I Got Caned for Cash

I answered an Australian Doublelist ad for a guy required for a BDSM fetish. Its not my usual thing but for some reason on this day it caught my curiosity.

I sent him off a message saying I was curious and after a few emails and he offered me a decent reward to allow him to cane me. Although I didn't really need the money, I felt an underlying want for the experience that I could remember feeling after experiences at my primary school, which in those days used corporal punishment as a first resort.

I was only ever caned once at school on the hand. It wasn't a hard hit and I was lined up with a whole group of other boys just getting one on the hand for misbehaving. I had seen other students get up to six strokes and often wondered what that sort of caning felt like.

The only other time I received corporal punishment was when I back chatted a teacher and she put me over her knee after school. I always thought I was a reasonably good student but when a good friend of my mothers was a fill in teacher I crossed the boundary of student teacher protocol and was forced to stay back after class.

Alone in the classroom with her, she took the time to scold me about my attitude and built up the atmosphere for the punishment I was about to receive. She was holding the cane as she dressed me down verbally and was threatening its use continually. She was looking for tears from me and when she finally got them she softened her persona and adopted a more caring approach.

After placing the cane on the table, she sat on the chair and beckoned me over to her. She reached out and took my hands and held them and told me she didn't want to hit me but I needed to be punished and ordered me to lower my pants.

Now this request would never fly these days, but in those days it was common to see a girl have her skirt lifted and boys have their pants lowered in front of the whole class while they were spanked.

This time I was lucky enough to not be paraded in front of a class of laughing children, so I took down my shorts and underpants and stood next to her while she led me over her knee.

She started her sermon again on behaviour while she lent her hand on my bottom. Her voice would be calm and then she would work herself up as she spoke and as she got to the peak of her tone she would smack me on the bottom. After each smack she would start talking again as she lightly rubbed my buttocks. The soothing feeling of her hand was counter productive to the smack and as an eleven year old its my first memory of having a sexual feeling.

She would have felt my excitement against her thigh and I didn't quite know what was happening to me until she stood me up and could see my arousal. I stood there for a moment and there is no way she could ignore it, but she did and ordered me to pull up my pants and go home.

After that event, whenever I saw another student put over the knee of a teacher, without fail I would get and erection.

Fast forward to the present, and here I am walking past the entry to what appears to be a doctor's surgery on the main road of Riverwood in Sydney's west.

I arrived early to our meeting place. He said the premises were shared and he didn't want anyone around to hear the noise. It was a cold morning and at five am was still dark. I was kidding my self that I was ok, but I was sweating and could feel my heart beating out of my chest. My phone lit up and I looked at the screen. He just sent me text to see if I was on time. I looked at his previous text which was the address, I checked I was in the right place and responded "I'm here".

The light went on behind a glass door that was frosted so I couldn't see in from the street. Then a silhouette appeared behind the door. I moved over to the door as I heard it being unlocked. It opened and I was greeted by a tall guy that I estimated to be at least sixty years old. He pointed to the centre of the room and just said "stand there". He locked the door behind me.

There was a large reception desk In front of me, chairs surrounding the perimeter of the room and just to the left of the reception desk was a large twisting staircase going up to the next level. I noticed a large amount of security cameras scattered around the waiting room.

The man returned with a yellow plastic washing basket and dropped it on the floor in-front of me. He said his name was Bob and I was to refer to him as "Sir". He also stated he wasn't interested in chat, speaking or even hearing my voice. He produced an A4 piece of paper and read it out to me. It was fairly clear and stated that I consented to him tying me up and caning, spanking and whipping me. It also said he would stop the session if my skin broke or he felt it was not safe to continue. Once he had finished, I nodded in agreement and took the contract over to the reception desk. I reviewed the document again and stopped short of the signature at a tick box. It had an option to remove any safe words and I paused over it for a second, ticked the option and signed my life away.

