I have been fantasizing about this moment for a long time, but now that it is here, I am a bit scared of the choice I made. I look at Brimstone's shapely thighs, but I am thinking more of my skinny ass lying bare and pointed up at her. She is holding the cane that will soon be striking my bottom. She said that she would not raise blood unless I was in "deep trouble," but then she said that I was in "deep trouble." I want to run, but I don't really have a choice. She had the goods to blackmail me; tapes where I was trespassing in her room like a cat burglar, really a peeping tom and where I was agreeing to be her slave while kneeling naked between her thighs. The first was illegal and the second was embarrassing. But I wanted to put off that whipping as long as I could. "Do you want me to take off my underwear?" The thong may have been called a man's swimsuit but honestly it was nothing more than lingerie for men and would do nothing to protect my me. It was obvious now that she had only given it to me in order to make me feel exposed and helpless; Why should I participate in the pretense, if it gave me 30 seconds more before that cane would leave a stinging red line on my backside?
My supervisor looks at me seeing right through to my hesitation, "Don't put it off, John. The longer you hesitate, the harder my spanking will be." She pats her thigh again and it looks enticing no matter what sort of pain may come with laying across it. Along with the submission and humiliation will surely come the gentle caress of her hand and the tender mercy of a relationship that is shifting from professional to personal. In my heart, I have been wanting this.
I want to put my jeans back on so the anticipated pain could be minimized. That is not going to happen. Carefully more like I am an old man with a back ache than a young man showing off tight rounded butt cheeks to a woman, I step forward and start to lie across her lap.
She stops me, "There is one thing we have to do." She uses both hands to slide my dick out of the grey cock holder. She does not take the swimwear off, but tucks it up underneath my balls to project my soft cock a little farther out. She gives the cock a gentle caress and it shifts as a reflex action towards getting hard. She asks, "Doesn't that feel better? It looks prettier."
I know the proper reply, "Yes, Brimstone."
She strokes my pubic hair and comments, "We are going to have to do something about that. I like my boy slaves properly trimmed, perhaps waxed." She orders, "Now, lie down."
Having all preliminaries and delays finished, I lie across her lap, feeling very exposed and very vulnerable. My ass is skinny and soft. I ride bike, but that is a means of transportation, not exercise, most of my time is spent in front of the computer or sitting in class. I probably look like a little boy and I certainly feel like it. Brimstone was older than my mother and shaped more like other men's mothers than mine did. I had a fetish for plump women and she fit the bill. I thought women with womanly curves and large breasts were sexy and comforting in a way that my own mother is not, but now I am worrying how deep the trouble was that I got myself into. She puts her hand on my ass and it feels warm soft and comforting for a second before she smacks it down on my cheek. "OW!"
"Not 'Ow!" Thank you, Brimstone!" she corrects as she picks up the cane.
She had not been kind with that first slap and I could feel the sting on my buttock rising up. I knew her tone of voice and she is not angry, only unyielding, I say, "Thank you, Brimstone." Almost immediately, the cane strikes my other cheeks just as harsh as before. She is not trying to be kind at all. "Thank you, Brimstone." She continues; Each blow causes my butt to sting and become sore like nobody has ever treated me before. "Thank you, Brimstone! ...Thank you, Brimstone! ...Thank you, Brimstone! ...Thank you, Brimstone! ...Thank you, Brimstone! ...Thank you, Brimstone!" I lose track of how many times she spanks me, but my ass is feeling red hot and alive with fire. She slows down and starts caressing me between each blow the touch is comforting, but also a reminder of the pain and sting.
She stops and asks, "Did you like that John?"