My Appointment With The Head Mistress - Sex Stories

My Appointment With The Head Mistress

... her. "Now Carl, I want you to lay across my lap." I do as she says, embarrassed that Ms. Swanson will feel the hardness of my cock. She says nothing as she rubs my arse with what I find out soon is a bulletproof paddle with holes. Pausing momentarily Ms. Swanson says, “You are going to receive ten blows; each one will progressively be harder than the previous one. You will not make a sound or shed a tear, Carl. Do you understand?” “Yes Ms. Swanson, I understand.” The first blow is not that bad, the sting was mild. The next blow was definitely one I felt and it sent a bolt throughout my body. The third one had me fighting to not make a sound, and I felt Ms. Swanson move her thigh along the bulge in my trousers. I could not believe how sexually aroused I was getting with every blow and her nylon covered thigh rubbing against my hard cock. Pausing before the fourth blow, Ms. Swanson asks. “So you enjoy drawing provocative pictures of Ms. Applegate, Carl?” “Yes, I do.” I knew better not to lie, as the remaining blows of the paddle would be even harder than what I anticipate to come. Blow number five and Ms. Swanson’s thigh rubbing my cock was too much and I feel precum flow from my cock. There is so much, that my boxers and trousers become wet. If she knows, Ms. Swanson does not say anything. After blow number nine lands on my arse Ms. Swanson pauses asks. “Who else do you draw like that, Carl?” “You, Ms. Swanson, I draw pictures of the two of you together.” “What do you mean, ...

... together?” “Making love, together.” “Oh, I see, and is there anyone else in some of the pictures with Ms. Applegate and myself?” ‘Yes.” “And who would that be, Carl?” “Me, Ms. Swanson.” Then the tenth blow lands so hard that my cock jerks against her leg and sends forth more precum. She gently rubs my arse with her hand. “Stand up Carl, I want to see you.” “Oh my Carl, I see that you enjoyed the spanking.” Looking directly at my crotch and the obvious wet spot on my trousers. Suddenly there is a knock on her door. I notice that Ms. Swanson has undone three more buttons of her pink blouse. Now I have a view of her pink, lace bra and her cleavage. My cock twitches at the sight. "Come in Ms. Applegate." With my back still to the door, I hear Ms. Applegate enter and lock the door. She comes up behind me and whispers in my ear, “I hope you enjoyed your punishment, Carl.” Ms. Applegate walks over and sits in the chair that I had sat in. “Come here, Carl.” I go stand in front of Ms. Applegate. She reaches out and slides her hand along the length of the bulge in my trousers. “Mmmm, I see Carl enjoyed his spanking as much as I enjoy them.” I stand there not knowing what to do or say. Ms. Applegate’s statement takes me by complete surprise. “I am glad you enjoy it when I spank you, Toni. Carl has told me that he also draws pictures of us making love and that he also includes himself in some of them.” “Oh Carl, we would love to see them sometime. But now I must ask you to remove your ...