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My New Girlfriend Kay Part 2

Clyde goes on another date with Kay, with many surprises
When I left Kay’s house, she had me wear my new birthday undershorts home with me. She had me leave my other undershorts at her house. She also kept the paddle, but she would talk to me about it during our next date.

I had accepted being spanked by Kay since I wanted to find a woman for my life that was more dominant and was in complete control, and I thought Kay might be the perfect woman for me.

Kay and I talked during the week, and we set up our next date to last all day on Saturday. I was to bring a duffle bag with me of different types of clothes. That is, she wanted me to be able to be casual around her house, and also able to take her to a nice restaurant. I was to also bring an empty smaller bag with me, and I would find out later why. But first she wanted me to dress in jeans and because she wanted me to go to an antique store to pick up something.

When she had dropped me off from our second date, she remembered that I drove an older SUV. I told her that I would clean it out so I would be able to help her with it. I was happy because now I was going to work together with her on a project.

Since the antique store opened at 10:00 AM, we decided that I should arrive at Kay’s house at 9:30. That way we could pick it up at 10:00, and we would have the rest of the day to spend together.

Well, I tend to put things off until the last minute, so I got up early Saturday morning to shower and eat breakfast, and to clean out the SUV. I had bought the duffle bag and a large bowling bag earlier in the week, so I also had to pack that bag. I didn’t allow enough time to do a good job of cleaning out the SUV because I had to leave to get to her house on time.

I was proud of myself because I arrived at her house right at 9:30. When she met me at the door she was wearing some very tight blue jeans and a nice red top. Again, Kay was wearing her wonderful perfume and we hugged at the door.

“Let me put your two bags in my house, then we should leave for the antique store.”

When she got into the passenger seat of my SUV she said, “Clyde, I am disappointed in you. You told me that you would clean this vehicle up before you came over.”

“I’m sorry. I wanted to make sure I was at your house on time, and I didn’t allow enough time to clean it up properly.”

“I will deal with that later today. I am just happy that I will be able to get this great find to my house today.”

When we got to the antique store, I was surprised to see what her great find looked like. It was about three feet wide, and it had three steps on it. It must have been used in a library or somewhere where they needed something to stand up higher. It was about 32 inches high, and was made out of sturdy dark oak. It was sort of heavy, but I was able to lift it into my SUV by myself.

When we arrived at Kay’s house, I was surprised because she had me put it in the middle of her living room. Then we sat down on the couch together. On the coffee table was a wrapped gift box. “I have another birthday present for you. Open it up.”

When I opened it, I was surprised what was inside. There were four pairs of lounge pants.

“These are all cotton, and they have a drawstring, so I know they will fit you. I bought four pairs so that you could keep three here, and you could carry one pair in your smaller bag. When you are at my house, I want you to wear them with no underwear underneath. I also have cleared out a part of one of my dresser drawers, so you will know where to find them. Follow me into my bedroom and I will show you the drawer.”

When I followed her into the bedroom, she pulled out a drawer that had her panties and bras in it. She had taken three of the pairs of my lounge pants with her, and she opened the drawer and put them in it. “Now I don’t want you touching my bras and panties, but I want you thinking about me whenever you come in here to put on your lounge pants. Since we will be here awhile, I want you to change into your lounge pants right now.”

When I saw her bras and panties, plus being in Kay’s bedroom, all of this gave me an erection. So I said, “Aren’t you going to step out of the room so I can change?”

“Clyde, I have spanked your bare bottom and also have made you cum, so I have seen everything. I am staying right here.”

This was only my fourth date with Kay and I was still self-conscious about my body, even though she had spanked me. But I undressed in front of her. Before I put on the lounge pants she saw my erection and said, “I like what I see, that is one of the reasons why I like you as my boyfriend.”

Then we went out to her living room. “Before we do anything else, I want to make sure the thing I bought at the antique store will work the way I want it to. I need your help with this.”

“Sure, I want to do things together with you,” I told Kay. “What do you want me to do?”

She led me over to the piece of furniture, and had me stand in back of it. “Now spread your legs and lean over and grab the bottom step.”

When I did so, I realized that my bottom stuck out and was elevated. Next, I felt Kay pull down my lounge pants and she said, “Now step out of the lounge pants and spread your legs again. I think this will work very well to spank you. Now hold your position while I get my paddles.”

