My Date - By Otkfme

• Part 1 - My First Spanking - Just because I was late.
• Part 2 - Double Spanking - Spanked for being disrespectful.
• Part 3 - Jane’s Friend Mary – Spanked by both Jane and Mary.
• Part 4 - Credit Card denied – Everything goes wrong at the restaurant.
• Part 5 - Jane’s girlfriends – I meet and get spanked by Jane’s girlfriends.
• Part 6 - Turning the Tables – This time I get to spank Jane.
• Part 7 - Jane’s Mom – I finally get to meet Jane’s mom.
• Part 8 - Jane’s Sister – I get to meet and the rest of her family.
• Part 9 - Bad Shopping Trip – My date went bad at the mall.
• Part 10 - Jane’s Work – I am late in picking Jane up for lunch.
• Part 11 - Secret Spanking Society – Jane is part of a secret spanking organization.

My Date - Part 1

Through some friends, I had met Jane and had gone out with her. On my first date, I met her at a movie theater, and I was about ten minutes late. Sometimes I don’t keep track of time very well, and nothing was said about me being late.

On our second date, we met at a restaurant, and I was twenty minutes late. Jane was upset about me being late, but we still had a good time together. So at the end of the date, I asked her if I could pick her up at her house when we went out again. She said that it would be okay with her, but she would no longer tolerate me being late. If I wanted to keep going out with her, I would have to be on time. She indicated that she liked me, but that I was disrespect of her by showing up late all of the time. I told her that I would be on time, and that I really enjoyed her company.

Our third date happened on a Friday night. Everything went wrong in traffic for me. The traffic was heavier and a whole lot slower than usual and I got lost twice, in trying to find her house. When I finally got there, I was a half-hour late. I rang her doorbell, Jane opened the door and said, “Well, you finally got here. Your are a half-hour late. Come on in for a moment.”

Once I was inside, she quickly shut the door behind me and said, “You said that you wanted to keep going out with me and that you would be on time!”

“I’m sorry. Traffic was backed up and I had trouble finding your house.”

“That’s just an excuse. If you really cared about me, you would have been on time. I should forget about our date and send you home right now, if this is the way you respect and treat me.”

“No, don’t do that. I really like you, and I would do anything to make it up to you.”

“Anything?”

“Anything,” I said, again.

There was a table near the door, and Jane grabbed a paddle that was sitting on the table. “Do you agree to a spanking from me? It’s either a spanking, or you walk out of the door right now, and you never see me again.”

I really liked Jane, so I said, “I really want to continue to see you, so I guess I will agree to a spanking.”

“I was hoping you were going to say that. I like you, too, but you have to show me more respect by being on time.”

“So what’s next?” I asked.

“You were thirty minutes late, so I am going to spank you sixty times with this paddle. Drop your slacks and bend over the table.”

I unbuckled my belt, and let my slacks fall to the floor and bent over the table. “I was wondering if you wore briefs or boxer shorts for underwear, and now I can see that you are wearing shorts,” Jane said. Then I felt her fingertips in the waistband of my shorts. I quickly stood up and grabbed the waistband of my shorts to keep them in place.

“If you want to ever go out with me today or ever again, you better bend over the table again and let me pull down your shorts. I always give a spanking on the bare bottom, it has a better effect that way.”

I didn’t like it, but I bent over the table again and felt Jane pull my shorts down to my feet. Now I was naked from the waist down, in front of a woman that I was just getting to know.

“Lift your feet up so that I can get these out of the way.” Jane said. I didn’t want to get her mad at me, so I lifted my feet and I soon saw her put my slacks and underwear on a nearby chair.

“These are the rules. I will give you sixty swats of the paddle on your bare behind. You are to count out each one. If you forget to count, that swat will be given again. For everytime you rise up or put your hands behind you to protect your bottom, you will receive five extra swats. You are to say nothing unless asked to, and even then you should answer with either “Yes, madam or No, madam. Do you understand?”

“Yes,” I answered.

I felt a swat and Jane said, “Yes, what?”

“Yes, madam,” I answered.

“That’s better,” Jane said. “Now spread your legs apart a bit, and I will start your spanking.” I spread my legs, but Jane said, “ A little bit more.” Now I was aware that my penis and balls could be clearly seen by Jane hanging between my legs, and I was totally exposed for a spanking by her.

“That’s better,” Jane said. “Remember my rules.”

SWAT

The first swat stung me more than I had anticipated. I automatically stood up and rubbed my bottom.

“Bend back over the table again. You stood up and forgot to count, so you will now get sixty-five swats of the paddle. We are starting at one again.”

SWAT

“One,” I said.

“Good, you’re learning.”

SWAT

“Two,” I said. I did pretty well until I got up to fifty swats. My poor bottom felt on fire, and I wasn’t sure if I could take anymore. I kept bent over the table and said, “I have learned my lesson. Can’t you stop spanking me. It really hurts.”

“It’s suppose to hurt,” Jane said. “That is the only way you will learn your lesson. But for speaking when not being asked to, that adds five more swats, so now you will get seventy swats.”

“Yes, madam,” I reluctantly said.

SWAT Then my spanking continued.

When Jane got to my last swat, before she spanked me she said, “I expect you to stay in position after your last swat. Do not stand up until I tell you to. Is that understood?”

“Yes, madam,” I said.

There was a long pause, then SWAT. It really hurt but I stayed bent over the table. “Seventy,” I said.

Then I felt her soft hands rubbing my bottom. “Do you agree to a spanking like this for everytime your are late, and two swats for every minute you are late.”

I really wanted to keep dating Jane, so I said, “Yes, madam.”

“And do you agree to a spanking from me for anytime I feel that you are disrespecting me?”

I wasn’t sure what I was agreeing to, but I said, “Yes, madam.”

“To show me that you are sincere, I want you to stay in position while I five you five more swats in quick concession. You don’t have to count these, but stay in position, even after they are given to you.”

SWAT, SWAT, SWAT, SWAT, SWAT.

My bottom was really on fire, but I stayed in position. Jane rubbed my bottom, again, and said, “Your bottom is bright red, now. You may have trouble sitting, during our date. I look forward to keep going out with you and giving you more spankings. You can stand up, now.”

So I stood up and immediately rubbed my bottom. I forgot that I was naked from the waist down, and was showing Jane my erect penis and balls. Although the spanking really stung my bottom, I guess it also excited me.

Jane noticed and said, “It looks like you also enjoyed the spanking. Here are your clothes. Get dressed now, so that we can get on with our date. I have found out a lot about you, already, and I want to get to know you better.”

This was my first but not my last spanking from Jane. But those are other stories.


My Date - Part 2

In my last story, you found out about my girlfriend named Jane. She has a great personality and a nice body. I like being with her because we seem to think the same way. Anyway, she had warned me about being late on my dates with her, and on my last date, she spanked me for being so late. The following story is what happened on my next or fourth date with Jane.

I had really tired to be on time; I even left with what should have been ten minutes to spare. When I rang Jane’s doorbell, I was ten minutes late. Her door was open and Jane yelled out from inside the house, “Come on in.”

After entering her house, I saw a paddle on the nearby table and a note that read, “You are late, again. Take off your slacks and underwear and put them on the chair. Then bend over the table. I will be out, shortly, to spank you.”

I was aware that I was late, but I was hoping that I wouldn’t be spanked, again. On our last date, Jane told me that I should expect to be spanked for being late and for any other thing that I did wrong while on a date. I had to agree to be spanked, or else never see Jane again.

So now I was naked from the waist down and bent over the table, awaiting my spanking. Next, I heard footsteps and smelled Jane’s sweet perfume, and Jane said, “It’s too bad you are late, again. Now, you will receive another spanking. Let’s see, you were ten minutes late so you will receive twenty swats of the paddle.”

I felt the paddle hit me in my inner thighs and Jane said, “Spread your legs some more and remember to follow the rules.”

One of Jane’s rules is to speak only when spoken to, and to answer with either “Yes, madam” or “No, madam.” So I answered with, “Yes, madam.” When I had my legs spread like this, I am sure that Jane could easily see my penis and balls hanging down.

“Remember to count,” Jane said.

SWAT

I had forgot how the paddle stung my bare bottom, but I said, “One.” It had been a whole week since my last spanking from Jane.

SWAT

“Two”, I said.

As Jane continued to spank me she said, “I thought you had learned your lesson from your last spanking, but I guess not. Also, remember that during our date, if you do something that is disrespectful to me, you will receive another spanking. Do you understand?”

So between spanks I said, “Yes, madam.”

After the nineteenth swat, Jane said, “This will be your last and hardest swat. Remember to count it and stay in position.”

SWAT

Jane really must have put a lot into that swat. I automatically stood up and grabbed my burning bottom. “I was hoping that would happen,” Jane said. “You just earned yourself five more swats. Bend over again, and we are still at nineteen swats.”

Although my bottom was on fire, I bent over the table again for my six more swats. This time I stayed in place and didn’t stand up. After the last swat if the paddle, I stayed in place while Jane examined my bottom.

“Your bottom looks red, again. You will probably feel your spanking during our entire date. You can stand up and get dressed, now.”

Like last time, I had a good erection when I stood up and rubbed my poor naked bottom. Jane noticed it, too. But I quickly got dressed and soon we were off on our date.

