Helping Mom

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!

"Well, if you're chicken, we can forget the whole thing," I replied.

"No, I agree. But the spanking will be over my shorts," she replied with a smirk like she outfoxed me.

"Fine," I replied. "Let's play."

She rolled first and I doubled immediately; 10 swats. A couple of moves into the game, she rolled double sixes and got cocky, so she doubled; 20 swats. A few moves later, she tried to get her last man to safety and I knocked her off. I doubled; 40 swats. I had a good setup and it took her a couple of turns to get her man back on the board. She then made a tactical mistake and ran even though I was ahead. When I won, she ended up having three men still on the board.

"3 times 40 is 120," I replied. She moaned but her nipples were now hard as a rock and clearly visible.

"But I will offer you a deal. If you remove your shorts and allow me to spank your bare ass, I will cut that number in half."

"No way," she replied. "120 over the shorts."

She stood up and came over to my right side. She leaned over until she was lying across my lap. I surprised her by yanking on the waist of her tight shorts causing them to wedge in her ass and expose a good portion of her white cheeks.

"Noooo," she wailed loud enough for mom to hear.

I ignored her and started to spank that luscious ass. After I had delivered about 10 swats, mom called out, "What's going on in there?"

"Ashley is paying off her bet," I replied.

I began to spank her exposed cheeks harder making a louder noise. After another 10 swats, I saw my mother in the doorway.

"Peter, what are you doing?" she asked alarmed.

"Ashley decided the loser would get a spanking," I replied as I continued to wail on her rear-end. It was starting to get red and she was starting to moan softly. Even from this distance, I could see my mother's nipples pushing out her blouse. Over and over my hand landed on Ashley's exposed cheeks as my mother looked on. I finished with a hard flurry which got Ashley wriggling around my lap.

"Ashley, set it up again," I commanded. We had always played loser sets up the board. She got off my lap and gently sat on the couch and began setting up the board.

I looked at my mother and said, "Do you want to play the winner, mom?"

Ashley shot me a nasty look.

My mother looked surprised and excited.

"For the same stakes?" she asked.

"Yes," I replied.

"I don't think so Peter; it wouldn't be right," she replied softly.

"OK! I guess I will just have to keep wailing on Ashley's ass for the rest of the evening!"

With that, my mother returned to the living room. When she had gone, Ashley said, "What did you do that for? I thought we agreed to bring her along slowly? You may have scared her off."

"Relax. You couldn't see her from your position over my knee, but she was very excited as she watched me spank you. Anyway, I don't think she was scared away at all. I bet that is all she is thinking about right now."

"OK! Let's play!"

Again, prior to my first turn, I doubled and she accepted; 10 swats. A few moves into the game, she knocked one of my men off. On her following turn, she doubled; 20 swats. I left my man in her home and eventually she got desperate to get it out so she knocked me off again. In the process, she left open one of her men in her home area. I knocked her off coming back in. On my next turn I doubled; 40 swats. I had six men off before she got her man back on the board. She only managed to bear off 3 before I won.

Ashley was white as a ghost.

"Peter, I can't possibly take 480 swats," she said nervously.

"I will make you a deal; if you remove your shorts and allow me to spank your bare ass, I will cut that number in half. In addition, if you remove your top and allow me to administer half the swats to your bare breasts, I will cut the number to one third."

"Oh god, that is 80 on my butt and 40 on each breast. I don't know if I can take that," she replied still white. However, I did notice that her nipples were stiff again.

"Well, look at it this way. When mom sees me spanking your tits, she won't be able to resist. That is her best fantasy," I replied.

"I know but my breasts are so sensitive," she whined.

"I'll tell you what! If you will let me put clothespins on your nipples while I spank your ass, I will reduce it to one fourth. I'm sure we can figure a way to get mom back in here to see me apply them."

"Oh, my nipples are especially sensitive," she replied again whining.

"Stop complaining and decide which option you want. After all, this was your idea!"

"It was my idea but I didn't think you would take advantage of me!" she replied in an even voice.

"I didn't force you to double. You brought this on yourself. If you want 480 swats on your butt, that's fine by me!"

"No! I can't take that. I will accept your final offer," she replied.

"OK. Go get the clothespins. I will wait here," I commanded.

She looked at me and I watched her nipples get even harder. Apparently, not only did she get off on being punished but also on being told what to do. Very interesting! If I played my cards right, in the near future I could have two live-in slaves; my mother AND my sister.

"NOW Ashley," I said as she stood there starring.

That got her moving. She went into the kitchen and I could hear her searching. After a couple of minutes, she returned with two plastic clothespins.

"These are the only ones I could find," she replied holding them out for me.

I took them and attached one to my finger. It bit down hard!

"These will do fine. Now, once you take off your shirt and shorts, I want you to say in a loud voice, 'Peter, what are you going to do with those'. Hopefully, this will get her in here to watch me put them on you."

"OK," she replied.

"Ashley, I am waiting. Remove your top and shorts," I commanded loud enough for my mother to hear.

