1984. My penultimate day at Sacre Cor High School. The day of the leavers’ ball. The farewell service was being conducted, and the headmaster was about to address the school.

Suddenly, the school caretaker burst in. In his hands were two bottles of whiskey. Shit. But were they mine? I wasn’t the only one who had smuggled drink in for the ball, I knew for a fact. They did look like whiskey from where I was sitting.

The caretaker hurried to the front of the school and breathlessly addressed the deputy head. No-one was listening to the headmaster anymore. 

The deputy head rose and took to the stage. The headmaster paused. The deputy whispered in his ear, showing him the bottles.

In a deep, booming voice, the headmaster cried, “Maria D. Come here!”

Shit. They WERE my bottles. I have to confess, I thought. Maria was on her feet, looking afraid. You could cut the silence with a knife. The clip-clop of her footsteps as she walked down the aisle to the stage was the only sound in the hall, which was full of people. 

My heart was pounding. I was desperately restraining myself from standing, confessing that it was I who had put those bottles in Maria’s locker. I hadn’t targeted her specifically. I just needed to hide the booze for a few hours until the ball, and her locker had been unlocked when I’d hurried along the corridor.

The deputy head, meanwhile, placed a chair on the stage. 

“What were these doing in your locker?”

“I…don’t know, Sir.”

“Does anyone else have the key to your locker?”

“No, sir.”

“So you are responsible for it’s contents.”

The head turned to address the whole school.

“Can anyone enlighten me as to how two bottles of whiskey came to be in Maria’s locker?”

Come on you, cissy, my conscience was telling me. Stand up. Own up. 

Out of the corner of my eye, I saw the deputy head had a cane in his hand. No-one else confessed, of course. 

“Please, sir, it wasn’t me!” Maria pleaded, and I guessed she had seen the cane too, which was now passed up to the stage.

“Consumption of alcohol is grounds for expulsion. However, as it is the last day and your general record is good, I will be lenient. You will miss the ball tonight and…”

He flexed the cane and swished it through the air. 

“Bend over and grasp the seat of the chair.”

 “Sir, please…”

“Now!”

Everyone watched, rapt as Maria bent over. The entire schools’ eyes were riveted on her bottom. Last chance. My hand quivered. On some level, I did want to raise it. It was using all my nerves not to stand and confess…

So why didn’t I? Cowardice. To be fair, I knew what Maria was in for. I’d been thrashed by this guy and it was no picnic.

Crack!

The first stroke reverberated around the school. Maria gave a squeal. We all felt that.

Crack!

I couldn’t watch. I felt sick with myself, just pure shame. All I could do was listen as seven terrible strokes echoed around the hall. When Maria stumbled back to her seat, tears running down her cheeks, I couldn’t meet her gaze.

        o0o

In 1994, I was twenty-six years old and working as a lawyer. I was doing pretty well. I had a specialism in medical malpractice. I had bought my own apartment. I was an active uncle to my sister’s kids. Life was pretty good. 

But I had never entirely stopped feeling bad about the prom alcohol incident. Guilt had certainly soured my enjoyment of what should have been a special night. 

And not only of the prom, in fact. Remorse had sat in the pit of my stomach like a monster beneath the water. Usually, it was still and silent, but occasionally my self-reproachment rose above the surface, rattling the bars of the prison I had constructed for it.

And so it would have stayed, except that one winter's day, I ran into Maria in the supermarket. 

“Hello!” she said brightly.

“Hi! Long time no see!”

“Yes, wow, what a blast from the past! How are you, Matheu?” 

I told her I was well, and was glad to hear she was too. 

Since we both had plans to eat out for lunch, we agreed to dine together, and found a nice place where the tapas was good and the beer was cheap.

Maria was doing well too. She was working for an NGO, and got to travel all over the world for her job. 

“So, are you still in touch with many people from school?” I asked. 

“Not really. I was never exactly a social butterfly. And, to be honest, after what happened at the end, I couldn’t look people in the eye for days, and then everyone was on holiday and it was too late. People had moved on.”

“Yeah,” I said, “That was…harsh.”

Maria smiled ruefully and looked down at her plate.

“It was the worst experience of my life. The pain was bad enough, but the humiliation was far worse. I had to bend over and basically present my backside to the entire school.

And I wasn’t even guilty! Stashing alcohol wasn’t like me at all. They should have known that. But the school just thought, well, it is in her locker, it must be hers. It still pisses me off, to be honest.”

“Yes, I understand. Maria…”

I hesitated. Would it make a difference if I confessed? How would she react? The past could not be undone. But it might make me feel better.

“...Maria, it was me. I helped stash the bottles. I was just hiding them until the ball. I just wanted to get some booze for the party…”

My voice trailed off. She was looking up now, straight into my eyes. Her eyes had darkened. 