We ate out at a fine restaurant and saw a good movie. When we got back to Jane’s house, she invited me in, which I thought was a good sign. Jane sat down in the middle of a long couch in her living room, and I sat beside her.

“We need to talk,” Jane said.

“Okay.”

“If you really want to keep going out with me, you need to show me more respect.”

“I respect you. What are you talking about?” I asked.

“I noticed how you were turning your head away from me and watching the other women while we were eating in the restaurant. You also have a habit of walking way ahead of me instead of walking with me.”

“I didn’t realize that I was doing that,” I replied in my defense.

“Well, if you want me to keep going out with you, I want you to be aware of those things.”

“Now that you told me, I will be more aware of my behavior when I am with you,” I said.

“I want to make sure you about that. Remember that during your spanking, today, I told you that I would spank you again if you were disrespectful during our date?”

“I guess so.”

“Well, that’s what I intend to do. Stand up and stand in front of me.” Once I was standing in front of her, she said, “Now put your hands on your head and leave them there until I tell you to let them down again,”

Once my hands were atop my head, Jane unbuckled my belt, and slid down my slacks. Then she slid down my undershorts and had me step out of my clothes again. My penis was erect again but Jane said, “Now stand beside me, let your hands down, and lie over my lap with your penis between my legs.”

Jane hiked up her short skirt and soon her thighs pinned me in place. “Now I will give you a good handspanking, until I think you will really respect me.”

“Yes, madam,” I obediently replied.

After a few minutes, the spanking was really hurting my already paddled bottom. I started to squirm around, but Jane said, “You better stop moving about. It will only let your spanking last longer.”

Jane then pulled me closer to her body and squeezed her thighs tighter together, and continued my spanking.

“Your bottom is bright red, again. You can get up and sit by me again, but don’t put your clothes back on.”

I was glad my spanking had quit, and I carefully sat down beside her.

Then, with one of her hands on my penis, she gave me a long kiss and said, “I’m so glad that I have met you and that you are willing to receive spankings from me. I am looking forward to going out with you and also spanking you some more.”

Then we talked some more, and then I was allowed to get dressed and leave. What a date that was!!


My Date - Part 3

Traffic was backed up again. I was running late. My car was low on gas and I needed to fill up. I was really trying to be on time, but I was running late again. When I got to Jane’s house, I ran the doorbell, and she yelled from another room, “Come on in. You’re late.”

As usual, there was a paddle on the table and a note that just said, “You are late, again!” I knew what that meant, that I was going to get paddled, again. Jane expected me to take off my slacks and underwear, put them on the nearby chair, and bend over the table. So that’s what I did. I felt very exposed and vulnerable like this, and Jane always waited a few minutes before she came out of her bedroom to spank me. As I waited, I thought I heard Jane talking to someone. Maybe she was on the phone. But then, something unexpected happened. Jane and another woman her age approached me.

Once they were close to me, Jane said, “This is my friend, Mary. Mary, this is Clyde. Clyde, this is Mary.”

“I’m glad to meet you,” Mary said. “Jane told me that she spanks you if you are late, and it looks like it is true.”

“Mary also has a boyfriend who is always showing up late,” Jane said, “and I told her that she could spank you. This way she would know how to spank her boyfriend. Is that alright, Clyde?”

What was I supposed to say? So I simply said, “Yes, madam.”

“I guess you do follow Jane’s rules when being spanked.” Mary said. “I do see why you like him. He does have a nice ass. Is it okay if I feel him between his legs?”

When I heard that, I quickly put my legs together and started to stand up. I didn’t want a woman who I had just met to touch my private parts.

SWAT, SWAT, SWAT

Jane had picked up the paddle and had given me three quick swats.

“You can either put your clothes on right now, walk out the door and never see me again, or get spanked by Mary and all the preliminaries to your spanking. So which will it be?” Jane asked.

“I really like you, so I guess I’ll take the spanking from Mary,” I said.

“I thought you would say that,” Jane said. “So bend over the table and spread your legs for me. By the way, that will cost you five extra swats.”

Once I bent over the table, Jane raised up the back of my shirt and pressed down with one hand on the center of my back. I spread my legs and Jane said, “Spread your legs a little bit more than that.”

Then I felt Mary’s hand cupping my balls, and then she put a hand around the shaft of my penis. “He has good equipment,” Mary said. “No wonder you like him.”

“Feel how firm his bottom is,” Jane said. Next, I felt Mary’s hands feeling my bottom cheeks.

“Clyde does have a firm bottom,” Mary said. “I see why you like spanking him.”

“Well Clyde, you were fifteen minutes late. That gets you thirty swats of the paddle, plus five more for standing up. So Mary, give him thirty-five swats with the paddle.” Jane said.

“Are you all set for your spanking from me?” Mary asked.

“Yes, madam”, I obediently answered.

“Remember to count,” Jane said.

SWAT

“One,” I said.

SWAT

“Two” Compared to how Jane spanked me, I could barely feel the swats.

But then after five swats Jane said, “You can spank him a lot harder than what you are doing. Give me the paddle and let me show you.”

SWAT

“Six.” I could sure feel the difference. Jane continued with four more swats.

“See how his bottom is turning red. That means that you are spanking him with enough force. Now you take over and finish giving him his thirty-five swats.” Jane said.

SWAT

“Eleven.” Now it felt like Jane was spanking me. I knew that my bottom would be burning hot, by the time I got the thirty-five swats from Mary.

Mary kept paddling my poor bare bottom until she got up to thirty-four. Then Jane said, “After your last swat, please stay bent over the table so that we can examine your bottom.”

SWAT

“Thirty-five.”

“See how bright red his bottom is.” Jane said. “That shows that he really felt the spanking. Also, go ahead and feel his bottom. You will see that it is real hot.”

Then I felt four hands on my bare bottom. “Yes, it is rather warm,” Mary said.

“Now, Clyde, you can stand up now and rub your bottom.” Jane said. But when you do, face Mary and thank her for spanking her.”

“But then she will…” I started to say.

SWAT, SWAT, SWAT

“You know you are not to answer me that way during your spanking,” Jane said. “Either stay bent over and I will spank you some more or stand up and thank Mary.”

I didn’t want to be spanked anymore, so I stood up, and while rubbing my burning bottom, I said, “Thank you, Mary, for spanking me.”

I knew that Mary could easily see my erect penis. When I get spanked, it has this affect on me.

“Now get dressed so that we can go out on our date,” Jane said.

While I was getting dressed, I heard Jane tell Mary that she could spank me again at another time. Then Mary left, and Jane and I went out on our date.


My Date - Part 4

If you remember from Part 3, I had just been spanked and paddled by Mary, Jane’s friend. I had just received thirty-five swats from the paddle, plus some extras. My bottom was sore and hot with fire, but I was now on my way, out the door, with Jane, my girlfriend. I had reservations at a really nice restaurant in a shopping center. I hadn’t told Jane, because I wanted it to be surprise.

At first, Jane wondered why we were going to the shopping center. But when we got to the restaurant, we both got a surprise. It was a formal place to eat, which required a tie and suit coat for men, and most of the women were in gowns. I was told that I could rent a coat and tie at the restaurant for $45.00, which would be added to the bill. I asked Jane if she still wanted to eat there. She said she had always wanted to, but she thought it was too expensive. She told me that she wanted to by a nice dress at a nearby shop, and for me to rent the tie and coat. Jane came back wearing a beautiful dress. We were seated, had wine together, and had a fantastic meal. We had a great conversation, and I felt so happy that I had found Jane, because we shared so much in common. As we were eating, she told me that I should have told her where we were going to eat, so that she could have dressed appropriately. She also told me that she would take care of my breakdown in communication, once we got back to her place.

The check came, and I paid by my credit card. I guess I was over my limit, and it was denied. I had left my checkbook at work, and I had no other credit cards. I also realized that I had only ten dollars in cash. So I turned to Jane, explained the situation, and she gave them her credit card, which was good. Jane was silent as we let the restaurant. On the way to her house, she was really mad! She told me that not only would I have to pay her back for the restaurant, but also for the dress she bought. Also, that she was going to spank me in a way that I would never let this happen again.

As we walked through the door of her house, she told me to take off my shoes and socks, my shirt and undershirt, and put them on the chair near the table. Then to go out to the living room and sit on the couch. She would be out shortly. When she came out, she was wearing a short black skirt and a black halter-top. She was also carrying some things in her hands. She sat down beside me and said, “Stand up and stand directly in front of me.” Jane grabbed a hold of my hips and had me stand in front of her. “Now put your hands on your head and keep them there until I tell you can take them down.” She unbuckled my belt, zipped down my zipper, and unbuttoned my jeans. Then she glided them to the floor. As I felt her fingertips inside the waistband of my under shorts, she said, “I was hoping that I would never need to spank you like this, but tonight you really messed things up.” Then she slid my under wear down my legs. I had to step out of them, and then she put them beside the couch. I was now completely naked in front of her. It made me feel like a naughty little boy, who was just about to be spanked by his teacher.

