Jenny

Jenny was always fascinated with methods of punishment used throughout history, and it inevitably led her to study law and correction. It often worried me the interest she showed in the more gruesome punishments inflicted over the centuries, usually those involving pain or humiliation. Really, the job she had aspired to within the Department of Correction suited her right down to the ground. I had always feared for the poor souls who may end up being dealt with by her if she succeeded in those aspirations. Don’t get me wrong, she was a lovely person: intelligent, caring, compassionate, gorgeous and so sexy. To look at her, and even spend time with her, you wouldn’t know what went on inside her head.

Of course, I had a massive crush on her and she knew it, so she used her teasing nature to flirt with me whenever she could. I knew she wasn’t interested in having any sort of relationship with anyone as she was so focussed on getting her career moving. I could understand that, but I wanted to keep our friendship alive hoping that when the day she was ready to start dating arrived, I’d be in pole position.

It was only months after she’d completed her education that she applied to become a Correction Officer. She had quickly gone through the various stages of the recruitment process: paper sift, physical test, aptitude test, background checks, final interview and even the medical. Applying for a position in the Department of Correction required the hopeful party to have a clean record, and Jenny certainly did, until she finally received official confirmation her application was successful.

We’d all gone out to celebrate her success with a meal, but not having planned to drink much, some of us, including Jenny, went in our cars. When we’d finished in the restaurant, everyone drifted off home leaving Jenny and I to wind up the evening with a quick drink in a bar. However, we ended up having more than we intended, Jenny in particular.

When we left the bar, she could hardly walk in a straight line, so I was amazed and shocked when she approached her car. I was intending to leave mine until the next day when I’d sobered up, but there was nothing I could do to put Jenny off driving herself home. Refusing a lift from her, I helplessly watched her drive away, her car swerving as it disappeared down the street and around the corner.

First thing next morning, my phone rang; it was a frantic Jenny. I’d never heard her so upset.

“Michael. Michael. What am I going to do?” she shouted down the phone.

“Slow down, Jenny,” I said, struggling to wake myself up.

“I’m in so much trouble.”

“What trouble?” I rubbed my eyes and lay on my back.

“I can’t explain over the phone. Can I meet you somewhere?”

“Er, yes, if you want.”

“Michael. How good a friend are you?”

That got me worried.

She looked very dishevelled, mainly due to her hangover, when I saw her half an hour later in the local coffee shop. She explained quietly, but tearfully, how, on her journey home, while very much under the influence of alcohol, she’d managed to scrape her car along a line of parked cars. If she’d stopped and reported the incident, she would have been discovered to have been well over the drink drive limit, and lost her dream job before she’d even started.

Making a quick decision, she’d driven on, managing to get home without any further incident. It was a gamble she’d taken, because if caught, she would have been in even more trouble for failing to stop and report what she’d done. Her only hope was that nothing would be picked up by street cameras.

She reached across the table and held my hands. “I’m terrified I’m going to be caught and I’d be in so much trouble. I’m a Correction Officer, a member of the Justice system even though I don’t officially start until tomorrow. They’d come down so heavily on me, and I’d lose the job I worked so hard to get.”

“You’ll be ok,” I said, trying to comfort her. “Just keep your head down, they’ll not find out.”

“How much of a friend are you, Michael?” she asked, tearfully.

There was that question again.

“I like to think I’m a special friend to you, Jenny.” I so much wanted to be more.

She hesitated as if nervous of something. Then I discovered why.

“If I needed you, would you take the blame for me, Michael?”

“What?” I was shocked.

“If they find out it was my car that crashed into the others…”

“They won’t find out,” I said, trying to avoid the answer. “Where’s the car now? You have hidden it away somewhere, haven’t you?”

“Of course I have. It’s in my garage where no-one will see it scratched and dented. Please, Michael. Just in case they somehow find out it was my car; would you tell them it was you who borrowed it. You’d only have to say you accidently clipped some parked cars, but didn’t stop because you panicked.”

“What about the trouble I’d get into?”

“You won’t lose your job, you’re a freelance writer. No-one was injured, so you’ll just get a fine, that’s all, which I’ll pay, of course. Please, Michael.”

“I don’t know…”

She gripped my hand harder, then began to stroke it gently. “I’m begging you; I promise I will make it up to you, any way you like.”