Bob took the contract and placed it in the photocopier next to the reception desk, and then placed my copy of the contract into the basket on the middle of floor. He then demanded I remove my clothes and place them in the basket.

It was freezing cold in the building. I took my shoes and socks off and the chill of the tiles actually stung the soles of my feet. Then I removed my jumper and shirt and dropped it into basket as well. It felt strange being half naked in what would normally be a public space and I wondered what the footage from all of the cameras would look like if someone reviewed it later. Finally, I removed my jeans and underwear and stood naked In front of him for inspection.

He motioned for me to follow him and he led me to a consulting room on the same floor as the reception and told me to lay on my side with my back towards him. There was a bag that I thought was a drip at first sight, but he explained it was for colonic irrigation and told me he didn't want me to shit all over his surgery floor. I felt his cold hands on my butt, then he spread my cheeks to get access to insert the tube that delivered a warm solution into my rectal cavity. Once the fluid had drained from the bag, he escorted me back to the reception.

I could feel the water in my stomach and a mild need to evacuate it. He motioned me upstairs but when I tried to go up the need to let the solution in my rectum go was too strong. I held onto the banister while I waited for a cramp to subside, then once it faded, I would attempt to get up another few stairs before the cramp would kick in again. It took a couple of cycles but I made it to the top without spilling a drop and was relieved to be shown the upstairs bathroom where I quickly sat down on the toilet and cleaned out my system.

When I came out of the bathroom, he was waiting for me outside one of the rooms. The door was open and he signalled that I needed to enter. The room was a storeroom and in the middle of it was what looked like a modified massage table. It appeared it would allow him to bend me over and have my face sit in a hole and there were various other holes in it as well. In the room was a basket of ropes and there were some paddles and canes and a few belts on a table to the side of the room.

He took out a really long rope and told me to face the wall. He started wrapping it around my arm near the elbows and twisting it around and working the rope down towards my wrists. Every few loops he would tie a knot which would pull, my arms closer together, enough that I could feel the tension in my shoulders. Once finished, he took me to a mirror to show off his handy work. I noticed the ropes were perfectly aligned and each knot was neat and aligned as the ran down my arms. I also noticed that I had zero movement. This was contrary to my imagination of handcuffs or loose bindings and I felt strong wave of claustrophobia sweep over me. Bob could sense my discomfort and assured me it would be all over shortly if I just did what I was told. He took me through a breathing exercise which helped a lot and started telling me the origins of the sort of binding I was in, which in this case did the job as I felt comfortable again.

I had put my head against the wall again. He restrained my ankles with two straps attached to a pole which kept my ankles about a foot and a half apart. He then took another long piece of rope and after massaging my tentacles to get them out of the warmth of my body, proceeded to wrap the rope around them. He did it slowly, wrapping the rope around once, then letting my body concede, then wrapping it around again. I could feel constriction but it wasn't painful. He finished off by tying the rope off to the centre of the leg restraint pole.

Finally, he put a restraint over my head with a large ball that went in my mouth and then he put a large dogs choker chain around my neck and then led me to the table.

He had to assist me to the table. Turning around with my balls tethered to my legs was difficult and one wrong move meant an injection of pain. I could only waddle and as I caught sight of myself in the mirror, I could see my hands and balls were already turning blue. As he bent me over the table, he fed the choker chain thought he hole and fixed it off underneath pinning my head to the table. My feet were secured to clips near the floor and a large belt held my waste to the table. He slid a mirror under the table in front of me and I could see my face through the hole with the big red ball strapped in my mouth. I was kidding myself if I didn't think I was scared. I could see the mirror shaking with every beat of my heart.

Bob was hovering around me. Every now and then he would run his finger across my body and I would jump. He smacked me on the bottom with his hand a couple of times and then headed over to the table where I could hear him picking up some of the utensils shuffling them on the table.