Once she returned from her bedroom, I complained, “I don’t know why I deserve a spanking. What did I do wrong?”

“There are many things you did wrong. First, you didn’t clean your car very well, next you wanted me to step out of my bedroom while you changed clothes, and you also have been questioning me all morning. I need to teach you to respect me better.”

“But I am sorry. Please don’t spank me,” I said.

“Remember our last date. You said you would accept being spanked by me. So shut up and stay in position.”

I knew Kay was right and I remembered how Kay wanted to be addressed when she spanked me, so I said, “Yes, Mistress. I didn’t think you would spank me so soon, today. Can’t it wait until later?”

“You will learn that I like to punish you as close as I can to when you have offended me. Also, your complaining will add a few more swats to your punishment. I will start with the new paddle I got you for your birthday.”

Kay showed me the paddle. It was made out of leather and it was about the shape of a ping-pong paddle.


“Ouch! That really stings,” I complained.


“Stop complaining. I want to make sure you feel your spanking.”


Then she showed me a wooden paddle with some holes in it. “I don’t want to spend a lot of time spanking you right now, and this paddle has always given me good, quick results.”


I could really feel that paddle. It had been a while since I had been spanked, and I didn’t remember it stinging so badly.

“Your ass is turning red. Now I know you can feel it.”


“Please stop. I will be good!”

“Just a few more. This will be a reminder to you to respect me better, if you want to date me.”


“That should last you for a while. Now I want you to stand up but don’t rub your bottom and don’t put on your lounge pants yet. I do want you to carry that new thing I bought downstairs and I want you to help me work on a new project.”

So I followed Kay down the stairs with the new piece of furniture and she unlocked a door and turned on the lights. “I can’t have that in the middle of my living room, so I want to make this into a special room. We need to go to the hardware store and get hooks for my paddles and other spanking implements, plus other things to make this into a spanking room.”

Then Kay had me carry in a wooden straight back chair, a small dresser, and several full-length mirrors. All of this she had scattered in various places in her basement.

Next we went back upstairs and I was allowed to change into my jeans and underwear, and Kay drove the car to the hardware store. It felt a little embarrassing buying all of this stuff that I knew I would be putting into this special room, where I would be spanked.

After we put the stuff into the trunk of Kay’s car, she led me to a special shop several doors down from the hardware store. The store was all full of different wooden art pieces along with specially made wooden bowls and spoons that could be used at home.

After a while, a young woman wearing jeans and a t-shirt greeted us. “Clyde, this is my friend Ann, who makes all of this wonderful wooden art. Ann, this is the new man I am dating, Clyde,” Kay said.

“Glad to meet you, Ann. You are really skilled at what you do,” I said.

“Glad to meet you too, Clyde,” Ann said. Then she turned to Kay and asked, “Should I temporarily close up the shop? Do you need something custom made again?”

“Yes, I do want something custom made today,” Kay said.

Then Ann locked the front door and led us to a room in the back of the store. Inside the room were various wooden paddles and a piece of strange furniture in the middle of the room.

“I want Clyde to buy two custom made paddles by you,” Kay said. “I want you to measure him so that they will be very effective, like you have with my other dates.”

“Okay Clyde, I want you to walk over there, drop your jeans and underwear, and bend over that,”

Ann said, pointing to the piece of furniture in the middle of room.

I looked over to Kay and said, “Yes Clyde. You better hurry up and follow Ann’s directions, or I will spank you again right now.”

I felt very embarrassed but I dropped my jeans and underwear and bent over. “Now grab those two handles in front of you,” Ann said. After I grabbed the handles, Ann did do something so the handles moved forward, and my back was now straight.

“Do you spank Clyde with his legs apart?” Ann asked Kay.

“Yes, I do,” Kay, answered.

Then Ann bent down and took away my jeans and underwear. “Now Clyde, spread your legs apart, the way Kay likes them.”

After I thought I had my legs spread far apart, I felt a tapping on my inner thighs. “Just a little more,” Kay said. Now I really did feel embarrassed with my penis and balls dangling, completely exposed between my legs.

“Kay, take this marker and mark Clyde where you want the paddle to land,” Ann said.

