"It's gonna hurt, honey," Miss Maggie said. "I'm not tryin' to scare you, but I won't lie to you either. It's gonna hurt."
Everybody knew that she could be cruel to her lovers, when she wanted to be. But whatever else you could say about Miss Maggie, she was always honest.
"I'm not a malicious woman, but I've got my needs," she continued. "Sometimes, every once in a while, I need to watch a man suffer. Hard and long, until he can't take any more. If you ask me to stop, I will—but if you're gonna spend the night with me, you need to know what you're in for. So I'll tell you again: it's gonna hurt. And I'm gonna enjoy it..."
She never raised her voice, the first time she used the whip on me. That wasn't the worst part about that night—not by a long shot. But it unsettled the hell out of me.
There was no anger in her voice, as she calmly explained how she planned to punish me. But there was no mirth or joy either. If it hadn't been for that little mischievous smirk on her lips as she watched me undress, I might have wondered whether she enjoyed it at all.
When she said those words to me, I faced the far wall in her bedroom, where an x-shaped bondage cross stretched from the floor to the ceiling, equipped with four leather cuffs for my wrists and ankles. I wore nothing but a plain pair of grey briefs, already growing tighter against my buttocks as my erection began to swell. She approached me from behind and took my wrists in her hands, gently guiding them upwards to bind them to the ends of the cross. I felt her warm breath on the back of my neck as she pulled the cuffs tight, and goosebumps rose along my naked back.
As soon as my hands were tightly bound, she reached down to give my backside a playful pinch. As I shifted with discomfort, she slipped one manicured finger into the waistband of my briefs, and slowly—very slowly—she lowered them. My swelling erection twitched and bobbed as I felt my underwear side down to my ankles. Though I couldn't see her unblinking gaze or her amused expression, I felt Miss Maggie's eyes sizing up the contours of my body: my slim thighs, my well-muscled back, my flexible arms, and my taut behind. It was the first time she had ever seen me naked, and she savored the moment; naturally, she didn't wait for permission.
She was the first woman who'd ever truly dominated me, but I had always known about my tendencies. Hundreds of times since my eighteenth birthday, I'd dreamed about nights like this: being stripped naked under the watchful eye of a dark-haired countess, who waited in the shadows to discipline me with whips and chains and riding crops. My cock twitched at the thought of Miss Maggie watching me, but I had never known the sting of a whip. Was I ready for the real thing
?
Everybody who'd met Magnolia Hayes knew that she was a businesswoman; her fine multi-floored manor house, nestled amid the Spanish moss of an old Mississippi plantation, spoke to that. The woman had enough money to get what she wanted, and she was accustomed to paying for the best. But even in matters of pleasure, she was a consummate professional. The first time she proposed our little "arrangement," she didn't bother to flirt with me; she invited me over for tea, calmly outlining her expectations as we sat at opposite ends of her dining room table.
"If you say yes, you'll be agreeing to complete and total submission," Miss Maggie had said. "I'll call you when the mood strikes me, and you'll arrive back here, promptly at six o'clock. From there, the night will proceed according to my desires. I'll recognize your boundaries and limits, and I'll stop if you ask me to—but beyond that, your fate will be in my hands. Can you handle that, Joe? Think hard, now."
I answered "Yes" after barely a moment's hesitation. She gave a little giggle of amusement, seeing my boyish eagerness. At a few years under 40, Miss Maggie was more than a decade older than me—but with her money and her well-aged beauty, she didn't bother relegating herself to lovers her own age. She made a hobby out of courting younger men, and seemed to relish their youthful enthusiasm. When she got busy with her whip in the bedroom, there was something in her brand of discipline that reminded me of a schoolmistress.
A blindfold was her last touch of dominance. I tried to be polite when I was around Miss Maggie, but I knew that my eyes often lingered just a little too long on her body when we met; she knew that I loved the sight of her, and she got a little sadistic thrill out of denying me the things that I craved. But as she slipped the blindfold over my eyes and pulled it tight around my head, I saw her body in my mind as a series of snapshots: the curve of her hips like a well-built violin, her slim neck glistening with expensive pearls, and the graceful sway of her ample bottom under a tight sundress.
Her hair was dark and lustrous, arrayed in a playful waterfall of elegant curls that fell around her face like a wreath. Her face was cherubic, with a distinctive rosy glow in her cheeks. Her body was pleasantly plump in all the right places, but she knew how to hide her curves under immaculately tailored dresses. She dressed in summer colors that night, her dress patterned with lilies and irises.
She didn't bother to give me another word of warning before she turned her whip on me. I heard her footsteps on the floorboards as she walked towards me—but until I felt that first stinging blow, I didn't even know that the whip was in her hand.