I could feel my balls getting warm from the restriction. I could also feel my heartbeat in them. Bob held a wooden spoon under the table for me to view and then went around and gently rubbed and patted my buttocks. As I flashed back to my childhood and some of the spankings I would get from my mother. He hit me twice, once on each buttock. There was really no pain. Just a warmth from where I had been struck.

The second round was two quick hits in the same spot on each side. The hits didn't feel harder, but the second hit had a much greater intensity. Bob repeated the same process with three strikes and it was then I knew I was earning my money.

I could only take the fourth round before I started to call "stop" through the gag ball. The hits were stinging by the second strike and the intensity after the fourth was insane. The gag ball made it worse because as I tried to gasp for air it blocked my throat and made choke. I could feel it pulsating in my mouth as I inhaled and exhaled. Subconsciously I was twisting to try and spread the coverage and take away the sting. But the tether between my balls and legs made me need to choose between the pain on my backside or stretching my balls. By the time he was finishing his tenth round my bottom has gone completely numb.

Bob went over and returned the spoon to the table. I lifted my head a little and a stream of sweat ran down my eyes and onto the floor. He held a belt under the table for me to view and then went back around behind me and adjusted the tether around my balls. I let out a huge sigh of relief as he undid the bindings then he gently massaged them to get the circulation going. Once satisfied he cupped my whole package in his hands and pulled everything to the rear and tied my knees together. He was then able to run his hands down my bottom, over my exposed penis and down the back of my thighs.

I heard the whoosh of the belt. The sting was tolerable and less focussed on one point than the spoon. It was the first time I had been belted and was a childhood fear of mine. My mother's best friend used to bring her children over to our house and without fail would use the belt on them. My mother used to be against it, but never had a problem using the wooden spoon at the drop of a hat.

His first lashes were high, and then low. Starting from around my tail bone for the first one, and then down around my knees for the second. The lashes stung, but I didn't feel the need to yell like with the wooden spoon. He worked his way to the centre stopping just short of my exposed cock but close enough that I could feel the wind from the belt. With my bottom still numb, the main pain was on the back of my thighs and he focussed several lashes right below my cock that made me move around.

Bob took a pause to adjust the strap going over my waste and make sure I couldn't wriggle. He also checked the restraint around my knees. Squeezing his hand between my legs he made sure that my penis and balls were sticking out as far as possible towards the rear as he applied another rope around my thighs to keep my penis in place.

Ironically, I was thinking I was glad he placed the rope around the section of my thighs that actually hurt the most. He started with the belt again, beginning high around my tailbone and working his way down my buttocks. I could feel the lashes were heavier and he was dwelling on the same area for a couple of hits which was really starting to sting. He told me to stand on me tippy toes and he concentrated a few hits to the soft underside of my butt cheeks, glancing the shaft of my penis and making me jump.

There was a break in the belting session and I heard the door open. I couldn't see the door from my position and I had to control the anxiety of thinking I could be left tied up while Bob just left. I would assume it would be a bad sight for the person that found me. Fortunately, Bob came back and even better he had a towel and much needed water. I held my head up so he could wipe the sweat from my forehead, and he reached under the table with a glass and a straw so I could have a break as well. He wiped down my back and my butt and told me there was one more round of the belt to go.

He started off hard and I could tell he couldn't really place the belt where he wanted to. He was trying to get me on the bottom of the cheeks and a few wayward lashes caught my testicles and before I could even react, he caught two more direct hits before throwing the belt down.

I thought I was going to be sick. The pain in my testicles was unbearable. I was trying to breath it out, but the gag in my mouth wouldn't give me enough volume. Bob knew he hurt me; he held his hand on my back but this was no relief. He went and got a cloth with cool water and cupped my balls in it to try and relieve the pain. He removed the belt holding my knees together and allowed my balls to freely hang, cradling them for a few moments before grabbing the cane.

I heard the swoosh of the cane as he made a few practice strikes in the air. I was surprised at how loud it was. Then Bob slowly ran the cane down the small of my back, over my bottom, testicles and then down my leg. He continued this a few times and then came around and removed my gag and then the choker so I could lift me head.