Jane scolded me, “You really embarrassed me tonight. First, with not telling me where we were going, so that I could have dressed appropriately. Second, by not being able to pay the high restaurant bill. There is no excuse for that type of behavior. Hopefully, by spanking you, your behavior will change. Now don’t you agree that you deserve to be spanked?”

There wasn’t anything else I could say but, “Yes, madam.” I really liked Jane, and if enduring this spanking meant that she would keep going out with me, it was worth it.

“Your spanking will take place in two parts. The first part for not telling me where we were going, and the second part for me having to pay for our meal. So go over to the end of the couch and bend over it.”

The couch was at just the right height that it put my poor bottom at the very top of it. “Lean over some more and spread those legs.” My legs were already spread, and this made the tender insides of my bottom cheeks really exposed. “I am going to use a strap on you. It hurts more than the paddle, and you will receive thirty strokes. As usual, count them out, and if you get out of position, you will receive five extra strokes. Do you understand?”

“Yes, madam.”

Earlier that evening, I had received thirty-five swats from the paddle, and now thirty with the strap. I would never forget this evening.

“Here’s your first one!”

SWAT

The strap hurt much worst than the paddle. I quickly stood up and rubbed my poor bottom.

“That will be five extra. Bend over, again. Now you will receive thirty-five strokes. Start counting at one, again.”

I didn’t want to, but I bent over the couch.

SWAT

“One.” I had to really concentrate on staying bent over.

SWAT

“Two”

“Are you going to keep in better communication with me?”

“Yes, Madam,” I said

SWAT

“Three”

Although my poor bottom was on fire, I was able to stay in position for the thirty-five strokes of the strap. “Stay in position while I get ready for the next phase of your spanking,” Jane said. She then placed a wooden chair in the middle of the living room.

“Now stand up and walk over to that chair and bend over it. Since the bill came to a little over one hundred dollars to eat, plus the rental of your coat and tie, I am going to give you ten strokes of the cane. Have you ever been caned before?”

“No, madam,” I said. I heard of them being used in schools in England, and I knew they really hurt. I was hoping that I would only be paddled. But now I will get the cane.

“If you move out of position or forget to count, the stroke will be given again. Are you ready?”

“Yes, madam”

WHACK

The cane was even worst than the strap. It felt like a hundred bees had stung me in a row on my poor bottom. I stood up, and rubbed my bottom.

“You stood up and forgot to count, so that stroke will be given again. I know this really hurts, but bend over again.”

WHACK

The cane really hurt my already spanked bottom and I stood up again.

“I can’t have you standing up after every stroke. Let me try something different with you.” Jane turned around the chair so that the seat was facing me. “Put your knees on the seat of the chair and bend over it.” I did as I was told, and Jane said, “I think this will work. Stay like that while I get something.”

Jane left the room and came back with rope and some other stuff. “I’m going to put these wrist cuffs on you, and tie your arms to the legs of the chair. This will keep you in position.” Then she proceeded to secure me to the chair. After she was done, Jane said, “Now try to move.” Of course I couldn’t, so she said, “Good, now I can continue on with your caning.”

WHACK

“One”, I said.

WHACK

“Two,” I tried to move, but I was secured in place.

WHACK

“Three.” This continued until we reached eight strokes. Then I complained, “Do you really have to give me all ten strokes. This is really painful.”

“I want you to learn your lesson. Now you will receive eleven strokes, one extra for talking.”

Then my caning continued until I had received all eleven strokes. Jane put down the cane and examined my poor bottom. “Your bottom looks really sore. I’m going to get something to sooth the pain.”

Jane left the room and came back with a towel and a jar of something. She put them on the couch and came over to where I was secured to the chair. “I’m going to untie you from the chair, and then I am going to sit on the couch. Come over and lie face down on the couch so that your penis is between my legs.”

It felt good to be released from the chair, and I felt the ridges the cane left on my poor bottom. I laid on top of Jane, and she rubbed something cool on my bottom. It felt real nice and it made me excited.

“Spread your legs so that I can rub this all over your red bottom.” Soon, I felt her hands between my legs, rubbing the cream all over me.

“Clyde, you can talk openly to me now. It looks like we are going to be boyfriend and girlfriend now, and I would like you to meet more of my friends, besides Mary. Do you agree?”

“Yes, that sounds good. I would like to meet them,” I said.

“Instead of going out next weekend, what if I invited them over for a pot-luck and to meet you?”

“That sounds good.” I said.

Then Jane spanked me a few times with her hand and said, “And you better be at your best behavior, or you will be spanked again.”

“I’ll be real good for you,” I said.

“Good, I’ll set that up with my girlfriends for next week. Now stand up in front of me.”

When I stood up, I had an erection from Jane rubbing my bottom with the cream. She said, “Keep your hands to your sides and come closer to me.” Then she proceeded to stroke my penis until I came. She wiped me off with a towel that she had on the couch and said, “I think you have had enough spankings for one evening. You can get dressed now and I will see you at 6 PM next Saturday. Be good, and I am looking forward to showing you off to my friends.”

I got dressed, we hugged, and I kissed her good night. As I drove home, I wondered if next week I would be spanked in front of her friends.


My Date - Part 5

I was real anxious to see Jane, again. Last time I saw her we had a wonderful time eating at a fine restaurant. The bad thing was that my credit card was up to it’s limit, and it was declined. So Jane paid for everything, and I had to pay her back. What made things even worse for me, when we got back to her house, she spanked me. As a child my parents spanked me, but Jane was the first grown woman to spank me. At first, it was when I was late picking her up for the date. But now, it seems like she finds any excuse to spank me. This may sound strange, but I think I am starting to enjoy being spanked by Jane. Her spankings do hurt, I felt her last spanking for most of the week, but it shows that she really cares about me. I also enjoy going over her lap for an over the knee spanking. It puts my naked body close to hers.

Anyway, this is what happened on Saturday. Jane said she was inviting her girlfriends over to meet me. So when I arrived, on time, at six o’clock, her friends were already there. It was a potluck, and the food was already arranged and the table set. As I walked in, Jane quickly introduced me to everyone. One of her friends that were there was Mary, who Jane let spank me one time when I was late. Besides Mary, there were four other women besides Jane. They seemed to want to get eat real fast, and they said that I could go first. The food was good and I answered a lot of questions. I told them that I worked in research at a computer company, and I really enjoyed my work. I also told them that it was nice to meet this many women, all at the same time.

After we ate, they had me sit out in the living room while they cleaned up everything. After they were done with the clean up, they all gathered in the living room. Each woman was wearing a number, from 1 to 6, and they also gave me some packages to open, which were also numbered.

Jane said, "the packages are not for you to keep, but they contain things for a game we will play tonight. Each of my friends has brought something for the game. So start opening the packages."

I didn’t know what to expect, and the first one contained a ruler. Jane said to put it on the coffee table, and put the number from the box, next to it. The next box I unwrapped contained a wooden spoon. This also went on the table with a number. The next boxes contained a glove, a ping-pong paddle, a hairbrush, and the strap that Jane had used on me to spank me. Now I knew that I was probably in for another spanking.

Then Jane reached over and handed me one more box. When I opened this box, it had a die in it and a sheet of paper that said, "Rules of the Game."

All the women wanted me to read the rules out loud so that we could start the game. I read the rules out loud and they said:

"This is a game so that my friends can get to know you better. It is a simple game, but it should be an enjoyable game for all of my friends. When you first roll the die, it will determine who spanks you. If you notice, everyone is now wearing a number. When you roll the die, again, it will determine which spanking implement they will use. After you gave rolled the die twice, you are to pick up the spanking implement and take it to one of my friends who is wearing that number. Then you are to ask her to please spank you. Each of my friends will be allowed to spank you twenty times with the chosen implement, and in whatever position they chose. This may be bent over the couch or table, an over the knee spanking, over a chair, or whatever they choose. The game will be over once everyone has spanked you. Depending on how you roll the die, you may be spanked by the same person more than once. Once you are ready to start the game, Take off your shoes, socks, and shirt, then come over where I am seated. Jane."

This was really unexpected for me. Jane must have told her friends that she spanks me, and all of them must have joined in to think up this game. I took off my shoes, socks, and shirt, and went over to Jane.

"See how well he follows what I say to do," Jane said. "This is one of the reasons I like Clyde so much. I always spank his bare bottom, and you should, too." Jane undid my belt, unzipped my slacks, and guided them to the floor. "See, he is wearing shorts, I like that, too." Then her fingers were in the waistband of my shorts, and then I was standing naked in front of all of her friends. Jane lifted up my feet so that I could step out of my slacks and underwear. "Slowly turn around so that everyone can see your nice bottom and penis and balls." It was so embarrassing being completely naked in front of all these women. They were all commenting on how I looked.

Then all of them started saying, "Roll the die so that we may start spanking you!"

So I picked up the die and rolled a 2. I looked around the room and Cindy, a cute blonde, was wearing number 2. I rolled it again and came up with 3. On the coffee table, number 3 was the ruler.

"Clyde, now you need to go up to Cindy and ask her to spank you with the ruler," Jane said.

So I took the ruler and handed it to Cindy saying, "Cindy, please spank me with the ruler."

"I would be delighted to," Cindy replied. She got up out of her chair, grabbed my penis and said, "Follow me. I want you to bend over the end of the couch."

