On Report with Mr Jenkins

It had become routine. 

I stood naked in front of Mr Jenkins desk. A senior cane on view as Mr Jenkins busied himself, writing something. It felt like an hour I was stood there. It had only occurred to me how deliberate this was. 

My hands by my side waiting for him to finish I could feel my cock growing more erect. 

I thought of the chance and the absurdity. I was waiting for my caning and the more I thought of the cane strokes landing the more excited I became. I could feel a thread of pre cum falling on my thigh. 

I was glad Mr Jenkins had taken me as his special pupil. 

Sucking Another Boy

The situation arose as Mr Jenkins had found me with another boy in the little used toilets behind the music school. We were in the end cubical. I was on my knees with Taylor’s cock in my mouth. I’d undone my trousers and was stroking the head of my cock through the tight pink and white panties I had stolen. 

Now I was here again. It was a Tuesday report. Sometimes I would meet on other days to report and be punished but Tuesday was the main beating. 

Sexual Activity

I had written several essays for Mr Jenkins. The first confessing sexual activities including the theft and wearing of girls panties. Mr Jenkins had taken pictures of my in my panties and made it clear it would be ‘our secret’ as long as did his bidding. I’d written further essays about my fantasies and I knew he would enjoy their contents. 

Winchester Postion Variation

Mr Jenkins cleared his throat and instructed me to stand up straight. He went back to writing for a minute or two and then put his pen down. His eyes fixed on my groin. I thought he smiled slightly at the site. Part of my obedience was to have a fully shaved cock, balls and pubis. I enjoyed it. The smoothness was erotic and a delight to feel myself. I know Mr Jenkins enjoyed my state too. He enjoyed it so much he would punish me if I showed a few hairs. 

He looked at the chairs up against the wall of his study and I knew it was time. 

Mr Jenkins enjoyed punishing me in various positions and he’s even invented one for his pleasure. This was a variation of the ‘Winchester Position’. In this variation the naked boy knelt, one knee on a sperate chair and bent over the third. Thus his legs were spread wider, the cock and balls in view and accessible. 

I got into position and the caning commenced. To say Mr Jenkins was an artist with the cane would not do his ability justice. 

He didn’t give the number of strokes but would lay them on in sets of six. I suppose this was dependent on his sexual feelings. He also liked to take his time over each set. Sometimes I was ordered into the corner between sets sometimes I had to stay in position. 

I caught a glance over my shoulder, Mr Jenkins always wore a three-piece suit, this was his grey one. He was brushing his white moustache with his fingers and looking at his reflection in the glass fronted book case. He put the cane down and cleaned his glasses. 

His Fingers

His fingers glided over the raised weals on my buttocks then descended between my thighs to stroke and then cup my dangling balls.

The second set of cane strokes were applied below the first set, the last landing just under my buttocks. 

He Pushed a Little Harder

I saw him put the cane back on his desk. I was close to tears but, as always, determined not to cry. He then started to spank the back of my thighs. This was sore and I started to gasp and wriggle. I believe this was one of his favourite parts of my session my bottom going pink, the little gasps and the wriggling all excited him. I knew because he stood close up and stroked my back as his crotch pushed into my sore bottom. I felt his male hardness and groaned slightly, he pushed a little harder.

I was bidden to stand. My erection that had been lost during the caning start to appear again. Mr Jenkins opened his study door and I exited with him a pace behind me. 

Foreskin in Mouth

We entered his bedroom. 

I knew what he wanted. I started to undress him, placing his suit on the stand. Finally I pulled off his pants. Mr Jenkins had a hairy pubis, dark hair at odds with the white hair on his head. I stood up at attention waiting for his next order. 

It was to kneel. 

I knelt and took his foreskin into my mouth. I pushed my tongue in t lick up his pre cum and then took the whole glans in my mouth and worked on is with my lips covering my teeth and kept moist with my saliva. 

He sat on this armchair and I went to work longing for him to explode in my mouth. It didn’t take as long as I expected. His hand stroking my head he started to lightly thrust. His groans becoming stronger as he shot his hot cum into my eager mouth. I usually spurted three to four times. I swallowed each. I knew he liked that. A slight stream of cum had escaped and was oozing down his shaft. I licked it up and took his glans in my mouth to make sure I had all of his juice. He shuddered. 

His eyes were closed and I could read the contentment on his face. 

I got a flannel and towel from his bathroom and cleaned him up.

Quite a session I reflected later. Most enjoyable…

If you like any part of this story and would like to recreate some of it or just fancy a chat email me willingbotboy@gmail.com 

NOTE

I nicked the main picture from spankthishookups.com Sorry!