I was thoroughly infatuated with this girl, and for her to make such an open ended offer like that, pushed me over the edge. “Ok,” I agreed, tentatively. “As a last resort.”

The authorities would probably never discover it was her car that was involved.

Unfortunately, the street cameras clearly picked up the whole incident, and the Law Enforcement Officers were even waiting for Jenny when she got back home.

I got a call from her as soon as the LEO’s left her apartment a couple of hours later. Fortunately for her, the pictures hadn’t shown who was driving, unfortunately for me, she told them it was I who had borrowed her car and caused the collisions. I was stunned she’d actually gone through with passing the blame on to me. She told the Officers I’d confessed to her what I’d done, and she’d just been with me trying to get me to do the right thing and come forward voluntarily. She sounded very upset that she’d dropped me right in it.

Not ever having been in trouble with the law, the various penalties and punishments weren’t things I thought of much, but I did know punishments were a lot more severe after the drastic society upheaval of three years earlier. Massive changes had taken place which had included a huge shift in the so called ‘equality of the sexes’. Things had swung very much in favour of women. Penalties for men were now much heavier than penalties for women committing the same crimes. I was very concerned how this would affect me.

Just half an hour after Jenny’s call, there was a knock at my door. A male and female LEO asked me to confirm who I was before asking if I had driven Jenny’s car the previous night. I wanted to say ‘no’ but couldn’t bring myself to betray my friend. They took an alcohol reading there and then which at least showed only minimal levels in my system, nothing that would prove me over the limit the previous night. I was asked to accompany them to LEO HQ.

Jenny arrived while I was sitting in the reception area waiting to be interviewed. Many of the LEO’s acknowledged her presence, with a couple of them chatting to her; they must have known her from her frequent visits during her assessments. In fact, while my details were being recorded, I heard a senior female Officer speak to Jenny, telling her she was looking forward to seeing her in work the following day. Even though I was in a predicament, Jenny was still able to give the Officer a broad smile and a cheery ‘thank you’.

We were both invited into the interview room and given seats; me on one side of a desk, Jenny sat on the opposite side next to the interviewing LEO. She was a woman in her thirties, attractive but showing no softness to her character as she glared at me. She spoke to Jenny with a little more friendliness, commiserating with her that she had been a victim in the incident for which I was to be charged. In their brief chat about her starting work the next day, I discovered Jenny had applied for a role that included administering corporal punishment.

At this point it’s probably worth giving a little more information regarding the changes introduced during the social and penal reforms. There were now two separate courts: male and female. As well as custodial sentences and fines, courts could now give physical punishments to male offenders with a whip or cane, with emphasis not just on administering pain, but with the added sting of humiliation. Perpetrators had to strip naked and receive their punishment from a female LEO in the presence of other female Officers.

I sensed Jenny was seriously embarrassed about the situation she’d got me into, but it had happened, and to go back on our little fabrication would destroy her career and land her, and me, in court facing much more serious charges of perverting the course of justice.

Miss Karen, the name tag on the Officer’s dress revealed her identity, read out the four charges: Careless driving that caused a traffic accident. Failing to stop after a traffic accident. Failing to report a traffic accident. And driving a vehicle without the owner’s permission.

At the final charge, Jenny did stick up for me, telling the Officer, as friends, we had an open agreement allowing us to use each other’s car any time we needed to without seeking additional permission. Miss Karen didn’t seem too happy with that and advised Jenny she shouldn’t be so trusting as; “Look how that turned out!”

Reluctantly, she removed that charge, and asked me if I wanted to contest the three other charges or admit my guilt. To plea guilty there and then meant I could go home, and they would contact me to confirm the verdict, informing me at the same time what punishment I would face. I was expecting a fine which Jenny would be paying, of course, so the only realistic option was to accept.

Jenny was then asked how she was affected by the crime and she tried to play it all down: error of judgement, I was a good friend, no one got injured, that sort of thing. Miss Karen wrote it all down and I was released. The charges didn’t seem that bad after all, and as long as Jenny paid the fine, which I’m sure she would, that would be the end of the matter.

Later that night, Jenny came to my apartment. She was unbelievably sorry, grateful, overwhelmed with my friendship, and determined to pay me back for what I’d done for her. She gave me a massive hug, holding her body tight to mine for quite a long time, so long I was getting aroused, and I’m sure she could feel it, which was why she let go. She was a very sexy girl.

