He looked at me doubtfully then told me to tighten my dress by pulling it together at the back then had me turn slowly to get a better idea of my 36,23.35 figure. Then he looked at me thoughtfully and spoke.
"I suppose you could prove it by asking me for a spanking right now."
I gulped, hesitated for a moment thinking of how much padding was provided by my wool dress, slip and panties then said.
"Would you give me a spanking now. Please?"
Fear and excitement was rising as he led me into his conference room. I was wondering why I had added, please, to my agreement as he pushed a button by the door that caused a "click" in the front door as it locked.
He had me bend over the table till my breasts had flattened then started taking off his belt saying,
"This is one of the instruments I use for punishment."
I was relieved as I had been expecting a nasty wooden paddle like my principals. I thought I would barely be able to feel the belt through my clothes and thought he was just testing my willingness to submit. This idea left me as he pulled my dress and slip up over my back. I blushed as I realized he could see my slightly tattered bikini panties.
He brought the belt across my butt several times but not very hard. It just stung a little and was more exciting than painful. When he quit it was tingling a little and as I reached back to rub it with both hands I realized that somewhere along the line he had pulled the back of the panties into the crack of my ass and I was rubbing my nude cheeks.
"Well. What do you think about your spanking."
"It is kind of embarrassing to be spanked on the bare but I guess it is alright. If I do anything wrong I would rather be punished for it than feel guilty, or especially to be fired."
"Yes I understand but I give different punishments for different offenses. Wait here."
He went over to a closet and came back with a whip! He handed it to me to inspect. It had four leather belts about an inch wide and maybe sixteen inches long sprouting out of a handle. It had been soaked in oil or something. The leather was very soft. I thought that this would make it less harsh but actually it just made it heavier and more flexible so every inch of it could contact the skin.
I was so lost in thought feeling the handle and thongs with my fingers that I was startled by his voice.
"Does that frighten you?"
My butt was still tingling a little and I was curious about the way the whip would feel.
"No not really. It doesn't seem too bad. I don't think it will bruise me like the paddle my principal used on me in school." Actually the thing excited me. Spanking with the belt seemed childish. A whip seemed more exotic and I flashed to a picture I had seen in a history book where a black woman was being whipped on her bare back.
He said, "Good. You are used to the concept of corporal punishment. Did it improve your obedience?"
"Oh yes! He really hit hard and my bottom would be sore for hours. I really tried to avoid spankings."
"Yes I used to use a paddle over clothes but my secretary complained about the long lasting pain and suggested using my belt saying that the lesser pain could be made up for by the additional humiliation of having it hit naked areas. It seemed just as effective while allowing her to get back to work without fidgiting in her chair." I went on to say, "I suppose this would be used on bare skin too? Even on other places besides my butt?"
"Yes, of course. Take off your dress."
I was shocked for a moment but then thought he had already seen my bare butt and my breasts were completely covered with my bra. I unbuttoned the front and pulled it over my head. It wasn't enough as I expected.
"Take off the slip."
When I stood before him in just my bra and panties he told me to turn around slowly. I blushed again as I realized he would be looking at my still bare ass cheeks which after the spanking were probably glowing red. It had been quite awhile since I had been so naked in front of a man. This man was quite handsome. I naturally became a little excited at his reaction.
"You have a beautiful body. You should flaunt it, not hide it in sacks. Go over to the mirror and look at your butt."
I went over to a large mirror and turned my back to it to see my butt. It was red but no welts or bruises like the paddle had made.
"Ooh it is really red. I am surprised the spanking did not hurt more."
"It didn't because I started with light spanks incrasing the severity as you became used to it. You have seen your butt. This whip will cause an even darker red and possibly welts over more of your body. Would you rather leave? I will understand if you do."
I decided this must be a test and I had no intention of failing. Besides if it was too bad I could leave at any time.
"I don't want to leave. I want to prove I am willing to suffer if I do not please you."
"I see. You ralize you have done nothing wrong but are willing to suffer as if you had?"
"Yes. I should know what will happen if I do something wrong."
"Good, now lie down on the table."
I climbed up on the table and laid down on my stomach. I felt my panties being pulled down and off my legs. I did not protest because my butt was already naked and my pussy was hidden by the table and my tightly clenched legs. He went around the table to my head and told me to put my arms out in front of me. When I complied he unsnapped my bra and pulled it off my arms. I had to gasp as it dragged against my nipples that were pushing on the table.
By now I was getting really excited over lying naked on the table awaiting an experience I could not imagine.
I realized this was not going to be over in a short time as my spanking had when he said, "I have found that a light whipping over a longer period is just as effective as a short severe one and it has the advantage to you of leaving no residual pain."
I noted that the term "Spanking" had been replaced by "Whipping" to explain why my back was now bare too. Somehow whipping seemed more appropriate for a grown-up rather than the more childish spanking.
He began lightly whipping me just below my shoulders then moving down. I was relieved to find it did not hurt bad at all. There were just light stings that left tingles and as he slowly worked down the stings and tingles excited me. the sensation was even greater when the whip began hitting my butt and then the top of my thighs so close to my pussy my clitoris began tingling. He stopped and I felt frustrated and clenched my thighs together to try to keep the tingles on my clitoris.
Then I realized it was not over when he said, "Turn over."
This was a little too embarrassing. It had never occurred to me that my front would be hit. All corporal punishment had been just to my butt and sometimes my thighs but I felt committed now. Incredibly the thought of having my front whipped excited me the tingling sensation may be increased.
He became impatient while I thought about it and said, "Well?"
"I'm sorry." I clamped my legs together to hide my pussy and put my hands over my breasts to hide them as I made the turn. He pushed my legs down flat to the table and then started lashing me lightly starting at my belly-button and ranging up and down from there. It stung a little more but at the same time it was very thrilling. I was beginning to breathe in short pants when I felt the whip at the level of my pussy-hair and felt some disappointment as he slowly worked up towards my breasts. When he had slowly worked his way past my navel I felt this incredible need to stretch. I whimpered as I realized that I wanted the sting to fall on my breasts. My body seemed to take control as my hands left my breasts to go behind my head. I was stretching so tight I could feel my belly sinking toward my backbone as my breasts rose. He began to hit a bit harder as the first lash hit the base of my breasts. They seemed to swell and throb as he covered every inch. I continued stretching as I imagined I was tied tightly to keep me from trying to avoid the whip. It seemed to give me an excuse to accept this pain and humiliation. I had to gasp at the much sharper pain as the thongs hit my nipples but even this was thrilling and I watched my breasts shudder with the lashes with fascination. When he got to the top of them he began to work his way back toward my crotch. when he had worked his way down to my navel I wanted more! I slowly began to spread my legs. After a few lashes across the lips of my cunt he walked around my legs to face my pussy and put lash after lash full on its face till I went into the most glorious orgasm I had ever experienced!