzipped his shorts and bent deep to work them down over his muscular calves, leaving him naked except for his jock, Joe told him he'd let him keep the jock, so he could preserve at least some of his dignity as his new boss escorted him through the office and out to the company car.
Bent nearly double, his bare ass flexing high in the air, the kid struggled to get the shorts over his feet. Belatedly taking in what Joe just said, he looked shocked and started to protest, saying that no way was he walking through the office like this - insisting that Joe let him get his own clothes from the locker room. Joe cut in, "You know, kid, one more word and you're gonna lose the jock, too." The kid shut up and stared at him. "And just for your information, all your belongings, including the clothes from your locker, have already been packed up for you and moved to your new residence."
This elicited another storm of protest, that took a little longer to subside.
Joe finally managed to explain to the kid that during his training period, he would be living in a suite of rooms that had been assigned to him in the home of the district manager. In the meantime, it would save everybody a lot of trouble if the kid would just go along with the DM, look his new space over, find out what his duties would be, and then - if he still wanted to - he could discuss any problems he might still be having with it.
By the time he was done, the kid was beginning to feel that he was the one who was making a big deal out of nothing. What did he have to lose? It was a better job, more money. Why didn't he just give it a try?
A few minutes later, without quite realizing how it happened, he found himself meekly following the DM down the hallway outside Joe's office. He began to blush as he realized that he was actually doing it - walking bare-assed past Joe's secretary, then past all those workers in the hall. He could see them giggling and peeking at his bare tits and ass - none of them were exactly staring, but they were obviously getting an eyeful. He'd never seen so many people in the corridors - the word must have gone out beforehand somehow. He kept his eyes lowered - he couldn't bear to face them.
When they got into the elevator to go down to the car parking area, there were already two guys from the sales department in it. They looked startled, but Tony just blushed and stepped in, turning his back to them. The DM stood beside him. Just as the door closed, the kid felt a hand on his ass. He took a quick breath. The hand began exploring. He and the DM were going to have to get a few things straight. But he decided not to make an issue of it here in front of the salesmen.
Then, just as he glanced over at the DM and realized that both his hands were in plain sight, the salesman who had been feeling his ass suddenly moved forward, pressing his crotch into Tony's ass. Tony was so shocked, he froze.
Before he could think what to do, the crazed salesman had pulled out his hard cock and had shoved it between Tony's cheeks, plunging it into the teenager's defenseless asshole.
By the time the other two men realized what the salesman was doing, the elevator doors slid open. It was the car park - fortunately, there wasn't a soul in sight. The DM simply took Tony by the arm and stepped out of the elevator. As they did, there was a sucking sound as the salesman's cock popped out of Tony's hole. Just as it did, the man's cock erupted, spraying cum all over the kid's hot young ass.
Tony blushed bright red with embarrassment, but not a word was spoken as the DM led him over to the stand where the chauffeur was waiting by the limo. The chauffeur ushered the DM into the back. Then, with a little smile, he turned to the blushing Tony, pulled out a clean rag and carefully and efficiently wiped the cum off the kid's hot cheeks. Tony couldn't stop blushing as he felt the chauffeur's hands wandering over his ass.
As he stood there, still in shock, he gradually became aware that the clean-up operation had been going on for too long, and that it felt like the chauffeur wasn't bothering to use the rag anymore. In fact, he was taking advantage of Tony's state of shock to thoroughly explore his ass, running his bare hands over the full smooth cheeks. When Tony felt the man's fingers sliding into his asscrack, he jerked away and turned around indignantly.
But before he could say anything, the chauffeur smirked, took his arm and turned him toward the door to help him in. Tony almost jerked away, but decided to try and relax - the man was just doing his job, after all. Nevertheless, he was very conscious of his bare ass and the show he was putting on for those outside (the salesmen were still standing in the open door of the elevator, watching) as he bent over and climbed in next to the DM. His asshole was probably still a little red and dilated from that salesman's (big) cock being shoved into it. As he sat down, though, the coolness of the seat felt good pressed against it.
Tony looked around at the inside of the limo - it was the first time he'd ever been in one, and it was pretty impressive. It was all plush and padded, the size of a room. There was a small refrigerator and a cabinet that probably had a TV and sound system in it, judging by the speakers. The kid was a little intimidated.
The two of them were seated on a sort of couch that served as the main seat for the passenger area. There was plenty of room for the two of them, but Tony felt uncomfortable - the DM was so impressive that he seemed to take up more than half the couch - Tony stayed pressed against the end, as far away as he could get. He crossed his arms, trying at least to cover his bare tits.
What made him even more uneasy was feeling the plush covering of the couch against his bare ass. The way he was sitting, it even pressed against his asshole. Tony squirmed - it was starting to tickle. He felt a sudden need to scratch his asshole. He squirmed again.
The DM gave a deep chuckle. "Better get used to it, kid. You go around with an ass like that on display, you're gonna get fucked. No two ways about it."
Tony glanced over at the man - he couldn't really see his face very clearly - he was in a kind of shadow. He heard another chuckle.
"The way you bent over and flashed that hot little hole of yours in the chauffeur's face, I thought I was going to have to pry another one out of there before we could get going."
Tony turned red as a beet again.
"Don't be embarrassed - an ass like yours is like a work of art. It deserves to be on display. It was made to be admired by men - lots of men."
Then there was silence for a while, to Tony's relief. The way this guy kept talking about his ass made him nervous.
A little later the DM asked Tony if he knew anything about massage. "A little - I'm not an expert or anything . . ."
Without Tony quite understanding how it happened, he ended up giving the guy a foot massage. Following his new boss' instructions, Tony ended up on his knees in front of the man, bent low, slowly massaging the man's bare feet. The way he was working - knees spread apart to keep his balance as the car moved - his ass ended up in a pretty classic "fuck me" position.
At one point, he glanced back over his shoulder - only to catch the eye of the chauffeur in the rear view mirror. He was staring at Tony's blushing asshole. He looked back at the DM - the man was grinning at him. Obviously, he had set this up on purpose.
When he finally finished the massage to the DM's satisfaction, he moved to return to his place on the couch.
"Oh . . . would you mind just staying down there, Tony? I'm a little tired and I may want to lie down for a while. Maybe you could just stretch out, too, on the floor? It looks comfortable enough."
Tony was happy enough to stay where he was - the floor was, in fact, very soft and comfortable, and he was starting to feel a little tired himself. He stretched out face down and pillowed his head on his arm. Within a few minutes, he was sound asleep.
He woke up in the middle of an erotic dream - someone was giving him a sensual massage over his entire body, then Joe was fucking him again and the sensation was wonderful. As he woke, he realized that, in fact, someone was on top of him, fucking him. He tried to get out from under, but the other guy was much bigger and stronger - he couldn't budge. As he struggled, though, the movements evidently brought his assailant over the edge. He felt the man coming deep in his ass.
When he finally rolled off, Tony realized it was the chauffeur. And the DM was still sitting right there watching and grinning.
"I asked the chauffeur to wake you - we reached our destination, and you were sound asleep. Evidently you were in the middle of some kind of wet dream. The poor man was unable to resist taking advantage of the way you were wiggling that hot ass of yours around, pumping it up and down. But at least you're awake now, right?" He laughed as Tony glared at him, rubbing his burning asshole.
"Now let's go inside - you'll want to see your room and meet the rest of the staff."