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My New Girlfriend Kay Part 4

Ann demonstrates her paddles on Clyde
My New Girlfriend Kay P 4

After Ann left, it gave Kay and myself plenty of time to eat lunch and be alone together. As I have mentioned in the past, Kay is a really good cook, and everything she made tasted great. She even made me a blueberry pie. When we had eaten out, I always ordered a blueberry pie, so Kay knew what I liked as far as food goes.

After the food was put away and I helped Kay with the dishes, we sat on the couch and talked. “I like the fact you like my girlfriend Ann and that you are willing to be spanked. It shows me that you really like me and would do almost anything for me.”

“Yes. The more I find out about you, Kay, the more I enjoy being with you. You are such a great cook, we seem to have the same values, and I hope we can continue dating.”

“I also like the fact that you are going to allow me, Ann, and other women to spank you.”

“I am going to allow it to happen, because it pleases you, saves me money, and I like to be around dominant women who like to take control.”

Our conversation went on like this as we held each other really close. Then I looked up at the clock and saw that it was almost two o’clock. “It’s almost two o’clock,” I told Kay. “We better leave now.”

“Clyde, stay in your lounge pants and just put on shoes and socks. Also remember to bring your bag. I’ll do the driving.”

“But I don’t want to go out in public with only my lounge pants on and no underwear,” I protested.

“We’re going to be late. You better follow my orders,” Kay angrily responded.

“Can’t I just change into my lounge pants after we get there?”

Kay then sat on the couch and said, “Come over here right now. I am going to take the time to spank you before we leave.” I walked over to her and she immediately pulled down my lounge pants so I was naked from the waist down. “Now lay over my lap!”

Kay immediately started to give me a hand spanking.

“You need to learn to always follow my commands and orders.”

Kay kept taking to me as I was spanked.

“You can expect to be spanked if you ever question me again.”

I knew I better just be quiet as I was being spanked.

“Do you understand?”

All I could say was, “Yes! Sorry Mistress.”

My spanking continued.

“This will not happen again,” I said.

Then Kay gave me five very hard, quick swats.

“Get off my lap, put on your shoes and socks, and grab your bag. If we are late, I will allow Ann to spank you for causing us to be late, and that will take place before the paddle demonstration.”

Then we quickly got into Kay’s car and arrived at Ann’s woodworking shop. On the way over there, I apologized again to Kay, but she didn’t say a word.

Once we arrived at Ann’s shop, she was waiting for us at the front door of the shop. As Ann locked the door and put out the “Closed” sign, Ann said, “You are ten minutes late. I was wondering if you forgot about this appointment. Go to the back room. Two women are waiting for the demonstration.”

“Clyde made us late and I told him he deserves a good spanking from you as part of the demonstration. I also had him bring his bag, so you can use anything that is in it,” Kay told Ann.

When we entered the back room, there were two women about my age standing there. Ann said, “This is Jane and Dawn. Jane is interested in finding out more about how to spank her husband and Dawn is curious about spanking her boyfriend. Jane and Dawn, this is Clyde, Kay’s boyfriend. He has volunteered to be spanked and to help me out with this demonstration.”

Then we greeted each other. After a few minutes Kay said, “Clyde was just hand spanked at my house and he knows he will be further spanked by Ann for being late. So this demonstration will be more intense than it usually is.”

“Clyde, take off your shoes and socks while I get the shoelace to prepare you for your spanking,” Ann said.

I was prepared to be spanked in front of strange women, but I wasn’t prepared to have it start out with Ann putting the shoelace on me. “Please, not in front of them!”

“You better do as Ann says and not complain, or things could get much worse.” Kay said.

So I took off my shoes and socks and stood close to Ann. She pulled down my lounge pants and had me step out of them. Jane and Dawn snickered since I already a full erection going. This was so embarrassing to me. Then I obediently put my hands behind my back and spread my legs.

As Ann wrapped the shoelace around my penis and balls she said, “You should try this. It makes a man maintain his erection a lot longer.”