“Why?” she said quietly, her tone wholly altered,

“What did I ever do to you, Matheu?”

“Nothing,” I said quickly, 

“I didn’t mean for you to get caned. I didn’t target you, I swear. I’m really sorry.”

The most awkward silence I have ever experienced descended. 

To break this awful lull, I asked her, “If I can do anything to make it right, I will. I swear. Hand on heart, I regret it. I regretted it even as I saw you getting punished.”

Maria looked away, apparently staring at the wall. I’d never felt worse. Seeking release from the tension, I got up and went to the bathroom.

When I returned, Maria was gone. But she had paid the bill and left a note on the table. It read, “If you want to make things right, come to 28 Luis Parede Avenue at eight PM on Friday night. I want an hour of your time. M.”

o0o

Guilt is a strange thing. It can gnaw away at your self-image for years and then disappear in an instant. I had wronged Maria, for sure. But, had I been punished at the time, I would not have carried the weight of self-hatred around with me for so long. If only I had confessed, as I had been on the brink of doing, when I was sixteen, ten or so minutes of punishment would have saved me ten or so years of guilt, of self-hatred. Self-hatred that had stymied my search for a life partner, for a better relationship with my siblings, for closer friendships. It seemed absurd, but it felt like my actions on that distant afternoon had affected my entire life up to this point.  

And that was why I found myself knocking on the door of 28 Luis Parede Avenue, my heart in my mouth. What did she want from me? How would I be able to make things right?

Maria opened the door. She was dressed in a little black number, knee-length, with a hint of cleavage.

“Come in, and take off your shoes,” she said. 

I entered. She had me sit down on the couch. Facing me, she spoke.

“An apology is not enough. This isn’t just about the beating I had. It’s about the lost friendships, my tainted memories of school, the fact that the prom-night caning is all that most people will remember me for. You are responsible for this. You need to suffer. I want you as my slave and submit to my absolute domination for one hour. No acts will be performed without your consent. The safe word will be “Zero.” If you agree to these terms, we will be square and, potentially, friends again.” 

I had heard of such mistress-slave relationships, but I had never imagined myself being in one. But I wanted to rid myself of the guilt. And, now that Maria was outlining the idea, I was intrigued. An hour as a slave would be an interesting experience, something that I’d never forget, even if it was not something I’d ever repeat.

“Deal,” I said.

She had me follow her to the next room and, when she stopped, she was standing next to a chest of drawers with a mantlepiece. On the mantlepiece were several implements. I saw a thick leather strap, a weird green thing that looked like vegetable matter, and a small stopwatch. There was also a big, pink dildo.

“I’ve prepared a list of acts on this contract. Cross out anything you do not consent to, and I will not do it. Anything left on is fair game, and strapping cannot be excluded, given the nature of what you did.”

I read the list. It was like a mini-dictionary of a foreign language that I had never heard spoken. Some were terms I had to ask her to explain. Pegging. Figging. CBT. Orgasm denial. Cuffing. Pee play.

Pee play was the first to go. When she had explained that CBT meant ‘Cock and Ball torture’, I firmly crossed it out, but everything else stayed on. 

Maria now reached for the stopwatch. 

She pressed start. The clock was ticking. Immediately, the thought that I was at her mercy made my heart-rate increase and my cock twitch.

“Drop your trousers and underpants to your ankles and step out of them.”

I complied. She surveyed my privates coldly.

“I guess you could call that a dick.”

I bristled. I never claimed to be huge, but I was at least average, as I understood it.

“Come here.”

She was ordering me to step closer to a desk that stood against the wall. I shuffled nearer.

“You are about to experience two punishments at once. First, this will be inserted into your anus.”

She indicated the small, green vegetable that had evidently been peeled for the purpose.

“It’s a fig. It’s smaller than an erect cock, but somewhat more…alive. Agreed?”

I nodded.

“Secondly, this strap will be applied to your backside. I don’t know how many strokes will purge you, but it may be quite a few. Your buttocks will suffer as mine did. Agreed?”

“Yes.”

As soon as I’d said it, she pulled from her pocket a pair of blue latex gloves. Theatrically, she snapped them on.

“Bend over the desk, and spread your cheeks.”

I did so, stretching my body across the desk and feeling my glutenous maximus tighten. 

I felt her gloved fingers part my buttocks. Soon, the tip of the fig was prodding at my sphincter. I spread my legs to ease its passage.

The fig was pressed so that it drove upwards, firmly between my buttocks. 

