I was 17 and had attended an all boys grammar school on the south coast of Devon since the age of 11. For the last two years I had been having private piano lessons from one of the masters at the school, Mr Jacobs at his private house every Saturday morning. Mr Jacobs was in his early 40s and his wife used to make us tea when I arrived. I was extremely fit, athletic and sporty at that age. Mr Jacobs used to take us for Geography and Rugby.
Some years ago a slightly older boy at the school named John had introduced me to anal sex by fingering my bum when I was a 3rd year aged around 14. John said I had the nicest bum in the whole of our school year group. We all used to shower in the changing rooms after rugby, cross country and PE and various sports and games masters including Mr Jacobs would supervise the changing rooms to stop us messing about too much. My bum was slightly larger than average, smooth, firm and naturally hairless with pert round cheeks and a deep dark cleft which as I grew older had just a slight trace of wispy dark anal hair visible. John said he often saw other boys in the changing rooms looking at my bum which made him slightly jealous but also pleased.
John and I had met regularly ever since my eager anal introduction and after a year or so of all sorts of experimentation I had finally submitted to letting him fuck my schoolboy hole liberally lubricated with Savlon antiseptic cream one Friday after school at his parents house after they had gone away for the weekend. I remember cycling home with a slippery and slightly sore arse and a wet patch in my pants where his spunk had leaked out.
Sexually John was the dominant partner and I was the submissive one although in real life I was the more sports orientated and physically more powerful of the two of us. We would meet roughly twice a month for naughty sex which would generally conclude with me bending over a chair or kneeling on the floor or bed and his cock spunking deep into my arse. Anyway, back to the piano lessons.
A few weeks previously Mr Jacobs had started to call me by my christian name Paul whereas previously he had always used my surname. He also invited me to call him by his christian name Nigel. It felt slightly awkward and contrived but I did as he asked. The following week he suggested we start to practice a piano duet with a view to playing it in the school concert later in the year. This meant that we had to sit close to each other on two piano stools. The duet was actually coming on quite well and was enjoyable and fun.
One day after a few weeks practicing it each Saturday and right at the end of the lesson as we were just finishing the piece he let his right hand just briefly fall high up onto the inside of my left thigh brushing my cock and balls. I knew that it had to be deliberate but did not say anything or react in any way. He could not possibly know anything about me and John. I wondered if maybe he had just sensed something. I was quite excited that this older married schoolmaster was apparently attracted to me.
The following Friday afternoon as we passed in the corridor a very cheery Mr Jacobs said "I'm afraid you will have to put up with my tea making skills tomorrow morning as Valerie has gone to her mothers for the weekend." My heart quickened a little with the prospect of what he might be planning.
The weather was very warm the next morning so I decided to use that as an excuse to wear some shorts which I knew were tight round my bum and which looked great in the mirror. I cycled over at the usual time. Mr Jacobs lived about 5 miles away. I was feeling quite nervous with anticipation. When I arrived he was very friendly and invited me into the kitchen while he made the tea. As we waited for the kettle to boil he looked at me and said "You look very hot today Paul. Would you like a shower to freshen yourself up?" " If your sure that's ok Sir" I replied. It's not Sir now Paul, it's Nigel. Let me show you up to the bathroom"
I followed him up the stairs and he showed me into the bathroom. "You get undressed while I get you a towel."
I took off my shoes, socks, T shirt and shorts and nervously waited for the towel wearing just my pants. I could feel my cock stirring slightly with anticipation and hoped he would not notice. I waited for a minute or so until I heard him shout from downstairs "I'll be up in a minute Paul. Just making the tea." I then took off my pants and got into the shower just as he returned with the tea and the towel. "Water warm enough for you Paul?" I said that it was and started soaping myself all over. Nigel just stood there watching me. It was slightly unnerving but I knew now for absolute certain where he hoped this was leading and I wasn't planning to disappoint him. He was watching intently as my hands were by now washing my cock and balls and I slipped a soapy finger into my anus in the interests of cleanliness and made sure he could see what I was doing by turning slightly to one side and letting him have an angled view of my bum. By the time I turned back to face him the game was well and truly up as my cock was starting to stand out proudly from my body.
"I see you are enjoying having an audience Paul" said Mr Jacobs quietly. "Yes Sir" I replied. "Come out and let me dry you off now."
As I stepped out of the shower my cock was absolutely rock hard and pointing upwards. "My my that is a magnificent specimen" said Mr Jacobs. "I had thought it might be. Turn round so that I can see your bottom properly." I did as instructed. "Bend over Paul" He knelt down behind me and started rubbing my bottom and thighs with the towel. "That arse is probably the most beautiful one I have ever seen Paul. Truly magnificent. I have long admired it since you were about 15." I felt his hands parting my cheeks and his nose sniffing my hole followed by a wet tongue probing eagerly inside. "I don't think I am the first man to do this am I Paul?" "You are the first man Sir but not the first person I gasped." "Who has been here before me Paul. Anyone I know?" I was still bending over and he was just kneeling there staring at my bum and my balls hanging down. "Another boy Sir, We have been doing anal things together for three or four years and he fucks me regularly." "I can see that your anus has been regularly used Paul. I think I must apply a few strokes of the cane to your bottom after making such a confession boy. Your arse will look even better with half a dozen welts of my cane across it. Are you up for it boy" His tone had changed as he started to play the schoolmaster again. I thought for a moment. I had had the cane at school a year earlier from the headmaster, six strokes for smoking. It had been incredibly painful but I had sort of enjoyed it. I think it must have been something to do with the fact that I had to bend over and submissively present my bottom for the headmaster's cane just as I had to present my bottom for John's eager cock. John had certainly got very excited when he saw the marks of the cane on my bottom and could not stop asking me what the caning felt like.
