Miss Gray

"What are you doing, Daniel?"

I froze, caught in the act, hand on the cover of the folder marked 'final exam papers'. There was no chance of talking my way out of this.

"Miss Gray, I..."

"How could you? You of all people?"

I had been Miss Gray's star pupil since the first day of school when I was barely a teenager until this moment, the final week of my final year when I had just turned eighteen and was ready to graduate to university. We were working after school on the yearbook. She had left her office to go and get some food for us and had come back unexpectedly soon.

"I'm so sorry, Miss Gray, I don't know what I was thinking! I didn't see anything!"

The exam paper was right there. I was going to ace the exam anyway, I had mostly been genuinely curious, but I was in line for the state prize I thought, and a bit of help couldn't have hurt...

Miss Gray looked angrier than I'd ever seen her, no, I take that back, angrier with me than I'd ever seen before. She was known to have a fiery temper. She was the teacher that everyone had a crush on; early thirties, long red hair, pale skin currently flushed with rage.

"Daniel, you were about to cheat! If I hadn't forgotten my handbag, you'd have been reading the exam questions right this minute! I cannot believe you'd abuse my trust like this! You will probably be expelled!"

My blood ran cold. This would ruin my life.

"Please, Miss Gray! I'm so sorry! I don't know what came over me! Please don't..."

"Be silent!"

I complied. She motioned me to sit. She pulled up a chair and sat facing me.

"Daniel, I'm sorry too. You're my favourite and brightest student, it's a tragedy, but I can't simply let this pass."

I was desperate. My mind raced.

"The Last Resort!" I blurted out.

"The Last..? Dan, that was a joke!"

The Last Resort was an old school cane hanging by the blackboard in Miss Gray's classroom. She joked on the first day that it was the last resort if the class ever got really out of line. It was used for pointing at things on the board and occasionally rapping the desk for attention. It never failed to focus our minds even though corporal punishment had been abolished for over a decade.

"Please, Miss Gray! I'm so sorry! Please don't get me expelled!"

She actually paused to consider this. I had a glimmer of hope.

"Daniel, I suppose this episode is between you and me. You clearly didn't see the paper, so no harm done, but if we did this, it would have to remain strictly between us. I will have to think about this. Please go and fetch The Last Resort and I will decide what to do."

"Thank you, Miss Gray!"

"Go, please!"

I jumped up and exited Miss Gray's office and headed down the stairs to our classroom. It was dark outside and my footsteps echoed weirdly in the quiet.

When I opened the door to Miss Gray's classroom and spotted The Last Resort hanging on its hook, I suddenly realised what was happening. I had just begged to be caned by Miss Gray.

I lifted the cane off its hook and the familiar object suddenly took on a sinister dimension. It was just under a metre long and about a centimetre thick. I struck my hand with it experimentally and yelped a bit. A gentle tap hurt! How was a full-blooded stroke from my English teacher going to feel? I was certain from the look in her eyes that if she decided to go through with this, my cherished Miss Grey, who I considered more of a friend than a teacher was not going to hold back. I had betrayed her trust and I was going to pay for it.

I started the long walk back to Miss Gray's office with the stick she was probably going to beat me with. Would she hit me on the hands or on the bum? I don't think I could go through with it on my hands, watching the cane descend. Fuck, but if it was on the bum would I be allowed to keep my pants on? My cock started to stiffen at the thought. Shit, I thought, trying to make it go down, please don't make this any more humiliating than it has to be.

By thinking grimly about what might be on the exam that had got me into this predicament I managed to get my penis under control by the time I made it to Miss Gray's door. I hesitated, then knocked, even though I had only just left ten minutes ago.

"Enter."

I tentatively opened the door. The room seemed warm and bright compared to the dim corridor. Miss Gray was standing by her desk, which she had just cleared. She held out her hand and I stepped towards her and handed over the instrument of punishment. She stared at it, fascinated for a moment, then pulled herself together and addressed me.

"Daniel, I have considered my options, and I cannot simply forget this happened. I also feel it would be a terrible shame for you to ruin a bright future with expulsion, so I am willing to cane you if you accept my terms."

I felt my face flush and my heart pound. The room did feel slightly too warm. Miss Gray tapping the cane on her palm wasn't helping.