We sat down and she explained to me what had been said after I’d left. I was expecting it to be about me and the charges I’d just accepted guilt for, but no, it was all about Jenny. She would be starting work the following day, and it would be only a few days before being placed on the punishment rota, administering canings. She was so excited telling me how she couldn’t wait to get started. As a new LEO, she would be given the more petty criminals to deal with until her strength of caning increased to a more severe level. She told me she’d been practicing at home with a cane on a pillow so she was ready to give severe canings as soon as she was allowed. Apparently, every cane stroke had to be given full force by the LEO, the number of strokes was determined by the court according to the crime. She would also be given instruction and training for the first few days on how to use a cane to best effect in order to inflict as much pain as possible.

I asked if there had been any mention of the punishment I’d get, but she didn’t know, and didn’t seem too interested, saying it would only be a fine. She stayed for a couple of hours, she flirted with me a bit, thanked me again, told me how grateful she was again and promised she’d make it up to me… again. She gave me another long hug which triggered another erection before going home.

Three days later, my court email arrived. My crimes were listed, my guilt was confirmed, and my sentence given: My mouth dropped open in utter and complete shock… I was to receive a caning… twenty five strokes on my bare bottom… and that was in addition to the two hundred credit fine!

I couldn’t believe it. I rang Jenny straight away.

It was a strange conversation; she was apologetic and sympathetic, but there was something in the way she was speaking to me that got me very concerned. She asked if she could come round to see me. When she arrived, she was very sheepish, and eventually she told me why: Because the crime was partially against her, a Law Enforcement Officer, they decided to add the caning on to the fine. Not only that, and this is where she became very embarrassed, the administration staff had done her the favour of making it her first punishment assignment.

As she told me this, she wrapped her arms around my waist and hugged me. “I’m so sorry Michael, but I’m the one who is going to cane you.”

Not only had Jenny committed the crime for which I’d taken full blame, she was the LEO who was going to punish me for it. I was going to have to strip naked before her and receive a caning from her. The humiliation would be unbearable.

Then she explained more about the punishment. Apparently, the female LEO’s dress provocatively and try to arouse the man when he’s naked. For a man to get an erection in front of a female Officer is considered to be rude and insulting behaviour. It is even classed as a sexual offence and results in the punishment being doubled. I was shocked and seriously worried about this, and I told her how attractive I found her and I wouldn’t be able to resist getting an erection in her presence if I was naked.

All she said was: “I’m sorry, I don’t know how I can help you.”

“You could tell the truth,” I said, quietly.

“Oh, Michael, I couldn’t do that now; we’d both be in so much more trouble. I’d lose my job and we’d both get much stiffer sentences.”

I nodded in agreement; she was actually correct.

I turned up at the allotted time, and reported to the registration desk where an attractive young woman read my notes on screen and smiled so sexily at me. It seemed what Jenny had told me about them trying to turn the men on began with arrival. I was directed to punishment room B and told to strip naked and leave my clothes in the basket provided.

The room wasn’t much bigger than the standard six foot by eight foot prison cell with a high ceiling, all painted grey with a small window high up on the far side. The only furniture was a raised table and a single chair. I stripped and placed my clothes in the wicker basket and stood waiting on the cold tiled floor. After about half an hour there was a knock on the door and a stunning twenty something woman walked in wearing a short, tight black dress.

She must have been specifically chosen for this job because she had the most perfect, slim, shapely body. The dress was official uniform, as embroidered just above her breasts were the letters, LEO, and her name, Sarah. A pair of handcuffs hung on the black belt wrapped around her slim waist. She came over and placed her soft, warm hand on my back which caused my flesh to tingle.

She gave me a sympathetic smile. “Have you ever received corporal punishment before?” she asked, almost seductively.

“No,” I answered. I didn’t want to get into conversation with her as I wanted to avoid eye contact. She was as sexy as hell, but my penis was behaving itself.

“Just to warn you, if you didn’t already know, if you get an erection at any time before your punishment begins, the number of cane strokes will be doubled, and I’m sure you don’t want that to happen.”

“No,” I said.

She looked down at my penis. “It looks like he’s being good, or maybe I don’t turn you on. Sorry, only joking.” She giggled.