"Alright Sir" I distantly heard myself replying.
"Right boy. Stand up and lets get you dried off." Mr Jacobs carefully dried my entire body every nook and cranny and lingered especially long in the crack of my arse, between my legs and around my still rock hard cock and balls.
"Wait here boy while I fetch the cane and get myself ready." I waited with a very heady mix of excitement and fear. After about a minute Mr Jacobs returned with a long thin cane in his right hand. it was a light yellow colour and I would say about 3/8" in diameter. Mr Jacobs was now fully naked and his cock stood as proudly to attention as my own. I gasped at how big it was. It must have been 8 inches long at least and nearly two inches thick. He was obviously fit and athletic and his bum was smooth and boyish, nice and round and very enticing.
"Right boy. Come out here onto the landing and move that chair over there to give me a full swing with the cane." I moved the chair as instructed. "Now bend over the back of the chair and hold on tightly to the arms." I did as I was told with some trepidation but also excitement. There was no turning back now. I felt very vulnerable with my naked bum high in the air, cheeks slightly parted waiting for what I knew would be the searing pain of the first stroke. I turned my head left to watch Mr Jacobs get into position to cane me. His cock was still huge and hard as was my own. I watched as he carefully positioned himself leaning forward with the cane in his right hand, legs wide apart in an athletic stance, carefully and expertly measuring the distance and adjusting his feet for the perfect position. I turned away and closed my eyes as I felt the cane lightly tapping my bottom as he made the final adjustments to his feet. The tapping stopped. This was it. There was a long pause. Suddenly a huge noise, SWISH CRACK and then nothing. Then it came. I was expecting pain but nothing could have prepared me for the awesome searing intensity of the pain that I now felt spreading out from that line of fire in wave after wave of deep numbing pain through my quivering buttocks. I gasped loudly and uncontrollably.
"Well done boy. Stay in place. Five strokes to come." I could feel the tears welling up in my eyes. "Yes Sir" I gasped obediently.
I felt the cane gently tapping my bottom again. Again the tapping stopped. Pause...SWISH CRACK, pause, pain, terrible unbelievable pain. "Well done boy. Just four to come now."
One part of me was just crying out for Mr Jacobs to stop and the other was determined to endure what was clearly a huge sexual experience for both of us as our cocks were both still rock hard. I turned my head to watch him deliver the next stroke his cock standing proudly to attention, his face set full of concentration, lips pursed, his eyes drilling into my burning bottom. Tap,tap, pause SWISH CRACK.
Three more strokes to endure. Mr Jacobs was a powerfully built ex rugby player who was putting some serious athletic intent into the task in hand.
SWISH CRACK, SWISH CRACK, SWISH CRACCCCKKKKKKKKKK. The last stroke was the hardest but I had endured Mr Jacobs caning. "Well done boy. You may stand up." I could hardly move. The pain was still searing through my bottom in great waves. "Have a look in the mirror boy." There were six thick, deep red weals across my bottom. It was a sight never to be forgotten. My eyes were full of tears as I turned back towards Mr Jacobs who was still holding the cane. I looked down at his huge cock and sank to my knees taking as much of it's length as possible as deeply into my throat as I could. I sucked and sucked hungrily and deeply until I felt him gently pulling his cock from my mouth.
"I have other plans now Paul. Bend over the chair again please." I did as I was told and Mr Jacob's was immediately on his knees behind me again with his face, nose and tongue buried deeply and hard between the cheeks of my bottom. He sniffed, sucked and licked hungrily for what seemed an ecstatic age. "Stand up and turn round Paul." He took my cock deep into his mouth and sucked hard in and out in and out. Had I not had a wank in bed last night I would have cum in less than twenty seconds.
He then got up, headed into the bathroom and came back with a jar of Vaseline. I knew what to expect and would have been disappointed with any other outcome. "Turn round and bend over again please Paul." I dutifully and eagerly obeyed my married geography teacher and felt another surge of excitement as I felt the cold sticky ointment being spread liberally and deeply around and inside my anus. I watched over my shoulder as Mr Jacobs spread the Vaseline thickly onto the bulging purple head of his cock and down the shaft. He put the Vaseline jar down and positioned himself right behind me. I felt his cock touching me just above my balls as his hands gripped firmly either side of the top of my pelvis. "Bend your knees a little now Paul." I now felt his cock touching the entrance of my anus. "That's perfect Paul. Hold it right there for me now."
I felt the pressure from his cock slowly increase and my hole start to slowly open and welcome his cock in it's tight, slippery, warm and slightly damp embrace. There was a second of pain as his cock eased gently past my first sphincter. He was half way in. He paused for few seconds and then started to gently rock back and forth each time penetrating a little further inside. Then that moment of pure delight as his bulbous cock pushed through the second sphincter and he was fully inside. He slowly eased his full length into me until I felt his stomach and his big hairy balls hard against my bum and balls. Slowly slowly he started to rock back and forth again the thrusts slowly growing in length and intensity until I was taking the entire length of his cock with each thrust. His hands were gripping tightly onto both sides of my pelvis as he pulled and thrusted harder and harder into my arse for well over a minute. I could hear his breathing quickening and deepening as he slowly grew to an explosive climax and his spunk ejaculated from his cock buried deep inside my anal passage in big spurts with each gasping breath.
"Stay inside me please Sir while I wank" I pleaded." He made no move and I quickly grasped my cock hard and expended great big globules of creamy white spunk all over the back of Mr Jacob's easy chair as I wanked my cock to completion.