At first, it just tickled a little. Not an unpleasant sensation, in fact. But a few seconds later, the tingling began to burn, burn like acid sizzling on my skin. The fig was like a fiery chilli in your mouth, as if it were stripping away protective layers of skin and burning raw flesh. My ass felt like I had eaten the hottest chilli ever grown.

And, just as I was about to gasp aloud, the paddle struck my bottom. It cracked across my cheeks and the sound it made was like a pistol. Instinctively, I clenched my buttocks, but that only intensified the burning pain of the fig.

“Ahhh!” I cried.

Crack! A second stroke was delivered, and then a third, a fourth, a fifth…after ten swats with that strap, my entire backside seemed to be going up in flames, inside and out. 

My knees trembling, my bare bottom raw and throbbing, I spoke,

“You only had six strokes!”

This was a mistake. Five more swats, delivered with all her strength, rained down on my backside. I yearned to stand, yearned to defend myself, but I had agreed to submit.

“How is my slave feeling?” Maria asked suddenly.

“Been better,” I muttered. Immediately, the strap smashed into my prone ass. On my bruised and wounded flesh, it was agonising. 

“Oww!” 

“Would you like a break from being whipped, cissy-boy?”

“Yes!”

I felt a touch of latex on my crack, and felt Maria remove the fig. 

“Stand up.” 

I did.

“Turn around.” 

I obeyed. Feeling her look at my crotch and knowing she had seen my bottom, I suddenly felt very naked.

“I want your hands restrained for this. Put them behind your back, please.”

I did so, and she handcuffed me. Then, she walked around and crouched in front of me. Playfully, she gave my penis a soft squeeze. I began to swell.

“If this thing reaches past my teeth, I’ll be surprised. But let’s see.”

Maria knelt and began to play with my cock, which grew hard quickly. Without another word, she opened her mouth and slipped it in. I felt her tongue around my shaft and suction on the head. It felt amazing, and the residual tingling of my bottom added to the effect. 

Maria sucked my cock, and my penis grew harder. The tugging and warmth around my cock made my knees tremble. 

“Would you like to come in my mouth, cissy-boy?”

“Yes!”

“Yes, who?”

“Yes, mistress.” 

“This cock is so small, I feel like I’m flossing.”

I giggled in spite of myself.

“Nothing funny about a small cock, cissy-boy. Probably why you don’t have a wife. This thing could never satisfy a woman.”

She was insulting me, but she continued to suck my dick. Maria was evidently an experienced deliverer of blowjobs and knew just when to escalate the speed and strength. Her saliva had coated my cock from root to stem, and I could feel that, soon, I would come…

“Right, that’s enough of that.”

Suddenly, Maria released my cock and stood up.

“No, please! I was close!”

A tight knot was already forming in the pit of my stomach. I felt a sort of stomach cramp where my orgasm had been denied, similar to an urgent need to pee.

“No! You aren’t done yet, cissy-boy.”

Every fibre of my body was urging me to jerk off to orgasm. I was so close that it hurt. But my hands were literally tied! 

“You will now lie down, on your side, on the towel I have placed on the floor.”

Curious, I complied. I was relieved, at least, that I would not face further strapping, even if the awful knot in my stomach was still there, and my rear end was still sore.

Maria picked up the dildo.

“Let’s see how far up we can get this, cissy-boy. .”

I had heard of this; They called it pegging!

I duly lay down on, my breath short and ragged with nerves. Even though I was on a towel, I could feel the wooden floor press my bony hip. 

What would that thing feel like? Would it vibrate? Surely, if it didn’t feel good, no-one would do it?  

Maria’s gloved hands rubbed lubricant around my sphincter. The tip of the dildo pressed at my ass, as if some heartless doctor were subjecting me to a careless examination.

“Spread your cheeks, slave, as far as they will go.”

Obeying, I felt the dildo penetrate my already-sore bottom. 

Ouch! 

My sphincter had never been stretched so wide.

But I was determined to hold it, determined not to give her the satisfaction of using the safe word. It was slowly inching up my back passage, then being pulled back, then pushed up further. 

Gradually, it grew more comfortable. Thanks entirely, no doubt, to the lube, it was not an entirely unpleasant sensation, in fact. The fake cock was certainly better than the torturous, burning fig, even if it was bigger.

I could feel that my prostate was being touched, and Maria’s touch and proximity were keeping my erection going. I yearned to touch myself again… 

Suddenly, the thing started to vibrate! 

The electric whirring of the machine was almost drowned out, for I could not hold my tongue with that thick faux-penis vibrating in my ass, shaking my sphincter, kissing my prostate. I moaned and groaned with both pleasure and pain. 

My cock grew large and hard again. This time, Maria reached over and, with her free hand, began to jerk my cock. 

“You’re feeling that, aren’t you, slave?” she said with a wicked laugh.