After I had bent over the couch, Jane said, "Spread your legs, Clyde, like I have you do for me when I spank you." It hurts more when my legs are spread in this manner, because then my whole bottom is exposed. Also, it allows them to see my penis and balls. "This goes for Cindy and everyone, before you spank Clyde, you can feel him between his legs if you wish."

Then I felt Cindy’s hands feel my balls and stroke my penis. "I see why you like him as a boyfriend," Cindy said. "Now get ready for your spanking."

SPANK. "One", I said. The ruler stung me, but it didn’t hurt very much.

SPANK. “Two,” I said.

“Does Jane spank you very often?” Cindy asked.

“She didn’t spank me on our first dates, but since I have been coming over to her house, she has found a reason to spank me sometime during each date,” I replied.

SPANK. “Three,”

“Do you like being spanked by Jane?” Cindy asked.

SPANK, SPANK, SPANK. “Four, five, six. I like to please Jane and be close to her.” I replied.

SPANK, SPANK, SPANK. “Seven, eight, nine.”

“But do you like being spanked?” Cindy asked again.

SPANK, SPANK, SPANK. “Ten, eleven, twelve. It warms my bottom and it makes me sexually excited, so I guess I like them, but the spankings give me a sore bottom.”

“They are suppose to make your bottom hurt,” Cindy said.

SPANK, SPANK, SPANK, SPANK. “Thirteen, fourteen, fifteen, sixteen.”

“Well, your bottom is just starting to turn red. Here’s your last four.”

SPANK, SPANK, SPANK, SPANK. “Seventeen, eighteen, nineteen, twenty.”

Then Jane said, “Clyde, thank Cindy for spanking you, then get up and roll the die again.”

So I said, “Cindy, thank you for spanking me.” And I got up and rolled the die, again. This time it was the number one. I looked around the room and Mary was wearing number one. I rolled the die again, and it was #4, which was a hairbrush.

I took the hairbrush over to Mary and she said, “I’m so glad I get to spank you, again. I’m going to sit in the middle of the couch, so lie over my knees.” After I was over her knees she said, “Remember to spread those legs!” Now my penis was between her legs, and she was holding my arms in the middle of my back so I couldn’t move about. “You don’t have to count these. SWAT It was so SWAT good that Jane SWAT let me spank you. SWAT Now I am SWAT spanking my boyfriend. SWAT It has gotten SWAT closer together SWAT and I believe SWAT that he actually SWAT enjoys being SWAT spanked by me. SWAT He is treating SWAT me much better SWAT now. I believe SWAT every man SWAT needs a spanking SWAT now and then.” SWAT, SWAT, SWAT. “Stand up, now, and see who spanks you next.

I had just received my first forty spanks and I had at least sixty to go. My poor bottom was already burning. I rolled the die and got 5, which was a redhead named Sue. I rolled again and got 6, which meant the strap.

Jane said, “Sue, the best way to give him the strap is over the back of a chair. Everyone should help hold Clyde in place. He tends to move about a lot when he is strapped.” Then Jane put a chair in the middle of the room, and I bent over it. “Everyone come over here. There should be on of you on each of his arms and legs.”

So now I was being held in place by all of Jane’s friends while being strapped. They did a good job, because I jerked about a bit.

It went on like this until every one of Jane’s friends, including herself, spanked me. Although I had a very sore bottom, I still had an erection. Jane saw my state of being and said, “Clyde has been a good boy to endure this spanking. Let me reward him by jerking him off.”

Then she led me over to the couch. “Mary, hold his hands behind his back and everyone else gather round.” Jane said. Then Jane stroked my penis until I came in front of all of her friends. Since everyone had seen me naked, and had spanked me, I was told to leave my clothes off for the rest of the evening.

Before any of her friends left, they were told that they could help spank me, at any time. This was some evening, I got to meet Jane’s friends, and they really got to know me better. I had a very sore bottom, and I wondered what was going to happen to me the next time I had a date with Jane.


My Date - Part 6 - Turning the tables

I have been going out with this woman named Jane. At first Jane spanked me if I was late for a date, then she spanked me if I displeased her during a date. And the last time I saw her, she had her friends over, and they all spanked me. I really like the way Jane and I share the same thoughts and values, and I have to admit that the spankings have been sort of a turn-on for me. It was really embarrassing to be spanked by Jane and her friends, but at the same time, it was very exciting for me.

Anyway, this time I left work with plenty of time to spare, to get to her house on time. I arrived a few minutes early, and her front door was ajar. I rang the bell, and she yelled in the background, “Come on in. I’ll be ready in a few minutes.”

On the table was the paddle. Jane probably thought that I would be late, again. So I went into her living room and sat on the couch. The minutes went by, and after a while, I went over to the table and picked up the paddle. Our date was suppose to start at 7 PM, and now it was 7:20. Jane finally came out of her bedroom. She had on a really short mini-skirt, and she looked fabulous.

“I’m sorry it took me so long, I wanted to make sure my make-up was just right.” Jane said.

“It’s not alright!” I said. “If I get spanked for being late, you should be spanked for being late.”

Jane saw that I had the paddle in my hand and said, “If you think that you are going to spank me with that paddle, you are mistaken.”

I grabbed her arm and led her over to the table where she would spank me if I were late. “What do you think you are doing?” Jane asked.

“You are going to get a bare-bottom spanking, just like what I get from you, when I am late. So hike up your skirt and bend over the table.” I put my hand on the small of her back to help Jane bend over. She hesitated, then hiked up her skirt and bent over the table. Then I bent down, grabbed the waistband of her panties, and pulled them down to her feet. “Now step out of your panties,” I said. And soon I had her small delicate panties in my hands. I then put the panties on a nearby chair. Since Jane always had me spread my legs, I said, “Now be a good girl and spread your legs.” I took the paddle and tapped the insides of her thighs until she had her legs spread like I had mine, when Jane spanked me.

I could see her sex glistening with dew, and I reached up and touched it. “What do you think you are doing?” Jane asked.

“Just the same thing you do to me, before you spank me,” I answered. “Let’s see. You were twenty minutes late, so you will receive forty swats from the paddle. Be sure to count them out loud.”

Then I started to paddle Jane. I started soft, but as I went on, I spanked her harder and harder. When I had reached thirty spanks, her white bottom had turned a nice shade of pink, and her bottom felt warm to the touch. By the time I had given her all forty spanks, her bottom was bright red, and I knew that she had really felt the sting of the paddle.

“Don’t get up yet,” I told Jane. “I want to feel your bottom and look at the effects of the paddle.” Her red bottom felt very warm, and when I felt her sex between her legs, it was very moist.

“You can get up now, and rub your bottom.” I said.

With her mini-skirt still hiked up, she stood up and rubbed her hurting red bottom. Then she came over to me and kissed me. I cupped her warm naked bottom with my hands, and we kissed for a long time.

“I was hoping that you would spank me. You see, I like to be spanked as well as spanking you. I hope that we can share in spanking each other for the rest of our lives. Why don’t we just stay here and love each other.”

That night turned out to be the best date that I have had with Jane. We made passionate love all night. Now I had found out that we both liked being spanked, and we enjoyed spanking each other. What a wonderful life we could live with each other.


My Date - Part 7 - Jane’s Mom

It was a Saturday night and I had another date with Jane. I didn’t have to work, so I allowed plenty of time to get to her house. I didn’t want to be spanked for being late, again. When I arrived, I rang the doorbell and Jane yelled out for me to go ahead and walk in. Seated on the couch were Jane and an older woman. They both stood up and Jane said, “Clyde, I would like to introduce my mother to you. And mother, this is Clyde.”

“Glad to meet you, Mrs. Miller,” I said.

“Oh, you can just call me Kathy,” her mother said. “Jane has been telling me a lot about you. Would you mind sitting on the couch by me, I have some questions to ask you?”

“Sure, I would love to visit with you,” I said.

“Good, Jane why don’t you sit in a chair over there, for now.” Kathy said. I sat down on the couch beside Jane’s mom. She didn’t seem old enough to be Jane’s mom. Kathy was wearing a white blouse and a short black skirt. “I guess you have been dating my daughter Jane for about three months, is that true?”

“Yes it is!” I replied.

“And do you like my daughter?”

“Yes, I even love her. We are so compatible with each other. We even share the same ideas and values.”

“Jane tells me that you have even met her friends.”

“I have met her friends,” I replied. I didn’t want to mention the fact that they also spanked me.

“If you like my daughter so much, why haven’t you introduced her to your friends?”

“I guess I haven’t got around to that.”

“And Jane hasn’t seen your house, yet!”

“I guess your right, she hasn’t seen my house.” I replied.

“Jane also tells me that you have already had sex with her. Is that true?”

I stared at Jane and said, “You told your mother that!”

Kathy abruptly said, “Clyde, I’m talking to you. Please answer the question. Have you had sex with her, already?”

“Yes we have,” I answered.

“Jane also tells me that she has spanked you. Is that also correct?”

“Yes it is,” I reluctantly answered. I looked over at Jane. She had a smile on her face,

“Do you want to keep seeing my daughter?”

“Very much so, Mrs. Miller,” I said.

Well, I believe that you should be spanked for how you have treated my daughter so far. You say you love her and you have had sex with her, but yet, you have NOT shared your life with her. That is disrespectful to my daughter. Don’t you agree.”