I wasn’t amused, especially when I felt the slightest twitch of my penis.

She stood in front of me, our faces inches apart, her cleavage was exposed and she looked up into my eyes. “It really isn’t fair to put a man in a situation being naked around young women and expecting them to not become aroused,” she said so sexily, “but rules are rules and I’d hate your caning to be doubled on my account.”

By now, my penis really was beginning to stir. ‘Please no, please no,’ I thought, trying to concentrate. Using all my resolve, I just about managed to hold back, despite her holding my gaze for a few seconds. It was going to remain a struggle, and it was only then that I realised I should have relieved myself before I’d set off from home, that was a basic error.

“Well, it looks like you really have excellent control over yourself,” she said, sounding a little disappointed. “Come along, follow me.”

She turned and walked sexily out of the cell with me right behind her trying to avoid looking at her gorgeous tight bottom as it swayed from side to side in her figure hugging dress.

The room I was led into was quite large, the only furniture was a punishment bench. Standing close to it were three clothed women. The woman who had interviewed me, Miss Karen, another, younger woman, and between them was Jenny.

As soon as I laid eyes on her, I lost control. She was utterly stunning wearing a short dress uniform that showed off her shapely figure. Her strawberry blonde hair lay seductively on her shoulders and her sexy lips hinted at a Mona Lisa smile. In both hands she held a long, vicious looking cane that she bent threateningly as she looked at me like a predator eyeing her prey. All my resolve melted away in that moment and my penis grew to full erection where I stood; there was nothing I could do to prevent it. Even the humiliation I felt being naked was adding to my uncontrolled arousal.

It was Miss Karen who spoke: “I see we have another male who cannot control his lust. You are here to be punished,” she said to me, sternly, “not to give in to primitive arousal just because you’re in the presence of females.”

“I’m sorry,” my words croaked from my mouth.

“I’m sure you are, sorry that you’ve just had your punishment doubled.”

I looked at Jenny, whose face remained hard and uncommunicative, but she was looking at me. I searched for compassion in her face, after all, I didn’t deserve to be in this position, I was here because I was covering for her. I don’t know whether it was my totally vulnerable position, but I thought I could sense a little excitement growing on her face, and by the way she was gently flexing the long cane she held in her hands, I actually started to think she was looking forward to what she was about to do.

“As this is a slightly unusual case, given that you are here because you committed a crime partially against one of our own, we have arranged for Miss Jenny to carry out your punishment. It may interest you to know also, I was going to issue you with twelve strokes of the cane, but after consulting with Miss Jenny,” she smiled as she directed her hand towards her, “she appealed for your punishment to be increased to twenty four strokes. That shows admirable commitment to the job considering she sees you as a friend.”

I looked at Jenny with horror, but she remained unmoved. “Why?” I asked, quietly. I knew I would get no answer from her.

“And as I said, the caning will have to be doubled due to your indiscretion,” Miss Karen added.

Before I had a chance to speak again, not that I knew what to say to the girl who had betrayed me, the younger girl with the name tag, Miss Sarah, took my arm and directed me to the punishment bench where she told me to climb on in a kneeling position and bend over the leather padded equipment. She strapped my arms, legs and back very securely so I was completely immobile. Then she stepped in front of me, her back against the wall.

From my position with my head face down, I could only see her short, black skirt and her long legs smoothly covered in black tights just a few feet away. Other footsteps approached; Miss Karen stood to my right while Jenny stood to my left. I turned my head to look at her and caught her eye. I was sure it was for my benefit that she swished the cane down in the air creating a piercing shriek, wow, that didn’t sound good.

“Miss Jenny, the original punishment will begin with twenty four strokes on his bottom. Begin!” Miss Karen said sharply.

Jenny positioned herself, placing the end of the cane gently on my bare bottom to gauge her reach for maximum effect. I gripped the side of the wooden frame knowing this was going to hurt. It did. The first stroke whistled through the air and smacked hard across my exposed buttocks. In that first briefest of moments, I felt nothing, but then the pain seared through my bottom as though it had ripped me in half. I shouted out, it was something I had planned on not doing as I didn’t want them to know how much it hurt me, but I couldn’t help it. I even struggled against the leather straps to no avail.

Miss Karen counted: “One.”

Before the pain had even half dissipated, the second stroke whipped across my buttocks adding to what had gone before.

