Story 4 - Handyman
I almost refused to renovate Ms. Englewood's house for her. The fact that I had to call her Ms. Englewood, even after I'd been working there every day for three weeks, was symptomatic of the reason. The work she wanted done was standard and easy to deal with, but her aloof, superior manner really wasn't. She treated me like a servant from the day I first dropped by to discuss the task, and sometimes referred to me as her "maid" – yes, honestly! – in a way that made me suspect she was only half joking. And not just when we were alone, either. And of course, she was demanding. Everything had to be done twice as fast as it could possibly be done, and it had to look twice as good as it could possibly be made to look. She never said please, rarely said thank you, and took for granted my willingness to accommodate the new complications and elaborations that she came up with on an almost daily basis.
And on that very first afternoon, when I told her the job would take six weeks and she puffed on her cigarette and said coolly that that was simply unacceptable, I knew she was going to be a hard client to deal with. Hell, I knew she was going to be a bitch and a slave driver. But on the other hand, she was willing to pay generously, and she was pretty, really pretty, with soft brown hair and firm, gorgeous tits and a face so fresh that I sometimes wondered if she could really be old enough to be a district attorney. And there was something about her demanding arrogance that I found compelling, almost exciting. The worst part was that she obviously knew it.
So I told her that yes, ma'am, I could do it in four weeks if I worked overtime, and she nodded and said with a knowing smile that she was sure I'd make a good "maid" if I really tried. She wrote out my first paycheque right there, locking me into the deal. And then she put me straight me to work. I threw myself into it, that day and every day for the next few weeks, but I could never quite accomplish things to her satisfaction. The paint wasn't even enough, or the window-sill was still just a tiny bit crooked, or I'd left a bit of sawdust on the carpet. Or it was taking too long – that was a big one. By the end of the third seven-day week, it was pretty apparent that one more just wasn't going to do it, and I told her so.
"You said that four weeks would be ample, Cliff," she replied, without missing a beat. "I assume, then, that you haven't been working as hard as you should."
"Ms. Englewood, I've been trying, but –"
"Cliff, you haven't been trying. Or else you'd be on track for finishing in the time frame you told me was possible. I've been putting up with your shoddy work and slovenliness ever since you started, but now I find that you're also lazy and unable to stick to a schedule."
"That's nothing compared to what I've been putting up with," I replied heatedly, losing my temper with her for the very first time. "What about me, huh? You think you can act like a goddamn princess, call me your 'maid', order me around-"
"I can order you around. You're working for me." Her voice was quiet, but so confident and assertive that I didn't even think of interrupting. "You're forgetting who's in charge around here, and you're forgetting your manners. I think a good spanking will serve to remind you on both counts." She gave me a small, almost challenging smile, daring me to protest. I started on a disbelieving laugh and cut it off, abruptly. Despite her smile, she clearly wasn't joking. I looked down at the floor.
"Right. Come into my bedroom, Cliff." As I walked past her into the bedroom she gave my ass a hard slap. Totally unacceptable, even illegal considering the terms of our relationship, but I was too stunned to argue. I just stood before her quietly, looking down. And when she closed the door and told me casually to take off all my clothes, her tone was so compelling that my hands started to obey before I really knew what they were doing. I stripped naked under her watchful eye, just as I'd been instructed.
"Good, Cliff. Now that I've got your attention, you're going to suffer for being so stupid and impertinent as to swear at me and argue with me." She settled into a chair as I stood there with my hands cupped awkwardly over my genitals, not quite able to believe what was happening to me.
"Come over here," she said, in the kind of calm but firm voice that people use with wayward children. "No, stand beside the chair, and put your hands on your head." I could feel my heart thumping in my chest as I stood there nervously while she looked me up and down. And my penis, damn it, was getting stiff and excited under her scrutiny. I couldn't help it. But she ignored my erection and told me to get across her knee.