“When you put it in those terms, I guess I agree with you.”

“Although Jane now has her own house and is a grown woman, I still need to make sure my daughter is treated with respect by anyone who dates her. Don’t you agree?”

“Yes, I think it is good that you care about your daughter.”

“Good. Then you agree to be spanked by me for being disrespectful to my daughter!”

I hadn’t realized that I had agreed to be spanked by Jane’s mother. “Did I agree to a spanking?” I asked.

“Yes you did. Now stand in front of me while I prepare you to be spanked.” Kathy commanded. Slowly, I got up from the couch and stood in front of her. “Put you hands on top of your head and keep them there.” Then she unbuckled my belt, unbuttoned my slacks, unzipped my zipper, and pulled my slacks down to my ankles.

“I see you are wearing boxer shorts, just like Jane said you would be. But this is going to be a bare bottomed spanking, so down they go.” Kathy reached her fingertips inside the waistband of my boxer shorts, and slid them down my legs. I was now standing naked from the waist down, in front of Jane’s mom. I felt so embarrassed.

“I can already see why Jane likes you. Step out of your things so that they will be out of the way.” I lifted my feet and she completely took off my slacks and under shorts. “Jane, why don’t you take these and put them out of the way. Clyde will not be needing them, for a while.” Jane picked up my clothes and put them in a corner and sat back down in a chair across from where I was standing. “Keep you hands on your head and turn around so that I can see your bottom.”

I turned around and felt her hands on my bottom. “Jane did say that you had a firm bottom. I guess she is right about that. You may drop your arms, stand by my side, and lay over my lap.”

Kathy hiked up her skirt, and I felt like a little boy about to be spanked by his mommy. “I’m going to start you out with a hand spanking.” SPANK, SPANK, SPANK “I want my daughter to be treated with respect.” SPANK, SPANK, SPANK “Did Jane also tell you that I spank her dad.” SPANK, SPANK, SPANK.

“No,” I replied.

SPANK, SPANK, SPANK “It is good that Jane spanks you.” SPANK, SPANK, SPANK “I guess it runs in the family.” SPANK, SPANK, SPANK “Your spanking will have two more parts to it.” SPANK, SPANK, SPANK “The second part for not sharing more of your life with Jane.” SPANK, SPANK, SPANK “And the third part for having sex with her, already.” SPANK, SPANK, SPANK

Kathy spanked me for about five more minutes then said. “You can get up now, and take off your shirt. Hand it to Jane and then bring over the paddle from the table. Jane, take his shirt and then move one of your wooden chairs to the center of the room.” I took off my shirt and handed it to Jane. Then I got the paddle from the table and handed it to Kathy. “Now put your knees on the seat of the chair and bend over it.” I was now totally naked and bent over the chair, ready for Jane’s mom to paddle me.

“You would make a good husband for Jane. She told me that you even accepted a spanking from her girlfriends. Is that true.”

I felt embarrassed that Jane had told her this, but I replied, “Yes it is true, they did spank me.”

“A well-spanked man is a well-behaved man,” Kathy said. “Now get ready for 30 swats from the paddle.”

SWAT, SWAT, SWAT, SWAT, SWAT. “So you are now going to have Jane met your friends.” SWAT, SWAT, SWAT, SWAT, SWAT.

“Yes, madam,” I replied I wanted to make sure I answered Jane’s mom with respect.

“Very good.” SWAT, SWAT, SWAT, SWAT, SWAT. “And you are going to show her your house.” SWAT, SWAT, SWAT, SWAT, SWAT.

“Yes, madam,” I replied.

SWAT, SWAT, SWAT, SWAT, SWAT. “And are you always going to respect my daughter?”

“Yes, madam.” SWAT, SWAT, SWAT, SWAT, SWAT.

My bottom felt on fire, and I knew that there would be a third part to my spanking. “Now stand up and don’t rub you bottom. Walk over to the side of the couch and bend over it.”

I did so then she said to Jane, “Do you have something else that I can spank him with?”

“Yes, a strap. I have used it on him, before.” Jane replied.

“Good, go and get it.” Jane left the room to get the strap. “This will be for having sex with my daughter, already. I don’t want you to take advantage of her.”

“Here’s the strap, mom.” Jane said.

“Clyde, you will receive six strokes of the strap. I expect you to count these out and stay in place.”

SWAT. “One.” It really stung on my already well-spanked bottom.

SWAT. “Two.”

“After your six strokes, I want you to stand up and thank me for spanking you. Then bend over the couch, again. I am sure that Jane will want to give you a few more strokes of the strap. Do you understand, Clyde?”

SWAT. “Three. Yes, madam.”

“And if I hear from Jane that you have been disrespectful to her, you can expect another spanking from me. Is that understood?”

SWAT. “Four. Yes madam.”

“I hope Jane keeps going out with you.”

SWAT. “Five.”

“You seem like a nice man.”

SWAT. “Six. Thank you, madam.”

“You can stand up, rub you bottom, and thank me.”

Although I had an erection, I stood up and rubbed my bottom and said, “Thank you for spanking me, Mrs. Miller. I really do love your daughter and hope to marry her some day.”

“That is good to hear,” Kathy answered. “Now bend over the couch, again, so that Jane can finish your spanking.”

As I bent over, Jane’s mom said, “I’ll let myself out. It was good that I got to met and spank Clyde.”

“Talk to you later, mom.” Jane yelled.

I heard the door open and shut and then Jane said to me, “I am very proud of you.” SWAT “And I am glad that my mom got to spank you.” SWAT “It shows me that you really do love me.” SWAT “And you do respect me.” SWAT

“You can stand up, now.” I stood up, rubbed my poor sore bottom, and Jane threw her arms around me. We kissed and kissed, and then we made love. I wondered what my next date would be like with Jane!


My Date - Part 8 - Jane’s sister

I went out with Jane a couple more times, showed her my house, and she met a few of my friends. It was getting close to Thanksgiving, and she invited me to a family gathering. It would take place at her sister’s house, Connie, who lived fairly close to Jane. Since we were going out pretty steady, Jane thought that I should be included in her family events. I had met and been spanked by her mom, but had not met her dad yet, or her sister, Connie.

When Thanksgiving morning came around, I picked up Jane and we went to Connie’s house. I met George, Jane’s father, and Roger, Connie’s husband. Jane’s sister was about five years older than Jane, and also looked real cute. Roger, her husband, was about my same height and build, and he worked for the Fire Department. I guess Roger and Connie had been married for about five years.

We sat around the table, ate good food, and her family asked me a bunch of questions. I told them that I was in love with Jane and that I hoped that we would marry each other in the future. Her family was very pleasant to be around.

Around three o’clock, Jane’s mom and dad had to leave. They had another event they needed to attend. Shortly after that, Roger, Connie’s husband had to leave on a fire call. That left just Jane, Connie-Jane’s sister, and myself. They wanted to talk some more, and they had me sit in the middle of the couch, with Jane on one side of me, and Connie on the other.

Connie said, “It’s good that everyone has left. Now I can really get to know you a lot better, Clyde.”

“Okay, what else do you want to know about me?” I asked.

“Has Jane told you that I spank Roger?” Connie asked.

Spanking was never mentioned until now, and I was hoping it wasn’t going to be brought up. But I answered, “No, she hasn’t.”

“And is it true that Jane spanks you?” Connie asked.

“Yes it is,” I answered. I turned to Jane and said, “You told your sister that you spank me!”

“We keep no secrets in this family,” Jane replied.

“And our mom has recently spanked you, as well as Jane’s friends?” Connie asked.

“Yes, it is true.” I replied.

“I know that you haven’t done anything recently to deserve a spanking, but I would like to spank you, Clyde,” Connie said.

Jane jumped in and said, “You have been spanked by everyone else, let Connie spank you!”

“I will only spank you if you agree to it on your own free will.” Connie said.

“Please let Connie spank you,” Jane said.

I was hoping that I won’t be spanked on Thanksgiving, but I said to Connie, “Okay, I guess I will agree to be spanked by you.”

“Good, I didn’t want to be left out in being able to spank you. But before I spank you, let me show you and Jane the rest of the house.”

Jane showed us the bedrooms on the first floor, and then she took us down to the basement. There was what looked like a woodworking shop in the basement. “Roger is real good with working with wood. It’s just a hobby for him, but he could probably start a business of making things out of wood for people. If he see something, or even a photo of something, he can usually make it out of wood.” There were a lot of saws, hammers, and many woodworking tools.

Jane then led us to the next part of the basement. There was a room that was locked, and as Connie unlocked the door, she said, “This is a room that even our parents don’t know about. They think it is a storage room.”

When Connie opened the room, it was carpeted, and it had various paddles, whips, etc., hanging on the walls. In the middle of the room were various spanking benches, wooden horses, and other wooden devices. And on the wall, was a wooden X, and other wooden things that one could be secured to.

“I had no idea that you had a room like this in your house,” Jane said.

“Yes, I had no reason to show it to you until now. This is where I spank Roger. Roger also made most everything that is in here, except for the spanking implements, of course. And since Roger and Clyde have about the same build, they should also work real good on Clyde.”