“Two.”

I couldn’t cope with the pain, it was too much.

“Please no more,” I begged. The third hit as I finished my plea. “Please, no,” I yelled.

“Three.”

Jenny continued to administer the strokes hard and true at the same relentless pace with Miss Karen continuing to count. Neither she or the other two women gave any acknowledgement to the distress I was suffering; my pleas falling on deaf ears. It didn’t get any easier, it was the most painful experience of my life and I didn’t deserve it. To make it worse, the person causing it was the one who actually deserved it.

I was saving her career and being severely punished by her for doing so. I was losing count of the strokes as each followed the previous. The pain was unrelenting, but I was becoming so resigned to it, I was hardly even shouting out. Then it stopped, the last stroke had landed, we had reached twenty four, and I relaxed on the leather padding, exhausted.

I was half hoping they would show mercy and not go ahead with the additional twenty four strokes for me having an erection. It had easily subsided by this time. But no, they gave me a five minute break before the whole punishment was repeated; twenty four more strokes on my bottom.

Yes, the pain was worse. I was in a daze with tears rolling down my cheeks by the time the last stroke whipped mercilessly across my bare buttocks. When it was announced my punishment was over, I was released and told to stand, staggering and almost falling before Miss Karen and the other guard held both my arms to steady me.

I was escorted back to the small room where I’d stripped earlier, and found a nurse waiting for me. She was dressed modestly in a uniform, and as our eyes met, she smiled sympathetically at me. In some ways, it was more humiliating lying face down on the examination table while this woman inspected my bottom and applied antiseptic cream to my injuries. She told me to remain face down on the table for half an hour to allow the treatment to work.

Once I was given the all clear, I was allowed to dress and was escorted from the room to the building main lobby by the woman who had first greeted me in the cell. As I left the building, I half expected Jenny to be waiting outside, but she was nowhere to be seen.

When I got home, my bottom ached badly every time I sat down, stood up or did anything that involved stretching or twisting the flesh of my buttocks. Looking in the mirror, I saw my bottom was a mass of deep red, horizontal weals neatly arranged from the top to the bottom of my buttocks with deep bruises spread around an even wider area. I dreaded to think how painful it would be the following morning when the bruises came out fully.

It was much later that same day, after lunch, an afternoon nap and a microwaved evening meal, that my doorbell rang. Finally, it was Jenny; she asked if she could come up to my apartment. I was nervous seeing her so soon after what had happened, although I thought it only right that she should make the first move in contacting me. But I knew it was still going to be an embarrassing meeting as, not only had she seen me naked, she’d also seen me sexually aroused.

“Hello, Michael,” she said, sounding just as embarrassed as me.

I nodded my head and stepped away from the door allowing her to enter.

“It’s only just sinking in what you did for me today,” she said, sheepishly. “I can’t believe how far you went, and what you sacrificed for me. It must have been terribly humiliating having to go through all that.”

I shrugged my shoulders not knowing what to say to her. “Not to mention, painful.”

She winced. “I honestly didn’t expect it to be that bad for you.”

“You asked for my sentence to be increased,” I reminded her.

She screwed her face up in dismay. “I know, I know. I just thought it would look good for me.”

“From what your boss said, it sounds like it was very good for you.”

“I’m totally new to this, you’re the first man I’ve caned. I honestly thought twelve strokes wasn’t too bad, and asking to increase it to twenty four… I thought it’d be ok.”

“But then I got aroused and it got doubled.”

“I know, and it was too late to do anything about it, but I did warn you that would happen. I had to go through with it. Did it hurt that badly?”

I gave an ironic laugh. “What do you think?”

“I am so grateful for what you did, Michael, I really and truly am. I just can’t believe how far you went to protect me.”

“I think a lot of you, Jenny; that’s why I did it. You’re my best friend.”

“I think we’re more than friends.”

I looked quizzically at her. “You do?”

She took off her short leather jacket and threw it on the chair. Then she undid her blouse and took it off. Her lovely naked breasts stood firm and proud before her, and despite the pain I was still in, I felt my penis begin to stir. She kicked off her shoes and unzipped her jeans, dropping them to the floor; she was standing before me with just her panties on. They didn’t remain on though as she slipped her thumbs into them before sliding them to the floor.

“Michael, I want to be more than friends with you.”

