“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.