Jenny

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.