It came down in a fierce diagonal slash, the leather tails raking me from my shoulder blade to the small of my back. Every tail was fixed with a little leather knot, just hard enough to scratch at my skin. The first blow caught me off guard; my nerves singing with pain, I felt my knees go weak, and I shifted on my feet as I clenched my hands tight.
Miss Maggie put a hand on my shoulder to hold me steady.
"Stand up straight, honey," she chided. "You can yelp and moan all you want, if it helps—but stay still."
I didn't even have a chance to say "Yes, Ma'am," before she brought the whip down again, even harder than before. She kept it up for a solid ten minutes at a time, beating me at a fast clip. Whenever she got tired, she gave me a brief respite from the whipping as she pinched, squeezed and slapped my bare ass, and reached around to stroke and fondle my twitching cock—teasing me until I felt it throbbing with arousal and drooling with pre-cum.
"Your body belongs to me tonight, Joe," she said mischievously. "And I can think of all sorts of naughty uses for it. There are a lot of ways to torture a man—and I've got a hell of an imagination."
Then she went to work with the whip all over again, bringing it down left-to-right, then right-to-left, until the fresh welts made a wide crisscrossing "X" on my back. As it went on and on, my breath grew heavy as I struggled to keep my legs straight, and I found myself moaning rhythmically with mingled pain and arousal as my cock grew harder.
I didn't dare relax until I heard the sound of a drawer sliding open as she tucked the whip away. My muscles grew tense when I felt her hand on my wrist as she undid my bonds. After enduring a good long whipping, I was too weary to resist when she pulled both of my hands behind my back. But goosebumps rose along my back when I felt a tight ring of hard plastic clamp down upon my left wrist, then my right. She'd put away the whip, but brought out a pair of handcuffs.
As soon as she'd undone the bonds at my ankles, she draped her arms around me and pulled me in for a tight hug from behind. Through the thin fabric of her tight sundress, I felt her soft breasts pressing against my back; her hair was fragrant with oil, smelling faintly of brown sugar and ripe peaches. With manicured fingers, she caressed every part of my body she could reach, brushing her hands along my chest, my thighs and my stomach. But then her right hand strayed to my exposed balls, and she squeezed them hard enough that I winced.
"You took that well, honey," she said. "Maybe a little too well..."
She slackened her grip, and I let my breath go. But she kept her fingers tightly wound around my engorged cock as she led me to the bed.
"I like a man who can take a whipping without a complaint. But sooner or later, I want to hear you beg for mercy. And before this night's over, I think you will..."
• • •
For forty-three days, I wait on her call. When it comes, I don't know whether to be excited or apprehensive.
I still remember the terms of our agreement by heart.
"I'll call you when the mood strikes me, and you'll arrive back here, promptly at six o'clock,"
she had said. But when her text message reaches my phone, it plainly says
"Saturday, four o'clock."
At first, I wonder if she made a mistake—but I know better than to question Miss Maggie's orders. So I reply with a simple
"Yes, Ma'am."
Four o'clock... She's summoned me two hours early. But why?
Knowing Miss Maggie, I doubt she's that eager to see me. And with all the time she spends running her bustling little café, she never has many free hours to spare. As busy as she is, she's always selective about how she spends her leisure hours. She'd never change her plans on a whim. She'd never call me on a whim, either. Whatever she's got in store for me, she's had time to plan it.
When Saturday comes, I shower early. Naked and towel-dried, I give myself an hour in the bathroom to calm down, breathing deep breaths as I keep my eyes riveted on the ceiling fan. Most mornings, I can't resist the urge to touch myself in the shower—but Miss Maggie's instructions were clear.
"You're forbidden to cum without permission, as long as our little arrangement still stands. And I only give permission in person. As long as we're doing this, you'll have to get used to a little bit of frustration. But I promise you: I'll call on you, before too long. And if I'm feeling merciful, I might just give you some relief..."
As soon as I remember those words, I can't help picturing Miss Maggie in her tight little sundress, staring impassively at me from across the length of her bedroom. And as soon as I think of that, I feel my cock go rigid—though I resist the temptation to stroke it.
Forty-three days is a hell of a stretch. I can't remember the last time I went this long without an orgasm. I've always had my fantasies about dominant women—but fantasies are comforting things, and they can end at my leisure. This powerlessness is a new sensation. Still, there's something oddly thrilling in it.
For forty-three days, I've done my best to keep my composure and my dignity, but I've stolen plenty of unnecessary glances at my phone, always daring to hope that the call might finally come. Even in calm moments, I've felt my mind running wild with infinite possibilities, always braced for something unexpected. Whatever's going to happen tonight, I know that Miss Maggie knows more about it than I do. And I'm sure that thought satisfies her.
I dress in khakis, a simple t-shirt, and a light sweater, and leave the house with two hours to spare. As I make my way through the sun-dappled countryside—resplendent in the last days of Summer—I take my time on the back roads, letting the sound of the radio calm me down.