After Jane and Dawn examined the shoelace around me Ann said, “Clyde, go over there and bend over my measuring bench.”

Since Ann had measured me before, I knew I needed to bend over it and grab the wooden handles in front of me. But this time, Ann extended the handles forward so I was stretched forward, and she lowered the handles so I was bent over the device.

I heard some rumbling in my bag and Ann said, “Now spread your legs for apart.” Now I felt the ankle cuffs put on me, and the cuffs being connected to the spreader bar. “Usually I don’t do this for a measurement or a spanking, but I want to make sure Clyde stays in place. You can see that his cheeks are already pink from his recent hand spanking and he was also spanked last night.”

“He is really pink.” “Yes, you can tell he has been recently spanked,” Jane and Dawn said.

“When Kay had me make the paddles for Clyde, she wanted a full coverage paddle. If you only buy one paddle, this is the paddle I suggest. Kay drew marks on Clyde’s butt as to how large she wanted the paddle, and I custom made it for her.” I felt a tapping on my bottom. “As you can see, one swat from this paddle covers his whole butt. Plus it has holes in it so you can swing it faster, and it is made of oak, so it is a very strong paddle. This paddle really stings whoever you are spanking. Let me show you.”

The paddle really did sting me as I was spanked.

“See. Even with three swats of this paddle, it makes a lasting impression on Clyde,” Ann said. “I also made her this paddle that is similar but it is only three inches wide. It also has holes in it and is made out of oak. This is good for spanking specific areas of his butt. Let me show you.”

This time Ann spanked me where my upper thighs meets my bottom checks and also in my upper inner thighs. Kay had never spanked me in those spots and I tried to move my legs together, but my legs were kept spread apart by the spreader bar.

Ann could see my reaction and said, “That really did hurt, didn’t it Clyde?”

I replied quickly with, “Yes, Mistress! I will be a good boy. Please don’t spank me any more.”

“But Jane and Dawn will still want to spank you plus I have a few more things to demonstrate on you,” Ann said to me. “So I advise you to take the spanking that you deserve without complaining.”

“I also sell these big and small wooden heart shaped paddles, and riding crops,” Ann told Jane and Dawn. “See how well you can get into those smaller places with this riding crop. So now you can try them out by spanking Clyde.”

When they spanked me they didn’t swing the paddles with the force that Kay and Ann used, but because of my recent spankings, it still stung my bare bottom.

“See how nice and red he is getting,” Kay said. “Clyde will be able to feel this spanking for a few days.”

Not only was the spanking turning my bottom red, but it was also making my lower torso feel very warm and I could feel it in my penis and balls. The shoelace also made me even more aware of my erection.

Then I felt many hands on my warm and tender bare bottom. “Yes, you can actually feel how warm his butt is.” I heard someone say.

“Let’s thank Clyde for letting us spank him,” Ann said as I felt the spreader bar being unhooked from my ankles. I thought I was verbally going to be thanked, but Ann guided me to the center of the room and the spreader bar was attached to my ankles again. Someone guided my arms behind my back, and the wrist cuffs were put on me and were connected.

Then to my surprise, some sort of blindfold was put on me so I couldn’t see. All at once, I was being spanked again, as well as my penis and balls were being stroked and played with. Being blindfolded I couldn’t tell who was doing what, but with my already big erection, soon I felt my cum exploding from my body.

I was soon released from the spreader bar and the cuffs, and allowed to relax on a chair. Meanwhile the women were talking and placing their orders with Ann. Now I had mixed emotions on what happened to me. My poor bottom felt on fire from the spanking, but yet the lower torso of my body felt so very warm and relaxed.

After that, I was finally allowed to put my lounge pants back on again and Kay drove me back to her place. But before we left, Ann gave me a lot of bubble wrap to sit on since my poor bottom was so sensitive from my recent spankings.

Kay fixed a nice dinner for us, and then we held each other, kissed, and talked. Before I left Kay’s house, she gave me an over the knee bare bottom spanking, while she told me how grateful that she had found me as a boyfriend. What a weekend that turned out to be.

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