Phil Hooper
06-09-2012, 12:42 PM
My heart quickened slightly as the tyres crunched gently across the large gravelled drive at the front of the impressive looking house deep in the Leicestershire countryside. I had known Simon for almost twenty years now. It seemed a long time since I had first answered that advert in the Daily Sport inviting readers to visit a "strict headmistress" in rural Leicestershire. I had always had a fascination with canes which began at my all boys grammar school. My interest in bottoms had developed after my 14 year old friend at school John told me out of the blue one day that I had the best shaped and nicest bottom in the school. I had been looking at it only a couple of hours previously in the mirror at home and John was still right. On the larger side of medium, smooth, hairless, firm, round and with very pert cheeks and a deep, inviting dark cleft. I could still just make out the faded marks from Simon's last caning. John had got to know that bottom very well so he should know.
Miss Beryl Chambers had caned me on quite a few occasions and I liked her a lot. We had talked freely about my interest in all things anal and one day she suggested that I may like to visit the owner of the house Simon as he shared those same interests. I asked if he was gay? "No" she replied "but he is very adventurous. You'll like him I'm sure."
On my next visit to Beryl we arranged that Simon would cane me with her present. Simon was dressed as a headmaster complete with mortar board and black flowing gown. He was in his mid forties a similar age to myself at the time and a successful businessman. Like me I discovered later that he had had many ladies in his life. The caning was hard and accurate and the post caning therapy confirmed that he was both adventurous and experienced. I had been visiting him every month or so ever since.
I walked from the car to the rear of the wooden two storey garage workshop block to the left and knocked on the door marked Office. After a few seconds I heard Simon on the stairs. The key turned and the door opened. "Come in my boy. Nice day. Good drive over?" "Yes thanks Simon" I replied as I walked past him up the stairs as he locked the door behind me.
The study was light and airy and contained a large array of canes, paddles and school related pictures on the wall. Aside from the equipment it passed well for a real headmasters study. Large bookcase, leather topped desk, several chairs, I sat down in the usual comfy one. On the desk were three canes which Simon had pre selected for today and the familiar little brown bottle next to the medical mask and a new clean white make up removal pad. This was a much practised routine. I felt at home here and very much at ease with Simon. This was a place of safety where the years seemed to roll away.
Simon sat down behind the desk. We talked the usual stuff about business, sport and politics for ten minutes or so. Then there was a lull in the conversation. My heart quickened slightly. "Right, lets have the school fees and then go down to the bathroom and get undressed for me please." I counted out the notes and went to the bathroom as instructed. It was as spotless as ever with a neat pile of towels on the chair at the far end.
I undressed slowly watching myself in the mirror. My cock was hot and hard. I admired my bottom from every angle excited that Simon would also soon be admiring it again. With my heart beating faster I headed back to the study and knocked on the door. "Come in Green." I entered with my cock protruding powerfully ahead. "I am going to cane you hard, 36 strokes and then I will give you some much needed pleasure." My nipples were as hard as my cock and I could not resist playing with them as I looked at my bottom again in the big mirror set up behind the leather caning bench which I would soon be instructed to bend over. Simon was now dressed in that familiar black flowing headmasters gown. He had picked up the little bottle and was charging the cotton wool pad which he then placed behind the elastic on the inside of the mask and handed it to me. "Take your time" he said.
I took the mask and positioned myself behind the caning bench. I could see my bottom clearly in the mirror facing me reflected back from the mirror behind positioned so that it did not obstruct the arc of the cane. Simon had picked up one of the canes and was watching me closely. My cock was still proudly erect. "Take your time" he repeated gently.
I put the mask to my face and breathed in deeply. The fumes had a familar exciting smell. Slowly I felt their heady effect building more and deeper. I needed that pain. My bottom looked fantastic. I felt my sphincter relax as the poppers took more effect. "Take your time," I took another deep breath from the mask then another and another. "Bend over Green." The voice was deep and authoritative. "Yes Sir" I replied.
I bent over and watched my bottom cheeks part slightly. That deep dark cleft grew wider. I could just make out my anus, eager and inviting. The effect of the poppers was still building and gloriously hazy and heady.
I could see Simon in the mirror moving into position behind me and to my left, black silk gown flowing out widely as he stretched out his right arm, the long thin cane in hand, right shirt sleeve carefully rolled up to the elbow. I could see the cane touching my bottom. It felt cold. Simon continued to adjust his position a bit like a golfer, bending forward at full stretch now. He had stopped moving now and was perfectly still.This was it.
I watched the cane arc back high over Simon's right shoulder. There was a brief pause. Then I heard it. CRACK. A millisecond pause. Then it came. Pain, pure white hot pain, spreading out from the thin line I could see developing across both cheeks of my bottom. CRACK. The second stroke landed before the pain from the first one had finished building. YES I cried completely involuntarily as the waves of pure powerful cleansing pain continued to build. Four more, CRACK, CRACK, CRACK, CRACK. Four more delicious lines of pain.
Simon stood back, put down the cane on the desk and admired his work. His big strong right hand touched my bottom, rubbing gently, middle fingers teasing gently between my cheeks. Than back to work for the second six strokes. CRACK, CRACK, CRACK, CRACK, CRACK, CRACK. The intervals between the strokes were about four or five seconds. Simon was breathing more heavily now. This was a real caning. They always were. This was not play.
Another 30 seconds pause to rub my by now very bruised bottom. Then CRACK, CRACK, CRACK, CRACK, CRACK, CRACK again.
"18 strokes completed, 18 more to go" Simon was breathing even more heavily from his exertions.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
"Do you want any more?"