“I still can’t get over this room,” Jane said as she was looking over the various spanking furniture,

“Clyde, you said that you would submit to a spanking from me. So I want you to take off all of your clothes, except for your under shorts, then come over to where I will be sitting.” Connie said.

I thought that I would just receive an over the knee spanking from Connie, I wasn’t expecting this! As I undressed, Connie sat on a chair and Jane stood next to her. I walked over to Connie and she said, “Keep your hands at your sides while I pull down your under shorts.” Then I felt Connie’s fingertips in the waistband of my under shorts, and she slid them down my legs. “Step out of them, please.” Now I was standing totally naked in front of Jane’s sister, with Jane watching. Next, Connie surprised me by grabbing and fondling my penis and balls. I started to have an erection and Connie said, “Good, he reacts like Roger does.” Then she released my penis and balls and said, “Turn around, and remember to keep your hands at your sides.”

I turned around, and immediately felt her hands on my bottom. “He does have a nice butt. It will be fun spanking him.” Connie said.

“I’m glad you are finally going to have a chance to spank, Clyde.” Jane replied.

Then Connie stood up, grabbed me by the penis, and led me over to a piece of spanking furniture. “This is something I really like to spank Roger on. Let’s try it on Clyde.”

The front of it looked like a stock. It had holes for my wrists and neck. But the bottom of it was about one and a half feet off the floor, and it had two small platforms that were spaced about three feet apart.

“Get up on this. Put one knee on each side, and bend over so that your neck and wrists are in the stock.” It took a little bit of maneuvering on my part, but soon my legs were spread, and I was bent over with my head and wrists in the stock. Connie closed it, and now I was held in place by the stock and was unable to see what was going on behind me.

“Jane, there are straps by his knees. Watch what I do, and secure his knee in place while I take care of his other knee.” Then I felt the straps go around each thigh, near my knee. “Also, the are ankle straps to secure his foot in place.” The I felt both feet secured to this device. Now my legs were spread wide apart, I was fully bent over, and I was secured in place.

Connie then said, “I like to spank Roger on this device because his bottom is fully exposed, and I can also easily get to his penis and balls.” With that she grabbed my penis and balls, again.

“Yes, I see what you mean,” Jane said.

“I’m going to start your spanking out with a paddle,” Connie said. Then she started to paddle me. While she was spanking me, she said to Jane, “I have already discussed this with Roger, since I found out that you spank Clyde. You can borrow this room at any time. Just call me first, to make sure I am not spanking Roger in it. I would also be willing to help spank Clyde in the future, so you will know how to use everything in the room.”

“That would be great!” Jane said. “We live so close, so it would be easy to bring Clyde over here for his spankings. Don’t you think so, Clyde.”

I was in no position to object, so I just said, “I guess so.”

“I guess so, what?” Connie said as she spanked me with the paddle.

“It would be nice to bring me here to spank me,” I said.

“That’s good to hear you say that, Clyde.” Jane said. “Connie and I will have fun spanking you in her special spanking room.”

“Let me show you what a riding crop can do.” Connie said. It stung a lot more than the paddle. I tried to pull away from it, but I was securely in place. “And if you get tired spanking him on his butt, you can use it on his balls and penis.” Then I felt her tapping my balls and penis with the crop. Being so exposed in this position and with her tapping me, I immediately had another erection. “See how he reacts to the crop.”

“Very good,” Jane said. “Let me try the crop.” Then Jane spanked me and tapped my penis and balls with the crop.

“This position lends itself to something else,” Connie said. I heard various noises behind me, and then felt a jelly or lotion being rubbed around my asshole. It actually felt good, compared to the spanking I had until now.

“Have you ever put your fingers inside of him?” Connie asked Jane.

“Put on a glove like I have on. Lubricate your fingers, and try it. Do it slowly, and start with one finger.” Connie said.

“Okay, I’ll try it!” Jane said.

“What’s nice about having him on this device, is that his butt checks are already spread wide apart for you.” Connie said.

Then I felt Jane’s finger slowly go into my asshole. It actually was a big turn-on for me. She even stuck her other finger in, then a third, and she felt around inside me.

“See how he is reacting to it,” Connie said, as she grasped my penis.

“I guess it really excites him.” Jane said.

Then Connie said, “I think Clyde has had a lot of excitement for one day. Let’s take him down off of this, then I have one last thing to do to Clyde.” They released my legs, and raised the half of the stock, so I was able to stand again. Then Connie led me by my penis to another spot on the room. “Stand still and hold out your wrists.” Connie put wrist cuffs on me, secured them to a bar above me, and raised it up. “Spread your legs” Then anklets were put on me, and a bar was secured between my legs. “This is called a spreader bar. It keeps his legs apart. Let’s also blindfold Clyde, so he can’t see what is happening.”

A blindfold was put on me, and then I felt a condom being put on my erect penis. “This is so that you don’t mess up the carpet.” Connie said. “Jane, I will spank him while you make him cum. Let’s start!”

What a sensation! I was feeling pain and pleasure at the same time. Soon I was shooting cum into the condom.

Connie took off my blindfold, and said, “You took your spanking very well. I look forward to spanking you, again.” She released me, and she showed me to the bathroom, where I could get rid of the condom and clean myself up. “You can get dressed now, we will be waiting for you upstairs.” Connie said.

When I got upstairs, Jane said that I could expect many more spankings like this one from her and Connie. She was also interested in trying the other spanking benches and spanking furniture.


My Date - Part 9

After having Thanksgiving dinner with Jane’s family, and the erotic spanking I got from Jane’s sister, Connie, I thought that we were really coming together as a couple. On my next date with Jane, I arrived on time so I won’t be spanked, and then we went to the mall. Jane wanted to look at dresses and clothes, so I went off on my own and visited other stores. At noon, we ate in the “Food Court”, a place where you could get fast food, and then Jane did some further shopping. I didn’t want to sit around in the women’s clothing stores all day, so I went shopping on my own, again, and met up with Jane later.

After we got into my car to leave from the mall, Jane was furious at me! As I was driving, she got out her cell phone and called her sister, Connie. This is what I heard. “Hi, Connie. It’s good that you are home. I was just shopping at the mall with Clyde, and he needs a good spanking for the way he treated me. Can I really use the room like you said I could.----Good! And are you available to help?---We are about five minutes away from your house. See you in a little bit.----Thanks, Goodbye.”

Then Jane said to me, “You are going to get a good spanking for the way you treated me, today. You say you love me and you want to marry me, but you don’t act like it, sometimes. I want to make sure you never treat me like this, again. Drive to Connie’s house for your spanking.”

“But I don’t see what I did wrong.” I replied.

“I will explain it to you as I spank you. Don’t say another word. Just drive to Connie’s house.”

I was confused. I had just spent most of the day with Jane at the mall, and I didn’t see why she was so upset with me. We got to Connie’s house, and I was quickly escorted to the spanking room downstairs. “Strip down to your under shorts, and stand in front of me,” Jane commanded as she sat down on a chair. As I took my clothes off, Jane talked to her sister about assisting with my spanking. I next stood in front of Jane and as she was taking down my under shorts she said, “I was hoping that you would learn to treat me with respect. That we would do things as a couple.” My under shorts were now at my feet and I stepped out of them. “Now get on your knees as I scold you for your behavior.”

I felt like a naughty little boy, being scolded by his mommy. “I was hoping that you would stay in the stores and help me pick out dresses and clothing that you would like me to wear. Instead, you went shopping on your own. There were also nice restaurants at the mall that I would have rather eaten at. But no, you had us eat in the food court. You need to change your behavior if I’m going to keep going out with you.”

“I’m sorry,” I said. “I didn’t realize I was treating you that way.”

“You will be a lot sorrier after your spanking. I hope your spanking will make you act like we are a couple on our next date.” Jane said to me. Then Jane turned to Connie and said, “Where do you spank Roger when he needs a good long spanking?”

“I know just where to put him.” Connie said.

“Stand up, now, and follow Connie,” Jane said to me.

Connie went over to something that looked like a tilted box on legs. One side of the box was higher than the rest of the box. “Bend over this,” Connie said.

I bent over the high side of the box. My arms went down on the other side of the box, and there were wristlets down there. Connie secured my arms in front of me. Then a strap went around my back so that I couldn’t stand up. Another strap went behind my knees, and held my legs in place. This left my poor bare bottom up in the air, ready to be spanked.

“You should probably start his spanking out with this paddle,” Connie said to Jane. Then my spanking started.

As Jane was spanking me, she said, “Clyde, you need to take care of my needs, too, if we are going to function as a couple.” SPANK, SPANK, SPANK “It is more than just taking me to the mall,” SPANK, SPANK, SPANK “It’s being by me the whole time,” SPANK, SPANK, SPANK “And sharing with me.” SPANK, SPANK, SPANK.

For just starting out, she was spanking pretty hard. I could really feel the sting of the paddle.

“If you really want to get his attention, use this paddle. It has holes in it,” Connie said. When Jane first spanked me with that paddle, I could feel the difference. It really stung my poor exposed bottom.

“Ouch!” I said.

