A visit with my Headmaster
This Fictional Story is written by Jennifer and contains explicit sexual material and situations involving consenting Adults No reference to u******e persons is intended or implied. No reference to real Persons dead or alive is intended or implied.
It had been a couple of years since I graduated from that Private Girls School when I ran into my old Headmaster, Mr Weatherby, at the shopping mall. We stood there for a while chatting about the past when he made an odd comment saying that in all the time I went to school there he never had a reason to cane me. I blushed at the comment and replied that it was a good thing that he didn’t know everything that went on or he would have had good reason to cane me. He looked at me over his glasses and said, I think you should come around to my office after school on Friday and we will have to discuss this matter and then he laughed but added that I should come anyway and we could catch up on what everyone was up to. I agreed and said I would come around 4:00 P.M.
Friday rolled around and I was getting dressed to go see my Headmaster, but as I stood in front of the mirror in just my stockings and high heels I thought about him saying that he never had good reason to cane me. I turned my back to the mirror, pushed out my bottom and while looking over my shoulder imagined what his reaction would be to see me like this, but as I stood and pictured nice long thick purple cane strokes on my bottom my pussy was quickly becoming very wet. I shook off the notion and continued getting dressed but just in case things did go that way I made sure that the skirt I wore was short enough to show the tops of my stockings when I sat down and also a thong panty so my bottom would be completely exposed. When I finished dressing I checked myself over in the mirror and thought, oh Jennifer you do look like a naughty girl I hope I am not making a big mistake and with that headed out the door.
I arrived at the School at 3:55 and made my way to the main office, as I entered the secretary said I would have to wait a few minutes because the Headmaster was dealing with a young woman and they would be done soon. The sounds coming from the closed door made me freeze to the spot, the unmistakable sound of cane meeting young female flesh and then crying filled the room. I stood there straining to hear trying to imagine what it would look like and all the while unaware of my pussy starting to lubricate. After what seemed an eternity the door opened and a very distraught young lady face stained with tears and walking stiffly passed by me and out the door. My Headmaster spotted me and with a big smile called me in and told the secretary that he did not want to be disturbed from then on. I looked around the office, the chair that the girl had bent over was still there the seat still wet with her tears, the cane was on the desk and he still had his sleeves rolled up. My whole body was quivering, flushed and aroused and I am sure he noticed, but he said nothing just wiped the seat of the chair and asked me to sit down. He apologized for the scene that had just taken place and again mentioned that he had never had to do that to me, but then added how I had said there were things he didn’t know about and maybe I would like to tell him now. I knew where this would head so I took a deep breath and started to confess everything, all the while he fiddled with the cane and kept looking down at my legs. As I talked I kept moving around on the chair so that my skirt would slowly work its way up my legs exposing my bare thighs and hips above my stocking tops but I realized that my pussy was soaking my little thong panty and was surely leaving a big wet spot on the chair. After a little while Mr Weatherby stopped me saying we both know what needs to be done here Jennifer, you have needed a caning for a long time and obviously you are asking for it by the way you came dressed today, I also am not naïve to the sexual implications here considering that you are an adult and in an advanced state of arousal. I could do nothing but agree with him and could hardly believe my ears when he instructed me to stand, remove my skirt and bend over his desk. The first thing he saw was the big wet spot on the chair and as he removed my thong he commented as to how soaked it was and then continued to say how pleased he was that I was so worked up because it would help latter.
He walked around the desk looked into my eyes and while holding the cane so I could see it described how he was going to beat me, He then asked if I agreed to this and accept his punishment, all I could do was nod yes. With a big smile on his face he walked back around to position himself behind me and wasted no time as I felt the first stroke of the cane land right across the middle of my bottom followed by an intense burning. I barely had a chance to take a breath and whack, another stroke, I gripped the far edge of the desk and held on tight as the strokes came fast and hard, whack whack smack smack. I started to howl, moan and groan, I could feel myself grinding my pussy into the edge of the desk as stroke after stroke started to blend the extreme pain in my bottom and thighs with the arousal in my pussy. I looked over my shoulder and I could see the lust in his eyes as he whipped the cane across my buttocks, he looked at me and I said whip me Sir, whip me as hard as you can, whip me until I cum and with that I spread my legs wide inviting him to do as he pleased. He gave me two dozen more strokes on the inside of my left thigh and then tossed the cane aside, he ripped off his trousers unleashing a huge swollen cock and without pause plunged into my waiting open dripping pussy. He was impatient and pumped rapidly, his cock filling and stretching me as I pushed back against him desperate to cum. Within seconds I could hear him grunting as he held me tight and load after load of hot sticky cum erupted into me pushing me over the edge as orgasm after orgasm swept over me. After a while and when his cock subsided he sat down in the chair and pulled me onto his lap, we sat there for quite some time just holding each other and not saying anything until I finally looked him in the eyes and simply said thank you for the best experience of my life we will have to do this regularly. I looked over his shoulder and noticed that we had not completely closed the door to his office and his secretary had witnessed the whole thing, we smiled at each other as she quietly closed the door and I thought next time we will have to include her.