He'd seen the ad running in the local paper for the past several weeks, and he had to admit, it intrigued him -
"Discrete handyman needed for long-term remodel work. One employer, private residence needing significant updates based on owners' personal needs. Rewards commensurate with performance. Contact............"
He thought it might be the way it was worded - the emphasis on "Discrete", and no mention of payment...or experience required, just "reward commensurate with performance". He had a few minor jobs lined up already. Old Lady Taylor had some door knobs that needed replaced and Mr. McCracken needed his gutters cleaned and wasn't able to get up on ladders anymore. Seemed like most of the town was getting older and "less able" to do for themselves anymore. He didn't mind really, kept him in grocery money and the occasional beer. Nothing that challenged him though - or used any of the skills and talents he really did have.
His old man had been a contractor - could "build a house from the ground up starting with nothing but a pile of toothpicks, bricks and rocks". It was an old joke when he'd been growing up and he didn't think much of the O.M.'s skills and abilities. Not then anyway. Then it was just a pain in his ass, getting stuck all summer long hauling asphalt shingles up and down ladders doing roofing jobs - or spackling for finishing painters - or any of the myriad other "jobs" his father had found for him to perform as "unpaid labor". He had to admit now though, he'd learned. He'd learned a lot. Probably more than the old man had planned when some of the construction teams had taken him "under their wing"....
Might have been just because he was a skinny, long-haired kid. Made him an easy target for the jokes about "sissy boys" and not being able to tell if he was a boy or girl from behind. On the other hand, might just have been because they were mean fuckers - too small minded, and small town to leave him be. Granted, there were some whose only interest was in teaching him "useful" skills - how to use a miter saw, or hang sheet rock. He was still grateful to them for providing him with a way of earning a living.
It was "the others" - the half dozen or so finishing painters who, at the end of a long, sweltering week, the summer he turned 18, had turned up with a case or so of cold beer. They'd encouraged him to drink, and then sent him up the ladder to finish taping and mudding. He'd gone up, not realizing that, once he was on the ladder he was trapped - and with the help of the beer, he'd initially been a semi-willing victim to their hands and mouths. He was young then, a virgin, and like all teenage boys, perpetually horny. Just starting to date he had no experience to relate the events to and knew only that, at first, the feel of the older mens' hands and mouths on his genitals and ass had been wildly stimulating. He remembered his cock feeling so hard he'd thought he could hammer nails with it and he'd cum twice within mere minutes.
It was after - after they'd pulled him down from the ladder and bent him over the sawhorses that things got - not bad, but tough. The first few times had hurt like hell of course - they weren't particularly gentle and they'd all had too much to drink. He'd bled off and on for much of the next week. Just when he thought he was starting to recover nicely his father had informed him that the "crew from last week" had been so impressed with his work that they'd asked for him again - "special".
He'd arrived that morning on shaking legs but with his cock already hard and throbbing. They'd had a few more surprises for him that day he recalled - a lacy satin teddy and tap pants had gone on first, then lace topped, stockings made to stay up by themselves. A pair of low heeled mules and a touch of rose lip gloss had completed his ensemble. At first, the hard hands of the workmen had been rough, stripping and fondling him before they began dressing him in the items they'd brought - to "teach him another lesson". But one by one their voices had grown hoarse and hushed and their hands had gentled - stroking his balls sweetly as they dangled from the legs of the tap pants. Finishing they'd stood back and looking at their trembling hands and straining cocks he'd felt flushed with the sense of power over them he'd felt.
He'd spent the day strutting through the house - clambering up and down the ladder - luxuriating in the feel of the satin and lace against his skin. Watching them watch him out of the corner of their eyes - taking every opportunity they could to touch him, stroke him, rub against him with their hardness. He liked it. Liked the feeling of control it had given him, but loved the feeling of the material on his nipples and rigid cock or sliding over his ass when they slid their hands up and down his crack. Before he went home that night he was aching all over, the stockings and tap pants a wet sticky mess from the loads of cum draining from his ass and that he'd shot off himself with their handling. His jaws ached and his lips felt raw from sucking one after another cock. But they'd let him keep the gorgeous clothes, and even wear them home under his own clothes. It had been days before he'd washed them - keeping them under his mattress to fondle and masturbate into. Wearing them under his clothes - or strutting around the house in them when he knew he couldn't be discovered.
Early girlfriends were always impressed that he wasn't trying to get them OUT of their lingerie - but seemed content to fondle them through the clothing, or rub against them, occasionally even exciting them orally through the silk, satin or nylon. He'd eventually joined the military trying to get away from his Old Man. Maybe if his Mom hadn't died when he was so young things might have been different, but there was just the two of them, and no one to mediate their fights. During that time it hadn't usually been possible to enjoy his "little habit". He'd missed it. Time spent perusing girlie magazines and lingerie ads wasn't for the usual reasons - not that he didn't enjoy looking at naked girls and was no longer a virgin with women either - but he liked to look at the ads and imagine how it would feel to be wearing the clothing in the ads. THEN he would finally get so hard that he could cum in a few simple strokes of beating off.
After leaving the military he'd come home, thinking he'd pick up his life again where he'd left off, only to find his high school sweetheart had married a nice "college boy" and moved to the Capitol. Dude was in banking, or something like that - something that brought more financial rewards than cleaning the towns gutters, building an occasional wine cabinet and painting siding. He'd never married, not that there hadn't been women, even some fairly serious relationships, but something always seemed to be missing.
He kept busy and the ad stayed in the paper. But the day came when the odd jobs began to dry up as the economy tanked and no one had money to hire a "Handyman" anymore. The fact that the ad had stayed in the paper had really begun to pique his curiosity as well, he wondered what the job had entailed, or why it had gone unfilled. And finally one late afternoon, after a beer or two, he had called the number. The voice on the line was soft but husky. Female he was sure, but with a sound of too many late nights and cigarettes. What the old man would have called a "whiskey voice" he recalled. Her car would pick him up at the local convenience store parking lot in two days, but he was going to have to prove to the driver, and later to her, that he could be discrete - not talk about the work he would be doing for her. He had the two days to figure out just HOW he was going to do that.
On the afternoon in question he was at the Gas-N-Go standing next to his truck in plenty of time. When the Suzuki with the darkened windows pulled up next to him the driver only lowered the window a few inches - enough to look out with polarized sunglasses and a black chauffeur cap. He unbuttoned the top two buttons on his shirt. The window rolled back up, but he heard the doors unlock and he slid into the back seat, behind the driver. Lying on the seat was a blindfold and soft, classical music was playing over the speakers. He realized others before him had probably made this trip and that measures were in place for the protection of everyone involved. Strapping himself in with the seat-belt and sliding the blindfold on he felt the vibration of the 4-wheel drive vehicle change and realized they were in motion, leaning back he tried to relax without keeping track of the turns. He hoped he wasn't going to get motion sick from "flying blind" as it were.
As the minutes passed he felt his nervousness increasing and by the time the motion of the car stopped permanently and the engine was turned off he was starting to wonder just what the fuck he was getting himself into. Freakin' rewards had BETTER be commensurate with experience...no 'performance' that was it he thought as he heard the door next to him open and he risked reaching up to remove the mask covering his eyes. The driver was no where in sight, but the car itself was parked in front of a large, Victorian style house. A heavy cast iron door knocker hung on the door and he didn't see a door bell. I can still back out, he thought, but I don't have a clue where I am so I hope they take the unsuccessful candidates back to their cars instead of burying them out in the garden.