"Six more please Sir. As hard as you can and fast"
Simon duly obliged.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
That was it. I had been caned. The relief was as it always was. Indescribable. I had endured it. I had taken the hardest caning this fit, intelligent and successful man in the upper regions of middle age could give. Simon pulled a tissue from the box on the desk and dabbed the slightly damaged skin on my bottom.
"Go to the bathroom and clean yourself up. Take your time. I'll see you in a few minutes."
Miss Beryl Chambers had caned me on quite a few occasions and I liked her a lot. We had talked freely about my interest in all things anal and one day she suggested that I may like to visit the owner of the house Simon as he shared those same interests. I asked if he was gay? "No" she replied "but he is very adventurous. You'll like him I'm sure."
On my next visit to Beryl we arranged that Simon would cane me with her present. Simon was dressed as a headmaster complete with mortar board and black flowing gown. He was in his mid forties a similar age to myself at the time and a successful businessman. Like me I discovered later that he had had many ladies in his life. The caning was hard and accurate and the post caning therapy confirmed that he was both adventurous and experienced. I had been visiting him every month or so ever since.
I walked from the car to the rear of the wooden two storey garage workshop block to the left and knocked on the door marked Office. After a few seconds I heard Simon on the stairs. The key turned and the door opened. "Come in my boy. Nice day. Good drive over?" "Yes thanks Simon" I replied as I walked past him up the stairs as he locked the door behind me.
The study was light and airy and contained a large array of canes, paddles and school related pictures on the wall. Aside from the equipment it passed well for a real headmasters study. Large bookcase, leather topped desk, several chairs, I sat down in the usual comfy one. On the desk were three canes which Simon had pre selected for today and the familiar little brown bottle next to the medical mask and a new clean white make up removal pad. This was a much practised routine. I felt at home here and very much at ease with Simon. This was a place of safety where the years seemed to roll away.
Simon sat down behind the desk. We talked the usual stuff about business, sport and politics for ten minutes or so. Then there was a lull in the conversation. My heart quickened slightly. "Right, lets have the school fees and then go down to the bathroom and get undressed for me please." I counted out the notes and went to the bathroom as instructed. It was as spotless as ever with a neat pile of towels on the chair at the far end.
I undressed slowly watching myself in the mirror. My cock was hot and hard. I admired my bottom from every angle excited that Simon would also soon be admiring it again. With my heart beating faster I headed back to the study and knocked on the door. "Come in Green." I entered with my cock protruding powerfully ahead. "I am going to cane you hard, 36 strokes and then I will give you some much needed pleasure." My nipples were as hard as my cock and I could not resist playing with them as I looked at my bottom again in the big mirror set up behind the leather caning bench which I would soon be instructed to bend over. Simon was now dressed in that familiar black flowing headmasters gown. He had picked up the little bottle and was charging the cotton wool pad which he then placed behind the elastic on the inside of the mask and handed it to me. "Take your time" he said.
I took the mask and positioned myself behind the caning bench. I could see my bottom clearly in the mirror facing me reflected back from the mirror behind positioned so that it did not obstruct the arc of the cane. Simon had picked up one of the canes and was watching me closely. My cock was still proudly erect. "Take your time" he repeated gently.
I put the mask to my face and breathed in deeply. The fumes had a familar exciting smell. Slowly I felt their heady effect building more and deeper. I needed that pain. My bottom looked fantastic. I felt my sphincter relax as the poppers took more effect. "Take your time," I took another deep breath from the mask then another and another. "Bend over Green." The voice was deep and authoritative. "Yes Sir" I replied.
I bent over and watched my bottom cheeks part slightly. That deep dark cleft grew wider. I could just make out my anus, eager and inviting. The effect of the poppers was still building and gloriously hazy and heady.
I could see Simon in the mirror moving into position behind me and to my left, black silk gown flowing out widely as he stretched out his right arm, the long thin cane in hand, right shirt sleeve carefully rolled up to the elbow. I could see the cane touching my bottom. It felt cold. Simon continued to adjust his position a bit like a golfer, bending forward at full stretch now. He had stopped moving now and was perfectly still.This was it.
I watched the cane arc back high over Simon's right shoulder. There was a brief pause. Then I heard it. CRACK. A millisecond pause. Then it came. Pain, pure white hot pain, spreading out from the thin line I could see developing across both cheeks of my bottom. CRACK. The second stroke landed before the pain from the first one had finished building. YES I cried completely involuntarily as the waves of pure powerful cleansing pain continued to build. Four more, CRACK, CRACK, CRACK, CRACK. Four more delicious lines of pain.
Simon stood back, put down the cane on the desk and admired his work. His big strong right hand touched my bottom, rubbing gently, middle fingers teasing gently between my cheeks. Than back to work for the second six strokes. CRACK, CRACK, CRACK, CRACK, CRACK, CRACK. The intervals between the strokes were about four or five seconds. Simon was breathing more heavily now. This was a real caning. They always were. This was not play.
Another 30 seconds pause to rub my by now very bruised bottom. Then CRACK, CRACK, CRACK, CRACK, CRACK, CRACK again.
"18 strokes completed, 18 more to go" Simon was breathing even more heavily from his exertions.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
"Do you want any more?"
"Six more please Sir. As hard as you can and fast"
Simon duly obliged.
CRACK, CRACK, CRACK, CRACK, CRACK, CRACK.
That was it. I had been caned. The relief was as it always was. Indescribable. I had endured it. I had taken the hardest caning this fit, intelligent and successful man in the upper regions of middle age could give. Simon pulled a tissue from the box on the desk and dabbed the slightly damaged skin on my bottom.
"Go to the bathroom and clean yourself up. Take your time. I'll see you in a few minutes."