She guided me into place, pulling me over her lap and telling me to lift up my bottom so that she could position me more suitably. As I lay across her lap with my hands on the floor, I could feel the cool air on my ass and was almost painfully aware of my penis pressing down into the fabric of her slacks. I was desperate to grind my hips into that smooth, stimulating softness, but of course I didn't dare. I was in enough trouble with her as it was. She rubbed her hand lightly over my ass, and I tensed in anticipation of what was to come. But the first few rhythmic, methodical smacks across my bottom weren't too hard to take. It was only a bit later that I gave my first little cry of pain, when my ass was warmed up a bit and she gradually increased her tempo until the blows were coming mercilessly fast and hard. My bottom seemed to bounce up and down in time with her hand.
"Does that hurt, Cliff? I'm glad it hurts. You should be ashamed of yourself." She varied the pace of the spanking so that I never quite knew what to expect. One minute she would slow down and smack me harder on both cheeks and then across my bottom, pausing between blows to really let the pain sink in. Then, speeding up, she would sting me with a flurry of lighter slaps which left no part of my bottom untouched. My ass was burning, I was crying and squirming in pain, and eventually I couldn't help kicking my legs and asking her to stop. But she didn't.
"Lie still," she said curtly, and cinched her grip tighter around my waist. "I won't tell you again. You should count yourself lucky that I'm using my hand instead of that big leather tool belt you brought in here. Next time I won't be so lenient." So it went on and on, for a good ten or fifteen minutes, before she finally told me that I could get up off her knee. I clutched my throbbing ass, devoid of all modesty as my erect penis waved in the air in front of me. And Ms. Englewood just sat there, arms folded across her chest, with a smug and satisfied look on her face. But my ordeal wasn't quite over, because she told me to stand facing the wall with my hands on my head. I obeyed, still sniffling, and knew better than to glance over my shoulder when I heard her leave the room. The door remained open, I suppose so that she could keep an eye on me.
A few minutes later she was back. I felt her cool hand on my ass, rubbing the flesh she had just smacked raw. "Now, Cliff. You're going to be a good boy from now on, aren't you?"
"Yes," I sniffed. "If you say so."
"I do. You're going to sharpen up and work a lot harder, unless you want word of what happened between us today to get around. I'm going to be watching you like a hawk, and I'm not going to tolerate any more laziness or untidiness. You've exhausted my patience. I've got a leather paddle in my closet that I had specially made for dealing with assholes like you, and I'm going to use it to make you sorry if I hear one more word of backtalk out of you. Now get dressed."
And she swept out of the room, leaving me standing naked with the cheeks of my ass smouldering with pain and the ones on my face stained with fresh tears. But I was also still incredibly, absurdly turned on. I looked at myself in the mirror again and saw that my bottom was still a hot, vivid red. I couldn't resist taking hold of my stiff penis and slowly masturbating in front of the mirror as I rubbed my bottom with my other hand and thought about what had actually happened to me in this room only ten minutes earlier. I felt shell-shocked, unable to quite believe it, but I had the pain and the redness to remind me that the spanking had been all too real. I only wished that it was Ms. Englewood stroking me, her hand rubbing back and forth along the length of my hard cock to take my mind off the lingering pain. Or hell, even spanking me again, but dressed differently, in a low cut dress that showed off those perfect tits I could never help staring at even through her full blouses. She would massage my hot ass afterwards, as I lay on her bed, and then lift her skirt to tease me just a little. Her ass would be creamy white, not red with spanking, and oh so smooth...
The thought made me grip my penis tighter and masturbate faster until I was close to ejaculating. Just as I was going over the edge I heard Ms. Englewood clear her throat, right behind me, and I froze. She quickly stepped up and grabbed my asscheeks with her hands. "Finish," she hissed as she began to knead the swollen, red flesh under her fingers. I masturbated faster, looking at both of us in the mirror, her face flushed and grinning with delight. She scratched and gripped my ass so hard that I started to moan in pain. And it was at that moment that I came, shooting jets of semen all over the pristine surface of the mirror. I was hers.
"Cliff," she said after a moment.
"Yes, ma'am?" it seemed natural. "I'm fired, right?"
"Goodness, no. In fact, you can have three more weeks to finish the project, all the time you originally wanted. But you're going to work hard, long hours. On the renovation and – anything else I might want from you, my little maid."