"This must remain entirely between us. Once it is done, the matter will be over and we will never speak of it again. I am going to give you six hard strokes on your naked backside."

I gasped. Oh shit, my erection started to return.

"There is no debate on this. I cannot cane your hands as the marks will be obvious. Also, I have never caned anyone before, and I do not trust myself to avoid damaging you, which is not the point of the exercise."

The point is merely excruciating pain, how kind, I thought

"Your bottom will be welted and bruised by the end of this I am certain, but you are smart enough to be able to hide that until you have healed. Due to my inexperience, I am not confident in caning you unless I can see the naked target. Also, your abuse of my trust was humiliating to me, and I wish you to be humiliated as well. Do you understand this?"

I did, though all my penis seemed to understand was I was about to be naked in front of a teacher I had masturbated to more than once. My hands covering the bulge in my crotch, but fooling nobody, I nodded.

"Please say you understand."

"I understand, Miss Gray."

"Your punishment will be six hard strokes bent over my desk. They will be extremely painful. If you get up, there will be extras. If this is acceptable to you, then remove your clothes and we'll get started. Otherwise, I can simply take this to the principal tomorrow."

"Thank you, Miss Gray, I will take the punishment. I am sorry, I..."

I nodded to my obvious erection. She actually smiled and said in a kind voice for the first time since I had been caught, "Oh, Dan, that's the least of your troubles. I'm truly sorry we have to do this, but you need to learn the importance of academic integrity. Now get your clothes off and let's get you caned."

I was so relieved just to have her call me Dan again, that for reasons that weren't entirely clear I asked "Everything off?"

She seemed surprised for a moment, and even flushed a bit herself, then recovered and said "Yes, actually, that might be better."

It was actually a relief to unbutton my shirt under her penetrating gaze rather than drop my trousers straight away. Sadly my erection was definitely there to stay.

"Don't drag this out, Dan."

I pulled off my shirt, looked beseechingly at her. She stared back. I blushed even harder, stomach a butterfly house, and unzipped my trousers. My erection sprang free in my underwear as my pants pooled around my ankles. My hands held the waistband and I felt a moment of wild freedom as I bit the bullet and whisked them down.

[ADVERT]

"Hands on your head."

I had an insight into how women feel about men staring at their breasts. Miss Gray's eyes were definitely on my erection, which was pointing straight up. Her eyebrows raised for a moment before she suddenly realised herself.

"Okay, over the desk and hold the far side."

"Let's get you caned," she said like it was a simple thing that didn't involve a great deal of pain and days of recovery. I bent over and gripped to the far side of the desk. I shuffled back a bit so my rigid cock wasn't pressed against the edge. How long would it take? Maybe ten seconds each, so a minute? In one minute, it would be over, but my poor bottom would be bruised and welted. Would it break the skin?

Her breathing quicker than usual, Miss Gray took a stance to my left. I felt the cane gently rest on my backside. She tapped it a few times.

I felt it draw back and flinched as it whipped through the air. There was no strike.

"Oh god, I'm so sorry, Dan, I was just practicing. I'll warn you before I'm about to start."

I actually giggled then she giggled too. She looked magnificent wielding the cane, dark knee-length skirt hugging her shapely hips, white silk shirt usually buttoned to the neck, now unbuttoned and showing a tantalising hint of cleavage. Her chest and face were flushed.

The moment of connection passed. "Face forwards, please, Dan, it's time."

The cane ripped through the air a couple more times and I stopped giggling as I realised that she intended to go through with this and was not swinging at all gently.

I was about to be hurt by my trusted mentor just because of a moment of weakness. My poor bottom would be bruised and sore for days.

"Please, Miss Gray, not too hard."

I felt her cool hand on my back, gently rubbing, soothing me.

"Dan, this is going to be hard. It is going to hurt. You deserve this. Please try and hold still and we can get this over with."

I tried to relax. Her hand stopped rubbing. The cane tapped gently on my unprotected bottom. It drew back and with a THWACK struck me shockingly hard.

I screamed and jumped up, hands gripping my agonised cheeks. I had thought I was prepared but the violence of it had taken me by surprise. I turned to her beseechingly. She looked horrified but then schooled her expression.