Then I felt her mark four different places on my exposed bottom. Next, Ann measured the marks and asked, “Now do want one wide paddle and one thinner one made out of oak again?”

“Yes. And also stain them so they aren’t too light or too dark.”

“Now I can put two different types of holes in them. Do you want to try these out and see the difference?” Ann asked.

“Okay. This way I can also see what effect the have on Clyde’s bare skin,” Kay said.


The paddle stung more than what Kay has used on me in the past. Then I felt her hands on my bottom.


“I think I like this paddle better. With the different size holds, it swings faster and it leaves a bigger impression,” Kay said. “Clyde is going to take me out to dinner tonight, so could you deliver them after I get home?”

“Yes, I should have them ready by then,” Ann said. “You also want Clyde’s name on them too, right?”

“I like that personalization of the paddles,” Kay said.

“Well Clyde, you can stand up now, here are your pants, and then you need to pay me in advance. It will be nice to see my hard work be put to a good use,” Ann said.

So I paid Ann for the paddles. It felt somewhat embarrassing to me to first pay for the stuff at the hardware store and now the paddles, knowing that most everything would be used in spanking me.

Next, we went to a fast food place and quickly ate, so that I could get back to help Kay fix up the spanking room. Once we arrived back at Kay’s house, she had me change back into the lounge pants with no underwear. “After today, I want you to change into the lounge pants without me having to remind you. If you forget, I will help you remember with a spanking.”

“I plan on remembering,” I replied. Then we went down to the basement again. I helped Kay put up hooks and sketch around some of her paddles, so I knew where each one was to be put back in place. I found out that Kay likes things done a particular way, and only her way. I am also somewhat of a perfectionist, so I like that in Kay.

It was very good that we worked together in the room. I really got to know her better and this showed me that Kay likes to be in control at all times.

Time flew by very quickly and soon it was four o’clock. “Clyde, you said you would take me out to eat at a nice place tonight. Let’s go upstairs and you can shower in the main bathroom and change into your nice clothes. I will shower in the bathroom next to my bedroom, and then we can go out and eat.”

I brought with me a nice suit, complete with a white shirt, a red tie, and shiny black shoes. After I showered, I got dressed in the living room since Kay was in her bedroom.

The doorbell rang and Kay yelled for me to answer the door. I was surprised to see Ann.

“Kay called and told me the two of you fixed up a spanking room. I brought some stuff to add to it while you are eating. Then we can see how well the room works, after you get back. So show me what you accomplished,” Ann said.

So we went downstairs and Ann seemed impressed with the room. When we went back upstairs I was surprised to see that Kay was mad at me.

“Clyde, you made a big mess in the bathroom. If you weren’t all dressed up and I wasn’t hungry, I would spank you right now.” Then Kay saw Ann. “I hope you can spice up the room a little bit. I want to try out the new paddles on Clyde and also the new stuff you will install while we are eating. See you later.”

Then Kay and I went out the door and Kay drove her nice car to a very expensive looking restaurant. Now this date with Kay was getting very expensive for me. First I paid for the new piece of furniture from the antique store, second I paid for the stuff from the hardware store, third were the custom made paddles, and now this expensive restaurant. So after we were seated I said, “Wow! This is an expensive place to eat. Can we go Dutch or order very little?”

“I can’t believe you said that Clyde! Don’t you still want to date me? If you don’t want to eat anything, that is up to you, but you are paying for this meal. I was hoping we could have some good conversation, and now you destroying our new relationship.”

“I am sorry. I do want to keep dating you. Just forget I brought this up.”

“I was planning to try out the new paddles and spanking room on you when we got home, but now I plan to give you a more severe spanking. I also expect you to submit to the spanking without protest, if you want to keep dating me.”

“I will accept the spanking since I do want to keep dating you. You will hear no more complaints from me. I just hope we can have a nice dinner and a nice conversation, and we can get to know each other better.”

Then we did have this fantastic tasting dinner and the more we talked, the more I wanted to keep dating Kay. I had dated a lot of women, and I felt I had a real good connection with her. Also, physically Kay was a real turn-on for me. Kay was at my same height, had nice long legs, long blonde hair, nice round flowing breasts, a fantastic smile, and what always got me when I was around her was her special female scent and her perfume. Even when she first spanked me, it felt so good just to be around her. Plus, when we talked, she really paid attention to what I said and she always reacted to what I said.