She looked at me for a moment then reached behind her neck and untied the halter top strap. She turned around and asked me to untie the strap at the middle of her back. I quickly untied it. She turned back around with her arms holding the top in place. Slowly, she lowered her arms and the top fell away. I was starring at her incredible tits; tan except for a small triangle covering the nipple area with large, pink nipples that were hard and long.

She looked me in the eye and I could see the lust within.

"Now take off those shorts," I said again in a loud voice.

As Ashley began to unzip her shorts, I sensed my mother's presence. This was confirmed when Ashley looked up and I saw her eyes go wide (and her nipples get even harder). She looked straight at me as she wiggled her shorts over her hips and dropped them. I looked down and starred at my sister's pussy. Her lips were puffy and glistening with moisture. She had only a thin strip of fine blonde hair leading directly to her secret spot. I heard a groan behind me from my mother.

"Ashley, step out of the shorts, place your hands behind your head and spread your legs," I commanded.

Without thinking, she obeyed. I quickly walked up to her and grabbed her right nipple between my thumb and forefinger. I rolled it gently eliciting a soft moan from my sister (and a corresponding moan behind me). I increased the pressure until I was pinching her engorged nub. The moans both in front and behind me got louder. I released it and was satisfied it was hard enough to sport the clothespin. I picked up one of the clips, squeezed it together opening it, placed it over the long, hard nipple and slowly allowed it to close.

"Aggghhhhhhh," Ashley moaned. "Oh god, that hurts!"

She was breathing hard and when I looked down, her juices were dripping down her thigh. Was she getting off on the pain?

I quickly repeated the process on her other nipple and stood back to admire my handiwork. Her nipples were being pinched wickedly by the clothespins. Her eyes were glazed over and the smell of her juices saturated the room.

I decided not to waste any time – I didn't want to break the spell.

"Alright Ashley, go and stand in front of the desk, about 2 feet away, spread your legs and bend over."

As in a trance, she did as she was instructed. When she bent over the desk, her ass and pussy stuck out perfectly. I went over to her, placed my foot inside one of hers and pushed it out further causing her feet to be spread out a few inches beyond her shoulders on either side.

"When I tell you to spread your legs, this is how far apart I want them," I instructed.

I then put my hand on her upper back and pushed her down until her tits were pushing hard on the desk.

"Aggggghhhhh," she moaned as the clothespins dug deeper into her nipples.

This position placed her ass at a perfect height for spanking and caused her pussy lips to gape. I went and stood beside her.

"Ashley, you have 60 swats coming. I am going to give you the first 40 with my hand and the last 20 with my belt."

"No, please Peter," she whined.

"Be quiet and take what you have coming, slut," I replied and slammed my hand into her exposed ass.

"Agghhh," she moaned.

I started spanking her ass hard. After a few strokes, I got into a nice rhythm; spanking one cheek for several swats them moving to the other. Back and forth I went as her ass got progressively redder and her moaning got progressively louder. Just as she was moving around too much for me to aim effectively, the 40 swats were completed.

Slowly, I removed my belt and folder it in half. Holding the side with the buckle, I pulled my arm back and laid it across both cheeks. She moaned again but seemed to stick her ass out further inviting another stroke. I obliged. I started rubbing her hot ass in between each stroke which got her moaning even louder. After the final stroke, I rubbed her ass and allowed my fingers to move south where they encountered a soaking wet and wide open pussy. As soon as I touched her clit, she exploded in an incredible orgasm.

I gave her a couple of minutes to calm down.

"Alright Ash, it is time to pay the rest of your bet. Stand up, turn around, place your hands behind your head and spread your legs," I commanded.

She did as instructed and I was pleased to see her spread her legs wide as I instructed earlier. I approached her and removed the clothespins. She started moaning loudly as another wave of pain hit her as the blood rushed back into her abused nubs.

""Now, you will receive 30 swats with my hand on each breast. Do not move from that position until I tell you to!"

"Peter, please be gentle," she said softly.

I drew back my right hand and slapped the side of her left breast. It was not as hard as I could but it wasn't gentle either. Without pausing, I used the backhand motion to slap the other side of her left breast. She moaned but at the same time arched her back to give me better access to her luscious tits. Over and over I slap her breast to a symphony of moans (from in front and behind). By the time I was done with the left one, it was red and her juice was dripping down her thigh again. I took a quick look over my shoulder to see my mother with her eyes closed, one hand pinching her nipple and the other rubbing her crotch.

I spanked the other breast. When I was done, I grabbed both her nipples and pinched them hard. Again, she exploded to another intense orgasm. I put my arms around her and hugged her.

"We are done for the night," I whispered softly in her ear.

I heard my mother behind me say, "I want to play the winner!"

Ashley and I looked at each other and smiled.

"For the same stakes?" I asked.

"Yes!" she replied immediately.

"OK! Why don't you go change into more appropriate clothes and I will set the board up," I replied.

(To be continued)