"Please, Dan, let's just get this done. The alternative is expulsion."

Actually, I could threaten to tell what had just happened, I thought, but dismissed the idea. She was doing me a favour here and I couldn't break her trust again. I think she realised my thought as she looked relieved as I turned again and bent, offering myself up for more agony.

Tap tap tap.

THWACK!

I yelped and jumped up again. It simply hurt so much.

She put down the cane and enfolded me in her arms.

"Does it have to be so hard?"

"I'm so sorry but yes, Dan."

Her fingers traced the two welts on my bottom. I flinched.

"Oh my god, that must hurt so much. Please be brave for me and we'll get it done."

Her perfume overwhelmed me. The pain, her breasts beneath her shirt against my naked skin, and her bizarre empathy while determined to continue beating me made me slightly dizzy. I pressed my face into her cardigan, breathed in her scent. My cock started to harden again against her skirt.

I bent again, my bottom burning, but the heat seemed to be transferring to my erection.

CRACK! It hurt so much but at the same time, I felt a surge of desire. I stayed down and groaned.

THWACK!

"Oh! God!"

THWACK!

It was like I was taking a hot bath of pain. It hurt so badly but felt so good.

"Stay still, please."

I realised I was gently rubbing my cock on the desk. I stilled myself, mortified. Maybe this broke the spell because the last stroke made me shout again and I jumped up and gripped my poor abused buttocks for dear life.

Miss Gray was staring at me slightly dazed. She opened her arms and hugged me again. Her fingers gently traced my raised welts and I flinched against her, my erection pressing against her hip.

"You took those last few quite well, you poor poor boy. I'll attend to your poor bottom in a moment after we deal with your extras."

I gasped.

"You jumped up three times Dan, however, I'll just give you two more. The last one you probably thought it was all over."

"Oh please, Miss..."

"Dan, I was very clear. Please try and take your punishment like a man. Stay still and I'll do them quickly and it will be all over."

She turned me and her hand on my back encouraged me to assume the awful position again.

"Hold tight."

THWACK! THWACK!

I gave a high-pitched squeal and jumped up again, the pain of two strokes in succession completely unmanning me. I hopped from foot to foot, my erection bouncing obscenely, in too much agony to care.

Miss Gray allowed me some dignity now, rummaging through her bag and producing a bottle of aloe cream.

"Ah, there it is. Bend over the desk and I'll rub some of this on. It will soothe the pain."

As if pain hadn't been the whole idea, I thought. She must have read my expression as she smiled gently and pushed me down again.

"Your punishment is over, Dan. I'm sorry I had to do that but you brought it on yourself."

Her fingers gently traced the marks she'd put on me.

"This must have truly hurt."

I didn't think that required a response. She squirted some cream on my backside and with a gentleness that couldn't contrast more with her previous actions, rubbed it over my skin.

The pain suffused into a heat in my backside and all through to my groin. I groaned involuntarily with pleasure as her jeans reached around and started stroking my erection.

"It's okay, Dan," she whispered, as she squeezed and stroked me to heaven and I gasped as I came hard onto the dark wood of her desk.

As I recovered myself, I sheepishly rubbed my bottom as Miss Gray wiped off her desk with a paper towel.

"You can get dressed now, Dan."

I struggled into my clothes, very gingerly pulling my pants over my bottom.

She smiled.

"You poor thing!"

Like it had been an accident that she'd just thrashed me. Then wanked me off. I was still dazed from the roller coaster of the past... could it only be twenty minutes?

"What just happened is between us only, Dan."

I nodded.

"Please make sure nobody sees that." She nodded towards my bruised ass. "And do well in your exams. Make me proud."

She hugged me again and gently pressed her hand on my buttocks.

"I can feel the heat coming off them!"

"So can I!" I responded ruefully and she laughed, then kissed me on the lips, taking my breath away. Her lips and tongue were hot and wet and I wondered dazedly what was going to happen next when she pushed me towards the door.

"That's the end of it. Go home. Please never speak of this."

I was dismissed. I opened the door and left.

I walked home in the dark, my burning buttocks the only reminder it wasn't all a dream.