So after we had our dessert and the check came for the food, I felt very happy and paid it without complaining. As Kay drove us back to her house, our wonderful conversation continued and I felt very lucky that I had found Kay as a girlfriend.

When we got to her house, she quickly went to her bedroom and then handed me a pair of lounge pants said, “Just change into these lounge pants and sandals, then go downstairs. Also, bring down your smaller bag you brought with you.”

So I quickly changed into just the lounge pants and sandals, and now I just realized that I was going get a good hard spanking. I had almost forgotten about it since I was having such a great conversation with Kay.

Once I got downstairs, standing in the middle of the room was Kay and Ann. “Ann modified the room and made some wonderful stuff that I can use with you,” Kay said.

“First, come over here and let me show you some new cuffs I made for both your wrists and ankles,” Ann said. “They are made from a new type of Velcro and I found some new clips that the hardware store got in. I made a set for the room and another set for your bag. Let me show you how they work.”

“Clyde, I expect you will not need to use the cuffs very much, but sometimes I will want you to come down here and secure yourself in place,” Kay said.

Then Ann showed me how easy and quick they were to put on. It was also easy to use the clips to clip them to something or to each other, but once they were clipped to something, someone else would have to release the clips. So I put the cuffs onto both my wrists and ankles.

“I also made two spreader bars for you, so one can stay here and a collapsible bar for your bag. The collapsible one goes together like this.” Ann said as she showed me how it worked. Why don’t you try putting on the regular spreader bar first?”

I found that it was very easy to use and it kept my legs spread apart.

“Now let me show you how this overhead rope system works. The end of it has an elastic strap on it with a ring at the end. I believe I have it set so you can easily pull it down. Try it.” Ann said as I was able to reach up for it. “Now clip your wrist cuffs into it and the elastic strap will pull your arms up over your head,”

I do so and now I realized that I was standing there with my arms over my head and my legs spread apart, and I was helpless. Plus, I had no shirt on, and just wearing the lounge pants with no underwear. With the two women standing next to me I felt both embarrassed and excited. I also was aware of my erection, but there was nothing I could do about it.

Also, Kay was still dressed up from going out for dinner and she was wearing her high heal shoes. We are both about the same height, but since I had my legs spread and Kay had on high heals, I was actually looking up at her. So this made me feel even more vulnerable.

“Kay, I rigged the rope system so you control it over there on the wall,” Ann told Kay. “That way you can make it higher or lower as needed. Now is a good time to try out your new paddles. I actually made three for Clyde. Once I heard that you are having Clyde carry a bag with some spanking stuff in it, I also made him an extra paddle that was like the thinner paddle, but not quite as long, so it would fit in the bag.”

Then standing in front of me, Ann showed both Kay and me the paddles. It felt sort of strange being helpless, yet knowing what I would be spanked with.

“I always spank Clyde on his bare bottom, so lets take off his lounge pants,” Kay said.

I felt them disconnecting the spreader bar and then felt my lounge pants slide down my legs. My legs were spread wide apart again and the spreader bar was reconnected. Now I was totally naked and was aware of my erection.

Then Ann said, “The thinner paddles will work better when Clyde is standing like this. Try them on him first. I see you have a riding crop. Let me stand in front and that way he can really get spanked.”

They were talking like I wasn’t even there! Kay said, “Clyde complains a lot but he can take a good spanking and I like the way his butt quickly turns red.”

As Ann was hitting my tender upper inner thighs she said, “Yes, Clyde really quickly reacts in front too. Do you have a shoelace? I can show you something I learned from another girlfriend.”

“If you go upstairs, I believe Clyde wore dress shoes with shoe laces. You could use one of those,” Kay said.

Kay continued to spank me as I watched Ann go upstairs and returned with a shoelace from my own shoes. I was terribly embarrassed and excited when Ann was standing in front of me with the riding crop, but now she was holding on to my erect penis and balls and wrapping the shoelace around the base of my penis. “One of my girlfriends showed me this,” Ann said. “It is suppose to make a man hold his erection longer. Clyde should buy some extra shoelaces so he can carry them in his bag and you can have them on hand in your new special room.”