“Yes, mistress!”

She paused to add some lubricant to her hands, pulled my penis with her fist, then squeezed the end. The dildo…well, it felt as if it was in as far as it could go, shaking, whirring in my bowels. I cried aloud again and again. As bizarre as the scene was, I had never felt so present, conscious and alive. Maria’s hand was still jerking and…

My cum sprayed out in a fountain, emptying my balls across the towel and flecking the wooden floor with spots of white liquid. 

At last, Maria removed the dildo. I felt it slither quickly out of my ass. Aware that my hole was gaping, I stood up, rubbing my ass and crossing my legs. My erection withered to nothing.

“For the remainder of your servitude, you are going to worship my pussy. Your tongue is dedicated to my pleasure. You will bury your lips and tongue between my legs, and you will not move until I say so. You will expect nothing in return. Your sole goal is my pleasure, is that clear?”

“Yes, mistress,” I mumbled. I felt small, belittled. Humbled before her.

“You have not earned the right to look at my genitals. You will worship me blindfolded.”

She tied on a black blindfold. Everything became dark.

I heard a chair being moved and some tugging on clothing. I realised it was Maria taking her panties off. 

“Kneel, slave. And shuffle ten inches forward.”

I did so, then I felt Maria’s hands take my head and guide it up to her pussy. It took only one breath to realise how close my face was to her. The scent of her vagina filled my nose with my next inhaled breath. 

A second later, I felt the skin of her thighs pin me there with a pincer motion.

I began exploring her vagina with my tongue, sliding up and down, now rotating in circles. I sucked on her clit gently, breathing shallowly through my mouth as my nose was pressed firmly to her body.

“Slave has a good technique,” she said quietly.

“Would slave like to know what I did last night?”

“Ok.”

“My boyfriend came round and put his dick right where you are now. He fucked my brains out and dumped several loads of thick, white cum where you are now licking.”

I wondered if this was true, or was it just part of the act?

“And you know who elses dick has been there, slave?”

“No.”

“Your sister’s husband, our schoolmate, Manuel D.”

I looked up at this.

“Elena’s…”

“That’s right. I used to fuck your brother-in-law! Best anal sex you’ll ever have, and a good nine inches. Your sister’s a lucky girl.”

I knew nothing of Manuel’s dating history prior to him marrying Elena. Maria could just be spouting bullshit to unsettle me. But, if true, I did not need to know that.

“Slave’s time is nearly up. No more talk. Just eat that pussy. Make me come and I’ll free you.”      

I followed her command. Now that I was the doer and not the done-to, my body was relaxing a bit. The skin of my whipped bottom was stinging less, and my sphincter was resuming its normal shape. The only problem was that the handcuffs were starting to hurt on my wrists. 

But Maria tasted nice down there, and I was beginning to enjoy giving her head. I couldn’t see her, but I could breathe in the scent of her aroused sex. I could feel that her clit was swollen, and it was making me hard again. 

“Up! Yes, right there!”

Maria’s tone of voice was wholly changed. She was breathing harder and speaking softy. When I felt her raise her legs, her thighs now on top of my scalp rather than pinching my cheeks, I knew she was going to come. I licked her firmly up and down, then sucked softly right on her clit…

Suddenly, her body gave a jerk and she cried out, a wail of pleasure that filled the room and must have been heard next door.

Not long after, she pushed my head away. I stayed on my knees, awaiting instruction. She said nothing. I heard a sound that could only be her pulling up her panties. There were footsteps behind me, then a jangling of keys. The cuffs were unlocked. Maria, still behind me, also freed me from the blindfold.

“I have to pee. Get dressed,” she said, and vanished into the bathroom.

I put on my clothes and waited awkwardly for her to return. I needed the bathroom myself. I didn’t ask her permission, but stepped straight in there as soon as she emerged.

Back in the living room, I said,

“Maria, I’m going now. I hope you stay well.”

“Thank you for coming, Matheu. I appreciate that you came to face up to what you did. I hope you feel better.”

“We good?”

“Yes. We’re square.”

We kissed awkwardly on the cheek, the customary farewell in Spain, and I departed. 

Maria and I became friends. Not close friends exactly, but friendly acquaintances, and that was progress. I never sought out a repeat of my femdom experience, but I didn’t regret it. It was certainly an interesting life experience!

But, in the weeks following our femdom encounter, a weird thing happened. I felt better about myself. The guilt that had sat in the pit of my stomach disappeared. And I knew that it was because I had been punished for what I had done to Maria all those years ago. And if the punishment was scarcely like-for-like, my hour as a slave taught me that femdom had it’s uses beyond being a sexual fetish. 

Used properly, it could be a path to making things right.