I returned home for the summer after my sophomore year at college. Soon after I got home, my sister Ashley told me she had something important and private she wanted to show me.
Before I continue, I should probably describe my mother and my sister. Both are incredibly beautiful with great, voluptuous figures. My mother is a fiery redhead with wavy red hair to her shoulders, deep blue eyes and full lips. She has very large, firm tits, (40DD the last time looked at her bra), a thin waist, flaring hips, a nice ass and long shapely legs.
Ashley is a natural blond with long, wavy hair that reaches down to the middle of her back. She has a very pretty face with baby blue eyes, high cheekbones and luscious, full lips. She looks a lot like Jessica Simpson. She has a figure like her as well with large tits, a tiny waist, a tight, heart-shaped ass and long legs.
A few minutes later, I was in Ashley's room.
"A couple of weeks ago, I came home early from college. Mom was not around and I noticed a chat session was active on the computer. When I went over to look, I was shocked to see the name of the chat room was 'The Punishment Room'. Investigating closer, the nickname being used was 'Naughtycunt'. I surmised it must be mom's. I quickly hit the print button. Here is what she was chatting about."
She handed me several sheets of paper with printing on them. I read the entire chat session. My mother was apparently talking with a man and a woman. They started by asking her if she fantasized about being punished which she indicated she did 'all the time'. They asked her if she ever lived out those fantasies. My mother indicated that she hadn't been punished since the last time her father spanked her when she was 18. They then grilled her about her fantasies. My mother told them she fantasized about having her ass, tits and pussy spanked and whipped. It was clear from the text that her favorite fantasy was about having her big tits punished; having them spanked and whipped, wearing wicked nipples clamps for hours and even wearing special bras with sharp tacks in them. They went on to ask my mom if she would ever act out those fantasies. She said not unless she completely trusted the other person or people. Finally, they asked her if she had any other fantasies to which she reply she wanted to be forced to expose her body to strangers.
Needless to say, I was stunned.
"Wow," I said.
I looked at my beautiful sister. She had been reading it over my shoulder. I was surprised to see that her nipples were hard and she was breathing hard. She was excited. It was then I realized I was hard myself.
"I think we need to help her fulfill her fantasies," my sister said.
"What?" I replied.
"We should help her fulfill her fantasies. She will never find anyone she trusts more than you and I!" she replied.
"What do you want to do? Go down there and ask if she would mind going over your knee for a good spanking?" I asked.
"No! We will need to bring her along slowly if this is going to work. I have a plan," she replied with a smile.
"Let's hear it," I replied.
"Well, tonight you and I will play backgammon and the winner will spank the loser so she can hear," she replied.
"Ashley, you do know that I am a champion backgammon player," I said.
"Of course, that's why I chose it. I think she'll get much more excited seeing you spanking me than the other way around," she replied.
"I still don't see how this is going to get us any closer to her fantasy!" I stated.
"This is just the first step in my plan. I am going to wear more and more revealing clothes over the next few days and encourage her to do the same. My hope is that one day, she will cross the line by wearing something too revealing. Then, you can call her on it and punish her."
"Well, it is a plan; I'm not sure how good it is," I replied.
"What are you complaining about? You will get to spank me and see me dressed like a slut even if it doesn't work. Besides, do you have a better plan?"
"I might. But I will go along with yours for now. If I don't think it is working, I will put mine into effect."
"Fair enough," she replied. "Are you going to share your plan with me?'
"I am still thinking about it. I will share it with you if I decide to implement it!"
"OK!"
"I am not sure me spanking you just once is going to do the trick. We may want to repeat it several times over the next few days."
"You just want to get me over your knee more," she replied with a giggle.
"Hey," I replied with my hands up in front of my chest, "it's your plan. I'm just trying to maximize the probability of success."
"Well. I thought we would play 2 or 3 games tonight," she replied.
When I didn't reply, she said, "Now get out so I can get ready."
I went back downstairs and sat in the living room with my mother. A few minutes later, Ashley came down with the backgammon board under her arm. She had changed into a low-cut halter top and a pair of very tight and very short shorts. She was also wearing sandals with straps up her calves and 5" heels. To my chagrin, I got hard again as I watched her strut around with her big tits bouncing.
"Peter, do you want to play a game of backgammon? I've been practicing and I bet I can beat you," she replied trying in vain to suppress a smile.
"What's the bet?" I asked.
"Whatever you want," she replied. "But I don't have any money so it will need to be something else."
"OK, go set it up and I will be there in a minute," I replied.
A couple of minutes later she called out from the family room that she was ready. I excused myself and left. I had been thinking how to make this as realistic as possible.
I sat down in front of the board and said, "OK, each point is worth 5 swats and that will increase with the doubling cube."
"That's a bit high, isn't it?" she asked nervously.
"You said the bet was whatever I wanted," I replied with a smile.
"You wouldn't take advantage of your little sister, would you," she replied. Even though she seemed nervous, I noticed her nipples were getting stiff again beneath her tight top. She definitely was excited at the prospect of getting spanked by me. Maybe mom wasn't the only one in the family who had secret punishment fantasies!