“That is a great idea,” Kay said. “Clyde, I will expect you to buy some shoelaces before our next date.”

“I need to leave soon, but lets see if Clyde can secure himself over your new spanking bench and see how well the new wider paddle works,” Ann said.

Then I felt my ankles being disconnected from the speader bar, and the overhead rope was lowered and my wrists were disconnected.

“Clyde, walk over to my new spanking bench, spread your legs and secure them first, and then see if the hooks that Ann put in will secure your wrists?” Kay said.

“Yes, Mistress,” I answered. I knew Kay liked to be addressed as ‘Mistress’ when she spanked me, so I answered in that way. Now I felt very embarrassed securing myself to this new piece of furniture that I just picked up from an antique store this morning. It was easy to spread my legs and secure my ankles to the bench, and then I leaned forward and the clips on my wristlets easily clipped into the hooks. Now I was helpless again. I did try to undo the clips on my wristlets, and I couldn’t free myself from the bench. With the shoelace around the base of my penis, I was very aware of my penis and balls dangling between my legs.

“Clyde looks very good this way,” Ann said. “Now you can order him to secure himself to this and have him wait for you to spank him. So try out the new paddle.”


This paddle did sting a lot more than any other paddle Kay had used on me.


“I like this new paddle,” Kay said. “I also like the way it covers his whole butt.”

“I can bring over the bill for the new stuff I added when Clyde comes over again. It looks like everything works like I expected it to,” Ann said.

“Why don’t you bring it over the bill tomorrow on Sunday morning. I hope Clyde will spend most of Sunday with me. I think we make a good couple and he makes a good boyfriend for me,” Kay said.


“Don’t you agree, Clyde. You will see me again on Sunday. Right!”

I felt I had no choice than to say, “Yes, Mistress. I can be here Sunday morning.”

“I guess I will leave now, and I will put the extra stuff in his new bag. You should enjoy your new room and paddles,” Ann said. “Remember, I am always available to customize something for you and Clyde.” Then Ann left the room and went upstairs.


“Ann and I are actually best friends from high school. We see each other a lot and do things together, so I hope you like her too.”


“I am just starting to know Ann. I do know she is very skilled at her work.”


“Clyde, I hope I don’t need to spank you like this on every date, but you do need to respect me more and to stop complaining.”


“I do want to please you everyway I can, and I hope we can keep on dating. That is why I accept these spankings from you.”


“Your naughty bottom is now turning red, so I know you are going to remember this spanking. Before I quit spanking you I want you always to thank me at the end of your spankings. So thank me now.”


It felt embarrassing to say this , but I said, “Thank you for spanking me, Mistress.”


“Very good! Now let me do one last thing before we go upstairs.”

Then I felt her stroke my still very erect penis. With my legs spread wide apart and secured, it felt so good that I just relaxed and let my cum shoot into her hands. As I came, she untied the shoe lace and I felt myself explode. Now I was feeling a warmth from the spanking and at the same time, a great pleasure of cuming.

“What I like about you Clyde, is how well you react to my touch. Let me clean you up before I release you.”

Kay went to the downstairs bathroom and came out with a warm and wet washrag and that also felt very good and wonderful. Then she released me from the spanking bench and said, “Put on your slippers and lounge pants, then sit on the couch and wait for me. Be sure and bring up your bag, too. I want to slip into something more comfortable.”

Soon, I was sitting on her couch when Kay came in wearing just a see-thru nightie and pair of panties. “Now Clyde, I want you to have this bag with you at all times. Carry it in your car when you go to work and bring it with you on dates with me. Also, always bring it into my house when you are dating me. Before our next date, be sure and buy shoe laces for both your bag and for downstairs.”

Then she handed me a key that was attached to a thin leather necklace. “I want you to also wear this key at all times. It is the key to the room downstairs. I will always keep the room locked, and that way you can unlock the room and prepare yourself to be spanked. The key will also be a constant reminder of our new relationship. Be sure the paddles, spreader bar, shoe laces, cuffs, lounge pants, are always in your bag.”

“Yes, thank you for the key and I will always carry the bag with me.”

Then we started to kiss and fondle each other. Before I left Kay’s house, I promised her that I would spend the whole day Sunday with her, and I would be at her house at 10 AM.

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