Jane said, “Good! Now maybe I am getting my point across to you.” SPANK, SPANK, SPANK “After this spanking, you won’t want to sit down for a while.” SPANK, SPANK, SPANK I wanted to get away from the paddle and being spanked, but I was secured in place. SPANK, SPANK, SPANK

“I’m sorry. I won’t behave like that, again.” I pleaded

SPANK, SPANK, SPANK “I’ll make sure of that with this spanking.” Jane answered. SPANK, SPANK, SPANK

“Oh, look how red his bottom is getting,” Connie remarked. “Why don’t you switch to this. It is called a cat-o-nine tails, or cat for short. Let me show you how to use it.” Then I felt many fingers hitting me across my bottom at the same time. They wrapped around me, and made sure that my whole bottom was well spanked. “Now you try it.”

Jane didn’t hit me as hard as Connie, but the fingers still stung my bottom. Although I could hardly move, I tried to twist my body to get away from it. Then Connie said, “You should stop spanking him for now. Rub some lotion on his bottom, and let’s leave him down here while we talk upstairs. That way Clyde can think about his spanking and how he is going to change his behavior.”

“Good idea!” Jane said.

Then I felt a soothing lotion rubbed on my burning bottom. “Stay right here, we will be back in about fifteen minutes,” Jane said. Then I heard them talking upstairs. I couldn’t tell what they were saying, but it was a very animated conversation. I was still strapped down in a spanking position, with my sore red bottom sticking high in the air. Then I heard them come down the stairs.

“Are you going to treat Jane a lot better?” Connie asked.

“I sure am. I don’t want to be spanked like this, again,” I answered.

“Good. But before we let you up, we are going to give you six strokes of the cane. I will give you the first three, and Jane will give you the last three. You will count them out loud, and say ‘Thank you, madam’, after each stroke. Is that clear, Clyde?” Connie said.

“Yes,” I said. I felt a smack of a paddle on my bottom.

“Yes, madam.” I replied.

“Have you ever been caned before?” Connie asked.

“No, madam.” I replied.

“The cane can be quite painful, but I think your behavior warrants it.” Connie said.

I felt a tapping of something on my bottom, heard a whistle, then it felt like a hundred bees had stung me in a straight line on my bottom. I tried to stand up to rub my bottom, but I was still secured to this spanking bench. “Ouch!!!! That really hurt!” I exclaimed.

“You forgot to count or say Thank You, Madam, so that stroke will be given again.” Connie said.

I felt the tapping again, heard the whistle, and felt the severe pain, again. “One. Thank You, Madam.” I said.

“Very good,” Connie said.

Then I counted as Connie administered two more strokes of the cane. Now it was Jane’s turn. Her strokes hurt as much as Connie’s. Before Jane’s last stroke, Connie said, “Give his last stroke in this area.” I felt her fingers at the base of my bottom. “He is real tender down there, and it will make a lasting impression on him.”

I felt a tapping at the base of my bottom, the whistle, and it felt like the base of my bottom was being burned by a hot iron. I was just barely able to say, “Six. Thank You, Madam.”

“I hope that I never have to spank you like this again, Clyde.” Jane said. “But if you keep going out with me and keep ignoring me, you will get another spanking like this one.”

“We should rub lotion on his bottom before we let him up,” Connie said.

Then I felt four hands rubbing lotion on my poor hurting bottom. “I can feel ridges from the cane.” Jane said.

“Yes, and the ridges or welts will stay with him for a couple of days, maybe even a week. He will remember this spanking for a long time.” Connie said.

They finally unstrapped me from the spanking bench. I was told to get dressed, and then join the upstairs. Even with the lotion, my bottom was on fire and really hurt. From now on, I knew that I had to care as much about Jane as I did for myself. I didn’t want another spanking like this one!


My Date - Part 10 - Jane’s work

I took a personal day off at work so that I could see Jane’s work, and have lunch with her. Jane works at a company that consults with other companies on advertising and PR. The building that Jane works at is in the middle of downtown, and it is a large office building. Jane said to take the elevator to the fourteenth floor, and someone would direct me to her office. Well, there was a traffic jam in the downtown area, so I was about thirty minutes late getting to her office. I walked in and was greeted by a young woman about 21 years old.

“I’m Tami, Jane’s secretary, and you are?” She said.

“I’m Clyde, Jane’s boyfriend. I was supposed to have lunch with her at noon. I guess I’m a little late.”

“Jane has been expecting you, and she is very mad that you are late. I’ll let her know that you are here as soon as she gets off the phone. Did you know that she is one of the main three people who run this company?”

“I wasn’t aware that she had that important of a job”

“She runs a very tight ship around here. You need to do things the exact way she wants them done; otherwise you pay the consequences. Good, she is off the phone, now.” Tami picked up the phone and said, “Clyde has finally arrived. Should I send him in?” Tami hung up the phone and said, “You can go in, now.”

When I entered Jane’s office, Jane was walking around her desk and she sat down on a chair. “Come over here, stand in front of me, put your hands on your head and don’t say a word.” Then she began to unbuckle my belt, unzip my zipper, and take down my slacks. “You know better than to show up this late when I was hoping to have lunch with you at noon.” Jane next had her fingertips in the waistband of my under shorts, and they were now at my ankles.

“Step out of these and then bend over the desk and hold on to the other side, while I set these out of the way.” After I was bent over the desk, I guess my shirt was partially covering my bottom. She went to her desk drawer and said, “I need to get a pin to keep your shirt out of the way, and I guess I will spank you with this ruler.” Jane pulled out a nice long ruler and then pinned my shirt out of the way. “Spread your legs some more. That’s good. Now I expect you to stay in this position for the duration of your spanking. Your are thirty minutes late! Usually, that would mean sixty spanks, but in this case I am going to spank you for fifteen minutes.”

This whole situation was a big surprise to me. I thought Jane would understand that traffic was bad, and we would be off to lunch, together. And I know that Jane spanks me when I am late for a date at her house, but I didn’t anticipate that I would be spanked in her office. “I’m sorry I’m late.” I pleaded.

“You will be a lot sorrier once I have spanked you. You should have allowed a lot more time to get here. Remember, time is valuable to me.” SPANK, SPANK, SPANK “You have been on time, lately. I thought that maybe you realized how important time is for me.” SPANK, SPANK, SPANK

Just then, Jane’s office door opened and Tami walked in. She looked at Jane and me and said, “If I am disrupting anything, I can leave. I thought you were leaving for lunch and I needed to get this urgent message to you.”

I was quite embarrassed. Here I was, almost completely naked, bent over Jane’s desk and Jane was spanking me. I wish that I could run and hide. Jane sensed this, and put her hand on the small of my back to keep me bent over. “It’s OK. I’m giving Clyde a spanking for being so late. What is your message?”

“Rowe and Graves called. They are having an emergency meeting in a half-hour and they want you there for the it. That’s about a twenty minute drive from here. What should I tell them?”

“I guess I better to go to that meeting. Tell them that I will attend and that I will be right over. Then come back into my office, again.” Jane said. “Now see what you made me do, Clyde. I missed my lunch, again. I’ll have to pick-up something on the way over there.”

I thought that since Jane was leaving for her meeting, I wouldn’t be spanked, anymore. But then Tami walked in. “Tami, I want you to finish spanking Clyde. He needs to stay in position, and you should spank him for at least fifteen minutes. You can use this ruler, your hairbrush, or anything else you can come up with. Any questions?”

“No questions. You better leave for your meeting. Don’t worry, I’ll spank Clyde real good.” Tami said. Then Jane rushed out of the office. “Does Jane spank you a lot? Tami asked.

“Lately she has. If I do anything that displeases her, I am spanked.” I said.

Then Tami started to spank me with the ruler. She didn’t spank me as hard as Jane, and I thought I was getting off lightly. But then Jane’s office door opened, and a woman about Jane’s age walked in. She looked surprised and said, “What are you doing?”

“This is Clyde, Jane’s boyfriend. Jane had started to spank him for being late, but then she had to go to a meeting. So she told me to take over in spanking him.”

I was really embarrassed, now. First, a young woman that I had just met was spanking me, and now another woman sees me like this. “Tami, you are needed to answer Jane’s phone and to make her appointments. Why don’t you go do your regular job, and I’ll finish spanking Clyde.”

“OK,” Tami said. “Jane wants him spanked for fifteen minutes. He is to stay bent over the desk until the spanking is over, and you are to use this ruler, a hairbrush, or anything else you can come up with.” Then Tami left the room.

“Let me introduce myself,” the woman said. “My name is Robin and I am also one of the main key people who run this company. Jane and I work on projects together, a lot of the times. It was good that I had a question for her. Otherwise, I would not of had a chance to spank you. Jane had mentioned that she has been dating you, and that she also spanks you. Let me examine your bottom.”

Then I felt her fingers on my bottom. I was also wondering how many other people that Jane had told that she spanks me. “You do have a firm butt. It seems like the ruler hasn’t reddened it much. There is a recreational room one floor down with ping-pong tables. Let me get one of those paddles, I’ll be right back. Stay in position.”

Then she went out the door. I was hoping that no one else would see me like this. In a few minutes Robin came back, again. She was carrying two ping-pong paddles. “I brought two paddles up because one has rubber on it and the other is just plain wood. I will start with the one with rubber on it, that one should sting more. By the way, I have two teenage boys, and I still spank them. Let’s see, it’s 12:45. I guess you will be spanked until one o’clock.”

