Chapter 2: The Decision

Dana left my office fighting back tears. She composed herself quickly in the bathroom and left in her car. The game had started, but even I didn’t realize that Jim had some plans of his own for this little game. When Dana arrived at Jim’s house, he acted surprised to see her and invited her inside to his study. Dana tried to “professionally” convince him that this was an unfortunate error that was all her fault, but that he could count on the same excellent service in the future that he had always received before this accident. Jim was not moved. Soon Dana’s professionalism started to slip and she began pleading about how important this was to her and how there just had to be some way that she could make this right. This was the opening that Jim had been waiting to hear.

“There may be a way, Dana. I would need to know that you were punished in accordance with the pain that you have caused to me and my reputation. And I would need to find something that compensated the players for the enjoyment that they missed at the party.”

“Well I am sure that I could arrange for free stuff at another party, perhaps an even bigger one, for the basketball team. And, I guess, I could ask to have my pay docked to help offset the expenses of the free stuff.”

“Dana, I appreciate that gesture but I would need something more immediate and direct in order to keep my business. I believe that the old fashioned punishments were the best, the only ones that really worked. The one way that I can be truly certain that you have been punished to a degree that equals my pain is if you are soundly spanked here in my office.”

“I could never agree to that” Dana retorted.

“That is your choice. Thank you for stopping by, but our discussion is clearly at an end. Can you find your own way out?”

“Wait a minute, there must be some other alternatives”

“The alternative is for me to take my business elsewhere. You know my position on the matter. Goodbye.” At this point Jim turned around and started walking away from Dana.

In a soft broken voice Dana replied, “OK, if that is what it takes then I guess that is what I have to do.” Truthfully, with their financial situation Dana really didn’t have any choice and I knew that when I made this plan with Jim.

“This is how it will be Dana. Please understand that these instructions are all non-negotiable. You may leave, or you may do as I say. Those are the only two options. You will be spanked on the bare bottom here in my office. I will spank you 20 times with my belt. After that, members of the basketball team will spank you.

Dana came from a conservative family that believed in spanking clear into the teenage years. So even though it may have been 15 years since her last spanking, she had a good idea what to expect when she told Jim, “Let’s just get this over with”.

The basketball team members were expecting his call, and started over to his house immediately. But Jim didn’t wait for them to arrive to start Dana’s punishment.

“Remove your hose and your underwear and hand them to me.”

Dana reached modestly under her skirt and removed them.

“Tuck your skirt into the waist band and lean over my desk.”

Dana had slim hips and a firm bottom which created a beautiful sight bent over the desk. I know this because I arranged with Jim to secretly record and webcast the spanking. I liked seeing the spanking live, even if it was a lower resolution. And i couldn’t wait to see he hi-res video Jim was also shooting.

Jim did not hold back as he proceeded to give Dana 20 swats with his belt. He paused between each strike to wait for her to settle back into position. Carefully he changed the position where each stroke of the belt landed. But one after another, bright red welts appeared all over Dana’s beautiful ass.

Once she had finished crying and rubbing the soreness out of her bottom, Jim sent Dana to cut the switches. She was so distracted by the pain in her bottom that she didn’t even ask about putting her panties or hose back on before going out to the yard. The basketball players arrived while Dana was still cutting switches.

The senior co-captains of the team Jamal and D’wade were invited to Jim’s house to continue the punishment.

“Since your actions affected the players the most, I think it is only fair that they have a chance to participate in your punishment.” Jim explained.

Dana had been bent over the desk and only her panties had been removed. But that was about to change. Jim instructed her to undress all of the way and kneel on top of the desk. Dana seemed beyond caring and just wanted to get all of this over with, so she pulled her skirt down, lifted her top over her head and removed her bra. Dana’s breasts were on the smallish size, but they were firm with protruding nipples that looked like giant pencil erasers.

Instead of the switches, Jim gave each of the boys riding crops. Dana didn’t realize it, but this was an act of mercy on Jim’s part. With their strong bodies, youthful exuberance, and inexperience in whipping a woman, these two could cause serious damage with a belt, cane, or rod. The riding crop would sting, and make a pleasingly loud sound, but it wouldn’t leave any lasting damage.

The boys positioned themselves either side of Dana and took turns, alternating strikes to one cheek and then the other. While they deserved an “A” for their enthusiasm, their imagination was lacking. The spanking began as a steady rhythm of blow landing in the middle of each butt globe. Jim decided that it was time for some “coaching”.

“The steady rhythm is letting her get too comfortable. Take your time, she isn’t going anywhere until you are done with her. Make some of the strokes close together, but wait longer between other ones. Don’t let her know when the next one is coming; or where it is coming. Spread her legs a little bit wider, hit the top of her thighs, not just her butt. Make some strokes harder and others softer. The variety is much more effective.”