I went to say something, and he slapped me in the face. I had to hold back the anger; I could feel my temper raising. He could see it in my eyes and slapped me again right across the cheek. Now I could watch him walk around the room, and he walked over to his stash of canes and started selecting them one by one. They were different lengths and thicknesses, and they would each make a different noise has he cut them through the air.

He brought them over to me and told me to select one. I immediately dismissed the two longer ones. And settled on the one with the middle thickness, which was about three quarters of an inch round and about three feet in length. It was smooth and had a slight bend in it and made a very distinctive whoosh as he whipped it around.

He told me to open my hands and spread my fingers. He tapped my palm with the cane a few times and then the whoosh signalled my first strike. I heard the crack and then felt the pain. He used the cane to tap the knuckles of my tightly closed fist until I opened my hands again, then he let go with another crack. This one was the worst, he hit right on my thumb. There was minimum meat there and I felt the tingle as it hit the bone. I yelled and swore and tried to turn around to face him, but he came up to me and slapped me again. I was starting to struggle now, as I felt my anger starting to ignite. He grabbed the choker chain and placed it around my neck and pulled my face down to the table again and secured it. I thought I could taste some blood in my mouth and spat down on the mirror to check for traces in my saliva.

He dished up the first set of six. Each "whoosh" signalled the incoming strike, and the following crack signalled the incoming sting. I counted out the six but then there was a seventh and an eighth. I had reached my limit and was yelling for him to stop, but the strikes kept coming.

He paused for a moment to inspect his handy work. As he ran his hand over my bottom, he commented on how good the welts were. He took the time to point with his finger at the sections of my bottom that hadn't seen the wrath of the stick and told me it would be over as soon as these clean pieces of flesh were nicely coloured.

He started the caning again. Lightly tapping the targeted area before taking a hard swing. It would take him several goes to hit his mark and the wayward strokes made me yell as they impacted an already tender section of my butt. Finally, there was an odd noise from the cane and I heard something hitting the wall to the side of me. He cane had broken, and I could lift my head up just enough to see him walk over to pick up the broken piece.

Bob rechecked the tension on the choker and adjusted it. I could lift my head high enough from the table to be able to turn it. He sat on a swivel chair and then slid it under the table where his crotch was level with my face. He checked his height on the chair and then slid out from under the table, pulled out his cock and then rolled the chair back in.

He had a reasonably well sized cock. He wasn't circumcised, and even rock hard, he still had a good coverage of foreskin so I couldn't see the tip of his cock. He raised his chair and at first, he pushed his cock into my eye, but I lifted my head giving him the opportunity to find my mouth. He then sat there still while he guided my head up and down and moaned.

It was the first time I had an uncircumcised penis in my mouth. I've always thought of them as unclean and preferred cut penises. He was taking it gently and I was using my tongue to tickle down the end of his knob through the foreskin. I could tell he liked it, because he would deliberately hold my head in place for a few seconds before lowering me back down over his shaft.

I like to give head when I have control. I'm normally on my knees because I like to use my tongue on the sensitive underside of the head. I also like to use my hands. I couldn't use any of my trademark moves to hasten his ejaculation because all I could do was keep my mouth open and let him pleasure himself.

He reached under the table and pulled back his foreskin. The head of his penis spread out and was like a mushroom. I could see the precum leaking out the tip and I reached out with my tongue and tickled the tip, and then put my lips right on his hole and lightly sucked the precum as it was produced.

Bob was moaning with pleasure; I kept my lips just on the tip of cock while he reached under and started rubbing his shaft. He was moaning even loader and slowly pumping away. He was twisting the end of his knob and once he stopped, he let out a huge breath and then I felt the pulsating of his cock and the warmth in my throat as he blew everything he had into mouth. I started the light sucking motion again to make sure nothing was spilt, and when he carefully removed his cock from my mouth, I had managed to take everything he gave me.