Robin then proceeded to spank me with the paddle. It stung a lot more than the ruler did. While Robin continued to spank me she asked, “Does Jane always have you spread your legs when you are spanked?”

“Usually she does,” I answered.

“It’s a nice touch. That way even the tenderest parts of your bottom gets spanked. Does she spank you very often?”

“Jane usually thinks up an excuse to spank me about once a week.” I answered. The paddle was really starting to sting my bottom, so I started to move about a little bit.

“Don’t move about like that. Hold still or else I will spank you even for a longer time. Yes, your butt is turning a nice shade of red. You have about five more minutes left to your spanking. I think I’ll try the other paddle, now.”

I tried to hold still, and the other paddle didn’t sting so bad. Robin kept spanking me for what seemed like an hour, then she said, “It’s one o’clock. You can stand up, now.”

I stood up and rubbed my poor tender bottom. Even though I had an erection, I kept rubbing my bottom because it really hurt. Robin then stood in back of me and unpinned my shirt. “Once Jane returns, I will be anxious to tell her that I ended up spanking you. I think she will enjoy hearing that. I hope that we can see each other, again. Maybe I will have a chance to spank you, again.”

Then Robin left Jane’s office. I found my clothes and got dressed. As I was leaving the office, Tami said, “Next time I hope that I can spank you for a longer time. If Robin spanked you, your butt should be pretty sore.”

“It sure is,” I replied. Then I finally left the office. What a way to spend a personal day off from my regular job!


My Date - Part 11

It was nearing Christmas and Jane and I had dated for about 6 months. Jane and I had nearly the same belief system and we agreed on many things. We both liked doing the same type of things and Jane was fun to be around. However, Jane spanks me. At first it was for being late for a date, but then she would
spank me for not treating her properly or not giving her enough respect. Her friends, sister, and her mother have even spanked me. When Jane spanks me, it hurts, but I feel that it has brought us closer together as a couple. I really want to marry Jane, someday.

On this date, I was told to be at Jane’s house at 6:30 PM on a Thursday night, and to eat before I arrived. I thought this was strange because we usually started our dates at 7 PM, and we also ate out. This was also the second Thursday of the month, and Jane usually had something going on every second Thursday of the month, where we couldn’t go out.

I had been spanked enough times by Jane for being late, so I made sure that I left in enough time to be on time. I rang the doorbell, and a woman’s voice said, “Come on in.” When I entered the living room, there was a woman who I had never met before seated on the couch. Beside her was Jane’s paddle and
two wristcuffs. Also, the room had a lot of folding chairs in it, and a black wooden horse.

The woman stood up and greeted me, “You must be Clyde. My name is Shirley, Jane’s neighbor in the blue house.”

I walked over to her, shook her hand and said, “Glad to meet you.”

“Jane is busy right now, but she wanted me to meet you and spank you.”

“But I was on time, and there is no reason for you to spank me,” I complained.

“Jane said you might object, but you will see shortly why I need to spank you. If you don’t submit to a spanking by me right now, Jane will spank you even longer and harder. Besides, I want to ask you some questions and get to know you better as I spank you.”

“If Jane really wants you to spank me, I guess I better let you spank me.” I said.

“Good! Remember Jane’s spanking rules during the spanking. Only speak when spoken to, and address me as madam during the spanking. It that clear.”

“Yes,” I replied.

She swatted me on my bottom with her hand. “Yes, What?”

“Yes, madam,” I corrected myself.

“That’s better. Let’s start by you taking off your shirt and then holding out your wrists for the cuffs.” I didn’t like to hear this because it meant that I would be secured in position for my spanking. I was hoping to get just an over the knee spanking from her. After the cuffs were put on my wrists Shirley said, “Put your arms behind your back and turn around.” Then I felt the wristcuffs being secured together.

“Now turn around, again.” Then she unbuckled my belt, unbuttoned my jeans, unzipped the zipper, and soon my jeans were at my feet. I felt so embarrassed. I had just met this woman, and now she was undressing me for a spanking. Next I felt her fingertips in the waistband of my undershorts, and they were at my feet. “Step out of these and then put one foot on the couch so that I may take off your shoes and socks.” Soon I was standing totally naked in front of her.

Shirley grabbed my penis and lead me over to the wooden horse. “Jane wants you secured to the wooden horse for your spanking.” She freed my arms from behind me and said, “So bend over it.” Immediately, she resecured my wrists to the legs of the horse. “Spread those legs.” Then I felt cuffs being put on my ankles, and then my ankles were secured to the legs of the horse.

“Jane wants you spanked until your bottom cheeks turn pink or red.” Then Shirley started to spank me with the paddle. SPANK, SPANK, SPANK. “Do you love Jane?” she asked. SPANK, SPANK, SPANK.

“Yes I do, madam!”, I answered.

SPANK, SPANK, SPANK. “Do you want to marry her?” SPANK, SPANK, SPANK.

“Yes I do, madam.”

SPANK, SPANK, SPANK. “Jane tells me that she loves you, too.” SPANK, SPANK, SPANK. “And that she loves to spank you. Do you like being spanked by Jane?” SPANK, SPANK, SPANK.

“Yes I do, madam.”

SPANK, SPANK, SPANK. “Then why don’t you give Jane an engagement ring for Christmas.” SPANK, SPANK, SPANK.

“That sounds like a good idea, madam.” I replied. I had been thinking about getting a ring for Jane. But by being spanked by Shirley and questioned like this, it has really made me realize that Jane would probably like to be engaged to me.

SPANK, SPANK, SPANK. “So are you going to go out and buy Jane a nice diamond engagement ring?” SPANK, SPANK, SPANK.

“Yes, madam.”

SPANK, SPANK, SPANK. “Good! I know that it would be the best Christmas present that Jane could receive.” SPANK, SPANK, SPANK. “You know, I really enjoy spanking you while you are secured to this wooden horse.” SPANK, SPANK, SPANK. “It keeps you bent over for your spanking, and it also gives me good access to the other parts of your body.”

Then I felt her fingers on my balls and erect penis. “I spank my husband and boys. I may look into getting one of these.”

Next, I heard Jane’s voice. Jane asked Shirley, “How is his spanking coming along?”

“Real good. His cheeks are pink and starting to turn red.” Shirley answered.

I felt two pairs of hands on my bottom cheeks. “His bottom is also warm to the touch.” Jane said. “Has anyone else arrived yet?”

“Not yet,” Shirley answered. “But shouldn’t we blindfold Clyde?”

“I forgot about that,” Jane answered. “Let me get a scarf from my room. I’ll be right back!”

SPANK, SPANK, SPANK. “We don’t want you to recognize anyone, Clyde. You will find out why in about a half hour.” Shirley told me. SPANK, SPANK, SPANK.

Then Jane put a scarf me and covered my eyes so I couldn’t see. The doorbell started to ring and I heard many women’s voices. Some I recognized as Jane’s sister, some of her co-workers, and her friends. I was really embarrassed because I was still secured to the wooden horse, completely naked, with my well-spanked bottom up in the air. Jane and Shirley were talking to everyone as they came in.

“Have a seat, everyone.” Jane said. I heard a lot of commotion, and then everyone was quiet. “Welcome to our fourth monthly meeting of WOMEN WHO LIKE TO SPANK MEN. Since our last meeting, we are now the 42nd group of women in the national organization.” There was a lot of applause. “Just think,
there are groups like us meeting once a month across the United States. This is an open discussion group where we can share ideas in spanking men. Who are here for the first time?... And who have never spanked a man before?... Well, I have my boyfriend Clyde here, and if you want to spank him, you can after the meeting.”

They went on to discuss what they liked to use to spank their men, positions, etc. I found it fascinating to hear it from a woman’s perspective. But I didn’t like to know that I would be further spanked by women that I didn’t know and couldn’t see. Jane’s sister, Connie, also told the women that the wooden horse that I was secured to was made by her husband, and that he was willing to make other wooden horses for those who wanted them. Connie also told them that she spanked her husband.

The meeting went on for a while, then it finally ended. I could tell that Jane was standing close to me by the sound of her voice. Several women asked if they could spank me. Then my spanking started again. Then paddle stung my well spanked bottom, but I didn’t complain. After about a five minute spanking by the various women I couldn’t see, I guess everyone left.

“Thanks for helping out, Shirley!” Jane said.

“I was glad to be able to help out. I’ll let myself out, so that you can attend to Clyde.” Shirley said.

Then Jane untied the scarf around my eyes. “We didn’t want you to be able to identify the women who were here, tonight. Now you can see what has kept me busy on every second Thursday night of the month. And know it is my turn to spank you a few times.” SPANK, SPANK, SPANK. “You have been real good to take a spanking like you did, tonight.” SPANK, SPANK, SPANK. “Now you see where there is a good size group of women in this area who like to spank their men.” SPANK, SPANK, SPANK.

Next I felt Jane take off the ankle cuffs and freed my legs. Then she came around in front of me and undid my wristcuffs. I was finally able to stand up and rub my well spanked hurting bottom. Jane gave me a big kiss, and then we went over to the couch and made love. If I marry Jane, what am I getting myself into?

My Date - Chapters 12 - 22