Jennifer and the Headmaster - Sex Stories

Jennifer and the Headmaster

... word in my story but he chose to use it. Of all the words to describe punishment “SPANKED” only describes erotic sexual bliss to me. I looked at him and taking my time so he could drink in his reflection in my eyes, I responded using an innocent little girl voice saying, yes Sir sometimes I need to be SPANKED, I emphasized. I could see his lip quivering trying to digest what I just said but then the buzzer sounded in the school and shocked both of us back to reality. I make a quick excuse that I need to get Sarah home and then get to work. He questions why I work in the evening and tell him as I am heading out the door that I am a cocktail waitress at an exclusive private club. I meet Sarah at the car and while I am driving her home I plot my next step with Mike Johnson, the die has been cast and I just need to play this out right, he could be the one that is for sure. The next day I arrive at the school a little earlier to give Mike and I some time to talk before the end of the school day. I no sooner pull up in front and he is out like a shot to greet me and help me out of the car again. I am the first to speak and I tell him that I want him to know more about Sarahs and my history. This time I am wearing an even more provocative dress, it is short but also very snug fitting and with my tiny waist shows my full bottom in perfect symmetry. Again we walk up to his office and I can almost feel his eyes burning into my bottom as I slowly climb the stairs to make sure he gets a ...

... good long look. We sit on the couch and while crossing my legs the dress pulls up to reveal my thighs right up to the side of my bare hip. I pretend to try and pull my dress down as though I am concerned with my modesty but I am actually adjusting it to give him the best view possible. The first thing he asks is why I am a cocktail waitress and also wonders how close Sarah and I are in age, pointing out that the other mothers are a lot older than me. Well I begin by telling him about my job and how I flirt with the wealthy men to get bigger tips, it is the best job I can get and actually pays pretty good so that I can keep Sarah in a private school. The next part I have genuine difficulty telling him and he quickly picks up on my nervousness. He tells me that I don't have to explain but I reply that no I want to tell you because no one else knows the real story. As I begin I notice that he is no longer looking at my legs but into my eyes that have begun to moisten with deep rooted emotion. Where to begin I say to him, Yes There is only f******n years between me and Sarah, I got pregnant from the boy next door at a very young age obviously. We would play together a lot and he used to spank me every time we played, I enjoyed the play spankings and that was all we did but then just before he moved away he wanted to do “it” just once. Well that was all it took and now I have my most precious thing on earth named Sarah. I went on to explain that my mother basically raised both of ...