Leading me by the hand into the bedroom, we stood facing each other. She reached up and kissed my lips, her hands gently caressing my face. I couldn’t help but respond, holding her closely, my hands feeling the softness of the flesh of her bare back. I was so desperate for her at that moment, and I sensed the feeling was mutual.

She pulled away and lifted the t-shirt over my head and ran her soft hands down my chest to my trousers. She knelt down, and with her eyes fixed on mine, she undid the belt and unbuttoned my trousers, pulling them and my shorts down to the floor. My penis stood upright, hard and desperate to feel her touch, her face was inches away and I begged her with my eyes to take it in her mouth.

When her lips wrapped around the throbbing end, I couldn’t believe the sensation of pleasure I felt, and when her tongue ran along the underside of the stem as she stroked it with her hand, I felt I was not going to last long. She was so skilled using her mouth as well as her hand, but she was careful not to push me too far. It was just enough to tease my arousal edging me closer to where she wanted me. When she decided I’d had enough, she climbed onto the bed beckoning me to climb on top.

My penis was rigid, precum leaking onto her thigh. As her legs parted for me to enter her, I knew I wanted to taste her first, so I eased myself down her body, kissing her breasts and stomach as I moved, finally reaching the soft folds of her pussy. The scent of her arousal reached my nostrils and as my tongue gently lapped at the soft, damp flesh of her most private part, a sound of pleasure escaped from her mouth.

“Oh, Michael,” she whispered. “How can you be so good to me after what I did to you?”

I gave no answer, but continued to lick her succulent, sweet sex, giving pleasure to the woman who had so abused me earlier that day. It was a dream I’d had for a long time; to bury myself in her special place, to taste her sweet nectar, to please her the best way I knew. I teased her at first, deliberately avoiding her clitoris, to give her a slower approach to the climax I wanted her to enjoy.

With gentleness, I concentrated on the soft folds, quickening as I felt her pleasure growing. This was what she wanted, I knew it from her movements, and I continued, controlling the pace, on this occasion I was in charge. When the moment came, I ran my tongue deftly across her swollen, expectant clitoris and brought out the most audible moan of pleasure I’d heard from her.

I moved briefly away from her most sensitive part and teased the area closest to it before returning with the tip of my tongue to urge stronger waves of pleasure. As her climax approached, I used the flat of my tongue right across her clitoris to give maximum stimulation, concentrating on bringing her to an ecstatic conclusion. She writhed her body, arching her back pushing herself against my tongue and moaning with pleasure as her orgasm flooded her body. I could almost feel the waves of ecstasy pulsating through her as she rode the storm of pleasure.

Her hands gripped my head, holding my face against her pussy ensuring her pleasure lasted for as long as she could take it. Then, when I felt her relax, she gently pulled me upwards to lay on top of her.

“I didn’t deserve that pleasure from you, Michael, after how I’ve behaved. To take that punishment for me, to save my job, I realise how much you care for me, and I now realise how much I care for you.”

Her legs parted for me and I slipped my throbbing penis inside her, feeling the incredible sensation of her moist sex. The ecstatic feelings my penis experienced as I slowly thrust inside her drove me almost insane with lust. All thoughts of pain in my bottom were a million miles away. This was all about pleasure, and as I quickened my pace, Jenny tightened herself around my stiffness to increase the pleasure we were both feeling.

My orgasm was so close, the pleasure reaching a peak. Jenny was moaning again and thrusting in perfect unison with me as we wrapped ourselves closely together. This was the moment I’d waited for throughout the years I’d known Jenny, and then it arrived in an explosion of pleasurable joy and ecstasy. She moaned loudly and I moaned louder as I thrust into her, pumping my ejaculation deep inside her. Thrust after thrust sending spasms of pleasure through my body as my orgasm peaked.

And as the ecstatic sensations slowly eased away and our bodies relaxed, we remained wrapped in each other’s arms, each supporting the other as we returned to our normal levels of consciousness. Eventually, we broke apart, lying on our backs next to each other, holding hands, not wanting to let go.

After many minutes of silence, it was Jenny who spoke first, breaking the tranquillity of the moment. “I think I need to cane you more often,” she whispered.

After a moment to allow it to sink in, the two of us burst into laughter. Was it a joke or was she being serious? I had certainly taken the extreme route to finally get the girl I wanted.