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MY DATE P 1-4  


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,” 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.”


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.”


“One,” I said.

“Good, you’re learning.”


“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.”


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.


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.


“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.”


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.


“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.


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.


“One,” I said.


“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.”


“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.


“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.”



“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.


“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!”


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.


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



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

“Yes, Madam,” I said



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”


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.”


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.”


“One”, I said.


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


“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.

Posted : 09/07/2011 10:38 pm